Podcast appearances and mentions of spencer hilligoss

In this power-packed episode of The Real Estate Vibe Show, Vinki Loomba and special guest Spencer Hilligoss dive into the critical art of vetting sponsors for passive real estate investing in 2025. With the right sponsor, your investment can soar—but how do you find the right one?Spencer Hilligoss, CEO and co-founder of Madison Investing, shares his real-world insights on how to vet sponsors and operators in the fast-evolving world of passive real estate investing.Key Takeaways:Track Record Matters—But Not Just The Numbers: Spencer emphasizes that a sponsor's experience is crucial, but even more important is how they managed the deal. Ask about previous successes, but also be open to understanding any challenges and how they were overcome.The Power of Approach: Sponsors with a clear, repeatable business process are more likely to succeed. Spencer shares how sponsors should know their operational playbook inside out and be able to articulate it clearly.Communication Is Key: Look for sponsors who communicate openly, especially during tough times. Ask for examples of when they've had to deliver bad news to investors and how they handled it.Alignment of Interests: Ensure the sponsor's financial interests align with yours. Look at their fee structures and the profit-sharing model. Sponsors with too-high fees may have conflicting priorities that affect your returns.The Importance of Values: Vetting a sponsor goes beyond finances. Sponsors who prioritize ethical treatment of tenants and value safety and community-building show long-term responsibility and vision.

Hey everyone! Join us as we chat with Spencer Hilligoss, a tech whiz turned real estate investor! Spencer dives into how his tech background helped him excel in real estate, focusing on big, predictable projects like multifamily and self-storage. He also shares the secrets behind his real estate investing club and his 5-step vetting process for finding the best deals. If you're a techie curious about real estate or just looking for investment tips, this episode is for you!   ======================== ======================== ================= Want to grow your real estate investing business and portfolio?  You're in the right place. Welcome to the Property Profits Real Estate Podcast

Investment expert Spencer Hilligoss of Madison Investing joins host Paul Shannon to discuss the essentials of vetting real estate sponsors. From building your network to identifying financial red flags, Spencer shares his five-part framework for evaluating a sponsor's track record, team, communication style, and more. Discover why the sponsor's personal balance sheet matters, how to tell if they truly care about tenant experience, and when it's time to walk away- no matter how good the deal appears on paper. If you're looking to elevate your due diligence process and make more informed investing decisions, this conversation is a must-listen. Today's Episode Takeaways: - Why personal referrals often trump paid ads or internet searches - Spencer's five-part sponsor vetting framework (track record, approach, team, communication, values) - “Failure response” and why sponsors who have faced adversity can be more reliable - The crucial differences between investing for cash flow vs. wealth building - Practical questions to ask every sponsor before wiring your funds Don't forget to subscribe and leave a review so you never miss out on more expert insights on real estate and passive investing! Take our Survey: PassivePockets.com/Survey Disclaimer: The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk, so use your best judgement and consult with qualified advisors before investing. You should only risk capital you can afford to lose. Remember that past performance is not indicative of future results. This podcast may contain paid advertisements or other promotional materials for real estate investment advisers, investment funds, and investment opportunities, which should not be interpreted as a recommendation, endorsement or testimonial by PassivePockets, LLC or any of its affiliates. Viewers must conduct their own due diligence and consider their own financial situations before engaging with any of the advertised offerings, products or services. PassivePockets, LLC disclaims all liability for direct, indirect, consequential or other damages arising out of reliance on information and advertisements presented in this podcast. Contact Us At: jimpfeifer@biggerpockets.com

What if achieving financial freedom isn't just about earning more and building investments that align with your values and goals? Spencer Hilligoss, CEO of Madison Investing, joins Dr. Felecia Froe to share his journey from corporate FinTech to becoming a leader in alternative investments.   In this episode, Spencer reveals how to create multiple income streams, keep passive investments genuinely passive, and confidently navigate real estate's complexities. He emphasizes the importance of selecting trustworthy partners, valuing long-term impact, and staying resilient through challenges.   Curious how to build a life of financial independence while making a difference? Don't miss the actionable insights and inspiring stories in this conversation. Tune in today!   01:12 - The Journey to Financial Awareness 06:24 - Exploring Alternative Investments 14:40 - Investing with Strategy and Confidence 25:04 - Keeping Passive Investments Truly Passive 36:00 - Values-Driven Investing and Long-Term Impact   Connect with Spencer! Website: https://www.madisoninvesting.com/ LinkedIn: https://www.linkedin.com/in/shilligoss/   Be the Boss of Your Own Money and Own Your Future. Connect with us and Discover Investment Strategies Designed to make a Difference. Website: https://moneywithmission.com Linkedin: https://www.linkedin.com/in/moneywithmission   Key Quotes: "Competence creates confidence. The more you learn, the more confident you become in making big decisions." - Spencer Hilligoss   "Diversification isn't just smart—it's essential. A single income stream can leave you in hot water faster than you realize." - Spencer Hilligoss

What if achieving financial freedom isn't just about earning more and building investments that align with your values and goals? Spencer Hilligoss, CEO of Madison Investing, joins Dr. Felecia Froe to share his journey from corporate FinTech to becoming a leader in alternative investments.   In this episode, Spencer reveals how to create multiple income streams, keep passive investments genuinely passive, and confidently navigate real estate's complexities. He emphasizes the importance of selecting trustworthy partners, valuing long-term impact, and staying resilient through challenges.   Curious how to build a life of financial independence while making a difference? Don't miss the actionable insights and inspiring stories in this conversation. Tune in today!   01:12 - The Journey to Financial Awareness 06:24 - Exploring Alternative Investments 14:40 - Investing with Strategy and Confidence 25:04 - Keeping Passive Investments Truly Passive 36:00 - Values-Driven Investing and Long-Term Impact   Connect with Spencer! Website: https://www.madisoninvesting.com/ LinkedIn: https://www.linkedin.com/in/shilligoss/   Be the Boss of Your Own Money and Own Your Future. Connect with us and Discover Investment Strategies Designed to make a Difference. Website: https://moneywithmission.com Linkedin: https://www.linkedin.com/in/moneywithmission   Key Quotes: "Competence creates confidence. The more you learn, the more confident you become in making big decisions." - Spencer Hilligoss   "Diversification isn't just smart—it's essential. A single income stream can leave you in hot water faster than you realize." - Spencer Hilligoss

In this episode of the Know Your Why Podcast, host Dr. Jason Balara interviews Spencer Hilligoss, a seasoned passive investor who transitioned from a thriving tech career to a purpose-driven life centered on real estate investing and financial literacy. Spencer shares how he designed a lifestyle that prioritizes family, financial freedom, and long-term impact. He discusses the value of goal setting, the sacrifices required to achieve big dreams, and the importance of instilling financial literacy in future generations. Through candid insights, Spencer highlights the rewards and challenges of entrepreneurship and the transformative power of investing in real estate. Key Highlights - Spencer's pivot from tech to passive investing demonstrates the power of aligning goals with values. - Sacrifices and disciplined planning are essential for building a lifestyle by design. - Financial literacy plays a critical role in shaping opportunities for future generations. - Real estate investing offers a pathway to passive income and work-life balance. - Prioritizing family and experiences, such as traveling abroad, creates a fulfilling lifestyle. - Community, relationships, and continuous learning are integral to personal and professional growth. Spencer's journey showcases the possibilities that arise from pursuing financial freedom with intention and resilience. His focus on family, goal setting, and empowering others through financial literacy offers actionable lessons for anyone striving to create a life of purpose. Tune in to this inspiring episode of the Know Your Why Podcast to learn how to build a lifestyle by design and leave a lasting legacy. Get in touch with Spencer: https://www.madisoninvesting.com/ https://www.linkedin.com/in/shilligoss/ If you want to know more about Dr. Jason Balara and the Know your Why Podcast: ⁠⁠https://linktr.ee/jasonbalara⁠⁠   Audio Track: Back To The Wood by Audionautix is licensed under a Creative Commons Attribution 4.0 license.⁠⁠ https://creativecommons.org/licenses/⁠⁠ Artist:⁠⁠ http://audionautix.com/

Spencer Hilligoss is a passive investor who has deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, Spencer retired from a 13-year career in Silicon Valley tech companies in order to give full focus to serving fellow investors in Madison Investing - a club where passive investors gain access to the same types of niche investment opportunities where Spencer deploys his own money - including cash flowing assets like self-storage, rentals, multifamily, ATMs. Spencer lives with his family in Alameda, California - is a proud father of two, graduate of the University of Colorado and member of the Forbes Business Council. What You Will Learn: Who is Spencer Hilligoss? What inspired Spencer to transition from a tech career to real estate investing? How did growing up in a broker household influence Spencer's career choices? What key factors led Spencer to leave a high-stress tech job for passive investing? How has your work-life balance changed since transitioning to real estate investing? Why is it important to treat real estate as a business rather than just a job? What are the main differences between entrepreneurial and transactional mindsets in investing? Why did he believe passive investing is a viable strategy for achieving financial goals? Spencer explains how you utilized personal income and HELOCs to fund your investments. How important has education been in your journey as a real estate investor? What are the strategies he can recommend for balancing learning and taking action in investing? Spencer shares the key lesson he learned about why businesses fail. What are some key tax implications that passive investors should be aware of? What strategies can investors use to achieve tax efficiency in their investments? Why is it important for investors to understand tax rules to minimize their tax burdens? What are the key benefits of working with a tax advisor for proactive tax planning? How do tax filing and tax advisory differ in terms of their focus and purposes? What strategies can real estate investors use to enhance their monthly cash flow? What common challenges do individuals face after exiting a business, particularly regarding reinvestment? Spencer shares how everyone can contact him. Additional Resources from Kyle Reedstrom: Website: http://www.madisoninvesting.com/ Email: spencer@madisoninvesting.com Phone: 1-4152900328 LinkedIn: https://www.linkedin.com/in/shilligoss/ Facebook: https://www.facebook.com/madisoninvesting Attention Investors and Agents Are you looking to grow your business? Need to connect with aggressive like-minded people like yourself? We have all the right tools, knowledge, and coaching to positively effect your bottom line. Visit:http://globalinvestoragent.com/join-gia-team to see what we can offer and to schedule your FREE consultation! Our NEW book is out...order yours NOW!   Global Investor Agent: How Do You Thrive Not Just Survive in a Market Shift? Get your copy here: https://amzn.to/3SV0khX HEY! You should be in class this coming Monday (MNL). It's Free and packed with actions you should take now! Here's the link to register: https://us02web.zoom.us/webinar/register/WN_sNMjT-5DTIakCFO2ronDCg

