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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