The Lifestyle Investor - Investing, Passive Income, Wealth

Today, we’re switching things up. This episode isn’t about money. It’s about meaning. And someone who knows a lot about that subject is Matt Earl Beesley, who turned a childhood love of film into a decades-long directing career—and is now channeling that experience into a passion project with a powerful message, all while building a life and career on his terms.

Matt Earl is a Hollywood director whose credits include Braveheart, National Lampoon’s Christmas Vacation, CSI: Miami, Criminal Minds, Bosch, The Closer, and Chicago Fire, just to name a few. He’s worked side-by-side with legends like Clint Eastwood and Steven Spielberg. But beneath the glamorous résumé is a down-to-earth family man who chose passion over prestige and lifestyle over burnout.

In this conversation, Matt Earl shares how he broke into one of the most competitive industries in the world, the mindset that carried him from minimum wage intern to top-tier director, and why collaboration—not ego—is the secret weapon of success.

He also opens up about his new film project set in Texas—one that blends family, integrity, and the emotional complexity of immigration. 

If you’ve ever wondered whether you can pursue your craft, make a difference, and still live life on your terms—this episode is your inspiration.

In this episode, you’ll learn: 

1.) The secret to getting your foot in the door—even when everyone tells you your dream is impossible.

2.) The mindset shift Matt Earl learned from Clint Eastwood that transformed his approach to leadership and creativity.

3.) Why now might be the best time to invest in indie films—and how Matt Earl’s new movie gives investors a shot at doing good and doing well.

Show Notes: LifestyleInvestor.com/246

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

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What if you could cash out of any asset—without paying capital gains tax—and use the full value to create lasting financial freedom?

That’s exactly what Brett Swarts helps high-net-worth entrepreneurs and investors do every day—using the Deferred Sales Trust (which is what today’s episode is all about).

Brett is the Founder and CEO of Capital Gains Tax Solutions, a firm that’s closed over $500 million in Deferred Sales Trust and commercial real estate transactions. As a DST Trustee and expert in capital gains tax deferral, Brett equips clients and advisors with proven strategies to defer millions in taxes on the sale of highly appreciated assets.

While 1031 exchanges and Delaware Statutory Trusts serve a purpose, they often come with rigid rules, long lock-up periods, and limited flexibility. The Deferred Sales Trust, on the other hand, unlocks what most investors really want: tax deferral, liquidity, diversification, and the freedom to reinvest in nearly any asset.

Whether you're selling real estate, a business, crypto, or any other asset, this conversation could save you millions in taxes, so you won’t want to miss it. 

In this episode, you’ll learn: 

1.) How the Deferred Sales Trust works—and how it lets you legally defer capital gains, income, and estate taxes.

2.) The hidden downsides of 1031 exchanges and Delaware Trusts—and why many investors are moving to a more flexible strategy.

3.) How to reset your depreciation schedule after a sale to boost cash flow and reduce future taxes—without the pressure of like-kind rules.

Show Notes: LifestyleInvestor.com/245

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

You set out to build wealth, then realized your family was getting the leftovers.

But it doesn’t have to be either-or, you can thrive in both.

Today, I’m talking with Chad Willardson—wealth advisor to 8 & 9-figure founders, serial entrepreneur, bestselling author, and father of five—who’s figured out how to scale his wealth and stay fully present for his family. He runs a successful wealth advisory firm, owns multiple businesses, travels by private jet, and still makes it to his kids’ games.

In this conversation, Chad reveals the exact frameworks he uses to buy back time, build lasting wealth, and prioritize what matters most—insights he expands on in his upcoming book, Fully Invested: Why Work-Life Balance Is a Total Lie.

You’ll learn how he structures investments, leverages debt without stress, and designs a calendar around his life, not just his work.

In this episode, you’ll learn: 

1.) The habits and systems Chad uses to prioritize family without sacrificing growth

2.) The “buy, borrow, die” strategy that Chad uses to grow his wealth tax-free

3.) The real cost (and benefit) of buying a private jet

4.) The “Right Brain / Left Brain” executive assistant system that saved his time and sanity

Show Notes: LifestyleInvestor.com/244

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.

What if you could tap into the exact investment strategies billionaires use to multiply their wealth—without being one?

