Moneywise
Moneywise is a podcast where host Daniel Berk interviews high-net-worth guests about personal finance and lifestyle. Guests share exclusive insights into their spending habits, portfolios, and burn rates. The podcast is tailored for wealthy individuals or those aspiring to wealth, and is produced for the Hampton community, a private membership group for founders and CEOs of tech startups.
Episodes
He Sold For Over $40M. Here’s His Exact Cut.
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net
He Turned Down $11B... Here's Why
Craig Newmark turned down an $11 billion offer for Craigslist, and he's already given away $570 million of his own money chasing a number even bigger than that.This podcast is made by Hampton, a community for founders doing on average $25 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make
He Sold For $1.5B But Will Never Retire
He had $15 in the bank and a $1M judgment against him. Eight years later, Nestlé bought his company for $1.5B — then shut it down.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If
He Sold 4 Companies for $1.5B. The $13M Exit Changed His Life.
We did something nuts: we got 50+ founders to reveal their net worth, portfolios, income, expenses. Its free and right here: https://joinhampton.com/mw-wrWhy this podcast exists:Hampton is a community for founders. Members do an ave of $20m/year in revenue.Tons of the convos within the community are about money: how to invest, how to spend, how much to pay yourself...all this stuff you ca
How Anne Mahlum Spends $200k/month with a $115M Net Worth
She sold for $88M, almost bought a lake house she didn't want, and spent $340K on Knicks playoff tickets — then gave two away because it felt better.We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business an
He Studied 38,000 Twins and Says Your Money Habits Are Genetic
JOIN HAMPTON:These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:How much do founders actually make, spend, inves
He Sold For $8M and Regrets It, And The Reason Why Is Shocking.
Please answer our short Moneywise listener survey! (Very, very short): joinhampton.com/moneywisefeedbackJOIN HAMPTON:These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at htt
How To Raise Great Kids When You’re Rich
JOIN HAMPTON:This episode came directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:How much do founders actually make, spend, invest, work,
He Made $400k/Month Before 30... Then Realized It Meant Nothing
MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $3M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt051126.From Minecraft maps to $400k months — but the money isn't the story.Nathan May grew up in one of the poorest neighborhoods in Ohio. His mom made $32,000 a year. He never lef
He Made $3M a Year and Decided He Had Enough
MoneyWise is a Hampton podcast. Hampton is a private, vetted community for founders doing $2M or more in revenue. Apply at https://www.joinhampton.com/?utm_source=youtube&utm_medium=video&utm_campaign=yt050526.MoneyWise | Jonathan GoodmanJon Goodman built a $35M fitness education empire from a one-bedroom apartment in Toronto, never raised a dollar, never sold a company, and never
Does Making $100M Make You Happy?
Chapter Timestamps00:00 — Homeless at 26, $100M exit at 32
02:22 — Building Mutesix: one of the first productized Facebook ad agencies
09:39 — The 2019 sale and what Steve actually took home
11:52 — The wire hits — at the Western Wall in Israel
14:46 — "The money didn't change my life": post-exit identity crisis
16:31 — How Steve actually spends: the chef, the donations, the Birkin he nev
He Has $70M And Thinks Financial Advisors Are a Waste of Money
John Arrow bootstrapped Mutual Mobile from a $0.99 iPhone app to a 350-person company — with zero investors — and sold it twice. In this episode of MoneyWise, John breaks down exactly how he built and exited one of Austin's most successful tech companies, what he did with the money, and what his financial life actually looks like today.John gets radically transparent about his net worth (
This 23-Year-Old Dropout Bootstrapped His Company to Millions
Josh Suggs is 23 years old and already running a company generating millions in revenue, completely bootstrapped. But the money story here isn't just about the numbers. It's about a kid who grew up in Westport, CT, one of the wealthiest zip codes in America, feeling like he didn't belong, watching his mom stress about retirement while surrounded by hedge fund dads, and channeling that int
$200k/Month, a 24,000 Sq Ft House, and a Billion-Dollar Trust. Our Best Moments.
