The Lifestyle Investor - Investing, Passive Income, Wealth

Every entrepreneur dreams of the big exit, yet for many, the American Dream can quickly turn into the American Nightmare. Within five years, Alex Bean went from startup founder to selling Divvy for $2.5 billion to Bill.com—making enough money to never work another day in his life. But instead of fulfillment, he was blindsided by loneliness, loss of identity, strained relationships, and new family...

Success in business and investing often gets framed as tactics, strategy, or sheer hustle. But according to David Bayer —renowned mindset and performance coach, transformational speaker, and founder of the Powerful Living Experience—the real driver isn’t what you do, it’s the state of mind you operate from. David has guided thousands of entrepreneurs and leaders through his coaching programs, live...

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 bus...

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 re...

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 ou...

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+ year...

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 1...

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 t...

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 w...

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 mil...

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 adv...

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 inve...

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...

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...

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, p...

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...

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...

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 profess...

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 tra...

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 serv...

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, rev...

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-stor...

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...

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 man...

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 histo...