Annie Wickman shares insights from her journey as Google alum, first non-founder at Humu, and now Head of People at Character AI. Annie tackles our hardest questions in an unmissable episode. She covers the tensions between product-market fit and company culture, Character AI's unprecedented Google deal structure, taking the leap from people leader to a VC, and how to rebuild organizational trust.

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KEEP UP WITH ANNIE, NOLAN + KELLI ON LINKEDIN

Annie: https://www.linkedin.com/in/annie-wickman-3332731/

Nolan: https://www.linkedin.com/in/nolan-church/

Kelli: https://www.linkedin.com/in/kellidragovich/

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LINK/S:

Character.AI: https://character.ai/

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TIMESTAMPS:

(00:00) Intro

(01:17) Experience as First Non-Founder at Humu

(03:16) Early Employee Challenges & Responsibilities

(05:03) Why Annie Stayed at Humu for Four Years

(06:30) Product Market Fit vs. Company Culture

(09:05) When to Invest in Culture

(11:15) Hiring the Right Leaders for Company Stage

(11:40) Maintaining Morale When Company Isn't Winning

(12:42) Transparency as Trust Builder

(13:47) Sponsors: Planful | Metaview

(16:47) Rebuilding Trust Through Honest Communication

(19:11) Laszlo's Leadership Philosophy: Stretching People

(21:02) Annie's Experience in Venture Capital at Forerunner

(23:12) Teaching Founders to Fish vs. Providing Services

(24:51) How to Evaluate VC Opportunities

(26:09) Understanding VC Economics and Carry Structure

(30:10) Character AI's Unprecedented Google Deal

(32:56) Rebuilding Post-Acquisition: Product Vision Challenges

(34:13) Annie's Perspective on the Deal Timeline

(37:31) Post-Deal Reset: Napa Offsite and Hackathon

(39:29) Employee Ownership After Acquisition

(41:29) Building a New Culture While Keeping the Brand

(42:11) Wrap

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