I’m a part-time entrepreneur, and I’ve referenced in the past how I’m particularly interested in bootstrapping businesses. This fascination has actually come from the experience I’ve been having working with Justin, Austin, and Hunter on Anchor Tab. Bootstrapping a business is hard, because you’ve got to make hard choices about what to do and what not to do to get something out the door that people will pay for. From an operational standpoint, we have a very specific advantage over some other businesses out there.

Jesting aside, there’s a lot of skill and luck that goes into what I’ve taken to calling “Bootstrap Checkpoint Zero,” which is the point at which your business isn’t incurring any additional debt each month. We’ve reached that point with Anchor Tab.

The first phases of a bootstrapped business are all about learning. You more or less try to validate the broad idea with customers, then you sit down to make the MVP in a semi-vacuum. You debate over what’s actually minimally viable, whether or not to hire a professional designer, how much to budget for different aspects, and things are constantly changing.

Towards the end of the construction of our MVP, we entered a pilot stage and started bringing on our first five customers and try to take their temperature towards the product. It was a moment of truth to see how far off track we got in our MVP building. We got some great feedback during that phase that helped us prioritize the packaging that we did for our beta. Then we launched the beta. We gave around 30 users, mostly strangers, access to our product for free. We got more feedback. Some people loved it, some people didn’t, but people were talking us, and that’s what we needed.

So we went from having only the team poking around the product to 30 people in a short period of time – friends and strangers, doing it live. That can be scary, but it’s always needed. Here are some of the things we learned as a result:

  • The first interactions with the site were a bit confusing. You kind of had to poke around a bit and figure out what was supposed to happen next. We introduces a “first steps” section in our dashboard to help address this problem. Users are presented with the steps they can take to get started, starting with connecting an external service.
  • Our first stab at MailChimp integration was unacceptable. We knew it was dodgy because the MailChimp wrapper we were using didn’t support retrieving what lists existed on an account at the time or retrieving information about the user you were authenticated as. This meant hoop jumping and confusion for our users. So, we augmented the functionality of that library. As a part of our policy of giving back to the open source community that has so richly supported us, I made those improvements public (here and here) and now anyone can use them.
  • Figuring out how to access the tab embed code for your tab was unclear. This is the code you need to drop on your site for your tab to work, so it’s pretty darn important that you know how to get your hands on it. We had people creating tabs and then not having any idea how to use them! We put a pretty big plug in this problem by showing you a screen as soon as you create your tab that shows you your embed code and explains what to do with it.
  • Our messaging is unclear. This is actually a bit of an ongoing problem. As an example, we had at least one pilot/beta user expect our product to behave more like Hellobar, which it intentionally does not. Justin, Austin, and Hunter have been working on refining our messaging. They’ve been having conversations with customers to identify how the website has fallen short, and will continue to do so. We have new messaging for the landing page in the works as a result of these conversations.
  • We had bugs, lot of em. Our product runs in any number of different environments and has to behave and appear consistent across all of them. That’s hard. Things were broken in some cases.

The feedback resulted in a lot of work for me in updating the product, making it more usable, adding those finishing touches that make it feel like a coherent user experience all around. Then, we launched the MVP with a free month of service for all users who participated in the beta at the start of April.

At that point it was a waiting game. We released a whole batch of new features to our users and let them play with it. We just needed to wait and see what would happen. As it turns out, we had enough people enjoy the beta and sign on after the 30 day trial that we’re covering our monthly systems operations expenses. We’ve also continued receiving valuable feedback.

One of the best things at this point is that we’re not driving our priority list, our current and potential customers are. So, what tops our priorities at this point?

  • The messaging still isn’t completely clear. That’s numero uno.
  • We need to expand our services support. We’ve got two more on deck that should be going live soon, if all goes according to plan.
  • Proper behavior in tablet and mobile environments is clutch.
  • Better analytics.
  • Improvements to our NewRelic error monitoring to preemptively alert us to service failures due to bugs in our code. And fault handling behavior for situations where things have gone wrong.

The actual list of things on deck is much larger, but those are at the top for now. Exciting times are ahead, to be sure.

As always, leave me some comment love below. I’d love to hear from you. You can also comment in and up vote the Hacker News discussion. See you next week, kids.