618: (Solo) What 5 World-Class Founders Taught Me This Year

Dec 30, 2025

This conversation dives into the world of resilience, featuring founders who faced immense challenges. Christina Karlsson shares how losing her brand twice led to clarity and rebirth. Phoebe Gates discusses building credibility from scratch, proving that one's journey matters more than last names. Jake Kassan reveals the unexpected emotional toll of exiting his brand. Tori Gill showcases a scrappy launch of a regulated sunscreen, while Amy Smilovic emphasizes community over copycats. Together, they highlight that failure often ignites new beginnings.

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ANECDOTE

Rebuilding After Losing It All

Christina Carlson lost Kikki K twice and rebuilt the business after near-sale and COVID disruption.
She reframed failure as a path to clarity and used those lessons to create a stronger model.

ADVICE

Earn Credibility By Building

Do earn your credibility by building things, not relying on background or name recognition.
Use hustle tactics like cold emailing and face-to-face customer outreach to prove your value.

INSIGHT

Exits Can Empty Your Identity

A big exit can trigger loneliness and an identity crisis even when financial worries vanish.
Money doesn't replace purpose, so build businesses that feed your soul as well as your bank account.

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