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

Episode 62

** 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.

Published on 1 month, 2 weeks ago

Podcast Episode Details

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