Chapter 9Innocence Lost

From idealist to realist, and the uncomfortable journey in between

Living in San Francisco and growing a company there was fantastic. It was everything I had hoped it could be.

But my early innocence and naïve gratitude also received a few punches.

I very much considered San Francisco and Silicon Valley a meritocracy where the best product, the best technology, and the best people always won. As Zendesk grew and we saw more competition, I started to see how investor “families”—angel investor relationships across startups and “Barney agreements” (“I love you, you love me”)—changed the competitive landscape in a way we were too young and naïve to really understand.

It was a surprise for us when brand-new companies claimed ...

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