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Can you really afford to become a one-income family? In this episode of Making a Millionaire, Tyler and Mikaela share how they went from nearly $92,000 of debt, an $84-month car loan, lifestyle inflation, and costly home renovations to building a $400,000 net worth in their early 30s. Their journey highlights budgeting, emergency funds, investing, 401(k) strategies, Roth IRA planning, 529 accounts, employee stock purchase plans (ESPPs), RSUs, family financial planning, and the Financial Order of Operations. If you're wondering how to pay off debt, save for retirement, build wealth with one income, or balance financial independence with raising a family, this episode is packed with real-world lessons and actionable insights. Jump start your journey with our FREE financial resources⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Reach your goals faster with our products⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Take the relationship to the next level: become a client⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Subscribe on YouTube for early access and go beyond the podcast⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Connect with us on social media for more content⁠⁠⁠⁠⁠⁠⁠ Bring confidence to your wealth building with simplified strategies from The Money Guy. Learn how to apply financial tactics that go beyond common sense and help you reach your money goals faster. Make your assets do the heavy lifting so you can quit worrying and start living a more fulfilled life. Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael Smith—Managing Partner and Founder, Emerald Advisors Michael Smith shares how a client-first philosophy, niche specialization, and independence helped Emerald Advisors grow from $385mm to more than $1B in assets. In Summary What happens when an advisor builds a business around client service rather than operational efficiency? Jason Diamond speaks with Michael Smith, Founder and Managing Partner of Emerald Advisors, about the path from a successful Merrill practice to an independent RIA that has grown from approximately $385mm to more than $1B in assets. Along the way, Michael shares the story of being told he was “overservicing” clients, why that moment became a catalyst for independence, and how a highly specialized service model fueled the firm's growth. Drawing on lessons from a 24-year Navy career, Michael offers a perspective on leadership, specialization, client care, and what it takes to build a durable business in today's wealth management landscape. The Storyline Growth is often viewed as the result of marketing, referrals, acquisitions, or scale. Michael Smith sees it differently. After building a successful practice at Merrill, Michael found himself at odds with the constraints of the traditional wirehouse model. What ultimately stood out wasn't compensation, technology, or platform capabilities. It was a philosophical difference around client service. When he was told he was spending too much time helping clients navigate tax planning, equity compensation, and other financial decisions outside the traditional scope of investment management, he began to question whether the model aligned with the way he wanted to serve families. That realization eventually led him to launch Emerald Advisors in late 2019. The firm started with roughly 85 clients and approximately $385mm in assets. Today, Emerald serves more than 225 families and oversees more than $1B in assets. Throughout the conversation, Michael reflects on the lessons learned from building an independent firm, developing a niche around concentrated stock positions and executive compensation, navigating custodial and technology decisions, and creating a culture rooted in accountability and service. Underlying it all is a simple belief: when firms become highly intentional about who they serve and how they serve them, growth often becomes the outcome rather than the objective. Topics Covered Merrill breakaways and independence Client service as a growth driver Building an RIA RIA growth and scalability Organic growth strategies Concentrated stock positions and equity compensation planning Ideal client personas and niche specialization Schwab and Fidelity custody relationships Advisor succession and enterprise value Navy leadership principles in wealth management The rise of mega RIAs Advisor technology and infrastructure > Download a transcript of this episode… Listen and Learn Highlights for Advisors Why did being accused of “overservicing” clients become a turning point? (08:15)Michael explains how a conversation with management revealed a deeper misalignment between his client-service philosophy and the wirehouse model. What does client service look like beyond portfolio management? (11:30)The discussion explores how tax planning, equity compensation guidance, and proactive coordination can deepen client relationships. Why can specialization accelerate growth? (15:45)Michael shares why serving a defined niche often creates stronger referrals, greater expertise, and clearer positioning. How has the RIA landscape evolved since 2019? (20:30)Michael reflects on the rise of mega RIAs, changing technology capabilities, and why he believes independent firms still have significant advantages. What role do custodians really play in an independent business? (23:15)Michael discusses his experience working with Schwab and Fidelity and why he views custodians as strategic partners rather than competitors. Is the wirehouse model still the right fit for some advisors? (26:45)The conversation challenges the assumption that independence is the best path for everyone and explores the realities of running a business. Does reaching $1 billion in assets actually change anything? (32:45)Michael offers a practical perspective on growth, success, and why asset milestones can be misleading. What can advisors learn from the “steamboat” philosophy? (37:15)Drawing on his Navy experience, Michael shares a leadership framework that continues to shape how he approaches business building and decision-making. Key Takeaways Exceptional client service can become a meaningful competitive advantage when it extends beyond investment management. Independence gave Michael the flexibility to build a service model that aligned with his philosophy rather than adapting his philosophy to fit the platform. Developing a niche around executive compensation and concentrated stock positions helped accelerate Emerald's growth. The ability to make technology, custodial, and operational decisions quickly remains a significant advantage for independent firms. Not every advisor should be independent. Running a business requires a different set of skills and responsibilities than serving clients alone. Growth milestones are useful, but they do not define success. Michael believes success existed long before Emerald reached $1 billion in assets. High-performing teams with a clear client focus often find that growth becomes a natural byproduct of execution. https://youtu.be/RjzsMcC2DnY Quotable Moments “I literally had to go back and Google the word overservicing.” “Servicing the client is the most important thing that we can do today.” “If you serve a niche and you're very good at that niche, that word gets around.” “Growth becomes the outcome.” FAQs Can an advisor really “over-service” clients? The discussion explores the tension between efficiency and depth of service. While some business models prioritize scale and consistency, others are built around solving a broader range of client problems. The right answer often depends on the advisor's philosophy and business model. Does specialization still matter in a relationship business? Michael argues that developing expertise in a specific area can accelerate growth by making referrals easier and helping advisors become known for solving a particular set of problems. What actually changes when an advisor becomes independent? Beyond economics, independence often creates more flexibility around client service, technology, processes, and business decisions. At the same time, advisors assume responsibility for running the business itself. Is full independence the right path for every advisor? No. Michael acknowledges that many advisors benefit from the structure, support, and resources available within traditional firms. Independence offers flexibility, but it also introduces complexity and responsibility. How should advisors think about the $1 billion milestone? Michael views asset milestones as useful benchmarks but not measures of success. In his view, business quality, client outcomes, and sustainability matter more than any specific asset number. What role does an ideal client persona play in growth? Rather than trying to serve everyone, Emerald built its business around a clearly defined client profile. Michael believes that focus improves service, creates operational consistency, and supports organic growth. How can advisors balance growth with client service? One of the central themes of the episode is that growth and service are not necessarily competing objectives. In some cases, a differentiated service model becomes the reason a business grows. The discussion explores the tension between efficiency and depth of service. While some business models prioritize scale and consistency, others are built around solving a broader range of client problems. The right answer often depends on the advisor's philosophy and business model. Michael argues that developing expertise in a specific area can accelerate growth by making referrals easier and helping advisors become known for solving a particular set of problems. Beyond economics, independence often creates more flexibility around client service, technology, processes, and business decisions. At the same time, advisors assume responsibility for running the business itself. No. Michael acknowledges that many advisors benefit from the structure, support, and resources available within traditional firms. Independence offers flexibility, but it also introduces complexity and responsibility. Michael views asset milestones as useful benchmarks but not measures of success. In his view, business quality, client outcomes, and sustainability matter more than any specific asset number. Rather than trying to serve everyone, Emerald built its business around a clearly defined client profile. Michael believes that focus improves service, creates operational consistency, and supports organic growth. One of the central themes of the episode is that growth and service are not necessarily competing objectives. In some cases, a differentiated service model becomes the reason a business grows. Related Resources The Transitioning Advisor's Lament: Things I Wish I Knew Before Freedom vs. Familiarity: Is it Worth Disrupting Comfort for Something That Might Be Better? IBD vs. RIA Revisited: Two Independent Pathways for Advisors to Consider Advisor Transition Report 2026 Guest Bio Michael Smith, CPWA® is the Founder and Managing Partner of Emerald Advisors, an independent wealth management firm overseeing more than $1 billion in assets for affluent families, executives, and business owners with complex planning needs. Mike entered the wealth management industry in 2005 after a distinguished 24-year career in the United States Navy, where he served both as an enlisted sailor in the Submarine Force and later as a Limited Duty Officer aboard USS Abraham Lincoln and on major staffs around the world. He earned a Bachelor of Science in Management and an MBA with dual emphases in Finance & Accounting and International Business. Throughout his career, Mike has been known for his commitment to comprehensive planning, helping clients navigate complex issues involving concentrated stock positions, executive compensation, tax strategy, estate planning, philanthropy, and multi-generational wealth transfer. His client-first approach and passion for education have helped Emerald Advisors grow from a startup firm in 2019 to a nationally recognized RIA serving more than 225 families. Outside of the office, Mike is an avid ultrarunner, golfer, lifelong learner, and dedicated advocate for children’s health initiatives. He is a current member of the Legacy Council at Seattle Children’s Hospital and has served in leadership and board roles supporting the Juvenile Diabetes Research Foundation, the Barbara Davis Center for Diabetes, the ALS Association, and the Alyssa Burnett Adult Life Center. He is also the proud father of Kat Smith. NOTE: The views and opinions expressed by the guests on this podcast are their own and do not necessarily reflect the views and opinions of Diamond Consultants. Neither Diamond Consultants nor the guests on this podcast are compensated in any way for their participation. View the transcript of this episode… From “Overservicing” Clients to Building a $1B RIA: A Merrill Breakaway Story A conversation with Jason Diamond and Michael Smith, Managing Partner and Founder of Emerald Advisors.      Jason Diamond: Welcome to the latest episode of our podcast series for financial advisors. Today’s episode is From “Overservicing” Clients to Building a $1B RIA: A Merrill Breakaway Story. It’s a conversation with Michael Smith, managing partner and founder of Emerald Advisors. I’m Jason Diamond and this is the Diamond Podcast for financial advisors. Mindy Diamond: At Diamond Consultants, we help elite advisors identify the right environment for their businesses to thrive whether that’s at a wirehouse, boutique or independent firm. With nearly three decades of experience, we’ve guided thousands of advisors and represented more than a quarter of a trillion dollars in assets transitioned and, each year, one in four advisors managing a billion dollars or more who change firms are our clients. Our process is education driven and based on building relationships starting as your strategic partner well before you’re even thinking of a move. To schedule a confidential conversation, call us at (908) 879-1002. Wondering why advisors change firms and where they’re headed? Are transition deals going up or down? Those very questions and more inspired us to create our annual advisor transition report. It’s the award-winning, data-driven resource designed for advisors that connects the dots between the motivations around movement and the firm’s appetite for top talent. Arm yourself with the knowledge you need to make smart decisions. Download your copy at diamond-consultants.com/transitionreport. Jason Diamond: Growth is often viewed as the result of better marketing, stronger referrals, a larger team and even acquisition and that’s all true yet growth can be the byproduct of something else entirely. For example, Michael Smith built a successful practice at Merrill then, one day, he was told he was spending too much time with his clients, or his management put it over-servicing clients. For Michael, that wasn’t a warning sign about his approach, it was a signal that he might have outgrown the firm and the model. Today, Michael is the founder and managing partner of Emerald Advisors, the independent RIA he launched in late 2019 with roughly 385 million in assets and 85 client relationships. Less than seven years later, the firm has grown to more than a billion in assets while remaining deeply focused on a highly-specialized client base and an unusually hands-on service model. What makes this story particularly interesting isn’t just the growth, it’s the thinking behind it. Michael’s perspective was shaped long before he entered wealth management. After serving more than two decades in the Navy, he brought a leadership philosophy centered on accountability, discipline and what he calls steamboat people, those who keep moving forward regardless of conditions, that mindset continues to influence how he builds his team, serves clients and evaluates opportunities. In this episode, we discuss the decision to leave Merrill, the realities of launching a fully independent RIA, why specialization can accelerate growth, the evolving role of custodians and technology and why he believes exceptional client service remains one of the industry’s most durable competitive advantages. Because Michael’s experience suggests that growth isn’t always the result of finding more opportunities, sometimes it’s the result of creating the freedom to execute the vision you already had so let’s jump in. Michael, thank you so much for joining us today. For starters, can you walk us through your background and what brought you to the world of wealth management? Michael Smith: Jason, thank you so much for the opportunity to be here today, I do listen to the podcast a lot especially before I left Mother Merrill. But my background and how I got into financial services is really distinct because I was on the board of JDRF back in the day and the national sponsor for JDRF was UBS PaineWebber and they’re like, “Mike, why don’t you be a financial advisor?” And my master’s degree was actually a finance and accounting in portfolio management because I’ve managed my own portfolio for years and years and so, when I couldn’t get a job, I just fell into it because I couldn’t get a job and I needed a job. That was 21 years ago, Memorial Day so that’s how I got into this industry. Jason Diamond: It’s a unique background, it’s super interesting and I want to talk more about it. You mentioned Mother Merrill, we’ll certainly get there. Before we do, give us a little bit of context on the current business you operate, Emerald Advisors, any context you can share on size, number of staff, types of clients you serve would be great. Michael Smith: Sure. So, we launched Emerald in 2019, November 2019 with about 85 clients and you always talk about this on the podcast how scared it is to launch and go independent. And I would say we took over about 95% of our clients that we wanted to bring over and today we’re at about 230 clients, I think we have some onboarding right now, we have just over a billion of assets. So, we launched with the 85 clients and around 350, 385 million, now we’re over a billion. Jason Diamond: Good for you. Michael Smith: Thank you. And I launched with four employees and we’re now at 11. And I would give a shout-out to one of my key employees because, when I launched, I actually hired somebody that had no experience with us and that was really a good thing because that allowed that person to really focus on operations and back office stuff while my business partner Emily and I were able to focus on bringing on the clients and alleviating any issues that they may have or thought. Jason Diamond: So, meaning you hired somebody basically immediately upon launch to help you with the transition and with this next chapter? Michael Smith: Correct. I hired them before but they started the day we launched. Jason Diamond: Brilliant, I love it. Oh, let’s definitely talk more about that because I think that’s a great strategy for … You’re right, you said it in a joking manner now because you’re seven years past but it’s a very real fear that advisors have and I think it’s worth talking more about. I want to mention too you have, obviously, built this business and grown this business dramatically. I don’t want to make this episode about the pandemic but you moved the business at a, certainly, a unique time. Did it impact your growth at all? Did you feel like you hit a brick wall? Just curious about your thoughts. Michael Smith: No, Jason, that’s a great observation. I would venture to say that the pandemic was actually a good thing for us. Jason Diamond: Interesting. Michael Smith: And I say that because, all of a sudden, you could hit pause because everyone was relearning how to do business, how do we do client reviews, how do we communicate with clients in a environment. So, I think the pandemic allowed us to just really reset our expectations visiting with clients because I used to fly a lot because I have clients in 38 different states so this has actually been, not just good for me, but good for the industry because I think it’s reset our expectations that we don’t have to be every day with a client facing. Jason Diamond: I agree with that largely and it’s true of our business too, by the way, it’s certainly reshaped the way people expect to be communicated with. I think Zoom has become much more mainstream, phone calls and we’ve heard from many other advisors who say something similar. I was just curious because you moved so close to or if there was an impact but I get, honestly, I think you’re right, it allowed you to have this nice natural inflection point and almost like flipping a switch of a clean slate. Michael Smith: It allowed us to learn the processes too. So, we launched in November 1st, by March we were in lockdown and so it gave us the opportunity to take several months of just learning the processes of how to be an RIA, it was pretty good. Jason Diamond: Absolutely. So, one of the things you mentioned in that was the way in which you serve clients and I’d read something funny and I think it was around the time of your move. You were talking about that, Merrill, you had a manager who spoke about that you would overserve your clients, you serve clients too much, tell me about that. Michael Smith: That was such an interesting topic because I got called down to the ops officer’s office and they’re like, “Ugh, Mike.” And it brought my admin down with me and they’re like, “Mike, these reports that you’re taking care of your clients too much,” and I’m like, “What do you mean?” “Well, you’re overservicing them.” Jason, I literally had to go back and Google the word overservicing because I was like, “How do you overservice the client? I’m not making their bed.” It was just so funny to me that I got counsel for overservicing clients when we’re in a client-facing job and I think that was part of the catalyst. Jason Diamond: Tell me more about what they meant, you think. Michael Smith: Hindsight, I think they … I like to take care of people which means I’m very intuitive towards taxes, I understand how the tax code works, I understand how everything impacts their bottom line. So, when we’re doing deferred comp enrollments or 401(k) enrollments or I’m a big believer in Roth 401(k)s and backdoor Roths and I’ve been doing them for years, I think what Mother Merrill wanted at that time was us not to do that. And, again, nothing against Merrill, I get it but this is how they wanted us to act and I wasn’t in that mold, I was taking care of clients to a much deeper depth is how I would say it. Jason Diamond: And I think that speaks to you outgrew the model not necessarily the firm. I think Merrill does a lot of things really well, you would agree with that, I think given that you built 85 clients and 350 million in assets is nothing to sneeze at. But the model that it seems like you value client service and an integrated client service experience of that and the wirehouse model oftentimes doesn’t put a premium on that. Tell me about your ethos or your thoughts around client service today and what being independent enables you to do. Michael Smith: So, that’s an interesting observation because one of my clients actually just mentioned to me that the reason we’re growing so much is because of our service model and the fact that we deliver a tremendous amount of value over just portfolio management. I said my managers is in portfolio management, I don’t do that any longer, I have a staff that handles that for me but it’s really the servicing of the clients because they don’t know what we know and I think servicing the client is the most important thing that we can do today. Jason Diamond: Give me some examples of what you mean by servicing the client in a more holistic way. I agree with you, by the way, portfolio management, table stakes, financial planning, table stakes, tell me more about what you mean. Michael Smith: By that I mean we do a quarterly review on tax. So, a lot of people don’t understand how taxes work and how estimated taxes work. So, estimated taxes are January 1st to March 31st, January 1st to May 31st, January 1st to August 31st, that’s how you do your estimated tax payments, you figure out what that is. And for compensated employees where they have RSUs that come in at different times of the year or different grants or exercise their options at a different time, that can affect their estimated tax liability and I’m not big on giving Uncle Sam any more money than they have to have until they need it. And then everyone doesn’t understand how the penalties and interest works on the IRS. And I’m big on the tax payments because that’s where we can add a lot of value for not a lot of time and we integrate it with our portfolio so we know what we’re doing with our gains. And I happen to reside in Washington State which has a long-term capital gains tax rate once you surpass about 270,000 of long-term capital gains. So, it’s super important for us to be aware of this and that’s how we service them. We also help them with their rebalancing of their 401(k)s, things that wirehouses cannot supposed to do, we are not supposed to be helping them with some of their aspects of life. Jason Diamond: Yup. That’s what I was alluding to earlier, it’s limitations on the model, not because they’re bad models, it’s just a different way, a different ethos around client service. You mentioned RSUs and corporate employees, I know that’s a niche you have is around concentrated stock positions and equity comp plans. I guess let me ask you two different questions around this. First of all, why that niche? Interested. And then, second of all, do you think a team needs to have a specialization to be competitive these days or do you think it’s okay just to be like, “My job is to be the best advisor and I want to service assets wherever those assets may come from?” Michael Smith: Another great observation. I’m going to address the niche first and foremost. I think, and I talked to R.J. Shook’s staff just recently, and having a niche gives you a specialization and it also accelerates your growth factor. If you serve a niche and you’re very good at that niche, then that word gets around. If you’re a jack of all trades, you can do lots of things but I don’t think you’re focused and you’re not hitting the right numbers that I like to see. And I think that would be my theme is the niche allows you to focus on a very specific type of ideal client, that’s a Schwab thing where you have an ideal client persona and our firm has an ideal client persona. As far as having the equity comp, I absolutely was one of the teams at Merrill Lynch that was equity compensation designated, I managed a couple of plans. My exposure to that, Jason, I haven’t thought about this in a very long time, came from UBS where I had team members that were colleagues that were associated with the Nextel Sprint plan. And I always thought that you’re taking care of the top executives but, really, my background being in the military was how do we take care of the troops, the troops, I call them sailors, and how do we educate those sailors. And one of the things I’ve always said in my entire career in the military and I still say to this day is 50% of every bonus or a promotion or something like that should go to long-term savings. So, I use that same mentality with RSUs, with stock options, with bonuses. Set that aside, let that grow because you’re not used to spending it and you will learn to spend what you make. Jason Diamond: I think that’s a great reason, it’s super smart and I love your explanation, it was a very simplistic way. Honestly, even I hadn’t thought about that around your niche, I think, becomes almost like a force multiplier for your own growth because it’s much easier to become the guy in X, Y, Z vertical than to be the guy in every financial advisor of America, across America. Let me ask you a follow-up question, you mentioned the ideal client persona. I spend a lot of time at our firm thinking about this as well, what does your ideal client persona look like. How do you think about an opportunity though that differs from that persona? So, it’s great. Obviously, everybody, it’s easy, you get somebody who’s your perfect prospect, they walk in the front door, sign me up. But when you get something that’s not down the fairway for you, is it just I evaluate it on a one-off basis or are you super disciplined to that approach because it’s who your firm is? Michael Smith: I truly haven’t given that a whole lot of thought but I will tell you how I would handle that because I am handling it with some one-offs. I like the opportunity because you’re stretching your brain in that you’re thinking about how somebody else is reacting so you’d never know. So, I like it from a learning perspective but I also know it comes with a lot of other baggage, I’ll call it baggage, because, all of a sudden, they want to short the market, they want to go long-short strategies. So, all of a sudden, they’re not in our niche and, all of a sudden, they’re taking a lot of time, they’re draining our time so I think you got to be very careful about what you wish for. And there’s a lot of great advisors out there that will walk circles around these topics that I’m like, “Okay, I would rather refer somebody so they get the right experience than give them the wrong experience.” Jason Diamond: I absolutely love that answer. The bow you just put on it, I think, is the appropriate way in my mind to put a bow. At the end of the day, wouldn’t you rather service somebody more optimally even if you don’t believe it’s yourself, I agree with that. I want to ask you one more point on the client service piece. I was playing around on your website and, on your service model, you have health as a component of the client experience of your diagram. Why do you think health matters in a financial context? Michael Smith: I always believed in a healthy mind and a healthy body will bring so much joy to you and I think health is just part of your persona. If you don’t take care of yourself and your body and your mind, then it doesn’t matter what I do, I think you got to start with health. So, I’m very big on the executive physicals, I routinely require all of our staff to have an annual physical. And, again, they’re young people but you got to have these annual … I live and breathe going to see a doctor every year to do my annual physical, not because I think I’m pretty good health, I still run, I do a lot of things but I think your life starts with being healthy. Jason Diamond: Yeah, it’s refreshing to hear that, no doubt. It’s funny to think about but 2019 is a long time ago now and, in RIA world, I almost think of it like dog years. You’ve been around the block now for a little while so I’m curious how have you seen this space change since you launched in 2019? Michael Smith: In 2019, I didn’t know what I was doing, I could barely get out a wet paper bag but I do think it’s changed dramatically. I would say the biggest thing I’ve seen in just the six and a half, almost seven years is the rise of the mega RIAs and how they’re going to shape the industry. Everyone talked about fee compression at Merrill Lynch. When I was at Merrill, we talked about fee compression, then they talked about robo-advisors and now they’re talking about artificial intelligence replacing advisors, I don’t believe that and I don’t think that’s going to happen in the RIA space. What I see the RIA space maturing is into these very big mega firms as well as these independent RIAs like myself that serve a very niche market where we can walk in our lane. The ability to transact today is so much easier as an RIA than it was at a wirehouse as well because we have instant access to technology. My military background, my Navy background says make a decision right, wrong or different, if you don’t like it afterwards or you get new data, course change. So, in our industry, we can change on a notice. I hired a tech firm last year, I didn’t like the experience nine months into it, guess what, they’re not coming back. So, I can do that but you can’t do that at the bigger firms and even the bigger mega firms would have a hard time navigating a change just like that on a dime. Jason Diamond: You bring up an interesting point. To the extent you face competition, do you find yourself competing more against traditional wirehouse type firms or RIAs like yourself, mega caps RIAs? Are your clients attuned to any of this? Michael Smith: That’s an observation I haven’t thought of either there, Jason. I would say I don’t feel that I have a … I know there’s competition out there but we have a growth issue more than we have anything else so I don’t … I can’t take on the clients that want to become my clients so I’m not competing with people too much. Jason Diamond: A capacity issue, you mean? Michael Smith: Yeah, I have a capacity issue. Jason Diamond: I think you’re not alone in that. How can I even think about competition and the like when … A lot of advisors would probably say that. I want to talk more about the capacity situation but, before I do, let’s talk a little more about the RIA setup. Who do you custody with, remind us, and why or how did you arrive at that decision? Michael Smith: Yeah. So, when I launched, I went with Schwab, Schwab is a phenomenal partner, they helped me get a lot of stuff done, I couldn’t have done it without Schwab. During the pandemic, I realized that I should probably … So, remember, during the pandemic, we had a lot of issues with the banking industry, it was almost like a financial crisis but in a very compressed time. So, during the COVID, I decided to add Fidelity as another custodian so now I have two custodians and I opened accounts on both sides of the house but I like the custodians that are there to help you, they’re very good at what they do. I don’t even consider them a competitor and they aren’t competitors, they have their own branch so I don’t consider them competitors, I think they’re my partners and both Charles Schwab and Fidelity are good partners. Jason Diamond: Yeah, I think that’s the healthy way to look at the custody relationship. That’s a very common approach, I think, is launching with one custodian and then adding a secondary custodian or a tertiary custodian down the line for one reason or another so I appreciate you sharing that because we get those types of nuts and bolts questions a lot so I figured I’d ask you. One last question on the setup and then we’ll shift gears. Has anything been a negative? So, you talked about leaving Mother Merrill behind and, Mother Merrill, we use it facetiously but obviously it implies a degree of comfort and the homeland so I’m curious if you miss anything. Michael Smith: I miss the camaraderie of being with a bunch of other folks. I mentioned this when I first launched, I mentioned it year over year with my team, the one thing that we miss as an RIA and, again, Dynasty has their benefits as well and the mega RIAs have their benefits but, if you’re a true independent like myself, we get to go to conferences that we want to and that’s a timing issue, really, a time constraint. But one thing Merrill and Morgan, JPMorgan, and the other big wirehouses have as well as the megas, they have the ability to put conferences together for their advisors or their administrators and have this education. That’s the one thing that, I think, would evolve in the RIA industry in the future as well. They’re not my competitors, they’re my business colleagues. And if we think of them as competitors, and a lot of people do because I don’t want to share my client information or what I do with my competitor because they may steal them, if you’re that insecure, then you’re probably not the right advisor in the first place. Jason Diamond: I don’t disagree with that. It’s interesting too, I hear two common answers to that question, not about Merrill but just about somebody who’s broken away, what do you miss about the captive firm world. Either on this podcast or just in conversations with advisors, brand comes up a lot and then the point you just raised. I’ll even hear like, “Hey, forget the conferences and the trainings, just being able to have an office where I’ve got eight other advisors on a row for me, it’s a little bit of a different setup than in the independent space,” and I think that’s just a reality of you take the good with the bad. And for other advisors, by the way, one of the things I want to ask you about to this point is do you believe that there are advisors that are just better served in the W2 traditional firm world or do you think that every advisor should be looking at the RIA space? Michael Smith: I think that wirehouse serves a great purpose and- Jason Diamond: Okay, me too. Michael Smith: … there’s a lot of great people that are great advisors in that wirehouse, they need the structure. What I hadn’t alluded to is, and I mentioned this to a former manager from Merrill Lynch of mine just recently, actually, I was like, “I don’t think advisors realize what it takes to run a business.” I’m not trying to sugarcoat it, running an RIA is hard work, it takes a lot of your time day in and day out to run a business as well as taking care of and servicing your clients so I do think the wirehouse venue is the right way to go. And, Jason, I want to go back to one other thing about your identity. I launched as the Smith Group because that’s what I was known at Merrill Lynch. Within three or four months, I changed that name to a firm because I did not want to be associated with it. So, when you’re at one of the wirehouses, you’re known as your team name or something of that sort, I didn’t want to be known as that, I wanted to be known as Emerald Advisors not the Smith Group because, all of a sudden, you have a single point of failure. So, brand identity, it’s not so unique inside the wirehouse because it’s a team name versus Merrill or Morgan Stanley or something like that. Jason Diamond: It’s a good segue because I’ll tell you where my mind goes when you bring that up. My mind goes is you’re smart in a way that you might not even realize or maybe you do realize which is that, if and when it ever comes time to sell this business, it is probably more valuable without your name attached to it or maybe not. But in some way, shape or form, as an RIA, you have an obligation to be thinking about that or it’s probably on your radar, maybe not an obligation. Have you given an ounce of thought to M&A either acquiring businesses, growing in that way or, ultimately, when you succeed out of this business and what the RIA space enables you to do? Michael Smith: To answer that question, yes. Everyone’s thinking about merger and acquisition, I think about succession planning from day one. I actually thought about I’m a big team person, I come from the submarine force where everyone is a key player on a submarine, every single person has a job and responsibility on a nuclear submarine. So, inside the financial services industry, I know Merrill Lynch was very big on teaming, I understand Morgan Stanley is as well because teaming gives them a breadth of responsibility where the responsibilities are shared. So, mergers and acquisitions or selling my business, I think, if you’re not thinking about that … And I’m not thinking about selling my business because that’s a distraction to me. If I needed the money, then I would’ve went to a wirehouse and that’s okay, you monetize your life’s work. Today, I’m all about what’s right for the client, what’s right for my team and what’s right for where I want to be in the next 10 to 20 years. So, I am growing, I do want to grow, I’m looking at opening offices in probably three locations in the next 24 months or so. Jason Diamond: Well, that’s what I was going to say, plenty of advisors I think would say the same, I have a lot of runway. But what about the other side of this equation which is you’ve had tremendous organic growth, you’ve tripled your client base, you’ve more than tripled the asset base, have you thought about acquisition as a mean to jet fuel the inorganic growth side of things? Michael Smith: I have but not in the typical sense that you’re looking at as buying a book of business. I want to partner with like-minded advisors that share that common thread of taking care of clients where you can serve as their trusted counsel and sit in the meetings with their attorneys and sit in the meetings with the accountants and give them sage counsel that you can only do because you’ve been with the family for 20 years. You know this family and that, not always, but I think that’s missed a lot in other firms. Jason Diamond: Yeah, I think that’s fair. I just thought of something else that you brought up. You brought Dynasty so I’m going to ask … I’m going to pull on this thread. That implies to me that you’re at least loosely aware of the supportive independence models that are out there yet you chose a very independent, autonomous path, why? Michael Smith: Because I didn’t know what I was doing. Jason Diamond: Fair. Michael Smith: Let’s be honest, I like Dynasty, I talked with Dynasty when I left. I talked to them all, I talked to Rockefeller, I talked to Morgan, I talked to Dynasty and then, when push came to shove, I wanted to be Mike Smith and launch my own firm and learn. And I will tell you, you learn drinking through a fire hose and we did that, we learned, I know the mistakes. What I didn’t want to do is just go to someplace where this is the stuff you’re going to have to use. So, I think Dynasty is a great launching platform, I think there’s other ones out there that are similar to Dynasty or the Rockefellers or the Morgans, it’s truly what you’re trying to achieve in life. What do you want for you and your clients and I always put my clients before me because I’ve always had this lifelong thing of, you do the right thing, you’re going to get taken care of. Jason Diamond: Yeah. And that’s a very common analysis, by the way, and it’s very common too for big advisors like yourself to say I did my homework across all of those different categories. I looked at the traditional wirehouses and regional firms and boutique firms, I looked at the independent broker dealers, I looked at the support platforms and the aggregators and the roll-ups and here’s ultimately what I landed on and why. Did you always know that though or was that something that it took you a diligence process to figure out? There was plenty of advisors, by the way, who come to us and they’re like, “I knew for the last five years that I was sitting there I was launching an RIA someday.” Michael Smith: Yeah. I did not know that and, to be honest with you, hindsight, I think one of those partners probably could have made me a little bit better at first because then I could have focused on clients versus focusing on, hey, how to open a business, who’s your technology … We talked about custodians and some other things but we didn’t talk about technology, how do you go find that technology. Where’s your email address come from? Who’s your chief compliance officer? When it resides on you, you got to look in the mirror. So, I think those parties out there that provide that for brand-new advisors launching could be very beneficial. I had in my mind what I needed to do and I knew I’m very frugal so mine boiled down to how much money I wanted to spend, to be honest with you. Jason Diamond: I think it is a cost benefit analysis, it is. It’s absolutely … Because if you list the functions of a support platform on paper and you showed it to somebody who didn’t know the industry, they would say, “Why on earth wouldn’t you do this? They’re taking off your plate compliance and tech and custody and the like,” and the answer is because there’s a cost associated with it and plenty of advisors decide what you decide, I wanted … Or I just wanted a greater degree of autonomy and freedom, to your point, the name on the door piece, I wanted this to be mine. Michael Smith: And, Jason, I think it also goes to the uncertainty. I had never done anything since Navy, financial advising and then launching. So, for me, I was launching with four employees I had to take care of and here I was going to hire a third party that I was going to have to spend X amount on and I didn’t even know what my income was going to be. That’s different if you’re a multi-billion dollar FA coming out of a wirehouse, the monetary dynamics are different. Jason Diamond: Agreed. Okay, here’s a good one for you. We get this concept from advisors, from firms, from private equity that a billion dollars in assets is like this magic number in our industry. Do you feel like anything’s changed now that you’re at a billion and what’s the next chapter for Emerald Advisors? Is it just continuing on this steady trajectory and serving clients and trust that everything else comes with that? Michael Smith: I go back and forth on a billion, everyone thinks that’s the right number, the biggest number that you need but I think it’s just an arbitrary numbers because it didn’t define who I was. And a lot of people define success at a billion, they define success that you’re a successful firm at a billion. I think I was a successful firm at 300 million, I was a successful financial advisor with 20 clients in 2005. I would say a billion is a multiplier, what I would tell new advisors out there today is gather assets. The more assets you have, the more revenue you generate. The more revenue you generate, the more money you can put in your pocket which means the longer you can stay in the industry. The problem with the industry is an attrition problem, not anything else. So, assets just give us the ability to have revenue which gives us the ability to grow. Jason Diamond: And is that the plan? Keep adding assets, keep growing one client at a time with the focus though, obviously, on what makes you which is a very client-centric service model. Michael Smith: Correct. There’s a lot of things I want to do in the next couple of years and expanding our footprint is our biggest one with the right partners and then just keep adding. I have a business development officer that I’m probably offer a job to here pretty soon and things are going well. Jason Diamond: Yeah, that’s great. You mentioned the tech stack and the other components of the business and I hear you on the frugal cost-benefit analysis. But who did you turn to for some of those early decisions, was it Schwab primarily who helped hold your hand through that? Michael Smith: Schwab was very good at helping me identify the tech stack at first and the tech stack is actually the one consistent, there’s a lot of things I’ve been consistent on but tech is one that I’ve stayed with them. I launched with RightSize, now they’re Advisory, they’re very good, they do the right job for us and I’m big on cybersecurity. So, tech was helpful from Schwab, Schwab helped us with that. Jason Diamond: So, we spoke a little bit about your naval experience but, I’m curious, can you tell us how has your naval experience shaped your perception or your experience in wealth management? Michael Smith: My Navy path was a lot different than many officers. I served 12 years as an enlisted person before I got my direct commission as a Mustang officer, typically called limited duty officers or loud, dumb and obnoxious as I like to say. But that experience gave me a unique perspective because I was able to be the enlisted side and officer which are the workers and then the management side so I had both experiences which was unique. When I was commissioned, Admiral Jerry Ellis, a submarine admiral that commissioned me, heard this lesson to the podium, he was just talking about me in this point but he said, “There are three kinds of people in every organization. You have rowboat people who need to be pushed, you have sailboat people who move whenever the conditions are favorable and then there’s steamboat people, they move continuously through calm or storm.” And he said, “This is Ensign Michael Smith,” he said, “Make your course.” And that’s always stood with me because you do have those three types of people in life. You got people that are just … They’re robo people, they go until they get tired. You got sailboat people that go wherever the wind blows them and then you got steamboat people that chart their own course. I would say for advisors out there make your course or just be happy with what you’re doing. But for some of us hard chargers, I think that analogy has stayed with me my entire career. Jason Diamond: It’s fantastic. I love the analogy, great naval tie in also. Thanks for sharing that. We got time for one more question. You have a fascinating background, a fascinating path to the industry, obviously, an incredibly disciplined approach around client service, any parting thoughts, words of wisdom especially as it relates to growth? That’s what strikes me most about your story is the growth that your move unlocked and that’s what every advisor who listens to our show is looking for. Michael Smith: I’m going to give another plug to Schwab on this. We actually were fortunate and I got their consulting group to come in right afterwards and I’m a big believer in having offsite. So, I’ve had an offsite, two offsites a year for my team and it’s the entire team unlike the wirehouses where you don’t take your admins and stuff like that. I take my entire team to an offsite and we group up on what we’re trying to achieve and have goals and objectives for the year. Schwab allowed us to use their consultants and we came up with our ideal client persona. Teams or firms that have this model become high performing. When you become high performing, growth becomes the outcome. I couldn’t do anything but grow. Jason, I couldn’t not grow because I had this ideal client persona, I knew how I was going to do it, it was measurable. So, growth becomes the outcome and, if you hold people responsible, then we’re all going to grow together and it’s a fun outcome. Jason Diamond: Fantastic, it’s a great place to end. Thank you so much for sharing your expertise with us, I can’t wait to see what the next chapter holds for Emerald, this has been a lot of fun. Michael Smith: Jason, thank you so much. I appreciate everything you do for the industry as well. Mindy Diamond: As a financial advisor, you hold yourself to the highest standards of integrity, honesty and credibility. You are successful because you take your professional responsibility seriously and are dedicated to your clients. But are you living your best business life? Are your goals aligned with your firms or could a better option exist? Should I Stay or Should I Go? Is a book written with you in mind? It’s a self-guided journey that walks you through the key steps that we take with our advisor clients. This strategic thought process and roadmap to professional self-discovery is designed to help you ask the right questions and think critically and objectively whether you’re considering change or not. Learn how to get your copy at diamond-consultants.com/thebook. From “Overservicing” Clients to Building a $1B RIA: A Merrill Breakaway Story A conversation with Jason Diamond and Michael Smith, Managing Partner and Founder of Emerald Advisors.      Jason Diamond: Welcome to the latest episode of our podcast series for financial advisors. Today’s episode is From “Overservicing” Clients to Building a $1B RIA: A Merrill Breakaway Story. It’s a conversation with Michael Smith, managing partner and founder of Emerald Advisors. I’m Jason Diamond and this is the Diamond Podcast for financial advisors. Mindy Diamond: At Diamond Consultants, we help elite advisors identify the right environment for their businesses to thrive whether that’s at a wirehouse, boutique or independent firm. With nearly three decades of experience, we’ve guided thousands of advisors and represented more than a quarter of a trillion dollars in assets transitioned and, each year, one in four advisors managing a billion dollars or more who change firms are our clients. Our process is education driven and based on building relationships starting as your strategic partner well before you’re even thinking of a move. To schedule a confidential conversation, call us at (908) 879-1002. Wondering why advisors change firms and where they’re headed? Are transition deals going up or down? Those very questions and more inspired us to create our annual advisor transition report. It’s the award-winning, data-driven resource designed for advisors that connects the dots between the motivations around movement and the firm’s appetite for top talent. Arm yourself with the knowledge you need to make smart decisions. Download your copy at diamond-consultants.com/transitionreport. Jason Diamond: Growth is often viewed as the result of better marketing, stronger referrals, a larger team and even acquisition and that’s all true yet growth can be the byproduct of something else entirely. For example, Michael Smith built a successful practice at Merrill then, one day, he was told he was spending too much time with his clients, or his management put it over-servicing clients. For Michael, that wasn’t a warning sign about his approach, it was a signal that he might have outgrown the firm and the model. Today, Michael is the founder and managing partner of Emerald Advisors, the independent RIA he launched in late 2019 with roughly 385 million in assets and 85 client relationships. Less than seven years later, the firm has grown to more than a billion in assets while remaining deeply focused on a highly-specialized client base and an unusually hands-on service model. What makes this story particularly interesting isn’t just the growth, it’s the thinking behind it. Michael’s perspective was shaped long before he entered wealth management. After serving more than two decades in the Navy, he brought a leadership philosophy centered on accountability, discipline and what he calls steamboat people, those who keep moving forward regardless of conditions, that mindset continues to influence how he builds his team, serves clients and evaluates opportunities. In this episode, we discuss the decision to leave Merrill, the realities of launching a fully independent RIA, why specialization can accelerate growth, the evolving role of custodians and technology and why he believes exceptional client service remains one of the industry’s most durable competitive advantages. Because Michael’s experience suggests that growth isn’t always the result of finding more opportunities, sometimes it’s the result of creating the freedom to execute the vision you already had so let’s jump in. Michael, thank you so much for joining us today. For starters, can you walk us through your background and what brought you to the world of wealth management? Michael Smith: Jason, thank you so much for the opportunity to be here today, I do listen to the podcast a lot especially before I left Mother Merrill. But my background and how I got into financial services is really distinct because I was on the board of JDRF back in the day and the national sponsor for JDRF was UBS PaineWebber and they’re like, “Mike, why don’t you be a financial advisor?” And my master’s degree was actually a finance and accounting in portfolio management because I’ve managed my own portfolio for years and years and so, when I couldn’t get a job, I just fell into it because I couldn’t get a job and I needed a job. That was 21 years ago, Memorial Day so that’s how I got into this industry. Jason Diamond: It’s a unique background, it’s super interesting and I want to talk more about it. You mentioned Mother Merrill, we’ll certainly get there. Before we do, give us a little bit of context on the current business you operate, Emerald Advisors, any context you can share on size, number of staff, types of clients you serve would be great. Michael Smith: Sure. So, we launched Emerald in 2019, November 2019 with about 85 clients and you always talk about this on the podcast how scared it is to launch and go independent. And I would say we took over about 95% of our clients that we wanted to bring over and today we’re at about 230 clients, I think we have some onboarding right now, we have just over a billion of assets. So, we launched with the 85 clients and around 350, 385 million, now we’re over a billion. Jason Diamond: Good for you. Michael Smith: Thank you. And I launched with four employees and we’re now at 11. And I would give a shout-out to one of my key employees because, when I launched, I actually hired somebody that had no experience with us and that was really a good thing because that allowed that person to really focus on operations and back office stuff while my business partner Emily and I were able to focus on bringing on the clients and alleviating any issues that they may have or thought. Jason Diamond: So, meaning you hired somebody basically immediately upon launch to help you with the transition and with this next chapter? Michael Smith: Correct. I hired them before but they started the day we launched. Jason Diamond: Brilliant, I love it. Oh, let’s definitely talk more about that because I think that’s a great strategy for … You’re right, you said it in a joking manner now because you’re seven years past but it’s a very real fear that advisors have and I think it’s worth talking more about. I want to mention too you have, obviously, built this business and grown this business dramatically. I don’t want to make this episode about the pandemic but you moved the business at a, certainly, a unique time. Did it impact your growth at all? Did you feel like you hit a brick wall? Just curious about your thoughts. Michael Smith: No, Jason, that’s a great observation. I would venture to say that the pandemic was actually a good thing for us. Jason Diamond: Interesting. Michael Smith: And I say that because, all of a sudden, you could hit pause because everyone was relearning how to do business, how do we do client reviews, how do we communicate with clients in a environment. So, I think the pandemic allowed us to just really reset our expectations visiting with clients because I used to fly a lot because I have clients in 38 different states so this has actually been, not just good for me, but good for the industry because I think it’s reset our expectations that we don’t have to be every day with a client facing. Jason Diamond: I agree with that largely and it’s true of our business too, by the way, it’s certainly reshaped the way people expect to be communicated with. I think Zoom has become much more mainstream, phone calls and we’ve heard from many other advisors who say something similar. I was just curious because you moved so close to or if there was an impact but I get, honestly, I think you’re right, it allowed you to have this nice natural inflection point and almost like flipping a switch of a clean slate. Michael Smith: It allowed us to learn the processes too. So, we launched in November 1st, by March we were in lockdown and so it gave us the opportunity to take several months of just learning the processes of how to be an RIA, it was pretty good. Jason Diamond: Absolutely. So, one of the things you mentioned in that was the way in which you serve clients and I’d read something funny and I think it was around the time of your move. You were talking about that, Merrill, you had a manager who spoke about that you would overserve your clients, you serve clients too much, tell me about that. Michael Smith: That was such an interesting topic because I got called down to the ops officer’s office and they’re like, “Ugh, Mike.” And it brought my admin down with me and they’re like, “Mike, these reports that you’re taking care of your clients too much,” and I’m like, “What do you mean?” “Well, you’re overservicing them.” Jason, I literally had to go back and Google the word overservicing because I was like, “How do you overservice the client? I’m not making their bed.” It was just so funny to me that I got counsel for overservicing clients when we’re in a client-facing job and I think that was part of the catalyst. Jason Diamond: Tell me more about what they meant, you think. Michael Smith: Hindsight, I think they … I like to take care of people which means I’m very intuitive towards taxes, I understand how the tax code works, I understand how everything impacts their bottom line. So, when we’re doing deferred comp enrollments or 401(k) enrollments or I’m a big believer in Roth 401(k)s and backdoor Roths and I’ve been doing them for years, I think what Mother Merrill wanted at that time was us not to do that. And, again, nothing against Merrill, I get it but this is how they wanted us to act and I wasn’t in that mold, I was taking care of clients to a much deeper depth is how I would say it. Jason Diamond: And I think that speaks to you outgrew the model not necessarily the firm. I think Merrill does a lot of things really well, you would agree with that, I think given that you built 85 clients and 350 million in assets is nothing to sneeze at. But the model that it seems like you value client service and an integrated client service experience of that and the wirehouse model oftentimes doesn’t put a premium on that. Tell me about your ethos or your thoughts around client service today and what being independent enables you to do. Michael Smith: So, that’s an interesting observation because one of my clients actually just mentioned to me that the reason we’re growing so much is because of our service model and the fact that we deliver a tremendous amount of value over just portfolio management. I said my managers is in portfolio management, I don’t do that any longer, I have a staff that handles that for me but it’s really the servicing of the clients because they don’t know what we know and I think servicing the client is the most important thing that we can do today. Jason Diamond: Give me some examples of what you mean by servicing the client in a more holistic way. I agree with you, by the way, portfolio management, table stakes, financial planning, table stakes, tell me more about what you mean. Michael Smith: By that I mean we do a quarterly review on tax. So, a lot of people don’t understand how taxes work and how estimated taxes work. So, estimated taxes are January 1st to March 31st, January 1st to May 31st, January 1st to August 31st, that’s how you do your estimated tax payments, you figure out what that is. And for compensated employees where they have RSUs that come in at different times of the year or different grants or exercise their options at a different time, that can affect their estimated tax liability and I’m not big on giving Uncle Sam any more money than they have to have until they need it. And then everyone doesn’t understand how the penalties and interest works on the IRS. And I’m big on the tax payments because that’s where we can add a lot of value for not a lot of time and we integrate it with our portfolio so we know what we’re doing with our gains. And I happen to reside in Washington State which has a long-term capital gains tax rate once you surpass about 270,000 of long-term capital gains. So, it’s super important for us to be aware of this and that’s how we service them. We also help them with their rebalancing of their 401(k)s, things that wirehouses cannot supposed to do, we are not supposed to be helping them with some of their aspects of life. Jason Diamond: Yup. That’s what I was alluding to earlier, it’s limitations on the model, not because they’re bad models, it’s just a different way, a different ethos around client service. You mentioned RSUs and corporate employees, I know that’s a niche you have is around concentrated stock positions and equity comp plans. I guess let me ask you two different questions around this. First of all, why that niche? Interested. And then, second of all, do you think

