Back in 2012, my friend Pete (who was working at LinkedIn at the time) mentioned one of his former interns was a superstar. “I’d love to meet him,” I said. At this time, I didn’t yet have a fund. A few weeks later, we met for coffee, and I couldn’t believe how mature, curious, precise this kid, this person, was. We just became friends and he told me a bit about his work, dropping out of school, and his fascination with digital photography and manipulation.
Over the course of the next few months, we traded emails and coffees about his ideas, and eventually he settled on a bigger idea to build a next generation set of design tools. By this time, I did have a fund. Dylan, to his credit, was guarded about sharing his ideas too broadly. I respected that. I just wanted to invest in him, anyway. When I caught wind of his seed round forming, I remember texting and emailing him nonstop. I’m sure he was a little annoyed. I didn’t know what I was really doing from an investment standpoint at that time, but I just liked Dylan. Unfortunately, at that time, Dylan kept his moves very quiet and I wasn’t able to jam into the round. Now writing this today, I do remember texting him and he was very polite. I had to respect his desire to keep quiet.
Nearly two years later, Dylan emailed me about catching up, and the news was he was doing another bigger round and invited me to participate. We caught up and I heard about the plan, finally. It was great. I asked a few questions, and slept on it, and Dylan was very thoughtful about giving me time, answering any questions, and we explored a few ways I could help, even as a small part of a larger round.
I knew it was a good decision when I read how Dylan started his post this week about announcing his new product. “Today, after three years of silence and hard work, I finally get to announce the launch of Figma, a collaborative interface design tool.” That is true. For three years, Dylan resisted the press, the gossip rings, and the desire among some to announce half-baked things to the world. He was, instead, just focused on building a product to solve a problem he saw.
In these rare instances, the answers are generally very easy: “Yes.”
In this instance, I recalled what is my favorite AVC post by Fred Wilson, “Competing To Win Deals.” Every paragraph in this post is gold — and it’s amazing how many people don’t do any of these — but I want to focus on the last point:
10) Be prepared to lose the deal and if you do, lose gracefully. There are plenty of good deals out there. You don’t have to win them all. Lose gracefully and maintain your good relationship with the entrepreneur at all costs. They might come back to you on the next round.
I am not a big investor, but I knew Dylan, and I lost the deal. Maybe I wasn’t 100% graceful, but I was polite and Dylan is a class act. After that, Dylan and I continued to hang out, we’d catch each other late at night walking through Palo Alto or randomly on Caltrain, and we were simply just friends. And, like Fred predicted, he did come back to me in the next round, and I am grateful for that small gesture.