** 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.