The a16z Show · Wednesday, August 12, 2026
Gary Tan reflected on his early career in 2003, a time when the tech bubble had burst and job prospects were grim. He had to choose between Microsoft and Expedia, ultimately regretting not pursuing his interest in web programming, which he felt he was abandoning at the wrong time.
“I had student loans and while I wanted to start a company, I just felt like I needed to get a job and then actually there were no jobs in the Bay, so it was kind of hard to believe actually.”
“And I sort of regret actually was I sort of chasing what was hot instead of what was clearly the thing I knew.”
“But I think that's embedded in this idea that you should just be earnest. Yes. And then you shouldn't follow what the crowd is saying, right?”