The co-founder I didn't pick

There were two of them, in the end, and I could only build the thing with one. Sam I'd known since university. He was fast and funny and had a way of making a whiteboard session feel like a heist movie. Elise I'd met at a meetup in Toronto four months before. She asked one question at the end of my talk that I couldn't answer and then bought me a coffee to tell me why. I want to be honest about how I made the decision, because I told myself a lot of stories at the time and most of them were flattering. I told myself Sam and I had "chemistry." I told myself Elise was "a bit intense." I told myself that with eighteen months of savings and no revenue you need someone you can laugh with at two in the morning. What I actually meant was that Sam agreed with me and Elise didn't. We built the company, Sam and I. It went the way a lot of them go. Eighteen months became eleven because we hired too early. We had a good launch and a slow spring and a summer where we both stopped saying what we thought. Sam wanted to raise. I wanted to cut. We compromised by doing neither, which is the compromise that kills you. The last real conversation we had was in a parking lot in Mississauga after a customer meeting. It had gone fine. The customer had said "let me think about it," which he'd also said the two times before. "You know what your problem is," Sam said. It wasn't a question. "Tell me." "You wanted a co-founder who'd never tell you your problem." I've thought about that sentence more than I've thought about almost anything else from those two years. He was right, and he was also describing himself. We'd both picked each other for the same bad reason. The company wound down in October. It was undramatic. We paid everyone what we owed them. We sold the customer list to a competitor for enough to cover the last month's rent. Sam went to a big company in Waterloo and is, as far as I can tell from his posts, extremely happy.

Elise, meanwhile, had built something. Not the thing we'd talked about; something adjacent to it, in a market I'd dismissed in that first coffee as "too small." It wasn't too small. It was exactly the right size for one very stubborn person to own completely. I emailed her about a year later. I said I'd been wrong, about the market, about a few things. I asked if she wanted to get a coffee. I did not say the phrase "no hard feelings," because I felt fairly certain the feelings were mine to have. She wrote back the same day. She said sure, and she named a place, and then she wrote: "For the record, I'd have driven you crazy. You weren't wrong about that part." We met. She was exactly as intense as I remembered. She asked me three questions I couldn't answer about what I was planning to do next, and I found that I had a pen out and was writing them down. I'm not going to tell you we started a company together, because we didn't. She doesn't need a co-founder; she's said so, and she's right. But I send her my plans now, before I show anyone else, and she sends them back covered in comments, and the comments are never kind and always correct. I built the first company with the person I wanted to be liked by. I've said that to Elise and she says it's the wrong lesson too, and that I should stop looking for lessons and finish the spreadsheet she asked for. It's due Friday.