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.com Jordan 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 startups How the Rainmaking model let him share risk (and reward) with fellow founders The downside of passion-led business: no investment thesis, millions wasted Why he believes he could’ve made way more money doing less exciting work What he thinks about his $4M liquid net worth — and why it doesn’t feel like enough The moment he realized private equity is a better game than startups How he’s now trying to turn around a $10M beauty business without raising capital What it really costs to live well in London as a founder with a family Why he regrets chasing the “cool” startup dream instead of playing it safe What true wealth means to him today: help, time, and optionality Cool Links: Hampton https://www.joinhampton.com/ Lower Street https://www.lowerstreet.co/ Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174 Sponsors: Tam your taxes today at https://olarry.com/ Achieve your dream body with https://www.dailybodycoach.com/moneywise Protect your upside and get your time back at https://www.cressetcapital.com/moneywise Chapters: (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 Differently This 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 Morton Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts. Co-parents a cow named Eliza.
