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Shipping something to someone always wins — Kenneth Auchenberg (ex. Stripe, VSCode)

1.0K views · Jul 28, 2025 · 16:17 min · Watch on YouTube ↗
Takeaway

Build for sub-day OODA feedback loops with named real users — continuously viable products beat big-bang launches, especially in AI where iteration speed is the moat.

Summary

  • Kenneth Auchenberg (ex-VS Code team, ex-Stripe dev platform, now partner at Alico) argues product success comes from number of iterations, not big bangs.
  • Uses the skateboard-to-car analogy: build a continuously viable product (skateboard → scooter → bike → car), not wheels-then-chassis-then-engine.
  • At Stripe before locking trapdoor decisions they ensured: real users could see something, they could collect feedback, and they could ship an improvement — all in <1 day (Patrick Collison's bar: hours).
  • Practical rule: 'if you can't run your loop in a day, your process is broken'; you don't need to ship daily but you must be able to.
product-developmentiterationfeedback-loops
Original description
Learnings from building products at Stripe and applying them in an AI native word.

About Kenneth Auchenberg
Partner at @alley_corp, investor focused on backing founders building for developers.

Past building at @stripe, VS @Code, @microsoft and a few startups (acq)

Recorded at the AI Engineer World's Fair in San Francisco. Stay up to date on our upcoming events and content by joining our newsletter here: https://www.ai.engineer/newsletter