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

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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

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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

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Rate & Review

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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

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Rate & Review

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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

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Rate & Review

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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

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Rate & Review

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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

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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

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Rate & Review

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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

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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.

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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.