Step Away or Die: The Brutal Cost of Building a $500M/Year Company

Moneywise

Hampton

Business, Entrepreneurship, Investing

4.8 • 674 Ratings

🗓️ 22 July 2025

⏱️ 57 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Santiago Aparicio built a $500M company, then faced a choice: step away or die.

Here’s what we talk about:

Santiago shares his $22M net worth and the breakdown.
He rents instead of owning real estate to keep life flexible.
Spends freely on watches and Porsches, but says they are assets, not expenses.
Grew up in Colombia with wealth but strict spending limits, which fueled his drive.
Joined Rappi early, then co-founded Fitpal, before chasing bigger ideas.
Built a payroll company from zero to $500M/year fast, but felt miserable.
Constant comparisons made him feel like a failure despite success.
Ignored health issues until he developed a severe heart condition.
Family forced him to choose: company or life.
Walked away while the company was thriving, leading to an identity crisis.
Now working with Bryan Johnson on health tech at Blueprint.
Says success comes at a cost, and many founders hide how miserable they really are.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Chapters:
(01:34) Santiago's Financial Breakdown
(04:09) Luxury Spending Habits
(05:10) Early Life in Colombia
(08:37) Entering the Startup World
(10:37) The Rappi Journey
(13:29) Building FitPal
(17:14) The Y Combinator Playbook
(19:18) The Goalposts Keep Moving
(24:44) The Fleeting Joy of Success
(26:46) Aggression and Overwork
(28:47) Health Scare and Realization
(34:13) Stepping Down and Identity Crisis
(40:47) Reflections on Sacrifice and Success
(43:43) Challenging Hustle Culture
(47:31) Working with Brian Johnson

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	All right, so here's the deal. I just came from our 25-person all-hands meeting with all my staff at Hampton.
0:08.6	About four of the 25 people there, they were people we found via a company called Oceans.
0:15.3	Offshoring, it gets a bad rap. And it gets a bad rap because a lot of people think that the people you hire via
0:21.8	offshoring firms are low-level talent and do low-level work, or they just do stuff that AI is
0:28.0	already replacing. That is not true at all. The people who we have, they help us with marketing,
0:33.4	they do operations, and we treat them as fully part of our team because they are.
0:39.5	And what's great about oceans is you can get top talent and finance marketing operations,
0:44.0	basically any role that you're hiring for, for only about $3,000, at least that's the starting
0:48.9	point.
0:49.6	And you can get amazing, talented people in like two weeks.
0:52.9	I think we've got one of these folks who work for us. I think we've got her in like five days and she's amazing. We've worked with her for like a year now. If you don't want to burn a lot of cash, but you still want the best high caliber people, you guys got to check them out. It's oceanstalent.com. And please tell them that Sam sent you and they're going to give you a little bit extra special treatment.
1:12.0	Again, oceanstalent.com.
1:18.2	That was like, okay, I'm going to die.
1:25.9	Santiago Aparicio got everything he dreamed of, and he worked hard for it.
1:30.3	But the problem was, he was still never satisfied.
1:33.3	We were going from nothing to have a billion dollars a year.
1:37.3	I was feeling like shit.
1:39.3	And it nearly killed him.
1:40.3	If I didn't go to the cardiologist, to be honest, I think I would truly die.
1:45.8	My wife and my family took me into a room and mentioned, like, you need to choose.
1:50.4	If you stay in your company, you're going to lose his whole.
1:52.7	And that decision also nearly killed him.
	...

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