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Navigating the Bootstrapper Thing 

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Any long time readers here will know that I’ve heard the siren’s call and I’ve been fantasizing about (and working toward) having a small product of my own. Like any other topic that I have an interest in, I’ve been absorbing as much as I can about what people are saying and what advice is being given about starting a small business online—and now I feel paralyzed. You see, this tiny, little industry is a bit of a self-serving ghetto.

I’ve always looked up to people like Marco Arment, John Gruber, and especially Maciej Cegłowski who have their own, small computer products that they use to support themselves. There are others, but these gentlemen have been generous with what they have learned while running their own businesses. They don’t talk about this stuff directly very often but they give talks and host podcasts and there is plenty of good advice given within. Its just not compiled anywhere.

So in my search for more structured information I came upon a large group of people talking about how they work for themselves supporting their own software products and I started reading what they have to say. Once I dug a little bit deeper it seemed that few of these people are actually running software projects, rather, they sell ebooks. Who do they sell these to? As far as I can tell, it seems like mostly to each other or other people who want to be part of their group. Look: I’m a white guy, from America, who went to a liberal arts college, of course I’ve thought about how it would be fun to write a book. But I’m not sure what I had in mind was peddling PDFs on the internet with a Buzzfeed-esque title and a landing page with testimonials from people doing the same. But still, I dug in a bit further.

I can tell you that almost universally all of these people’s first advice is to set up an email list. I am not against email marketing. In fact, I find some of the email solicitation that I receive helpful and appreciate that if I ever get tired of hearing from someone I can unsubscribe or, if it comes to it, I can create a rule in my email client so I don’t hear from them again. So, following the advice of the bootstrapper-shaman and you’ll soon find magic pieces of HTML and Javascript from questionable companies that you can paste into your website.

This is where things get especially shady and the advice moves from creating a collection of emails to doing things that I find morally reprehensible. This is where you’re directed to do things like have an email sign up form take over someone’s screen or give the personal information of people who visit your website to marketing companies so they can track them around the internet for you. This where you lie in that one-pixel corner of your website, waiting, ready to jump in and send them an email when they are most vulnerable. This is where you disregard someone’s privacy and patience so you can make a quick buck. This is the part that I can’t get past. I really wonder if the people who engage in this sort of behavior have never gotten annoyed with a bit of Javascript that rudely hides an article that they were reading, and if so, how they justify adding to it something that they have work on. Do they have bad taste and not find it annoying? Is it the “well, it works” or the “everyone else is doing it” mentality? Or perhaps worst of all, do they not see anything wrong with the lack of respect for other people they display?

There might be some good advice among these bootstrappers if I sift through what these folks say and filter it through my own view of the world. And maybe I was looking for shortcuts and I shouldn’t been surprised by the amount of crap being push by people doing the same. I’m not afraid of hard work; I enjoy it. One piece of advice given by almost all of the people that I do admire is this: build something that you need/want yourself. This is surprisingly difficult to keep track of, when you’re in the midst of coding or design, but hopefully I am.