CEO OS
People ·April 12, 2026 ·person

Jason Cohen

Who they are

Jason Cohen is the founder of WP Engine and a widely-read essayist on bootstrapping, pricing, and SaaS strategy via his blog A Smart Bear. He is one of the most honest voices in the bootstrapped software world — writing that sits next to Justin Mares and Patrick McKenzie as required reading for founders who don't take venture capital. For FeatureOS, his writing on pricing, positioning, and "roof shot" goals is directly applicable.

Core Ideas

  • Roof-shot vs moonshot — set goals you can actually hit and compound
  • Pricing is positioning — raise prices until losing deals feels costly
  • Charge more, say no more — the bootstrapper's discipline
  • Justin Mares — author of Traction, same pragmatic bootstrapping school
  • Marcus Sheridan — parallel school of content-as-distribution

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