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Rylan Foltz went from JP Morgan analyst to independent wealth advisor to co-founding WealthFeed — a marketing and prospecting platform helping financial advisors find better clients faster using predictive analytics and behavioral data. In this episode, Rylan walks through the full arc of that journey and unpacks the strategic decisions that took WealthFeed from zero to thousands of advisors in just two years.Jeff and Rylan dig into why the wealth management industry is so underserved by marketing technology, the power of building bottom-up before going enterprise, how to make a SaaS product genuinely sticky in a regulated industry, and why your distribution moat matters more than your product moat in an era where anyone can spin up a competing product overnight.Whether you're a first-time founder trying to crack product-market fit, or a scaling SaaS leader thinking through enterprise sales cycles, pricing strategy, and team-building, this episode delivers actionable insight on all fronts.Key Takeaways3:47 — The Origin of WealthFeed Rylan realized as a practicing advisor that organic growth was the hardest part of the job — and that the wealth management industry had almost no structured approach to marketing. That gap became the business.6:15 — Why Finance Is Marketing's Last Frontier Advisors can name the big firms but not their local competitors. The industry is dominated by aging, lifestyle-mode advisors who stopped teaching growth tactics — leaving a giant opportunity for a niche marketing platform.10:39 — What's Old Is New Again WealthFeed offers machine-written handwritten notes that look like wedding invitations. In a world saturated with digital communication, old-school physical outreach is standing out again.11:22 — Stop Thinking Leads, Start Building Assets Advisors shouldn't buy leads — they should build a database audience the way Budweiser buys Super Bowl ads: consistent, compounding, ROI over time.13:01 — Niche Marketing Builds Trust Generic messaging ("I help with retirement planning") signals you don't know your prospect. Hyper-specific messaging ("I work exclusively with SaaS co-founders on RSUs and equity comp") creates immediate trust and relevance.14:12 — The All-in-One Platform Advantage WealthFeed layers CRM, outbound marketing (LinkedIn, email, direct mail, handwritten notes), and proprietary data into one workflow — so advisors don't stitch together five point solutions.17:41 — Simplicity Over Power at Launch Early on, feature overload slowed adoption. The lesson: launch with one compelling use case (for WealthFeed, inheritance lead data), get users in the door, then upsell from there.20:55 — Your Moat Is Your Distribution AI lets anyone copy a product in a weekend. What can't be copied overnight is your relationships, your user base, and the custom integrations you've built into a customer's workflow.25:03 — Bottom-Up Enterprise Strategy WealthFeed got traction by signing individual advisors first, letting the grassroots demand bubble up to management — which created enterprise deals without having to wait in long procurement queues.27:09 — Don't Hunt Elephants Until You Can Afford To Enterprise deals can drag for three years. Without revenue from individual and SMB customers, a startup can starve waiting for that one big contract to close.29:28 — Hybrid Pricing: Access Fee + Usage Credits Flat subscriptions don't work when one advisor sends 20,000 handwritten notes and another logs in once a month. A hybrid model lets you charge for scale without penalizing light users.31:28 — Price High, Discount Down Starting low and raising prices creates churn and resentment. Starting at a premium and offering a promotional discount sets expectations — customers know the real value from day one.33:19 — Balancing Founder Vision vs. Customer Feedback A 50/50 split: take customer input seriously, but don't become a yes-man. The most successful founders — especially those who've lived the problem — trust their forward vision even when customers can't yet see it.35:59 — Build Infrastructure Before You're Drowning WealthFeed hired sales, dev, and customer success earlier than felt necessary. That foundation is now why their customer success "outperforms anyone else in the industry."38:30 — Flatten the Org to Connect Dev and Customer Tech teams that never see how the product is used build the wrong things. WealthFeed has engineers sit in on sales calls so they understand why features matter, not just what to build.39:45 — Let Compliance Work With You, Not Against You Instead of pitching firms on new compliance workflows, WealthFeed integrates into whatever compliance process already exists — dramatically speeding up enterprise approvals.Tweetable Quotes"Your moat is your distribution. Go-to-market has gotten extremely valuable because you could almost create the product overnight." — Rylan Foltz"Stop thinking about leads. Start thinking about building an audience, a database, an asset for life." — Rylan Foltz"No one wants a generalist. Everyone wants the best knee surgeon in the country. As an advisor, you've got to become really niche-focused." — Rylan Foltz"Start your pricing high. You can always discount down. It's really hard to raise prices." — Rylan Foltz"It's easier to sell one flavor of ice cream and say it's the best than to offer 32 flavors and create option overload." — Rylan Foltz"What's old is new. Everything shifted to digital, so old-school processes are how you stand out now." — Rylan Foltz"You'll be most successful solving a problem you personally went through. It comes across in your sales, your fundraising, everything." — Rylan Foltz"Don't get too caught up in enterprise until you build up the user base. Get revenue first, then you can afford to chase the elephants." — Rylan FoltzSaaS Leadership Lessons1. Niche down relentlessly — and mean it. Rylan didn't just say "we focus on financial advisors." WealthFeed built every feature, every data layer, and every compliance workflow around that single ICP. The more specific your niche, the stronger your trust signal, the better your retention, and the harder you are to displace. Generalist products get commoditized. Specialists get embedded.2. Distribution is the real product. In a world where a working SaaS product can be replicated in a weekend, your go-to-market is your most defensible asset. Relationships, user base saturation within target firms, custom integrations, and compliance workflow ownership are what prevent a competitor from walking in and saying "we do the same thing." Build distribution as intentionally as you build product.3. Start simple — layer complexity after adoption. Feature-rich doesn't mean better. WealthFeed launched with one use case (inheritance lead data) and expanded from there. Getting a user in the door on one powerful idea is vastly easier than selling a full platform. Upselling to an existing user is far more efficient than converting a prospect who's overwhelmed at first glance.4. Build your team infrastructure earlier than you think you need it. Founders often hire only when they're already underwater. Rylan and his team built out sales, dev, and customer success before they felt the pressure — and that head start compounded into top-tier customer outcomes. Infrastructure built under stress tends to crack. Infrastructure built with intention scales.5. Price to your value, then offer strategic discounts. Starting low might feel like a growth hack, but it sets a price anchor that's almost impossible to raise without friction. Starting at a premium gives you room to discount strategically, run promos, and still maintain perceived value. Customers who came in knowing the "real" price won't balk at renewal the way customers who got a surprise price hike will.6. Close the gap between your builders and your buyers. One of WealthFeed's most impactful structural choices: having engineers sit in on sales calls. When the people building the product understand how it's actually used — and why it matters — they build better, faster, and with more empathy. Kill the wall between tech and go-to-market. Your roadmap will thank you.Guest Resourcesrylan@wealthfeed.comhttps://www.wealthfeed.com/https://www.linkedin.com/in/rylanfolts/Episode SponsorThe Futureproof Series - https://www.youtube.com/playlist?list=PLfkXKUPZ5xuOqMPR7_gzGybncTtavyR1NThe Captain's KeysSmall Fish, Big Pond – https://smallfishbigpond.com/ Use the promo code ‘SaaSFuel'Champion Leadership Group –

