I Chose Fun Over Profit…. And I Regret It
· 34 min · Episode 71
Episode 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.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.
Links in the notes 5
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