The Lifestyle Investor - Investing, Passive Income, Wealth

Justin Donald
  • 4.9 (285)
  • BUSINESS
  • UPDATED WEEKLY

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. 22H AGO

    278: From a Huge Exit To Reimaging IT & Cybersecurity with Bill Tyndall

    Businesses are implementing AI faster than most entrepreneurs realize. But the best opportunities aren’t always in cutting-edge startups. In many cases, the best returns are in legacy businesses that haven’t kept pace with the innovation curve. Understanding that gap—and how to close it—has defined the career of today’s guest. Bill Tyndall is the founder of Tynrose, a holding company focused on modernizing legacy businesses through digital transformation, data, cybersecurity, and AI. After launching Electric in 2016, which revolutionized IT support for SMBs, he had a huge exit with a billion-dollar valuation just four years later.   You’ll hear how Bill’s newest venture, Tynrose, builds platforms that don’t just implement technology; they reimagine it and help companies move beyond patchwork solutions and into scalable solutions that are built to last in the digital world. His approach challenges outdated models and reframes what’s possible when businesses stabilize their technology, leverage clean data, and deploy AI with intention. In this episode, you’ll learn:  ✅ How SMBs and legacy businesses may offer better AI-driven returns than tech startups. ✅ Why Bill decided to start a new business after his billion-dollar exit, and what creating a legacy with his businesses means to him.  ✅ Why AI is really just a capacity expander for humans and what the future holds for IT and cybersecurity in an AI-driven world. Show Notes: LifestyleInvestor.com/278 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.

    51 min

  2. FEB 12

    277: The Mindset Shift That Unlocks True Wealth and Freedom with Pablo Della

    Most entrepreneurs believe once they achieve financial success or have the big exit, freedom, fulfillment, and happiness will follow. It’s a trap. And today’s guest learned that the hard way. On today's pod, I'm talking with Pablo Della, an 8-figure founder who went from growing up poor in Argentina to scaling his business into a major consumer brand. From the outside, it looked like he had won. But after the financial success came a deeper question: Now what? In this conversation, Pablo shares what changed after the money stopped being the goal, and how he rebuilt his life around real freedom. He’s also just launched a new show, Freedom Flip, where he and his co-host publicly challenge conventional thinking around money, identity, and achievement. Go give it a follow RIGHT HERE! In this episode, you’ll learn:  ✅ Why Pablo believes that spending money on experiences generate a real return on happiness, time, and quality of life that goes beyond ROI. ✅ How Pablo evaluates the true cost-benefit of flying private—and why the math looks different once you factor in time, energy, and opportunity cost. ✅ Why Pablo believes inflation isn’t accidental, and how that belief shapes his long-term view on money, Bitcoin and wealth. Show Notes: LifestyleInvestor.com/277 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.

    1h 43m

  3. FEB 5

    276: Why Hiring a Tax Strategist Is The Best Investment You’ll Ever Make with Karlton Dennis

    Believe it or not, income taxes can become the biggest expense for entrepreneurs. Yet most people approach tax planning reactively, missing powerful opportunities hiding in plain sight. Today’s guest helps investors get ahead of the game by treating tax strategy not as compliance, but as one of the most important wealth-building tools available. Karlton Dennis is one of the leading tax strategists in the country and the founder of Tax Alchemy. Through his work with high-earning entrepreneurs, he helps clients legally reduce taxes, increase cash flow, and reinvest capital intentionally rather than giving it away unnecessarily. In our conversation, Karlton breaks down why proactive tax planning often delivers higher returns than any investment deal—and how understanding the tax code allows you to keep more money working for you, with more investment opportunities, year after year. In this episode, you’ll learn:  ✅ Why investing in world-class tax strategy can outperform real estate, private equity, and traditional investments. ✅ The most common tax preparation mistakes that cost business owners tens of thousands per year. ✅ Which tax strategies attract IRS scrutiny and how to use the tax code to your advantage without crossing red lines. Show Notes: LifestyleInvestor.com/276 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.

    42 min

  4. JAN 29

    275: Building Passive Income Through Real Estate and Strategic Partnerships with Cory Jacobson and Ryan Bevilacqua

    For many professionals, the traditional path of investing in 401(k)s and IRAs and waiting until their retirement date, while trading time for money, eventually raises a difficult question: Is there a better way? Today’s guests discovered that by leveraging real estate and strategic relationships, they could build passive income while enjoying the perks of their 9-5 jobs and now teach others to do the same. Rather than chasing shortcuts, they focused on building a foundation that created options using hidden wealth hacks and money habits self-made millionaires use. Cory Jacobson and Ryan Bevilacqua are real estate investors, entrepreneurs, and hosts of the Wealth Juice Podcast. Through strategic partnerships and documenting their journey publicly, they’ve built a growing real estate portfolio while helping others take their first steps toward passive income and financial independence. Cory and Ryan unpacked the mindset shifts, relationship strategies, and long-term thinking that helped them move from early investments to scalable opportunities—while staying aligned with their purpose, lifestyle, and financial freedom goals. In this episode, you’ll learn:  ✅ Why financial freedom is less about early retirement and more about creating optionality. ✅ How strategic partnerships, masterminds, and relationships accelerate growth faster than trying to do it on your own. ✅ Why building in public creates leverage, credibility, and unexpected opportunities. Show Notes: LifestyleInvestor.com/275 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.

