The Lifestyle Investor - Investing, Passive Income, Wealth

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252: How to Protect and Grow Wealth After Selling Your Business with Jay Jacobs Aug 21, 2025

Show notes

Building and selling a company is hard—but managing wealth afterward is a completely different challenge.

Jay Jacobs knows this firsthand. An OG member of The Lifestyle Investor Mastermind, and my very first Private Client, Jay founded RAPID Manufacturing in 2001 and grew it over 17 years into the world’s largest prototype sheet metal manufacturer and the second-largest prototype CNC machining business. RAPID’s success was fueled by leveraging modern technology—and after selling the company for 9-figures, Jay launched Paperless Parts to give other manufacturers access to the same kinds of tools. Today, Paperless Parts is the #1 quoting and estimating software in manufacturing, with $25M ARR.

But even with all that success, Jay faced a new reality after his exit: the skills that made him a world-class entrepreneur weren’t the same ones he needed to protect and grow his wealth.

As an entrepreneur, he was used to taking calculated risks, moving fast, and having full control over outcomes. As an investor, the rules were different—success meant slowing down, saying “no” more often than “yes,” and trusting others to be good stewards of his capital. The optimism and risk tolerance that served him in business could quickly become liabilities in investing.

In this conversation, he shares how he made that transition—building a passive income stream to replace his paycheck, creating guardrails to avoid costly mistakes, and designing a life filled with impact, travel, and passion projects. You’ll hear the mindset changes that guide his decisions, the relationships that open up high-quality deal flow, and the lessons that can help you avoid the costly mistakes that wipe out fortunes.

In this episode, you’ll learn:

1.) Why the skills that build a company aren’t the same ones that grow and protect wealth—and how to make the shift from entrepreneur to investor.

2.) The strategy behind Jay’s leap from a 9-figure exit to building a $25M ARR industry leader in manufacturing software.

3.) The lifestyle design strategies Jay uses to turn passions into profitable ventures and create unforgettable life experiences.

Show Notes:LifestyleInvestor.com/252

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251: They Stole His $1B Company While He Was on His Deathbed with Adel Sayegh Aug 14, 2025

Show notes

He was dying. They thought he wouldn’t survive. So they stole his $1B company.

Adel Sayegh built a billion-dollar business from nothing—pioneering security tag technology, facial recognition, and GPS tracking. But while he lay on his deathbed battling pancreatic cancer, the people he trusted most betrayed him.

They drained his accounts, forged documents, and used his assets to rack up debt. The result? A complete collapse of the empire he spent decades building.

In this raw, emotional episode, Adel shares the true story of how he lost everything—and why he wouldn’t trade the experience for anything. From surviving terminal illness to finding unshakable peace through his faith, this is one of the most unbelievable stories ever told on the podcast.

In this episode, you’ll learn:

1.) Why Adel chose forgiveness over prosecution—even after being betrayed by his most trusted team members.

2.) The hard-earned lessons from bootstrapping a billion-dollar company from his garage—and why he wouldn’t take the same approach today.

3.) How faith—and unexplainable miracles—helped Adel survive terminal cancer and discover a greater purpose.

Show Notes:LifestyleInvestor.com/251

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250: Redefining Success as a Husband & Father with Jon Vroman and Hal Elrod Aug 07, 2025

Show notes

Ok, this episode is a little different than usual.

Instead of interviewing a guest, I got to sit down with two of my closest friends—Jon Vroman and Hal Elrod—for the 500th episode of the Front Row Dads podcast.

This wasn’t a business conversation. It was personal. We talked about fatherhood, faith, marriage, brotherhood, and how this community has completely changed the way we show up for our families.

I opened up about my health struggles with mold toxicity, how it forced me to slow down, and the surprising gift that came out of it. We also talked about the hard-earned lessons that helped us re-prioritize our marriages, restructure our calendars, and redefine what success really looks like.

I’ve been part of Front Row Dads from the very beginning, and it’s no exaggeration to say that it’s the most impactful community I’ve ever been part of. If you’ve ever wrestled with being present at home while building something meaningful in the world—this episode is for you.

And if you want to learn even more about fatherhood, marriage, and how to level up your game at home, visit FrontRowDads.com to learn more.

In this episode, you’ll learn:

1.) Why saying family comes first isn’t enough—and how to build a life that actually reflects it

2.) The hidden habits and vices that hold men back—and why brotherhood is essential for breakthrough

3.) How to lead your kids by example and pass on the values that matter most

Show Notes:LifestyleInvestor.com/250

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249: The Proven Membership Strategy for Predictable Profits with Stu McLaren Jul 31, 2025

Show notes

What if you could stop chasing one-time sales and build a business that pays you again and again—predictably, reliably, and without the hustle? That’s exactly what today’s guest, Stu McLaren, has helped thousands of entrepreneurs achieve.

