How to Get Started With Bootstrapping

Bootstrapping Resources

In the Scottish Ruby Conference, Tekin Suleiman gave a great talk about his experiences in bootstrapping a web app. At the end of the talk there was a question about further resources into the subject. I’ve been into this thing for years now (both in the form of building Wildfire, dribbling with personal projects, and now with Bear Metal), so here’s my take on the subject.

First things first: Tekin mentioned Amy Hoy’s 30x500 class and that has been my philosophical home in the field as well. I was fortunate enough to join the class early on, but even after several price hikes it’s worth many times its cost if you’re committed to bootstrapping. But you really, really need to be committed. If not (yet), you should still read her blog Unicornfree from top to bottom to gain lots of insight into all things bootstrapping.

Another commonly mentioned resource is the Lean Startup book by Eric Ries and the lean startup community sparked by it. My issue with the book for a bootstrapper is that in the end of the day, its ideology is still your normal startup mentality, only executed in a more nimble manner. That said, it might be worthwhile to read the book, if only to know what people are talking about when they mention the MVP or validated learning.

If you’re doing anything related to web, Patrick McKenzie’s blog Kalzumeus and the related podcast is an indispensable resource. Another one is Brennan Dunn’s blog and mailing list. Nathan Barry has also written a lot of good stuff on the topic recently.

If you’re a conference kind of person, there are a few that hit the soft spot quite nicely. Hoy organizes one called BaconBizConf in late May. Microconf (unfortunately this year’s conf already was in April) is another one that has received a lot of praise. LessConf was great as well from what I’ve heard but I believe the past one was the last one there was.

Random resource pointers aside, I’ll next delve into some (as random) details and lessons I’ve learned about bootstrapping.

Perils of starting with an idea

An old adage says that ideas are worth nothing, execution is everything. However, most people will only hang on to the latter part of the saying, not taking the first part literally. In her class, Hoy takes this one step further, explaining why starting by looking for an idea to build is actually harmful for you. The reasons for this are manifold.

First of all, it is not very likely that you have a unique, great idea that is also sellable. It is much more likely that someone already had the same idea, tested it, and found out it did not work. Second, thinking that the starting point of a company is an idea found in a flash of deitic brilliance is a very nice path to despair. This effect Hoy calls the idea quicksand. In it you think you find a great idea, sit on it, let it subsume you, and finally give up. It victimizes and paralyzes you.

Lastly, starting a company with an idea is very likely to cause your thinking to suffer from serious confirmation bias. You harvest information that supports your idea and dismerit or ignore cues that would tell you your idea is in reality a stinking, unsellable pile of yak poo. We all are affected by it and it’s really, really hard to avoid it. So do yourself a favor and don’t start bootstrapping with a ready-baked idea.

So what should I start with, then?

To sell anything, you need a market. You need an audience. An audience is a mostly homogenous group of people. Ruby developers. Web designers. Freelancers. Bootstrappers. You don’t necessarily have to be a part of the audience yourself, although that does help you both in finding the pains and later when you’re actually building your product because of your domain knowledge.

Once you have picked an audience, you can start finding out what really bugs that audience. Lurk in their forums, and spy on them for insight. What itches do they have, from which colossal pains do they suffer? This will form the basis for the business you’ll build.

Don’t directly ask whether they’d need this and that. Actually search for patterns and keywords in how they describe issues they’re having. This is what Hoy calls a Sales Safari.

Content marketing

One topic that pops up in almost every discussion about marketing effectively on the web is content marketing. What it basically means is that by providing valuable content to your audience you teach them and simultaneously build trust in yourself. This appoints you as an authority in the field.

An important thing to note is that you do not have to be a super expert in the field in question, just a notch above the knowledge level of your audience. This means you’re actually more likely to remember the pain and issues you encountered when you were in the same situation. For a seasoned expert this might be years in the past and thus something only vaguely in their minds. Thus it is easy for them to take many of the issues as given.

What you do have to be good at, though, is writing. If you have a big budget you can hire people to do it, but for a bootstrapped company at least one of the insiders needs to be a wordsmith. Sorry to break the bad news but there just isn’t a way around it. As said many times over, if you can’t write clearly, you can’t think clearly.

By writing skills I don’t mean writing grammatically perfect English (or whatever language you use to reach your audience). Grammar is important for sure, but much more important is communicating your ideas effectively. The most important thing to learn the ropes here is practice, but here are some resources you might want to have a look at for getting better at writing.

  • On Writing Well is a great general guide on writing effective prose.
  • Writing for Story by the two-time Pulitzer prize winner Jon Franklin is a succinct introduction to writing gripping narrative in non-fiction. Storytelling is one of the most powerful techniques we have to grip our audience and get our ideas through.
  • Breakthrough Advertising is a bible for writing effective ad copy. While you might never become a copywriter, your goals are very much the same. Unfortunately the book is out of print and very hard to get your hands on. You might (I’ve been told) find the full text from the net, though, using your favorite search engine.
  • Copyblogger (subscribe to their RSS feed or mailing list) is a blog about pretty much all of the above. The amount of new content there is a bit on the high side but the quality makes up for that.

Once you got the basics covered, you’re ready to get into the nitty-gritty details of teaching your audience. Neil Patel of Crazy Egg and Kissmetrics just recently published a free minibook called the Advanced Guide to Content Marketing. Aforementioned Copyblogger also has a series of articles about content marketing. One thing that invariably exists in these primers is building a warm email mailing list.

The Power of Email

As a geek it might be easy to dismiss email as a communication method as old-fashioned and something people mostly ignore. I mean, everyone prefers to get their daily RSS fix or (nowadays) read about your stuff on Twitter. Nothing could be further from the truth. Growing a list of email newsletter subscribers is by far the most effective method of reaching your audience. There are a couple of reasons for this. Firstly, it is way more personal. Most email list software lets you personalize your emails (so do collect at least the first name of your audience members, if only as an optional field), and if you write them in a conversational tone, the reader will react to them in a completely different manner than to a more generic form such as a blog post.

Secondly, in the spirit of permission marketing, everyone subscribed to your list has already given you permission to penetrate their email inbox. This is A Good ThingTM. You’re given a lot of trust. Just remember not to fail that trust. Always think how what you’ll write will benefit and teach the readers. If your newsletter is literally a collection of news about you, you, you, your readership will disappear faster than you can say MailChimp.

So, here were some random pointers for getting started with bootstrapping. Obviously, it’s a life-long path so taking up everything at once is pretty much a doomed undertaking (I’ve been taking Amy’s course at least three times already). So give yourself time, but get started now. And ferchrissake, don’t try to sell anything to consumers. Why? That’s a topic for another post.

Did I miss something? Anything else you’d like to read about bootstrapping? Drop me a note.