This is a highlight episode. Three guests. Three completely different relationships with money. All of them more honest than they probably planned to be.Neil Patel wrote a blog post in 2014 saying he could be happy on $15,000 a month. He meant it. We brought him on to find out how that became $200,000 a month — and where it actually goes. The answer involves $35,000 in bed sheets, four ho
Matt Paulson has $25m a year in personal income - nice.
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://www.joinhampton.com This episode's sponsor is Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
Why The Founder of a $4BN Company Tracks Every Minute of His Life...
Mario Schlosser, co-founder of Oscar Health, has tracked every minute of his life in a spreadsheet since 2012. In this episode, we get into: Building Oscar Health How and why he tracks every minute of his dayThe framework he took from Ray Dalio at BridgewaterHis approach to radical transparency in leadershipCool LinksOscar HealthHampton
He Turned $40 into a $40M Sports Media Empire
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/We're testing something new on MoneyWise. Just like we got radically transparent about money, we want to do the same with company building. Let us know what you think.In this episode:
Five Founders, Same Exit Value – Wildly Different Payouts
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Five founders. Five exits. All around $30 million. So why did one walk away with $30M – and another with just $2M? From taxes and co-founders to deal structure and equity rollovers, t
These 5 Traits Predict Founder Success
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/What makes a founder truly successful? It’s not blind risk-taking or pure hustle. After two years of interviews and supporting research, we break down the five core personality traits
Weird Side Bets That Made Founders Millions
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Not every smart investment starts with a pitch deck or a business plan. Some of the best returns come from personal bets founders make with their own money. We pulled together five th
5 Luxury Purchases That Are Actually Worth It
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Everyone thinks the “rich person” life is about fast cars, fancy watches, and designer flexes. But when we talked to over 150 high-performing founders, the things they actually spend
Why Some Founders Don’t Pay Themselves
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comEveryone wants to know what founders really earn, but most of the numbers out there are either outdated or just plain wrong. We gathered fresh data from 150+ high-performing founders, and the
You’re Not a Successful Founder Until You Do This
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comEveryone’s chasing success — but what does that actually mean? Founders hit milestones, sell companies, and still feel unsatisfied. After 150+ interviews, the most consistent lesson is that mo
I Built a $9M Company And Got Nothing
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comKevin Bartchlett built a $9M compost toilet company from the ground up – and walked away with nothing. No contract, no payout, just a handshake. That blind faith turned into a hard lesson in t
He Built a $20M Brand Without a Media Background
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comAdam White didn’t set out to build a media company – he just wanted a job in sports. So at 19, he started posting informational interviews on a Wix site. Today, he runs a $20M brand with NFL p
The Founder Exit Report: What Happens When You Sell a Company?
Get the full exit report here: https://joinhampton.com/rich-or-dead-reportStop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comMost exit stories are told in headlines and highlight reels. We wanted the truth. So we surveyed dozens of exited Hamp
What No One Tells You About Scaling Fast
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comAlex Smereczniak built a $100M laundry business and sold 118 franchise locations in just 14 months. But just as the business took off, life hit hard. After a series of personal and professiona
40 Restaurants in 5 Years: The Blueprint Behind a $100M Sushi Empire
Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comMost founders start their restaurants in the red. Guy Allen did the opposite, turning a 12-seat sushi bar into a $3M business with lines out the door and plans for a $50M exit. He’s the founde
He Sold for $200M – Then Watched the Business Implode
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comKory Mitchell built a blue collar asbestos business and sold it for $200M. When he stepped back, everything started to fall apart. A new CEO lost millions. The culture cracked. Kory came back
How They Built a $745M Company Together and Stay Married
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Kass and Mike Lazerow built two companies together, sold one for $25M… and the next for $745M. Along the way, they went bankrupt, survived dot-com busts and Facebook booms, and figure
I Sold My Company for $22M. Here’s Why I Bought It Back.
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comJaclyn Johnson sold Create & Cultivate for $22 million. Then she hit pause – burned out, got divorced, and took a year off to figure out what she actually wanted. Now? She’s back, running
I Chose Fun Over Profit…. And I Regret It
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comJordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he left too much money on the table.Here’s what we talk
$12 Million Exit... Did He Just Get Lucky?
