The Lifestyle Investor - Investing, Passive Income, Wealth

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.