308: What Two 9-Figure Exits Taught a Serial Entrepreneur About Investing with Ben Rubenstein

Building a successful company can create generational wealth. But once you've had a big exit, figuring out how to invest that money without taking unnecessary risks can be more challenging than many people would think.That’s why I'm excited to have Ben Rubenstein on the podcast. Ben is a serial entrepreneur, investor, and the founder and Principal of SetPoint Capital, an asset-backed private credit platform and technology company. He’s had multiple 9-figure exits after co-founding Yodle, which sold for $342 million, and Opcity, which sold for $210 million. Today, Ben brings his experience as both an operator and investor to building technology and investment strategies across real estate, fintech, and private credit.In this conversation, we discuss the lessons Ben learned from scaling and exiting multiple companies and why he believes great businesses are built around customers rather than ideas. We also talk about what separates safer forms of private credit from the risks making headlines today, and how his experience on both sides of the table has shaped how he thinks about investing his own wealth.In this episode, you’ll learn: ✅ Why Ben uses a barbell approach to investing that combines safer cash-flow investments with concentrated opportunities where he has a competitive advantage.✅ How asset-backed lending, aligned incentives, and new technology can create additional layers of protection for private credit investors.✅ Why deep due diligence becomes even more important as investors move beyond traditional stocks and bonds into alternative investments.Show Notes: LifestyleInvestor.com/308Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

One of the biggest stumbling blocks many entrepreneurs and high-achievers face is believing they can figure almost anything out on their own. Asking for help often feels like admitting weakness. But sometimes, the very thing standing between you and the next level of your life is your willingness to admit you don't have all the answers.Today's guest, Nathan Thomas, knows firsthand how powerful that realization can be. After years of struggling with addiction and nearly destroying his life, Nate got sober, embraced humility working as a barista, and eventually worked his way up to become VP at Goldman Sachs.But he soon realized that the corporate world wasn’t his calling and went on to become co-founder and CEO of Shmoody, a mental health and wellness platform that has reached millions of users. Fast forward to today, and he’s now in the final steps of releasing his first book, Ask for Help, using his own story to show people how they can change their lives by asking for help, both spiritually and practically.In our conversation, Nate shares his remarkable journey from addiction and rock bottom to sobriety, entrepreneurship, and a life centered around serving others. We also discuss how those experiences reshaped his definition of success, the lessons he's carried into building Shmoody, and why some of life's greatest breakthroughs can come from being willing to admit you don't have all the answers.In this episode, you’ll learn: ✅ Why asking for help isn't a sign of weakness and how putting your ego aside can unlock relationships, mentorship, and opportunities you couldn't create alone.✅ Why the best mentors, peer groups, and relationships often require you to step outside your comfort zone and ask people you admire for their help. ✅ Why taking action matters more than controlling the outcome and how reframing rejection can give you the courage to pursue bigger opportunities.Show Notes: LifestyleInvestor.com/307Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Have you ever wondered what makes the wealthiest families, like the Rockefellers, so successful? They don't try to maximize the return on every dollar. Instead, they build diversified portfolios with different assets serving different purposes to provide liquidity, stability, and access to capital when opportunities arise.That's why I'm excited to welcome Brock Fortner back to the podcast. Brock is a wealth strategist at Stone Century Financial and a longtime member of the Lifestyle Investor Mastermind who has become one of my most trusted resources on dividend-paying whole life insurance. I've personally used whole life policies for nearly 25 years to store cash, fund investments, and create greater flexibility with my capital.In our conversation, Brock and I challenge some of the conventional thinking around asset allocation, the traditional 60/40 portfolio, and the idea that every dollar needs to earn the highest possible return. We also talked about teaching the next generation to think differently about money and some of the costly mistakes people make when choosing and structuring life insurance.In this episode, you’ll learn: ✅ The incredible benefits and flexibility of using whole life insurance in your cash and fixed-income portion of your portfolio.✅ How borrowing against your policy creates liquidity to quickly capitalize on new investment opportunities.✅ How wealthy families use whole life insurance to build a family banking system and transfer wealth for multiple generations.Show Notes: LifestyleInvestor.com/306Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