In today's episode,  host Victoria Collier talks with Spencer Hilligoss, investor in Madison Investing, about what to do after selling your law firm. Spencer shares valuable insights on transforming your sale proceeds into a lasting income stream, exploring how passive investments can open new opportunities for financial freedom. They dive into lessons from Spencer's transition from tech to investment and discuss strategies law firm owners can use to align their money with their life goals—without getting bogged down in active management. Key Takeaways 1.⁠ ⁠Goal Setting Is Essential – Establishing specific, long-term financial goals creates a strong foundation for successful post-sale investing. 2.⁠ ⁠Passive Income Opportunities – Real estate and alternative investments can offer reliable, passive income with the right planning and partnerships. 3.⁠ ⁠Don't Reinvest Without Reflection – The initial exit strategy is just the first step; carefully selecting how to allocate your proceeds can enhance security and satisfaction over the long term. About Our Guest Spencer Hilligoss is a passive investor who has deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, Spencer retired from a 13-year career in Silicon Valley tech companies in order to give full focus to serving fellow investors in Madison Investing - a club where passive investors gain access to the same types of alternative investment opportunities where Spencer deploys his own capital. Spencer lives with his family in Alameda, California - is a proud father of two, graduate of the University of Colorado and member of the Forbes Business Council. For more about Spencer and Madison Investing, visit madisoninvesting.com.   We want to hear from you! You can leave us a rating and review in Apple Podcasts. Click here and then scroll down the page to the rating and review section. You can also leave us a rating in Spotify by clicking here. Connect with Victoria Collier https://quidproquolaw.com/ Private Facebook Group https://www.facebook.com/groups/1284225722042602 LinkedIn https://www.linkedin.com/company/victoria-collier-coaching/        

Spencer Raises MiLLION$$$ New Livestream guest- Spencer Hilligoss I'm happy to have Spencer join me on a live broadcast. He's been busy doing private real estate deals and he's raised millions of dollars via syndication deals. Tune in and as we'll be discussing how his business operates and what it's like to attract and accept investor money. If you think you're just gonna ‘get investors' this episode is for you as we'll be discussing all the realities of being responsible for other people's money. This is a ‘must see event' for people who need to raise cash to get deals done. Find spencer online at Madison Investing here: https://www.madisoninvesting.com/ Be sure to join my email list so you never miss any new videos at https://www.DavidCBarnettList.com

Spencer Hilligoss was born and raised in Redwood City, California. He loved to be around people who liked to play punk rock as a kid. He decided to play bass guitar when his friend told him he bought a bass guitar and gave it to him. His friend said “hey you want to play in […]

In this episode, we have Spencer Hilligoss, the dynamic CEO of Madison Investing. Spencer's journey is nothing short of remarkable, transitioning from a successful career in the corporate world, where he led operations and sales teams at five high-growth Fintech companies, to becoming a full-time investor and entrepreneur. Spencer founded Madison Investing with a clear mission: to help busy professionals secure their most valuable asset—time—by offering them access to carefully curated, cash-flowing real estate deals.  During our conversation, Spencer shared his insights into breaking free from the "golden handcuffs" of corporate life just months before the pandemic hit in 2019. He discussed the mindset shifts required to make such a bold move and how his focus on serving his investment group has led to Madison Investing's tremendous growth. Spencer's commitment to helping others achieve financial freedom is evident in every aspect of his business, and his story serves as a powerful example of what is possible when you combine passion with purpose. In this episode, we talked about: Spencer's journey and expertise in the world of investing His strategic investment thesis, philosophy and business approach Insights on current market trends and associated risks Identifying and capitalizing on emerging market opportunities Click here to read more: https://pantheoninvest.com/episode136

Welcome back to another episode of the Richer Geek podcast. Today, we have Spencer Hilligoss, CEO of Madison Investing - a real estate investment club with bespoke, curated real estate deals. Spencer founded Madison Investing with a singular mission — to help busy, successful professionals invest passively, secure their most valuable asset of all time. In this episode we're discussing... His background: Spencer's transition from tech to real estate was fueled by a quest for autonomy. Importance of passive investment: Strategic planning crucial for attaining financial independence. Building wealth and freedom: Investing in passive income streams allows individuals to build a life they don't need a vacation from. Time compression and goal Setting: Long-term goals require efficient planning to accelerate wealth accumulation. Madison Investing and investment opportunities: Madison offers multifamily investments for limited partners. Core principles of investing: Aligning investment goals with personal objectives is paramount. Spencer advises revisiting core principles to define capital goals. Connecting with Spencer Hilligoss: To learn more about Madison Investing and explore investment opportunities, visit madisoninvesting.com and request an invitation.   Resources from Spencer Madison Investing | LinkedIn   Resources from Mike and Nichole Gateway Private Equity Group | REI Words | Nic's guide

Spencer Hilligoss was an operations and sales junkie working for 5 high growth Fintech companies in 13 years. He decided to break free from the golden handcuffs, quit his job, and work on growing his investment group, Madison Investing. Since then, he has become a full-time investor by partnering with in-market, vetted operators and has $2.3 billion in acquisitions with over 20,000 units. He is also a registered member of FINRA and a member of the Forbes Real Estate Council.FOLLOW SPENCER

In this Topical Tuesday's episode, I spoke with Spencer Hilligoss who is the CEO and Co-Founder of Madison Investing where he currently leads business development and investor relations. He's also an active syndicator, investor, and speaker, and before starting Madison Investing, he was formerly a technology executive with a 13-year track record building high-performing teams. Be sure to tune in if you're interested in learning about: How his recent extended stay abroad helped him both personally and professionally The biggest challenges and adjustments that he's faced in his business during the past 2 years What types of opportunities that he's excited to pursue in 2024 Ideas for investors to consider in constructing a passive portfolio in 2024 and beyond To your success, Tyler Lyons Resources mentioned in the episode: Spencer Hilligoss Website Interested in investing with Asym Capital? Check out our webinar.   Please note that investing in private placement securities entails a high degree of risk, including illiquidity of the investment and loss of principal. Please refer to the subscription agreement for a discussion of risk factors. Tired of scrambling for capital?  Check out our new FREE webinar -  How to Ensure You Never Scramble for Capital Again (The 3 Capital-Raising Secrets). Click Here to register.   CFC Podcast Facebook Group

