I Chose Fun Over Profit…. And I Regret It
Moneywise
00:00
Intro
Harry introduces Jordan, Rainmaking, and the episode's central question: was choosing fun over profit the right move?
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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.
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