The Lifestyle Investor - Investing, Passive Income, Wealth

Every founder dreams of the big exit. But few are prepared for what comes next.Today’s guest learned the hard way. Anastasia Koroleva sold her company for 9-figures, but instead of feeling free, everything got more complicated.She lost her identity. Made costly investment mistakes. And her marriage broke under the weight of post-exit stress.In this honest conversation, Anastasia opens up about the emotional aftermath of selling a business and the hidden challenges that come with sudden wealth.You’ll learn why wealth often brings confusion instead of clarity, how overconfidence leads to poor investment decisions, and the patterns she’s uncovered from interviewing hundreds of founders after they’ve successfully exited their business.If you're building toward an exit — or learning how to invest after one — this is the conversation most people wish they’d heard sooner.In this episode, you’ll learn: ✅Why financial freedom doesn’t always equal happiness—and the steps you can take to avoid feeling of emptiness post-exit.✅How to avoid common post-exit mistakes of investing in VC or angel investing without proper due diligence.✅The benefits of raising children who aren’t entitled and teaching them about taking risks, the benefits of entrepreneurship and not being afraid to fail.Show Notes: LifestyleInvestor.com/239Tax 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.

Imagine that you're an entrepreneur who's already had an exit. You're working on a Master's degree at MIT's Entrepreneur Program, and then you get a call from a talent scout at Shark Tank.Not only that, but that phone call landed you a million-dollar investment from the Sharks for your restaurant business (still one of the top five deals ever to this day) and a seven-figure exit a few years later.That's just scratching the surface of why I'm excited to introduce you to my friend Yuen Yung. Yuen is a serial entrepreneur, investor, and the Co-Founder of HalBar Partners, a niche private equity firm specializing in a relatively unknown but powerful asset class: Search Funds.In our conversation, you'll hear the experience Yuen has gained from having several successful exists, why he believes that alternative investments and real estate offer better ROI and security than the public markets, and why his newest venture into search funds—an asset class averaging a 35% IRR—could be a game-changer for investors seeking higher multiples with the steady returns of private equity.In this episode, you’ll learn: 1.) Why traditional stock market investing with 60/40 portfolios feels outdated—and why the ultra-wealthy are investing their money in alternative investments.2.) What Search Funds are and why this niche asset class differs from the more common private equity and venture capital investment opportunities—and why most people have never heard of them.3.) How Yuen earned a $1 million dollar investment on Shark Tank, despite initially turning down the opportunity and how he turned it into a 7-figure exit.Show Notes: LifestyleInvestor.com/238Tax 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.

Imagine signing a $10M contract, only to see $2M after taxes, fees, and cuts?That’s the reality for most pro athletes. And for many, it’s just the beginning of financial missteps that can lead to bankruptcy just a few years after retiring.Today’s guest is Tom Zheng—a former NFL sports scientist turned investor. He’s also the Co-Founder & CEO of The Players Company, a platform helping professional athletes build real wealth through education, access, and smart investments.In this episode, Tom shares a behind-the-scenes look at how professional athletes are financially coached (or often misled), the growing role of private equity in sports, and how he’s guiding athletes toward smarter financial futures through education and access to exclusive investment opportunities.Whether you’re a sports fan, investor, or entrepreneur, this episode is packed with lessons about leverage, legacy, and building financial intelligence. In this episode, you’ll learn: 1.) How Tom went from NFL sports science to investing in pro teams and building a player-owned private equity firm.2.) The financial traps most pro athletes fall into—and how The Players Company is solving them.3.) Why investing in sports teams and NIL assets isn’t just for billionaires anymore—and what this means for everyday investors.Show Notes: LifestyleInvestor.com/237Tax 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.

Joey Klein, the Founder of Inner Matrix Systems and a leading transformation expert, shares his insights on reprogramming emotional patterns that shape our lives. He explains how a near-death experience at 19 motivated him to explore emotional mastery as the key to success. Joey discusses the concept of the 'ghost in the machine,' highlighting how subconscious imprints influence our decisions. His practical techniques help individuals break through barriers and strengthen their mental resilience, offering a pathway to a more fulfilling life.

Most people run from problems. Preston Brown builds businesses around them.He believes every sale is simply a solution to a problem—and if you can solve enough of them, you can build real wealth without sacrificing your time, health, or freedom.Preston is a prolific entrepreneur and systems thinker who automates, optimizes, and scales companies across real estate, lending, construction, and service industries. He’s built a 9-figure portfolio of cash-flowing businesses by identifying everyday frustrations and turning them into opportunities through strong systems and self-managed teams.In this episode, you’ll learn how Preston structures his businesses so they don’t depend on him to operate, how to spot hidden profit leaks in your operations, and how to turn recurring problems into scalable income streams—all while freeing up your time to focus on what matters most.In this episode, you’ll learn: 1.) The “4 Flows of Capacity” framework that fixes broken businesses fastMost business owners don’t know where they’re bleeding time, money, or energy. Preston shares his simple but powerful system—Leads, Sales, Delivery, Cash—and how identifying the weakest link in these flows can unlock exponential growth.2.) Why Return on Time (ROT) is the new ROI—and how to design your business around itYou’ll learn how Preston optimizes for time freedom, not just profit—and how applying ROT, ROM (Return on Marketing), and ROE (Return on Emotion) has helped him build a business portfolio that supports his lifestyle, not consumes it.3.) How he turned a $12M lawsuit into the best thing that ever happened to his companyWhen a shady developer put Preston’s real estate empire at risk, he could’ve folded. Instead, he went public, led with integrity, and earned even more trust from banks and partners—proving that doing the right thing when no one’s looking is the ultimate business strategy.Show Notes: LifestyleInvestor.com/235Tax 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.

