Moneywise You’re Not a Successful Founder Until You Do This
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Nov 25, 2025 Many founders reach major milestones yet still feel unfulfilled. The episode explores why traditional definitions of success can lead to dissatisfaction. It delves into the emptiness that follows big achievements. Founders often chase external validation but struggle with internal fulfillment. The conversation emphasizes aligning goals with personal values to foster true satisfaction. By shifting focus from external markers to internal success, founders can enhance both their well-being and external outcomes.
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Feeling Empty After Big Wins
- Jackie describes hitting financial milestones and still feeling like an imposter despite a $40M exit example.
- She uses her feelings to question what success actually means beyond external signs.
Success Is Both Objective And Subjective
- Success can be both objective (milestones) and subjective (how you feel about them).
- Founders' scoreboards make external definitions of success especially seductive and ambiguous.
The Post-Goal Emptiness Problem
- Hitting an external goal often creates a distinct 'after' period that can feel empty.
- Objective wins don't reliably produce lasting internal gratification or identity completion.