Today's guest is Spencer Hilligoss.   Spencer Hilligoss is a passive investor who deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, Spencer retired from a 13-year tech career to fully focus on Madison Investing, his passive investing club.   Show summary: In this podcast episode, Spencer shares his personal journey from working in technology companies to retiring in 2019 to focus on his passive investing club. He emphasizes the need for clarity and vigilance in investing, advising investors to thoroughly vet teams and operators before investing. Spencer also provides advice on how to communicate with and motivate investors during challenging times, using two investor profiles as examples.   -------------------------------------------------------------- Intro (00:00:00) Spencer's background and retirement (00:01:26) Clarity and vigilance in passive investing (00:04:25) Twists and Turns in Investing Journey (00:14:05) Positioning for the Next 12 to 24 Months (00:16:10) Investing at the Wrong Time (00:19:19) Motivating Investors to Invest (00:20:06) Understanding Investor's Circumstances (00:20:41) Educating Towards Future State (00:21:16) -------------------------------------------------------------- Connect with Spencer:  Linkedin: https://www.linkedin.com/in/shilligoss/   Web: www.madisoninvesting.com   Connect with Sam: I love helping others place money outside of traditional investments that both diversify a strategy and provide solid predictable returns.     Facebook: https://www.facebook.com/HowtoscaleCRE/ LinkedIn: https://www.linkedin.com/in/samwilsonhowtoscalecre/ Email me → sam@brickeninvestmentgroup.com   SUBSCRIBE and LEAVE A RATING. Listen to How To Scale Commercial Real Estate Investing with Sam Wilson Apple Podcasts: https://podcasts.apple.com/us/podcast/how-to-scale-commercial-real-estate/id1539979234 Spotify: https://open.spotify.com/show/4m0NWYzSvznEIjRBFtCgEL?si=e10d8e039b99475f -------------------------------------------------------------- Want to read the full show notes of the episode? Check it out below: Spencer Hilligoss (00:00:00) - The goal setting process, like if there were to be. What is the most active part of being a passive investor? Because there are active parts. Right? And this is the misnomer. I think it is sitting down and just gut checking with the financials. What is your true north? Or I'll take out the platitude like what is your financial target you're aiming for? Just like if you're inside of a business, if you're going to use to work in the corporate world, anyone who's in a W2 world, if you manage a profit and loss, if you manage a financial plan, you got to go and sit there and say, hey, last year we thought the target like a win would be that dollar amount. Well, this year is looking a little different. So let's revise like what are where is our bearing here.   Sam Wilson (00:00:44) - Welcome to the how to scale commercial real estate show. Whether you are an active or passive investor. We'll teach you how to scale your real estate investing business into something big.   Sam Wilson (00:00:58) - Spencer. Helios is a passive investor who has deployed seven figures of his own capital into passive investments in the past six years. In 2019, he retired from a 13 year tech career to fully focus on Madison investing his passive investing club. If you don't know, Spencer also came back on the show. Gosh, what was that? Spencer episode 274 I think. So sometime early 2021. We've done about 600 episodes since the last time you were on the show, so it's a pleasure to have you back on the show today.   Spencer Hilligoss (00:01:26) - Yeah. Wow, that's a fast two years. Sam. Thank you for having me back on. Absolutely.   Sam Wilson (00:01:32) - The pleasure's mine, and it is a fast two years. Spencer, before we get into the heart of the show, though, there are three questions I ask every guest who comes on the show. You have answered these previously, but we're going to have you answer them again in 90s or less. Can you tell me where did you start? Where are you now and how did you get there?   Spencer Hilligoss (00:01:48) - Oh yeah man, there's still fun questions.   Spencer Hilligoss (00:01:50) - Now I'm probably going to get a different lens on it though, as always, as life evolves. So where I am now actually, let's go back. I started growing up as a punk rock and metal kid playing in bands. My dad was a real estate broker for 30 years. I was working for him as a kid, which is why I ran screaming into technology companies. I live in Silicon Valley in the Bay area, California. I have, you know, grown up for 13 years professionally building and leading large operations and sales groups for fintech companies, financial tech companies. As you mentioned, Sam, I retired in 2019, five months before Covid, and that was not part of the plan, but I would say grateful now more than ever to be leading Madison Investing, which is our passive investing club, as you mentioned up front, where we help other folks walk the same path that we have. You know, I know that right before we hit record, I was sharing a quick story about highlight of the year so far.   Spencer Hilligoss (00:02:45) - We just got back from spending six weeks in Portugal as a whole family, that type of thing, that type of lifestyle decoupling from a geography, taking our kids who are six and nine and Jennifer and I are both living and working abroad with that flexibility. That's what's enabled by passive investing done right. And of course, it's not always like turnkey. Across the the journey. There's a lot of twists and turns. You got to pull out your figurative machete and hack through the the forest, as it were, and find clarity along the way. But hopefully I didn't exceed my 90s on that one.   Sam Wilson (00:03:17) - No, I think shoot, if you weren't, if you were, if you were over 90s, it was worth listening to. So I appreciate you giving us that. That recap yet again and again. If you didn't hear Spencer's first show, go back and check that one out, because I know we're going to cover some very different things. Maybe then what we covered there on that show. You know, I think one of the things and I'm not going to hopefully offend you here by saying this, but I feel like everyone has these grandiose ideas of what passive investing is.   Sam Wilson (00:03:44) - So they're like, oh, man, you know, we're going to be a passive investor and we're going to just cash checks all day long, and it's going to be amazing. But I think the experience is wildly different. I certainly know it has been for me, as I look at all the different passive investments I have, I go, okay, you know, there's some there doing well, some that are doing but not doing well, and then there's some that are performing very poorly. And I look at that and I go, gosh, that's that's it's kind of painful in some respects to look across all of them go, not everything's doing great. What would you say a current investors outlook and kind of mood should be about passive investing right now, because it doesn't always necessarily translate into six weeks in Portugal.   Spencer Hilligoss (00:04:25) - Oh my gosh, what a killer question to open with and for people listening. Sam didn't prep me for that question ahead of time. That's just a hell of a good question. Clarity and vigilance.   Spencer Hilligoss (00:04:36) - You know, I think clarity, first and foremost, it comes down to goals. And everyone out there hopefully is starting from that point. As a quick refresher, Sam, clarity to me means sitting down 2016. I'm working full time, deep into my career and climbing that ladder, making great W-2 income. Jennifer Morimoto, who is my my spouse, my wife, and my co-founder and, you know, co-pilot in life, you know, mother of our kids across the board. We work together in life and work. And we sat down and took a whole weekend to literally sit down and say while working full time, both of us in separate careers, what is the dollar amount per month that we could that we need to hit? Full passive. To cover our needs. And that was a scary exercise, man. That was a scary exercise. And it's something that I think I don't go into lightly, because that weekend had tears that we can had reconciliation and had laughter, and we had to get a sitter to get the kids out of the house just to do it right.   Spencer Hilligoss (00:05:37) - But that's where it started. We set that goal with a 15 year time horizon to remove all excuses. And so by clarity, what I mean is it sounds so clean and simple to say, I'm going to hit 8000 bucks in passive income, which I believe at that time was our monthly income, passive income target. And, you know, I'll qualify it by saying everyone has different expectations in life. Like, we don't want to we don't I don't need a jet. I'm a pretty simple dude. Like I got some guitars. I like plucking a guitar, but I don't need a boat and no judgments on those who want more. But that was our goal back then, and we hit that goal in the last about year and a half, two years ago, we hit that goal in full passive. And we're we're so proud of hitting that. That was hard. But we said 15 years on, the original goal came back shortly after that exercise in 2016 and said, well, that's just too long.   Spencer Hilligoss (00:06:29) - You know, you and I were chatting about our kids right before we hit record today, Sam. And I'll say that like, we wanted to catch some of the magic years, as it were, spending time with our boys while they were still pretty young, and being able to have that type of lifestyle where we could spend more time. And that is what got that clarity for me. So thanks for listening to that context. I just think it's so key for people to sit there instead of saying, man, look at that great looking Facebook paid ad that presents this two x equity multiple, right on a killer looking deal, a beautiful marketing deck. And you're like, that's my ticket to financial freedom. Be like, slow down, get clear. Get clear on why you're looking at this thing. And then don't worry about asset class yet. Come back to it later. Those are the lessons I wish I could impart on myself earlier on. One other thing I'll say is like 2023 for sure has presented some challenges, right? And you hit it earlier.   Spencer Hilligoss (00:07:19) - I'd say that things like understanding the basics of what is the purpose of this one investment, what's the goal for the money? Is it a growth play? If a person is working, like talk to one of our investors in our club who's actively investing with us, has for years, and he says, well, in 5 to 7 years I want to get X dollar amount. By fully passive, you know, 5 or 7 years out. And that's a very thoughtful, responsible goal for that investor. That's a cash flow investor who is making killer W-2 income at a day job, doesn't need it now, wants to have it later so they can still potentially afford to go and invest for growth. They don't need the cash flow now, but if that same investor puts a bunch of money, puts 100 K into a deal, and they have a pot distribution right now. And they're going to get great growth on the back end of that thing. But they don't have a distribution coming in now for a monthly income.   Spencer Hilligoss (00:08:13) - That's a mismatch. So I'll take a pause there. But just wanted to kind of cover at least the vigilance on the clarity.   Sam Wilson (00:08:18) - No I think that's great. I think that's really, really great. You touched on the term goal for the money, which I think is is a it's a powerful. It's a powerful idea because even though we have financial planners and we have people that lay out again all the, hey, you know, this is what you're going to have if you invest. And of course, we've all been through that drill with with our stockbrokers and everybody else where they show, you know, projected where it's going and what it's going to do. I think a lot of times we missed that same exercise. At least I have personally in my own and passive investments around the country in commercial real estate because it's like, oh, that's cool. Like you said, that's a cool deal, I like that. Why not? Let's throw 50 grand or 100 grand at it and see where it goes.   Sam Wilson (00:08:59) - Like, this is going to be fun. But then you look at it and you're like, wait, did that actually line up with what I wanted to do in 5 or 7 years? Because that requires discipline and time. It requires those weekends that you're talking about going, okay, you know, getting a spreadsheet of everything, or maybe it's even more complex than that. But if everything where it's going, what you're expected, payouts are getting them. I mean, that's hard work. I've got a sheet like that. It's hard work. Comparing zero eight. We got a distribution this month. Did it line up with what was pro forma? Which of these are doing what they say they're going to do. And that's that's just it becomes its own kind of animal that. I don't know. Speak to us on that front if you can.   Spencer Hilligoss (00:09:37) - Oh, man, I love this topic. I would say you're nailing it. And by the way, I'm so guilty of the same thing. You know, you see a great looking deal.   Spencer Hilligoss (00:09:45) - Or maybe you just love the team, like, like, oh, I love that operator. They have such a tight operation. Their reporting is killer. Their financial reporting is transparent. They have experience. They've got repeatable process. They've got the exits, full cycle deals, all the works. Right. And I'm like, oh cool, let's drop money. And then I'm like, well, that wasn't so much of a cash flow play. I mean, it reminds me of the very first property we bought is a duplex sitting in 45 minutes from our house, where I'm sitting right now in Vallejo, California, and that thing costs 430 grand. And that's a California property for you. We bought it years ago, cost us six figures. It's down payment and a cash flow is $200 a month. That is not a cash flow win by any measure. That's a quick way to use the player capital, right? But I bring that up as one example of like where we started to where we are now.   Spencer Hilligoss (00:10:35) - And I would say now actually we're going through a refresh of this very exercise. And it's related, I think, to what you brought up a moment ago, Sam, you know, the goal setting process, like if there were to be what is the most active part of being a passive investor? Because there are active parts, right? And this is the misnomer. I think it is sitting down and just gut checking with the financials. What is your true north? Or I'll take out the platitude like what is your financial target you're aiming for? Just like if you're inside of a business, if you're what I used to work in the corporate world, anyone who's in a W2 world, if you manage a profit and loss, if you manage a financial plan, you got to go and sit there and say, hey, last year we thought the target like a win would be that dollar amount. Well, this year is looking a little different. So let's revise like what are where is our bearing here.   Spencer Hilligoss (00:11:28) - And so we're going through that now to say well you got to track it in a spreadsheet. You've got to sit down and say what's the monthly income expected from this. Are we up? Are we down. How much do we need? Are we off track? Do we need to reserve some capital because our family is going to face some some headwinds or maybe tailwinds. Maybe there's good news coming in. You know, just got some unexpected great news on, like, an exit from a deal that is like a mobile home park refinance that's coming in. And I was like, wow, that's the first, I think, capital event that's occurred in 2023 personally. So like that was that was quite unexpected, you know. So I'm like, woo, that's great to see. And we'll see a lot more of that hopefully between 20 and 24 but most likely 2025. So it's tracking and knowing where you're at on that figurative map and sitting down and saying, let's put some financial assumptions behind it, like, what are we going to get out of this deal? Exits, cash flow.   Spencer Hilligoss (00:12:18) - What does take work? It takes some work, you know.   Sam Wilson (00:12:22) - It does take work. And I think it takes work. And it also, like you said, figuring out, you know, what your true north is in this and then and then picking the right opportunities that kind of make up that matrix of deals that you should or should not be investing in. So I think that's just knowing just knowing what it is you're looking for. And again, not being guilty of following my footsteps and just going, oh that's cool. Like I love the sponsor. I love the deal. I mean, why shouldn't we do it? Like, because maybe it doesn't fit the plan. I was having a call with a with a. Friend slash business guy here in Memphis yesterday. And he goes, he goes, Sam. He goes. My answer should be to, you know, he goes, it's no. Because for these two reasons he goes, but yet I just can't help but talk to you about it because this is really fascinating.   Sam Wilson (00:13:11) - So let's keep going. And I'm like, Bill, you know exactly what your answer should be. And I appreciated that. It was it was just a funny response. He's like, my answer should be no because I don't know anything about it and it doesn't fit my box, but I want to hear more like so anyway, we all.   Spencer Hilligoss (00:13:27) - Do it.   Sam Wilson (00:13:27) - We all do it, but we all do it. Yeah, we all do it. Not falling into that trap. So that's really cool. We've talked a little bit about defining temperament in our in our investments, being a tempered investor if you will, finding out goals for the money currently. Tell me tell me a little bit about this. Like what you said that there's two things. One, you said you've experienced some twists and turns in your investing journey. I think you said since 2019. So maybe if you can give us a couple examples of what those twists and turns are, and then tell us how you guys are positioning yourselves to really take advantage of the next 12 to 24 months.   Spencer Hilligoss (00:14:05) - Yeah. Happy to. So. Twists and turns first. Abbreviated version. I can define this in three quick phases. This is not how it felt. Real time. Of course. Life has crazy chapters. You don't know where you're at on the map sometimes until you come out the other side of it, right? So phase one still working full time. This is back in about 2016. We bought that rental that pricey for 30 K rental. I just told you about California and we're like, wow, we're going to run out of money real quick this way. Not in line with our cash flow goals. We then got more comfortable to really took our time and looked at more rentals. Still didn't hadn't quite moved on beyond that rental phase. And rentals are fine. They're a great wealth builder, but. They are semi passive at best. Right and I will happy to debate anyone on that topic. Anyone who's owned rentals can attest to that, property manager or not. They're semi passive. So we got up to five long distance rentals and they were out in Kansas City, Kansas City, Missouri and 60 K average purchase price 250 bucks a month.   Spencer Hilligoss (00:15:08) - Average cash flow. That's a heck of a lot better economics than the first one. Those were maybe, at best, C-minus neighborhood. Um, you don't really learn what that means till you do it.   Sam Wilson (00:15:21) - Right?   Spencer Hilligoss (00:15:22) - And, you know, you get you get it. So we learned that way in terms of overhead, you know. That was more work than we expected it to be. Even with property managers, the economics got a little bit kicked every year because the tenants would beat up the place a little bit, and then we had turnover costs, etcetera. So we sold those properties, and then eventually we started investing as passive investors purely as LPs and some multifamily deals. And we're talking in Alabama and in Texas and a few other great markets, eventually multifamily self-storage. And those twists and turns initially, I would say were super important. You know, like a little expensive. You pay tuition with experience and scars. You also pay it with physical capital. And I would just say that those those were not, in hindsight, ideal if you're trying to maximize return, but they were necessary for us to get to where we are now.   Spencer Hilligoss (00:16:10) - And so I look at those also, once we started investing as LPs, got some killer exits from those. This is around the 2018, 20, 2019. And then we're like, well. There's so many colleagues and so many folks in my network that were saying, Spencer, like, we don't want to fly out to these properties like, you're, you know, this stuff. They're saying this to me like, you know, this stuff, you're flying out of these assets, you're walking them. You want you know, how to underwrite them. All this stuff. And I'd work so hard to get there to do that. Why don't you? What? You help us, you know? And so then we started medicine investing around that time. And it's just the club dynamic of being an educator and a resource for folks to see who who are these teams we invest in. But that doesn't necessarily mean it's always clear. It doesn't mean it's always easy. You know, like like taking the time to get to know partners and operators is it is art and science.   Spencer Hilligoss (00:17:05) - You know, it's, you know, vetting teams and humans is always going to be that way. And so I would say those were some of the whiz bang version of like the twists and turns along the way that brought us to where we are now. Um, I'd say that looking forward to your second question, though, right now is a unique time. You know, I think before this journey over the past seven years, you know, coming out of a tech career, Sam, like, I wouldn't have known how to take in the feedback and the mentorship that we hear, the wisdom that we hear when it comes to when's a great time to invest? Like when do the wealthy people, the wealthiest of the wealthy, the Warren Buffett's like, when do they make the biggest returns? When do they maximize their wealth building? And I wouldn't have understood. Like, you got to go out there and take informed risks during challenging volatility times, during economic headwind times. And that is why right now we're walking into a killer buying opportunity.   Spencer Hilligoss (00:18:02) - We're walking into a killer investing landscape. And it's it's the tough part for every investor is to look through the noise. There's a ton of very real noise occurring right now in the headlines, of course, globally and nationally. But I would say take what you need from the news, but then look past. It has best you can, you know. And so we see opportunities to buy and invest at the asset classes that we love. Multifamily large apartment communities largely in the Sunbelt. With some of the Rockies still love self-storage. We've been focusing on self-storage now since 2019 as a sister asset class, along with multifamily and a couple of other niche non-real estate asset classes. But I would say that that's really what it's about is just being vigilant about not pouncing on a deal is because it looks like it's great from a team that we know you got to go do it deeper. And clearly I have to say this as well. One last thing is just like the interest rate has to be the debt, the loan, the loan structure has to make sense in the current climate.   Spencer Hilligoss (00:19:04) - It has to be either in a suitable loan. You know, there's a lot of that going on on the few deals there are, or it has to be some kind of unique situation where the seller is distressed and you're getting a very significant discount, but tough to find those.   Sam Wilson (00:19:19) - It really is. But those are those are things. And I like your, your you seem to be a more patient investor maybe than what some of the, some of the, you know, fury that's been out there in the last couple of years, you seem to take more time in what it is that you're investing in. And I think you're right here in the next couple of years, we're going to see we're going to see some great opportunities come down the pipe. But I guess here's a question for you. Most investors, the book, Howard Marks wrote the book, Mastering the Market Cycle. And in that he basically says that historically, investors invest at the completely wrong time. Like if you just take the data and you overlay it with the economic profile, he goes, they're always investing at the top and selling at the bottom.   Sam Wilson (00:20:06) - He goes just right the way they do it. So how do you in the times of how do you I mean, I'll get to my question, but how do you communicate to your investors and then motivate them to invest at the times when it's like when everybody else is out yelling, run! You know, there's blood on the street, everybody's going to die and you're going to go, hey, man, you know, actually, right now is the perfect time to buy this distressed asset. You communicate that in such a way that it then compels your investors to invest.   Spencer Hilligoss (00:20:41) - Yeah. Gosh, that's a fun topic, man. I love the reference for the Marx book. I think understanding the posture as like as a passive investor myself, you know, as a passive investor yourself as well, it comes down to understanding fundamentally that like motivation to invest in motivation to act is is probably the incorrect way to look at it. It's really like, does a person understand squarely where they are? If you're trying to educate like they understand, this is probably going to lead back to a goals comment.   Spencer Hilligoss (00:21:16) - But I would say that it starts with just holding up the figurative mirror and saying, here's where I'm at. You know, here's an investor's circumstances. And if they are comfortable where they are, you're really not going be able to prompt action and you don't want to. I'm not interested in trying to compel someone to go and invest in something that is not fit for their portfolio or fit for their their goals. I think really what it comes down to is helping them understand the future state, understanding the future state. What I mean by that is where is the life they want to be, right? Like in three years, five years, seven years, whatever that time horizon could be. And if that means, you know, let's take two profiles. I'll just keep them anonymous and kind of abstracted here. But like profile one most common one, I would say a fellow investors that we work and invest alongside with W-2 employees, at least one significant W-2 income coming into the household likely to if they're in California.   Spencer Hilligoss (00:22:10) - Absolutely to because it's just too expensive here to have one usually. So they're sitting there going, I don't necessarily need to quit my job right now. That profile of dual income with kids, California or West Coast pricing market, they're thinking in maybe five, seven, maybe ten years. Then we want to have some optionality, because perhaps they're aging out of the tech career because ageism is a thing, and eventually they want to have some kind of safety net. So they have to think about these goals. And so educating toward that future state absolutely is the most important thing. And then connecting the dots backwards from that, like reverse engineering where do they want to be. Similarly, it's going to sound familiar, probably to where Jennifer and I were at, you know, years ago. It's like where we where were we when we started holding up that figurative mirror? Looking across, auditing our income sources, auditing our wealth, picture all that stuff, and then setting a real clear, crystal clear vision of like, well, where do we want to be? You know, what kind of lifestyle do we want to have? What kind of options do we want to have? That all applies for people who are working, and they have to work currently for their income profile.   Spencer Hilligoss (00:23:17) - Two high net worth folks, folks who, you know, maybe they exited a business that they built. Maybe they own a company actively, but they're taking more of a backseat while the next generation takes it over. You know, all that profile of so many different high net worth folks out there. But I would say that is more of a discussion of hedging downside risk in a discussion of capital preservation and understanding, like, yeah, I absolutely agree. It's a unique time when you're looking over there at the treasuries and you're saying, wow, that looks like a super safe 5%. Well, what percentage of their portfolio are they trying to allocate toward that? And also, is it really 5% that they want or are they looking at that 5% a little bit too myopically. Are they are they overanalyzing and just using that as their, their, their Uber excuse for analysis paralysis because they just don't want to go and do the mental work across the market right now to think, oh, there are excellent deals that can produce double, triple plus whatever you're getting on a treasury, you know.   Spencer Hilligoss (00:24:17) - So not getting probably getting a little too nerdy here probably for that one Sam. But that's a fun question.   Sam Wilson (00:24:22) - That's awesome Spencer, thank you for taking the time to break. Break that down. And a like I like the the the the phrase you said educating to that future state. And again I probably misused the words not motivate or compel. But it's one of those things. How do you get people off the fence. Yeah.   Sam Wilson (00:24:37) - Yeah yeah.   Sam Wilson (00:24:38) - And it's and it's and that's because again, we don't want people investing. And I've told people that I've told people before I said, no, this just isn't for you like this. This deal is not for you. So please don't invest. Yeah. You can just sense it. But, you know, I do think it is important, though, to see people when they're stuck in that analysis paralysis going, oh my gosh. Like I'm just going to sit here because everything looks so scary. And I think you've you've made some really valid points there on that that I won't rehash and kill it because you did.   Sam Wilson (00:25:04) - You did a great job really explaining that. So thank you again for taking the time here to come back on the show today. It's been an absolute pleasure to have you back on. If our listeners want to get in touch with you and learn more about you, what is the best way to do that?   Spencer Hilligoss (00:25:17) - Yeah. No thank you, Sam, this has been awesome to reconnect. So Madison Investing.com, that's our website and folks can find some educational content there. We put up there monthly. They can also set up time to chat with me. Happy to be a sounding board on their passive investing strategy.   Sam Wilson (00:25:31) - Fantastic. Madison Investing.com. We'll put that there in the show, notes. Spencer. Thank you again for taking the time to come on the show today.   Sam Wilson (00:25:38) - I do appreciate it.   Spencer Hilligoss (00:25:39) - Yeah. Thank you Sam, really great to see you.   Sam Wilson (00:25:41) - Hey, thanks for listening to the How to Scale Commercial Real Estate podcast. If you can do me a.   Sam Wilson (00:25:46) - Favor.   Sam Wilson (00:25:46) - And subscribe and leave us a review on Apple Podcasts, Spotify, Google Podcasts, whatever platform it is you use to listen.   Sam Wilson (00:25:54) - If you can do that for us, that would be a fantastic help to the show. It helps us both attract new listeners as well as rank higher on those directories. So appreciate you listening. Thanks so much and hope to catch you on the next episode.