Most people plan their retirement like they control the date. The data says they don't. A new Society of Actuaries study found that 59% of retirees stopped working earlier than expected -- and for most of them, the decision wasn't theirs. Health setbacks, job loss, caregiving demands, and plain old job dissatisfaction all showed up before the spreadsheet said it was time. Joe and OG dig into what the numbers actually mean, who's most at risk, and the specific steps that create real flexibility before retirement finds you. OG and Anna follow with a full walkthrough of equity compensation -- RSUs, ESPPs, and stock options -- including the tax surprise that catches most people off guard.What You'll Walk Away WithWhy 59% of retirees left the workforce earlier than they planned -- and why only 6% left laterThe income gap nobody talks about: how high earners retire early mostly because they wanted to, while lower earners are pushed out by health and job lossWhy Coast FIRE math falls apart the moment your income stream stops before you planned -- and what that means for how aggressively you should be saving right nowThe one manager change that can end a 20-year career overnight -- and why keeping your network warm is one of the most underrated retirement prep moves availableThe 30-year mortgage paid like a 15-year analogy: why building financial margin now means retirement can happen on your terms, not someone else'sHow to prepare for the emotional side of early retirement -- including the identity shift, the relationship changes, and the pent-up demand that makes the first year unexpectedly wildRSUs versus stock options versus ESPPs: what each one actually means, how they're taxed differently, and why getting a grant without a strategy is the most expensive mistake in equity compThe 5-10% concentration rule: how much of your net worth should be tied to company stock -- and why your paycheck counts in that mathThe RSU tax trap: why your company withholds at 22% but you might actually owe 37% -- and why spending all your RSU money on a pool before April is a terrible ideaStacker Kiki's accountability letter: the complete list of what she's cutting, what she refuses to cut, and why the gamification of frugality is more powerful than white-knuckling itWhy This Matters NowYou may not get to choose your retirement date. But you do get to choose how prepared you are for the day it arrives. The people in this study who retired early by choice had one thing in common: they'd built enough margin that the choice was actually theirs.From the BasementJoe and OG dig into a USA Today piece on the surprising frequency of unplanned early retirement -- and what to do about it before the decision gets made for you. OG and Anna deliver episode five of their financial basics series with a full equity compensation walkthrough, including the tax withholding gap that sends people to April with surprise bills. Doug arrives with Mickey Mantle trivia. A community poll on how often Stackers check their portfolios during headlines produces results that are more honest than most people expected. Stacker Kiki writes a detailed letter about her intentional spending cuts, and OG quietly admits he's been burning through hotel shampoo samples all year.Resources MentionedSociety of Actuaries Retirement Risks Survey -- released May 2026; linked at stackingbenjamins.comUSA Today -- "Most of Us Retire Earlier Than Planned. Here Are the Top Reasons." by Daniel DeVise; linked at stackingbenjamins.comStacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguideStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201; Kevin Bailey's hot take on this week's pieceStacking Benjamins YouTube channel -- full OG and Anna equity comp series; youtube.com/stackingbenjaminsStacking Benjamins BAD Groups -- meetups in Boston, Seattle, Twin Cities, Mankato, Tucson, and more; stackingbenjamins.com/badStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle a critical question for investors: what happens if the next decade of market returns doesn’t cooperate—and does your financial plan rely on strong returns just to survive? They break down how to properly stress test your retirement plan using real-world scenarios, Monte Carlo analysis, and the importance of separating must-have expenses from discretionary spending to weather any environment. Plus, they dive into the hidden complexities of restricted stock units (RSUs), including how they’re taxed, vesting schedules, and why they should be treated as a concentrated position in your portfolio. You’ll also hear strategies for protecting your retirement timing from market downturns, how to think through pension lump sum versus income decisions, and smart ways to gift money for major life events without triggering unnecessary taxes.See omnystudio.com/listener for privacy information.

Neil Dutta is Head of Economic Research at Renaissance Macro Research (renMac). He leads their macroeconomic research efforts, with an emphasis on analysing the US economy, the Federal Reserve, global trends, and cross-market investment themes. He is considered a market economist, looking at the economic data and trying to highlight the risks to the consensus as he sees them.  Prior to RenMac, Neil spent seven years at Bank of America-Merrill Lynch. There, he was a Senior Economist covering both the United States and Canada. In this podcast, we discuss: Neil's Wall Street "Origin Story" The Four Pillars of Economic Analysis The Real Income Squeeze AI, RSUs, and State Tax Revenues Pervasive Optimism and Reflexivity Risk The Fed's "Path of Least Resistance" The Warsh Nomination and Forward Guidance Productivity Boom or Demand Story? AI's Wealth Effect Beyond Accounting The 2027 Fiscal Headwind Substack vs. Institutional Research

Can you really know if you're ready to retire? Jeremiah and Alex spend much of this episode unpacking one of the most commonly misunderstood tools in financial planning: retirement projections and Monte Carlo simulations. They explain what an 85% or 90% probability of success actually means, why those numbers can be useful, and where they can create a false sense of certainty if they're viewed in isolation. They explores sequence-of-return risk, retirement spending assumptions, inheritance surprises, and the reality that successful retirement planning requires far more than simply hitting a target number. Later in the show, Jeremiah and Alex tackle another area where people often misunderstand the rules: company stock compensation. They break down how RSUs, stock options, and employee stock purchase plans work, why taxes can catch employees off guard, and the planning opportunities available when company stock becomes a meaningful part of your net worth.   Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com Hosts: Jeremiah Bates & Alex Lundgren ————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————

Want to know what the top earners in pharmaceutical sales actually take home? The numbers you see on job boards dramatically undercount the truth because they leave out quarterly bonuses, RSUs, car allowances, and life-changing equity buyout premiums. Every Monday night, we coach you live to land the job. In this episode of Medical Sales U, Dave Sterrett breaks down the Top 7 Highest-Paying Pharmaceutical Sales Jobs in the country right now. From the incredible work-life balance of dermatology biologics to the multi-millionaire equity upside of oncology biotech startups, we are counting down the real numbers and giving you the honest truth about what it takes to clear the bar and land these elite specialty roles.TIMESTAMPS00:00 - Intro: What Job Boards Get Wrong About Pharma Compensation02:15 - The Total Compensation Formula (Base + Bonuses + RSUs)04:30 - #7: Dermatology Biologics Sales Specialist ($140K - $230K)07:10 - #6: Cardiology & GLP-1 Metabolic Sales Specialist ($155K - $250K)10:05 - #5: Neuroscience & CNS Sales Specialist ($175K - $250K)13:20 - #4: Rare Disease Key Account Specialist ($180K - $300K)16:45 - #3: Biotech Specialty Sales (Gene & Cell Therapy) ($200K - $320K)19:30 - #2: Oncology Sales Specialist - Large Pharma ($200K - $315K)22:15 - #1: Oncology Biotech Startup Sales Specialist ($240K - $350K+ No Ceiling!)24:40 - How to Build Your Record & Earn Clinical CredibilityIf you found this breakdown valuable, please SUBSCRIBE, drop a comment saying “Break in”, and share this with someone mapping out their trajectory in the medical sales industry!Ready to break into medical sales and secure your first $95k+ base offer?Join Medical Sales U: medicalsalesu.com/#MedicalSales #PharmaSales #PharmaceuticalSales #MedicalSalesU #OncologySales #BiotechJobs #HighPayingCareers #SalesCompensation

In this episode of Fundamentals of Investing, Brian Dress and Noland Langford tackle one of the most common (and most overlooked) financial challenges facing corporate executives: what to do when your company stock becomes a dominant part of your net worth. They cover the full picture of equity exposure (RSUs, stock options, ESPP, deferred comp, and 401(k)), walk through the real math of concentration risk, and offer a practical framework for when and how to start diversifying, including how to think about the tax implications without letting them drive the decision. Topics covered: - Why high concentration is so common among executives (and why it often goes unexamined) - How to stress-test your position before the market does it for you - Long-term capital gains vs. ordinary income: what the rates actually mean for your decision - Dollar-cost averaging out: the simplest path to reducing concentration over time - The lifetime financial model: a framework for making the decision analytically, not emotionally Resources mentioned: [Watch the episode on YouTube here →] https://youtu.be/nT2NpdtIa1Q [Download the free Executive's Guide to Equity Compensation →] https://leftbrainwm.com/theexecutiveguide [Book a free 30-minute review with Brian →] https://tinyurl.com/Book30MinutesWithLeftBrain Full Disclosure No Client or potential client should assume that any information presented or made available on or through this video should be construed as personalized financial planning or investment advice. Personalized financial planning and investment advice can only be rendered after engagement of the firm for services, execution of the required documentation, and receipt of required disclosures. The content is developed from sources believed to be providing accurate information. The information in this material is not intended as tax or legal advice. It may not be used for the purpose of avoiding any federal tax penalties. Please consult legal or tax professionals for specific information regarding your individual situation. Additional information about Left Brain is available in its current disclosure documents, Form ADV, Form ADV Part 2A Brochure, and Client Relationship Summary (Form CRS), which are available online via the SEC's Investment Adviser Public Disclosure (IAPD) database at www.adviserinfo.sec.gov/firm/summary/170348.  

Retirement planning is about more than just saving money—it's about making smart decisions with your finances to ensure that you keep as much of what you've earned as possible. On the show this week, I'm sharing essential strategies for managing your taxes in retirement—including a real-life example of a couple selling $146,000 in capital gains and paying zero taxes. I break down the benefits of non-retirement brokerage accounts, clarify the rules around capital gains and losses, and reveal a key element of the tax code that hasn't changed in nearly 50 years. In the second half of the show, I'm also discussing the risks and rewards of company stock, stock options, and restricted stock units (RSUs), and providing guidance for anyone investing in their own company or dealing with equity compensation. This episode is packed with practical advice and insightful stories to help you retire in the best financial position possible.   You will want to hear this episode if you are interested in... [00:26]Importance of tax management in retirement [02:05] Capital gain harvesting (an uncommon topic) and capital loss harvesting [06:25] Explaining brokerage account basics [08:17] Distinction between short-term vs. long-term capital gains [14:24] Practical example of managing large capital gains [18:30] Tax-free capital gains strategy [24:40] Understanding equity compensation risks [31:51] RSUs and the tax implications [33:27] Evaluating company stock and options Understanding Brokerage (Non-Retirement) Accounts Brokerage accounts, also known as non-retirement accounts, are investment accounts funded with after-tax dollars. Unlike IRAs or 401(k)s, which have strict withdrawal rules and penalties, these accounts offer much more flexibility. There are two primary advantages: Accessibility: Funds are available before age 59½, meaning you aren't locked into waiting as with some retirement accounts. Tax Control: Taxes in these accounts are mainly due on capital gains, dividends, and interest, and you can influence the timing and amount of tax owed by managing what and when you sell.   Many investors overlook the advantages of these accounts, often assuming that retirement planning must revolve solely around 401(k)s and IRAs. Speaker B points out that one of the biggest benefits is the ability to 'cherry pick' what is bought and sold, giving investors direct control over their tax liabilities.   Capital Gains and Loss Harvesting Most people are familiar with the idea of harvesting capital losses—selling investments at a loss to offset taxable gains or up to $3,000 of ordinary income per year. But 'harvesting capital gains' can also be a powerful strategy. If your income is low enough in a particular year, it's possible to realize long-term capital gains at zero federal tax, especially under current tax laws. There are nuances, however. The $3,000 capital loss deduction limit hasn't changed since 1978, despite decades of inflation, and excess losses must be carried forward to future years—a critical aspect often forgotten. Additionally, the wash-sale rule prevents you from writing off a loss if you purchase the same (or substantially identical) security within 30 days before or after the sale.   Risks and Rewards of Company Stock, Stock Options, and RSUs  Equity compensation—whether through company stock, stock options, or restricted stock units (RSUs)—is a growing component in many retirement portfolios. Stock options come in two primary flavors—incentive stock options (ISOs) and non-qualified stock options (NSOs)—with distinct tax treatments. The potential upside can be huge, especially in fast-growing companies, but if the stock price falls below the strike price, the options may end up worthless. Upon vesting, the value of Restricted Stock Units (RSUs) is taxed as ordinary income. Many companies manage tax withholding by selling some shares at vesting, but any future gains after vesting are subject to capital gains tax. Overreliance on one company's stock can be financially devastating. Don't be like the Enron employee who lost almost everything by refusing to diversify. It's essential to manage company-specific risk and diversify holdings as you approach retirement.   Resources & People Mentioned 3 Steps to Retirement Planning IRS Case Study 1 – Wash Sales    Connect With Gregg Gonzalez   Email at: Gregg.gonzalez@lpl.com Podcast: https://RetireStrongFA.com/Podcast Website: https://RetireStrongFA.com/ Follow Gregg on LinkedIn Follow Gregg on Facebook Follow Gregg on YouTube Subscribe to Retirement Made Easy On Apple Podcasts, Spotify, Google Podcasts  

Send us Fan MailThe data is clear: staying loyal to one employer rarely keeps pace with what strategic career moves can do for your income. But what does "smart" job hopping actually look like, and when does loyalty still win?In this episode, Jessica and Brandon get real about the job hopping vs. loyalty debate. They share firsthand experience navigating layoffs, negotiate their way through six-figure compensation packages, and break down the framework listeners can use to make career decisions that actually build wealth.Topics covered:Why piddly 1.5–3% annual raises are costing you serious long-term wealthHow to use competing offers to negotiate with your current employer without quittingThe right and wrong reasons to make a lateral moveVesting schedules, RSUs, and benefits you should never leave on the tableThe 15–20% rule: the number that makes a job switch worth the disruptionWhy interviewing is a skill you must keep sharp — even when you're happyHow to build a network that works for you before you need itWhat a client negotiated by simply asking ($30K base increase + doubled equity)Beyond salary: education stipends, PTO, remote work, fertility benefits, and moreClosed mouths don't get fed. This episode gives you the tools to start asking.Subscribe to The Sugar Daddy Podcast newsletterExplore The Sugar Daddy Podcast Stan Store — Downloadables, tools, and more to level up your money game together!Head over to our YouTube channel to catch this episode in full video form.Apply to be a guest on the show.You can also email us at: hello@thesugardaddypodcast.comConnect with us on Instagram We're most active over at @thesugardaddypodcastChat with BrandonWant to work together? Learn more about BrandonBook a free 30-min call to see if it's a fit.Show us some love, hit subscribe, leave a five star rating, and drop a quick review!Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jessica, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Their mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially....

RSUs can feel like a great opportunity, but they can also create a tough question: Should you sell when they vest, or hold the stock and see what happens? In this episode of Clear Money Talk, Tim Clairmont, MSFS™, LACP™, Wealth Advisor, and Tyler Andrews, CFP®, Wealth Advisor, break down the key considerations behind restricted stock units, including taxes, concentration risk, emotional attachment, and how company stock may fit into a broader financial picture. They also explore one simple question that can help clarify the decision: If this showed up as cash instead of stock, would you use that money to buy the same company's shares? Tune in for a clear, practical conversation about RSUs and why the right decision depends on more than the stock price.

RSUs can feel like a great opportunity, but they can also create a tough question: Should you sell when they vest, or hold the stock and see what happens? In this episode of Clear Money Talk, Tim Clairmont, MSFS™, LACP™, Wealth Advisor, and Tyler Andrews, CFP®, Wealth Advisor, break down the key considerations behind restricted stock units, including taxes, concentration risk, emotional attachment, and how company stock may fit into a broader financial picture. They also explore one simple question that can help clarify the decision: If this showed up as cash instead of stock, would you use that money to buy the same company's shares? Tune in for a clear, practical conversation about RSUs and why the right decision depends on more than the stock price.

