One more card

I once met a founder of a new startup through someone I really trusted. My first meeting with the founder was great. I found the person to be deeply thoughtful about product, strategic about the business they were building, and opinionated about the future. I also really connected with the founder on a personal level; it felt like this was someone I would enjoy partnering with for a long time.

There was just one problem: I hated the category the founder was building in. Everything about the meeting felt great, but I couldn’t help but feel like I wanted to quickly pass on the deal because I had no interest in the category. I decided I was going to pass.

But before I did, I called one of my good friends, Semil Shah, who is also an incredible investor, and who I was sure had been in this situation before. I told him about the experience, and asked him if he agreed that passing was the right move. To my surprise, Semil suggested something different.

“Turn over one more card,” Semil suggested. “There’s something here you like and it costs you nothing to have one more meeting. In these situations, I always turn over one more card to see if anything changes for me. And I think you should do that here.”

So I took another meeting. And this time, we focused much of the discussion on my disdain for the category. And to my surprise, the founder made a very compelling case for why I was wrong about not only the category, but also the larger potential for their business, overall. In other words: not only was the category itself better than I realized, but the product the startup was building had much bigger ambitions anyway.

To make a longer story shorter, after several more meetings and more cards turned, including meaningful time spent in-person, I made an offer to lead the round, and we ended up partnering. I’m very glad we did.

And I’m also glad I learned the “one more card” lesson from Semil. Now, anytime there’s something I like, I remind myself to turn over just one more card and see what changes.