The Hard Lessons Nobody Tells You When You Leave Corporate

Founder Unfiltered - What Founders Think But Never Say · Aug 13, 2026 · 36m

Leaving Uber was one of the strangest experiences of my life. One day I'm running a business line worth billions of dollars, the next I have no manager, no structure, no salary, and no idea whether I'm doing a good job. In this episode, part three of my conversation with Kassidy Warren, I get into everything that happened after I left: pitching my first consulting client on a $25k proposal I basically made up on the spot, learning to ask for what I actually want (something corporate culture trains out of you), and the existential wobble of defining success for myself for the first time.

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