A buyout offer can feel like a gift, but it can also quietly wreck a retirement plan if you treat the severance cheque like a finish line. Let's walk through the real-world decisions behind Microsoft's recent reported voluntary retirement style separation package and why moves like this matter to anyone working at a large company. When one major employer offers early exits, the idea spreads fast, and the next offer could land on your desk with a deadline and a surge of emotion.The five biggest mistakes I see when people accept an early retirement package: Overvaluing the payout instead of building a durable retirement income plan, underestimating healthcare costs and the Medicare gap, claiming Social Security too early out of fear, forgetting how brutal taxes can be in a package year (salary, PTO, bonus, RSUs, and severance piling up at once), and retiring from something without a clear purpose to retire to. We also talk through why companies do this, from payroll reduction and reshaping the workforce to freeing capital for priorities like AI and infrastructure.To help you decide without panic, I share three grounding questions: Are you financially independent already, does the offer truly improve your position, and what is your best alternative if you stay or work longer? If you're within five years of retirement and want clarity on income, taxes, Social Security timing, and healthcare, subscribe, share this with someone weighing a buyout, and leave a review so more people can find it.

When tax season ends, tax planning begins. Join host Bryan Bibbo as he sits down with Chad Weigl, CFF, BPC, NSSA, lead advisor at JL Smith Holistic Wealth Management, a Prosperity Capital Advisors company, to walk through what high-income earners and pre-retirees should consider once their return is filed.   With more than a decade of experience in retirement income planning, tax strategy, Social Security, and estate planning, Chad breaks down which line items on your return reveal some of the biggest missed opportunities, and how to translate this year’s outcome into a smarter plan before the window closes.  Key Topics:  Your Tax Return as a Planning Tool: Why filing it away until next April can be a costly mistake, and which specific line items deserve your attention right now.  The Hidden Cost of Capital Gain Distributions: How internal trades by mutual fund and exchange-traded fund (ETF) managers can generate surprise taxable events, and what strategies may help reduce them.  Tax-Efficient Withdrawal Strategies: How structuring distributions across pre-tax, post-tax, and Roth accounts can help keep you in the lowest possible bracket throughout retirement.  Roth Conversions and Market Downturns: Why periods of market volatility can create timely opportunities to convert more shares at a discount and let them recover tax-free.  Planning for High-Income Earners: How to approach deferred compensation elections, restricted stock units (RSUs), and equity compensation, and why many of these decisions often need to be made a full year in advance. 

Think the real money in medical sales is only in the Operating Room? Think again.Discover how specialty Pharma and Oncology reps are quietly earning $200K - $300K+ without ever stepping into a scrub suit. In this episode, Dave Sterrett, founder of Medical Sales U and former #1 national rep at Sanofi and Virtuox, breaks down the exact numbers behind the most misunderstood — and lucrative — side of the industry: Specialty Pharma and Oncology Diagnostics.Stop listening to the "device youtuber" that says Pharma is just dropping off samples. We're diving into the high-level clinical selling required to dominate oncology and precision medicine. TOPICSThe Income Reality: Why the "floor" for our members starts at a $95,000 base salary.The Career Ladder: A step-by-step breakdown from entry-level ($110k) to Oncology ($230k+ base).Beyond the Salary: The "hidden" wealth in RSUs, ESPPs, and expense accounts that add $50k+ in value.The Interview Secret: Why smart people fail the "Clinical Conversation" and how to fix it.Work-Life Balance: Why veteran Device reps are leaving the OR for the flexibility of Pharma. CHAPTERS0:00 - The Case for Pharma & Diagnostics2:15 - My Journey: Turning a Territory Around5:45 - Debunking the "Pharma is Easy" Myth10:30 - The Salary Floor: $95k - $125k Base15:10 - The Oncology Tier: $150k - $230k Base20:45 - The Truth About OR Burnout28:30 - How to Master the Clinical Conversation35:00 - Building Generational Wealth with Equity Ready to break into medical sales and secure your first $95k+ base offer?Join Medical Sales U: medicalsalesu.com/Every Monday night, we coach you live to land the job.

I n this episode, Left Brain Wealth Management CEO Noland Langford and Director of Research Brian Dress address one of the most painful and underserved situations in executive finance: your concentrated company stock position is falling — and you don't know whether to act or wait. Noland and Brian walk through the psychology of why executives get stuck, the real options available beyond "sell everything or do nothing," and the practical steps you can take right now — even if you're not ready to make a big move yet. Topics covered: • The emotional weight of watching your net worth decline in real time • Why company loyalty becomes a financial liability at the wrong moment • The tax reality of RSUs: ordinary income on the way in, capital loss on the way out • The anchoring trap and how to reframe your thinking • How to talk to your spouse about this before it becomes a crisis • What documents to bring to a first advisor meeting • Questions every executive should ask a potential financial advisor — and the red flags that disqualify one Resources mentioned: • Book a free 30-minute call with Brian Dress: https://tinyurl.com/Book30MinutesWithLeftBrain • The Executive's Guide to Managing Company Stock (free e-book): https://leftbrainwm.com/theexecutiveguide • Left Brain Wealth Management: leftbrainwm.com | 630-517-9300

Stock options can be a valuable part of compensation, but they also come with important tax considerations, vesting schedules, and investment decisions. In this conversation, Jeremiah and Laura break down the differences between RSUs and RSOs, explain how vesting works, and discuss why many employees feel overwhelmed when trying to make decisions around concentrated stock positions and taxes. They also walk through common planning considerations for tech employees, startup professionals, and anyone receiving equity compensation through work. Whether you're newly receiving stock compensation or trying to better understand an existing plan, this episode highlights why having a long-term strategy matters. #StockOptions #RSUs #FinancialPlanning #WealthManagement #EquityCompensation --- Information and ideas discussed are general comments and cannot be relied upon as pertaining to your specific situation, do not constitute legal/financial advice, and do not create an attorney-client or fiduciary relationship. Examples discussed are fictional. You should consult your own advisor/attorney and do your own diligence prior to making any decisions. Investments involve risk and the possibility of loss, including the loss of principal. All situations are different, and results may vary. Randy Barkley is a life insurance agent CA license # 0518567 and Jeremiah Lee is a California licensed attorney and is responsible for this communication. Advisory services offered through TriCord Advisors, Inc., a Registered Investment Advisory firm.

In this episode of Experts Unleashed, I sit down with Chris Chen from insightfinancialstrategists.com to explore what financial planning actually looks like when life falls apart. We talk about why regular financial planning is about applying the rules — and divorce financial planning is about applying the exceptions, how Chris went from economics dreams and a tech career to building a fee-only advisory practice dedicated entirely to women navigating divorce, and why most women wish they had found him before the divorce even started. I also share insights on the three financial questions every divorcing woman must answer, why wanting to keep the house is often the worst financial decision, and what knowledge truly does for someone in the middle of an emotional maelstrom. Plus, we get into RSUs, stock options, the 401k exception almost no one knows about, and why we're not in the money business at all — we're in the people business.   

Washington's Proposed Millionaires Tax (SB 6346) and the "Seattle Tax Stack": Mechanics, Migration, and Real Estate Impacts Industrial Advisors Podcast hosts Bill Condon and Matt McGregor discuss Washington's proposed "Millionaires Tax," SB 6346, a 9.9% tax on household income above $1 million, noting it can effectively hit dual-income households and "lumpy" stock-based compensation. They describe a cumulative Seattle "tax stack" (9.9% state, 5% social housing, 2.4% JumpStart, 0.58% WA Cares) exceeding 18% before federal taxes, potentially reaching 55–60% total, and argue it could influence jobs, investment, sports free agents, and real estate demand, including taxation of Washington-sourced income for nonresidents. Using an AI-generated deep dive built from documents, the episode compares migration and revenue dynamics in New York and California, explains domicile-planning timelines, highlights QSBS (Section 1202) as a potential shelter, and emphasizes the risk that the $1 million threshold could be lowered, especially if tech valuations fall and projected revenues miss. 0:00 Cold open: the $1M household threshold 0:46 Introduction to Washington's proposed millionaires tax 2:08 RSUs, deferred income, and one-time tax events 3:10 Seattle's 18% local tax stack explained 5:31 Commercial real estate and Washington-sourced income 7:00 Investor demand, property values, and economic ripple effects 8:01 Why Bill and Matt used AI for this episode 10:15 AI deep dive: tax flight and wealth migration 11:19 Washington as a national tax policy test case 14:32 Revenue projections and the 21,000 filer base 15:22 The Seattle tax stack breakdown 16:50 Federal taxes and the 55%–60% combined burden 18:47 The real estate exemption in SB 6346 19:37 Lessons from Los Angeles Measure ULA 22:57 Luxury housing demand and high-net-worth buyer risk 24:11 2028 effective date and relocation planning 26:35 RSUs and "lumpy vesting" risk for tech workers 28:05 The marriage penalty in the proposed tax structure 30:06 QSBS as a potential shelter for founders 33:13 California, New York, and wealth migration data 36:38 Remote work and the new mobility of high earners 38:47 Why the $1M threshold may not stay fixed 41:04 Massachusetts and the risk of expanding the tax base 43:29 Tech market correction risk and revenue shortfalls 44:32 Final takeaway: the "leaky bucket" problem 45:06 Closing comments

On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle a critical question for investors: what happens if the next decade of market returns doesn’t cooperate—and does your financial plan rely on strong returns just to survive? They break down how to properly stress test your retirement plan using real-world scenarios, Monte Carlo analysis, and the importance of separating must-have expenses from discretionary spending to weather any environment. Plus, they dive into the hidden complexities of restricted stock units (RSUs), including how they’re taxed, vesting schedules, and why they should be treated as a concentrated position in your portfolio. You’ll also hear strategies for protecting your retirement timing from market downturns, how to think through pension lump sum versus income decisions, and smart ways to gift money for major life events without triggering unnecessary taxes. See omnystudio.com/listener for privacy information.

Send us Fan MailFive assets keep showing up when divorcing couples hit a wall, and the reason is almost never just emotion. It is value. I sit down with founding attorney Lewis Landerholm to unpack why retirement accounts, the marital home, business interests, investment portfolios, and valuable personal property become the flashpoints in divorce and family law cases, especially when each asset carries different tax rules, different volatility, and different paperwork.We get practical about the hidden math: why pre tax 401(k) dollars are not the same as cash, when pensions require an actuary, and how premarital versus marital components can change the division. Then we move to the marital home, where the deed is often easy but the mortgage can be the real obstacle, particularly when a refinance means higher interest rates and a smaller buying power for the spouse who keeps the property. We also explain why judges tend to choose the simplest clean break if a plan is not realistic, and why vague terms in a divorce decree can lead to expensive enforcement fights years later.From there we dig into business valuation, including why picking the right valuation expert matters, what happens when both spouses work in the business, and how buyouts can collide with future cash flow and support issues. We also cover investment accounts, RSUs and stock gains, cost basis, and the tax surprises that can dwarf the “headline” account value. Finally, we talk about appraisals for cars, jewelry, art, and even bitcoin, where volatility makes timing and documentation critical.If you found this helpful, subscribe for more real world divorce guidance, share this with someone sorting out a separation, and leave a review so more families can find clear answers.If you would like to speak with one of our attorneys, please call our office at (503) 227-0200, or visit our website at https://www.pacificcascadelegal.com.Disclaimer: Nothing in this communication is intended to provide legal advice nor does it constitute a client-attorney relationship, therefore you should not interpret the contents as such.

If you work at a publicly traded company and receive any form of equity compensation, RSUs, stock options, ESPP, or deferred comp, this episode is for you. Brian Dress and Noland Langford walk through the executive diversification trap: how concentration in employer stock builds gradually, why it is so hard to act on, and what a structured plan to address it actually looks like. Topics covered: • How a $200K salary can represent $6 million or more in future earnings power • Golden handcuffs: what they are and what they cost you • The FOMO psychology that keeps executives stuck on both winners and losers • Why selling everything at once is almost never the right answer • Deferred compensation: the most underused executive benefit • How to think like an investor, not an employee Resources mentioned: Watch the full episode here via YouTube: https://youtu.be/-urw560-Sts  Executive's Guide to Company Stock: https://leftbrainwm.com/theexecutiveguide May 27 Estate Planning Webinar (free, recording available): https://tinyurl.com/May27EstatePlanningWebinar Schedule a no-cost, no-obligation consultation: https://tinyurl.com/Book30MinutesWithLeftBrain Left Brain Wealth Management. Independent, Objective, Unbiased. Investing involves risk, including the possible loss of principal and fluctuation of value.  Past performance has no guarantee of future results. This video is not intended to be relied upon as a forecast, research or investment advice, and is not a recommendation, offer or solicitation to buy or sell any securities or to adopt any investment strategy. The opinions expressed are as of the date noted above and may change as subsequent conditions vary. The information and opinions contained in this video are derived from proprietary and nonproprietary sources deemed by Left Brain Wealth Management, LLC ("Left Brain") to be reliable, are not necessarily all-inclusive and are not guaranteed as to accuracy. As such, no warranty of accuracy or reliability is given and no responsibility arising in any other way for errors and omissions (including responsibility to any person by reason of negligence) is accepted by Left Brain), its principals, employees, agents or affiliates. This video may contain "forward-looking" information that is not purely historical in nature. Such information may include, among other things, projections, and forecasts. There is no guarantee that any forecasts made will materialize. Reliance upon information in this video is at sole discretion of the reader.   Please consult with your Left Brain financial advisor to ensure that any contemplated transaction in any securities aligns with your overall investment goals, objectives and tolerance for risk. In addition, please note that Left Brain, including its principals, employees, agents, affiliates and advisory clients, may have positions in one or more of the securities discussed in this communication or effect transactions contrary to the views expressed in this communication based upon individual or firm circumstances. Any decision to effect transactions in the securities discussed within this communication should be balanced against the potential conflict of interest that Left Brain has by virtue of its investment in one or more of these securities.  Additional information about Left Brain is available in its current disclosure documents, Form ADV, Form ADV Part 2A Brochure, and Client Relationship Summary (Form CRS), which are available online via the SEC's Investment Adviser Public Disclosure (IAPD) database at www.adviserinfo.sec.gov/firm/summary/170348.  Left Brain is neither an attorney nor an accountant, and no portion of this content should be interpreted as legal, accounting or tax advice. Left Brain does not provide investment banking services nor engages in principal or agency cross transactions.