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comDonald Spann built a multi-million dollar call center from scratch — with no outside capital, no technical background, and no safety net. Even crazier? He sold it for $12M to the first person
Rajiv Khaneja Made Millions Young, Then Refused to Upgrade His Lifestyle
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comRajiv Khaneja made tens of millions running an ad tech company, but still lives in the same city he grew up in, wears the same clothes, and told friends he rented his house—even though he owne
Why Ali Abdaal Thinks 6-Figure Freedom Beats a 9-Figure Exit
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comAli Abdaal didn’t sell a startup. He didn’t raise money. He didn’t even plan to leave medicine. He just turned himself into the business, and ended up happier, wealthier, and more free than he
Rob Townsend: The $10M Advisor Who Thinks You’re Investing All Wrong
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comRob Townsend says you’re wrong about financial advisors… mostly. And he’s built an 8-figure firm to prove it.Here’s what we talk about:Why $3M liquid is Rob’s version of “f*** you money”How he
The High-End Art Market: Strategy, Status, and Serious Returns
Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comEverything you need to know about turning art into a real (and risky) investment strategy.Carlos Cardenas is a Private Wealth Advisor at Austin Wealth Management, bringing over 20 years of exp
This is How Much Alex Hormozi is Actually Worth
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportInside Alex Hormozi’s decade-long climb from $0 to $200M+.Here’s what we talk about:A transparent breakdown of his $200M+ net worth: $95M in liquid assets, $100M+ in illiquid equityThe Gym Launch explosion: from near-bankruptcy to $42M in distributions and a $31M
A $150M Ride: Private Equity, Planes, & a $1M Butt Tattoo
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportChuck Yates rode the wildest wealth rollercoaster: $150M up, $82K down, now back at $20M. In oil & gas private equity, he made (and lost) fortunes and never flinched. For Chuck, money’s just part of the story. Mindset is everything.Here’s what we talk about:Ho
She Died. Now She Charges $1M to Help the Wealthy Find Love.
Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-reportAmber Lee was literally brought back to life, and then decided to start over.Here’s what we talk about:After a near-death experience in 2020, Amber finally launched her dream matchmaking business from the hospital.She bought her mom a house and moved to Puerto Ric
15 Years Doing What I Hated… 8-Figure Exit. Worth It?
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportHow Ronan Berder accidentally built a consulting agency, scaled it to 8 figures, and sold it, despite never enjoying the work.Here’s what we talk about:Why Ronan stayed in China running a business he didn't love, and the deep sense of duty
$10M Net Worth. $2.5M Cashflow. No Plans to Exit.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJay Berard’s never sold a company, but with $2.5M in cashflow and $10M net worth, is he confidence-rich or risk-blind?"Here’s what we talk about:His early days: a Craigslist job ad, 100% commission, no safety net… and a one-way ticket from
$10M vs $100M: The Difference Between Being Rich and Really Rich
Jackie breaks down exclusive data from 127 millionaire founders inside Hampton, revealing how motivation, money management, and mindset evolve as net worth grows, from $1M to over $100M.Here’s what we talk about:Why financial security stops being a motivator after $50M—and what takes its placeThe "F*** You" number: What real numbers show is the threshold for total financial freedomWealth
Re-Up: I’m Worth ~ $500m. Here’s What I Regret (And Don’t) Spending On with Andrew Wilkinson
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report.Andrew Wilkinson became rich in his 20s — but early wealth came with hard lessons. In this episode, Andrew opens up about:How he went from buying everything he wanted to nearly going bankrupt in 2008The emotional rollercoaster of building
I Let Go of the Hustle. Embraced Feminine Leadership. Built $10M.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJess Chan scaled to 7 figures fast, then tore it all down. Today, she’s worth ~$10M, spends less than ever, and says profit > revenue every time.Here’s what we talk about:Jess hit $40K/month as a freelancer, then walked away to build her
How Much Does It Really Cost to Fly Private?
