YC’s Group Partners share their worst investor meetings

by Garry Tan8/17/2023

Mind games. Awkward power moves. Investors showing up hours late, only to make no effort to seem interested.

Before any of us were Group Partners at YC, we were founders. We know how it feels to be in the hot seat when you’re raising money, and we’ve seen just how many ways an investor meeting can go wrong.

For this latest episode of Office Hours, the Group Partners are sharing stories from their worst investor meetings. We’ll outline some of the weird plays we’ve seen investors try to pull — but we’ll also confess times that we, as founders, bungled meetings we could’ve nailed. We’ll discuss what differentiates a truly great investor, and shed a bit of light on something we rarely talk about publicly: the YC Investor Database.

Why share these stories? Because if you’re prepared for the worst, you’ll be better off when it’s your turn. We’re at the beginning of a shift in the way business is done, and the kinds of games VCs played in these stories just aren’t going to work anymore.

At the end of the day, just remember: the point of your startup is not to raise money, impress investors, or gain status. The point is to create something that actually solves a real problem. We’re here to make something people want.

This is the second episode of Office Hours. Find the first episode here.


  • Garry Tan

    Garry is the President & CEO of Y Combinator. Previously, he was the co-founder & Managing Partner of Initialized Capital. Before that, he co-founded Posterous (YC S08) which was acquired by Twitter.