How Did Office Hours Turn Garry Tan Into an Investor?

Garry Tan joined YC with no plan to invest. After he raised and quit his startup, he was really burnt out and needed to recuperate. He had no intention of ever becoming an investor, ever becoming a GP, or starting a VC fund.

It was still the era of consumer startups, when people said a co-founding team needed a designer. He was told he was a great designer and asked to help a bunch of YC companies design their homepages. He did so many office hours that his pet theory is maybe they saw how much work he was doing. They were already promoting other great people into investing partner, and they said they kind of needed to promote him too. He says he snuck right in. Asked whether he was actually good or just working hard, he calls it imposter syndrome at work, and says it worked out because he learned a lot. He loved that moment because he was the same age and still a practitioner.

He is now 12 years, 13, 14 years into the other side of that peer seat. He thinks the shift is probably the life of many an investor: you start out as a true peer to a lot of the people you back. Over the weekend he made a new website, did new interaction design, and says he was back.