True wealth is about more than money. It's about having the freedom to buy your time back and live life on your terms. But none of it matters if you don't have the health and energy to enjoy the life you've worked so hard to create. With traditional healthcare falling short in helping people prevent disease before it starts, many high-achieving entrepreneurs are looking for better ways to take control of their health.Today's guest, Dr. Ryan Williamson, is a physician, entrepreneur, former Navy lieutenant commander, and longtime member of the Lifestyle Investor Mastermind. He's also the founder of Transcend Health, where he's combining advanced diagnostics, personalized medicine, and cutting-edge technology to help people take a more proactive approach to their health.In our conversation, Ryan explains why an annual physical isn't enough, which health metrics you should be tracking today, and how simple habits can dramatically improve metabolic health. We also explore how AI and emerging medical technologies are changing healthcare, why more high performers are turning to concierge medicine, and how Ryan's entrepreneurial journey transformed his definition of wealth and success.In this episode, you’ll learn: ✅ Why proactive healthcare starts long before symptoms appear and how regularly tracking your health data can uncover risks while you still have time to address them.✅ How regular blood work, wearables, blood pressure monitoring, movement, sleep can help you build a more complete picture of your health.✅ How AI, advanced diagnostics, and concierge medicine are creating a more personalized approach to health that can help entrepreneurs perform better and protect their longevity.Show Notes: LifestyleInvestor.com/305Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Lens #013 - Never Trust a Skinny Chef With Your MoneyAn old expression about eating your own cooking exposes a blind spot almost every investor has.Episode SummaryIn this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down why "skin in the game" matters more than brand reputation.You'll learn the stat on mutual fund managers with zero personal money invested, the 30-second due diligence question that filters out bad advisors, and the mistake Justin made trusting a fund he never checked.Question of the Day 🗣️Have you ever asked your financial advisor or fund manager how much of their own money is in the same investments they recommended to you? What happened when you asked? Drop your answer in the comments.Key Take-awaysNearly half of U.S. mutual fund managers have zero personal dollars in the funds they managePrivate market operators get asked "how much of your own money is in it?" - public fund managers almost never doBrand reputation creates "cover" that lets the skin-in-the-game question go unaskedA 30-second due diligence check filters out bad operators, bad funds, and bad adviceIf they hesitate when you ask, you already have your answerTimestamped Outline ⏱️00:00 – Introduction00:08 – The "never trust a skinny chef" principle00:25 – The stat: 47% of fund managers have $0 invested00:56 – The DUSLX example: three managers, zero personal dollars01:13 – Why this question gets asked in private markets but not public01:37 – How brand reputation provides cover01:55 – The lesson beyond mutual funds02:31 – Justin's personal mistake with a financial advisor02:59 – The question to carry with you03:14 – Closing thoughtsLinks & Resources 🔗Subscribe to The Lifestyle Investor Lens → https://lifestyleinvestor.com/lensConnect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/lensCreditsHost: Justin Donald © 2026 Lifestyle Investor. All rights reserved.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

A bigger paycheck isn't always the solution to financial stress. Despite rising incomes, millions of people—including high-income earners—continue living paycheck to paycheck because they never build the financial habits needed to create lasting wealth.That's why I'm excited to have Anthony O'Neal on the podcast. Anthony is a bestselling author, financial educator, and host of one of the fastest-growing personal finance platforms, The Table with AO.After overcoming homelessness and financial hardship himself, Anthony has helped millions of people eliminate debt and build healthier money habits to achieve financial freedom. His latest book, Stop Living Paycheck to Paycheck, outlines a proven framework for breaking free from financial stress and building wealth that lasts.In this conversation, we discuss why lifestyle inflation quietly keeps people trapped regardless of income, how eliminating consumer debt creates the margin needed to begin investing, and why true wealth comes from owning assets instead of keeping up with appearances. In this episode, you’ll learn: ✅ Why increasing your income won't solve your financial problems if your spending grows just as quickly.✅ How getting financially stable creates the foundation for every other wealth-building decision.✅ Why Anthony believes teaching financial literacy early could change the trajectory of an entire generation.Show Notes: LifestyleInvestor.com/304Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Lens #012 - 40 Entrepreneurs, 1 Skill Everyone Was MissingOne question every entrepreneur can answer. One question almost none of them can.Episode SummaryIn this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down the Four Wealth Quadrants and why most entrepreneurs are great at making money but never learn to manage, multiply, or direct it.You'll learn Kiyosaki's test for whether you actually own your business, why "can I afford this?" is the wrong question, and how financial freedom outside the business makes you sharper inside it.Question of the Day 🗣️Which of the four quadrants - Make, Manage, Multiply, or Make It Matter - is the one you've been avoiding? Drop it in the comments. Justin reads every response.Key Take-awaysMost entrepreneurs are A+ at making money and C- at managing, multiplying, and directing itKiyosaki's business test reveals whether you actually own your business or it owns you"Can I afford this?" is the wrong question - ask what's right for your family and business insteadQuadrant 4 (Make It Matter) sharpens your management and multiplication skills, not just your legacyFinancial freedom outside the business makes you a better operator inside itTimestamped Outline ⏱️00:00 – Introduction00:26 – The question that silenced the room00:51 – The four quadrants of wealth01:04 – Quadrant 1: Make Money02:03 – Quadrant 4: Make Money Matter03:00 – The Kiyosaki realization: "the business owned me"03:56 – "Can I afford this?" - the wrong question06:12 – Quadrant 4 exemplars: Maxwell, Weekley, Looper, Green06:57 – The challenge: which quadrant are you avoiding?Links & Resources 🔗The Lifestyle Investor by Justin Donald → https://lifestyleinvestor.com/Subscribe to The Lifestyle Investor Lens → https://lifestyleinvestor.com/lensConnect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/lensCreditsHost: Justin Donald © 2026 Lifestyle Investor. All rights reserved.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Investing in private markets has become one of the most sought-after opportunities for sophisticated investors. But while venture capital has created extraordinary wealth for some investors, success isn't simply about finding the next great startup. That’s why I'm excited to have Yotis Tonnelier on the podcast. Yotis is the co-founder and managing partner of YXS Capital, a venture capital firm focused on later-stage technology companies where he has delivered a 14.6x gross TVPI with zero losses across 14+ companies, and backed five unicorns including Mercury, Canva, and Wise.After exiting multiple businesses of his own, Yotis has developed a unique investment approach that combines the discipline of private equity with the growth potential of venture capital by helping identify high-quality companies long before they become household names.In this conversation, we discuss the growing role of secondary markets, the sectors Yotis believes offer the greatest long-term opportunities, and the principles that have shaped his investment philosophy throughout his career.In this episode, you’ll learn: ✅ Why Yotis believes investing after product-market fit can dramatically improve your odds of success while still capturing venture-level returns.✅ How relationships, reputation, and trust helped him create access to some of the world's most sought-after private investments✅ Why aligning incentives between fund managers and investors may be one of the biggest competitive advantages in venture capital today.Show Notes: LifestyleInvestor.com/303Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

