Podcasts about qsbs

Send a textWe unpack how marriage can meaningfully lower taxes for high-income earners and how to plan before and after the wedding. We share practical strategies on timing income, creating deductible losses, leveraging participation rules, and using healthcare and equity tools to keep more of what you make.• why joint filing usually reduces total tax• doubled standard deduction and home sale exclusion• capital gains thresholds and NIIT mitigation• pre‑wedding income shifting and gifting stock• delaying sales with loans and cash‑out refis• accelerating deductions in the final single year• state moves, residency timing, and common law options• building a joint asset and income map• combining hours to meet material participation• short‑term rental losses to offset W‑2 income• excess business loss limits for joint filers• hiring a spouse and using an HRA via sole prop• enabling HRA with rental management work• stacking QSBS exclusions with smart gifting• real estate professional status and cost segregation• estate planning updates for married wealthGo to prosperalcpa.com/opportunityreport for a personalized video on potential tax savings. Go to http:///www.prosperalcpa.com/apply to explore services and advanced tax planning.

From Olympic sprinter to trusted advisor helping entrepreneurs save millions in taxes, David Flores Wilson shares proven strategies for QSBS planning, equity compensation design, and preparing business owners for successful exits both financially and personally. In this episode of the DealQuest Podcast, host Corey Kupfer sits down with David Flores Wilson, CFA, CFP, Managing Partner at Sinceres, who advises entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. WHAT YOU'LL LEARN: In this episode, you'll discover how QSBS planning can potentially exclude $10 million to $70 million or more in capital gains from taxes when structured correctly, why LLC to C Corp conversion timing creates dramatic differences in tax outcomes, and how QSBS stacking through non-grantor trusts multiplies exclusions. David shares why equity compensation plans often fail to motivate the specific people they target and what questions to ask before choosing a vehicle. You'll also learn about the personal readiness component of exit planning that determines whether entrepreneurs thrive or struggle after selling their businesses. DAVID'S JOURNEY: David's path to financial planning started with entrepreneurial instincts in an unexpected place. Growing up in Guam, he ran a comic book arbitrage business as a kid, discovering price differences between local stores and mainland mail-order catalogs. His father was a CPA with a home office, and despite wanting nothing to do with accounting, David absorbed financial concepts through osmosis that would later prove invaluable. After college at UC Berkeley, David joined Lehman Brothers and worked through the financial crisis. During that time, colleagues started coming to him with financial planning questions, and he realized helping people with their money was his true passion. He sat on that realization for years before eventually transitioning to financial planning. When Covid hit in 2020, David and his partner Dan Ryan launched Sinceres, and the firm has been growing since. OLYMPICS LESSON: David represented Guam in track and field at the 1996 Atlanta Olympics, competing in the 200 and 400 meters. The experience taught him something crucial about career selection. Unlike running, where pushing harder brings diminishing returns and constant injury risk, financial planning offers the opportunity to improve incrementally every single day. That compounding knowledge approach now drives how he serves clients. KEY INSIGHTS: QSBS planning stands out as potentially the most powerful tax planning tool for qualifying entrepreneurs. C Corps meeting holding period and active business requirements can exclude $10 million in gains, or 10 times basis for older shares, with new legislation increasing that to $15 million. The planning becomes even more powerful with LLC conversions where market value at conversion becomes the QSBS basis. The biggest mistake with equity compensation involves choosing vehicles based on what owners like rather than what motivates specific employees. "Equity" can mean participation in profits, upside potential, a seat at the table, or financial disclosure. Different people value these differently, and the best planning starts with understanding objectives before selecting tools. Exit planning involves three components that David implements from the first meeting with business owners. Getting personally ready addresses what provides purpose after selling. Getting financially ready ensures the numbers work. Getting business ready covers everything from customer concentration to management team development. The recent One Big Beautiful Bill Act has changed QSBS holding periods, SALT deductions, and AMT rules. Business owners should review their planning with advisors rather than assuming previous strategies still apply. Perfect for entrepreneurs considering entity structure decisions, business owners thinking about exit planning, and anyone interested in tax-efficient wealth building strategies. FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davidfloreswilson FOR MORE ON DAVID FLORES WILSON: https://www.planningtowealth.com https://www.linkedin.com/in/davidfloreswilson/ FOR MORE ON COREY KUPFER https://www.linkedin.com/in/coreykupfer/ https://www.coreykupfer.com/ Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast. Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today! Episode Highlights with Timestamps: [00:00] - Introduction: David Flores Wilson's credentials and areas of expertise [02:55] - Growing up in Guam with a comic book arbitrage business and CPA father [07:58] - Representing Guam at the 1996 Atlanta Olympics and career lessons from athletics [09:28] - QSBS fundamentals: Exclusions, holding periods, and qualifying business requirements [10:45] - LLC to C Corp conversions and the basis multiplication strategy [11:40] - QSBS stacking through non-grantor trusts and family gifting [19:40] - Equity compensation design: Why attraction, retention, and incentive vehicles often miss the mark[28:37] - Journey from Lehman Brothers through the financial crisis to launching Sinceres [31:59] - Exit planning framework: Personal, financial, and business readiness [41:27] - Recent tax law changes from the One Big Beautiful Bill Act [44:09] - What freedom means: Making impact through continuous improvement Guest Bio David Flores Wilson, CFA, CFP, is Managing Partner at Sinceres, advising entrepreneurs and business owners in New York City on personal financial planning from formation to exit and beyond. His areas of expertise include qualified small business stock planning, business exit planning, and equity compensation planning. David is a multiple Investopedia Top 100 Financial Advisor whose guidance has appeared in CNBC, Yahoo Finance, the New York Times, US News and World Report, and Investment News. He represented Guam in the 1996 Atlanta Olympic Games and sits on the Board of Directors as treasurer of the Lower East Side Girls Club. David is active in Entrepreneurs Organization, the Estate Planning Council of New York City, Advisors in Philanthropy, and the Exit Planning Institute. Host Bio Corey Kupfer is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker deeply passionate about deal-driven growth. He is the creator and host of the DealQuest Podcast. Show Description Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster. Related Episodes Episode 325 - Kelly Finnell: Using ESOPs in Ownership Succession Planning Episode 350 - Tom Dillon: Understanding Business Valuation and Exit Planning Realities Episode 328 - Richard Manders: Post-Exit Transitions and What Comes After Selling Your Business Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies Follow DealQuest Podcast: LinkedIn: https://www.linkedin.com/in/coreykupfer/ Website: https://www.coreykupfer.com/ Follow David Flores Wilson: Website: https://www.planningtowealth.com Keywords/Tags QSBS planning, qualified small business stock, business exit planning, equity compensation, entrepreneur tax strategy, LLC vs C Corp, financial planning for business owners, exit planning institute, tax-efficient wealth building, business succession planning, capital gains exclusion, non-grantor trusts, C corporation conversion, equity incentive plans, entrepreneur financial advisor

In this episode of Splitting Heirs, partners Beth Shapiro Kaufman, National Chair of Private Client Services and Trusts and Estates Chair, and Kristin V. Taylor join host Warren K. Racusin to discuss the One Big Beautiful Bill through a tax and estates lens. They talk about  "permanence" in the tax law while explaining the new estate and income tax benefits in OB3. Kaufman, Taylor, and Racusin elaborate on and debunk some of the bill's hot topics, including no tax on tips, no tax on social security benefits, SALT deductions, QSBS, and the 2/37ths rule. Speakers: Warren K. Racusin, Partner and Chair, Trusts & Estates Beth Shapiro Kaufman, Partner, National Chair, Private Client ServicesKristin V. Taylor, Partner, Tax, Private Client Services