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportIs flying private a waste of money, or the ultimate time hack for the ultra-wealthy? In this episode, we break down what it really costs, who it makes sense for, and why even billionaires think twice.Here’s what we talk about:Private aviati
$60M Exit, 25+ Deals, and Why Angel Investing Isn’t For Most | Auren Hoffman
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAuren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.Here’s what we talk about:Auren Hoffman made $60M—and then became an angel investor.He shares why angel
How Nick Huber Stays Humble with a $50m Net Worth and 25k Burn
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportHe’s worth 8 figures, owns a private jet, and still tracks every dollar. Nick Huber says avoiding lifestyle creep is harder, and more important, than getting rich.Here’s what we talk about:How Nick Huber built an 8-figure net worth from swe
+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAfter a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.Here’s what we talk about:Anastasia’s journey from a bootstrapped nine-figure success to divorce, burn
My $70M Exit Collapsed Days Before Signing
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAdam Robinson was days away from a $70M exit… then the buyer walked. But the deal collapsing turned out to be a blessing.Here’s what we talk about:His current company now does $25M ARR with $1M monthly profit.He accidentally spent millions
$100K Buy-In. $160M Exit. Then $40K/Month on ‘Living the Dream’... Almost.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportAfter a $100M+ exit, Jace Mattinson blew $40K a month chasing lost time, until living the dream nearly ruined it.Here’s what we talk about:Jace shares how he turned a failing 135-year-old business into a $160M exit.Why buying old and boring
$100M Lifestyle, Billionaire Family — The Call That Changed Everything | Alex Peykoff
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportWhat happens when you grow up alongside a billion-dollar company, lose yourself chasing money, drugs, and approval, and have to rebuild your life from scratch? That’s what happened to Alex Peycoff.Here’s what we talk about:Why growing up i
$10M and Total Freedom, I Left the Family Empire to Build My Own
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportShane Cultra walked away from his family's five-generation nursery business—triggered, in part, by watching Succession. Along the way, he built up a $10M net worth, stacked Bitcoin, turned a blog into a domain empire, and made peace with a
$13M But Zero Cash: Why Net Worth Is a Lie
If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.Mike Brown built an oil & gas empire, scaled his net worth to nearly $20 million, but ended up cash poor, losing $1.8M in a failed bet, and borrowing money from his wife to pay taxes. Now, he’s rebuilt his fortune, redefined what wealth really means, and is living a life designed arou
I Asked 100+ Millionaires If Money Makes You Happy
If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. Both of those things are true.Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?).In t
$32M Exit: Left the U.S., Built a $15K/Month Life in Japan
If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.Eran Galperin bootstrapped a niche SaaS for Brazilian Jiu-Jitsu gyms, sold it for $32.5 million, moved to Japan, and is now quietly living the FIRE dream — with a few luxury upgrades.Here’s what we talk about:- How Eran went from $15K in the bank to a $32M exit (with 90% equity!)- Why he
I'm worth $50m and Have No Idea What To Do With My Life
If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.Vinay Hiremath co-founded Loom and sold it for nearly $1 billion… then walked away from $60 million, gave most of his early money to his parents, and now he’s looking for internships.Here’s what we talk about:How Vinay went from broke stoner to $50–70 million exitWhy he voluntarily left t
Inside the $30M Exit of a Socialist Buddhist
If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.Chris Cooke is a socialist Buddhist who sold his company for $30 million… then blew most of it on a weed farm, a beach house, and a comedy club in Thailand.Here’s what we talk about:How Chris accidentally “won” capitalism—despite deeply skeptical views of moneyWhat happens when your value
I Sold for $100M and Now I Spend $1M/Year