LIL #011: 1,000 Lunches Built My Entire Investing CareerWhat if your most valuable asset isn't in your portfolio - it's in your phone?Episode SummaryIn this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down why your network is the highest-returning investment you'll ever make. You'll learn the 1,000-lunch habit that built his entire deal flow, a four-category framework for auditing your network, and why the cost of staying out of the right rooms far exceeds the cost of getting in.Question of the DayWho are the 3-5 people in your life right now who are actively elevating how you think about wealth and investing? If you can name them easily, you're ahead of most people. If you can't - that might be your biggest area of opportunity. Drop your answer in the comments.Key Take-awaysYour network is more valuable than any single investment, property, or business you own52 lunches a year for 20+ years compounds into deal flow money can't buyAudit your network across four categories to find the gaps holding you backBeing in a room with 50 people beats 50 individual conversations every timeThe cost of NOT being in the right rooms is always higher than the cost of entryTimestamped Outline00:00 - Introduction00:09 - What would you say your network is worth?00:52 - 1,000 lunches: the most valuable habit01:49 - Four categories of people you need in your network02:43 - The practical approach to building relationships03:41 - Why Justin is in 14 masterminds right now04:24 - The liberating shift: paying for the right rooms04:44 - The compound effect of networks05:48 - You don't need a billion dollar portfolio06:32 - Your challenge: name your 3-5 peopleLinks & ResourcesThe Lifestyle Investor Lens (weekly newsletter) - https://lifestyleinvestor.com/lensConnect & CTASubscribe and leave a review on Apple Podcasts.Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/CreditsHost: Justin Donald © 2026 Lifestyle Investor. All rights reserved.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Creativity is usually associated with artists, musicians, and filmmakers, not entrepreneurs and investors. People either have it or they don't... or at least that's what most of us have been led to believe. But today's guest expertly challenges that assumption and explains why creativity may be one of the most valuable wealth-building skills you can develop.Nick Nanton is a 24-time Emmy Award-winning director, producer, songwriter, and entrepreneur who has directed more than 75 documentaries featuring some of the world's most influential leaders, entertainers, and innovators. Through decades of storytelling and business building, he's developed a unique perspective on creativity, resilience, and success.In our conversation, we discussed the surprising lessons Nick learned from producing documentaries featuring world-class performers and entrepreneurs, the behind-the-scenes experiences that shaped his perspective while documenting anti-human trafficking missions, and why curiosity may be one of the greatest predictors of long-term success.In this episode, you’ll learn: ✅ Why Nick believes creativity is simply the ability to see options where others see obstacles and why that mindset can transform your investing, business, and personal life.✅ How embracing the traits that make you different can become your greatest competitive advantage instead of something you feel pressured to hide or change.✅ Why serving others creates new opportunities, unlocks creativity, and helps you overcome scarcity by shifting your focus toward creating value for those around you.Show Notes: LifestyleInvestor.com/302Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.