Dreaming of making real estate investing your full-time job and getting rid of your 9-5 job? Then this episode is for you! Listen in as we dive into the pivotal decision of quitting a job for lucrative real estate investments in 'deal states' like Texas, Georgia, and North Carolina.Joining us today is one of the courageous individuals who made the leap—Spencer Hilligoss, CEO of Madison Investing. Spencer retired from his 13-year career in tech to travel the world while earning passive income through real estate. We unravel the ups and downs of career transitions and the evolving phases of real estate investing, from initial rental investments to the complexities of multifamily properties. We also share valuable insights on navigating the dynamic market, emphasizing the significance of due diligence and strategic analysis in the ever-changing landscape of investment opportunities. Tune in to discover key tips on vetting sponsors and potential partners and how to make informed decisions when investing passively in multifamily real estate. Whether you're seeking consistent cash flow or aiming to diversify your portfolio, we're here to help you align your goals with the right investment strategies, so join the conversation! EPISODE HIGHLIGHTS: 8:43 - Real estate investing phases and challenges 14:17 - Real estate investing strategies and market analysis24:57 - Evaluating potential real estate partners29:16 - Investing passively in multifamily real estateCome check out Madison Investing's website and schedule an appointment with Spencer: https://www.madisoninvesting.com/ --Breneman Capital: https://www.breneman.comInvestor List: https://www.breneman.com/investPassive RE Investor Guidebook: https://www.breneman.com/downloadsConnect with Drew: https://linktr.ee/drewbreneman