Garrett Gunderson, a best-selling author and financial disruptor, shares insights on achieving true financial freedom without sacrificing your lifestyle. He introduces his Trifecta Framework, emphasizing that financial independence begins in your mind. Topics include innovative strategies like whole life insurance for wealth building, the importance of passive income over simple wealth accumulation, and the value of community and education in financial journeys. Discover how to align your values with sustainable wealth creation!

Most people lose money in real estate syndications for one reason: they don’t know how to properly vet a deal.In this episode, I sit down with Hans Box to unpack the exact questions savvy investors should ask before wiring funds to a sponsor.Hans is the Co-Founder of Box Wilson Equity, which has invested has invested $95MM+ in equity across various asset classes, including multifamily, self-storage, mobile home parks, distressed debt, office, and preferred equity. And he’s personally been involved in the acquisition, investment, and management of over $350MM in multifamily and self-storage assets.Together, we break down how to assess risk, spot red flags in offering documents, and why alignment, transparency, and track record matter more than hype or projected returns.Whether you’re considering your first deal or refining your due diligence process, this conversation will help you make smarter, safer investment decisions in the world of syndications. In this episode, you’ll learn:  1.) The #1 reason investors lose money in syndications—and how to avoid it by reverse-engineering a deal’s risk through the capital stack, pro forma, loan terms, and sensitivity analysis. 2.) Why “projected returns” are a trap—and what smart investors look at instead, including sponsor alignment, track record, deal structure, and the questions that reveal the truth before you wire a dollar. 3.) The hidden red flags most investors miss inside the fine print, from manager replacement clauses to preferred equity terms—and how reading between the lines of the PPM could save you from disaster.Show Notes: LifestyleInvestor.com/233Tax 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.

Whole Life Insurance is widely misunderstood, yet for billionaires and family offices, it’s a powerful tool for long-term financial security.While most people see life insurance as an expense, the wealthy use Whole Life Insurance as a financial foundation—one that offers liquidity, tax-free growth, and a guaranteed rate of return.In this episode, Caleb Guilliams, founder of BetterWealth, joins me to break down the real benefits of Whole Life Insurance—and how to use it the way the wealthy do.We discuss why most policies are structured incorrectly, the biggest mistakes to avoid, and why banks and billionaires hold massive amounts of Whole Life Insurance as part of their asset allocation strategy. In This Episode, You’ll Learn:1.) Why Whole Life Insurance isn’t an investment—and how the wealthy use it to build lasting financial security.2.) The truth about Whole Life Insurance—the key benefits, hidden pitfalls, and the biggest misconceptions that trip people up.3.) The costly mistakes people make when setting up a Whole Life policy—and how to structure yours for maximum flexibility and returns.Show Notes: LifestyleInvestor.com/232Tax 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.

Most pro athletes go broke after retiring. Devon Kennard isn’t one of them.As an NFL linebacker turned real estate investor, Devon made the rare transition from W-2 income to building an 8-figure real estate portfolio—all while still playing in the league. Seeing how easily athletes could be replaced, he knew he needed a plan for financial independence before his playing days were over. While many players burn through their earnings, Devon took a different approach, learning to invest, creating passive income, and setting himself up for long-term wealth.In this conversation, Devon breaks down how he navigated the world of investing while maintaining a demanding career in professional sports. He shares the biggest financial mistakes athletes (and high-income earners) make, why most people are underestimating their risk of being replaced, and how he built a diversified investment strategy that generates cash flow without requiring his constant attention. Devon also explains the mindset shifts that helped him overcome financial setbacks and why learning from other people's mistakes is the fastest way to accelerate wealth.In this episode, you’ll learn: 1.) The biggest money traps that cause pro athletes and high-income earners to go broke, and the simple shifts that can keep you financially free for life.2.) The 4 real estate strategies that helped Devon build an 8-figure portfolio while playing in the NFL—including the red flags to look for when vetting deals. 3.) How Devon escaped the W-2 paycheck cycle and built passive income while still working—and why waiting too long to start could be your biggest financial mistake.Show Notes: LifestyleInvestor.com/231Tax 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.

Dr. Tony Jacob, who successfully scaled and exited the largest private optometry business in Texas, shares his journey from entrepreneur to investor. He discusses the pitfalls many face after selling a business, emphasizing patience and informed decision-making. Listeners will learn about constructing a family office for long-term wealth, the intricacies of diversifying an investment portfolio, and why Bitcoin is gaining traction in modern asset strategies. This conversation is essential for anyone navigating the financial landscape post-exit.