The Lifestyle Investor - Investing, Passive Income, Wealth

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.

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.