Is there a secret formula to success in passive investing?   In this insightful conversation, Spencer Hilligoss, a seasoned passive investor with a 7-figure track record, delves into the world of passive investing and how it enabled him to create the lifestyle he desired. Spencer stresses how choosing the right team and investing with the right people has been instrumental in his investment success. Moreover, he emphasizes placing people at the core of investment decisions and making ethical investments that genuinely enhance the community and create a positive social impact. Spencer highlights the significance of not just investing for profit, but also for the well-being and comfort of individuals.   Join him as he shares the keys to success in passive investing – the right team, the right path, and the right investments with a people-focused approach. Learn more about ALTERNATIVE BUSINESS and INVESTMENT STRATEGIES through QUATTRO CAPITAL!   LinkedIn: /TeamQuattroCapital Instagram: @TeamQuattroCapital Facebook: @TeamQuattroCapital Website: www.TheQuattroWay.com   TikTok:@realestaterunwaypod [00:00 - 09:10] Designing a Life You Want to Live Through Passive Investing Spencer talks about his family's decision to live in Portugal for two months, the lessons they learned, and how passive investing made this choice possible He and his wife went from having traditional careers to passive investing, emphasizing the goal of achieving financial freedom From investing in rental properties, they later move on to larger multifamily and self-storage deals for a more hands-off approach He runs an investing club with his wife which helps other passive investors reach the same level of achievement [09:11 - 17:10] Betting on the Jockey, Not the Horse Recognize the limitations of the "do it myself" mentality in real estate investing and be open to learning from others Spencer breaks down his five-part framework for evaluating investment opportunities He focuses on the “who” and the why working with a team that has a strong track record of success is crucial [17:11 - 19:46] People First, Profit Later It's more than just making money; it's also about the values that guide your choices as an investor or operator Managing a multifamily property that houses hundreds of residents brings a responsibility to ensure their well-being and living conditions   [19:47 - 32:37] Navigating Real Estate Now: Tips from The Professional Passive Investor Spencer discusses the role of market fundamentals in investment decisions, regardless of changing economic conditions Understand local demand in real estate, as it is a hyperlocal industry Evaluate markets based on their ability to attract employers and provide jobs for potential tenants Cash flow and basis are important when making investment decisions in the current real estate landscape [32:38 - 37:34] Focusing on Relationships That Matter Spencer prioritizes building relationships through active listening and having a long-term perspective He opens up about how he manages his work and personal life, being a dad, and what led him to make important changes in his life Quotes:   “2021 was a landmark year. You've got some teams that have these incredible exits, these amazing outcomes. You better believe I want to see a repeatable approach, a repeatable process.” - Spencer Hilligoss   “We are, in fact, capitalists, right? I mean, I get it, but it is possible to have profit and still do the right thing.” - Spencer Hilligoss   “It matters how you achieve those returns that are on that beautiful-looking investment summary, and part of that means providing a great living experience to folks along the way.”  - Spencer Hilligoss Connect with Spencer! Follow him on LinkedIn or check out MadisonInvesting.com. LEAVE A 5-STAR REVIEW + help someone who wants to explode their business growth by sharing this episode. Find out how Team Quattro can help you by visiting www.TheQuattroWay.com.   Real Estate Runway Podcast is all about alternative business and investment strategies to help you amplify life and maximize wealth! Click here to find out more about the host, Chad Sutton. Nectar: https://app.usenectar.com/quattro-capital Entity Keeper:  Join the EntityKeeper community today to simplify the way you manage your entities and org charts while reducing manual errors. Easily organize corporate data, visualize ownership structures, store unlimited documents, and manage important filing dates with one secure solution. Click here to start simplifying your entity management with EntityKeeper now!

Are you intrigued by the world of passive investing? San Francisco Bay Area native Spencer Hilligoss, a seasoned passive investor, shares his insightful journey from a demanding career in Silicon Valley to making a successful shift towards passive investing. Spencer's story is a testament to the strength of strategic planning and goal-setting; together with his wife, Jennifer Morimoto, they planned and achieved their five-year passive investing monthly income target, a huge feat in just six years! Don't miss out on this episode full of practical tips and inspiring takeaways to help you embark on or refine your passive investing strategy.Spencer Hilligoss is the CEO and Co-Founder of Madison Investing. He is an active syndicator, investor, and speaker. He currently leads business development and investor relations for Madison Investing.He is a former technology executive with a 13-year track record building high-performing teams across five companies (three of them software "unicorns"- valued at overvalued at over $1B). His last run in Silicon Valley was developing the Origination Team for LendingHome and leading their Professional Development group.​Spencer is a member of the 2023 Forbes Business Council and is a Registered Representative of Finalis Securities LLC, Member FINRA/SIPC.Connect with Spencer:Website: https://www.madisoninvesting.com/Connect with Jonny!Cattani Capital Group: https://cattanicapitalgroup.com/Invest with us: invest@cattanicapitalgroup.comLinkedIn: https://www.linkedin.com/in/jonathan-cattani-53159b179/Jonny's Instagram: https://www.instagram.com/jonnycattani/TikTok: https://www.tiktok.com/@jonnycattaniYouTube: https://www.youtube.com/channel/UCljEz4pq_paQ9keABhJzt0A

Are you looking for financial freedom through passive income? That sounds like a dream for most of us, and today we're going to learn the steps to start making that dream a reality, with Spencer Hilligoss, the CEO and co-founder, Madison InvestingThis episode of Deal Closers is hosted by Izach Porter, brought to you by WebsiteClosers.com, and is produced by Earfluence. Hosted on Acast. See acast.com/privacy for more information.

Do you wish you could quit your job and go fulltime as a real estate investor? Spencer Hilligoss breaks down the three steps he took to do exactly that. Welcome to Pillars of Wealth Creation, where we talk about building financial freedom with a special focus in business and Real Estate. Follow along as Todd Dexheimer interviews top entrepreneurs, investors, advisers and coaches. Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals. 3 Pillars 1. Multiple income streams 2. Leverage 3. Don't bite off more than you can chew Book: Essentialism by Greg McKeown You can connect with Spencer at www.madisoninvesting.com Interested in coaching? Schedule a call with Todd at www.coachwithdex.com Connect with Pillars Of Wealth Creation on Facebook: www.facebook.com/PillarsofWealthCreation/ Subscribe to our email list at www.pillarsofwealthcreation.com Subscribe to our YouTube channel: www.youtube.com/c/PillarsOfWealthCreation

Join us for an enriching podcast episode featuring Spencer Hilligoss, CEO and Co-Founder of Madison Investing, an accomplished syndicator, investor, and renowned speaker. Spencer draws from his extensive experience as a former technology executive, having built high-performing teams across multiple companies, including software "unicorns" valued at over $1 billion. In this engaging conversation, Spencer shares invaluable insights on how to construct your own financial moat, ensuring your financial security and growth. He delves into strategies for wealth preservation, syndication, and investor relations, drawing from his membership in the 2023 Forbes Business Council and his role as a Registered Representative of Finalis Securities LLC. Tune in to discover the keys to building financial resilience and success with Spencer Hilligoss as your expert guide. HIGHLIGHTS FROM THE EPISODE 01:44 - Spencer's journey into real estate 05:26 - Active vs passive investing 11:00 - Critical skills for building a business 15:00 - Importance of a financial moat 20:50 - Real estate syndication 25:07 - Contact Spencer CONNECT WITH THE GUEST Website: https://www.madisoninvesting.com/                  CONNECT WITH THE HOST Website- https://upstreaminvestor.com/ Facebook- https://www.facebook.com/TwoSmartAssets/ Instagram- https://www.instagram.com/upstreaminvestor/ Twitter- https://twitter.com/twosmartassets LinkedIn- https://www.linkedin.com/company/two-smart-assets/ ----------------------------------------------------------------------------------------------------------------------- Listen, like, subscribe, and comment!

To access a FREE collection of resources, go to www.TheMaverickVault.com   Whether you're an experienced investor or just beginning to dip your toes into the world of finance, this episode is filled with insights that will assist you in comprehending and navigating the path of a passive investor. Join us, with our guest Spencer Hilligoss, to explore this topic in-depth and uncover the avenues towards achieving success as a passive investor.     Key Takeaways From This Episode A transformative journey of a real estate investor  The importance of active investing and partnerships in real estate  Tips on choosing the right partners and deals for successful investments How effective communication can enhance investor relationship Why you should navigate opportunities and market volatility with a grounded mindset     References/Links Mentioned YouTube Essentialism by Greg McKeown | Kindle, Paperback, and Hardcover Ender's Game by Orson Scott Card | Paperback, Mass Market Paperback, and Hardcover     About Spencer Hilligoss  Spencer Hilligoss is the CEO and co-founder of Madison Investing. He is an active syndicator, investor, and speaker. Spencer currently leads business development and investor relations for Madison Investing. He is a former technology executive with a 13-year track record building high-performing teams across five companies (three of them software "unicorns"- valued at overvalued at over $1B). His last run in Silicon Valley was developing the origination team for LendingHome and leading their Professional Development group. Spencer is a 2023 Forbes Business Council member and a Registered Representative of Finalis Securities LLC, Member FINRA/SIPC.     Connect with Spencer  Website: Madison Investing LinkedIn: Spencer Hilligoss   Are you a passive real estate investor seeking financial freedom? Almost daily, new headlines break on the latest financial market upset. Now is the time to get educated on how to strategically invest in commercial real estate for long-term financial freedom. Grab your copy of “How to Passively Invest in a Changing Economic Environment” Go to…www.MavericksInvest.com    Want to keep up to date on the commercial real estate market, trends, investing tips and know what Neil is buying right now? Connect with him at Legacy Impact Investors, and be sure to register for his newsletter.    Connect with Neil Timmins on LinkedIn. If there is a topic you want to know more about or a guest that you would like to see on the show, shoot Neil a message on LinkedIn.      About Neil Timmins Neil is a commercial real estate syndicator, published author, and podcast host.   Neil's entry point into the Real Estate industry came after a few short years in banking. Recognized by the Wall Street Journal as a Top 100 team and the #1 REMAX agent in Iowa by the age of 29, Neil had solidified his role as a force in the industry.   Having completed hundreds of Fix & Flips, Wholesales, Wholetails, Novations, and Owner-Financed deals, Neil longed to quit forfeiting time for dollars. After building a portfolio of single-family rentals to produce passive income, he found the strategy to be anything but passive.   Neil, however, didn't go looking for his first commercial deal, he actually stumbled into it. Since then, he has refined the process of analyzing and buying commercial properties that produce stellar cash flow.   Neil has been involved in over $300,000,000 in real estate transactions. While his holdings in commercial asset classes include apartments, offices, mobile home parks, and self-storage units, his passion is industrial property. Neil now has verticals in residential real estate, multiple commercial asset classes, brokerage, publishing, and this successful podcast.   Neil and his wife, Emily, are the proud parents of three active teenagers. Those who know Neil say he is a competitor by nature, whether for the biggest fish on a deep-sea fishing trip, the best ribs at a barbeque, or playing football back in his day at his alma mater, the University of Nebraska at Omaha as a Maverick. Neil is always up for travel, spending time on the water, and of course, meeting people interested in learning about and investing in commercial properties.   Click here to see video of the podcast. 

Madison Investing Blueprint: https://www.madisoninvesting.com/blueprintMadison Investing Website: https://www.madisoninvesting.com/Spencer Hilligoss LinkedIn: https://www.linkedin.com/in/shilligoss/Join our Facebook group for business owners to get help or help other business owners!The Business Ownership Group - Secrets to Scaling: https://www.facebook.com/groups/businessownershipsecretstoscalingLooking to scale your business? Get free gifts here to help you on your way: https://www.awarenessstrategies.com/

Spencer Hilligoss is CEO and Co-Founder of Madison Investing. He is an active syndicator, investor, and speaker. He currently leads business development and investor relations for Madison Investing. He is a former technology executive with a 13-year track record building high-performing teams across five companies (three of them, software "unicorns"- valued at over valued at over $1B). His last run in Silicon Valley was developing the Origination Team for LendingHome and leading their Professional Development group. Spencer is a member of the 2023 Forbes Business Council and is a Registered Representative of Finalis Securities LLC Member FINRA/SIPC.   Join our conversation with Spencer as she shares her inspiring journey, from starting her real estate career in college to establishing a well-regarded brokerage firm. She also shared the value of building trust with clients, offering tailored services to match each investor with the fitting properties, and continues to discuss the trials she faced during her venture. Spencer shares… Challenges in Real Estate Careers Trends in Philadelphia's Real Estate Market   Strategic Real Estate Investing The Importance of Education and Networking And so much more!   Find Spencer on:   Website - https://www.madisoninvesting.com/ LinkedIn - https://www.linkedin.com/in/shilligoss/   Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds and really helps our show grow, which allows us to bring on even better guests for you! Thank you in advance!

