How I Became an Entrepreneur

In 2005 I was graduating from NYU’s Interactive Telecommunications Program. If you had asked me at that point, I would have told you I wanted to go into research. I had spent the previous summer working at Microsoft Research in Redmond in the Social Computing Group, getting paid to invent, build and test cool social apps that were years ahead of their time. I’d even gotten to meet Bill Gates at a party. Although I was no huge fan of Microsoft, I was heavily under the spell of Redmond, of research, of that life.

The ITP Show is something that happens twice a year, at the end of each semester. Students present their projects to the public, who walk through the floor in a giant mass, interacting, comment, giving business cards, etc. I was presenting my senior thesis project, which was a hack of Google Maps that let anyone create their own map of locations from the web or from their phone via SMS (this sounds incredibly simple now, but it was about 4 weeks after Google Maps became hackable, and I’m fairly certain this was the first application out there to let users do that).

Amidst the throngs of people walking through looking at projects, a man stepped up to my table and asked me about my project. I went into my pitch, he listened, he asked some questions, listened some more. Then he said “That sounds interesting. Why don’t you come pitch it to me and my partner next week?” He gave me his card:

Fred Wilson, Union Square Ventures.

Now I had worked at several start-ups before going to ITP, and had loved it, but the thought that I could start my OWN start-up had really not occurred to me up until that point. This was 2005 — the new start-up economy had not come back after the disaster of the dot-bust, and there was really no talk at that point of “being an entrepreneur”. Entrepreneur almost seemed like a dirty word, a pejorative, or a word used by flakes.

But the minute Fred walked away, I had already forgotten entirely about Redmond and research.

The show ended, everyone recuperated, and I set to thinking about how I was going to pitch Fred and Brad at USV. I had never thought about pitching VCs before, and there weren’t any handy books written yet on how to do it (or good ones at least).

I went to Clay Shirky, my then-advisor for everything. Clay and I talked through the whole thing, went over how I should present it, and then did some calculations about how much money I would need to ask for to get to my first milestone as a start-up. Just relax, be yourself, tell your story was I think Clay’s advice.

On the appointed day, I went to Union Square’s offices. Fred and Brad walked into the meeting room overlooking Manhattan, we made some small talk, then I went into my pitch.

I had no slides at all. No powerpoint. No revenue projections. I just pitched the product, sold and sold as best I could. We used the site itself in lieu of a deck. (That detail strikes me as totally insane now).

Fred and Brad asked a lot of questions. They were hardball questions, really kicking the tires of the product, of the idea, of me, my vision, my capabilities. I was sweating and thinking as fast as I could. This went on for about 30 minutes. Then gradually the questions started getting easier. They became less pointed, more helpful. Then they switched over from questions into ideas, ways to build this bigger, ways to make this into a platform, etc. This is definitely a good sign, I thought.

Finally Fred put his pen down and said, “I love it. So how much are you looking for?”

Holy shit! I thought. This was the moment! Luckily I had carefully prepared with Clay for this. I bit my lip, took a breath, and said the number Clay and I had come up with:

I need two hundred thousand dollars.

Fred and Brad looked at each other. Everything stopped. Fred got up and started pacing the room. “Two hundred thousand dollars… We just don’t deal in numbers that low…” Walking back and forth. Brad closed his leather book that he had been taking notes in.

“I mean, maybe we could find some friends to put together a little angel round for you or something…” continued Fred. He was really trying to solve the problem. Oh shit, oh shit, I just totally blew this, I was thinking. Redo! Redo! But there was no redoing.

The thing was, I couldn’t at that point see needing more than $200k for this. All I needed to get the product off the ground and find the sweet spot, in my mind, was one developer and one designer. Asking for more at that point would have seemed like a waste.

What I realize now is that, coming out of ITP, I was embracing a lean methodology in a time before there was such a thing as lean methodology. I was saying “give me a team of two, lock us in a room, and we can iterate our way to the successful version of this.” The investment world — even people as enlightened as Fred and Brad — weren’t ready to hear that message in 2005. What they read into it, I imagine, is that I had absolutely no idea what building a start-up entailed, and probably could not be trusted (yet) with money. (That interpretation was also pretty accurate, by the way).

The meeting ended on friendly terms, and Fred and I kept up an email correspondence through the summer, but by fall things had moved on.

One thing that came out of it though was that I was absolutely, totally sure that being an entrepreneur was the thing for me.

And the following year, working with Steven Johnson and Cory Forsyth on our start-up outside.in, we came back to USV and we did get our money, in part building on the connection that I had made with them my first time around.