    44 min

  5. JAN 22

    274: How Financial Literacy Unlocks Financial Freedom and Generational Wealth with Sharon Lechter

    For many entrepreneurs and investors, financial success often feels harder than it should. Despite tireless work and long hours spent chasing income, they still end up owing a business that runs them rather than the other way around. Today’s guest has spent decades helping people break that cycle by shifting how they think about money, assets, and financial freedom itself. Sharon Lechter is a globally recognized financial literacy expert, former CPA, keynote speaker, and five-time New York Times bestselling author. She is best known as the co-author of Rich Dad Poor Dad and 14 additional books in the Rich Dad series, including the transformational Cashflow Quadrant. She’s also co-authored many other influential books, including Exit Rich, Three Feet from Gold, and Think and Grow Rich for Women. Sharon has dedicated her career to educating and empowering investors at any level, helping them move from earned income to asset-driven wealth while reclaiming their time. In her newest book, Old Wealth, New Wealth, True Wealth, Sharon offers readers both an inspiring fable and a practical blueprint for crafting a legacy that lasts. In this episode, you’ll learn:  ✅ Why the purest definition of financial freedom is when asset income exceeds your monthly expenses. ✅ How the Cashflow Quadrant was a game changer for Justin and helps entrepreneurs reclaim time and scale faster by making better decisions. ✅ Why Sharon’s newest mission with IQ Hall helps creators and entrepreneurs maintain ownership and protect their intellectual property while using AI. Show Notes: LifestyleInvestor.com/274 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.

    44 min

  6. JAN 15

    273: Using Land Flipping to Create Passive Income and Lifestyle Freedom with Jack Bosch

    Building lasting wealth isn’t just about making money—it’s about designing a system that creates freedom, flexibility, and long-term security. And today’s guest is a real estate entrepreneur who has mastered the art of turning land deals into a powerful cash-generating engine that fuels both lifestyle and legacy. Jack Bosch is a seasoned real estate investor who has flipped over 4,000 land deals and helped hundreds of entrepreneurs build scalable, location-independent businesses. Alongside his wife Michelle, Jack has built land flipping into a high-leverage “cash machine” that funds long-term investments, passive income, and true lifestyle freedom. If you’re looking for a practical framework to move beyond the earn-and-spend cycle and build income that supports life on your terms, this conversation delivers. In this episode, you’ll learn:  ✅ Why land flipping can be a simpler and more flexible entry point into real estate than traditional investments ✅ Jack’s method for finding deeply discounted land deals that can often be flipped in a very short period of time.   ✅ How Jack’s Forever Cash framework turns active income into lasting passive income and wealth. Show Notes: LifestyleInvestor.com/273 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.

    49 min

  7. JAN 8

    272: The Power of Hosting Epic Events to Curate Relationships & Accelerate Wealth with Thanh Pham

    Building wealth and time freedom isn’t just about working harder or finding the next opportunity; it’s about surrounding yourself with the right people and designing systems that create leverage over time. And today’s guest has mastered both sides of that equation. Thanh Pham is the founder of Asian Efficiency and host of The Productivity Show, where he has spent more than a decade helping entrepreneurs and executives work smarter, not longer. From hosting 50 magnificently curated Jeffersonian-style dinners to building thriving communities and events in Austin, Thanh has mastered the art of creating relationship capital.  Thanh shares how curating meaningful relationships not only accelerated his personal growth but also his business opportunities and his lifestyle freedom. He explains why hosting experiences is one of the fastest ways to build trust and credibility and how positioning yourself as a connector opens doors that money can’t. You definitely won’t want to miss the end of our conversation, where Thanh explains how he’s now leveraging AI and automation, using AI agents to handle entire workflows and reclaim dozens of hours of his time each week. Rather than replacing human connection, Thanh shows how technology can amplify it and free up your time for what matters most. In this episode, you’ll learn:  ✅ How hosting intentionally curated events positions you as a connector and builds trust, develops opportunities and accelerates long-term wealth. ✅ How Thanh curates relationship capital to grow his business without sacrificing freedom or burning out. ✅ The AI agents Thanh uses to automate various aspects of his business and the system that saved him 83 hours in a single week. Show Notes: LifestyleInvestor.com/272 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.

    41 min

  8. JAN 1

    271: How Live Challenges Created Predictable Cash Flow and $100M+ in Revenue with Pedro Adao

    Every entrepreneur wants a business that generates consistent, predictable cash flow. But most end up pouring time and money into typical marketing strategies, only to be left with frustration and inconsistent results instead of passive income and revenue. But today’s guest has unlocked a cheat code that has generated millions in revenue without using paid ads and typical marketing strategies. Pedro Adao is an 8-figure Kingdom Entrepreneur, best-selling author, and founder of multiple ventures who has pioneered a highly effective business model centered on free & paid challenges that has generated over $100 million in revenue for himself and his clients. His expertise has impacted tens of thousands of entrepreneurs worldwide and helped countless individuals achieve levels of success they could only have dreamed of. Pedro has worked with many industry icons, including Russell Brunson, Dean Graziosi, and Daymond John (to name a few), who recognized this approach as a game-changer for entrepreneurs. In our conversation, Pedro shares how he built his challenge framework, why his “taste and see” marketing approach outperforms traditional marketing funnels, and how challenges create low-risk, high-leverage cash flow for entrepreneurs and businesses of all sizes.  P.S. Pedro is kicking off the new year with a 31 Day Wisdom Challenge starting on January 1st, 2026. It’s completely free to join, you’ll hear from some amazing guests on a daily journey that over 350,000 people from over 100 countries have experienced. You can sign up by clicking here. In this episode, you’ll learn:  ✅ Why live challenges are so effective at creating predictable cash flow with minimal overhead. ✅ How Pedro lost everything after the 2008 crisis and how his faith helped him rebuild from rock bottom to the leading expert he is today. ✅ How traditional wealth management and investing in the stock market could mean taking on more risk than ever in the year ahead. Show Notes: LifestyleInvestor.com/271 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.

    1h 10m
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4.9
out of 5
285 Ratings

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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