Follow Shawn and Mike on Instagram! Shawn: @shawn_dimartile   Mike: @investormikedotcom   Spencer Hilligoss is a passive investor who has deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, Spencer retired from a 13-year career in Silicon Valley tech companies in order to give full focus to serving fellow investors in Madison Investing - a club where passive investors gain access to the same types of niche investment opportunities where Spencer deploys his own money - including cash flowing assets like self-storage, multifamily apartments and ATMs. Spencer lives with his family in Alameda, California - is a proud father of two, graduate of the University of Colorado and member of the Forbes 2023 Business Council.  Join us as Spencer shares how he and his wife, Jennifer founded an investing group and has been involved in over 60 deals in multifamily and storage properties. Despite reaching their financial goals, they continue to build their real estate portfolio and are focused on striking a balance between work and family life. Don't miss out on the valuable insights and takeaways from this episode!    Connect with Spencer: Website: www.madisoninvesting.com LinkedIn (primary): https://www.linkedin.com/in/shilligoss/ Twitter: https://twitter.com/SpenceHilligoss   Interested in being a guest? Visit our website www.takeoffcapital.co/podcasts/ and click the "Be a Guest Now" button to apply.  

If you want to live a life of happiness and achieve your long-term financial goals, you'll love this episode! So, hop into this interesting discussion with Spencer Hilligoss, where he delves into the realm of vetted real estate and explains why it's a viable avenue for earning passive income.   Topics on Today's Episode Exceptional advantages of passive investing in the real estate  The power of mentorship and strategies to effectively leverage it  Why due diligence and setting financial goals matter in real estate investing  Ripple effects of sharing investing and entrepreneurial knowledge  A rewarding method to manage wealth  Resources/Links mentioned BiggerPockets Real Estate Investing Forums Essentialism by Greg McKeown | Kindle, Paperback, and Hardcover   About Spencer Hilligoss Spencer Hilligoss is the CEO and Co-Founder of Madison Investing. He is an active syndicator, investor, and speaker. He currently leads business development and investor relations for Madison Investing. He is a former technology executive with a 13-year track record building high-performing teams across five companies (three of their software "unicorns"- valued at over $1B). His last run in Silicon Valley was developing the Origination Team for LendingHome and leading their Professional Development group. ​Spencer is a 2023 Forbes Business Council member and Registered Representative of Finalis Securities LLC, Member FINRA/SIPC.   Connect with Spencer Website: Madison Investing   Are you ready to experience the cash flow life? Just text “BOOK” to (480) 500-1127 to get a FREE copy of Corey's book, Copy Your Way to Success, and learn how apartment investing can change your life today! Don't forget to download my Free Workshop Quick Start Video Series, and if you like what you have heard, please leave a review on iTunes.

Getting out of the corporate grind is something that everyone strives for. Just before the pandemic started, Spencer Hilligoss managed to achieve his financial independence from his day job. Adam Schroeder talks with Spencer, founder of Madison Investing, about his real estate journey, how he gained confidence as he continued investing, and Spencer's 5 part process for vetting deals across multiple real estate asset classes. Website: www.MadisonInvesting.com ***To receive your copy of Zach's Top 20 Markets to Invest in 2023, email your request to podcast@renttoretirement.com*** -------------------------------------------------------- Website - www.RentToRetirement.com YouTube - www.YouTube.com/RentToRetirement Current Hotlist Properties - www.RentToRetirement.com/Hotlist

Getting out of the corporate grind is something that everyone strives for. Just before the pandemic started, Spencer Hilligoss managed to achieve his financial independence from his day job. Adam Schroeder talks with Spencer, founder of Madison Investing, about his real estate journey, how he gained confidence as he continued investing, and Spencer's 5 part process for vetting deals across multiple real estate asset classes. Website: www.MadisonInvesting.com ***To receive your copy of Zach's Top 20 Markets to Invest in 2023, email your request to podcast@renttoretirement.com*** -------------------------------------------------------- Website - www.RentToRetirement.com YouTube - www.YouTube.com/RentToRetirement Current Hotlist Properties - www.RentToRetirement.com/Hotlist

Today's guest, Spencer Hilligoss, is a passive investor who has deployed 7-figures of his own capital into passive investments in the past 6 years. In 2019, he retired from a 13-year career in Silicon Valley tech companies in order to give full focus to serving fellow investors in Madison Investing - a club where passive investors gain access to the same types of niche investment opportunities where he deploys his own money. To hear more about Spencer Hilligoss and his story, please make sure to tune into this week's episode of The Road to Financial Freedom.FREE TOOLKIThttps://camaplan.typeform.com/freetoolkitFor more information on Spencer Hilligoss:Website: www.madisoninvesting.comFor more information on CamaPlan:https://www.camaplan.com/Call the number below during business hours (8:30 AM - 5 PM EST) to schedule a phone consultation with CamaPlan:Phone: (215) 283-2868 Toll Free: (866) 559-4430.Follow our Podcast to stay up to date with upcoming guests, and other relevant topics:Website: https://www.RoadtoFinancialFreedomPodcast.com Facebook: https://www.facebook.com/CamaPlanPodcast/Instagram: @TheRoadtoFinancialFreedomPodLinkPage: https://linkpages.pro/EclTdARemember to like, follow, and share on your favorite podcasting platform!CamaPlan SDIRA, LLCCamaPlan, a self-directed IRA administrator, makes alternative investing a breeze for clients.The Road to Financial Freedom is Social! Check us out on Facebook & Instagram!!

Today we have Spencer Hilligoss on the show! Is your day-to-day job leaving you too little time to spend with family? Spencer Hilligoss was in the same boat and decided that it was time for a change – he started investing in real estate, and changed his life forever. Spencer Hilligoss spent 13 years in Silicon Valley tech companies before he became invested and partnered in over 40 large real estate deals split between large apartment communities and self-storage facilities in the sunbelt of the United States. Despite growing up in a real estate household, with his dad as a broker who made him work open houses as a teenager, Spencer was initially scared off by the industry and opted for tech. But now, he is thriving as a successful real estate investor and is particularly fond of the Texas market. In this episode you will learn: the typical three phases real estate investors pass through his experience investing seven figures into real estate syndications focus on the "who" what is the goal for the money his seven point investor guide Listen and learn. For links and resources discussed in this episode, please visit our show notes at https://darinbatchelder.com/investments-that-pay-monthly

With over 15 years of experience in real estate investing and a passion for educating others, Spencer outlines his five-part decision-making framework for vetting passive investments. He emphasizes the importance of communication and delivering news well in building trust with investors. He also discusses the challenges of balancing a high-powered career with family life and finding a different way to live through real estate investing.    As the market shifts in 2023, Spencer aims to educate and serve others with his experience and investment opportunities. He emphasizes the need for sponsors to be responsive and transparent in their answers to investors' questions. Lastly, he touches on the importance of learning from challenging experiences as an entrepreneur. Jump right in to learn valuable insights into passive real estate investing and how to evaluate investment opportunities!   [00:01 - 09:36] Spencer's History of Investing Spencer Hilligoss invested over seven figures personally of his own money into deals as a passive investor He stepped away from his career in Silicon Valley in October 2019 after building loan origination groups for a fix-and-flip lender that was also a tech company Communication is key for passive investors in real estate   [09:37 - 19:38] Five-Part Decision-Making Framework for Passive Investments Track record approach Team approach Communications Quantitative approach Values   [19:39 - 24:45] Key Factors in Passive Real Estate Investing Transparency and clear communication are essential in real estate investing Red flags to look out for include slow or unclear investor communications Values should be considered when investing, including how tenants are treated Behavioral interviewing can help gauge a sponsor's experience and ability to handle challenges   [24:46 - 29:11] Closing Segment Best investment: buying their first home Worst investment: putting money into Crypto The most important lesson learned: the world is very connected   Quotes:   "Humility is key in life for thriving." - Spencer Hilligoss   "Just tell people what's happening. Treat people like adults, and speak to them as adults. Don't hide stuff." - Spencer Hilligoss Connect with Spencer! Website: www.MadisonInvesting.com  Invest passively in multiple commercial real estate assets such as apartments, self-storage, medical facilities, hotels, and more through https://www.passivewealthstrategy.com/crowdstreet/ Track your rental property's finances with Stessa. Go to www.escapingwallstreet.com. Join our Passive Investor Club to access passive commercial real estate investment opportunities. LEAVE A REVIEW + help someone who wants to explode their business growth by sharing this episode or clicking here to listen to our previous episodes.

On this episode of The Millionaire Choice Podcast, Tony talks with Spencer Hilligoss, the founder and CEO of Madison Investing, a real estate investment firm that helps investors build passive income through commercial real estate. In this episode, we'll be discussing why real estate is the ultimate wealth-building vehicle and how you can start investing in real estate to achieve financial freedom. Key Takeaways: Real estate is a proven way to build wealth: Spencer Hilligoss shares his personal journey of how he transitioned from working in tech to becoming a successful real estate investor. He explains why real estate is a proven way to build long-term wealth and achieve financial freedom. Understanding the different types of real estate investments: There are different types of real estate investments, such as residential, commercial, and industrial. Spencer shares his expertise on commercial real estate and how it can provide higher returns than other types of investments. The power of syndication: One way to invest in commercial real estate is through syndication. Spencer explains how syndication works and how it allows investors to pool their resources to invest in larger deals that they couldn't afford on their own. Tips for getting started in real estate investing: Spencer provides some valuable tips for anyone looking to get started in real estate investing, including how to find the right investment opportunities, how to build a team, and how to manage risk. Wrap-Up Real estate investing can be a powerful way to build wealth and achieve financial freedom. Spencer Hilligoss shares his insights on why real estate is the ultimate wealth-building vehicle and how you can start investing in real estate today. Tune in to The Millionaire Choice Podcast to learn more about how to make smart financial decisions and build wealth. To connect with Spencer Hilligoss and Madison Investing, visit https://madisoninvesting.comSee omnystudio.com/listener for privacy information.

Spencer Hilligoss is the CEO of Madison Investing - a real estate investment club with bespoke, curated real estate deals. Spencer founded Madison Investing with a singular mission: to help busy, successful professionals invest passively, secure their most valuable asset of all: Time. By partnering with in-market, vetted operators, Madison Investing has $2.3B in acquisitions, with over 20,000 units. Investors now have access to cash-flowing private real estate syndications and funds, allowing them to enjoy passive returns as these businesses thrive. Before starting Madison Investing, Spencer was what some consider a “corporate junkie”, growing operations and sales teams in 5 high growth Fintech companies, over the span of 13 years. In 2019, five months before the pandemic, Spencer broke free from the golden handcuffs to give full focus on serving his investment group and growing Madison Investing. Now, as a full time investor and entrepreneur, he can spend more time with his family and honing his skills on the electric guitar. He is a registered member of FINRA and a member of the Forbes 2022 Real Estate Council.

