What I Learned Starting Two Little Startups

For about three years I worked really hard on a startup called Sett. It’s a blogging platform that did a lot of things very different, and, in fact, is still the blogging platform that my blog runs on because I’m totally unwilling to give up the features that I’ve gotten used to.

At the same time, it was a commercial failure, barely making more money than it cost to run the servers, and certainly not enough to compensate Todd and I for the work we put in.

I also run a site called CruiseSheet. It’s not wildly profitable, but it does consistently turn a profit, and I even have an employee to do all the daily tasks. These two startups are very different, and I’ve learned a lot through doing them.

The first thing I learned is that traditional “startups” are overglorfied, at least from my perspective. They seem to have morphed to become quite formulaic, and VC money has essentially turned them into “create your own job” instead of “create your own business”. Obviously this is speaking in broad strokes, but it’s how the definition seems to have shifted in San Francisco.

When we got to the point with Sett that it was clear we would need to raise money to become successful, I lost all interest in the business.

It was at that time that I realized that the value to me of having a startup wasn’t the shot at some huge payday down the road, but rather to have the freedom to create something by my own standards and on my own schedule.

So when I started CruiseSheet, I did it very differently. Rather than have a cofounder, I did it myself. Sometimes I would work like crazy for a week, other times I would do nothing for an entire month. I automated absolutely anything that could possibly be automated. I won’t even talk about some of the things I automated because I don’t want other cruise companies to understand how I do everything.

I also focused more directly on profit. There’s this Silicon Valley idea that scale is more important than profit, and that is certainly true for traditional VC-backed startups, but for a smaller startup it may not make as much sense. So my goal with CruiseSheet is to help people find the best cruise for them, and then to get them to book it.

There’s a stigma against lifestyle businesses, one that I bought into wholesale, but my mind has been changed on it. I like making money through my business, but I also just love having an open-ended project that I can pick up when I have the time and put aside when something more pressing comes up.

I’ve learned a lot of other things, of course: how to manage time, how to prioritize tasks, how to code better, and an infinite list of other things. The most important thing I’ve learned, though, is that the point of a business is to make something that efficiently channels your energy towards goals that are important to you. That may be building the Next Big Thing, or it may be creating a business that you can enjoy, be proud of, and make some money on in the process.


Photo is a rather fancy chair in a long-abandoned hospital in Taipei. I think if I lived in Taipei I might take it and restore it.






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