As the co-founder of Membership.io and creator of The Membership Experience™, Stu is one of the world’s leading membership experts. He’s spent the last 16+ years helping entrepreneurs turn what they know and love into thriving membership businesses that generate recurring revenue and real freedom. And now he’s packed everything he’s learned into a new book called Predictable Profits.

In our conversation, Stu breaks down what actually works when it comes to memberships—what keeps people around, what makes them leave, and how to build something that lasts. No fluff, no hype—just real strategies that actually move the needle.

In this episode, you’ll learn:

1.) Why the membership model is the ultimate path to predictable profits—and how it can boost your business valuation, create lifestyle freedom, and unlock compounding revenue over time.

2.) The success path framework that will give your members clarity and direction—so they avoid overwhelm, stay engaged longer, and actually get results.

3.) How to 3x the lifetime value of your members by optimizing their first 30 days with one simple onboarding strategy.

Show Notes:LifestyleInvestor.com/249

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248: How to Lead With Wild Courage (Even If You’re Afraid) with Jenny Wood Jul 24, 2025

Show notes

What if the very traits you've been taught to hide—like being selfish, nosy, or even manipulative—are actually your greatest unfair advantage?

That’s the bold idea Jenny Wood explores in Wild Courage—a framework she developed after nearly two decades at Google, where she rose through the ranks, led billion-dollar business units, and launched initiatives that reached over 50,000 employees across 100+ countries.

Eventually, success on paper wasn’t enough. Jenny felt burned out and boxed in—stuck between achievement and alignment. That turning point led her to redefine what real courage looks like in business and life.

In this episode, she unpacks the 9 traits society often labels as “too much” or “too aggressive”—and shows how to reclaim them as strategic tools for influence, opportunity, and a life you actually want. Whether you’re looking to land the promotion, launch your business, or stop playing small, this conversation will challenge everything you thought you knew about confidence, leadership, and courage.

In this episode, you’ll learn:

1.) The wild subway story that changed Jenny’s life—and the mindset shift that helped her take bold action in the face of fear.

2.) Discover the 9 unconventional traits that define Wild Courage—and how they unlock greater influence, freedom, and business growth.

3.) Why “manipulative” might be your most powerful leadership trait—and how to use it to build trust, influence, and high-leverage relationships.

4.) Why replacing your salary may be the wrong goal—and how to build confidence, earn through passive income, and design a life that truly aligns with what matters most.

Show Notes:LifestyleInvestor.com/248

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247: The Ad Copywriter Behind Billion Dollar Brands with Roy H. Williams Jul 17, 2025

Show notes

Want to know the biggest reason your marketing isn’t working? It doesn’t reflect you.

Most ads are generic. They could work for any business. But the best ads only work for one—because they’re built around the true personality of the founder or brand. They’re specific, not because of the product, but because of who’s behind it. That’s what makes them powerful. That’s what makes them real. That’s the heart of relational marketing— which is what today’s episode is all about.

I’m joined by Roy H. Williams—better known as the “Wizard of Ads”—who has helped iconic companies like 1-800-GOT-JUNK craft ads that fueled billion-dollar growth. Over the past 40 years, Roy has advised hundreds of founders, showing them how to grow through story, truth, and personality, instead of gimmicks, hype, or shallow tactics.

If you want to write ads that break through the noise and actually connect with your buyers, this episode will change the way you think about marketing forever.

In this episode, you’ll learn:

1.) How Roy helped grow 1-800-GOT-JUNK from $97M to $1B—by leading with truth and identity, not data or demographics.

2.) Why identity—not logic—drives every buying decision, and how your brand can tap into who your customers really are in order to better serve them.

3.) What makes a company truly remarkable—and the one question Roy uses to test if your marketing actually makes people care.

4.) The 4 things every human is secretly looking for—and how to build them into your ads so people don’t just notice you… they trust you.

Show Notes:LifestyleInvestor.com/247

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246: The Hollywood Director Who Lives Life on His Terms Matt Earl Beesley Jul 10, 2025

Show notes

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

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245: The Capital Gains Tax Strategy You’ve Never Heard Of (But Should Be Using) with Brett Swarts Jul 03, 2025

Show notes

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

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244: How to Build Wealth Without Sacrificing Your Family with Chad Willardson Jun 26, 2025

Show notes

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

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243: He Analyzed 1,000+ Billionaire Strategies (Here’s What He Found) with Richard Wilson Jun 19, 2025

Show notes

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

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