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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.