I Chose Fun Over Profit…. And I Regret It

https://is1-ssl.mzstatic.com/image/thumb/Podcasts211/v4/fa/d2/39/fad239a3-0176-4bfc-3832-506d33698913/mza_10106561943700186671.jpg/600x600bb.jpg

Moneywise

Hampton

71 episodes

3 days ago

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/.

All content for Moneywise is the property of Hampton and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

Investing

Business,

Entrepreneurship

I Chose Fun Over Profit…. And I Regret It

Moneywise

35 minutes

1 week ago

I Chose Fun Over Profit…. And I Regret It

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://www.joinhampton.com/exit-report

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.