The Lifestyle Investor - Investing, Passive Income, Wealth

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 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, su...

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 mark...

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 Braveh...

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...

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 bu...

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 w...

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 f...

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, ...

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...

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 se...

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...

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 we...

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...

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...

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 pri...

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, dist...

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 ben...

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 thei...