The Lifestyle Investor - Investing, Passive Income, Wealth

Entrepreneur Magazine calls Justin Donald “The Warren Buffett of Lifestyle Investing.” Imagine being able to earn passive income, long-term equity, and achieve financial freedom while gaining total freedom from your business or a job. That’s what Lifestyle Investing is all about. Justin Donald has mastered the low-risk cash flow investment principles he shares with entrepreneurs around the world. His alternative investing principles center on creating passive income and significant wealth while liberating yourself from a day-to-day job so you never run out of money. His innovative mindset principles and 10 commandments of Lifestyle Investing have released scores of entrepreneurs from the “golden handcuffs” that came with running life-consuming enterprises. This show focuses on showing today’s entrepreneurs and business executives how to think and invest to limit risk, maximize repeatable returns, and achieve retirement goals through his proven passive income

The Lifestyle Investor - Investing, Passive Income, Wealth is a business podcast hosted by Justin Donald, with 315 episodes on record and a Required Pod Score of 80.

Justin Donald hosts The Lifestyle Investor - Investing, Passive Income, Wealth, a business show with 315 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #309

  309: The First Step to Making Your Business More Valuable and Sellable with Eric Rozenberg

  Sep 24, 202634 min

  Entrepreneurship can provide incredible wealth and freedom, but not if you've created a company that can't function without you. When every important decision, client relationship, and responsibility runs through you, then you've essentially traded one job for another while limiting the value of the business you've worked so hard to build. That's why I'm excited to have Eric Rozenberg on the podcast. Eric is an entrepreneur, author, speaker, and consultant who has spent nearly three decades building, scaling, and exiting businesses in the meetings and events industry. Along the way, he's learned firsthand what happens when entrepreneurs try to do everything themselves and what it takes to build a company that creates freedom instead of consuming your life.  Eric's experience is particularly interesting as AI transforms how businesses operate while making genuine human relationships and face-to-face connections even more valuable. In our conversation, Eric shares his journey from corporate life to entrepreneurship, why people often choose misery over the uncertainty of change, and how AI could make in-person communities and events even more important. In this episode, you’ll learn:  ✅ Why reducing your involvement in the business can increase its value while giving you more freedom. ✅ How defining a compelling 10-year vision can help you make difficult decisions and stay aligned during the inevitable ups and downs of entrepreneurship. ✅ How asking yourself “Should I be the one doing this?” can help you delegate more effectively and build a business that doesn't depend on you. Show Notes: LifestyleInvestor.com/309 Tax Strategy Masterclass If 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/tax Strategy 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/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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  Episode #308

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

  Sep 17, 202655 min

  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/308 Tax Strategy Masterclass If 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/tax Strategy 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/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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  Episode #307

  307: Why Asking for Help Is a Superpower for Success with Nathan Thomas

  Sep 10, 202644 min

  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/307 Tax Strategy Masterclass If 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/tax Strategy 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/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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  Episode #306

  306: How Wealthy Families Use Whole Life Insurance as a Family Bank with Brock Fortner

  Sep 3, 202642 min

  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/306 Tax Strategy Masterclass If 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/tax Strategy 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/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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  Episode #305

  305: The 3 Health Metrics Everyone Should Be Tracking To Improve Longevity with Dr. Ryan Williamson, M.D.

  Aug 27, 202642 min

  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/305 Tax Strategy Masterclass If 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/tax Strategy 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/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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