This conversation delves into the intricacies of Qualified Small Business Stock (QSBS) and its significant tax benefits for founders. MICHAEL ARLEIN, Partner at Patterson Belknap, explains the eligibility criteria, the importance of strategic planning, and the potential pitfalls that can arise. The discussion also covers the implications of state taxes and the advantages of gifting strategies. We cover innovative approaches like the “GOAT” trust to maximize tax-free gains. Founders are encouraged to engage with legal experts early in their business journey to fully leverage QSBS opportunities. https://youtu.be/lfBt0j7BlW0?si=LufZ8j2YtgdspLMJ Takeaways from “QSBS For Founders” QSBS is a powerful tax benefit for founders.The maximum exclusion amount has increased to $15 million.Careful planning is essential to avoid QSBS pitfalls.Gifting QSBS stock can multiply tax exemptions.State tax implications vary; California does not recognize QSBS.Discounting shares can aid in estate planning.Converting from an S-Corp to a C-Corp can preserve QSBS benefits.Early engagement with legal counsel is crucial for founders.Innovative strategies like the GOAT trust can maximize benefits.Almost all businesses should consider QSBS eligibility. Chapters 00:00 Understanding QSBS: A Founder’s Guide.02:56 Navigating the QSBS Landscape: Common Pitfalls.06:07 Maximizing QSBS Benefits: Stacking Strategies.08:42 The Importance of Timing: Gifting and Valuation.12:03 State Tax Implications: The QSBS Challenge.14:52 Entity Structures and QSBS: What Founders Need to Know.17:37 Transitioning to C-Corp: Strategies for S-Corps and LLCs.20:29 Who Should Pay Attention to QSBS?23:44 Innovative Business Structures: Technology and QSBS-26:36 Early Stage Strategies: Cloning Yourself on the Cap Table- Transcript of “QSBS for Founders” Frazer Rice (00:01.109)Welcome aboard, Michael. Michael Arlein (00:03.096)Thank you. Good to be here. Frazer Rice (00:04.617)So let’s get started here. QSBS, Qualified Small Business Stock, is something that certainly all founders should be aware of. It’s a tax feature. It’s probably one of the nicest goodies that the federal government gives to people who are starting businesses. Take us through a little bit about what happens there. For founders, you’re going to hear the numbers 1202, which is the section that is quoted here. Take us through a little bit about what happens at QSBS and why it’s a powerful feature. Michael Arlein (00:37.496)Sure, that sounds good. To your point, the New York Times called QSBS a lavish tax dodge that is easily multiplied. And I happen to. I’m not aware of any other provision of the tax code that can save anyone as much money as QSBS. It’s really incredible. I think the policy reasons behind the provisions are that they’re designed to encourage entrepreneurship. Everyone on both sides of the political aisle is in favor of. The basic premise of it is that if you create a company.You own the stock for five years. The company’s in the form of a C corporation, It’s not in one of a series of restricted industries. Mainly service industries, that when you sell the stock, you can exclude from paying tax $10 million, the first $10 million of your gain. That’s the old rule, which I’m still dealing with, that that’s for stock that was issued before July 4th, 2025. And now QSBS has gotten even better. So if you get stock after that date. You hold it for actually now three years, you can exclude ultimately up to $15 million from tax. So we’re now dealing with two different regimes. I’m still stuck in the old regime. Most of the people I’m dealing with got their stock before last July. But I’ll try and point out the differences as we go along. Frazer Rice (02:29.066)Sure, as you said, there are a bunch of things you have to jump through. To make sure that you can sort of apply and then to further comply with the rules associated with it. Things like services. Making sure that maybe you don’t have too much cash and that it’s deployed correctly. Making sure that the original stock issuance persists throughout. What are some of the things that you tell your clients? How do you walk them through the process so that they don’t trip on themselves and lose this nice tax advantage? Michael Arlein (03:09.676)Yeah, there are some landmines, things that you can step on and blow it. There’s some weird rules around redemptions. Like if you have redemptions. Let’s say you create a company and then there’s three co-founders. Then very early on, one of the co-founders wants out or you want to kick them out. And then the mechanism for that is the company kind of buys back their stock. You know, there’s complicated rules that can, you know, blow up QSBS for the entire company. I think some people start their businesses as LLCs or S-Corps or things like that, and then later convert them. And that has to be done very, very carefully with good tax advice. Otherwise that can also blow things up. When I talk to founders, it’s pretty clear their business qualifies. They didn’t screw anything up. Frazer Rice (04:19.626)So the OBBBA in a sense turbocharged a little bit the tax savings. That five year requirement that you talked about. You can now get some of the benefits even as early as three years. And then the dollar amounts got expanded. In addition, and this was not necessarily OBBBA related. The ability to take one exemption and maybe multiply it via stacking continues to be a powerful tool. For those people who are walking into your office now. How do you get them when they sit down situated so that they do that planning upfront? Michael Arlein (05:08.598)Yeah, that’s, you we kind of buried the lead. The benefit of QSBS: it would be incredible if you could just pay no tax on 10 or $15 million. But what’s even more incredible is that you can stack or multiply the number of exemptions. You have using a provision of the code. It says that if you gift QSBS stock to some other person or entity. That that person or entity can take their own up to 10 or 15, their own QSBS exemption. I’m just gonna say it’s 15. We understand that’s for newly stocked. So, classic move for a founder would be to set up trusts for children. There’s a special kind of a trust for a spouse. You can do this with sometimes people make trust for their parents, their siblings. There are certain states where you can actually make a trust for yourself. Usually when people come to my office, the conversation is around creating entities. Typically trusts, and then gifting shares to those trusts. that As a family, you could go from 15 million tax free to 30 or 45 or 60 million tax free. The record I had one guy who had a very large family. He married, he had kids and was very close not only with his parents. With his siblings, his nieces, his nephews, even his aunts, uncles, and cousins. He created 23 trusts, which on paper at least would save up to $230 million. Wow. Yeah. Frazer Rice (07:08.896)There’s a danger with that though, with those 23 trusts had to be different. I imagine the IRS would say, wait a minute, we see what you’re doing. Stacking all of these different things is theoretically nice and all, but is there a way to create differences within those trusts so that the IRS doesn’t view them as one big pot? Michael Arlein (07:39.692)Yeah, great question. So you can’t create multiple identical trusts. Meaning I can’t create five trusts for my child. The IRS has rules that consider those trusts as one trust and would have only one exemptions. So, one of the limiting factors on creating trust is often, who are the people you’re willing to gift to? You know, so this guy with the 23, he actually was willing to create trust for his cousins, his aunts, uncles. Now, those individuals were the beneficiaries of the trusts, which means that they were eligible to receive money from the trust. But those trusts were designed so that when those people passed away, the money would circulate back to his children. So, you we never talked about it, but it’s possible that in his head, his plan was that he would maybe provide some benefit to his cousin. Maybe he’d say to his cousin, hey, if there’s $5 million in this trust and you need a little money, I’ll make some distributions to you, but I’m going to request that the trustee kind of withhold most of the money. And then when you die, it’ll come back and benefit my kids. So there are nuances there. But generally speaking, most people aren’t willing to do that. They’re not close enough with their cousins and their aunts and their uncles. So they end up maybe creating trusts, you know, for their kids, for their parents, sometimes, you know, for their spouse and maybe sometimes they go a little beyond that, but not that far. One thing that’s important is that the U.S. Frazer Rice (09:33.472)One thing that’s important is that the the QSBS is a capital gains tax Concept meaning you’re you’re saving on the tax. From a QSBS for Founders standpoint when the the founder sells the business, and you have to pay capital gains tax on that front. Part of the reason I’m skewing this toward founders is that there’s an gift in a state exemption of 15 million dollars. So it’s important to get these assets into these trusts as early as possible and with as low evaluation as possible. That in many ways is where the real leverage is. Does that square with your thinking? Michael Arlein (10:11.019)Yeah, absolutely. We have a permanent $15 million lifetime gifting limit. $30 million for spouses. And when you gift stock into these trusts, you’re typically gifting at a common stock valuation. People are familiar, founders are familiar with common stock valuations because they do that for purposes of issuing stock options, you know, the so-called 409A valuation. Now, a gift tax appraisal is different than a 409A valuation, but in many ways, they’re very similar. S0 founders know that, you know, they could be raising a preferred round at $10 a share, but their 409A common stock valuation is still $2 a share. So you can get a lot of gifting done. You can give a lot of shares away. You know, using your $15 million exemption, even if the company is very valuable. So we see founders doing this sort of gifting, you know, late in the game, even right before a transaction or an IPO. But if you had a crystal ball, or at least, you know, you were willing to take some risk, obviously, the earlier you do it, the better, because you could gift… I mean, theoretically, if you set up trusts and you gifted shares the day after you created your company, they would be worth essentially nothing. And so you wouldn’t have to use hardly any of your gifting exemption. The problem is most people, A, aren’t thinking about that on the day they create their company. They don’t have anyone whispering in their ear and telling them to do that. And number two, they wouldn’t want to spend the money on legal fees to set up structures because at that point they’re like, don’t know what this is going to be worth. This could be zero. This could go out of business in a year. So there’s a trade off that I see between doing this later in the process where you’re gaining visibility into outcomes, maybe for younger people sometimes, you know, there’s visibility into their family lives. Maybe when they founded the company they were single. Then if they wait five years they marry, they’ll have children, i.e. people who they could create trust for. But the cost of doing that is that you’re gifting at a higher value. Frazer Rice (12:46.591)One of the considerations that people don’t understand is the state tax implication. QSBS is a federal concept that a lot of states join onto and link to. But a state like California isn’t. And so sometimes that can be an untoward surprise to people that there’s a state tax that happens that they may not have expected. Michael Arlein (13:16.299)Yeah, it’s kind of bizarre that California, the home of Silicon Valley, doesn’t recognize QSBS. But most states do. My home state of New Jersey, in fact, very recently joined the QSBS club and now recognizes it at the state level. There are a few other states, I think. Pennsylvania, I don’t think recognizes it, but the vast majority of states do. But unfortunately, if you live in California, you’re probably only in quotes saving the federal tax. But the federal tax on $15 million, 23.8 % of 15 is a pretty big number. Frazer Rice (14:01.086)No question and absolutely worth doing. one of the things that I find happens is that from an income capital gains tax perspective, we’re on top of it with the QSBS. When we get into the estate planning world, we use the concept of discounting, meaning putting QSBS shares or any shares for that matter into other entities so that you get discounting for lack of marketability and the ability to make decisions around it. Are there any tripwires on that front as far as putting things into other LLCs so that you don’t, maybe in a sense that in trying to really maximize the estate planning and the estate tax avoidance that you create issues that might cause problems with your QSBS tax avoidance usefulness there. Michael Arlein (15:02.413)Yes. Again, the rules under Section 1202 of the code for QSBS have some strange traps for the unwary and some gray areas. And one of those gray areas is around transferring interests in partnership type entities, which would mean like an LLC or a partnership. that owns QSBS. So essentially, it’s very clear that if you have QSBS stock and you gift it into one of these entities we’ve been talking about, that that entity would take the QSBS attribute and be able to enjoy the benefits of QSBS. If the QSBS is held in an entity like an LLC, let’s say you set up a, well. Let’s say a realistic example is that you made an investment in a venture capital fund that invested in an early stage company that’s QSBS. And now you’re a limited partner in that fund and you know that that fund is going to have a large exit in this QSBS position and that you’re going to get the benefits of that, but it’s going to exceed $15 million. So you say, what I should do is I should take my interest in this venture capital fund. I should give them to trust for my kids so that when the fund distributes those shares or distributes the proceeds from selling that company, it’ll be split among various entities and I’ll be able to stack QSPS. The transfer of an interest in a fund that owns QSPS, there’s a gray area about whether the recipient of that fund interest would actually have QSPS and it’s generally viewed as something to be avoided. Frazer Rice (17:08.944)In a sense putting it at risk. A question that I think pops up is that there are people who started businesses maybe pre that July 4th date that you were talking about and maybe they chose an entity like an S Corp or an LLC that isn’t sort of a good qualifying C Corp and they’re looking and saying you know what I may be able to sell this business three to five years or beyond and take advantage of this QSBS. Are there avenues to be able to change that tax elections so that you can begin that QSBS and what’s the analysis around? Michael Arlein (17:44.972)Yeah, in fact, a fairly common structure is, and we haven’t really gotten into these details, but it’s a great question. So QSBS is actually the greater of $15 million or 10 times your basis. Now we ignore the basis rule for the most part because the vast majority of founders do not have basis. They create their company and they put nothing into it. With a bank account with $10,000 in it, and they’re not contributing actual dollars into their business. And so the 10 times basis rule doesn’t actually apply. But there’s a way for a founder to take advantage of that, and this strategy is actually called PACKING. And the packing strategy involves starting your business as an LLC and with an LLC and then converting it to a C corporation. with an LLC, when you convert, there’s an attribution of basis to the founder based on the value of the LLC’s assets. Theoretically, if you started off as an LLC, and before the LLC hit $75 million value of its assets, $75 million being sort of the cutoff for qualifying for small business, you have to acquire your stock before your company assets are worth $75 million. Theoretically, let’s say you did that when it was $74 million, then if your basis was $74 million, 10 times your basis would be $740 million, you would have up to $740 million tax free. So people kind of play this game. I think for a lot of companies, it’s not realistic to be an LLC because venture cap, if you’re going to raise venture funds, they want you to be a C Corp. This works for bootstrapped companies, but most companies are forming a C corporations. You know, there is a path to convert from an S-Corp to a C-Corp and preserve QSPS for Founders. I’m no expert in that. All I can tell you is that it has to be done very carefully and very specifically. And I’ve seen a lot of people who didn’t know they needed to do anything specific and they do not qualify for QSPS. Frazer Rice (20:45.085)As we sort of, I’m not going to say wind down here because we may have some other topics that pop up. But when someone walks through their door, I guess maybe the way to think about it is, who does this apply to? You said the services industry. So accounting, finance, that type of thing- NO. For those things that venture tries to invest in, whether it’s software or other processes, who is really should be paying attention to this? Michael Arlein (21:16.491)I mean, I think almost anyone should be paying attention to this because it may be that you don’t qualify, but often people do. And more often than not, you do. This has broad application for most businesses. There are excluded industries, architects and lawyers and accountants. But if you’re doing something in the tech world, you’re probably going to qualify. It’s good to get some advice from the corporate lawyer who’s helping you create your business. I think one of the considerations of whether you form as a C Corp or an LLC is probably the availability of QSBS status. You know, I think stacking strategies, it’s worth having a conversation probably sooner than later with a lawyer to find out what the menu of stacking options is. I talk to people all the time and we decide it’s premature for them to do something. And then they call me back a year or two later and all the time I’m calls from people who say, hey, we spoke a few years ago and now Frazer Rice (22:34.013)Alright. Michael Arlein (22:39.913)the time is right. So it’s good to get educated, learn what the options are. QSBS stacking is not just about giving shares to your kids. There are strategies that are specifically designed for single people where you can create these benefits for yourself and You know, it’s too good to be missed. if you, I do talk to people who say to me, they’re usually on their second venture or third venture and they say to me, I really screwed this up the first time around. I paid no attention to it and I was focused on my business and I just screwed it up. I literally cost myself millions or tens of millions of dollars had I done it correctly. And now that’s why I’m calling you, because I want to do it correctly the second time around. Frazer Rice (23:33.278)Part and parcel with that, I ran into somebody really more of what’s called a media personality. And usually the way I think of it is that the QSBS isn’t necessarily available for people whose value is centered around them as a personality or them as a brand. But I said, you know what, the QSBS component, while it might not apply here, if your business morphs into something where you’re developing other things, slash maybe you turn into a media production company or, youbecome involved in a technology that drives other things, that you shouldn’t dismiss that. The pivot in the business from sort of a personality generated to something a little bit more business process generated might be something to think about, not only from a strategy standpoint, not that you necessarily wanna do things purely for tax reasons, but if that’s a natural consequence, that’s something to think about. Has that ever popped up in your world? Michael Arlein (24:31.915)Yeah, for sure. Every business these days is technology enabled. And I think sometimes businesses that you wouldn’t think of as being technology businesses are doing enough technology things that they can claim that they’re a technology business and not a business providing a particular kind of service. So, you know, with the help of a clever accountant or a tax lawyer, this is not an area that I operate in. I’m more about multiplying QSBS once you have it. But there are tax lawyers and corporate lawyers and accountants who can advise you how to make your business eligible for QSBS by leaning into, as you said, things that you’re doing that may be…you know, eligible versus other parts of your business that would not be. Also, you know, you can, sometimes you see companies that are divided, right? Like, so there’s a company who provides counseling services, like, you know, they’re actually hire psychotherapists that will counsel you, you know, online, like on a Zoom. and their business is split. There’s a medical services company that employs all the counselors and medical services is one of the excluded industries. But then they also have a completely separate business that is their technology platform. And the way they structured it, the value is really in the technology platform. That business is QSBS eligible because it’s a completely separate company. Frazer Rice (26:28.771)That’s a great example. part of the purpose of the question was to elicit that, is that people may say, well, we fall squarely into one classification when maybe some underlying thought might lend itself to structuring from a tax perspective that might be useful later on. OK, now as we wind down, for someone who is, at this point, starting a company when they’re forming these things, not that you, QSBS for Founders should drive the world, but how do they get involved with the discussions so that they do the right things early? Michael Arlein (27:06.401)Yeah, I mean, I do have a very specific strategy that I love for people who are about to form a company. And it really works best in that scenario of an early stage company that’s just about to launch. The way I describe this to founders is that you can and should clone yourself on the cap table. So if you start off a company and you own all of the shares, you’re basically eligible for 15 million tax free. That’s great. But what if you could clone yourself and there were three Frazers on the cap table, then Frazer would have $45 million tax free. So how do you do this? You can do it with trusts. And the beautiful thing is if you have other people create trust for you, then you can be the beneficiary of the trust and control it as well. And I have sort of branded and named this strategy a GOAT trust, which of course has the double meaning, know, greatest of all time. Frazer Rice (28:21.02) QSBS for FoundersRight. Michael Arlein (28:21.165) QSBS for FoundersBut actually stands for gift optimized to alleviate taxes. The essentials of it are is that we would work with your parents, the founders parents, we would work with your grandma, your uncle, and we would spin up some trusts that they create for the benefit of you as the founder. You would have all sorts of control and access to those trusts and they make a gift into those trusts, probably something fairly modest. Then those trusts on the day of formation buy up some of the common stock. And so those are your clones. You know, you’re having your cake and eating it too. You’re getting, you know, QSBS stacking for Founders. You’re getting some other benefits we haven’t even talked about. Those trusts can be exempt from a state tax and state level income tax. And you control those trusts and benefit from them. So we’ve essentially cloned you on the cap table. And that is a beautiful strategy that most people miss out on because they don’t do it. And then they come to me a few years later and they own the stock and it’s valuable and then we have to do the more traditional stacking strategies. Frazer Rice (29:40.432)Really cool stuff. Michael, how do people get in touch with you if they have these problems slash opportunities? Michael Arlein (29:48.525)Sure, well they can Google me. I have a nice web presence. We have our…Founder Focus Practice Group that I lead at the firm, which is very specifically tailored to provide legal services to founders, personal legal services. And I focus on the tax side of that and QSBS stacking for Founders. My email, msarlein at pbwt.com. Phone number 212-336-2588. Frazer Rice (30:23.324) QSBS For FoundersThat will all be in the show notes. Michael, thanks for being on. Michael Arlein (30:26.753) QSBS For FoundersThank you. FAMILY OFFICE MYTHS https://www.amazon.com/Wealth-Actually-Intelligent-Decision-Making-1-ebook/dp/B07FPQJJQT/ QSBS for Founders QSBS for Founders