In this episode, I’m joined by Richard Wilson, founder of the Family Office Club and Billionaires.com. Over the last 18 years, Richard has analyzed over 1,000 billionaire strategies, advised more than 250 family offices, and built the world’s largest network of ultra-wealthy investors.

Today, he’s sharing what he’s learned from nearly two decades studying how the ultra-wealthy think, invest, and structure deals. From mental models and niche investing to AI-powered tools and negotiation tactics, you’ll discover the exact strategies billionaires use—and how to apply them to grow your own wealth, no matter where you're starting.

In this episode, you’ll learn: 

1.) How Richard built the #1 investor club for billionaires—and the exact mental models he’s seen them use to spot better deals and scale with precision.

2.) What he’s learned from interviewing hundreds of billionaires and centi-millionaires—including insights from Tony Robbins, Mark Cuban, Kevin Harrington, and many others.

3.) How to leverage AI to amplify your investment returns, streamline deal sourcing, and gain a competitive edge.

Show Notes: LifestyleInvestor.com/243

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.

Most people are chasing a retirement plan they’ll never enjoy – or even want. Derek Coburn is here to show you a more meaningful path that doesn’t require you to escape your life to start enjoying it.

Derek is a best-selling author, founder of the Cadre mastermind, and a former financial advisor to ultra-wealthy clients. After 20+ years in the industry, he sold his firm, walked away from the grind, and redefined what true financial freedom looks like.

 In this episode, Derek breaks down why the traditional model of retirement is outdated, inefficient, and in some cases, dangerously misleading. We explore smarter tax strategies the wealthy use to future-proof their income, the rising wave of “unretirement,” and why fulfillment doesn’t come from chasing a number… but from showing up with purpose.

 He also shares the story behind his newly released book, Let’s Retire Retirement, and reveals the $50,000 mindset shift that transformed how he shows up as a father, a leader, and a man of faith.

In this episode, you’ll learn:

1.) Why 1 in 3 retirees return to work – and how to design a life you never want to retire from instead.

2.) The hidden risks of 401(k)s – plus the tax strategies wealthy investors are using to protect their future income.

3.) The time machine exercise that redefined Derek’s relationship with time, money, and fatherhood – and how you can create special moments in your own life.

Show Notes: LifestyleInvestor.com/242

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.

What happens when you sit down with two brilliant friends to talk money, markets, and mindset? You get a raw, unfiltered conversation that challenges conventional thinking and rewires how you approach wealth and opportunity.

In this episode, I’m joined by Garrett Gunderson and Brad Weimert for a wide-ranging roundtable on building wealth in today’s fast-changing world.

We dive into big topics—from AI’s disruption of legal, banking, and finance, to why the smartest money is moving further away from Wall Street, to how top investors are getting early access to emerging tech and private deals. 

We also talk real estate, sharing personal stories on how to win deals—not just by offering more money, but by understanding seller psychology and waiting for the right moment.

In this episode, you’ll learn: 

1.) How AI is Reshaping the Future of Education and Work

From publishing and teaching to legal and finance, discover where AI is replacing humans—and where it’s not.

2.) Why the Smartest Investors Are Going All-In on Private Markets

Learn how the ultra-wealthy vet early-stage companies and why public markets are no longer the best path to wealth.

3.) The Secret to Winning Real Estate Deals in Any Market

It’s not always about price—see how relationships, timing, and seller psychology can unlock the best opportunities.

Show Notes: LifestyleInvestor.com/241

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.

I used to believe the key to success was working harder than everyone else.

And for a while, that served me. But over time, I started asking different questions—like what would it look like to build a life where work didn’t come at the expense of family, faith, or freedom?

This episode is a little different, as I’m the one being interviewed. Preston Brown, host of the Problems to Profit Podcast, pulls out the biggest lessons I’ve learned, from selling newspaper subscriptions in middle school to investing in private deals that create passive income and real-time freedom today.

We get into why I prioritize passive income over net worth, and how relationships and masterminds have opened the door to some of my biggest opportunities.

In this episode, you’ll learn: 

1.) How one passive income deal replaced my wife’s income—and how that one move kickstarted our journey to financial freedom.

2.) My personal framework for allocating surplus income into deals that create long-term freedom.

3.) Why I created The Lifestyle Investor Mastermind—an exclusive community giving members access to the same deals and strategies used by the ultra-wealthy.

Show Notes: LifestyleInvestor.com/240

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.

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

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.

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.

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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.

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.

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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.