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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 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:
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.
What is Moneywise?
This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.