גיא קצוביץ' מארח את עמית קרפ (Bessemer Venture Partners), ברק שוסטר (Battery Ventures) וינאי אורון (Vertex Ventures) לדיון סוער על האירועים המרעישים בהייטק.הפרק עוסק ברכישת QAI על ידי אפל (Apple) בסכום של 1.5 מיליארד דולר וטכנולוגיית ה-Silent Speech, בניסוי החברתי המרתק והמסוכן של OpenClaw (לשעבר ClaudeBot) שיוצר רשת חברתית של סוכני AI, ובמגמת המעבר של סטארטאפים ישראלים לרישום כחברות דלאוור (Delaware) בארצות הברית.בנוסף, מנותחים ביצועי מניות ה-SaaS בבורסה, השפעת הבינה המלאכותית על עולם הגיימינג (Google Genie) והתמריצים הנדרשים ליזמים בישראל.(00:00) - פתיחה (02:37) -אפל רוכשת את QAI ב-1.5 מיליארד דולר(09:32) - הניסוי של OpenClaw: רשת חברתית לבוטים(32:32) - סוכני AI אישיים: פרודקטיביות או סכנה? (44:17) - משבר הרישום: ישראל נגד דלאוור (QSBS)(54:12) - גוגל ג'יני והתרסקות מניות הגיימינג וה-SaaSלאינסטגרם של גיא: https://bit.ly/48OziEHלפודקאסט באינסטגרם: https://bit.ly/4oND8Toלפודקאסט באפל: https://apple.co/3Lfv8Mbלפודקאסט בספוטיפיי: https://bit.ly/47Th96H

Non-grantor trusts are stepping into the spotlight, not for estate tax, but for income tax planning. In this episode, Cary Sinnett sits down with tax expert Bob Keebler to explore how the One Big Beautiful Act (H.R.1) reshapes the planning landscape. You'll hear how you can use trusts to reclaim lost SALT deductions, stack §199A benefits, shift income across generations, and even layer in QSBS exemptions. If your clients are hitting phaseouts or facing high state taxes, this episode delivers advanced strategies to optimize their tax position now and into the future. Non-Grantor Trusts: Keebler explains how trust structures can sidestep phaseouts and help clients reclaim deductions previously lost due to high AGI. The "Tax Trifecta Trust" Explained: Learn how to stack SALT deductions, layer multiple §199A deductions, and shift income strategically using non-grantor trust planning. Five Strategies You Can Use Today Income shifting to lower-bracket heirs Stacking SALT deductions across multiple trusts Boosting §199A deductions with trust-level taxpayers Expanding QSBS exemptions via strategic trust ownership Reducing or deferring state income tax through out-of-state trust situs Real-World Implementation Advice: Bob outlines guardrails around IRC §643(f) to avoid having multiple trusts collapsed into one. Hear how to structure trusts legally and practically for high-impact planning, and how to identify ideal client profiles for this approach. What CPA Financial Planners Need to Watch For: Bob discusses state-specific issues, kiddie tax complications, trust drafting must-haves, and how CPAs can lead the planning process with confidence. AICPA Resources: Video: Decoding Trusts and Wills: Provisions for PFP Practitioners Video: Year-End Planning Through the Lens of H.R. 1 Resource: Charitable planning post OBBBA rules This episode is brought to you by the AICPA's Personal Financial Planning Section, the premier provider of information, tools, advocacy, and guidance for professionals who specialize in providing tax, estate, retirement, risk management and investment planning advice. Also, by the CPA/PFS credential program, which allows CPAs to demonstrate competence and confidence in providing these services to their clients. Visit us online to join our community, gain access to valuable member-only benefits or learn about our PFP certificate program. Subscribe to the PFP Podcast channel at Libsyn to find all the latest episodes or search "AICPA Personal Financial Planning" on your favorite podcast app.  

In this episode of the Be Wealthy Podcast, Brett Tanner sits down with his longtime CPA, tax strategist, and trusted advisor Brian Muia for a deep dive into entrepreneurship, wealth-building, and advanced tax strategy.Brian shares his journey from growing up with limited resources to building and exiting multiple businesses, including companies in software, steel recycling, and accounting. He breaks down how early lessons around hard work, leverage, and replaceability shaped his entrepreneurial mindset — and why building a business that doesn't rely on you is the key to true freedom.The conversation goes deep into passive income, leverage, exits, subscription-based businesses, and the latest tax strategies from the “Big Beautiful Bill.” Brian explains how smart planning around depreciation, Section 179, QSBS, and opportunity zones can dramatically accelerate wealth creation for entrepreneurs and real estate investors.This episode blends real-world business lessons, mindset, and highly tactical tax insights every serious entrepreneur should understand.

In this episode of Tank Talks, host Matt Cohen and recurring guest John Ruffolo kick off the new year with a true “only in 2026” combo: a front-row seat to a SpaceX Falcon 9 launch carrying Kepler Communications' satellites, followed by a hard reality check on Canada's venture capital slowdown. John breaks down what it felt like watching the rocket, the first-stage landing, and why Kepler's mission is bigger than a cool space flex: it's the early shape of space-based data centers and laser-linked networks.From there, Matt and John unpack an RBCx report arguing 2025 was Canada's worst VC fundraising year since 2016, and why “capital is fungible” is a comforting myth at the seed stage. They dig into how de-globalization and national self-interest are reshaping capital flows, why Canada is getting squeezed by the barbell effect in venture, and what policy levers (like a QSBS-style incentive) could actually restart domestic risk capital. The episode closes with two tension points that rhyme: Nvidia's $20B Groq (with a Q) deal showing how returns can flow outside Canada, and the escalating political drama of Trump's DOJ targeting Fed Chair Jerome Powell and what that uncertainty does to markets.If Canada can help put “data centers in the sky,” can it also build the domestic capital base to keep its best companies anchored at home?“A Data Center in the Sky” + Laser-Linked Networks (00:03:07)Kepler's satellites are positioned as more than comms hardware: think orbital compute + storage + real-time processing, with laser links connecting satellites like a network in space.The RBCx VC Report: 2025 Fundraising Hits a Low (00:05:51)Matt summarizes the report's headline numbers and why the pain concentrates on emerging managers and the long tail, not the handful of breakout founders who can raise anywhere.“Venture Investing Is Local” in a De-Globalizing World (00:08:39)John challenges the idea that foreign capital will fill gaps at the earliest stages. In this cycle, countries increasingly keep capital for their own ecosystems, making Canada's domestic shortage more dangerous.The Barbell Effect: Giants and Niche Funds Win, the Middle Gets Crushed (00:10:17)They outline how venture is polarizing into mega-platform funds and specialized micro-funds, while mid-sized generalists get squeezed, and why that dynamic is amplified in Canada.Nvidia's $20B Groq Deal and Canada's Return Profile (00:12:36)They break down the Groq (Q) story, Canadian ties among investors and operators, and the bigger question: if LPs can make outsized returns elsewhere, what keeps capital committed to Canada?Trump vs Powell: DOJ Pressure, Fed Independence, and Market Fallout (00:17:38)They react to the reported DOJ move against Jerome Powell, how even Republicans are uneasy about weaponization, and why political pressure campaigns tend to increase uncertainty, not lower it.Why Uncertainty Pushes Rates Up, Not Down (00:19:30)John's punchline: the intended outcome (lower costs, lower rates) can backfire as markets price in instability, and the Powell timeline may extend into a longer institutional fight.Connect with John Ruffolo on LinkedIn: https://ca.linkedin.com/in/joruffoloConnect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1Visit the Ripple Ventures website: https://www.rippleventures.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com

Stop letting your tax return tell the only story about your money. We invited Rob Cook—CPA, CFP, and seasoned advisor to executives, athletes, and families—to break down how real tax strategy starts with who you are, where you want to go, and the few moves that actually change your outcome. Instead of chasing every trick on the internet, Rob shows why stacking “base hits” creates immediate savings and flexibility, and how to choose one or two “home runs” that fit your strengths.We talk through the crucial difference between a historian CPA who files forms and a strategic partner who looks through the windshield. You'll hear why high-earning W‑2 professionals are not stuck, how accredited status opens meaningful options, and how to avoid complexity that rich headlines can afford but most people can't defend. Rob shares a simple, repeatable process: clarify your goals and constraints, close tax leaks hiding in plain sight, align strategy with life and cash flow, then implement and iterate as your fastball evolves.From HSAs, donor-advised funds, and retirement plan design to QSBS, cost segregation, and real estate professional status, we separate the tools from the hype. You'll learn how to convert personal costs into valid business deductions when facts allow, why lifestyle creep kills deployable capital, and how a personal CFO framework helps you save taxes without sacrificing sanity. The goal is clarity and control: a lighter tax bill, a simpler structure, and more energy for the work and people you love.If you're ready to make money simple and build around your true wealth creation play, this conversation is your blueprint. Subscribe, share with a friend who needs a better plan, and leave a review telling us your top “base hit” to implement this week.-----With over 10 years of experience in accounting and wealth management, Rob has worked with everyone from CEOs and world-class athletes to local families, helping them reduce taxes, build wealth, and achieve financial freedom. Holding both a Master's and Bachelor's in Accounting from BYU, he is a Certified Public Accountant (CPA), Certified Financial Planner (CFP®), and has passed Level I of the Chartered Financial Analyst (CFA) exam.Known for bringing both expertise and personality to finance, Rob is passionate about personal finance, taxes, and investing. Frustrated with the industry's lack of real impact, he set out to truly help people transform their financial futures—and now, that's what he does every day.Connect with Rob Cook:Rob Cook, Bement & Company, Director of Strategic Tax380 North 200 West Ste 112 Bountiful, UT 84010801-936-1900rob@bementcompHear Past episodes of the Way2Wealth Podcast!https://theway2wealth.com Learn more about our Host, Scott Ford, Managing Director, Partner & Wealth Advisorhttps://www.carsonwealth.com/team-members/scott-ford/ Investment advisory services offered through CWM LLC, an SEC-registered investment advisor. Carson Partners, a division of CWM LLC, is a nationwide partnership of advisors. The opinions voiced in the Way to Wealth with Scott Ford are for general information only and are not intended to provide specific advice or recommendations for an individual. Past performance is no guarantee of future results. All indices are unmanaged and may not be invested into directly. Investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. To determine what may be appropriate for you, consult with your attorney, accountant, financial or tax advisor prior to investing. Guests on Way to Wealth are not affiliated with CWM, LLC. Legado Family is not affiliated with CWM LLC. Carson Wealth 19833 Leitersburg Pike, Suite 1, Hagerstown, Maryland, 21742.

