The Empty Nest



I’m always a bit depressed after the last dinner of the funding cycle. In years past, I’d plan a vacation starting the next day—just to distract myself from being sad. I wind up liking the founders so much that I feel like an empty nester once the weekly dinners end.

We have a bench signing tradition, where each founder signs the bottom of one of our benches at the last dinner.

But this summer was slightly different. The day before the last din, I was already preparing to be sad and was talking to Paul about it. I realized that this time the cause was not just because I’d miss everyone but something more: based on past experience, I knew some of the startups would die over the next several months.

I don’t mean I was bummed from an investment perspective. We’re in the seed funding business; we don’t expect all of our investments to pan out. It was the founders that I couldn’t help thinking about.

Most take funding from us and show up with grand ambitions. They beaver away for the next 3 months and get swept up in this amazing wave of excitement, achievement, and sense of invincibility.

But startups are hard. If they weren’t more people would do it. And it’s usually the next year that separates the wheat from the chaff.

That’s why I was so pleased that Paul decided to give a talk at the last dinner about how not to die. This topic may seem too grim to be introduced during such a celebratory night, but I think it was exactly the kind of thing the founders needed to hear. Because it could prevent them from making mistakes that inevitably lead to failure. For example, founders may not have control over market conditions, but they can decide whether or not they go to grad school. After 5 funding cycles, I’ve seen some predictors of early startup death and Paul hit them in his talk, which he posted online.

I suppose ultimately running out of money is the biggest reason for failure. But that’s a symptom of some other cause and doesn’t usually happen if you are doing things right. I think one of the biggest things that kills startups in the earliest phases is not focusing 100% on the company. Paul wrote, “If you find yourself saying a sentence that ends with ‘but we're going to keep working on the startup,’ you are in big trouble.”

You probably won’t make something people want right away. It will take so much perseverance on your part that if you put yourself in a situation where the startup is allowed to fail silently while you are (fill in the blank) [back at school] [consulting] or [working on another startup idea with a friend], then it probably will.

My favorite sentence was, “So if you want to get millions of dollars, put yourself in a position where failure will be public and humiliating.”

All this said, I don’t blame the founders if they try hard and fail. They of course have to pay their bills. Never having done it before, some people can find a startup too overwhelming.

Paul already warned everyone that “bad shit is coming;” and it probably is. But so is some really great stuff too. Like closing a funding round, launching, getting users, moving into your first office, creating something really useful, starting to be well known…

Though I’ll miss them, I can’t wait to see what the future holds for the summer ’07 founders. Good luck!

The gang gave us this digital picture frame, with photos of everyone to remind me of them. I'll treasure it!

10/5/2007 09:08:46 am

great post Jessica, I like when people behind the scenes talk about the reality of their situations, it helps personalize and bring a sense of reality to things I hold in high regard - like YC. - Josh Kopelman's "Woulda - Shoulda" posts about missed deals have the same effect.

Paul's essay on how not to die was a gem. His point about making your startup real to friends and family is a huge challenge for me right now. I often think my mother in law secretly feels like I'm just not working - instead of working on something that will be huge, that is hard. anyway - great post - thanks for sharing your perspectives.

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