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.
I started my own bartending business on the side for some extra cash. While it doesn't provide me with a ton of money, it has let me learn some good business skills and pick up few hundreds bucks a month. Plus, it's the type of business that face to face, can't be replaced with an app, and gives me something to improve on.
Lifestyle businesses really are the best. Who wants to drop dead of a heart attack chasing six figs?
So much sanity!
It feels like a backlash against the lifestyle business idea started right after Ferriss' Four Hour Workweek. The first backlash was that he was lying; there was no such thing.
The next backlash was that ok, there could be businesses like that. But you were a loser if you didn't want more. That backlash never seemed to end.
I'm also in a place where I have a business that throws off a nice living without my doing all that much. If I automated it more, I'd do practically nothing. Yet I'm feeling shame because I just don't want to push it to "eleven", build an impenetrable "moat", nor do I want to chase my "dream", my "calling", my "mission", my "why", or any of the other junk that the YouTube gurus throw around.
I kinda want a solid, reliable income stream while looking suspiciously like an early retiree to the unaided eye. My business helps people (as most businesses do), so it also gives me a source of pride and identity. But I don't know why it should also be a source of stress, or poor health, or should reduce my freedom any more than the absolute minimum required.
It's nutty that we're now supposed to feel bad about wanting something like that.
What we should feel bad about is killing ourselves for a decade until our company sells for nine figures, only to be screwed out of everything because we didn't learn about board structures and cap tables until too late.
I totally agree. Slightly off topic but Cruses are hugely damaging to the marine environment. I wouldn't be proud of a service like CruiseSheet no matter how much money it made and how much I automated it.
Since the term “lifestyle businesses” has such a stigma these days, I’m hearing the cool kids calling it their “side hustle”.
With a little encouragement from friends smarter than me, I've decided to pour some time into CruiseSheet and try to make it into an awesome cruising resource and a real business.
I think that cruises are the best value in travel, bar none, and are seriously underutilized by many people who could easily afford them, backpackers and independent workers especially. Right now all cruise sites are hard to navigate, hard to search, and geared only towards older people. I want to make something that's easy to use, makes it simple to find amazing cruise deals, and appeals to all ages.
If you haven't seen CruiseSheet in a while, a lot has changed. The biggest new feature is an amazing customized newsletter. Put your email and home port in, and you'll get a weekly update on the best deals in your city, your region, and all over the world. (Popup box for the newsletter shows up after 30 seconds)
I get a lot of newsletters, most of which I didn't intend to sign up for, and most of them are an imposition. If you're interested in cruising, this is going to be a newsletter that you look forward to receiving every week. So far we've sent out about 5000, and the response has been very positive.
Zachary Burt dropped me a line a few days ago and asked if I'd look at his posting for a cofounder. I said sure, and we worked on it a little bit.
This is normally the kind of thing I'd keep to private correspondence, but Zack told me to put to put it up if I'd like to. Maybe it's useful to learn from -
Here's the original, unedited version -
Headline: Badass technical business-savvy dude looking for fellow programmer and business partner to hack with all day.