I Chose Fun Over Profit…. And I Regret It
Moneywise
Hampton
4.7 • 701 Ratings
🗓️ 23 September 2025
⏱️ 36 minutes
🧾️ Download transcript
Summary
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.
Transcript
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| 0:00.0 | It was fricking fun, but I honestly can tell you hand and heart, we would have made way more money |
| 0:09.1 | had we been focused and had a clear investment thesis. If I'd stayed in investment banking in M&A, |
| 0:16.0 | I would be a lot wealthier now. I don't feel that I've achieved the monetary success or the scores on the |
| 0:25.1 | scoreboard, if you will, in like the business game, which basically comes down to money, |
| 0:29.7 | that matches what I think my talent or potential is. Jordan Schlipp got into entrepreneurship, |
| 0:35.2 | not because of the money, but because he loves the game. He's a serial founder, he's taught startup courses around the world, and most recently he's found himself as the CEO of a beauty brand. |
| 0:45.3 | But by far the most interesting thing he's done is a project called rainmaking. |
| 0:48.3 | It's somewhere between a syndicate and a startup studio, basically a bunch of founder investors pulled together their money and |
| 0:54.2 | resources and used it so that they could individually start whatever startups they thought |
| 0:58.4 | were interesting at the time. That meant that they also shared in all of the profits. So if |
| 1:03.4 | one of these companies took off, then everyone in the group would benefit. It meant that they could |
| 1:08.4 | all individually pursue the different things and opportunities |
| 1:10.9 | they thought had a bunch of potential and they would be hedging their bets and splitting the |
| 1:15.3 | winds among them. He spent years optimizing for enjoyment, curiosity, fulfillment and financially |
| 1:20.7 | it worked out fine. Plus he's still got a few irons in the fire. He's worth about $4 million USD liquid. |
| 1:26.6 | He's got a couple more million non-liquid |
| 1:28.4 | tied into rainmaking and he pays himself £200,000 a year as a regular salary. Yet still, |
| 1:34.3 | he can't help but wonder if he chose the wrong path. All this time should he instead of |
| 1:38.3 | optimise just purely for financial gain? Was the fun worth it? That's the conversation |
| 1:43.7 | we're going to have today. I'm Harry Morton and this is Money Wise, a podcast not about how to get rich, but about the ups and downs that come with being a founder already in the game. It's made for the Hampton community of high net worth founders, which both Jordan and I are a part of. More of that in a bit, but if you're curious now and you're a founder doing at least three million in annual revenue, check it out at joinhampton.com. |
| 2:07.9 | Right now, though, let's get a quick overview of how and why rainmaking came to be. |
| 2:12.1 | For Jordan, it started in investment banking. He did not enjoy it. |
... |
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