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.

Private credit has been around for centuries, but in recent years, it has surged in popularity—especially among the world’s wealthiest investors. Family offices and institutional investors are shifting away from traditional fixed income and embracing private credit for higher returns, stronger downside protection, and better diversification.Today, I’m sitting down with Peter Sack, co-founder and partner at Chicago Atlantic, one of the largest private credit firms in the U.S. Chicago Atlantic has deployed over $2 billion in cannabis private credit alone, with additional investments in venture debt, digital infrastructure, and lower middle-market lending.In this conversation, Peter breaks down why private credit is booming, how it compares to traditional fixed income, and where the best opportunities exist today. If you’re looking to diversify your portfolio and invest like the ultra-wealthy, this episode is a must-listen.In this episode, you’ll learn:✅ Why family offices are increasing their allocation to private credit.✅ How private credit offers equity-like returns with lower risk.✅ The impact of rising interest rates on private lending—and why banks are failing to keep up.✅ How Chicago Atlantic structures private credit deals, including high-yield lending & equity kickers.Show Notes: LifestyleInvestor.com/229Tax 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.

Too many business owners wake up the day after selling their company with one regret: 'I could have gotten more.' The difference between an average exit and a life-changing one comes down to strategy—and today, we’re diving deep on how to get it right.I’m sitting down with Chad Morissette, an M&A expert who has advised on hundreds of business sales and helped founders maximize their exits. Unlike many advisors, Chad and his entire team have personally built and sold their own companies—meaning they actually understand what it takes to position a business for an optimal sale.In this conversation, Chad breaks down the most common mistakes sellers make, the factors that determine a company’s true value, and how to ensure you’re not leaving money on the table when it’s time to exit.Whether you’re years away from selling or already fielding offers, this episode will help you secure the best deal possible.In this episode, you’ll learn:✅ The #1 reason most founders regret their exit—and how to avoid it.✅ Why your company is probably worth less than you think—and how to change that.✅ The key factors buyers look for when valuing a business (it’s not just revenue).✅ Why working with an M&A advisor can mean millions more in your pocket.Show Notes: LifestyleInvestor.com/228Tax 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.

If you don’t have an assistant, you ARE the assistant.That’s the reality for most entrepreneurs—stuck handling emails, booking travel, and drowning in admin work instead of focusing on what actually grows the business.In this episode, I’m sitting down with Tricia Sciortino, CEO of BELAY—a staffing agency that specializes in hiring top-tier virtual executive assistants, bookkeepers, and other remote talent to help business owners buy back their time and scale faster.We’re talking all about how hiring the right executive assistant isn’t an expense—it’s the key to unlocking your next level of growth.Tricia started as the first-ever virtual assistant at BELAY and worked her way up to CEO—so she knows firsthand the impact of smart delegation. Before that, she was Michael Hyatt’s original EA, playing a key role in helping him scale what is now Full Focus, a multimillion-dollar leadership training company. She’s had a front-row seat to how top entrepreneurs leverage assistants to maximize productivity and growth—and today, she’s pulling back the curtain to share those insights with us.In this episode, you’ll learn:✅ Why NOT hiring an EA is actually costing you more—and how it’s limiting your business growth.✅ How AI is transforming the role of executive assistants—and how to use it to streamline operations, boost productivity, and scale faster.✅ A step-by-step framework to start delegating today, so you can focus on high-value activities and stop being your own assistant.Show Notes: LifestyleInvestor.com/227Tax 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.

In this discussion, Ben Reinberg, founder of a $500 million commercial real estate firm, shares his expert insights on building wealth through hard assets. He reveals the overlooked real estate asset class poised for significant opportunities in 2025. Ben recounts how he achieved a 3X return on investment and emphasizes leveraging relationships as a key strategy for success. Additionally, he highlights the power of passive investing and provides a blueprint from his book, illustrating how to thrive during economic challenges.

M.C. Laubscher, founder of Cashflow Ninja and author of "Get Wealthy for Sure," shares his expertise on alternative investments and financial freedom. He discusses why wealthy investors are shifting toward alternatives, revealing that family offices allocate up to 59% of their portfolios to these assets. Listeners learn essential strategies to shield wealth from inflation and taxes while navigating market volatility. M.C. emphasizes the importance of understanding different financial strategies, urging a fresh perspective on investing beyond traditional frameworks.

Bronson Hill, a former medical sales professional turned passive income investor, shares his incredible financial journey after interviewing over 2,500 millionaires. He reveals that building wealth begins with a mindset shift and the importance of surrounding oneself with successful people. Bronson discusses the hidden investment strategies the ultra-wealthy utilize, emphasizing alternative assets over traditional stocks. He also highlights common financial pitfalls and explains how to leverage inflation for financial independence.

Want to know where the smart money is going in 2025? Over $80 trillion is set to move from Baby Boomers to Millennials in the coming years, creating once-in-a-lifetime opportunities for those ready to capitalize. This week, the tables are turned—I’m the guest on Mike Koenigs’ podcast, Capability Amplifier, and we’re talking all about the biggest investment trends of 2025.We dive deep into overlooked opportunities like private credit, Web3 gaming, and the transformative potential of Bitcoin and AI. We also explore emerging trends such as border town real estate fueled by on-shoring, minority ownership in pro sports, and the untapped potential of distressed assets.I also share some of my biggest investing mistakes and how those experiences shaped the Lifestyle Investor philosophy that I teach today.If you're looking for high-value investment insights and a fresh perspective on wealth-building, this is an episode you don’t want to miss.In this episode, you’ll learn: ✅ The biggest investment opportunities for 2025—where smart money is going and how to capitalize on the largest wealth transfer in history.✅ How to spot “invisible deals”—and why the best investments aren’t found in the mainstream but through off-market opportunities few people know about.✅ Why Bitcoin, AI, and private credit are reshaping wealth creation—and how to position yourself ahead of the curve before the masses catch on.Show Notes: LifestyleInvestor.com/223Tax 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.