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

Everyone’s chasing success — but what does that actually mean? Founders hit milestones, sell companies, and still feel unsatisfied. After 150+ interviews, the most consistent lesson is that most people are aiming at the wrong definition.

Here’s what we talk about:

• Why the traditional founder definition of success doesn’t hold up
• The dangerous feedback loop of external validation
• How imposter syndrome thrives — even after a $50M exit
• Why goal-setting alone can leave you feeling hollow
• The “post-success” slump that no one prepares for
• Why founders keep building (and chasing) after they’ve “won”
• A better way to define success that doesn’t move the goalposts

Cool Links:

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

Sponsors:

• Get a team of AI agents that run compliance for you at delve.co/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (1:00 ) Founders Who “Make It” Still Feel Unsatisfied
• (2:57 ) Defining Success: Objective vs. Subjective
• (4:27 ) The Founder’s Scoreboard and Moving Goalposts
• (5:11 ) The Emptiness After Achieving Big Goals
• (6:36 ) Internal Fulfillment vs. External Markers
• (8:23 ) Connecting Goals to Personal Fulfillment
• (8:44 ) The Search for Purpose After Success
• (9:25 ) Rethinking Purpose: Determination Over Destiny
• (10:30 ) Lifelong Fulfillment vs. Chasing Milestones
• (10:48 ) The Trap of Confusing External and Internal Success
• (12:01 ) Why Internal Success Makes External Success Easier

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.