Attention all entrepreneurs! Are you struggling to manage your time effectively while also planning for your financial future? Look no further than the Entrepreneur Conundrum podcast! In this episode, Virginia Purnell interviews Spencer Hilligoss, CEO of Madison Investing, about his journey as an entrepreneur and real estate investor. Spencer shares valuable insights on how to invest passively and secure your time by partnering with vetted operators. He also discusses the importance of intentional choices in one's career and the value of investing in real estate. Learn how to build your ideal customer persona, strategies for growing an investing club, and the importance of referrals in building a loyal customer base. The podcast also emphasizes the need for a sustainable and balanced approach to personal finances, with a focus on financial offense and defense. Plus, discover helpful tips on time management from the book "Essentialism" by Greg McEwen. Don't miss out on this valuable episode that will empower you to take control of your finances and time! Check out Madison Investing's website for even more resources and a free guide for passive investors. Join the conversation and be inspired to push boundaries and challenge assumptions in your own entrepreneurial journey. Podcast: Time management, passive investing, and financial planning for entrepreneurs- Interview with Spencer Hilligoss, CEO of Madison Investing- His entrepreneurial journey and mission to help busy professionals invest passively- Importance of intentional career choices and investing in real estate- Building an ideal customer persona and strategies for reaching them- Approaches to building and growing an investing club- Importance of referrals and a balanced approach to personal finances- Cultivating curiosity and challenging assumptions as a key factor in being a successful entrepreneur- Importance of building relationships and treating employees with kindness and respect- Financial planning for business owners who exit their businesses- Recommendation of "Essentialism" by Greg McEwen for improving time management skills. KEY QUESTIONSVirginia Purnell 00:01:36 can you tell us a bit about your entrepreneurial journey? Virginia Purnell 00:05:06 So who would be your ideal client or Avatar for Madison Investing?Virginia Purnell 00:07:31 So how do you get in front of them, in front of your ideal client?Virginia Purnell 00:11:44 You had mentioned a couple of times, like things that you wish you had known and things that you wish your club, people in your club before they join New. What are some of those things?Virginia Purnell 00:15:27 So what's a couple of big goals or a big goal that you're looking to achieve in the next year or two?Virginia Purnell 00:18:27 What is the best advice that you have ever received?Virginia Purnell 00:20:23 So what's the best advice you think you've ever given?Spencer Hilligosswww.madisoninvesting.comlinkedin.com/in/shilligoss Virginia PurnellFunnel & Visibility SpecialistDistinct Digital Marketing(833) 762-5336virginia@distinctdigitalmarketing.comwww.distinctdigitalmarketing.comBook a Free Call http://bit.ly/DDMBookACallEC

Is your financial advisor really looking out for you?Many investors question whether their FA has their best interests at heart. But seeking out alternative investments on your own can be scary, especially if the stock market is all you've ever known.So, what can you do to learn more about alternative investments like self-storage, cryptocurrency, ATMs or real estate? And can you achieve financial freedom in just a few years as a passive investor?Spencer Hilligoss is a former technology executive with a 13-year track record building high performing teams across five companies. He and his wife, Jennifer, achieved financial freedom through passive investing in multifamily and other alternative asset classes.Today, Spencer serves as Cofounder and CEO of Madison Investing, a platform that helps busy professionals generate passive income through vetted real estate investments.On this episode of Financial Freedom with Real Estate Investing, Spencer joins Garrett and me to explain how he educated himself around alternative investments like mobile home parks, data centers and multifamily syndications.Spencer discusses the framework he and Jennifer created to make good investment decisions, describing what they look for in a deal and how they vet an operator.Listen in for Spencer's insight on breaking into a new asset class and find out where he sees opportunities for investors in 2023 and beyond! For full episode show notes visit: https://themichaelblank.com/podcasts/session363/

Syndication Made Easy with Spencer Hilligoss This podcast features Vinney Chopra, the host of Apartment Syndication Made Easy, interviewing Spencer Hilligoss the CEO and co-founder of Madison Investing, a real estate investment firm specializing in real estate syndications. Spencer has a 13-year track record over one billion dollars and is a member of the Forbes Real Estate Council 2021. They discuss how this is the right time to invest in real estate and the importance of sharpening one's pencil and making confident decisions. They mention different types of properties such as apartment buildings, mobile home parks, strip shopping centers, hotels, industrial buildings, storage units, and senior living facilities. One valuable lesson we can learn is the importance of setting clear and achievable goals in order to achieve success. They emphasize the need to be specific when setting goals, and to break them down into smaller, manageable steps. By doing so, we can avoid feeling overwhelmed and increase our chances of actually accomplishing what we set out to do. Another lesson is the value of persistence and hard work. The fact that success often comes after repeated failures and setbacks, and that those who are willing to keep pushing through despite the challenges are the ones who ultimately succeed. Lastly, The importance of taking action and not just talking about our goals or plans. We need to be willing to take risks and put in the effort required to achieve our desired outcomes. www.madisoninvesting.com Watch the Full Video here: https://youtu.be/DEEHGNYRjCA Don't forget to head over to iTunes to subscribe, rate, and leave a review. It's very much appreciated.    https://podcasts.apple.com/us/podcast/syndication-made-easy-with-vinney-smile-chopra/id1473126675   INVEST with Vinney [Accredited Investors ONLY]: https://www.accreditedinvestor.blog/book-a-call LEARN from Vinney: https://vinneychopra.com/mentoring Want more information about value-add multifamily investment properties? Click here: https://multifamilymentor.blog

Ep.#1 [THEME EIGHT] “Money can’t buy a calm mind, a fit body, a house full of love” - The Naval Podcast. In the episode where I heard this quote, Naval points out how Bezos, one of the wealthiest people on the planet, can’t use any of his money to buy these things. Does this resonate with you? It hit me like a ton of bricks. It made me think of all the people who have been on this podcast after selling their companies, have a huge portfolio of assets, and are still not happy because they have endless amounts of time and no purpose. Are you confident you are spending your time, energy, and capital each day in areas that will get you closer to where you want to be? In order to confidently answer yes, you need to peel back the onion and first figure out where you are today and then clarify your ideal vision for the future. I have found this to be a tough question for people to answer when I ask them “why” five times. Typically, when asking a business owner or entrepreneur what their goal is, I get an answer like revenue, net income, units, subscribers, employee count, or some other metric that–to me–is more of a vanity metric than an indicator of what that person truly values in life. On today’s show, I interviewed Spencer Hilligoss, the CEO of Madison Investing, a real estate investment club that has completed $2.3 billion in acquisitions with over 20,000 units. Spencer founded Madison Investing after sitting down with his wife–and now business partner –after hitting a breaking point while grinding away in their W2 jobs. They sat down and created a 15-year vision that included the annual income they needed to decouple their income from their labor, how they wanted to spend their time each day, and how they were going to achieve it. Spencer and Jennifer accomplished their 15-year plan within half the time and are now rethinking again what they want their life experiences and purpose to be. I really enjoyed the conversation with Spencer because of how clearly he describes the evolution to his approach and views on life, business, money, and time. He explains why he protects what he values and how he wants to spend the time he has each week, and why, regardless of the level of “success” he achieves. Do you want to be confident you are spending your time, money, and energy on the right things? The best way to answer this question is to think about what you want beyond just the vanity metrics. Regardless of how much money you make–or how big your company is–you will still be stuck with yourself, your mind, your body, and the people around you. On today’s show you will learn how to start thinking about your future goals in a new way. // WATCH THE INTERVIEW ON YOUTUBE: Intentional Growth™ Podcast What You Will Learn Why identifying the amount of annual income you need that is not tied to your labor–and how you will achieve it–is a crucial step to a

Seasoned investor Spencer Hilligoss joins us in today's episode to share how you can utilize financial offense and defense in your company so you can stop trading your time for money. Discover the steps to scale your business today by pressing that play button!WHAT YOU'LL LEARN FROM THIS EPISODE The 3 phases of investing: Lessons and realizationsUnique qualities you need to be a successful investorCore principles a thriving business should haveProactive steps to building and growing your investor networkBenefits and drawbacks of establishing a business with your spouseRESOURCES/LINKS MENTIONEDRich Dad Poor Dad by Robert Kiyosaki | Paperback https://amzn.to/3V3Jfox and Kindle https://amzn.to/3RJ4VDsBiggerPockets https://www.biggerpockets.com/finra https://www.finra.org/#/ABOUT SPENCER HILLIGOSSSpencer is the CEO and co-founder of Madison Investing. He is an active syndicator, investor, and speaker and currently leads business development and investor relations for Madison Investing. Spencer is a 2021 Forbes Real Estate Council member and a Registered Representative of Finalis Securities LLC Member FINRA/SIPC.CONNECT WITH SPENCERWebsite: Madison Investing https://www.madisoninvesting.com/LinkedIn: Spencer Hilligoss https://www.linkedin.com/in/shilligoss/Email: spencer@madisoninvestment.comCONNECT WITH USWant a list of top-rated real estate conferences, virtual meetups, and mastermind groups? Send Tate an email at tate@glequitygroup.com to learn more about real estate using a relational approach.Looking for ways to make passive income? Greenlight Equity Group can help you invest in multifamily properties and create consistent cash flow without being a landlord. Book a consultation call and download Tate's free ebook, "F.I.R.E.-Financial Independence Retire Early via Apartment Investing," at www.investwithgreenlight.com to start your wealth-building journey today!

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. His mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals.Prior to pivoting to real estate, Spencer held several executive roles in the financial technology industry. Throughout his career, one thing has remained consistent: his ability to keenly focus on professional development- helping teams and individuals reach their full potential. Spencer is a member of the 2021 Forbes Real Estate Council and has been featured in publications such as Business Insider. CONNECT WITH SPENCEREmail: spencer@madisoninvesting.comWebsite: https://www.madisoninvesting.com/CONNECT WITH JONATHANTo connect with Jonathan, you can send email at info@greystonecapgroup.com. To learn more about real estate investment opportunities, join the Greystone Capital Investor Network.Thanks for listening and until next time, keep building wealth in Commercial Real Estate! 