Why do billions of dollars of stock trade hands based on napkin math and vibes? Billy Gallagher, CEO of Prospect and former Rippling employee, joins Patrick McKenzie (patio11) to walk through the information asymmetry that costs less-sophisticated employees massive amounts of money. From understanding when to early exercise options to navigating 83B elections and tender offers, they discuss the critical decisions that have a shot clock ticking the day you sign your offer letter.–Full transcript available here: www.complexsystemspodcast.com/understanding-equity-at-tech-companies/–Sponsor: Framer is a design and publishing platform that collapses the toolchain between wireframes and production-ready websites. Design, iterate, and publish in one workspace. Start free at framer.com/design with code COMPLEXSYSTEMS for a free month of Framer Pro.–Links:Prospect: www.joinprospect.com/–Timestamps:(00:00) Intro(00:44) Billy's professional journey(01:07) Equity management challenges(02:29) The importance of equity compensation(04:53) Equity grant structures in startups(06:09) Understanding vesting terms(07:09) The value of equity over time(08:48) The myth of options as lottery tickets(11:23) Career tailwinds from startup experience(14:25) Breaking into the tech industry(15:16) The role of equity in compensation(17:49) Employee equity plans and dilution(19:59) Sponsor: Framer(21:06) Stock options vs. RSUs(21:55) The decision to exercise options(27:11) Tax implications of exercising options(33:03) The role of HR in equity management(36:14) Bootleg spreadsheets and vibes-based investing(38:09) Navigating tax complexities in different scenarios(41:31) The importance of extended exercise windows(44:18) Challenges with tax residency and remote work(49:43) The role of accountants in managing equity(53:41) Understanding the 83(b) election and QSBS(01:01:03) Tender offers and secondary sales(01:08:38) Strategies for exercising and selling options(01:12:28) Navigating financial decisions in startups(01:16:59) Wrap

In this episode, Sasha Orloff talks with Nick Abouzeid, Co-founder and CEO of Rivet, about raising venture capital from XYZ, Haystack, and other angels to build a modern tax and accounting firm that serves 600+ category-defining companies like Cursor by combining world-class tax practitioners with custom-built software infrastructure, delivering premium responsive service while challenging the traditional accounting firm model of unresponsive service and outdated technology. -- SPONSORS: Notion Boost your startup with Notion—the ultimate connected workspace trusted by thousands worldwide! From engineering specs to onboarding and fundraising, Notion keeps your team organized and efficient. For a limited time, get 6 months of Notion AI FREE to supercharge your workflow. Claim your offer now at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://notion.com/startups/puzzle⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Puzzle

Are you building wealth — or just hoping it lasts?In this episode of Grow Your Business & Grow Your Wealth, host Gary Heldt speaks with Katherine M. Sheehan, Managing Director and Wealth Strategist at Crestwood Advisors, about how smart planning protects both your business and your legacy.Katherine breaks down what every entrepreneur should know about estate and succession planning — from powers of attorney to corporate recordkeeping — and explains how the Qualified Small Business Stock (QSBS) provision can help business owners exclude up to $10 million in gains when selling their company.You'll learn how to avoid costly mistakes, when to bring in specialized advisors, and how to prepare the next generation to carry your vision forward.

Are you building wealth — or just hoping it lasts?In this episode of Grow Your Business & Grow Your Wealth, host Gary Heldt speaks with Katherine M. Sheehan, Managing Director and Wealth Strategist at Crestwood Advisors, about how smart planning protects both your business and your legacy.Katherine breaks down what every entrepreneur should know about estate and succession planning — from powers of attorney to corporate recordkeeping — and explains how the Qualified Small Business Stock (QSBS) provision can help business owners exclude up to $10 million in gains when selling their company.You'll learn how to avoid costly mistakes, when to bring in specialized advisors, and how to prepare the next generation to carry your vision forward.

Terry Sylvester Charron, head of investment advisory and planning solutions, and Jere Doyle, senior wealth strategist, unpack changes to Qualified Small Business Stock as result of OBBBA. 

S4:E196 David gives The Venture Update with a special segment on the potential impact of Quantum Tokens on the blockchain. Then Paul provides a brief update on the current status of Capital Gains Tax Exclusion for gains on Qualified Small Business Stock or QSBS with Ben Glenn, an accountant specializing in startups. The One Big Beautiful Bill substantially updated the QSBS rules, solidifying one of the key incentives for startup investing for stock issued on or after July 5, 2025. (review recorded 10.1.25)Follow David on X at https://x.com/DGRollingSouth Follow Paul on X at https://x.com/PalmettoAngel Connect On LinkedIn with David at https://www.linkedin.com/in/davidgrisell/ Connect On LinkedIn with Paul at https://www.linkedin.com/in/paulclarkprivateequity/ We invite your feedback and suggestions at www.ventureinthesouth.com or email david@ventureinthesouth.com. Learn more about RollingSouth at rollingsouth.vc or email david@rollingsouth.vc.

Guest: Alex Duta  CEO/Founder at Albi (restoration management software)  https://albiware.com/ Thinking about selling to PE? Alex explains why many contractors should hold and tech-enable instead then shows how to do it: AI for ops, revenue per-employee targets, CRM→Ads feedback loops, valuation math (service vs. software), and the QSBS play to keep more at exit. Real tactics for restoration/roofing/plumbing/HVAC leaders who want margin, scale, and optionality.You'll learnWhat “tech-enabled” actually means for a contractor (and how to measure it)A prioritization toolkit (RICE) to pick high-leverage automations firstCRM→Google Ads conversion feedback to drop CPL & boost job sizeHow tech enablement changes valuation multiplesA primer on QSBS and why waiting can be worth millionsConnect with Alex: https://alexduta.com/ • @itsalexduta Hire Hook Agency for home-service growth: https://hookagency.com/

גיא קצוביץ' מארח את עמית קרפ (Bessemer Venture Partners), ברק שוסטר (Battery Ventures) וינאי אורון (Vertex Ventures Israel) לניתוח גל הפיטורים באמזון (Amazon) ולייטריקס (Lightricks) והשאלה האם AI הוא הסיבה האמיתית, או תירוץ להתייעלות. הדיון עובר לעתיד חברות ה-SaaS מול חברות "AI FIRST", בוחן את "כלכלת הבחירות" של שר האוצר בצלאל סמוטריץ', ומסביר מדוע יזמים ישראלים מעדיפים להתאגד בדלאוור (Delaware) בזכות הטבת המס QSBS. בנוסף, נתונים חדשים על יזמים סדרתיים (Wiz, CyberArk) בישראל, והמעבר של OpenAI למבנה רווחי בשווי 500 מיליארד דולר(00:00) - פתיחה(04:24) - פיטורי AI באמזון ולייטריקס: האם AI הורג משרות?(12:14) - למה חברות AI FIRST יהרגו את תעשיית ה-SaaS?(24:21) - "כלכלת בחירות" והטבת המס (QSBS) שמושכת יזמים לדלאוור(37:14) - יזמים סדרתיים בישראל (Wiz, CyberArk)(57:08) - המבנה החדש של OpenAI: שווי 500 מיליארד דולר והעסקה עם מיקרוסופט

Welcome back to The Entrepreneur's Journey. In this episode, Jason Gabrieli sits down with John Cavanaugh, CPA and tax attorney at Firenze Advisors, to discuss the foundational role that legal entity structure plays throughout the life of a business—from launch to scale to exit. They explore common pitfalls, how to adjust structures as businesses grow, and key planning considerations for exits, succession, and estate transitions. If you're a business owner thinking about growth or preparing for a future sale, this episode is packed with practical knowledge.Tune into this episode to also learn:● Why your legal entity structure isn't just paperwork—but the core of your business.● How and when to shift from LLC to S-Corp or C-Corp status.● The role of installment sales, trust planning, and QSBS in reducing tax liability.● What business owners often overlook when preparing for a sale or succession.What we discussed● [00:01:36] Why entity structure is foundational—and what most owners overlook.● [00:03:16] How and why business structures should evolve over time.● [00:05:06] The niche John fills: strategic planning across legal and tax.● [00:06:54] Real estate and multi-entity structures: liability and tax traps to avoid.● [00:09:01] Debt, partners, and why cross-collateralization needs careful planning.● [00:10:40] Transitioning a business: selling to outsiders vs. keeping it in the family.● [00:13:03] What surprises owners during due diligence and how to be prepared.● [00:16:45] Why planning ahead matters: using trusts and state residency smartly.● [00:18:11] Charitable trust and life insurance planning to reduce estate tax.● [00:20:31] Holding company structures: when and why to consider one.● [00:24:31] What clients usually miss: books, documentation, and cleanup.● [00:26:24] Installment sale example that saved significant taxes.● [00:30:07] Managing wealth post-sale and preserving it for future generations.● [00:32:06] The power of looking at your structure every 2–3 years.3 Things To RememberYour legal and tax entity structure should evolve as your business grows.Planning for sale or succession starts years in advance—don't wait.Holding companies, trusts, and installment strategies can drastically reduce taxes and protect assets.Useful LinksConnect with Jason Gabrieli: jgabrieli@HFMadvisors.com | LinkedInLike what you've heard… Learn more about HFM HERE Schedule time to speak with us HERE

In this week's episode of Business Lunch, Roland Frasier and Ryan Deiss continue breaking down the “Bottlenecks” framework—the 11 proven playbooks that billionaires use to grow, protect, and multiply wealth.From AI-driven acquisitions to tax-optimized exits, this conversation dives into the strategies that separate ordinary entrepreneurs from long-term empire builders. You'll hear how the world's wealthiest think about capital allocation, scaling “boring” businesses, and structuring companies for massive, tax-efficient exits.Whether you're scaling your first venture or managing a growing portfolio, this episode is a tactical deep dive into how to think—and act—like a billionaire.Key Takeaways • Tech Is Not a Moat: With AI making innovation easy to copy, your real advantage is distribution and users. • The QSBS Advantage: How the Qualified Small Business Stock exemption can eliminate up to $10M (or more) in capital gains per shareholder. • DAFs & Charitable Strategy: Donor Advised Funds can combine tax savings with long-term impact—if structured correctly. • Boring Businesses, Billionaire Results: Logistics, energy, and real estate can quietly create generational wealth when value is added and scaled. • Capital Cycling: Why the world's best investors (like Blackstone and Berkshire) act like banks—recycling capital and compounding returns.Episode Highlights [00:02:00] – Why tech is easy to copy—and why users, not code, create real enterprise value. [00:10:00] – The billionaire tax play: how QSBS and DAFs legally minimize or eliminate capital gains. [00:18:00] – When to start thinking about tax strategy (hint: usually not before $10M net worth). [00:25:00] – Logistics, land, and “boring” businesses that create quiet fortunes. [00:33:00] – The ESG arbitrage: adding sustainability to raise valuations. [00:40:00] – Network effects and marketplace rollups: creating compounding flywheels. [00:55:00] – The rise of “edge retail”: micro-brands, coffee chains, and inversion models that scale fast. [01:05:00] – Capital cycling and other people's money (OPM): how billionaires play the funding game.Memorable Quotes“If all you are is a feature that someone else could build, you don't have a business—you have a countdown clock.”“Boring businesses aren't boring when they compound quietly into billions.”“It's not what you make—it's what you keep.”“Billionaires don't think like operators; they think like capital allocators.”Mentioned in This EpisodeQualified Small Business Stock (QSBS) – U.S. tax exemption strategyDonor Advised Funds (DAFs) – Philanthropic and tax planning vehiclesRoss Perot Jr. – Logistics real estateDutch Bros – Scalable retail model exampleBlackstone & Berkshire Hathaway – Capital cycling and compounding modelsListen If You'reA founder or investor learning to structure smarter deals.A CEO or operator ready to scale beyond execution into capital allocation.A strategic thinker who wants to play the long game in business and wealth creation.ConnectHosts: Roland Frasier & Ryan DeissPodcast: Business Lunch with Roland FrasierMore at: businesslunchpodcast.comMentioned in this episode:Join Roland & Ryan at Get Scalable LiveIf you're a founder, CEO, or operator running a 7- or 8-figure business, Get Scalable Live was built for you. This is not your typical business event. It's 3 days of hands-on strategy, real-world frameworks, and next-level networking with the smartest operators in the game.

