The Lifestyle Investor - Investing, Passive Income, Wealth

Justin Donald

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 cash flow strategies. Justin’s principles enable you to move from an “earned income” career to support your lifestyle with passive cash flow investments including real estate, operating companies, debt, equity, and franchises that give you the absolute freedom to live the life you truly desire. Interviews with top thought leaders, such as, John Lee Dumas, Ryan Levesque, Hal Elrod, Jon Vroman, Mike Koenigs, Phillip Stutts, Rob Dial, John Ruhlin, Brad Johnson, Robert Glazer, Mike Michalowicz, Geoff Woods, Steve Sims, and many more! For more information, visit https://justindonald.com

  1. 2d ago

    Lens #015 - Why the IPO is over (and where the money actually went)

    Ten years ago the goal was always the same. Build the company, ring the bell, take it public. That was the entire endgame and everyone organized around it. Today most of the companies people actually want to own are avoiding the public markets completely.   Uber stayed private for 9 years. Airbnb for 11. Stripe is worth over $95 billion and still hasn't listed. OpenAI is still private. If you're waiting on IPO liquidity to deploy capital, you're waiting on something that's happening less and less every year.   In this one I break down where that money went instead, and why the secondary market has grown into the trillions while most retail investors have never heard of it. Founders and early investors still need liquidity long before an exit, so they sell already-issued shares to someone else, and the buyer gets Series C or D upside with a better risk profile than early-stage.   The biggest institutions in the world are already there. Blackstone, Goldman, Berkshire. In certain niches like defense tech, the largest buyer is the government itself, which tells you plenty about where capital is actually flowing.   I also share numbers from a secondaries-focused fund I'm involved with. 50% gross IRR over roughly five years, 14 out of 14 investments returning positive, exposure to 5 unicorns. Everyone is fighting over the next seed round while the less crowded opportunity sits one stage later.   CHAPTERS: 00:00 The playbook changed and nobody announced it 01:00 Why companies stay private for 10 years now 02:30 How a secondary transaction actually works 04:00 Who's buying, and why the institutions moved first 05:30 What this changes about where you put capital   👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens   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.   Nothing here is financial advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  2. Oct 20

    Lens #014 - Why your savings are losing 10% a year (not 3 anymore)

    The government reports a number every month and most people treat it as the truth. 2.8%, 3%, whatever it happens to be that quarter. Meanwhile the dollar itself is losing value at a completely different rate, and the gap between those two figures is where your savings are going.   In this one I break down the difference between inflation and debasement, and why only one of them tells you what your money is actually worth.    Gold near $4,900, Bitcoin at $72,000, silver at $77. Those moves are telling you something about the dollar that the reported figures are not.   I also walk through the three categories I think about. Cash and bonds, which lose to debasement every year. Productive assets like stocks, real estate and crypto, which can keep pace. And leveraged positions on specific trends, which can outpace it with more risk attached. Most people sit almost entirely in the first category and call it saving.   When debt grows faster than GDP, printing becomes the easiest way to service it regardless of who's in office, and that pressure lands in asset prices.   CHAPTERS: 00:00 Inflation and debasement are not the same word 00:50 What the reported number actually measures 02:10 What 10% a year costs you sitting in cash 03:30 The three categories your money can sit in 05:10 Why more printing is coming, and your decision   👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens   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.   Nothing here is financial advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  3. Oct 20

    311: The Hidden Cost of Poor Company Culture with Cathy Christen

    Growing a business is one thing. Building a business that can sustain that growth without everything falling apart is another. As companies grow, the challenges change. Decisions pile up, priorities get confused, talented employees become frustrated, and founders often find themselves working harder than ever just to keep everything moving. That's why I'm excited to welcome my longtime friend Cathy Christen to the podcast. Cathy is the founder and CEO of Elevated You, a leadership and culture strategist, and has spent more than 20 years building businesses, developing leaders, and helping entrepreneurs create stronger teams and company cultures. She's also the author of The SCALE Advantage, which explores the five essential pillars of building a high-performing company to help businesses grow without sacrificing the people who make that growth possible. In our conversation, Cathy shares how a conversation we had more than 20 years ago completely changed her approach to entrepreneurship and helped her escape the workaholic lifestyle she'd created. We also discuss the lessons we've learned from hiring the wrong people, the challenges of keeping teams aligned as businesses grow, and why the human side of business may become even more valuable as AI continues to transform the workplace. In this episode, you’ll learn:  ✅ How Cathy’s SCALE framework helps entrepreneurs build stronger teams, improve accountability, and create sustainable growth. ✅ The hidden financial costs of poor company culture, including lost talent, wasted time, and the leadership mistakes that can quietly destroy an otherwise successful business. ✅ Why great employees, better systems, and new technology aren't enough to scale successfully, and what it takes to create a team that can execute without your constant involvement. Show Notes: LifestyleInvestor.com/311 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 FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  4. Oct 5

    310: From Living in a Van to $1.4M in Net Worth with Michael Alberse

    Generating passive income and generational wealth isn't always about finding the next big investment or coming up with a million-dollar business idea. In most cases, it's about making a series of intentional decisions with your money, building surplus income, and consistently putting it to work. That's what makes Michael Alberse's story so inspiring. Michael went from living in a self-built van while working as an Account Manager at Google to growing his net worth to $1.4M, creating multiple income streams that generate thousands of dollars in passive income every month. And most recently, Michael founded Trailmix Wealth, which helps everyday people build real wealth while enjoying the journey.​ Michael's journey is especially meaningful to me because reading The Lifestyle Investor was the launchpad that changed how he thought about investing. He eventually became one of the first members of our Foundations program and the first to make the jump into Tribe of Investors. In our conversation, Michael shares how he aggressively saved and invested early in his career, turned his Google Ads expertise into a cash-flowing business, and started building a diversified portfolio outside of the stock market. We also unpack some of his biggest wins and mistakes as an investor, the importance of learning from people further ahead of you, and why he's ultimately building wealth around the life he wants to live. In this episode, you’ll learn:  ✅ How creating surplus income and consistently reinvesting it can accelerate your path to financial freedom. ✅ Why Michael built a cash-flowing business that now requires only a few hours of his time each month. ✅ What Michael's biggest wins and losses in private investments taught him about deal structure and due diligence. Show Notes: LifestyleInvestor.com/310 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 FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  5. Sep 24

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

    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 FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  6. Sep 17

    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/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 FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  7. Sep 10

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

    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 FacebookYouTubeInstagramLinkedInTwitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  8. Sep 3

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

    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 FacebookYouTubeInstagramLinkedInTwitter 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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About

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 cash flow strategies. Justin’s principles enable you to move from an “earned income” career to support your lifestyle with passive cash flow investments including real estate, operating companies, debt, equity, and franchises that give you the absolute freedom to live the life you truly desire. Interviews with top thought leaders, such as, John Lee Dumas, Ryan Levesque, Hal Elrod, Jon Vroman, Mike Koenigs, Phillip Stutts, Rob Dial, John Ruhlin, Brad Johnson, Robert Glazer, Mike Michalowicz, Geoff Woods, Steve Sims, and many more! For more information, visit https://justindonald.com

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