Summary

Cantrill reflects on the paradox that while his career appears to have been characterized by perfect timing, it rarely felt that way in the moment. At each major career juncture—entering university during a recession, choosing software engineering amid predictions of offshoring, focusing on operating systems when Unix seemed dead, and founding Oxide when VCs dismissed hardware companies—conventional wisdom suggested he was making the wrong choice. His success came not from timing markets correctly but from having the conviction to pursue what he loved despite external skepticism.

Key Insight

What appears as perfect timing in hindsight is actually the result of having conviction in your work and resilience against conventional wisdom that tells you you're wrong.

Spicy Quotes (click to share)

• 4

  While this is objectively true at some level, it also gave me a double take: it rarely felt true at the time.

• 5

  Ed Yourdon had just written The Decline and Fall of the American Programmer, which boldly told any young computer science student that they were wasting their time—that all programming jobs would be done by cheap labor abroad. This argument felt wrong, but I was too in love with computer science to be talked out of it anyway.

• 4

  The conventional wisdom in the mid-1990s was that operating systems were done—that Unix was in decline and that the future clearly belonged to Microsoft.

• 7

  Sand Hill investors told us that 'we only fund SaaS companies', that our $20M seed round was 'too big', that 'there is no market.' (And most absurdly: 'if this is such a good idea, why are you the only ones doing it?')

• 6

  Six years later—with VMware customers wanting to get away from Broadcom and with frontier AI companies realizing that there is (in fact!) a lot of general purpose CPU involved in their workloads—our timing looks perfect, but in fact we are just resilient.

• 3

  Have the courage to follow your heart—and disregard what others say about your timing.

Tone

reflective