Dan Gray is the Head of Insights at Equidam.If you're a tech and investing nerd like us, you'll love this conversation. We cover everything Dan's learned reading dozens of academic research papers on startups and venture capital, debunking many popular narratives of the industry.We talk about the dangers of pre-mature startup scaling, the importance of origination stage investing, the concept of startup catering and why so many startups look the same, and the role of mega funds play in the ecosystem.We also discuss what the data says about concentration vs diversification, what VC's get wrong about pattern matching, and why pivoting is more valuable than you thinkThanks to Ramp for supporting this episode. It's the corporate card and expense management platform used by over 40,000 companies, like Shopify, CBRE and Stripe. Time is money. Save both with Ramp. Get $250 for signing-up here: https://ramp.com/ThePeelTry Harmonic - The startup discovery engine https://harmonic.ai/turnerTimestamps:(6:43) What's the required rate of return in VC?(9:29) Venture capital needs new definitions(16:10) QSBS(18:23) Are we in an AI bubble?(24:07) Re-branding early and late stage venture(28:25) We need more origination stage capital(40:05) Survivorship bias in emerging manager outperformance(42:57) Incentives driving larger fund sizes(48:10) Raising overvalued rounds re-risks a startup(52:08) Startup catering: why all startups look alike(58:42) Are VC mega funds still an experiment?(1:08:06) Late stage VC is competing with PE(1:13:42) a16z's Fund 1 strategy(1:18:18) How diversified should VC funds be?(1:25:06) Performance of Generalist vs Specialist firms(1:30:35) How to value a startup(1:40:58) Why VC firm location correlates to returns, but startup location does not(1:44:05) Founder background doesn't predict success(1:48:27) Startups with one pivot are most successful(1:50:24) Premature scaling kills 70% of startups(1:54:47) Does mega fund model work for origination investing?(1:56:15) Value of Twitter and writing onlineReferenced Research PapersVenture Predation: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4437360Process Alpha: https://angelspan.com/process-alpha-how-to-construct-and-manage-optimized-venture-portfolios-joe-milam-journal-of-portfolio-management-august-2022/The Sunk Cost Fallacy in VC: https://www.sciencedirect.com/science/article/pii/S0929119924000518Predictably Bad Investments in VC: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4135861Startup Catering to Venture Capitalists: https://afajof.org/management/viewp.php?n=58968Premature Scaling: https://innovationfootprints.com/wp-content/uploads/2015/07/startup-genome-report-extra-on-premature-scaling.pdfReferenced BooksThe Otherland Tetrology: https://www.goodreads.com/series/43762-otherlandPermutation City: https://www.goodreads.com/book/show/156784.Permutation_City?from_search=true&from_srp=true&qid=lf7FuUR9se&rank=1Necromancer: https://www.goodreads.com/book/show/6088007-neuromancer?ref=nav_sb_ss_1_29Other Referenced ItemsQSBS changes: https://www.dwt.com/blogs/startup-law-blog/2025/07/qsbs-big-beautiful-bill-tax-code-upgradesMega funds and the great re-risking: https://nextview.vc/blog/megafunds-and-the-great-re-risking/Rex Woodbury's post on hot companies: https://www.digitalnative.tech/p/the-taxi-cab-theory-of-venture-capitalThe VC Performance Paradox: https://www.linkedin.com/pulse/performance-paradox-venture-capital-dan-gray-2fqrePrior episodes mentionedDan Feder: https://youtu.be/_Ou6D9PLSBIMichael Dempsey: https://youtu.be/UzSbG6DL8CMSolugen: https://youtu.be/ofkNiB2nI3QFollow DanTwitter: https://x.com/credistickBlog: https://credistick.comFollow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakSubscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Welcome back to another episode of The Richer Geek Podcast! Today our guest is David Flores Wilson, founder of Sincerus Advisory and named an Investopedia Top 100 Financial Advisor. He helps entrepreneurs, tech professionals, and business owners maximize wealth, optimize equity compensation, and exit businesses the smart way. In this episode, David breaks down tax-saving strategies, the power of donor-advised funds, how to use real estate for wealth building, and why exit planning should start on day one, not the day you're ready to sell. If you want to keep more of what you earn and create a lasting financial plan, this conversation is a must-listen. In this episode, we chat about… How David's early experiences with family businesses shaped his career in financial planning. Why entrepreneurs need a different approach to financial planning than traditional employees. Strategies for deferring taxes and leveraging state residency for long-term savings. Understanding Qualified Small Business Stock (QSBS) and how it can save millions in taxes. The role of charitable giving strategies (like DAFs and charitable buyouts) in wealth preservation. Why exit planning should start when you form your business, not when you're ready to sell. How to balance wealth-building in real estate vs. stocks based on personal skills and opportunities. The emotional and identity shifts entrepreneurs face when selling a business. Key Takeaways: Entrepreneurs often need customized financial planning because most of their wealth is tied to their business. Tax deferral strategies can provide huge advantages, especially when combined with residency planning. QSBS can exempt up to $10 million in capital gains if structured correctly, an often-overlooked opportunity. Charitable giving can be structured to maximize both impact and tax benefits (e.g., bunching, DAFs, charitable redemptions). Real estate offers unique tax advantages but requires clear strategy and sometimes specialized partners. Exit planning isn't just about money, it's about legacy, lifestyle, and identity after the sale.   Resources from David LinkedIn | Sincerus Advisory | Blog: Planning to Wealth Resources from Mike and Nichole Gateway Private Equity Group |  Nic's guide  

Did you know that a tax benefit, the Qualified Small Business Stock (QSBS) tax exclusion, can save you millions? Discover how properly structuring your company from the start can lead to a tax-free sale of your C Corporation, potentially saving you millions. You'll learn the crucial steps to take now to prepare for a successful and highly profitable exit later. View the complete show notes for this episode. Want To Learn More? Allocation of Purchase Price & Taxes When Selling a Business Business Exit Plan & Strategy Checklist | A Complete Guide Why You Need to Consider Taxes Before Selling Your Business Additional Resources: Selling your business? Schedule a free consultation today. Sign up for an Assessment and Valuation of Your Business. Courses: The Art & Science of Selling a Business Download The Art of The Exit: The Complete Guide to Selling Your Business Download Acquired: The Art of Selling a Business With $10 Million to $100 Million in Revenue If you have any topic or guest suggestions, please email them to podcast@morganandwestfield.com.

Explore OB3 Act changes to QSBS rules, including the new $75M limit, $15M exclusion, and strategies to maximize tax savings for founders and investors. The American College of Trust and Estate Counsel, ACTEC, is a professional society of peer-elected trust and estate lawyers in the United States and around the globe. This series offers professionals best practice advice, insights, and commentary on subjects that affect the profession and clients. Learn more in this podcast.

Listen now: Spotify, Apple and YouTubeWhat if personal finance wasn't just about saving more or investing better—but about designing a life that feels meaningful, intentional, and aligned with your values?In this episode of Supra Insider, Marc and Ben sit down with Zach Teutsch, founder of Values Added Financial, to explore a radically human approach to wealth management. Instead of fixating solely on net worth, Zach helps high earners and tech professionals reframe their relationship with money, starting with life satisfaction and working backwards from there.They dive into the core questions that drive meaningful financial management, from how to balance ambition and family, to navigating equity compensation, sabbaticals, early-stage investing, and building a diversified “life portfolio.” Zach also shares tactical frameworks for spiky income years, Roth conversions, QSBS tax planning, and setting up estate plans that reflect your real priorities.Whether you're in tech, product leadership, or just rethinking how you manage money, this conversation will shift how you think about personal finance—from accumulation to alignment.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox

Send us a textSome entrepreneurs sell their companies and walk away with zero federal taxes. How? This is thanks to a strategy called QSBS.In this episode, tax strategist Alessandro of Get Dynasty breaks down Qualified Small Business Stock, new changes from the “Big Beautiful Bill,” and how founders can use trusts to multiply tax-free exits. If you're building or investing in startups, this could be the single most powerful tax break you'll ever use.

Welcome back to Belk on Business! I'm Josh Belk, and in today's episode, I'm diving into a new set of provisions from the recently passed “Big Beautiful Bill.” We're shifting gears from the last few episodes and breaking down five key areas: tax relief on overtime pay, updated estate and gift tax exemptions, gambling deduction limits, changes to qualified small business stock, and updates to FMLA and meal deductions.Whether you're an employer managing payroll, a high-net-worth individual planning your estate, or a business owner looking at stock-based growth, there's something in here that can affect your planning and your bottom line. Let's get into the details.3 Key TakeawaysNo Tax on Overtime (2025–2028): Employees in tip-eligible industries can deduct the overtime portion of their pay (above their normal rate) up to $12.5K (single) or $25K (joint), regardless of itemizing.Estate Tax Exemption Raised: The federal estate and gift tax exclusion jumps to $15M (plus inflation), giving families and high-net-worth individuals more room to plan.QSBS Gains Can Be Excluded: Qualified Small Business Stock purchased after July 1, 2025, may offer up to 100% capital gains exclusion if held for five years, or rollover options similar to a 1031 exchange.Episode Timeline & Highlights[0:00] - Recap of previous episodes and what's new in this one[1:15] - No tax on overtime explained: who qualifies and what's deductible[3:25] - Example breakdown of how overtime deduction works[6:32] - Employer payroll implications and what reporting might look like[6:57] - Estate and gift tax exemption increased to $15M[8:54] - Gambling losses now limited to 90% of winnings[10:04] - What is Qualified Small Business Stock (QSBS) and how gain exclusions apply[11:42] - Eligibility rules for QSBS, asset limits, and holding period[14:00] - Family Medical Leave Act credits made permanent[14:54] - Meal deduction changes—who still qualifies for 100%Links & ResourcesIRS Guidance on Overtime Tax Treatment (coming soon)Estate & Gift Tax Overview: https://www.irs.gov/businesses/small-businesses-self-employed/estate-and-gift-taxesQualified Small Business Stock (QSBS) Rules: https://www.irs.gov/pub/irs-drop/n-18-48.pdfFamily and Medical Leave Credit Info: https://www.irs.gov/newsroom/employer-credit-for-paid-family-and-medical-leaveIf this episode gave you a clearer understanding of the new tax provisions, don't forget to rate, follow, and review Belk on Business. And share it with a colleague or business owner who should be planning ahead. Until next time—stay smart and strategic.

In this episode of Future Focused: Sophisticated Estate Planning, hosts Michael Clear and Erin Nicholls are joined by Corporate Partners Scott McClure and Len Gray to discuss how the One Big Beautiful Bill Act (OBBBA) is expanding opportunities with qualified small business stock (QSBS). OBBBA brought about key updates to QSBS, including an increased capital gain exclusion amount, a higher asset threshold for a company to qualify as a small business, and reduced holding periods. Tune in, as this conversation emphasizes the importance of proactive tax planning for founders and business owners to maximize their benefits under this new legislation.

Jeff Levine joins us to break down one of the most surprising features of the new tax law: a brand-new type of deduction that could significantly change the way we think about AGI thresholds, phaseouts, and entity planning. In this episode, we unpack how the latest changes in the tax code are opening up advanced strategies for clients, and where financial planners need to stay sharp to avoid stealth cliffs and missed opportunities. Key Topics Covered: The new above-the-line deduction and who can benefit Planning around AGI phaseouts and stealth tax cliffs Leveraging non-grantor trusts for charitable and income planning Avoiding estate planning complacency amid exemption increases Rethinking entity structure in light of expanded QSBS rules Resources: Planning after tax changes Podcast: BBB Crossover Special A summary for tax planning This episode is brought to you by the AICPA's Personal Financial Planning Section, the premier provider of information, tools, advocacy, and guidance for professionals who specialize in providing tax, estate, retirement, risk management and investment planning advice. Also, by the CPA/PFS credential program, which allows CPAs to demonstrate competence and confidence in providing these services to their clients. Visit us online to join our community, gain access to valuable member-only benefits or learn about our PFP certificate program. Subscribe to the PFP Podcast channel at Libsyn to find all the latest episodes or search “AICPA Personal Financial Planning” on your favorite podcast app.  