This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.Inspired by real conversations happening in the Hampton community.If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.Dan Berger sold his company Social Tables for $100 million in 2018. But his net worth today hasn’t moved at all. Why?Here's what we
How Tommy Mello Became a Billionaire Painting Garage Doors (And How He Shares the Wealth)
What does it take to turn a blue-collar business into a billion-dollar empire?For Tommy Mello, the answer is simple: relentless competition, strategic investing, and an unwavering commitment to winning. From painting garage doors to building A1 Garage Doors into a massive industry leader, Tommy has played the long game—and he’s not slowing down anytime soon.Tommy’s story is one of grit, s
"I Fast-Forwarded My Life 10 Years”: How Geo-Arbitrage 3X’d My Wealth and Changed My Life
What if you could fast-forward your financial goals by ten years just by moving abroad?That’s exactly what entrepreneur Rob Hoffman did when he relocated to Colombia, where his $3M net worth stretches as if it’s $9M.Rob, a member of the Hampton community, shares how he built a successful marketing agency while living in Medellín. Once an anti-capitalist hippie, Rob’s journey took him from
How Comic Books Are Making Me Richer with Rob Walling
Would you put millions into comic books? It sounds crazy, but for Rob Walling, it’s part passion, part strategy.He’s met people at the airport just to pick up a single book. But this isn’t just nostalgia—it's an investment play.Rob Walling is a serial entrepreneur who sold his SaaS companies for millions. But instead of Ferraris, he spends big on collectibles—rare comics, original artwork
From Startup to $40M Exit – And We’re Still Just Brothers
Most founders feel isolated after selling their company. Chris and David Sinkinson didn’t—because they had each other.The brothers built and sold their startup, AppArmor, for $40 million. But unlike many founders who struggle with identity and purpose post-exit, they had a built-in support system: each other. With a 10-year age gap and complementary skills, they navigated the highs and lo
Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life
What if the key to success wasn’t grinding harder—but learning to let go?Chris Bakke made 10s of millions selling two companies, including one to Elon Musk’s Twitter. But after years of chasing big wins, something changed: he had kids. And suddenly, the drive that once defined him wasn’t as important as being present for his family.Chris started as a scrappy startup founder, building and
$500M and Still Asking "What’s Next?": Peter Wokwicz’s Guide to Curiosity-Driven Success
What if chasing curiosity, not cash, was the key to a richer, more fulfilling life? Peter Wokwicz turned his relentless curiosity into a $500 million fortune—and found happiness along the way.Peter didn’t build his wealth by following the typical playbook. Instead of just chasing cash, he let his curiosity lead the way—and it’s resulted in over 40 successful exits, groundbreaking innovati
MiniWise: Why Checking Your Portfolio Every Day Might Be Ruining Your Life
Are you obsessively checking your portfolio—or avoiding it entirely? What’s the right approach to managing your money post-exit?In this Mini-Wise episode, Sam Parr breaks down how three ultra-wealthy entrepreneurs—Chuck (net worth: hundreds of millions), Travis (net worth: $50M), and Anne Mahlum (net worth: $100M+)—handle the mental rollercoaster of market fluctuations. Each shares their
The $300 Million Exit That’s Funding Humanity’s Future with Bryan Johnson
Most people think Bryan Johnson just wants to live forever.They’re wrong.Bryan’s real goal is to leave a legacy that will last centuries.In this episode, we uncover the extraordinary vision of Bryan Johnson, an entrepreneur driven by the audacious mission to earn the respect of people living in the year 2500.Bryan isn’t just the man who sold Braintree (the parent company of Venmo) for $30
When the Numbers Define You: Life After a $50M Exit
Why do we let numbers define us—and what happens when they finally stop moving?Fred’s journey from corporate finance to a multi-million-dollar exit reveals the emotional rollercoaster behind financial success and the unexpected lessons that follow.Fred, an introspective entrepreneur, sold his company for a mid-eight-figure sum. His story isn’t just about numbers—it’s about the sacrifices,
Is a 24,000 sq ft Home Worth It?
