Afleveringen
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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/239
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
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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/238
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
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Zijn er afleveringen die ontbreken?
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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/237
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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What if every decision you made was actually predetermined, shaped by a story your nervous system wrote years ago?
Well, the science suggests that our emotional programming starts in the womb.
Today’s guest calls it the “ghost in the machine” and has spent 20+ years helping people rewrite it.
In this episode, I’m talking with Joey Klein—Founder of Inner Matrix Systems and a globally recognized transformation expert. Joey has trained over 84,000 people, from Fortune 500 execs to pro athletes, to rewire the emotional and mental patterns quietly shaping their behavior. His work blends neuroscience, psychology, and mindfulness to create real, lasting change from the inside out.
Together, we explore how these subconscious imprints silently drive your decisions—often sabotaging success in business, relationships, and everyday life.
If you want to rewire your inner programming, get unstuck, and create meaningful success in every area of life, you’re going to love this episode.
In this episode, you’ll learn:
✅ How a near-death experience at 19 launched Joey's journey into inner work—and why emotional mastery, not hustle, is the key to lasting success.
✅ What the “ghost in the machine” really is—and how subconscious emotional imprinting silently drives your decisions.
✅ How Joey helped a top Hollywood executive break through years of creative roadblocks by rewiring his internal belief system.
✅ Why your nervous system is just as trainable as your muscles—and how to strengthen it to access clarity, calm, and peak performance.
Show Notes: LifestyleInvestor.com/236
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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 fast
Most 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 it
You’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 company
When 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/235
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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If you're grinding through life just to someday 'retire,' you're doing it wrong.
Today, I’m talking with Garrett Gunderson—a best-selling author, speaker, and financial disruptor—about what it really takes to build freedom now, not 30 years down the road.
Garrett’s helped thousands of entrepreneurs grow their wealth without sacrificing their lifestyle. He’s trained top financial professionals, revived the timeless wealth principles of the Rockefellers, and developed practical frameworks that simplify the money game—so you can build wealth on your terms.
In this episode, we break down what Garrett calls The Trifecta—a proven system for becoming financially fit, reaching true independence, and unlocking a level of freedom that's only possible when you change the way you think, not just the way you invest.
In this episode, you’ll learn:
✅ How to use whole life insurance, trusts, and asset protection to build generational wealth like the Rockefellers.
✅ Why true financial independence starts in your mind—not your bank account.
✅ Garrett’s Trifecta Framework for building wealth, protecting assets, and creating true freedom.
Show Notes: LifestyleInvestor.com/234
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/233
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/232
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/231
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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So you’ve sold your business—what’s your next step?
Most entrepreneurs spend years building their businesses, but when they finally exit, they struggle to transition from managing staff and emails to all the investing opportunities they now have.
In today’s episode, I’m sitting down with Dr. Tony Jacob—an entrepreneur who scaled and exited the largest private optometry roll-up in Texas history. After his exit, Tony faced the challenge of shifting from business owner to capital allocator, learning firsthand the risks of rushing into investments, the importance of patience, and how to structure a family office for long-term wealth preservation.
We’re diving into how to avoid the common pitfalls of post-exit investing, how to build a bulletproof asset allocation strategy, and the growing role of Bitcoin in family office portfolios.
If you’re an entrepreneur preparing for an exit—or you’ve already sold and want to make smarter financial decisions—this episode is a must-listen.
In this episode, you’ll learn:
The biggest investing mistakes post-exit entrepreneurs make—and how to avoid them.Why capital preservation is just as important as wealth creation—and how to structure your portfolio to last generations.Why Bitcoin is becoming a strategic asset for family offices and institutional investors.Show Notes: LifestyleInvestor.com/230
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/229
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/228
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/227
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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If you want to build long-term wealth and protect your money from market volatility, today’s guest has the tools to show you how to do it by using hard assets and smart investing strategies.
Ben Reinberg, is one of the leading experts in commercial real estate and the founder of Alliance Consolidated Group, a firm he built from scratch to become a $500M empire that has managed billions in transactions across medical offices, industrial, and multifamily real estate. In his newest book, Hard Assets and Hard Money for Hard Times, he lays the blueprint for building a hard asset empire.
With over 30 years of experience, Ben explains why real estate is the best vehicle for building wealth, how to invest passively by focusing on your niche, and why leveraging relationships is the key to long-term success.
Whether you're an experienced investor or just starting out, this episode is packed with invaluable insights that can help you grow and protect your wealth.
In this episode, you’ll learn:
✅ The one real estate asset class that will have the biggest opportunities in 2025—and why most investors are overlooking it.
✅ How Ben turned a single deal into a 3X return—and the investing strategy he still swears by today.
✅ The 3 most powerful wealth levers you can use to scale your investments faster—with less of your own money.
Show Notes: LifestyleInvestor.com/226
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
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Are you stuck in the Wall Street mindset and looking for better ways to grow and protect your wealth?
In this episode, I’m sitting down with M.C. Laubscher, founder of Cashflow Ninja and author of Get Wealthy for Sure: The #1 Financial Strategy for Business Owners to Multiply Wealth Predictably. M.C. is an expert in alternative investments, teaching entrepreneurs how to think outside the traditional financial box to create lasting financial freedom.
We dive into why alternative investments outperform traditional options, how to shield your wealth from inflation and taxes, and why understanding the difference between saving, investing, speculating, and gambling is critical to your financial success.
Whether you’re new to alternative investing or a seasoned investor looking to refine your strategy, this conversation is packed with insights to help you thrive in uncertain markets.