Welcome to the Know Your Numbers REI podcast! In this episode, host Chris McCormack, founder of Better Books and a certified tax planner, dives deep into the recently passed law regarding Qualified Small Business Stock (QSBS) and its implications for small business owners and investors.Whether you're a small business owner contemplating a sale or an investor looking to maximize your returns, this episode is packed with valuable insights and strategies to help you navigate the complexities of tax planning.Don't miss out on this opportunity to learn how to keep more money in your pocket and reinvest in your future!Follow for more episodes and insights on tax strategies and real estate investing. If you have questions or need personalized advice, reach out to us at Better Books!••••••••••••••••••••••••••••••••••••••••••••➤➤➤ To become a client, schedule a call with our team➤➤ https://www.betterbooksaccounting.co/contact••••••••••••••••••••••••••••••••••••••••••••Connect with Chris McCormack on Social MediaFacebook: https://www.facebook.com/chrismccormackcpaLinkedIn: https://www.linkedin.com/in/chrismccormackcpaInstagram: https://www.instagram.com/chrismccormackcpaJoin our Facebook Group: https://www.facebook.com/groups/6384369318328034→ → → SUBSCRIBE TO BETTER BOOKS' YOUTUBE CHANNEL NOW ← ← ← https://www.youtube.com/@chrismccormackcpaThe Know Your Numbers REI podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests.

Canada's outdated capital gains policies are driving entrepreneurs and investors away. We need competitive tax reform to keep talent and investment here, building the businesses of tomorrow.We have just 33 small businesses per 1,000 people vs 124 in the US. Fixing our capital gains system could help us close this gap with the US and create hundreds of thousands of new jobs.Modern capital gains reform will unleash Canadian innovation, create more high-paying employment, and ensure our world-class graduates build their companies here, not elsewhere.GoalsTo ensure a prosperous, sustainable, and growing economy, Canada needs a thriving private sector that invests in new businesses. A strong environment for entrepreneurship creates jobs, drives GDP growth, and ensures economic mobility for all. In recent years however, entrepreneurship, and consequently private sector employment, has been slow despite an increasing population.One factor driving this change is that Canada's capital gains tax policies make it significantly less rewarding to start a business compared to other jurisdictions. To reverse this trend and reinvigorate our private sector, we must revise our outdated policies to align with global standards.Our targets:* Increase SMBs per 1000 people over the age of 18 from 33 to 62 to get half of the US rate of 124.* Increase the number of early-stage financing rounds (Pre-seed, Seed, Series A, and Series B) for new businesses from 482 in 2024 to over 1000+ per year.* Increase investments in new businesses through industry-agnostic venture capital financing to 0.5% of GDP, up from 0.35% of GDP, to get closer to the USA's figure of 0.72% of GDP.Background and MotivationNew business formation and growth relies on people taking huge risks with their time and money. However, today in Canada the people that take these risks – entrepreneurs, early stage employees, and investors – are rewarded less than in other countries.As a result the country's best talent is driven to leave and start businesses elsewhere, where they can find easier access to funding1 and keep more of the upside if they succeed.We need to reverse this systematic issue. By rewarding investors that put their capital at risk and supporting entrepreneurs who put their livelihoods on the line to create new companies we can create a strong and resilient economy.All companies begin as small and medium businesses (SMBs) and the formation and growth of these SMBs is essential to a country's economic success both through driving the quality of the labour market and creating opportunities for productivity growth.In Canada, SMBs accounted for ~64% of private sector employment and contributed to half of all net new jobs added last year2. These work opportunities support upward income mobility, lead to more capital being reinvested into local communities, and are particularly valuable for traditionally disadvantaged populations3 4 5.In addition, SMBs represent a significant portion of the economy and have high potential for productivity improvements6. Between 2017 and 2021, SMBs contributed almost half of Canada's GDP7. As these businesses grow and scale their operations they improve efficiency and drive productivity-led growth that can be equivalent in impact to roughly 5% of a developed nation's GDP8 9.Perhaps most importantly, SMBs turn into global winners. Growing these companies into sizable businesses is how a country can win an unfair share of global markets, by creating the large, export-focused corporations that contribute an outsized value to GDP and productivity growth. To ensure the next trillion dollar companies - the equivalent of Google, Microsoft, or Meta - are built in Canada, founders must be convinced to start their companies here.So, having a healthy ecosystem of SMBs is essential to creating a strong economy, but the data shows Canada is falling behind our global peers. In the 20 years between 2003 and 2023, the total number of Canadian entrepreneurs decreased by ~100K, despite the population growing by 10 million10 11. Today, for every thousand people over the age of 18 the US has ~124 SMBs12 13. Israel, a country with less than a quarter of Canada's population, has ~7314 15, while Canada has just ~3316.A significant driver of this stagnation is outdated and uncompetitive capital gains policies that have low limits, exclude large categories of business, and contain many restrictions compared to global peers - especially the US. It is less valuable for investors to put money into Canadian businesses, making capital more scarce and it discourages entrepreneurs who know that in most cases they could receive more reward by building the same company elsewhere. This makes it difficult for any SMB to get started let alone scale.Today, Canada has two capital gains policies, to try and encourage SMB creation, the Lifetime Capital Gains Exemption (LCGE) and a proposed Canadian Entrepreneur's Incentive (CEI) announced in Budget 2024 but not yet implemented. Combined, the LCGE and CEI would allow shareholders to reduce the inclusion rate of capital gains from the current 50% down to a range of 33.3%-0% to a cap of $3.25M 17 18.These policies simply can't compete with the US. The USA's Qualified Small Business Stock (QSBS) policy has a capital gains cap of $15M or ten times the original investment amount, five times higher than Canada's LCGE and CEI limit. In addition the QSBS is active today, while Canada's CEI cap has a phased approach only coming into full effect in 2029 if the policy is passed. Today in 2025, LCGE and CEI's true combined cap is only $1.25M. And while QSBS shields 100% of gains up until the policy cap for individuals and corporations, Canada's CEI would only shields 66.7% of gains for individuals.To illustrate how restrictive this is, we could imagine a company where the business is owned between founders, early employees, and various investors (see the first example below). If this business was started in 2018 and sold 7 years later today in 2025 for $100M, these risk-takers would have to pay a combined $14.7M in taxes. However, that same business with the same structure would pay no taxes in the US.The good news is that at larger scales of exit like $250m (see the second example below) the gap between Canada and the US decreases due to a more competitive basic capital gains inclusion rate in Canada. This means that if we match the QSBS's capital gains limit it could actually give the Canadian policy an edge driving more investment in the country and supercharging our SMB ecosystem. However, if we leave the policy as it stands right now companies can never get started because investors and entrepreneurs are scared away.The reason is that the QSBS rewards smaller exits - the majority of SMB outcomes - with the maximum capital gains tax value. This makes it easier for entrepreneurs, early employees, and investors to take on the risks of building a business. In fact, early-stage US investors are currently increasing their investments into new Canadian businesses, and adding in clauses that would require the Canadian business to reincorporate in the US simply to become eligible for QSBS. This means the best Canadian entrepreneurs and companies are leaving the country simply to take advantage of these rules. This decreases the health of our SMB ecosystem, prevents large companies from growing in the country and ultimately reduces tax revenue.If we want to keep our entrepreneurs, Canada's capital gains policies must become competitive with US policies.‍Beyond better gain caps and exclusion rates, the US's QSBS allows a wider range of businesses and stakeholders to benefit from the policy, with no minimum ownership requirements, increased asset value caps, and a tiered inclusion rate approach that incentivizes long-term business building. Meanwhile, Canada's CEI excludes companies in healthcare, food and beverage, and service businesses19. CEI's minimum ownership rules also exclude early employees and investors who own less than 5% of the business at the time of sale.Most importantly, while LCGE and CEI's $3.25M cap applies over a taxpayer's entire lifetime, QSBS's limits are per issuer or business. In other words, entrepreneurs, early employees, and investors can use the QSBS more favourable policy again and again for subsequent companies. This discourages repeat entrepreneurs in Canada, who statistically have a higher chance of building successful businesses, from creating a second or third company, as Canada's LCGE and CEI don't extend to new issuers20 .What Needs to Be DoneTo properly reward risk takers, Canada can fully solve our capital gains policy problems by combining the LCGE with the CEI into a simple, powerful capital gains policy that supports entrepreneurs. In particular, the new policy could become competitive by adopting three major changes:1) Expand the eligibility requirements to ensure Canadian entrepreneurs and risk takers are supported. Eligible business types should be expanded to include all industries of national interest, including healthcare clinics, clean energy, technology, etc. We should also eliminate 5% minimum ownership requirements to enable any individual or corporate entity to claim CEI deductions in accordance with the tiered approach that is used to support early-stage employees and investors.2) Improve the capital gain exclusion rate system to be globally competitive, supporting entrepreneurs and increasing investment. To prevent the draw of foreign jurisdictions and ensure that we have just as much incentive to start companies as peer countries, we should start by raising the exclusion cap to $15M gain or 10x adjusted cost basis per taxpayer, whichever is greater.3) Make structural changes to ensure these new policies scale appropriately. Amend the capital gains limit from applying per lifetime to per business to incentivize repeat entrepreneurs to continue building in Canada. Additionally, ensure that common investment structures, including Simple Agreements for Future Equity (SAFEs) and Convertible Notes, become eligible, with the holding period commencing from the date the investment is signed, not when the shares are priced and converted. So, there are no major discrepancies for startups choosing to operate in Canada compared to the US.Common QuestionsWill this only benefit tech startups?No. Canada's LCGE was originally created to support all small businesses and increase competition, which includes non-tech businesses such as fisheries and farmers. Our memo recommends expanding eligibility to all industries deemed essential, including non-tech ones, that the current CEI proposal omits, such as healthcare practitioners. In the US, SMBs of all sectors, including manufacturing, retail, wholesale, consumer, and packaged goods, benefit from the QSBS policy21.Wouldn't corporate tax breaks reduce tax income for social programs and only benefit the wealthy 1%?No, this would encourage investment in Canadian small businesses, essential for increasing corporate tax revenue that funds social programs. Businesses that receive investment can generate more jobs, pay higher wages, which help increase individual income tax revenue, and reduce withdrawals from crucial social assistance programs, such as Employment Insurance, as more companies and workers stay in Canada. This helps reduce the burden and improve access to social programs, rather than removing them.What stops foreign investors from abusing this and using Canada as a tax-sheltered haven to enrich themselves at the expense of Canadians?Maintaining Canadian incorporation, assets, residency, and operating requirements, combined with a minimum 2-year waiting period before benefits kick in, will ensure that new businesses maintain a presence in Canada, creating skilled job opportunities for Canadians and contributing to local economic growth.Why should we invest in SMBs? Aren't they risky and likely to be shut down in a few years?68% of SMBs in Canada survive and operate into their fifth year, and a further 49% of SMBs survive and operate for more than a decade22. SMBs around the world, including Canada, contribute significantly to economic output, job opportunities, and increased competition for consumers.ConclusionCanada needs to create an ecosystem that supports entrepreneurs at the earliest stages. We have one of the most educated countries globally, with the largest college-educated workforce among G7 countries23. Canadian universities are consistently ranked among the top institutions globally, world-renowned, with research labs led by leaders like Geoffrey Hinton, dubbed the “Godfather of AI,” who was recently awarded a Nobel Prize for his work in AI and ML24 25.Not only is our population talented, but they are also resourceful and hardworking. Rather than punishing them, we should reward them for taking the risks to build Canada's economy. To start, we should implement a modern capital gains policy that rewards investors, entrepreneurs and early employees.Read more here: https://www.buildcanada.com/en/memos/reward-the-risk-takers This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com

What's in the One Big Beautiful Bill Act — and how does it impact your taxes, family, equity comp, and retirement? In this episode of The Liquidity Event, AJ Ayers and John Owens break down the OBBB and what it means for high earners, tech professionals, parents, retirees, and everyone in between. We also chat micro-retirements, the new NYC mayor, charitable gifting changes, and yes, beavers with zoning issues. Key Timestamps: (00:00) Introductions (03:09) Zohran Mamdani the new mayor of NYC (07:30) Gen Z discovers micro-retirement and taking vacations (11:01) Beavers build a local dam in the Czech Republic while authorities await permit (12:54) One Big Beautiful Bill: What does this mean for Brooklyn Fi clients? (14:49) OBBB and QSBS (18:23) What does the OBBB have to do with parents of young children? (22:34) BKFi Boomers: What can the OBBB do for senior citizens (26:01) How to give back to those negatively affected by OBBB (28:03)Charitable Gifting Changes and the OBBB (31:09) Listener Question: How do I find the right accountant?   If you're still curious about the One Big Beautiful Bill and how it will affect you, register here for our webinar on July 23. We'll explain everything you need to know.   