RE-RUNIf you have the money to put anything you could possibly want in your home, should you do it?This episode’s guest, “Hank” did, and as a result, his home ended up being 24,000 square feet.But with 24,000 square feet, there is a lot to go wrong. So are the upkeep, repairs, and bills worth the square footage? Can a home with all the fancy features you can imagine actually bring more jo
How Neil Patel Spends $200K a Month
RE-RUNThere was a time when Neil Patel said a $15k/month burn rate was all he needed. But now his monthly burn is $200k. Roughly. He’s not completely certain… because he doesn’t budget. So what changed in his life to make his burn rate increase nearly 14 fold? That’s what this episode is going to find out.Neil Patel is a household name (for marketers). He’s an entrepreneur and blogger kno
$1B and Counting: Steve Houghton’s Five Pillars for Living a Truly Wealthy Life
What’s the real cost of building wealth—and how do you stay grounded after achieving it?Steve Houghton, a billionaire entrepreneur, has a life philosophy that’s as intentional as his business strategies. From self-made success to crafting a fulfilling personal life, Steve shares the five pillars that help him stay healthy, happy, and wealthy.Steve’s journey started with selling books as a
Re-Run: Why Someone Worth $150M Liquid Only Spends $5K Monthly
RE-RUNImagine being worth $150 million. Liquid. Now imagine being worth that much, and only spending $5,000 a month.That’s the reality for this episode’s guest.“Cam” is going to share a lot of financial details with us, so he’s asked to remain anonymous. What we can tell you, is that he made most of his money when a business he started went public at a valuation of around a billion dollar
A $2.5B Exit and The Risks Nobody Talks About
What happens when wealth pushes your relationships to the limit?Navigating life after a massive financial windfall isn’t easy—it can transform your life, your marriage, and your happiness in unexpected ways.Our guest, Chuck, shares his story of selling his company for $2.5 billion and the emotional and relational challenges that followed. His perspective is shaped not only by his own jour
Sold For $80 Million - Then Hit Rock Bottom
What happens when the big exit doesn’t fill the void?Josh Payne thought selling his company for $80 million would be the defining moment of his life. Instead, it sent him into one of the darkest periods he’d ever experienced.Josh’s story is a testament to the complexity of success. As the founder of StackCommerce, Josh grew his company from $0 to $32 million in annual revenue, eventually
$7 Million at 18 to $112 Million in Assets: How Jacob Turner Built a Business After the MLB
What would you do if you became a millionaire at 18? For MLB pitcher Jacob Turner, the real question was: how do I make sure I don't lose it all?Jacob signed a $7 million contract with the Detroit Tigers as a teenager, and suddenly, his life changed overnight. While most of us can’t imagine dealing with that level of wealth so young, Jacob had to figure it out fast—and he didn’t want to b
Top Money and Life Secrets from 25 Millionaires: What You Should REALLY Know
We just hit our 25th episode! To celebrate, we’re doing a special recap of the best lessons from all our past conversations. Sam’s looking back at the standout advice from founders, entrepreneurs, and experts who opened up about what really happens when you hit major financial success—and the stuff no one talks about.You’ll hear insights from Mike Beckham on why giving back keeps lifestyl
$100M Net Worth, $5M Income: How I used money to handle a cancer diagnosis
What’s the true value of money when faced with a life-or-death situation?Mitch found out the hard way when his wife was diagnosed with cancer.As a highly successful entrepreneur with a net worth of nearly $100 million, Mitch had built a life of financial security. But when faced with his wife’s illness and his own health scare, he discovered that no amount of money could buy control over
“I’m worth about $3 billion” What Happens When You DON’T Sell Your Business
What happens when you don’t sell your company and keep growing it for decades? For Oscar, it means you become a billionaire.Oscar bought a company every six weeks for 20 years and now his business is worth about $50 billion. Yet, he still wears $15 t-shirts and lives by the values that helped him achieve success.In this episode, he shares how he became a billionaire while always putting f
"I Thought I Had the Midas Touch": How an $80M Success Led to a Major Failure
Can success create a false sense of invincibility? For Pete, it did—and it cost him millions.After selling his business for $80 million, Pete felt unstoppable. But his overconfidence led him into a risky venture that didn’t pay off. Determined to prove he wasn’t a one-hit wonder, Pete ignored the warnings, thinking his past success guaranteed future wins. Instead, he faced one of the hard
"How I quit the hustle to enjoy life”: Getting Off the Treadmill with a $15m Net Worth
How Do You Stop Hustling When You’ve Already Won?Laura Roeder told herself that at $5 million liquid she could live the life she wanted and refocus her life on what matters most: living. Unlike a lot of entrepreneurs who get caught up in the game and keep chasing more, Laura stayed true to that goal and quit hustling harder than she had to. But how did she avoid the endless treadmill for
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