In this episode, you’ll learn:
✅ Why family offices allocate up to 59% of their portfolios to alternative investments
✅ How to navigate inflation, market volatility, and tax threats with defensive strategies
✅ The power of inefficient markets and the asymmetric opportunities they offer
✅ How to create a “sleep-well-at-night” cash strategy while still capitalizing on investment opportunities
Show Notes: LifestyleInvestor.com/225
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Building wealth isn’t just about what you do—it’s about how you think. And the ultra-wealthy know that financial success starts in the mind.
That’s exactly what today’s guest, Bronson Hill, discovered after interviewing over 2,500 millionaires. Through those conversations, he uncovered the habits, mindsets, and investment strategies that separate everyday earners from those who achieve true financial freedom.
A former medical sales professional, Bronson walked away from a high-paying career to pursue passive income, scaling his wealth 20X in just a few years. Bronson is a general partner in 2,500 multifamily units worth over $250M, and has personally raised over $45M for real estate and private equity deals.
In this episode, we dive deep into the psychology of wealth, why who you surround yourself with determines your financial future, and the hidden investment strategies the ultra-wealthy use to build lasting fortunes.
In this episode, you’ll learn:
✅ The mindset shift that helped Bronson 20X his net worth—and the surprising reason most people stay broke.
✅ How 2,500 millionaires built their wealth—and the biggest investing mistakes to avoid.
✅ The investment strategy ultra-wealthy investors use to outperform the stock market.
✅ The hidden “Wealth-Worthiness” belief that silently holds most people back from financial freedom.
Show Notes: LifestyleInvestor.com/224
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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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/223
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Imagine having a team of expert researchers, marketers, and strategists at your fingertips—working 24/7 to grow your business. That’s the power of AI. And the entrepreneurs who master it will outlearn, outperform, and out-earn everyone else.
In this episode, I’m talking with Mike Koenigs—a serial entrepreneur, 19-time bestselling author, pioneer in digital marketing, and AI expert—who is breaking down exactly how smart entrepreneurs are leveraging AI to scale faster, automate success, and build wealth on autopilot.
Mike walks us through the exact tools and frameworks he’s using to grow businesses, streamline marketing, and uncover new opportunities with AI. He does a lot of screen sharing and demos, so this is definitely an episode you’ll want to check out on YouTube.
If you’re looking to gain an edge in 2025 and beyond, this episode is packed with practical, step-by-step strategies to help you integrate AI into your business and wealth-building strategy.
BTW, Mike dives deep with live screen shares and real-time demos, making this a must-watch episode on YouTube.
Giveaways
The AI Accelerator Book + Videos (Free)
Learn how to 10x your productivity, clone your smartest employees, and monetize your IP in the new AI economy. Mike’s giving away a digital copy of his book, AI Accelerator. To gain access, CLICK HERE.
Your Next Act Book + Videos (Free)
The 6 growth Accelerators for creating a business you'll love for the rest of your life. To gain access, CLICK HERE.
Show Notes: LifestyleInvestor.com/222
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee 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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Most entrepreneurs believe growth requires sacrificing everything else. Jonathan Goodman proves you can scale a business without giving up your freedom.
He’s built multiple companies, written 12 books (including The Obvious Choice), and scaled coaching businesses to 7-figures—all while spending half the year living abroad with his family.
How? By mastering the art of incentives, knowing when to not scale, and investing in cash-flowing assets that work harder than he does.
In today’s episode, we break down the wealth-building strategies Jonathan used to scale a business to $35M+ in revenue.
We explore why most investments fail to beat the returns generated by a well-run business, a leveraged personal brand, or an asymmetric bet like Bitcoin.
Jonathan also shares how he structures his businesses to maximize freedom and avoid the common pitfalls of scaling.
If you’re looking for a playbook on building wealth, designing a business that doesn’t take over your life, and making sure your money works for you—not the other way around—this episode has the answers.
In this episode, you’ll learn:
✅ Jonathan’s “whales and minnows” framework for eliminating 80% of your workload—why most entrepreneurs waste time on tasks that don’t move the needle, and how Jonathan ensures every hour works for him.
✅ The “eight-four rule” of seasonal living—how Jonathan avoids burnout and stays at peak performance by alternating between intense work sprints and extended time off.
✅ How to design scalable compensation systems that turn employees into partners—the secret to building a team that’s as invested in success as you are, without micromanaging.
Show Notes: LifestyleInvestor.com/221
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Ever feel like the tax system is stacked against you? In this episode, I’m talking with cost segregation expert Wes Mabry to uncover one of the most underutilized and powerful tax strategies available to real estate investors – a proven method to accelerate depreciation, defer taxes, and increase cash flow.
Wes is the Founder of 1245 Consulting and one of the country’s leading authorities on cost segregation. For over 17 years, Wes and his team have helped investors—from small-time landlords to ultra-high-net-worth individuals—save over $2 billion in taxes.
In our conversation, Wes breaks down cost segregation step-by-step: what it is, how it works, why it’s so powerful, and the types of properties that benefit the most. He shares insights on everything from accelerating depreciation on assets like flooring and gas lines to why car washes and mobile home parks offer some of the best opportunities.
You’ll also learn about bonus depreciation, strategies to handle recapture taxes, and smart moves like retroactive studies and 1031 exchanges.
In this episode, you’ll learn:
✅ How cost segregation accelerates depreciation by breaking down property components like landscaping, gas lines, and specialized flooring—helping you offset income without cutting into cash flow.
✅ Why asset classes like car washes and mobile home parks are tax goldmines, offering bigger savings than options like condos, self-storage or warehouses.
✅ How retroactive cost segregation can help you reclaim missed tax benefits and significantly reduce your taxable income.
Show Notes: LifestyleInvestor.com/220
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
FacebookYouTubeInstagramLinkedInTwitterSee 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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