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.

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