Things I’ve learned from my startup

Things I've learned from my startup

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Last year in May I got my BA in Physics and Philosophy from Yale; three days later Emmett and I officially started work on Kiko and became entrepreneurs. We've been working on Kiko full time for the past ten months, and during that time I've learned a few lessons as a young (newb) founder that I thought were useful enough to share. I'm not claiming to know it all about starting your own company, or even most of what there is to know (I still haven't made a dollar of revenue, sold a company, brought a company to IPO, the list goes on…), but I wish someone had told me these things ten months ago.

Don't hire/co-found-with your friends just because they are your friends.

I said this at Startup School last October. Here's my reasoning behind it: You want your co-founders/employees to reside at the intersection of really smart and really hard-working. Most of your friends probably do not live there. I went to a pretty decent school that claims to have lots of smart people, and most of my friends are not both really smart and really hard-working.

We're naturally inclined to do things with our friends: play racquetball, drink beer, etc. This is no different for starting a company. However, when picking co-founders, its human nature to either overlook or make excuses for your friends' shortcomings. This is really bad, because it can lead to situations where you think things like this: I know my friend, Gideon isn't the hardest worker, but he's really really smart. It'll probably be ok if we bring him on, I might just have to pick up the slack a little bit…

This might not seem that bad, but in a startup, everyone needs to be doing 150% of a normal job. And if Gideon is only doing 50% of his job, then you will end up doing 250% of a job. This will probably cause you to become very resentful, and you really don't want to be resentful about something that you're spending 15 hours a day on.

Furthermore, when you've had enough and you finally want to get rid of your friend, it becomes a non-trivial task, because you have to carefully balance his feelings against your need to divorce yourself from his incompetence. With an employee who isn't your friend, you don't have to worry about whether you'll fuck up the weekly poker game.

Things take longer than you think. A lot longer.

I'm specifically thinking about two very different things: software development and deals. As an example of the former, I'll give the example of rewriting Kiko. When we started rewriting, we thought it would take a month. It took six months. Obviously experience probably has something to do with the ability to produce accurate forecasts, however, we still routinely underestimate the time it takes to produce features. Now, when I ask Emmett how long something will take, I take whatever length of time he responds with and multiply it by three.

Deals also take a lot longer than I thought they would. Three months passed from the time we first started talking to our A round investors to the time we had the money in our bank. I don't think this was anyone's fault, but rather, the nature of any interaction between busy people working on many projects. Still, it would have been nice to know about the time frame I could have expected at the onset.

You'd better be able to get along with your co-founders.

This probably seems fairly obvious. What was less obvious to me when I started out was the sheer number of hours I would end up spending with Emmett. For the past few months, while we were coding the second version of Kiko, we were working 10-15 hours a day every day. That is a lot of time to be around another person, no matter who he or she is, or how good of friends you are. Emmett and I have known each other since the second grade, and went to college together, and we still get on each other's nerves. Still, my friends are constantly amazed that we can spend that much time together and not end up clubbing one another to death with a keyboard.

My only advice on this is not to sweat the small stuff. Don't let a disagreement over the company name or the logo color turn into a huge argument. Most of the time, when someone wants the webpage to be blue, and you want it to be red, it really doesn't matter very much at all.

Start simple, then go complex.

I'm not sure this applies to any fields at all outside of web development. Basically, when we built the first version of Kiko, we ended up building a hugely complex structure all at once. The second time we did it, we started out by building a very simple scaffolding, and then increasing the functionality piece by piece. I think Kiko is a testament to the second method being the better one.

Don't forget to have fun.

Don't drown in work. For a while, while we were working on the Kiko rewrite, we were working all the time. But right now we're starting to try and do more recreational not-work stuff, and I think that's been a huge boon to productivity. My advice is to try to do something physical: we play racquetball against Aaron and Steve from Reddit. Well, not so much "play" as "beat them every time."

I'm sure this list will grow a lot in the future, but for now this is all the advice I have. Hopefully this list will be useful to at least one other beginner entrepreneur out there.


I think you have a lot of good advice here. I have a good friend who started several company and his pet peeve has always been not to hire family or friends. he's very generous with his friends an family in many other ways but will not give them a job in his company. This way friendship is friendship and business is business. I also like your point about things taking too long. When you have a great idea and you work feverishly to put it out there, you feel like you've accomplished something huge. what you don't realize is that you've just begun. thanks for the food for thought. :)

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