The Great private Capital Reset is upon us. Markets are volatile and driving new economic imperatives. Are VC funds still VC funds, even if they raise billions per fund? What happened to the rest of the market? What is driving VC investments? What do Limited Partners think? What is on their minds? This and more, in episode 76 of Tech Deciphered. Navigation: Intro The State of the Reset: The Hangover from the Party? LP Fatigue and VC Differentiation What Really Matters: Performance.. Returns The Mega Fund Question The Case for Smaller… Rightsized Funds What Comes Next? Conclusion Our co-hosts: Bertrand Schmitt, Entrepreneur in Residence at Red River West, co-founder of App Annie / Data.ai, business angel, advisor to startups and VC funds, @bschmitt Nuno Goncalves Pedro, Investor, Managing Partner, Founder at Chamaeleon, @ngpedro Our show: Tech DECIPHERED brings you the Entrepreneur and Investor views on Big Tech, VC and Start-up news, opinion pieces and research. We decipher their meaning, and add inside knowledge and context. Being nerds, we also discuss the latest gadgets and pop culture news Subscribe To Our Podcast Bertrand Introduction Welcome to episode 76 of Tech Deciphered. This episode will be about the great private capital reset. As you know, or you have probably heard, there is significant structural transformation in the world of venture capital, and we are probably witnessing a fundamental reset of the private capital stack. We got a huge bubble in 2020, 2021. Fueled by near-zero interest rates. We got inflated fund size, compressed due diligence, and now a generation of zombie funds and zombie startups. Now that rates have normalized, exits have not been as much as expected. LP patience is a warning sign, and I guess the industry is being forced to confront an uncomfortable truth: most VC funds raised since 2017 might not return what their LPs expected. You know, how do we start?   Nuno This is going to be a relatively nuanced episode. Obviously, there is going to be a lot of haves and have-nots, both in terms of VC funds, also in terms of startups. And so I want to start with that. This is going to be more nuanced than all transformational and disruptive.   Bertrand It’s not the end. It’s not the end.   Nuno State of the Reset: The Hangover from the Party? It’s not the end. There’s still huge mega funds that are raising more and more. It’s clear that the music has stopped, right? So if we’re playing the game of chairs, the music has stopped. Around ’22, ’23, we started seeing the first signals that funds had raised way too much money. Firms collectively raised around $669 billion globally in 2021 alone. If we fast forward now to last year, 2025, depending on the sources, we did some internal analysis at Chameleon. We came up with $75.6 billion was raised last year by 493 funds, right? So That’s a significant drop, right, in terms of fundraising. Other sources would say a little bit more. There’s a little bit of a discussion around how much did the top 30 funds capture. If you believe some of the stats out there, they would say that actually top 30 funds captured 75% of all capital raised last year. We did again some internal analysis at Chameleon, and the conclusion we came to, it was closer to 50 to 55%. So not as dramatic as some of the sources out there, but still pretty dramatic. There’s a lot of capital concentration on the top funds. Again, the top 30 funds would’ve raised 50 to 55% of capital or up to 75% according to other sources. So definitely a tremendous amount of concentration. There was a lot more fragmentation in terms of capital raised if we’re looking at the years from 2010, 2011, all the way through 2021. So 2021 would’ve been sort of the peak of non-concentration if you look at that. And that again, now we are getting more and more concentration. There’s more and more of this arbitrage around, I’ll give money to the top funds, I will not give money to the smaller funds, or I’ll give less money to the smaller funds. There’s a little bit of a movement around concentration. We’ll talk about it later and what that means. Are mega funds really better? Are the small funds still the way to go? We’ll talk a lot about that later in today’s episode. There seems to be a little bit of a bifurcation. We could say it’s either bifurcation around top-tier VCs or larger VC funds versus smaller VC funds. My perspective is the bifurcation that we’re seeing right now is more of a bifurcation between funds that are no longer just stepped into the VC space, but they’re actually becoming more and more private equity firms with full asset management range from early stage all the way to late stage. Think of it almost like a private equity hedge fund, quasi, versus classic VC funds. And I think what we’re seeing is the Andreessen Horowitzes, the a16zs of the world, the NEAs, the Sequoia Capitals, just to name a few, becoming more and more broad asset class managers across private equity, whereas you have more classic VC happening in earlier stages. And so that’s the real bifurcation that I think is actually happening.   Bertrand And maybe not really hedge fund, because they are always still long-only funds. So there is no hedging happening, at least as far as I know.   Nuno Well, some of these guys have become RIAs, like A16z has become an RIA, so they can do secondaries.   Bertrand That’s true. Yeah.   Nuno And they can also sell stuff, etc. So I don’t know how aggressive they’re going to be in terms of secondaries and selling and actually doing other kinds of services you can do if you’re an RIA. But it’s not, I think, out of the realm of possibility that they would sort of acquire and sell stock more rapidly. In that way, to your point, Bertrand, maybe they actually become beyond just long guys, right?   Bertrand Yes. Another trend I have seen is some of the larger VC funds seems to have no problem investing in multiple competitors. This was not possible before. I mean, if you’re a VC fund, you had some sort of duty not to invest in the competitors, but now some invest OpenAI, Anthropic at the same time. Do you see that as part of this evolution?   Nuno For sure. And I think there’s a lot of people like the ostrich putting their heads below the ground and it’s like, “Eh, no, no, nothing to see here.” But that does constitute a conflict of interest. And if I’m a startup raising, this assumption that you will not invest in one of my competitors is no longer there, certainly for the mega funds, because of that notion of deployment of capital. Now, some funds will still hide under the notion, actually formally from a fund perspective, we’re not investing in competitors. It just happens that different types of our funds are investing in competitors. Like maybe my growth fund is investing in a competitor to my early stage fund, right? But our funds are relatively independent. So I think there’s a little bit of hide and seek that will go on if you talk to some of the fund managers. Well, they say, well, we’re not investing out of the same fund into these competitors. But between you and I, as we know, a lot of these partnerships actually do a lot of stuff together at the general partnership level. So are there really actual Chinese walls between the funds? Well, it really depends on the partnership. And to be honest, most of the partnerships don’t have very significant Chinese walls between the funds, right? The managing general partners sometimes actually occupy investment committee roles across different funds. So I think the conflict of interest is there. So that’s why I say there’s a little bit of ostrich behavior. Put your head behind the ground or below the ground and just pretend nothing is happening. Just sharing maybe a couple of interesting stats. Global fund closings for 2025, according to our numbers at Chameleon, 1,098 closed. In 2025. Closed is when you start deploying capital, right? Whereas— so it’s not closed down, it’s closed like we start deploying capital. And that number, 1,098, is dramatically down from 1,600 in 2024. And it’s actually the lowest number of closings that we saw since 2014. So again, this is bad, right? It means there’s less funds doing fund closings and deploying capital in the market than since 2014 and dramatically below the 2024 numbers, right? Where we already saw some market readjustments. The number of active VC firms in the US that did 2+ deals, which is not a huge bar, has dropped 38% back to numbers in 2023. So we don’t have numbers that are a little bit more up to date, but basically in 2023, those numbers are already dramatically dropped. So there’s less and less active funds. So there’s funds that might be in the market, but they’re not actually deploying that much capital, not doing that many investment. They’re sort of either zombie funds or relatively passive funds that have passed their investment period. For those listening to us, the investment period for a VC fund is normally between the first 3 to 5 years of the fund, which is when you build your portfolio, when you can invest in new companies. After that time period, everything that you do up to normally what would be year 10 is follow-ons. You put more money into the companies that you’re already invested in, that you already constructed portfolio with during those 3 to 5 years.   Bertrand Yeah, that’s a pretty scary change. And obviously, I guess we’ll come to it, but the time it takes to fully liquidate investments is getting longer and longer. In the old days, we used to talk about VC funds having a 10-year life, maybe a +1/+1 in terms of extension of the fund life. But it looks like it’s taking 16 to 18 years actually to get full liquidity from a fund investment.   Nuno LP Fatigue and VC Differentiation And I think that’s the scariest piece. I mean, just to share some numbers, we in venture capital talk about vintages, right? Which year did your fund start in? Normally when you did your first close onto the fund, as we were saying before, close is when you get all your investors at that moment in time to come in and you do your first close so the next fund starts running. 2018 vintage funds, right? This is now almost 7 years ago. So you should start having— actually 8 years ago almost at this point in time. You should start already getting distributions or you start getting cash back if you’re a limited partner and investor in those funds, you should start getting cash back. Half of all 2018 vintage funds have returned $0 to their LPs. So they’ve had no distributions to their LPs. 2020 vintage, which was a very hot vintage, only 42% have begun any distribution. So 58% have distributed $0, right? 2021, only 25% have done any distributions. Now, I happen to have a 2018 vintage fund and a 2021 fund. My 2018 fund has already distributed over 3x net of fees in distributions, and my 2021 fund’s already over 10% distributed back in distribution. So we’re very proud of that. But in general, the numbers are awful. There’s no liquidity back to LPs. And to your point, that’s kind of a big deal because some of these funds have been going on for 7, 8 years, and where’s the liquidity going to come from? On the other hand, if you look at TVPI, so DPI is distributions to paid-ins cash on cash. But if you look at TVPI, which is total value to paid-in, which also includes the book value or the value that you’re marking it on your books, basically the paper value as we call it for the company, even on that, the median 2017 fund, so 2017 vintage fund has a TVPI, total value to paid-in, of only around 1.76x, which is well below what should be, which is sort of the 2 to 3x benchmark of a really good performing fund. So the median funds are doing very, very poorly overall. So if you add that to the fact of what’s happening and distributions are taking a long time, back to your point, Bertrand, it’s taking like— this should be a 10-year asset class, maybe 11, 12 years, and now it’s looking a little bit like a 15, to 18-year asset class, which is not what most limited partners sign up for. Part of this dynamic, I think, is that we’ve had tremendously overvalued private companies over the last few years, right? Secondly, these companies have just stayed private longer. And I was having a discussion recently with a friend of mine, it’s like, hey, what’s this thing about companies are staying private much longer? Is there some dynamic around secondaries? And the reality is there is a dynamic around secondaries, right? Because if I’m a very large fund and I can get away with doing secondaries on my portfolio, I will get liquidity at some point, right? But someone else is stuck with private stock, which hopefully will IPO, but who knows, right? And so there’s this funny dynamic right now of because of secondaries, because of a couple of other things that are happening in the market, actually a lot of these startups are staying private for tremendous amounts of times, and some of them will IPO and they’ll be huge deals. Some of them might not and might not warrant the latest private valuations that they’ve exercised. And so there’s this tremendous noise that we’re seeing in the mid to late funnel of privately held companies where some are just waiting to be public. Some of them might not be able to go public at anything that is an up round versus private valuations that they’ve had in previous moments and in previous rounds.   Bertrand And obviously the 2 to 3x returns that funds are targeting, and obviously more 3x than 2x, I mean, that was good and nice if it’s a 10-year fund, but if it’s the same 3x for 15 to 18 years, it’s not at all the same rate of return annualized. So it’s a really, really, really big issue if you keep the return the same, but you extend the duration of the fund. Concerning going IPO, there is a lot of complexity going public, the IPO process itself, but also after that when you’re a public company. It changed how you can run the business. Some would argue that we have had an issue with more companies delisting than companies listing on the public market. So I think there might be also separate issues about the efficiency of the public market and maybe a need for change. We went very strongly in one direction for the public market, have post and run, but was it really ultimately the right thing to do? I’m actually not so sure.   Nuno Yeah, I mean, just to be clear, this is anecdotal, but when we tell prospective LPs at Chameleon about our returns, the last few funds, 2018, 2021, the first reaction is, “You must be lying, right? Surely you can’t have distributions already for 2021,” et cetera, et cetera. So clearly there’s almost a state of disbelief right now from limited partners. And liquidity does matter. So clearly you have to move forward. So how did we get to this point where we had this bubble 2021 all around that time space and now things don’t look so good. Well, the macro conditions have changed dramatically. I mean, rates when they were near zero, safer assets yield nothing or yield nothing. So basically you had to push capital into longer duration risk assets like venture capital. And so you had to push it. So the opportunity cost of capital also has fundamentally shifted. Obviously a 3x VC return in 15 years over 10 actually competes very poorly against 5% annual credit returns over several years. So there’s been a readjustment of stuff. And then the public equities in particular, the tech public equities have had a lot of volatility, but some of them have done extremely well, right? Chipsets, things like NVIDIA, the Amazons of the world, Alphabets, et cetera, et cetera. They’ve done very, very well. So why would I invest in a long-term illiquid asset that takes now longer to give me money back, and in some case doesn’t give me back, if I can invest just in public equities, and a variety of other things. The venture debt costs have increased dramatically. The burn rates that were sustainable back in the day with sort of the addition of venture debt, private credit, et cetera, now are overblown at this moment in time. At the end of the day, there’s been a lot of movements also overall in the pipeline in terms of valuations, et cetera, et cetera. Now, I would put a grain of salt into all the numbers I just told you. There still is a little bit of the haves and have-nots in startup land. Certainly in early stage where if you’re a hot AI company, you can get away with raising a Series C or $480 million. This is actually a true story. Series C, right? Not Series C, a $480 million at $4 billion pre-money valuation. Whereas if you are maybe in a space that’s less hot, you’ll have more difficulty in raising money at this point in time, might not be able to even raise a Series C, right? So there’s a little bit of the haves and have-nots happening on the VC side in early stage that has been really amplified by the macro regime and where we’re at, which is actively zero-rate era is done and now the new regime is quite different. And so I can get better returns by doing something else.   Bertrand Kind of makes sense. I mean, if you have some ways the SaaSpocalypse in the public market because there is that fear that AI is going to completely change the game for especially for the more typical software companies. Good luck raising private money to quote unquote just build traditional software companies. You cannot expect a warm embrace from the private market if the public markets are completely destroying that category. I’m not saying that this is there forever, uh, things might change over time, but for sure what’s happening on the public markets always have a very strong impact on the private market.   Nuno Indeed. So what’s happening in this relationship between limited partners and VCs, the general partners? Again, limited partners are the people that give venture capital firms and venture capital funds their capital to actually deploy. And they are a variety of different players, right? Could be endowments, like university endowments, pension funds, family offices, very high net worth individuals, fund of funds, et cetera, et cetera. I mean, in particular, if you look at the institutional investors, the endowments, the pension funds, the fund of funds, they have allocations that they do to different asset classes typically. And the feedback that we’ve received from the market is they are increasingly frustrated with what’s happening in terms of distributions. They’re not getting capital back. It’s like, I gave you capital 8 years ago, 9 years ago, 2017, 2018 vintages, and I’m not getting any capital back. So what the hell’s happening? On paper, it looks maybe the fund’s doing okay or it’s doing great in some cases, but where’s my money? And so that creates a little bit of wait-and-see kind of game on portfolio allocation. As we’re thinking through their re-ups, putting more capital into funds that they’re already actually put capital or putting in capital into new slots, into new fund managers that they want to put money into. They’re like, well, let’s wait and see. I want to get my money back or get some money back first before I redeploy it. Again, this is a little bit the haves and have-nots because we’ve seen, for example, a couple of top-end LPs in terms of returns that have a little bit the opposite problem, right? Because they are into funds that are performing extremely well. They actually are over that period and they want to actually redeploy. But to be honest, the average in the industry right now is a wait-and-see game. It’s like, I want to wait and see, which leads to what can only be characterized— I was hearing someone the other day, one of the top advisors in the LP community, saying this is the worst fundraising environment ever for venture capital. Not the last 20 years, 30 years, like ever, right? Since this became an asset class more institutionally in the late ’60s, early ’70s, Pulse Robo 2 as it was created, this is the worst fundraising environment ever. Oh, wow.   Bertrand And concerning TVPI, let’s not forget that typically it’s not mark-to-market. So the metrics in terms of TVPI, correct me if I’m wrong, you know, but the metrics in TVPI are based on typically the last fundraise. So if the valuation went down but there was no additional fundraise, we wouldn’t know by looking at the TVPI metrics. It will only be updated if there is a new Financing, equity financing, or an exit.   Nuno Yeah, normally most funds act like that. Some funds are a little bit more aggressive and do do mark-to-market, but normally funds would be conservative and say, hey, I’m being conservative, it’s whatever is the last known valuation of the company. And if there wasn’t a priced round, it’s a little bit more obscure than that, right, Bertrand? Because it might actually be the company has raised money on a note, or either convertible note or a SAFE note, and that wouldn’t count as a priced round. So I would say actually, even if it was a cap that’s below with a significant discount, I won’t recognize the assets as a down round. I won’t recognize the asset with a lower valuation because formally it wasn’t a price round. So it’s on the one hand conservative, on the other hand, it’s only relating to price rounds or exits to your point. So it’s sort of, you can be like, hmm, well, we opt to do that because we think it’s actually the most conservative route. Mark-to-market is extremely difficult to do. And who would do the mark-to-market for you, right? It’s like it’s some valuation firm, et cetera.   Bertrand I’m not saying a mark-to-market is easy, but I’m not sure I would call using the last valuation something conservative in the context that most startups will fail. So it’s not clear.   Nuno Well, in some cases it is, some cases it’s not, right? Depends on the startup situation, to be honest. Yeah, yeah.   Bertrand But yeah, at least that’s how it’s done. So for instance, to evaluate the impact of the SaaS apocalypse, it’s tough to know. We will have on the private market. I mean, we will see that in a few quarters. Because if companies still exist in that environment, if they still do additional truly price rounds after that, that’s when I will start to know.   Nuno I mean, just to share a little bit more data, like VC fund close time stretched to 15 months. Basically, it’s just taking a long time to raise money. It’s taking a long time to do your first close, get your fund running. When entrepreneurs complain to me that their fundraising is difficult, I always say, you have no clue how difficult it is compared to ours. First-time funds have collapsed. We had some numbers that only 77 first-time funds actually closed. I assume this is in 2025 versus 215 in 2023. So that’s a huge number. We did some internal analysis on our side and we did some analysis that emerging fund managers, emerging fund managers are normally people that are in their first one or two funds. Basically emerging fund managers gained some ground until 2017. Reaching by then a slice that was 63.7% of all capital raised in 2017. But since then, the capital deployed to emerging managers has been largely reduced to actually 24.2%, right? So it’s gone from 63.7% in 2017 to 24.2%. So this has been a culling of sorts on emerging managers and almost like a slaughterhouse of emerging managers. Compared to previous situations, which is obviously incredibly concerning if you’re an emerging manager starting your VC firm, et cetera, et cetera. So really tremendously problematic for those. We think capital’s not leaving VC. I think we see a lot of the institutionals saying— there’s some numbers as high as 33% of institutional investors plan to invest more in venture in the next 12 months. So I don’t think capital’s leaving VC. I think it’s really concentrating. We’ll come back to the concentration issue later in the episode. And part of that concentration comes from a topic that has been widely spoken in venture capital recently, which is differentiation. How do you differentiate in venture capital if you’re talking to a limited partner, right? How does my firm differentiate versus the firm next to mine? And that’s incredibly, incredibly challenging. Bertrand, what are your thoughts on that?   Bertrand Differentiation is always a question. I mean, if you’re an entrepreneur, Typically, you think fully about the best possible partner for your stage and for your type of business model. You want a VC who understands fully your business model, because if they don’t, then it’s going to be troubled down the line. But that’s true that another piece of the puzzle is that the best VCs help you get more visibility in terms of achieving potential customer deals, in terms of attracting the best talent. And that’s where VCs’ brand names can help. If you can say you have backing by some of the top, most visible names in the industry, and usually these are the mega funds because others have trouble to be as visible, then they have some sort of unfair advantage compared to others. So I can see that there is some level of concentration happening naturally, especially in the later stage from Series B onwards.   Nuno What Really Matters: Performance… Returns Yeah, I mean, we did some analysis internally about What are the top funds that invested in the top performing companies in early stage, Series C, Series A? And we looked at it by size of fund and the top performing normally are funds below $100 million, but in some cases very closely followed by funds between $100 and $500 million. And actually funds above $500 million, so $500 million to $1 billion and then $1 billion and above are actually tremendously underperforming. So this notion of the industry that says, well, the mega funds still see The top investments early on, because they still deploy in Series C and Series A opportunistically, in some cases even spray and pray if they have their own incubation and acceleration programs, is not true. Actually, we verified that over the last 12 to 13 years. It is not 12 to 13 years in vintage, right? So up to a 2021 vintage fund. So we went basically 12, 13 years back from there. And it’s not true. Actually, the most performing are 0 to 100 and then 100 to 500. And as I said, there’s 100 to 500 in a couple of years actually are a little bit better. Than the $0 to $100 million ones. So that’s the first thing that’s a conclusion. And actually, that’s not shocking. If we remember back in the day, Kleiner Perkins used to raise funds up to $600 million, Benchmark raised their $425 million funds. It seems like the sweet spot for a VC fund would be around $500 million at the top end, like maximum. And now somehow people are saying, well, I’m raising a $3 billion VC fund. It’s like, well, it can’t be a VC fund. The return profile is totally different, right? You can’t deploy that capital just based on early stage investing. And by the way, you’re not seeing the guys at early stage, all that you’re seeing, you’re going to make your returns in mid to late stage, right? Back to what we said at the beginning of the episode. So there’s a little bit of the haves and have-nots there. The big guys are raising more and more money, but they’re no longer venture capital. And I think limited partners that are a little bit more evolved, that are a little bit more conscious of this, that have been in the market longer, are realizing that shift. So it’s like if they want to have the alpha of venture capital, they need to deploy to the sub-$100 million funds or the sub-$500 million funds, right? That’s where they need to actually focus their VC capital. They can still deploy to mega funds, but they’re deploying to a different asset class. They’re deploying to a private equity, mid to late stage asset class, which looks maybe a little bit more like a growth fund or something like that. The second part of differentiation is the honest truth is most VC funds are like, I have proprietary network access, right? I’m ex-Stripe or I’m ex-Google or I’m ex-Facebook or whatever, and I have access to that. I mean, we know proprietary networks from that standpoint are no longer true. The whole thing that created Silicon Valley back in the ’70s of what I used to call the country club deals where there were a few people coming out of the big companies, the Fairchilds of the world, later on the Intels of the world, et cetera, et cetera, that made some money along the way that sort of bootstrapped their next companies, were well-known quantity to the existing VCs and raised money relatively easy on ideas, that doesn’t work anymore. Someone was telling me the other day one interesting thing that I wasn’t quite aware of, a lot of it had to do with the NDAs. I don’t know if you knew this, Bertrand, but like the fact that in California, it was sort of the Silicon Valley community sort of imposed this, we don’t sign NDAs thing and Boston continued signing it. And this whole NDA enforcement issue and non-compete, actually not the NDA thing, but more strongly that California did not enforce non-competes. I could leave Fairchild and start a company that magically was doing something that could be considered competitive to Fairchild. And that was sort of part of the acceleration actually of venture capital in California versus, for example, Boston, which was sort of hand in hand at the beginning.   Bertrand Yeah, I mean, I’m a big, big believer in California success coming from not enforcing or banning non-compete agreements. I think it’s a key part of the game. If you lock people into not doing something similar in the next 6 months to 24 months. And the industry has always been moving fast. So this is a significant time where you are blocked to do something very similar. I think it was really an issue. So I think it’s a key part of the game and it has been there. I don’t know how it started, but I think that non-enforcement of non-compete has been a key part of the success of California. I’m actually pleased to say that Washington State is going in the same direction. They are just signing a non-compete ban. And you might remember that at the federal level, I think in 2024, there was also a ban that was put in place to ban non-compete, but this has been reversed by the courts. So this is not there anymore. So that’s why we see a state like Washington State putting their own ban, and we might see more state by state moving in that direction. I think it was not helping at all, this non-compete. I mean, there is obviously stuff that needs to be done, like you cannot steal secrets, you cannot steal IP.   Nuno Yeah.   Bertrand Even stealing employees, there should be some restraints. We need to find the right balance, but you have to be careful there. That was key for the success of California, and I’m glad to see that this is a trend that’s going to go beyond California. And I hope most states will have a ban on non-compete.   Nuno Maybe just to close on the differentiation process, two things. One, I think there’s this notion When you talk to some LPs, that seems to be a little bit ingrained, some LPs that prefer specialized funds. We’ve also done some significant analysis internally and have talked to a couple of datasets other than our own, or people that own datasets other than our own, and the feedback has actually been not so fast. Actually, generalist funds over time cannot perform specialist funds. There seems to be a little bit of a sweet spot around generalist funds. We like to call ourselves multi-specialized at Chameleon, but ultimately from the perspective of specialized versus Generalist funds, the picture’s not as clear as specialized funds outperform generalists or generalists outperform specialized. We’ve seen there are pockets where actually generalists outperform specialized, in other pockets where specialized of a certain size can outperform generalists. So that’s one topic on differentiation that is a little bit broader. And then the final topic on differentiation, it’s really an industry that hasn’t innovated dramatically on where it creates the most value, which is really the picking stage, right? So it’s having great deal flow, very optimal, productive, efficient due diligence with very few resources and the ability to then get into those deals. That’s where most of the value is created. And then hopefully liquidating the asset if there’s an opportunity to do so at the right time, either through secondary trade sales or an IPO or something else. And what we’ve seen is the industry has innovated very little. I mean, the only thing I could point out in terms of core innovation at the top of the funnel has been the creation of the mega funds, the well-known funds, right? Like a16z, Union Square Ventures, et cetera, et cetera. But there needs to be more innovation on that cycle. And that’s why we certainly at Chameleon believe that the future is to have quant and AI-native VC firms that develop their own tooling, their own platforms. We have Mantis in our case that allow you to have this unfair advantage in how you source deals and how you do due diligence, how you get into the deals, et cetera, and how you take it to the next level. And we think that’s the beginning of the next stage is that the industry becomes more tech-enabled, shockingly enough, an industry that has made all its returns on tech or almost all of its returns on tech. That we need to be more tech-enabled ourselves. But I think the writing is on the wall there, and that will be a source of differentiation certainly over the next 3 to 5 years.   Bertrand One thing the industry has innovated somewhat and maybe could innovate even more is providing liquidity beyond trade sale and an IPO, because it’s clear that if VCs want more liquidity without waiting 18 years, you need that liquidity at different stage, not just when it’s time to do an exit, a full exit for the business. And for employees as well. I mean, it’s one thing to stay for a company for 4 years, which is your typical vesting. Maybe you extend that to 6 years, to 8 years, you have a great time at the company. But to think that maybe you have to stick around for 15 to 20 years in order to get liquidity on your stock options. I mean, that’s too much to ask for most people. I mean, people have a life, they have other things to do, other plans, they might want to move, they come at a different stage of life. So you need to provide them liquidity. The new game is we are not going to exit until 15 to 20 years, else it’s truly unfair. It’s not just unfair, but people will say, you know what, I’m going to go across the street, go work for Amazon or Google. I will have RSUs at best regularly that are liquid, and why bother? I mean, we need to find pathways to liquidity for both investors but also employees. There has been a change in that direction, but I think we need more of this change, and maybe not just reserved for the absolute biggest, most successful companies like OpenAI or SpaceX, but also us as well. Hopefully we can find a way.   Nuno Well, now we have these AI companies that actually grow so fast that they will IPO in one year. Now, isn’t that what’s going to happen? They raise They raised $500 million in Series C or $1.4 billion in Series C, and they’re going to IPO in 2 years. No? Is that not the new reality? I’m being facetious.   Bertrand At the same time, I mean, there are rumors that some of them are going to IPO this year. I mean, we talk about OpenAI, about Anthropic. I mean, OpenAI is quite old, but Anthropic is a relatively new business, quote unquote. So I think it’s a good time.   Nuno The Mega Fund Question So maybe it will be true after all. Moving to the next section, are mega funds still venture capital, Bertrand? Are they still venture capital funds?   Bertrand Yeah, I guess venture capital is a term that can encompass from small to very big funds. I truly don’t know. I mean, once you reach a growth stage, are you truly a VC fund? I don’t know. I think some of these definitions are kind of arbitrary from my perspective. What is clear is that you as a business need different providers of capital. And as we just discussed, you as a business, probably need to keep going and stay private for longer. One reason being, again, there is a tremendous cost to being a public company. There are some true strategic disadvantages. And at the same time, just practically, I mean, you need to get bigger and bigger in order to have a chance of a successful IPO. So you cannot just go IPO at a $500 million valuation. I mean, that’s like committing suicide, at least in the US market on NASDAQ. So my point is, you truly have no choice. You need to extend and If you need to extend, then you need to have capital providers that are there at later stage and therefore have more money. Is it still true venture capital? Is it true venture? I don’t know. At some point, it makes sense that from the startups to the capital providers, everyone adjusts to a reality where the life cycle is getting longer.   Nuno We don’t think it is. We don’t think mega funds are venture capital. We have actually some data that shows that they’re not in terms of actual returns. The alphas you can generate, the IRR that you can generate is actually not comparable. We did some analysis again with some of our datasets and from 2012 to 2022, so that’s the datasets that we used so that we had actual distributions and stuff we could take into account and so on and so forth. And looking at IRR, just to share some numbers in terms of IRR over those 10 years on sub-$100 million funds versus above $1 billion funds, the differences are incredibly stark. And this is true for global and US IRR, right? So just to quote some numbers in terms of average, sub-$100 million funds, global IRR of 22.9%, US IRR of 21.6% versus above $1 billion, 9.1% and 9.0%. Median IRR, if we just looked at median, 7.3% and 16.6% for sub-$100 million funds, 7.5% and 8.1% above $1 billion. Top quartile IRR, sub-$100 million, 31% versus 30.4% US IRR. And then above $1 billion funds, 14.7%, 15.5%. So it’s very clear if you sort of cut this in different ways, averages, medians, top quartiles, et cetera, over all these years that sub-$100 million funds are in a very different asset class than above $1 billion funds. They’re in different alpha that you can generate and so on and so forth. Now to the point you made, Bertrand, I don’t fully disagree with the point you made of the bigger funds should become bigger. I just think they’re becoming different things. Now, again, some of these funds will hide under the facts like, well, wait a second, we have all these assets under management, but they’re over different funds. Sequoia, we’re still raising small early-stage funds, $500, $600 million funds. And then we have larger funds for growth, et cetera, et cetera. Andreessen Horowitz, a little bit less clear what they’re actually doing. We heard that they’ve raised $15 billion across funds. I’m not sure if that’s the exact number at the end of the day. But the point is, if I’m a multi-asset class manager, like early growth, et cetera, et cetera, then it still applies what Nunu is saying. I’m still going after the $500 million, $600 million early-stage funds. Well, not so fast, right? Because you still have all this capital with managing general partners that are maybe across funds for which their incentives in particular, both carry and management fees are coming from the larger funds. Et cetera, et cetera. So there’s necessarily conflicts of interest. In many cases, the funds are just straight up big, right? And so they are above a billion. And so I don’t think a lot of these guys are in early-stage investing anymore, right? It may appear that they are, but I don’t think that’s where the returns necessarily are going to come from. And so if you are a limited partner, if you’re looking at your asset class allocation, again, you’re absolutely free to put money into mega funds because that’s the kind of asset class you want to play in. In terms of a blended private equity asset class that has a little bit of growth, a little bit of whatever, or actually a lot of growth, a lot of late stage, and maybe a little bit of early stage. And I want something that’s a little bit more blended, right? But if I still want the alpha venture capital, I need to deploy to funds that are early stage, right? And that’s like up to $100 million, up to $500 million. I think that’s my two cents on that topic. We see crossover things coming around, like guys who do both public and private markets. Again, that starts feeling a bit like a hedge fund. A lot of these funds have also become RAs, as we discussed earlier. So I feel the writing’s on the wall. The mega funds are going more and more after either some mechanism of edging or a mechanism that’s a little bit more blended in terms of private equity than classic venture capital.   Bertrand Yes, I think a few things. One, if you’re an LP, I can imagine that dealing with multiple $100 million funds might be more difficult. You, you need to know the partners, you need to have some background, uh, visibility. You need potentially to change regularly of VC investments. So I can see some level of simplicity if you just focus on the bigger ones, especially if you have a lot of assets you have to put to work. Another piece of the puzzle, I would guess that the bigger funds are able to return money faster because they are at later stage of the cycle. So instead of that 15 to 18 years, maybe they are more in a 5 to 10 year range, while the smaller funds being there more early might be the one who are taking longer to deliver. So I can see that Yes, there is an IRR picture, but there is also time to liquidity that is not the same. So that can probably also influence. And in terms of crossover PE hybrid model, I mean, for sure we have seen some of the public equity investors doing crossover, meaning going into private equity firms like Coatue, like Tiger Global and others. And for companies that are preparing for IPO, there is a lot of value to work with these firms because they have very good visibility and understanding of the public markets. And their presence in the cap table is also a sign of quality, typically for public market investors. So there is a lot of value and logic for them to be there on both sides of the puzzle. But again, the fact that firms keep delaying IPOs, that the market is not so much startup-friendly, makes this model a bit more difficult. But personally, I think there is value there.   Nuno Yeah, I think on the mega fund, just so that I’m not boo-booing everything, I mean, but there’s definitely angles in terms of the asset class that make a lot of sense. And there’s the scalability of the model. The ability to go after Series B, Series C, as well as mid-stage, as well as late-stage, even secondaries over time, to your point, in some cases even public equities. And that level of skill I think matters. We’ve also seen, as we’ve known, we won’t mention any brands, but people will know who they are, that late-stage hedge funds and investors, even if they’ve done okay-ish in growth in private equity, don’t necessarily do well in venture. So it’s clearly a very different asset class, right? So once you start getting venture teams together, The returns are not quite the same. Actually, sometimes they’re not even quite the same as the growth investments. So clearly they’re very good at the growth side, but not so good in early stage. But definitely there is a case for it. The Case for Smaller…Rightsized Funds But if we switch gears maybe to the small, or I would call right-sized funds, maybe just to quote a couple of numbers and then open up the discussion. Small funds do seem to outperform larger funds. There’s a lot of data in the market that shows some of that dynamic outperformance frequency. All the Very historical numbers from Cambridge Associates from 1981 to 2010. 19 out of 30 vintages were won by sub-$150 million funds. We did our own analysis as I was sharing before. Funds between $0 and $100 won most years between around 2010 and 2021. And the years that they didn’t outperform in terms of investing in the top-performing companies in early-stage Series C, Series A, they were outperformed by the $100 to $500 million funds. The $500 to $1 billion funds and $1 billion or above were never even in the same league in terms of performance, of having identified those top performers in terms of quantity over those early-stage investments. Top 10 funds by vintage, 2004 to 2006, 2016 numbers. Top 10 funds, 73% were sub-$100 million. 2004 to 2016, top 10 funds by vintage, 73% of those were sub-$100 million. So there seems to be a little bit of a case that actually smaller funds, sub-$100 million, sub-$500 million in some cases, are outperforming the larger funds over time. Now, these funds are complex in and of itself. The positive of it is small fund GPs like myself, we are deeply invested in our own funds. We’re not there to just make management fee monies. I mean, we’re not making $1 million, $2 million a year in management fees of salary ourselves, like some of the larger funds. So we are there to really get the carry and be less focused on management fees. And so I think there’s a little bit of alignment around that and really taking that kind of perspective on portfolio construction and liquidation, being also more aggressive on the individual time that we spend with our startups. On the negative side, obviously a lot of these smaller funds, not the case of Chameleon, but others out there are single GPs, very little teams or very small teams. And so it’s sometimes difficult to actually do a lot for portfolio companies as well. And this is where the mega funds, for example, a16z notably would say, hey, we have 600+ people that can support you, right? On market development, business development, communications, talent recruiting, all this stuff. Question mark whether that’s the right way to do it in terms of operating model, if technology is not a better way of supplying that value back to your portfolio companies, or if there’s no better way of doing it. But still, that’s one of the appeals of actually dealing with a larger mega fund if you’re a startup, right? That they will have the resources, also the financial resources to put more capital in you. But also, again, if there’s entrepreneurs listening to this right now, and hopefully there are, it’s a two-edged sword, right? Because if you have Andreessen Horowitz putting money in you, or NEA, or General Catalyst, or whatever, putting money in you on a Series C and then not doubling down on the Series A or the Series B, there will be questions, right? Because like they have the capital, they have other funds, so why the hell are they not putting more money in? Um, so, so it’s a little bit of a two-edged sword.   Bertrand Yeah, I think that one is a pretty big one. And on top of it, as we discussed, some of these big firms have multiple funds managed technically by different teams. So you might have convinced the early-stage teams, they have investors, they’re happy, but you don’t convince the growth-stage firm. As you say, it might raise questions because people might think that there is some communication between the early-stage team and the growth-stage team. So why the heck are they not deciding to invest? And as we also discussed, even worse possible situation, what happens if the growth-stage team has invested in your competitor? It’s even more trouble. So I think trying to understand how firms behave, what’s the reputation of the firm, what’s the reputation of the partner you are working with, I mean, can have tremendous importance and impact. When it’s time for you to work with a firm.   Nuno Indeed. I mean, at the end of the day, we still believe that the smaller fund— we at Chameleon discuss the notion that our limit should be $500 million per fund, right? And that’s the logic of it. We think that model is the model that works well in venture capital. We do recognize, as I said before, why mega funds keep raising more and more money, right? It becomes a harm’s race at that end of the market. As I said, probably a slightly different asset class, or if not a significantly different asset class as well. So seeing a little bit both sides of the market, I mean, we often compete with the mega funds, but honestly, a lot of the mega funds are kind to us and they let us in. And this whole notion of elbows out, we haven’t felt it that much in the market. And people see our value at the table. And in many cases, I, I do see the larger funds more and more seeing the value of smaller funds coming in on the same rounds and even in some cases co-leading early stage rounds like Series C. So it’s not like elbows are out everywhere across the board. So I don’t mean to say this is like an all-out war between small funds and big funds and the small funds need to win or the big funds need to win. I think actually there’s a lot of potential for coexistence. My point is more that the asset classes and the returns are quite different over time, and that’s how I would think through it. And if you’re an entrepreneur, you should think about that as well, right? What are the implications of taking money from certain funds versus others in terms of the expected returns, expected time allocated to you? For example, if you’re not doing very well as a as a company, right? Will the big funds spend the same amount of energy on you if you’re not doing great and all of that? So it’s a little bit sort of a beware, open your eyes, both for limited partners and for startups. What do you actually want, right? What do you want from your VC firm if you’re a startup? And what do you want from your VC firm if you’re an LP?   Bertrand I must say, as an entrepreneur, uh, a board member, I have seen some situations where the bigger funds are actually trying sometimes to elbow out the existing investors. Like, uh, we have that much money to put to work, we cannot do less. And you’re like, yeah, but I don’t need that much money. And then they’re like, okay, just don’t let your existing investors do their pro rata. I don’t think it’s great because an entrepreneur, if your investors, your VCs, trusted you earlier stage when it’s more risky, and when it’s becoming less risky, you don’t give them the right to their pro rata because you have to let this big guy come in. That’s not great. Or even if there is not this pro rata issue, when an investor tries to put more money to work than it’s really necessary, it’s also not a good idea as an entrepreneur to take more capital than you could use. It will dilute you more, it will set higher expectations in terms of valuation, it will push you to use that capital faster than maybe would be reasonable. So I think that’s something you want to be careful with the bigger funds. So don’t talk to funds that are in some ways beyond your stage and try to make it work in that context. Or don’t accept to have your strategy change dramatically for no good reason by funds that just want to put too much money to work in your business. And that for me is surprising because it should also be in their best interest not to invest in businesses that are not ready to accept that much capital. But as we have seen, there were in the past some funds that believe that capital is a moat. Was a good idea. So hopefully, I guess we’re a bit behind that. But yeah, I would say entrepreneurs, be careful, find partners that are the right partners for you at your current stage. Sometimes some big names look great, but at the same time, if it comes with a lot of issues, from too much capital to also taking the risk that these partners don’t understand the stage of the business you are in or your industry, Just be careful. There is a lot of value to have firms that are very focused on your stage, on your industry, are finely attuned to that situation.   Nuno What Comes Next? Maybe to end in terms of sections, what comes next? And maybe we can come up with some predictions that are a little bit provocative on what’s going to happen to the market. You, if you’re listening to us, feel free to interact with us on LinkedIn, on X. If you have our email address, shoot us an email as well. We’d love to hear from you if you think these are the right predictions or if we’re totally off. Maybe I’ll throw in the first one, Bertrand, and we’ll go one by one. So we’ll each put one at the table and see where we head. My first one is that we’ll have a huge culling of VC investors. We had this rapid expansion of the VC asset class with arguably at least tens of thousands of firms globally, maybe even over 10,000 in the US. I think we’ll have a culling and the culling will continue and we’ll have several firms sort of getting eliminated over the next couple of years that will have either because they’re having tremendous difficulty doing their first close in their next fund, or the returns are not there, or it’s a firm that has done 3, 4 funds, but for some reason the returns have just gone out of whack in the last few years during the bull years. And so therefore, actually they can’t justify to raise more funds out there. So I predict there will be a significant elimination of active firms in the next at least 2 to 3 years. So maybe by 2028, and we’ll be below, I don’t know, 30% of number of active firms that we are today. The other side of it is I do think if we look beyond that, 2029, 2030, and so on, we’ll have the reemergence of not micro funds, but nano funds where people will start deploying capital very, very early and writing small angel checks, but doing it in a way that it’s sort of not this cottage industry that we’ve had of angel investors. So I think angel investment will be disrupted by people that will use more and more of the AI toolification out there to actually manage their portfolios of 10, 15, 5K investments in a way that is a lot more professional, creating sort of an advent of nano funds.   Bertrand Yeah, makes sense. On my side, in terms of prediction, I think there is a possibility that the mega fund model keeps expanding and looks more similar over time to some PE models. So do we have the top 10 VC firms that look more like a Blackstone than a Kleiner Perkins or Sequoia used to be? That for me will be an interesting question and development. I think that there is some possibility that it keeps going in that direction. A lot of incentives are pushing things that way.   Nuno My next prediction is that DPI, distributions to paid-in cash on cash, just cash back, will become essential for limited partners. I think TVPI, total value to paid-in, that also has in there, as we just said, paper valuations. There’s a lot of disbelief now around the TVPI metric if there isn’t distributions going alongside it. For those who, again, don’t know what TVPI is, it’s total value paid in, but it also includes DPI. So it’s cash on cash component plus a remaining valuation to paid in, an RVPI. And the problem is the RVPI really, in reality, it’s that kind of on-paper valuation that never gets attributed. I think LPs, they’ve seen the writing on the wall and they’re like, dude, just show me your DPI numbers. I don’t care about TVPI. Some LPs will still ask about TVPI just to make sure that the rest is sort of looking in order. Like, show me the money, show me the cash. Actually, it’s not money, show me the cash, right? I want money back.   Bertrand But that’s an issue. I mean, if you’re supposed to raise financing every 3 or 4 years, good luck getting DPI to show for that. So you need to be at least on your third fund in order to be able to show DPI, I guess.   Nuno I mean, my corollary to that, Bertrand, is if you allow me just to have a corollary kind of prediction, is that we’ll see certainly for funds like $50 million and above, $100 million, $200 million, et cetera, even increased concentration, right? I really need to have anchors that believe in me over time. And we might start having, again, the advent— we had it some decades ago, the advent of cap table kind of VCs, right? Like Sutter Hill Ventures, right? Where they’re not really raising funds anymore. And so we might have the advent of that, that we’ll have structures that are created that have more permanent capital allocated to them, or at the very least more concentrated capital by very few players.   Bertrand Interesting. Me on my side, as I shared before, I believe secondaries are, are important and here to stay. Um, in the past, some could argue, is it a distress signal or something? I, I don’t think it’s true anymore. In a world where your average startup might take 15 to 18 years to exit through M&A or IPO, we need to have other options. For funds, for employees, they cannot be expected to stick around for so long and have no liquidity. I mean, it’s just pure madness. It’s just bad alignment at some point to do that. So I think secondaries are becoming the third liquidity pathway for VCs, for employees, and it should be more and more a key part of the game, a key infrastructure in the VC/startups tech industry.   Nuno I mean, on specialized versus generalist funds, I believe we’ll continue seeing the coexistence of those two models where the specialized funds will in many pockets actually outperform generalist funds, but where we’ll continue seeing that the large franchises, the tier one franchises will likely be generalist funds. I mean, we just saw it in the cycle. The AI cycle went upon us. We had a 2021 fund. We could easily adapt and go into AI and figure out that AI was growing very fast. I mean, if you have an ultra-specialized fund and that’s your remit and that’s the only thing you can invest on, very difficult to change even during our investment period. I will put a caveat on that. We don’t call, for example, ourselves at Chameleon generalist. We call ourselves multi-specialized because our scoring models for the verticals that we track are specialized within Mantis. Because the partnership is specialized, we all focus on different areas. And because we have the Kin network that allows us to tap into that level of expertise, Again, I think the world will be specialized coexistence. Some pockets specialized will do very well, certainly on the smaller fund size, but the big franchises will likely look a little bit more generalist. And as I said, multi-specialized from our perspective is the future. We’ll start seeing more and more funds that are multi-specialized like ourselves. Do you want to talk about AI and how it’ll distort the metrics? No.   Bertrand Yes. I think AI is an exciting moment in the tech industry. It feels in some ways that the same way we had a big distortion coming with COVID and work from home in 2020, 2021. 2021, where suddenly everyone and their mother will build a SaaS company or invest in a SaaS company. AI feels a bit of the same. I mean, to be clear, I truly believe it’s deserved. I mean, we are facing a dramatic shift in how computing is being done in terms of value you can get from software. So at the same time, AI will probably distort this matrix for a long time. We clearly see a split where investments are going, in what startups are being created. So I think, yeah, we will see some distortion. And we know that maybe 50% of all deal value is going to AI in 2025. We have seen single rounds reaching 40 billion, like to OpenAI. We have seen, as you discussed, some seed stage investment of 400 million. So AI investing and AI startups are definitely a beast on their own. And will distort VC metrics for a long time. And we might need two sets of metrics in parallel, you know, AI versus everything else. So that would be an interesting bifurcation in the industry in some ways. I would say it’s fair to separate AI versus non-AI. We reach a point where it’s two different beasts.   Nuno Conclusion So in conclusion, AI has changed the world and it’s changing VC as well, as we discussed earlier in the episode. We have a tremendous momentous occasion for the asset class where venture capital is really bifurcating into very large funds, which no longer are in venture capital or seemingly may be distributed between different asset classes, and the smaller funds, sub-$500 million and sub-$100 million, that keep having the better returns, but also with much smaller scale. We’re seeing a culling of the industry where the industry is definitely getting smaller and smaller and more concentrated at both ends, number of VC firms, as well as a number of limited partners per fund and the interest that some of these limited partners have of being more and more concentrated in their own portfolio allocations. And last but not the least, the discussion around specialized versus generalist, where it seems like there’s some clear winners on some asset classes, on some sizes, in some industries, but on others, there’s other kinds of winners. And so maybe the future is multi-specialized, as I framed at the end. Thank you so much for listening. If you want to check us out and if you want to comment, feel free to send us messages on X, LinkedIn, to both myself and Bertrand, as well as send us an email. Thank you so much, Bertrand.   Bertrand Thank you, Nuno.

