I Chose Fun Over Profit…. And I Regret It

Listen to this episode from Moneywise on Spotify. 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 about:Why Jordan left a lucrative investment banking path to chase startupsHow the Rainmaking model let him share risk (and reward) with fellow foundersThe downside of passion-led business: no investment thesis, millions wastedWhy he believes he could’ve made way more money doing less exciting workWhat he thinks about his $4M liquid net worth — and why it doesn’t feel like enoughThe moment he realized private equity is a better game than startupsHow he’s now trying to turn around a $10M beauty business without raising capitalWhat it really costs to live well in London as a founder with a familyWhy he regrets chasing the “cool” startup dream instead of playing it safeWhat true wealth means to him today: help, time, and optionalityCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174Sponsors:Tam your taxes today at https://olarry.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:(0:49) Breaking Down the Rainmaking Model(2:08) Jordan’s Pivot from Investment Banking to Startups(4:15) Why He Couldn’t Stay Away from Startups(5:43) The Origins & Vision Behind Rainmaking(8:48) Biggest Challenges in the Rainmaking Model(10:57) Costly Mistakes & Lessons Learned Along the Way(13:00) Why Jordan Stepped Away from VC(17:05) Taking Over as CEO of a Beauty Brand(18:23) Jordan’s Current Finances & Where He Stands Today(20:23) Lifestyle Adjustments & Financial Struggles(24:32) Life Before Family vs. Life After(29:04) What He Wishes He’d Done DifferentlyThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.