In this episode, Dr. Preston Cherry explains how to take advantage of the new rules that could save you 20% on qualified income every year and unlock up to $10 million in tax-free gains when you sell or exit your business. From avoiding costly timing mistakes to structuring smart early, Dr. Cherry breaks down what it really means to build a tax-smart runway.Takeaways:• 20% income deduction• $10M+ capital gains = 0% tax• QBI = annual savings• QSBS = tax-free exit• Timing = everything00:00 Intro01:00 Tax Strategies Simplified04:51 Optimizing QBI and QSBS Strategies06:23 Empower Your Growth JourneyGet The Wealth Word — our free weekly newsletter on wealth and well-being: https://wealth.concurrentfp.com/thewealthwordExplore award-winning wealth advisory services: https://www.concurrentfp.com/Read Wealth In The Key of Life by Dr. Preston Cherry: https://drprestoncherry.com/book/Disclosure: Educational content only. Not financial advice. https://www.concurrentfp.com/disclosures/

Group Chat News is back with the hottest news of the week including Trump calls Elon's third party "ridiculous." Your kid is getting a ‘Trump account.' Should you put your money in it, Trump's One Big Beautiful Bill Act (OBBBA) offers an incredible incentive to startup founders and early employees with more lenient QSBS, President Trump announces plans for UFC fight on White House grounds in honor of America 250, TikTok Building New Version of App Ahead of Expected U.S. Sale, China Plans Nationwide Subsidies to Boost Birthrate. 

Today's show:Startup exits are heating up with $67.7B in Q2 activity, QSBS just got a major expansion, and Robinhood is pushing boundaries with tokenized SPVs. In this episode, @Jason and @alex break down what it all means for founders and investors, plus the rise of Elon's “America Party,” TikTok's potential reboot, and why SaaS startups must rebrand around AI to stay competitive. A must-watch for anyone building, investing, or navigating tech in 2025.Timestamps:(04:29) Jason's thoughts on Elon Musk's America Party(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist(15:02) M&A keeps heating up and why a big fintech IPO could be on the way!(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(26:32) Unpacking liquidation preferences for non-experts(29:11) AI companies are soaking up the majority of investment dollars but what does that really MEAN?(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code TWiST(36:26) Why Jason's group chat will love the QSBS expansion but it's not really that big of a deal…(46:27) TikTok seems poised to make a deal… Why Jason thinks they do pose a national security threat.(59:22) Why is CoreWeave picking up Core Scientific, and is now a good time to sell your shares?Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://www.twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcpFollow Lon:X: https://x.com/lonsFollow Alex:X: https://x.com/alexLinkedIn: ⁠https://www.linkedin.com/in/alexwilhelmFollow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanisThank you to our partners:(10:05) Oracle - Try OCI and save up to 50% on your cloud bill at https://w⁠⁠⁠⁠ww.oracle.com/twist(20:00) OpenPhone - Streamline and scale your customer communications with OpenPhone. Get 20% off your first 6 months at https://www.openphone.com/twist⁠(30:02) MonarchMoney - Get 50% off your first year by going to MonarchMoney.com and using the offer code TWiST.Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarlandCheck out Jason's suite of newsletters: https://substack.com/@calacanisFollow TWiST:Twitter: https://twitter.com/TWiStartupsYouTube: https://www.youtube.com/thisweekinInstagram: https://www.instagram.com/thisweekinstartupsTikTok: https://www.tiktok.com/@thisweekinstartupsSubstack: https://twistartups.substack.comSubscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

Brent talks about what tax planning can happen AFTER the client has already signed the deal to sell a large asset. He talks about the difference between income and estate tax planning. He then discusses terms of the deal, installment method, QSBS, charitable giving, charitable lead annuity trusts, and how discounts may still be available on gifts, even after the ink is dry.

At Interplay, I've spent years working with entrepreneurs who are driven to build, scale, and make an impact - but too often, legal structuring gets overlooked in the frenzy of product development and fundraising. I've seen firsthand how costly early legal missteps can be so we brought on legal expert Eric Broad of Bowery Legal on to the pod to demystify early stage startup legal questions from entity type selection to the nuanced tax advantages like QSBS that most founders only hear about once it's too late. Our goal at Interplay is to equip founders with practical insights so they can focus on growing transformative businesses without getting tripped up by preventable legal issues. Whether you're about to raise your first dollar or just brainstorming your MVP, this conversation will help you make smart, strategic choices. We cover the why behind Delaware's dominance, when to hit the "incorporate" button, and why trying to hack the system with clever workarounds rarely works in your favor. I hope this deep dive helps founders avoid headaches and build with confidence.Links:Eric Broad: LinkedInBowery Legal: Website, LinkedInPhuong Ireland: LinkedInBook: The Fundraising RulesInterplay: Website, LinkedIn, TwitterMPD: LinkedIn, Twitter

In this special episode of The Liquidity Event, BKFi leaders John and AJ interview tax attorney Christopher Karachale about Qualified Small Business Stock (QSBS) - a powerful tax benefit allowing founders to exclude up to $10 million (or more) from capital gains taxes when selling shares. Key Timestamps: 1:50 - What is QSBS? The $10 million exclusion explained 3:16 - History of QSBS: From 1992 to today's 100% exclusion 8:15 - Qualification requirements: Company & shareholder criteria 11:13 - "Qualified trade or business" explained 12:18 - Prohibited business categories 14:14 - Tips for founders to qualify for QSBS 18:30 - LLC conversion strategies for QSBS 20:45 - Fixing past entity mistakes to qualify 22:54 - LLC to C-Corp conversion: FMV basis benefit 26:15 - 1045 rollovers: Strategy for selling before 5 years 29:04 - QSBS stacking: Advanced strategies with trusts 35:38 - Practical advice for early-stage founders Connect with us: Email: liquidityevent@brooklynfi.com Leave a voicemail: memo.fm/liquidityevent Don't forget to like, subscribe, and leave a review! New episodes every Friday. #FinancialAdvice #IPO #StartupTips #AIInfrastructure #Entrepreneurship  

This episode is brought to you by ⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠*This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  *   As an American searcher, are you aware that you might be able to receive $10M+ of your exit proceeds completely free of federal tax? As a Canadian searcher, are you aware that you might be able to receive $1M+ of your exit proceeds completely free of federal tax? If you're not, then you might want to give this episode a listen. We split today's episode into two parts: The first half will focus on US searchers and investors, and will explore the QSBS program (aka Section 1202) offered by the US federal government. The second half (starting at the 47 minute mark) will focus on Canadian searchers and investors, and will focus on the CCPC program and the lifetime capital gains exemption offered by the Canadian federal government. Both programs have the potential to be incredibly lucrative for searchers and investors alike, though both remain unfamiliar to many. I hope this episode plays a small role in changing that. Timestamps - USA: 0:00 - 47:00- Canada: 47:00 - 1:11:00

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Origins host Beezer Clarkson sits down with her colleague Laura Thompson, fellow LP and Partner at Sapphire Partners, to unpack her recent conversation with Jessica Archibald, a GP at Top Tier Capital. They discuss Jessica's engineering-based analytical approach to answering the question “what makes a franchise?” and discuss some surprising things they learned - Jessica's view that there's only one real way to do succession, the importance of breaking good and bad news in a way that creates a performance culture, and whether or not they're going to adopt Jessica's policy of assigning letter grades to funds at Sapphire Partners. Learn more about Sapphire Partners: sapphireventures.com/sapphire-partners Learn more about OpenLP: openlp.vc Learn more about Asylum Ventures: asylum.vc Learn more about Top Tier Capital Partners: ttcp.com Read Laura Thompson's blog on why venture reserves aren't always a good thing: sapphireventures.com/blog/dirty-secret-venture-reserves-are-not-always-a-good-thing/ Read Laura Thompson's blog on fund recycling: sapphireventures.com/blog/fund-recycling-moves-the-needle-for-both-lps-and-gps-heres-how/ Read Laura Thompson's blog on QSBS: sapphireventures.com/blog/how-lps-gps-and-founders-can-leverage-qsbs-to-make-more-money/ Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox. CHAPTERS: (0:00) - Intro (1:08) - Jessica Takes It In a Different Direction (3:41) - Communicating with your LP base (So There Aren't Surprises) (7:15) - Franchise Funds Are Intentional (9:44) - Getting to 1x DPI in Nine Years (15:55) - 2x is the new 3x (19:43) - Giving Funds Letter Grades

Origins host Beezer Clarkson sits down with her colleague Laura Thompson, fellow LP and Partner at Sapphire Partners, to discuss her recent conversation with Stephen Bluestein, Partner of Primary Investments at Adams Street and formerly Packard Foundation, about what it takes to make (and potentially later break) a franchise fund in venture. Together, Beezer and Laura debrief their top takeaways, including: do the hallmarks of a franchise differ between GPs and LPs (or even amongst different LPs); how does a franchise produce a lights-out 5x or 10x fund at their fund size; is a consistent 2x net good enough; parallels of sports franchises; and, does the right to win with the best founders mean you will then deliver the best returns? Learn more about Sapphire Partners: sapphireventures.com/sapphire-partners Learn more about OpenLP: openlp.vc Learn more about Asylum Ventures: asylum.vc Learn more about Adams Street Partners: adamsstreetpartners.com Read Laura Thompson's blog on why venture reserves aren't always a good thing: sapphireventures.com/blog/dirty-secret-venture-reserves-are-not-always-a-good-thing/ Read Laura Thompson's blog on fund recycling: sapphireventures.com/blog/fund-recycling-moves-the-needle-for-both-lps-and-gps-heres-how/ Read Laura Thompson's blog on QSBS: sapphireventures.com/blog/how-lps-gps-and-founders-can-leverage-qsbs-to-make-more-money/ Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

Learn how to minimize taxes and maximize your wealth. Curious about how successful entrepreneurs hold onto more of their money and grow their wealth? In this episode, we focus on tax optimization and financial planning strategies, covering everything from tax-saving structures to leveraging offshore and domestic opportunities. Whether you're planning an exit, exploring international investments, or securing your income, you'll gain valuable insights to prepare for the future. Today's guest, Vincenzo Villamena, founder of Online Taxman, is an expert in tax preparation, accounting, and offshore structuring. With Big 4 experience, private equity advising, and expertise in real estate and international transactions, Vincenzo brings valuable insights on protecting and growing wealth. Based in Rio de Janeiro, he offers a global perspective you won't want to miss. In this episode you will: Proper tax planning can save entrepreneurs millions, especially when preparing for a business exit. Offshore structuring offers significant tax benefits, including reduced rates and income exclusions for U.S. expats. Relocating to Puerto Rico provides unique tax advantages, such as a 4% tax rate and zero capital gains tax for qualifying income. Asset protection strategies, like international trusts, safeguard wealth from potential legal risks and frivolous lawsuits. Entrepreneurs should clean up financial and legal records well in advance to avoid complications during due diligence. Subscription models and low churn rates increase a business's valuation and attractiveness to potential buyers. Long-term planning, including leveraging QSBS and 1031 exchanges, can maximize tax savings and investment returns. All this and more, on this week's episode of Beyond 7 Figures. Links: https://onlinetaxman.com/ https://predictableprofits.com/ https://www.youtube.com/@PredictableProfits https://www.facebook.com/PredictableProfits https://www.linkedin.com/company/predictable-profits/

Nick Chirls, GP at Asylum Ventures,  and Beezer Clarkson, LP at Sapphire Partners go deep into their recent conversation with Wesley Chan, the Co-Founder and Managing Partner of FPV Ventures. They unpack Wesley's direct learnings from Sergey Brin coming up at Google, how it is the job of the investor to spot greatness, his views on company pivots (and how they oppose another recent guest, Mike Maples' views on pivots), the difficulties of thinking independently in Silicon Valley, and the serendipitous way Wesley and Sapphire Partners wound up working together in the first place. Plus Nick, it turns out, is kind of a tax guy. He and Beezer discuss the hidden benefits of being an expert on QSBS. Learn more about Sapphire Partners: sapphireventures.com/sapphire-partners Learn more about OpenLP: openlp.vc Learn more about Asylum Ventures: asylum.vc Learn more about FPV Ventures: fpvventures.com Read Laura Thompson's article on QSBS: sapphireventures.com/blog/how-lps-gps-and-founders-can-leverage-qsbs-to-make-more-money/ Listen to Mike Maples & Jai Das discuss pivots: open.spotify.com/show/23H0tOX63xMChV2SErQKnZ?si=a9aab8b3e4c34dde Subscribe to the OpenLP newsletter for a monthly roundup of the latest venture insights, including the newest Origins episodes, delivered straight to your inbox.

