Katie Dill, Paul Adams, Tom Conrad, and Others on Failure, Career Setbacks, and Learning from Mistakes

Katie Dill, Paul Adams, Tom Conrad, and Others on Failure, Career Setbacks, and Learning from Mistakes

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Katie Dill, Paul Adams, Tom Conrad, and Others on Failure, Career Setbacks, and Learning from Mistakes

Lenny’s Podcast — compilation episode · Source

A curated compilation of failure stories from seven product and growth leaders: Katie Dill (head of design, Stripe), Paul Adams (CPO, Intercom), Tom Conrad (former CPO, Quibi; engineering lead, Pets.com), Sri Batchu (former head of growth, Ramp), Jiaona Zhang (SVP Product, Webflow / former Airbnb), Gina Gotthilf (COO, Latitud / former Duolingo), and Maggie Crowley (VP Product, Toast). Central thesis: failure is not the opposite of success — it is the mechanism for getting there, provided it generates learning.

Key ideas

  • Earn trust before leading change (Katie Dill). Entering as a new design leader at Airbnb and immediately implementing changes without earning trust led to a direct team revolt — five designers in a meeting with prepared papers. The lesson: you can inflict change on people, or you can do it with them. Come in listening, not swinging; trust is the prerequisite for everything else.

  • Fail conclusively to learn (Sri Batchu). Growth experiments succeed ~30% of the time; failure is normal. The real failure is failure without learning. To make failure instructive, design experiments that fail conclusively: maximise the treatment effect by deploying every relevant tactic simultaneously. If the maximal version fails, you can definitively retire the hypothesis. If it works, optimise from there.

  • The equation matters as much as the execution (Tom Conrad). Quibi’s problem was not product execution — it was founding math. ~$2B was not enough content spend to reach subscription scale; it would have needed $6–10B. Pets.com was a viable business model that simply arrived two decades before broadband penetration. No amount of iteration rescues a fundamentally broken founding equation.

  • A-side vs. B-side careers (Gina Gotthilf). Professionals present only their highlights (A-side), creating a distorted picture. The B-side — dropped out of college, fired repeatedly, visa failures, six months unpaid, company collapses — is the hidden foundation of almost every impressive career. Careers are far longer than people think; “I blew it at 26” is never true.

  • Never do a side-by-side rewrite (Maggie Crowley). A classic PM failure: a six-month rewrite estimate became two and a half years, never reached feature parity, and burned out multiple team rotations. Root cause: arrogance + skipped discovery + no technical/design research into requirements. If anyone ever proposes a rewrite, do not do it.