CEO OS
Learning ·April 12, 2026 ·reflection

Reflections

Where I Stand

  • I run a 5-8 person team. I'm in founder mode by default — not by choice.
  • Chesky's warning is about applying founder mode to the RIGHT things. I apply it to design, typography, and website polish. Not to distribution, pipeline, or customer conversations.
  • I don't have the "hire great people and get out of the way" problem. I have the opposite: I'm hands-on everywhere except the thing that's killing the business (getting people to buy).
  • Chesky rebuilt Airbnb during a crisis. FeatureOS has a slow-motion crisis — flatlined MRR, churn eating growth — and I'm not treating it with crisis urgency.
  • Skip-leveling doesn't apply at my scale. But the principle does: am I close to the work that matters most? Or am I close to the work I enjoy most?
  • Chesky says the founder's intuition IS the product. My intuition on product and design is strong. My intuition on distribution is weak — and I'm not building it.

What I Need to Change

  • Redirect founder-mode energy from craft to revenue. Spend 50%+ of the week on distribution, pipeline, and customer calls — not pixels.
  • Treat the churn problem like Chesky treated the pandemic: the defining moment, not a background metric.
  • Stop hiding in website improvements when stressed. That's manager mode dressed up as founder mode.
  • Build intuition for distribution the way I built it for design — by doing the work myself, not delegating or deferring it.

The Hard Question

If founder mode means staying close to the work that determines survival, why are you spending your days on the work that determines aesthetics?

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