Host Gary J. Ross discusses the Qualified Small Business Stock (QSBS) exclusion with Roger Royse, partner in the Palo Alto office of Haynes and Boone, LLP. Gary and Roger go over the history of QSBS, and Roger talks about how important QSBS is today to investors in emerging companies. The various QSBS requirements are described, including the necessity for being a C corporation, the holding period and how it is counted, and the growth assets test. Roger closes out the episode by noting common pitfalls of QSBS such as delays in incorporation or exercising options, S-elections, company distributions, and secondary sales.

 Is It Time To Upgrade Your Tax Team?  Forward Thinking Tax Strategies  Ready to unlock the tax secrets that could save you thousands and accelerate your business growth? Join Marcia Riner and tax expert David Snider, CEO of Harness Wealth, as they dive into tax strategies that go beyond mere compliance. Think your current tax team has your back? Think again. From choosing the right business structure to discovering little-known tax incentives, David sheds light on ways your tax strategy might be holding your business back. Whether you're planning to expand, acquire, or even sell, this episode will open your eyes to how proactive tax planning can be a powerful growth engine. It's time to think forward and ask: Do you have the right tax team to get you there? Key Talking Points & Timestamps [00:02:05] Meet David Snider David's impressive journey from Bain Capital to founding Harness Wealth. How his experiences drive his mission to make tax and financial guidance accessible. [00:03:30] Business Structuring for Tax Optimization Understanding the impact of business structure on taxes, from QSBS benefits to choosing the right entity. [00:06:40] Differences Between Tax Planning & Compliance David outlines the proactive nature of tax planning vs. typical compliance, emphasizing the value of ongoing advisory. [00:09:15] Real-Time Tax Strategy How “safe harbor” rules, estimated taxes, and cash flow timing can protect your business from unexpected liabilities. [00:12:40] Entity Choice & Tax Advantages Post-2017 Tax Cuts implications and benefits of alternative structures like multi-member LLCs and S-Corps for reducing state taxes. [00:16:55] Proactive Tax Advisory for Business Growth The importance of having a tax advisor who's actively monitoring your business goals, potential industry changes, and tax policy shifts. [00:22:25] Leveraging Tax Advisors as Strategic Growth Partners From R&D credits to location-based incentives, David discusses the tax tools that can significantly lower operational costs for growth. [00:25:30] Specialized Advisory for Niche Markets Why niche-focused tax advisors, who understand the unique needs of your industry, can boost growth faster than a generalized approach. [00:27:40] Outsourced CFO Services When and how businesses can benefit from outsourced CFO support as part of their tax advisory for financial forecasting and strategic cash flow management. Conclusion: If you're still wondering whether your current tax team has what it takes to drive your business forward, this episode is your wake-up call! David Snider reveals the possibilities that come with having a proactive, forward-thinking tax advisor in your corner—someone who can help you navigate tax policies, optimize cash flow, and fuel your company's growth goals. With the right tax team, you're not just saving money—you're setting your business up for lasting success. Take advantage of David's exclusive offer and get a complimentary consultation at https://harnesswealth.com/Marcia. Remember, the best investment you can make is in a tax strategy that aligns with your vision for growth!   Subscribe & Learn More: Don't miss future episodes of Profit with a Plan, where we share tips and strategies to grow your business and increase profitability. Subscribe on your favorite podcast platform      These notes are optimized for keywords such as Forward-thinking tax strategies, Business tax planning, Outsourced CFO for small business growth, Optimize taxes for business growth and Tax team for business sale planning.     This episode is sponsored by Infinite Profit ® —We don't just talk profit — we deliver it! Is your business ready for explosive growth? Visit InfiniteProfitConsulting.com to learn how Marcia and her team can help you boost profits and set your business up for long-term success.     Grab Your Free Resource: Looking to supercharge your profits? Download Marcia's Profit Booster Playbook at BoostingProfit.com to uncover three essential strategies to increase your bottom line today.     About Marcia Riner.  She is a business growth strategist who helps business owners dramatically increase their revenue, profit, and the value of their company. In fact, she can show prospective clients a clear pathway to profit and an impactful ROI for working here before hiring her firm. Through her proven Profit Booster® strategies, she gets results. Marcia is the CEO of Infinite Profit® and more information can be found at https://www.InfiniteProfitConsulting.com Got questions?  Reach out to Marcia and her team at (949) 229-2112 ♾️

Charley Ma and Mahdi Raza are the Co-founders of Pathlight Ventures, and were early employees at five unicorns, Plaid, Ramp, Alloy, Robinhood, and Stytch. They share tactical advice for early stage startup employees, lessons getting Plaid and Ramp their first customers, and deciding to build Pathlight together. Timestamps(00:00) Intro(02:30) Growing up in basements(05:15) Charley's journey to first biz hire at Plaid(15:01) Advice on being a good startup employee(19:34) Mahdi's path to Robinhood(26:33) Deciding between joining an early or late stage startup(32:39) Why Charley joined Plaid despite VCs telling him not to(38:52) Benefits of case studies in hiring(39:58) Why every hyper growth company is a shit show(44:24) Startup comp: equity, QSBS, early exercise, vesting(49:59) Joining Ramp as the first Head of Growth(58:35) How Ramp got its first customers(01:02:06) Advice and common traps on early GTM strategies(01:05:04) Why $1M ARR does not mean you have PMF(01:06:51) Meeting when Robinhood bought, churned, then returned to Plaid(01:09:54) Deciding to build Pathlight together(01:23:06) Raising Fund 1 in 2021 and how bad timing almost killed it(01:29:55) Reasons founders work with Pathlight(01:32:04) Why most investors add no value and give bad advice(01:36:44) Founders Pathlight invests in + Artie case study(01:44:44) Competing with incumbent funds(01:53:57) Raising a $75m Fund 2 in 2023(02:02:22) Are Seed extensions good investments?(02:07:45) Discussing startup valuations(02:09:09) Mahdi's 10-minute market outlook (as of 8/8/24) Referencedhttps://www.pathlight.vc/https://plaid.com/https://robinhood.com/us/en/https://ramp.com/https://stytch.com/https://www.alloy.com/https://www.artie.com/ Follow CharleyTwitter: https://twitter.com/charleymaLinkedIn: https://www.linkedin.com/in/charleyma Follow MahdiTwitter: https://twitter.com/mahdirazamrLinkedIn: https://www.linkedin.com/in/mahdirazany Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovakNewsletter: https://www.thespl.it/  

In this episode of Weaver: The Alternative Edge, hosts Blayne Lowary and Vardeep Mann delve into the intricacies of Qualified Small Business Stock (QSBS). This conversation provides crucial information for investors and fund managers looking to maximize tax benefits through QSBS. Lowary and Mann bring valuable insights into how QSBS can be a significant advantage for non-corporate taxpayers, providing substantial exclusions on capital gains. Key Points: • QSBS can provide substantial tax exclusions, potentially excluding up to $40 million of gain from taxable income.• Claiming QSBS benefits requires proper documentation and portfolio company representation.• Investors should be aware of pitfalls like warehouse investments and subsequent closes, which may disqualify QSBS eligibility. Lowary and Mann discuss the key aspects and potential challenges of Qualified Small Business Stock (QSBS). They emphasize the importance of understanding QSBS eligibility criteria, including the need for proper documentation and portfolio company representations. “One of the requirements for stock to be eligible for QSBS is it has to be received upon original issuance,” Lowary said.Additionally, the discussion covers critical gray areas, such as the impact of convertible notes and SAFEs on QSBS eligibility and the complexities surrounding carried interest. “Convertible notes and SAFEs are a gray area, specifically regarding when the clock starts for the five-year hold period,” Mann said. This episode serves as an essential guide for those navigating the QSBS landscape. Subscribe and listen to future episodes of Weaver: The Alternative Edge, on Apple Podcasts or Spotify.©2024

Join us for a jam session where I break down several startup ideas from the SIP community. I'll share my insights on why these ideas are promising or problematic, and reveal the frameworks and strategies I'd use to grow these businesses. In this episode, we explore diverse opportunities, including affiliate websites, loyalty programs, DTC brands, and more. Discover the evaluation techniques and growth strategies that can help you build your next successful startup. Whether you're aiming to launch your first million-dollar business or are interested in entrepreneurial tactics, this episode is packed with actionable advice and inspiration. Don't miss this essential guide to launching a thriving startup!

Episode 541: Shaan Puri (https://twitter.com/ShaanVP) and Sam Parr (https://twitter.com/theSamParr) are on a campaign to make sure no entrepreneur pays more taxes than absolutely necessary. They're joined by Ankur Nagpal, the founder of Teachable and resident tax genius, to share the 10 tax loopholes every founder should know.  No more small boy spreadsheets, build your business on the free HubSpot CRM: https://mfmpod.link/hrd — Show Notes: (0:00) Intro (3:00) Biggest secret to pay less in taxes (6:20) QSBS - the most generous tax break available (15:30) Do NOT move to Puerto Rico (20:00) There's no true alpha in investing (25:00) Sam's credit card tax hack (29:00) Solo 401(k) (33:30) Your CPA is not is not your tax strategist (41:30) Owning real estate to lower your tax bill (43:00) 4 triggers to happiness (47:30) Putting the Indian diet on blast — Links: • Ankur Nagpal Twitter - https://twitter.com/ankurnagpal • Teachable - https://teachable.com/ • Carry - http://carrymoney.com/ • Mo Points - https://mopoints.com/ • Points.me - http://points.me — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth Check Out Shaan's Stuff: • Try Shepherd Out - https://www.supportshepherd.com/ • Shaan's Personal Assistant System - http://shaanpuri.com/remoteassistant • Power Writing Course - https://maven.com/generalist/writing • Small Boy Newsletter - https://smallboy.co/ • Daily Newsletter - https://www.shaanpuri.com/ Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. — Other episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto • #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

Episode 528: Shaan Puri (https://twitter.com/ShaanVP) and Sam Parr (https://twitter.com/theSamParr) answer the question they get most often: “If you had to pick one idea that to make a million dollars this year, what would it be?”  No more small boy spreadsheets, build your business on the free HubSpot CRM: https://mfmpod.link/hrd — Show Notes: (0:00) Intro (3:00) Idea 1 - The "Me Also" strategy (12:00) Idea 2 - Niche community that solves for X (16:00) Idea 3 - QSBS advisory firm (24:00) Idea 4 - Pizza robots (44:00) Idea 5 - Buying a university — Links: • Quiet Light - https://quietlight.com/ • Exit Five - https://www.exitfive.com/ • Figure - http://figure.ai/ • Renovate Robotics - https://www.renovaterobotics.com/ • Anduril - https://anduril.com/ • DealStream - https://dealstream.com/ — Check Out Shaan's Stuff: • Try Shepherd Out - https://www.supportshepherd.com/ • Free 2024 Goal-Setting Session - https://planfor2024.com/ • Shaan's Personal Assistant System - http://shaanpuri.com/remoteassistant • Power Writing Course - https://maven.com/generalist/writing • Small Boy Newsletter - https://smallboy.co/ • Daily Newsletter - https://www.shaanpuri.com/ Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com/ Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. — Other episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto • #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More