The CTO Substack

The CTO Substack

The CTO’s Necessary Friction

When being “difficult” is exactly what your C-suite needs from you

Etienne de Bruin's avatar
Etienne de Bruin
Nov 12, 2025
∙ Paid

It’s 2009. I’m sitting across from my co-founder and CEO in our cramped office, reviewing our quarterly financials. Our SaaS company is barely three years old, pulling in about $1.8M in revenue with a team of 12. It is a very hot summer’s day in Old Town, San Diego. The air conditioning broke again last week, and I can feel sweat pooling at the small of…

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