The SpaceX IPO will likely be the largest public offering in history... But before you get excited, Nicole breaks down how the IPO machine actually works, and why some of the smartest people in finance say the system is rigged against you. Nicole walks through the full IPO process step by step: what underwriters actually do (and what they charge for it), how the roadshow and book-building work, and why the price you'll pay on IPO day is not the price institutional investors paid. She also covers what SpaceX employees need to know right now about their equity, stock options, RSUs, lockup periods, and the tax surprises that can blindside you before you sell a single share. Then, Nicole shares the framework she uses to evaluate any IPO, including the two sections of the S-1 prospectus most retail investors skip, and explains how you can get in on SpaceX before the IPO. Check out Nicole's financial literacy course The Money School  Find a Financial Advisor or Financial Coach from Nicole's company Private Wealth Collective Watch video clips from the pod on Money Rehab's Instagram and Nicole Lapin's Instagram  Here's what Nicole covers today:  00:00 Are You Ready for Some Money Rehab?  00:04 The SpaceX IPO: Just How Historic Is It?  01:08 How the IPO Process Actually Works  02:12 What Underwriters Do (and What They Cost)  03:04 The Roadshow and How IPO Pricing Works  03:45 NYSE vs. NASDAQ: Where Will SpaceX List?  04:25 Why Companies Go Public  05:14 What SpaceX Employees Need to Know About Their Equity  06:00 Lockup Periods Explained  07:06 Three Things Every Employee Must Do Before an IPO  08:06 Is the IPO System Rigged? Bill Gurley's Argument  10:00 The Figma Example: How Retail Investors Got Burned  11:19 How to Evaluate Any IPO Before You Invest  13:27 Watch the Lockup Expiration Date  14:09 Tip You Can Take Straight to the Bank All investing involves the risk of loss, including loss of principal. This podcast is for informational purposes only and does not constitute financial, investment, or legal advice. Always do your own research and consult a licensed financial advisor before making any financial decisions or investments.

With Tax Day right around the corner, Laura and Kevin take a hard look at a question a lot of high earners quietly avoid: if you're making great money in tech, why aren't you actually on track to retire?Haley Gray, CFP®, joins the pod to break down the gap between income and real wealth. She explains how strong salaries can create a false sense of security, especially when taxes, lifestyle creep, and equity compensation complicate the picture more than people expect. The conversation digs into how rapid income growth subtly reshapes spending habits, often locking people into a higher cost of living before they've built a solid financial foundation. Haley also unpacks the realities of equity comp, from RSUs to stock options, and why having too much tied up in one company can create risk that's easy to overlook when things are going well. With a practical, no-nonsense approach, Haley walks through what “retirement readiness” actually means, how often people should be checking in on their progress, and the moment of truth many face when they finally run the numbers.The big takeaway: making good money isn't the same as building wealth. But with a few smart moves, starting now, it's possible to get on track faster than most people think.Haley Gray is a CFP® professional and Financial Advisor at Stellarix Group, where she works with professionals in technology and other fast-paced industries to navigate complex financial decisions with clarity and confidence. Her work focuses on retirement planning, tax strategy, and long-term wealth building, with an emphasis on areas that are especially relevant for tech professionals, such as equity compensation, variable income, and concentrated stock positions. Haley brings a modern, practical perspective to financial planning, helping clients simplify complexity and make smarter decisions with their money over time. She is known for her practical, education-first approach, helping clients focus on what actually matters and make confident financial decisions without unnecessary complexity. Her goal is to help clients build strong financial foundations that support both their careers and their long-term goals.Haley Gray is a registered representative of and offers securities and investment advisory services through qualified MML Investors Services, LLC. Member SIPC. OSJ: 2000 S Colorado Blvd, Tower 2, Ste 800, Denver, CO, 80222-7952, (303) 692-8183. The Stellarix Group is not a subsidiary or affiliate of MML Investors Services, LLC or its affiliated companies. CA Insurance License #4087390

With Exact Sciences stockholders officially approving the merger with Abbott on February 20, 2026, the Q2 closing date is fast approaching. For employees, this means unvested RSUs are accelerating, 401(k) holdings are shifting to cash, and a significant "tax cliff" is looming in 2026.In this deep dive, Clint Walkner and Mitch DeWitt break down the strategic financial moves Exact Sciences employees can make now to protect their windfall and minimize the IRS's cut.What We Cover:- The $105 Cash Payout: How the all-cash deal impacts your RSUs, PSUs, and ESPP.- The 2026 Tax Spike: Why accelerated vesting could push you into a higher tax bracket and how to "bunch" deductions to fight back.- 401(k) & HSA Strategies: Should you pivot to Pre-Tax or Roth during a windfall year?- Risk Management: How to handle the uncertainty of future roles and potential layoffs post-merger.- Charitable Giving: Using Donor-Advised Funds (DAFs) to offset your 2026 gains.Timeline of the Deal:0:00 Deal Overview: The Abbott/Exact Sciences Merger1:00 Updates: What's changed since the November announcement?3:43 Cash Deal Timing: Preparing for a Q2 2026 close5:12 2026 Tax Planning: Managing the "Windfall Year"9:04 Advanced Moves: Charity, DAFs, and Trading Windows10:43 Goal Assessment: What to do with the cash (Debt vs. Savings)14:12 Employment Risk: Liquidity and Emergency Reserves16:48 Next Steps: Coordinating with your Tax ProResources for Exact Sciences Employees:https://walknercondon.com/blog/what-happens-to-my-exact-sciences-stock-after-the-abbott-acquisition/Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ————————————————ADD US ON:LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

In this episode, we take a closer look at Employee Stock Purchase Plans and ask a simple but important question: are they worth the effort? Many people in tech see ESPPs during open enrollment, feel overwhelmed by the language, and quietly opt out. Why does that happen? Well, ESPPs sit in an awkward middle space. They are not large enough to feel exciting like salary, bonuses, or RSUs, but they are not simple enough to feel effortless. That combination often leads to avoidance.We discuss why companies offer ESPPs in the first place. Some want employees to think and act like owners. Some use them as a light retention tool. Others simply provide a convenient, payroll based way to purchase company stock. Not all plans are created equal. Some include meaningful discounts and lookback provisions that can significantly improve the math. Others are more basic and function more like a structured stock purchase program. Understanding the specific mechanics of your plan is critical. Blanket assumptions do not work here.We address one of the biggest sticking points, which is taxes. Many people fear making a mistake, especially around disqualifying dispositions. We clarify that a disqualifying disposition is simply a different tax treatment, not the elimination of the benefit. Even if taxes are higher, the discount does not disappear. We compare this to a 401(k) match. Taxes will apply eventually, but that does not make the match worthless.We also talk about multi year offering periods and how they can create hesitation. Long timelines can feel binding, especially for those already concentrated in company stock. The plan's timeline does not dictate personal behavior. You still have choices.Amy encourages you to move from optimization to intention. ESPPs are rarely life changing on their own, but when structured with a discount, they can quietly add value. The key is clarity. When we understand the plan and how it fits into our broader compensation and concentration picture, the decision becomes lighter and more intentional.(00:00) Introduction to ESPPs(00:57) Why ESPPs Get Ignored(03:11) Why Companies Offer ESPPs(04:44) What Makes a Plan Valuable(07:36)  Key Variables(08:48) Taxes and Disqualifying Dispositions(11:17) Multi Year Offering Periods(12:46) ESPPs vs RSUs and Other Compensation(14:21) Optimization vs Intention(16:21) How to Contact Thimbleberry Financial To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

In this episode of Journey Beyond Divorce, Karen McMahon sits down with Stacy Francis, CFP®, CDFA®, CES™, President and CEO of Francis Financial, to unpack one of the most complex and often overlooked aspects of divorce: executive compensation. When income extends beyond a traditional paycheck to include RSUs, stock options, deferred bonuses, and long-term incentive plans, the financial landscape of divorce becomes significantly more complicated—and the stakes much higher. Together, Karen and Stacy explore how these "golden handcuffs" function and why they are so frequently misunderstood, undervalued, or even missed entirely during divorce proceedings. They dive into how executive compensation is structured, where disclosure gaps tend to occur, and how to identify these assets through key documents like offer letters, vesting schedules, and compensation statements. Stacy also explains how marital versus separate property is determined using time-based calculations tied to the date of divorce, and why timing, vesting schedules, and tax implications can dramatically impact the outcome of a settlement. This conversation brings clarity to critical decisions, including whether to divide future vesting shares or offset their value with other assets, and highlights a common and costly mistake around who is responsible for taxes on RSU income. Karen and Stacy also discuss real-world complications like job changes, buyouts of unvested compensation, and what happens to these assets in the event of death or disability. Throughout the episode, they emphasize the importance of working with experienced legal and financial professionals who understand high-net-worth divorce and complex compensation structures. Whether you are an executive navigating divorce or a spouse trying to understand the full financial picture, this episode offers essential insights to help you avoid costly mistakes, ensure proper disclosure, and make informed decisions that protect your long-term financial future. Connect with Stacy: Website: https://francisfinancial.com/francis_team/stacy-francis/ Facebook: https://www.facebook.com/FrancisFinancialInc/  Instagram: https://www.instagram.com/francisfinancialinc/ YouTube: https://www.youtube.com/channel/UCjYgEJi2EhaCd1pL58V78iA?view_as=subscriber Free Gift:  We have seen first-hand the impact that a detailed Legacy Plan has on our clients and their loved ones. This experience inspired us to create our Legacy Planning Checklist. To make it easier, we've created a three-part Webinar which will take you through the checklist step by step to make sure you finish with confidence. Each session is hosted by Certified Financial Planners™ Stacy Francis and Natalie Colley, who share practical guidance, real examples, and tools to help you build your personalized legacy plan with clarity and confidence. Gift Link: https://francisfinancial.com/because-i-love-you-a-legacy-planning-companion/   Resources Mentioned in this Episode: Follow JBD on Instagram: @journey_beyond_divorce Book a Free Rapid Relief Call: http://rapidreliefcall.com Free Divorce Support Network Gift: https://divorcesupportnetwork.com/jbdpod

