How I ended up at Apple (1999)

Click here to view all the articles about my Apple career.

I’ve interviewed hundreds of people while I’ve been at Apple. Unlike most new recruits, Apple was not a company I ever dreamed about working for.

I never wanted to work for a big company. Period. For me, a big company was one with more than 200 people. I found even companies that size were riddled with bureaucracy. You’d never talk to any of the senior leaders except during a Q&A at a company-wide event. I couldn’t fathom working at a company with more than 5,000 people like Apple was at that time.

Even if Apple were small, I had given up on them back in the mid 1990s. The last straw was my nearly $7,000 purchase of a PowerBook 5300— the worst computer I’ve ever owned. I later sold it for $500 just for the display. Apple’s system software quality was also at an all time low. For six months, I tried to switch to Windows but failed. It was a pretty dark time in general.

In between jobs, I took a contract job doing documentation as I…