Moneywise

He Has $70M And Flies His Own Plane Wherever He Wants

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 (well into 8 figures), his monthly spending ($50–65K/month), his investment strategy, and why he thinks most wealth managers are a waste of money. Plus: the illegal Cuba trip right before signing a life-changing deal, the $500K bet to hack Apple's encryption, how he sued American Express on behalf of a friend and won in 48 hours, and the new AI company he built the morning of this recording. Topics covered: * How John made his first $1,000/day at 14 years old * Bootstrapping Mutual Mobile to a $70M exit with no outside funding * What actually happens the day a wire hits your account * Why he sold the company a second time — and for how much * His exact portfolio breakdown (stocks, private investments, real estate) * Why he never drinks (the real reason) * FreedomGPT and the future of uncensored AI * How to think about money once you never have to work again 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  Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com Oceans - Hire incredible talent for marketing, ops, sales, and more, and even have them build out all your AI workflows for you. Go to https://www.oceanstalent.com/moneywise now.

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 into an obsession with building things from the age of 13. Daniel and Josh get into the real numbers: what Josh actually takes home, where it sits (mostly cash, barely invested, and he'll tell you why), and what his monthly spend actually looks like living in New York. Spoiler: $3,000/month on Uber because he refuses to take the subway. ABOUT MONEYWISE MoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk. New episodes in production now. ____________ 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

$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 homes in Beverly Hills, and donations that dwarf his actual lifestyle spend. Hank — not his real name — built a $3 billion cell phone distribution company, exited in 1996 for $60 million, and eventually found himself standing inside a 24,000 square foot house wondering how it happened. He paid $10 million. Cash. No mortgage. And runs it like a part-time job. He never says his net worth. He doesn't have to. Taylor Adams grew up in a Los Angeles family with over a billion dollars in assets going back to the 1890s. Got sober at 26. Now helps wealthy families avoid destroying what the first generation built. He has a framework for how that destruction happens. He calls it the Four Horsemen. Every one of them sounds like good advice. Three clips. Three moments worth rewinding. This is MoneyWise. FEATURED GUESTS * Neil Patel — Founder, Neil Patel Digital & Crazy Egg * Hank — Anonymous. Cell phone distribution. $60M exit. 24,000 sq ft. * Taylor Adams — Founder, Belief Partners. Fourth-generation family wealth. ABOUT MONEYWISE MoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk. New episodes in production now. ____________ 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

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 day * The framework he took from Ray Dalio at Bridgewater * His approach to radical transparency in leadership Cool Links * Oscar Health [https://www.hioscar.com] * Hampton [https://www.joinhampton.com]