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals. You can connect with Spencer through linkedin: linkedin.com/in/shilligoss What does Freedom mean to you? Check out our webinar: “How Top Sales Pros Create Passive Income & Achieve Financial Freedom With Hands-Off Real Estate Investing”   Download our free eBook on “Passively Investing in Real Estate” by going to www.hightechfreedom.com   Host Contact Information - Chris Freeman LinkedIn - http://linkedin.com/in/chrisfreeman Facebook - https://www.facebook.com/chris.freeman.9461   

Spencer breaks down what he would like to do in the past to foster and develop relationships. Multifamily is a relationship game, we invite you to put precedence on these relationships as soon as possible!   madisoninvesting.com   Get your videos produced at pitchdecks.com like the Capital Raiser Show. If you would like to find out more about Family Office Capital Raising events you can visit lnkd.in/gD6mJ5gp Book a call with Ruben at calendly.com/rlgreth  

Co-GP's vs. Finra and Licensing vs. Fund Models. Let's chat about eliminating risk, partnering with sponsors, being a placement agent, educating investors, doing deep due diligence at a redundant level, vetting deals, vetting sponsors, raising capital and investor communications. Let's also go down the road of how to make your money die! madisoninvesting.com   Get your videos produced at pitchdecks.com like the Capital Raiser Show. If you would like to find out more about Family Office Capital Raising events you can visit lnkd.in/gD6mJ5gp Book a call with Ruben at calendly.com/rlgreth

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals.Spencer graciously appeared as one of the early guests on my previous podcast.  For a more intimate and in-depth perspective on what makes this accomplished investor and entrepreneur excel, go to episode 15 Creek Side Chats with Successful Real Estate Investors.Main Points:Entrepreneurs are fantastic at building a machine- not so great at preserving their wealth once they retireHow do you think about wealth preservations? Different questions arise.What is enough? A simple word can mean so many things.Connect With Spencer Hilligoss:spencer@madisoninvesting.com+1 (415) 290-0328linkedin.com/in/shilligosshttp://www.madisoninvesting.com

1050 If you have extra cash just sitting in an account somewhere you are literally losing money. You put that money to work. Now there are many asset classes you can choose from but if it's passive investing that you are looking for then todays episode is for you! There are a ton of things to consider when investing in real estate like Research, evaluations, inspections, ROI and more, so investing can feel overwhelming! Todays guest is taking on all that work so that passive investing can be just that, passive! Let's find out more as we talk Real Estate Investing with Spencer Hilligoss ___________ Go to www.BusinessBros.biz to be a guest on the show or to find out more on how we can help you get more customers! #Businesspodcasts #smallbusinesspodcast #businessmarketingtips #businessgrowthtips #strategicthinking #businessmastery #successinbusiness #businesshacks #marketingstrategist #wealthcreators #businessstrategies #businesseducation #businesstools #businesspodcast #businessmodel #growthmarketing #businesshelp #businesssupport #salesfunnel #buildyourbusiness #podcastinglife #successgoals #wealthcreation #marketingcoach #smallbusinesstips #businessmarketing #marketingconsultant #entrepreneurtips #businessstrategy #growyourbusiness --- Support this podcast: https://anchor.fm/businessbrospod/support

Spencer Hilligoss is a full time investor and former operations leader who walked away from a lucrative career of 13 years across 5 high-growth Fintech companies. In 2019, five months before the pandemic – Spencer left behind the golden handcuffs to give full focus on serving Madison Investing's passive investor group.Now, Spencer's full focus goes to Madison Investing – a passive investing group with hundreds of members actively deploying capital with Madison's vetted sponsors and deals in high-growth markets across the US. Spencer and his wife/COO Jennifer put their own personal skin-in-the-game with each operator as the cornerstone of a 5-part sponsor vetting framework, designed to de-risk the toughest question facing every passive investor: “can I trust this team with my capital?”Madison Investing specializes in real estate syndications and private equity funds – focused on multifamily, self storage and niche asset classes. Madison has partnered on real estate deals totaling more than 10,000 units – spanning 36 deals and 13 full-cycle exits.Spencer is a father of two, an avid guitar player, graduate of CU Boulder and currently based in the Bay Area, California. He is a registered member of FINRA and a member of the Forbes 2022 Real Estate Council. Madison Investing is accepting applications from new members who meet Accredited Investor requirements:Learn more: https://www.madisoninvesting.com/interview-with-spencer-hilligoss-ceo-and-co-founder-of-madison-investingInfluential Entrepreneurs with Mike Saundershttps://businessinnovatorsradio.com/influential-entrepreneurs-with-mike-saunders/Source: https://businessinnovatorsradio.com/

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals.Prior to pivoting to real estate, Spencer held several executive roles in the financial technology industry, including positions at Intuit and Gusto—forging a 13-year track record of building high-performing teams across five companies (three of which were valued at over $1B). Throughout his career, one thing has remained consistent: his ability to keenly focus on professional development- helping teams and individuals reach their full potential. Spencer is a member of the 2021 Forbes Real Estate Council and has been featured in publications such as Business Insider. When he's not shifting the way people think about investing, you can find him listening to metal, adding to his tattoo collection, and jogging through the Bay Area with his wife and two sons. Ask him about the time he played onstage in San Francisco at the Vans Warped Tour!We chat about:Playing Financial Offense vs. DefenseWealth Preservation & Planning Your LegacyThe Intersection of Personal and Professional DevelopmentDeclining Executive Roles to Build Your Own Financial MoatReal Estate Syndication From A to ZConnect with Spencer at his website https://www.madisoninvesting.com/LIKE • SHARE • JOIN • REVIEWWebsiteJoin the REI Mastermind Network on Locals!Apple PodcastsGoogle PodcastsYouTubeSpotifyStitcherDeezerFacebookTwitterInstagramSUPPORT THE SHOW!Self Managing Your Rental Properties? Get 6 months of RentRedi for $1! Click this link!Get Exclusive Content on Patreon! • https://www.patreon.com/reimastermindGet $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumoGet $10 Towards Your First Purchase at Drop

Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals. Prior to pivoting to real estate, Spencer held several executive roles in the financial technology industry, including positions at Intuit and Gusto—forging a 13-year track record of building high-performing teams across five companies (three of which were valued at over $1B). Throughout his career, one thing has remained consistent: his ability to keenly focus on professional development- helping teams and individuals reach their full potential. Spencer is a member of the 2021 Forbes Real Estate Council and has been featured in publications such as Business Insider. When he's not shifting the way people think about investing, you can find him listening to metal, adding to his tattoo collection, and jogging through the Bay Area with his wife and two sons. Ask him about the time he played onstage in San Francisco at the Vans Warped Tour! We chat about: Playing Financial Offense vs. Defense Wealth Preservation & Planning Your Legacy The Intersection of Personal and Professional Development Declining Executive Roles to Build Your Own Financial Moat Real Estate Syndication From A to Z Connect with Spencer at his website https://www.madisoninvesting.com/ (https://www.madisoninvesting.com/) LIKE • SHARE • JOIN • REVIEW http://reimastermind.net/ (Website) https://reimastermindnetwork.locals.com/ (Join the REI Mastermind Network on Locals!) https://podcasts.apple.com/us/podcast/rei-mastermind-network-real-estate-investing-strategies/id1227366661 (Apple Podcasts) https://podcasts.google.com/feed/aHR0cDovL3JlaXJvb2tpZXMubGlic3luLmNvbS9yc3M (Google Podcasts) https://www.youtube.com/channel/UC_6OpKSfSGvgGDG1qtBQw9Q (YouTube) https://open.spotify.com/show/4P66jm0Q4PMl7OoZzHMUUZ (Spotify) https://www.stitcher.com/show/rei-rookies (Stitcher) https://www.deezer.com/us/show/2148782 (Deezer) https://www.facebook.com/REIMastermindNet (Facebook) https://twitter.com/rei_mastermind (Twitter) https://www.instagram.com/reimastermindnet/ (Instagram) SUPPORT THE SHOW! Self Managing Your Rental Properties? https://app.rentredi.com/signUp/JCH191 (Get 6 months of RentRedi for $1! Click this link!) https://www.patreon.com/reimastermind (Get Exclusive Content on Patreon! • https://www.patreon.com/reimastermind) https://bit.ly/reiappsumo (Get $10 and Reduce Your Business Costs by Shopping at AppSumo • https://bit.ly/reiappsumo) https://drop.com/?referer=3DC729 (Get $10 Towards Your First Purchase at Drop • https://drop.com/?referer=3DC729) "You can invest 10,000 hours and become an expert or learn from those who have already made that investment." - Jack

Discover how passive income streams from multifamily real estate investing can significantly impact your life as we have Spencer Hilligoss today! In this episode, you'll be motivated by his journey of starting from single-family rentals, a crucial question you should ask yourself as an investor, and how real estate investing offers time and financial freedom. Never miss a single episode of this show to acquire more value!   Key takeaways to listen for  Why you should have multiple income streams The biggest difference between single-family and multifamily  What does “asymmetrical risk-to-reward ratio” mean Is it okay to sit on the sidelines during the rising interest rates? The reward of being a full-time real estate investor How to approach today's market volatility   Resources mentioned in this episode Go to www.madisoninvesting.com/get-started to subscribe to Madison Investing's newsletter.   About Spencer Hilligoss Spencer Hilligoss is the CEO & Co-Founder of Madison Investing, a real estate investment firm specializing in real estate syndications. As a passive investor and active syndicator, he understands the unique challenges that busy professionals face when starting out on their REI journey. Spencer's mission is to arm investors with the know-how they need to make confident investment decisions tailored to their individual life goals. Prior to pivoting to real estate, Spencer held several executive roles in the financial technology industry, including positions at Intuit and Gusto—forging a 13-year track record of building high-performing teams across five companies (three of which were valued at over $1B). Throughout his career, one thing has remained consistent: his ability to keenly focus on professional development- helping teams and individuals reach their full potential.  Spencer is a member of the 2021 Forbes Real Estate Council and has been featured in publications such as Business Insider. When he's not shifting the way people think about investing, you can find him listening to metal, adding to his tattoo collection, and jogging through the Bay Area with his wife and two sons. Ask him about the time he played onstage in San Francisco at the Vans Warped Tour!   Connect with Spencer Website: Madison Investing  LinkedIn: Spencer Hilligoss Instagram: @spencer_hilligoss Email: spencer@madisoninvesting.com Phone: (415) 290-0328   Connect with Us To learn more about partnering with us, visit our website at https://javierhinojo.com/ and www.allstatescapitalgroup.com, or send an email to admin@allstateseg.com.  Sign up to get our Free Apartment Due Diligence Checklist Template and Multifamily Calculator by visiting https://javierhinojo.com/free-tools/. To join Javier's Mastermind, go to https://javierhinojo.com/mastermind/ and to apply to his BDB Mastermind, see https://javierhinojo.com/mastermind/#apply_form and answer the form.   Follow Me on Social Media Facebook: Javier A Hinojo Jr. Facebook Group: Billion Dollar Multifamily and Commercial Real Estate YouTube Channel: Javier Hinojo Instagram: @javierhinojojr TikTok: @javierhinojojr Twitter: @JavierHinojoJr

In this episode, Spencer tells us his background and how he used to be proud of investing in a 401k and other traditional investments.  Many of these lead to an increasing tax liability over time.  He awakened to the importance stepping away from "mainstream" thinking and looking to cashflow investments.  He talks with us here about playing both offense and defense and not driving up your lifestyle too quickly, but rather saving and beating inflation! He shares the need to constantly be growing money and keeping it in motion.  He tells us how to get curious and assume nothing when researching alternative investments.  He elaborates further on the importance of hard assets and tax efficiency.  He counsels us to turn away from the news while simply assuming your money is employed by you!  For more info, visit: MadisonInvesting.com

Listen as we talk to Spencer Hilligoss about how he was able to leave his high-paying tech job and still live in the Bay area all due to building a business around passively investing in multifamily deals.He is a passive real estate investor, multifamily co-sponsor and former technology leader. Alongside his wife who is his business co-founder and partner, he invests in syndications as a limited partner. His company Madison Investing has co-sponsored deals totaling more than 4,000 units and more than 500 million dollars.In November 2019, he retired from his lucrative technology career leaving behind a 4 billion, that's billion with a ‘B' loan origination team that he helped build at his former company lending home. You can find out more about him and his wife and how to invest with their company at:www.MadisonInvesting.comLinkedInFaceBookPublished: Apr. 14, 2020