Kevin Koharki, MBA, PhD, is the founder of CAE Consulting (Capital Allocation Enhancement), associate professor of accounting at Purdue University, and expert financial analyst with a 20-year career — including M&A analysis — who consults with and advises Fortune 100 companies on understanding the true economic cost of stock-based compensation.The episode is sponsored by TenzingMEMO — the AI-powered market intelligence platform I use daily for smarter company analysis. Code BILLIONS gets you an extended trial + 10% off.https://www.tenzingmemo.com/3:00 — Kevin traces the origins of stock-based comp to the 1990s dot-com era; originally meant to conserve cash at startups and align employee incentives with shareholders.5:00 — The shift from stock options to RSUs and PSUs; accounting still at the expensing stage from 2002 FASB rules.7:00 — Why stock-based comp is concentrated in the tech sector, particularly Mag-7 companies — the very firms that don't need to conserve cash.10:00 — Kevin walks through the mechanics: 100 RSUs granted at $30, expensed over three years, but if sold at $90, the $60 gap never appears on the P&L.14:00 — Cash flow distortion: compensation paid in shares shows up as a financing activity, not an operating expense — inflating free cash flow.17:00 — Why employees don't truly become owners: tax liabilities force selling, and short-term vesting creates a “what's my vest date?” mentality.19:00 — The Berkshire model: Greg Abel buys shares with after-tax salary. No stock-based comp. Buffett's emphasis on intrinsic value per share.23:00 — Psychological toll: employees hired at the peak face crushing drawdowns; companies respond by issuing even more shares.28:00 — Real-world example: a company with $102B in operating cash flow shows $6.4B in GAAP SBC — but $7.9B just in tax withholdings. The tax cost exceeds the recorded expense.35:00 — Second example: 90% of a $26.3B share buyback was simply to offset dilution. True free cash flow drops from $46B to roughly $4B.42:00 — The private company test: “If you bought the whole company, you'd still have to pay those employees in cash.”50:00 — The IRS treats SBC as cash-basis: the $90 exercise price gets the deduction, not the $30 GAAP cost.58:00 — Kevin: “I just think there's kind of a mass delusion going on right now.”1:03:00 — Wall Street Journal coverage and Nvidia's disclosure change; the conversation is shifting.Podcast Program – Disclosure StatementBlue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm's employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

When I explain to advisors they likely will want legal advice regarding navigating their departure from their current firm, I sometimes hear a range of responses:“My buddy left the firm last year, and I'm just going to follow what he did.”“I'm already independent, so none of that applies to me.”“I made a transition 7 years ago, so I already have it figured out.”In reality, most advisors, regardless of their current affiliation model, have at least one (if not multiple) reasons to need such advice: non-solicits, non-competes, Reg SP, broker protocol, deferred comp, forgivable loans, RSUs, taking team members with them, etc.On this episode (#145) of the Transition To RIA question & answer series I explain why and how such legal advice is part of a typical transition.Come take a listen!P.S. Prefer video? You can find this entire series in video format on Youtube. Search for the TRANSITION TO RIA channel.Show notes: https://TransitionToRIA.com/when-do-you-need-legal-advice-as-part-of-an-ria-transition/About Host: Brad Wales is the founder of Transition To RIA, where he helps financial advisors between $50M and $1B understand everything there is to know about WHY and HOW to transition their practice to the Registered Investment Advisor (RIA) model. Brad has 20+ years of industry experience, including direct RIA related roles in Compliance, Finance and Business Development. He has an MBA and has held the 4, 7, 24, 63 & 65 licenses. The Transition To RIA website (TransitionToRIA.com) has a large catalog of free videos, articles, whitepapers, as well as other resources to help advisors understand the RIA model and how it would apply to their unique circumstances.

Company stock: one of the most confusing—and potentially valuable—parts of your compensation. From RSUs to ISOs and NSOs, learn what you actually own, how vesting and exercising work, and where people commonly make costly tax and risk mistakes. The key takeaway: equity compensation is often a great opportunity, but it's not simple—and without a clear plan around timing, taxes, and concentration risk, it's easy to leave money on the table or create avoidable problems.Find out more about Mike at https://www.mortonfinancialadvice.com and connect at https://www.linkedin.com/in/mwsmorton/

In this episode of ThimbleberryU, we dig into why tax season can feel particularly overwhelming for tech professionals and how to approach it with less stress and more predictability. We focus on the common sources of tax complexity, equity compensation and bonuses, and offer a simple framework for making tax season less dramatic and, ideally, boring.We start by exploring how tech income is rarely just a paycheck. When restricted stock units (RSUs), employee stock purchase plans (ESPPs), bonuses, or job changes are layered on top of a base salary, tax situations become more complex. These types of income show up in chunks and are taxed differently, often creating withholding gaps and surprises at filing time. Most payroll systems handle base salary well, but they may fall short when irregular income is involved.We walk through how RSUs are taxed at vesting, and how withholding often underestimates what's truly owed, especially for higher earners. ESPPs add another wrinkle: taxes are triggered when shares are sold, not purchased, and withholding is often absent entirely. And bonuses, while taxed as regular income, are frequently withheld at flat rates that don't match the recipient's tax bracket. This leads to confusion and contributes to the myth that bonuses are taxed more heavily.Throughout the conversation, we emphasize that withholding is NOT the same as actual tax owed, and that tax visibility (not perfection) is the real goal. We suggest starting the year by forecasting equity and bonus income, applying a rough tax rate, and comparing that to projected withholdings. If there's a gap, it's not a problem; it's a signal to adjust.We share real client examples, showing how a lack of planning around year-end RSU vests led to surprise tax bills. A few proactive steps, like setting aside cash when equity vests or bonuses hit, can prevent financial strain. We encourage creating a running file of key documents, such as vesting summaries, pay stubs, and equity sale confirmations, to simplify reporting and planning.Finally, we outline a system for turning tax planning into a repeatable habit: review compensation annually, capture documents in real time, run a mid-year check, and coordinate with financial and tax professionals before tax returns are finalized. The message is clear. Calm comes from process, not hope. With the right approach, taxes can feel manageable, even boring. And in this case, boring is a very good thing.(00:00) – Intro: Why Tax Season Feels Overwhelming(01:40) – The Hidden Complexity of Tech Income(03:00) – Where Tax Risk Typically Shows Up(04:00) – How RSUs and ESPPs Are Taxed(07:00) – The Bonus Tax Withholding Myth(09:00) – Estimating Tax Exposure (Visibility > Precision)(10:26) – A Real-World Tax Surprise Story(12:32) – Gathering Tax Documents Throughout the Year(14:45) – Managing Cash Flow from Equity & Bonuses(17:43) – Building a Repeatable Tax Planning System(19:17) – Final Thoughts: Calm Comes from Process To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Today's episode is for the woman who's doing well on paper…earning more, climbing higher, checking the boxes of financial success— and yet still wondering if she's making the smartest moves with her money. Because here's the truth: more income doesn't automatically mean more clarity, more confidence, or even more security.In fact, high-earning women often face a unique set of financial blind spots—from over-relying on tax strategies to holding too much company stock, to quietly navigating complicated power dynamics at home and at work. And those mistakes can be costly if we don't name them.To help us unpack all of this, I'm joined by someone whose passion for empowering women financially is unmistakable the moment you hear her speak—financial advisor Maggie Johndrow who is a partner at Johndrow Wealth.In this conversation, we talk about the quiet financial mistakes high-earning women make, how taxes can mislead our biggest decisions, what to know about RSUs and stock options before they surprise you with a bill, and the emotional—and practical—realities of being the breadwinner at home. Hosted on Acast. See acast.com/privacy for more information.

In this episode of ThimbleberryU, we dive into an increasingly common experience for those working in the tech industry: burnout. We begin by acknowledging that tech burnout is unique—fast-paced roles, unpredictable compensation, constant decision-making, and job instability combine to create chronic stress. Amy Walls shares how burnout shows up not only emotionally, but also financially, and how we can use financial planning to move from depletion to clarity and control.We explore how burnout rewires our ability to make decisions. Stress from long hours and mental overload shrinks our decision-making capacity. This leads to automatic, often reflexive spending as a way to cope—ordering food, shopping online, or subscribing to convenience services not out of indulgence, but survival. Many of us say we make good money, yet still feel stretched. Amy explains this disconnect through the lens of decision fatigue and lifestyle inflation as coping tools, rather than conscious choices.Then, we walk through Amy's Burnout Blueprint, a three-pillar framework for using financial planning to support mental and emotional wellbeing. The first pillar is intentional spending. We learn to distinguish between energy-saving expenses, like cleaning services or meal prep, and stress-coping spending that signals a deeper need for rest or support. We hear how small shifts—like outsourcing chores—can buy back time and change our relationship with money.The second pillar is career pacing. Amy shows how financial clarity gives us room to pause, reassess, or even take sabbaticals. Instead of being chained to the next RSU payout or promotion, we can model what “enough” looks like and make career decisions from a place of health, not fear.The third pillar is structured downtime. Real rest requires more than intention—it requires the freedom to disconnect without guilt or financial worry. Whether it's a full sabbatical or just a microbreak, planning for rest helps rebuild energy and perspective. We also look at underutilized workplace benefits that can support recovery and reduce costs.To wrap up, Amy leaves us with a powerful reminder: burnout isn't a personal failure—it's a mismatch between demands and energy. Small, intentional changes around spending, work, and rest can restore control and support our overall wellbeing. To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

Navigating Common Tax Mistakes and New Tax Laws for 2026In this episode of Techie Personal Finance Bootcamp, the host discusses several common tax mistakes and introduces new tax laws for 2026. Starting with essential tax preparation steps, the episode explains the importance of gathering relevant tax documents, considering new changes like RSUs and employer stock, and the pitfalls of rushing to file taxes without all forms. The host emphasizes the need for meticulous reporting, particularly for tech professionals dealing with employer stock and those affected by income limits on IRA contributions. The episode also covers strategies such as backdoor Roth conversions, handling 1099 forms accurately, and the implications of recent changes to the state and local tax cap. Additional tips include maximizing dependent care credits, 529 plan contributions, and rental property depreciation. Finally, the host advises business owners on correctly claiming legitimate business expenses to avoid IRS scrutiny. Listeners are encouraged to seek professional advice and ensure all financial details are accurately reported.00:00 Introduction to Techie Personal Finance Bootcamp Season 801:23 Essential Tax Preparation Tips for 202601:53 Understanding New Tax Changes and Forms02:22 Avoiding Common Tax Filing Mistakes03:06 Time Travel Techniques for Tax Contributions04:47 Automatic Tax Adjustments and Deductions05:37 Maximizing Itemized Deductions07:01 Common Tax Filing Errors and How to Avoid Them09:05 Special Considerations for High Earners and Stock Options12:24 Tax Tips for Parents and Property Owners14:35 Final Thoughts and Looking Aheadhttps://www.levelupfinancialplanning.com/tax-planning-retirement-accounts-backdoor-roths/

Discover how Morgan DeBaun, CEO of Blavity and AfroTech, built her diverse income streams from the ground up. Whether you're starting with little or aiming to diversify your earnings, this episode offers actionable insights to grow your wealth. In this episode: Morgan shares her personal journey from investing at age 13 to building multiple income streams How to leverage your expertise for brand deals, speaking engagements, and consulting The importance of passive income through stocks, ETFs, and real estate Strategies for scaling and diversifying income based on your capital and time availability Practical tips for beginners to start their own income streams today Timestamps:  00:00 - Morgan introduces her nine streams of income and why they matter 01:00 - Starting early: Investing in stocks at age 13 and foundational money lessons 02:30 - Building wealth through W-2 salary, 401k, RSUs, and stock appreciation 04:00 - How Morgan secures brand deals with major tech companies and tips for becoming an expert 05:15 - Generating income via speaking engagements and training sessions 06:30 - Creating and selling educational workshops under the WorkSmart brand 07:45 - Monetizing content through Substack and book writing tips 08:30 - Rental properties as a long-term asset and passive income source 09:15 - Affiliate marketing and small-scale revenue streams 09:50 - Choosing income streams based on capital or time constraints 10:20 - Final thoughts: Building wealth with strategic diversification   Resources & Links: Morgan DeBaun's Book: Rewrite Your Rules  Blavity AfroTech AI mastery Training Passive Income Blueprint Twitter LinkedIn

Send a textWe unpack why California's tax system punishes high W‑2 earners with RSUs, then map out a stack of strategies that convert stock-based pain into lasting tax savings. We share how to use charitable deductions, credits, and timing to push your effective rate down.• RSUs as taxable income and cash flow squeeze• California marginal brackets and 13.3 percent top rate• Nonconformity on real estate professional status and bonus depreciation• Excess business loss limits against W‑2 wages• The SALT “sweet spot” between $600k and $500k income• Advanced charitable structures offsetting 30–60 percent of AGI• Solar and other tax credit strategies to reduce federal liability• Withholding adjustments to fund strategies mid‑year• Selling RSUs and pairing gains with losses for liquidity• Why ongoing planning with a strategist compounds savingsGo to prosperlcpa.com/opportunityreport  for a free customized video from me showing how much you can save 

If you work at SpaceX, you're likely holding one of the most valuable (and complicated) assets in the world. With a potential IPO on the horizon, the decisions you make with your SpaceX stock, RSUs, and equity compensation could determine whether that wealth creates freedom or long-term stress.Instead of starting with “What should I do with my stock?”, James explains why the first question has to be “What do I want my life to look like?” Without that clarity, selling, holding, or diversifying SpaceX stock becomes guesswork... even if the company continues to perform well. Using a detailed case study that closely mirrors the financial reality of many SpaceX employees, James shows how it's possible to be worth millions on paper and still feel financially constrained. When the majority of wealth is tied up in illiquid company stock, day-to-day flexibility, retirement timing, and peace of mind can all feel out of reach, even with enormous upside ahead. The focus isn't on predicting SpaceX's future valuation. It's on using equity intentionally. James walks through how taking enough chips off the table (not all of them) can lock in early retirement, reduce risk, and create optionality, while still allowing participation in future upside. He covers diversification, tax planning, liquidity decisions, charitable strategies, and why “retiring early” is less about stopping work and more about becoming financially independent. For SpaceX employees approaching liquidity events, vesting milestones, or long-term career decisions, this is a framework for turning concentrated stock into a life with more control — instead of deferring freedom while waiting for a perfect outcome.If you work at SpaceX and want your stock to support the life you actually want to live, this perspective changes how every decision gets made.-Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsementsParticipation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.Create Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Executives often focus on salary when evaluating offers. But real wealth (and potentially real risk) usually lives in the equity package. In this episode, Brian Dress and Noland Langford unpack how to evaluate job offers through a strategic lens, helping leaders avoid costly missteps and uncover long-term value. Key Topics: • Why equity comp is often misunderstood, even by seasoned execs • How to compare offers with RSUs, options, and performance shares • The biggest blind spots when changing jobs • Timing and tax insights few people catch

"Dissecting Compensation - A Primer on Understanding, Negotiating and Managing Pay"A CMO Confidential Interview with Richard Sanderson, the Marketing, Sales, and Communications Practice Leader at Spencer Stuart. Richard starts with the basics of salary, bonus and equity and branches out to compensation mix, the various types of equity, negotiating best practices, and the "other" elements of an offer. Key topics include: why the devil is in the details; when and how to discuss compensation; the difference between dumb luck and bad luck; and why everyone should do a "multi-year cash flow analysis." Tune in to hear why you should always read the proxy statement and the importance of being prepared to explain how you are using AI.*Dissecting CMO Compensation with Richard Sanderson (Spencer Stuart) — Salary, Bonus, Equity & Negotiation Playbook*What's “market” for a modern CMO, and how do you actually negotiate it? Richard Sanderson, who leads Spencer Stuart's Marketing, Communications & Sales Practice, breaks down the three pillars of pay (salary, bonus, equity), compensation mix by ownership model, and the real rules of negotiating offers, severance, and forfeitures. We also tackle vesting, RSUs vs. options vs. PSUs, what to ask recruiters (legally) about pay ranges, how to manage your team when equity is underwater, and why every CMO needs crisp AI impact stories in interviews. Actionable, candid, and built for executives who make or take offers. *Chapters*00:00 Intro — Welcome to CMO Confidential & Richard's background01:50 Why comp is hard to decode (and why it matters)02:12 The building blocks: salary, bonus, equity03:21 The data gap: only ~4% of F1000 list marketing leaders as NEOs04:26 Salary basics, bands, and industry norms05:35 Bonus mechanics & the one question to ask (3-year payout history)06:38 Equity 101 — long-term incentives and where value really accrues07:25 Compensation mix: public, PE, private, nonprofit08:25 Geography effect — US vs. Europe on equity weighting09:23 RSUs explained (and why they always have some value)10:19 Options & strike prices — upside vs. “underwater” risk10:57 PSUs — performance gates, accelerators, and board metrics12:17 Vesting types: time, performance, and event-based triggers13:15 Forfeitures if you leave early (and what's negotiable)15:09 Negotiating framework — timing, laws, posture16:34 When to talk comp without signaling “it's just the money”17:58 Pay transparency laws — expectations vs. history; what recruiters can ask20:23 Forfeitures checklist: bonus timing, unvested equity, make-wholes21:36 Know your company's rules (eligibility dates, presence requirements)22:36 Smart pushback: asking for the range and reducing info asymmetry23:47 Your moment of max leverage: the verbal offer27:58 Beyond pay: severance, sign-on, relocation, start date, perks29:00 CMO tenure math and why severance matters32:31 “Am I underpaid?” How to build a real case34:34 Managing your team through pay angst & proxy transparency36:29 Underwater equity — empathy, vision, and refresh cycles38:22 Timing luck: annual grants & market swings (“Liberation Day” example)40:00 Do the 5-year cash-flow comparison (and bridge Year 1–2)42:04 The new relocation math (mortgages & cost deltas)43:06 Titles, reporting lines, non-competes, and day-one docs43:50 Should you ever turn down a written offer?45:23 The reputational risk of reneging47:05 Be ready: the AI question in every CMO interview48:32 Wrap*Tags*CMO Confidential, Richard Sanderson, Spencer Stuart, CMO compensation, executive pay, salary bands, bonus plans, equity RSUs, stock options, PSUs, vesting, severance, negotiation, forfeitures, compensation mix, private equity, public companies, proxy statements, pay transparency laws, marketing leadership, executive recruiting, board compensation, make-whole bonus, cash flow analysis, AI in marketingSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Send us a textI'm joined by Ryan Goldenhar and Jackie Lewis, the powerhouse duo behind Wealth with Options, a San Diego–based firm helping tech professionals make sense of equity compensation, major liquidity events, and the emotional decisions that come with sudden or complex wealth.Ryan and Jackie bring a rare combination of technical rigor and humanity to financial planning—meeting clients not just where the numbers are, but where their values, fears, ambitions, and life transitions live.Together, we unpack what equity compensation really means, why money decisions are never “just spreadsheets,” and how true wealth is ultimately about freedom, clarity, and choice.This conversation is especially relevant for tech executives navigating RSUs, ISOs, IPOs, job transitions, or the question many silently ask: “What is all this money actually for?”Important Disclosures:Jackie Lewis and Ryan Goldenhar offer investment advisory services through Mariner Platform Solutions, LLC (“MPS”), an SEC-registered investment adviser. Wealth With Options and MPS are separate, unaffiliated entities. For additional information about MPS, including fees and services, please refer to Form ADV Part 2A, which is available on the Investment Adviser Public Disclosure website (www.adviserinfo.sec.gov). Registration of an investment adviser does not imply a certain level of skill or training.This podcast episode includes statements by Tina Powell of Intention.ly. Intention.ly is a marketing firm that is compensated by Wealth With Options to provide marketing and related services. This compensation creates a conflict of interest, as Intention.ly has a financial incentive to promote Wealth With Options and its services. Statements made by Intention.ly should not be construed as independent or unbiased. This endorsement is not a guarantee of future results or client experience.Discussion of careers in technology companies and equity-based compensation, including stock options, is provided for general informational purposes only. Stock options and other forms of equity compensation do not guarantee wealth creation. Outcomes vary significantly based on company performance, market conditions, vesting terms, concentration risk, tax considerations, and individual circumstances.Any examples or scenarios discussed are illustrative only and should not be interpreted as indicative of typical or expected results. Nothing discussed should be construed as individualized investment, tax, legal, or employment advice, or as a recommendation to pursue any particular employment or compensation structure. Any opinions expressed herein are subject to change without notice.There is no assurance that any investment, plan, or strategy will be successful. Investing involves risk

In this episode of Beer and Money, Ryan Burklo and Alex Collins discuss the challenges and strategies associated with over-concentrated stock positions, particularly in the context of tech companies and other large firms. They explore the risks of having a significant portion of one's wealth tied to a single stock, the emotional connections that can complicate decision-making, and the importance of coordinated financial planning. The conversation covers various strategies for unwinding concentrated positions, including selling shares, tax implications, and alternative methods such as options and exchange funds. The hosts emphasize the need for a systematic approach to managing concentrated wealth and the importance of seeking professional guidance. Check out our website:  beerandmoney.net Find us on YouTube: https://www.youtube.com/@beerandmoney Subscribe to our newsletter: https://www.quantifiedfinancial.com/subscribe-now Check out our Instagram: https://www.instagram.com/ryanburklofinance?igsh=ZTJzN3Jnajd5M2Mw Ryan Burklo's LinkedIn profile: https://www.linkedin.com/in/ryanburklo/ Alex Collin's LinkedIn profile: https://www.linkedin.com/in/alexandercollins/ For a quick assessment of your current financial life go to: https://www.livingbalancesheet.com/lbsVision/lite/RyanBurklo #over-concentratedstock #financialplanning #riskmanagement #investmentstrategies #taximplications #stockoptions #wealthmanagement #diversification #financialadvisor #concentratedwealth   Takeaways Many clients have concentrated stock positions due to RSUs or stock options. Concentrated risk can become significant over time, especially in tech. Emotional ties to a company can complicate financial decisions. It's crucial to consider future changes in company leadership. Planning to unwind concentrated risk can take months or years. Tax implications can complicate the selling of concentrated stock. Diversification is key to managing concentrated positions. Coordinating with financial and tax professionals is essential. There are strategies to manage concentrated stock without selling. Proactive planning can prevent financial stress in retirement. Chapters 00:00 Introduction to Over-Concentrated Stock Positions 02:51 Understanding the Risks of Concentrated Wealth 05:53 Planning Considerations for Unwinding Concentrated Risk 08:55 Strategies for Managing Concentrated Stock Positions 12:06 Alternative Approaches to Selling Stock 15:06 Conclusion and Call to Action

In this episode of Beer and Money, Ryan Burklo discusses the common misconception of financial progress, particularly among high earners who may feel stressed despite increasing net worth. He emphasizes the importance of building confidence in financial planning, understanding cash flow, and having clarity about one's financial situation. The conversation highlights the need for proactive financial management and the value of working with a financial advisor to navigate uncertainties and optimize financial outcomes.   Check out our website:  beerandmoney.net Find us on YouTube: https://www.youtube.com/@beerandmoney Subscribe to our newsletter: https://www.quantifiedfinancial.com/subscribe-now Check out our Instagram: https://www.instagram.com/ryanburklofinance?igsh=ZTJzN3Jnajd5M2Mw Ryan Burklo's LinkedIn profile: https://www.linkedin.com/in/ryanburklo/ Alex Collin's LinkedIn profile: https://www.linkedin.com/in/alexandercollins/ For a quick assessment of your current financial life go to: https://www.livingbalancesheet.com/lbsVision/lite/RyanBurklo   #financialplanning #confidence #cashflow #lifestyle #financialadvisor #wealthbuilding #RSUs #marketswings #financialscorecard #financialprogress   Takeaways The illusion of financial progress can lead to stress. High income does not always equate to financial confidence. Spreadsheets show outcomes but not the full financial picture. Many people face a certainty problem rather than a money problem. Understanding cash flow is essential for financial planning. Optimizing finances requires clarity about lifestyle goals. Conversations about money with partners are crucial. Financial plans should adapt to changing circumstances. Knowing your financial situation can provide peace of mind. Proactive financial management helps in achieving desired outcomes. Chapters 00:00 The Illusion of Financial Progress 02:48 Building Confidence in Financial Planning 06:04 Understanding Cash Flow and Lifestyle 08:50 The Importance of Financial Clarity

As the year comes to a close, young investors have a unique opportunity to make small moves that can compound into meaningful long-term results. In this episode, we walk through a practical, end-of-year checklist designed for early-career investors who want to stay organized, tax-aware, and financially disciplined. Lance Roberts & Jonathan Penn cover how to confirm you're capturing all available employer benefits, including 401(k) or 403(b) matches and vesting schedules. We also discuss how to think about Roth IRAs, HSAs, and other tax-advantaged accounts early in your career—when time is often your greatest asset. On the investment side, we review simple allocation checks, diversification risks, and why staying invested through volatility matters. We also highlight tax-smart considerations like capital gains awareness, loss harvesting, and stock-compensation planning for ESPPs and RSUs. Finally, we address the foundational elements of financial stability: emergency savings, cash management, credit health, and high-interest debt. This checklist is not about speculation—it's about building durable financial habits that support long-term wealth creation. 0:00 - INTRO 0:19 - Wealth by Brackets 3:39 - Will the Santa Rally be Delayed? 9:02 - Open Enrollment & Benefits Tips 16:12 - 401k/IRA Contributions & Employer Matches 24:26 - Investment Choices in 401k's 26:56 - Tracking Down old 401k's 29:38 - Understanding Vesting Schedules 32:29 - Catching Up in 401k 33:58 - Wills, Estate Plans, & Beneficiary Designations 36:26 - Checking for Leakage 39:55 - Annual Credit Report Review 41:18 - Comniog Attractions Hosted by RIA Advisors Chief Investment Strategist, Lance Roberts, CIO, w Senior Investment Advisor, Jonathan Penn, CFP Produced by Brent Clanton, Executive Producer ------- Watch Today's Full Video on our YouTube Channel: https://www.youtube.com/watch?v=3Wyudzh3naw&list=PLVT8LcWPeAugpcGzM8hHyEP11lE87RYPe&index=1 ------- The latest installment of our new feature, Before the Bell, "Data, Volatility & Santa Rally Risk," is here: https://youtu.be/gnorFZc1qM8 ------- REGISTER for our 2026 Economic Summit, "The Future of Digital Assets, Artificial Intelligence, and Investing:" https://www.eventbrite.com/e/2026-ria-economic-summit-tickets-1765951641899?aff=oddtdtcreator ------- Watch our previous show, "Facing Your Financial Ghosts," here: https://www.youtube.com/watch?v=Ypp_HKgciow&list=PLwNgo56zE4RAbkqxgdj-8GOvjZTp9_Zlz&index=1 -------- Get more info & commentary: https://realinvestm entadvice.com/newsletter/ -------- SUBSCRIBE to The Real Investment Show here: http://www.youtube.com/c/TheRealInvestmentShow -------- Visit our Site: https://www.realinvestmentadvice.com Contact Us: 1-855-RIA-PLAN -------- Subscribe to SimpleVisor: https://www.simplevisor.com/register-new -------- Connect with us on social: https://twitter.com/RealInvAdvice https://twitter.com/LanceRoberts https://www.facebook.com/RealInvestmentAdvice/ https://www.linkedin.com/in/realinvestmentadvice/ #MarketOutlook #SantaClausRally #Volatility #RiskManagement #StockMarketAnalysis #YoungInvestors #PersonalFinance #YearEndPlanning #InvestingBasics #FinancialWellness

Live from The Hyderabad Public School, a private high school in India which features notable alums 1) Microsoft CEO Satya Nadella, 2) Adobe CEO Shantanu Narayen 3) former Mastercard CEO Ajay Banga, 4) Fairfax Financial CEO Prem Watsa, and 5) Procter & Gamble CEO-designate Shailesh Jejurikar, it's an all-new Terrific Tuesday edition of Business Pants, featuring Analyst-Hole Matt Moscardi! On today's Lead Independent Turkey called November 25th, 2025: the Who Do You Blame? Game!Our show today is being sponsored by Free Float Analytics, the only platform measuring board power, connections, and performance for FREE.DAMIONCampbell's Places VP on Leave Following Viral 'Poor People' RantMartin Bally, Campbell Soup Company's vice president and chief information security officer: “"We have s--- for f---ing poor people. Who buys our s---? I don't buy Campbell's products barely anymore. Bioengineered meat — I don't wanna eat a piece of chicken that came from a 3-D printer."He also allegedly made derogatory comments about Indian coworkers and – according to the recording – claimed he sometimes came to work under the influence of marijuana: "F---ing Indians don't know a f---ing thing," the voice on the recording says. "They couldn't think for their f---ing selves."The statement follows claims made by former Campbell's security analyst Robert Garza, who filed a lawsuit in Wayne County Circuit Court alleging that Bally launched into an hour-long tirade during what was meant to be a discussion about Garza's salary.Campbell's: “We are proud of the food we make, the people who make it and the high-quality ingredients we use ... The comments on the recording are not only inaccurate—they are patently absurd.Campbell's also noted that Bally is not involved in food development. “Keep in mind, the alleged comments are made by an IT person, who has nothing to do with how we make our food,” the statement concluded.WHO DO YOU BLAME?The founding families:Voting power: (35%) Mary Alice D. Malone - 18% Bennett Dorrance- 15% Archbold D. van Beuren - 2%Board influence (76%): Mary Alice Dorrance Malone (61%; board member since 1990); Archbold Dorrance van Beuren (9%; wealth management); Bennett Dorrance (6%: bachelor's degree in art history from Princeton University and a master's degree in sustainable leadership from Arizona State University); Mary Alice Dorrance Malone Jr (accomplished equestrian, and a luxury fashion entrepreneur) MMInvestors: 11/18/2025 AGMAverage director support 98% (9 over 99%): 43% yes simple majority vote; regenerative agriculture program including pesticide reduction outcomes 11% yes; say on pay 99% yesAn unserious food board of 9 non-family board members:No food: Fabiola R. Arredondo (family investment trust); Howard M. Averill(former Time Warner CFO); Maria Teresa (Tessa) Hilado (former CFO Allergan); Grant Hill (NBA); Sarah Hofstetter (e-commerce sales); Marc B. Lautenbach (global shipping); Chair Keith R. McLoughlin (appliances); Kurt T. Schmidt (weed and pet food); CEO Mick J. Beekhuizen: 13 years with Goldman Sachs in roles including Managing Director in the merchant banking divisionAmerican pop-artist Andy Warhol for somehow making Campbell's Food company eternally relevant Q3 2025 Gender Diversity IndexLittle Movement on Boardroom Gender Diversity: 30% of Russell 3000 board members are women, a figure that has stayed within a narrow 30% to 30.3% range over the past five quarters.Percentage of Boards with 50% Women: Across the Russell 3000, 6% (175) of boards are composed of at least 50% women, while the remaining 94% (2,736) have less than 50% female representation.New Female Director Appointments Hit Record Low: 22.3% of new directors on Russell 3000 boards are women. This represents the lowest percentage recorded in the study (since Q12017)WHO DO YOU BLAME?The anti-DEI MAGA movementNominating Committees, specifically their Chairs MMPassive Investors (BlackRock, Vanguard, etc)The proxy experts: ISS, Glass Lewis, etc.Previous female board members who retired or died: if they were immortal maybe the numbers would be better?OpenAI announces shopping research tool in latest e-commerce pushOpenAI announced a new tool called “shopping research” that will generate detailed, in-depth shopping guides.The guides include top products, key differences between the products and up-to-date information from reliable retailers, OpenAI said.“With these new abilities, we can have shared prosperity to a degree that seems unimaginable today; in the future, everyone's lives can be better than anyone's life is now.”WHO DO YOU BLAME?The sycophants: open letter sent to the board of directors“We are unable to work for or with people that lack competence, judgement and care for our mission and employees,” the letter continues before demanding that “all current board members resign,” appoint “two new lead independent directors.”signed by a whopping 700 of the company's 770 employees — including CTO Mira Murati, who the board briefly named interim CEO only to be replaced just a few days later, and Altman's fellow cofounder Ilya Sutskever, who initially appeared to be one of the forces behind his ousterNew Initial Board (Nov 2023)Bret “Salesforce” Taylor (Chair), Larry “Epstein” Summers, and Adam “voted to fire him in the first place” D'AngeloNew Board Members (Mar 2024)Sue Desmond-Hellmann (former CEO, Bill “Epstein” & Melinda Gates Foundation); Nicole “Iran Contra” Seligman (former Sony GC); Fidji Simo (CEO of Instacart) MMThe wafflers: Ilya Sutskever and Adam D'AngeloNOT Helen Toner: Director of Strategy at the Georgetown Center for Security and Emerging Technology and Tasha McCauleySam:San Francisco, CA (Russian Hill): A historic mansion purchased for $27 million in 2020.San Francisco, CA (Adjacent Homes): Three adjacent houses purchased for $12.8 million each (totaling $38.4 million) in January 2024. These purchases appear to be consolidating a potential mega-compound next to his original Russian Hill home.Kailua-Kona, Hawaii (Big Island): A large, 22-acre oceanfront estate, quietly purchased in 2021 for $43 million (later listed for $49 million in 2025). It features multiple houses, a private marina/beach, helipadNapa, CA (Ranch): A 950-acre ranch, reportedly purchased for $15.7 million in 2020.Kohl's names Michael Bender as permanent CEO after a turbulent year and sales declines. WHO DO YOU BLAMEAshley Buchanan: On May 1, 2025, Kohl's board terminated Buchanan “for cause” following an outside investigation overseen by its Audit Committee. The investigation found that Buchanan directed Kohl's to do business with a vendor founded by someone with whom he had a personal relationship. He also caused Kohl's to enter into a multimillion-dollar consulting agreement involving that same person. Crucially, he did not disclose this personal relationship, which was a violation of Kohl's code of ethics.Golden hello: $17m equity and $3.75m cashFormer director Christine Day: Shortly after Buchanan was fired, Day resigned, citing “lack of transparency” and governance concerns. Day said she was frustrated that not all board members were kept informed of risks and that decisions seemed centralized (“Michael ‘handles' everything … then ‘tells' everyone what the decision is”). Kohl's strongly disputed her characterization, saying her resignation was not “due to any disagreements” over operations or practices.Investors: chair Bender named interim CEO 4/30/25… AGM 5/14/2595% yes bender; 55% yes pay; 89% yes Prising; 92% average; new chair 91% John E. Schlifske (2011-, longest-tenured)Compensation Committee: “regularly and actively reviewing and evaluating our executive management succession plans and making recommendations to the Board with respect to succession planning issues”Chair Jonas Prising (2015-)Member Michael BenderMichael Bender, who was the Board Chair and sat on COmp Committee and director since 2019, was named interim CEO$1.475M/175% target up to 350%/$9.5M equity ($500k more than ashley) target/$200k aircraft (up from $180k for ashley)/$160k relocationone-time award of restricted stock units (“RSUs”) valued at $3,775,000The glass cliff: women and POC promoted to precarious leadership positions, such as the CEO or a board seat, during times of crisis, organizational turmoil, or poor performance MMMATTWatchdog group warns AI teddy bear discusses sexually explicit content, dangerous activities. This is the $99 Kumma bear made by FoloToy using OpenAI's service. OpenAI said it was suspending Folotoy for violations of usage of ChatGPT. WHO DO YOU BLAME?:Folotoy, who's founder and CEO Larry Wang calls himself “Chief Geek Officer” and has a background in child psychology and behavioral science… oh, wait, not, he has background in computer science and was founder of a tech telecomm company and was a software developer for insurance before that. But he's obviously qualified to do this: “Kumma, our adorable bear, combines advanced artificial intelligence with friendly, interactive features, making it the perfect friend for both kids and adults. From lively conversations to educational storytelling, FoloToy adapts to your personality and needs, bringing warmth, fun, and a little extra curiosity to your day.”OpenAI - obviously Sam Altman's commitment to “the benefit of humanity” stopped short of “sex advice from baby toys,” even though he says having kids of his own will help him not destroy humanity. I assume he's not getting Sammy Jr a Kumma bear? DROpenAI's board - obviously if they had fired Sam Altman, there wouldn't be sex bears using ChatGPT. But Helen Toner was forced out by the rest of the board, investors, and public pressure - she's since said, “But for years, Sam had made it really difficult for the board to actually do that job by withholding information, misrepresenting things that were happening at the company, in some cases outright lying to the board,” and that Altman gave them, “inaccurate information about the small number of formal safety processes that the company did have in place.” Perhaps Altman said, “no, that teddy bear didn't just say he loved oral sex, that's just a misinterpretation.”Microsoft - Satya, despite misgivings from Bill Gates, threw $10bn at OpenAI in January 2023. In November 2023, the board removed Sam Altman. Turns out Microsoft had released a version of ChatGPT in India that Altman sanctioned outside of safety protocols - the board should have signed off, but Altman lied to them and hid it. But rather than Microsoft pulling back the release and recognizing the damage it could do, they swooped in and “hired” Sam Altman 3 days after his firing. Their $10bn investment might have been the first cog in a sex bear wheel.I'm the Chief People Officer at Walmart. I always wake up to the same U2 song and watch the 'Today' show. That is Donna Morris listening to U2's “Beautiful Day”, the first thing she does is go online, she doesn't drink coffee but drinks Diet Coke (“I've just never been a hot drink type of girl, I guess. I try to limit myself to two Diet Cokes a day, although every once in a while, I sneak in a third.”), she likes buying cookbooks but doesn't use them. Not mentioned: Walmart's DEI rollback, the new CEO coming in, working for a family dictatorship, and any of her colleagues - as chief people officer, there are almost zero people mentioned. WHO DO WE BLAME FOR THIS EXISTING?Professional Conservative Snowflake Robby Starbuck - he claimed Walmart as his first “victory” after Trump's election in the DEI rollback. Post-Starbuck snowflake-ism, Morris might have had a job managing humans, but now her job is basically to send pink slips and make sure there aren't TOO many swastikas in the bathroom stall. A few is fine, but c'mon. So to pass the time, Morris is stuck giving interviews to Business Insider.Business Insider, who must have known Morris had the potential to give an insipid review of her day when this was her excuse for Walmart's DEI rollback: "When you talk about diversity, equity, inclusion, all in part, there can be communities, and often the largest communities, that step back and say, 'Geez, I'm not sure if I'm even actually included'," Morris explained of the decision. Which echoes… ROBBY FUCKING STARBUCK, who said to anyone who would listen: "This is the biggest win yet for our movement to end wokeness in corporate America. This won't just have a massive effect for their employees who will have a neutral workplace without feeling that divisive issues are being injected but it will also extend to their many suppliers."Donna Morris, because as only we covered here when discussing the corporate move to blame the employees for every problem and getting fired, had this to say of her biggest red flag on an employee: “Nobody wants [to hire] a Debbie Downer. [Someone who is] constantly negative. You know they're going to show up [and] they're going to bring the problem, never the solution.” Literally, the JOB of HR is to field COMPLAINTS from employees about how their managers treat them - or is it too Debbie Downer to complain about racial discrimination of employees?Walmart's board - they must have signed off on Morris getting hired, right? Or a Walton? Someone somewhere thought this was a good idea? Take your pick:CFO of OpenAI Sarah Friar (who said OpenAI would need a government backstop, then clarified)Brian Niccol, the CEO of Starbucks who was given a golden hello, a golden parachute, and probably a golden shower, who just named to a “worst CEO” listThe current AND former CEO of WalmartSteuart Walton, who couldn't bother to even be named “Stuart” (he had to spell it with an extra “E”) with a claim to fame of marrying a Baywatch reboot actress, and Greg Penner, the son-in-law of a different Walton and snuck his way onto the board AND as co-owner of the Denver BroncosTom Horton, retired American Airlines CEO who was CFO of American for years right before they declared bankruptcy, but somehow is remembered for “restructuring” them instead of bankrupting them?Marissa Mayer - yes, that Mayer, formerly of YahooNot one, but TWO different consultantsRandall Stephenson, ex AT&T CEO, who, if I'm honest, seems to have actual integrity and I'm not sure why he's here, plus two DEI directors (because they're not white, so probably not qualified)

In this value-packed episode of Allworth's Money Matters, Scott and Pat unpack key financial strategies for high-net-worth investors navigating today's markets. From the overlooked need for regular portfolio rebalancing to smart planning for concentrated executive stock, they break down real-world scenarios with millions at stake. You'll hear a listener case involving $7M in assets, HSA withdrawal tactics, and 529 planning for seven grandkids—all through the lens of tax-smart wealth transfer. Plus, expert insights from Allworth's Head of Wealth Planning, Victoria Bogner, on avoiding massive tax traps with RSUs, ISOs, and stock options. Join Money Matters:  Get your most pressing financial questions answered by Allworth's co-founders Scott Hanson and Pat McClain live on-air! Call 833-99-WORTH. Or ask a question by clicking here.  You can also be on the air by emailing Scott and Pat at questions@moneymatters.com. Download and rate our podcast here.

#250: Chris dives into listener questions, covering open enrollment, investing, buying gold, life and auto insurance, RSUs, practical ways to leverage AI tools and more. Link to Full Show Notes: https://chrishutchins.com/open-enrollment-AMA-2025 Partner Deals Fabric: Affordable term life insurance for you and your family Superhuman: Free month of the fastest and best email with code ALLTHEHACKS Gusto: Free 3-month trial of the #1 payroll software DeleteMe: 20% off removing your personal info from the web Mercury: Help your business grow with simplified finances For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned PEOs: TriNet | Justworks Insurance Broker: Rich Sterling Productivity/AI Tools Notion NotebookLM Replit Cursor v0 Figma Perplexity Claude Mesa Homeowners Card (50k bonus with code CHRIS50) $1,200 U.S. Bank Bonus ATH Podcast Newsletter Ep #34: Insider Tricks to Healthcare, Prescriptions and Medical Bills with Marshall Allen Ep 104: Optimizing Your Insurance Policies Ep #140: Navigating Open Enrollment Ep #168: Building an Investment Portfolio to Grow and Protect Your Wealth Ep #248: How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss Submit questions for our next AMA here Leave a review: Apple Podcasts | Spotify Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com Full Show Notes (00:00) Introduction (00:30) Quick Episode Overview (01:22) How to Select Your Insurance Plan (05:19) Saving with a High Deductible Health Plan (14:19) Tips for Specific Drugs and Providers (15:27) Dental and Vision Plans (17:17) Benefits of FSAs (19:10) Getting Health Insurance Outside of an Employer (21:08) Getting Insurance for Your Business (23:20) Insurance via Medical Research Companies and Affinity Groups (24:52) Direct Primary Care (25:48) Reimbursing Medical Expenses Charged on a Credit Card (30:45) Diversification in an Incredibly High Stock Market (36:20) Investing in Precious Metals: Gold & Silver (40:55) Strategy for Handling RSU Compensation (43:35) Variable Universal Life Policy (48:05) The Rise in Auto Insurance Premiums Following an Accident (55:22) Buying A Used vs. New Car (58:06) Chris's Favorite Work Tools Including AI (01:02:07) Is AI an Actual Threat to Our Jobs? (01:04:26) Chris's Pre and Post W2 Job Experience (01:06:50) Find the Best Deals on the ATH Newsletter (01:10:53) The Next Gift Card Sale Connect with Chris Newsletter | Membership | X | Instagram | LinkedIn Editor's Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. Learn more about your ad choices. Visit megaphone.fm/adchoices

#651: Many who reach CoastFI find themselves in a strange in-between: financially independent enough to stop saving, but not ready to fully retire. When you're living off a taxable brokerage for decades, does the “never hold bonds in taxable” rule still apply? This episode explores how traditional asset location advice meets real-life spending. We unpack how to balance growth, taxes, and stability when your taxable account becomes your paycheck. Then we shift to two more listener dilemmas: helping a parent retire through shared home ownership, and using covered-call strategies to earn income from a stock-heavy portfolio. Listener Questions in This Episode Brandon (1:28): “I'm CoastFI and will withdraw from my taxable account for the next 20 years. Should I hold bonds in taxable, or keep it all in stocks?” Brandon's retirement accounts can grow untouched, but his taxable brokerage will fund two decades of living expenses. The classic rule says avoid bonds in taxable, yet Paula explains why that advice isn't universal. When your taxable account funds your life, it needs to act as a complete portfolio. We discuss how to balance risk, prioritize liquidity, and plan your glidepath into CoastFI life. Andrew (22:07): “My spouse and I co-own a home with my mother-in-law. How can we help her retire without creating family tension?” We explore fair, flexible ways to support an aging parent while keeping relationships healthy. Paula explains how to design a win-win deal and why seller financing can help balance cash flow and peace of mind. Chandan (49:16): “Can covered-call ETFs help me generate income from my stock portfolio and RSUs?” We explain how covered calls work, what “covered” really means, and the tradeoff between steady income and limited upside. For those with concentrated stock positions, Paula shares when covered calls make sense—and when simpler plans win. Key Takeaways The “no bonds in taxable” rule isn't universal. When you're drawing solely from taxable accounts for many years, that account needs to function as its own mini-portfolio, including bonds or cash for stability. Asset location follows purpose, not dogma. Tax efficiency matters, but liquidity and risk management take priority when the account funds your life. Think in terms of buckets. Your retirement accounts can stay growth-oriented while your taxable account carries the ballast for spending. Plan ahead for rebalancing. When taxable balances decline, know how and when to refill your bond/cash sleeve from other sources to keep your glidepath intact. The transition to CoastFI is a mental shift. You're no longer optimizing for maximum returns, you're designing for peace of mind and steady withdrawals. Chapters Note: Timestamps are approximate and may differ across listening platforms due to dynamically inserted ads. (01:28) Brandon's CoastFI question: bonds in taxable when withdrawals start now (03:56) Why “no bonds in taxable” is a rule of thumb, not a law (12:42) How to treat taxable as a stand-alone portfolio (18:31) Balancing tax efficiency with cash-flow reality (25:26) Helping a parent retire through shared property ownership (01:05:40) Options: Buying or selling with Options (01:07:07) Covered calls explained simply, income with a ceiling Resources & Links Asset Location Cheat Sheet (free): affordanything.com/assetlocation Guide to Double-I FIRE (free): affordanything.com/fiire Learn more about your ad choices. Visit podcastchoices.com/adchoices