Steppin' up

Rob Walling wrote a great post yesterday about building up your bootstrapped business over time by taking on smaller projects before diving into big ones. His post reminded me of Amy Hoy’s Stacking the Bricks philosophy, and I think that taking the approach of learning to walk before learning to run makes sense. Rob’s post made me reflect on my experience building products that have gone from producing no income, to putting some change in my pocket, to providing a nice income for my family, and I thought it would be fun to share.

My day job has always been building web apps, so my first side projects were also web apps: first, a community site, and later, a SaaS app for managing test plan execution for software testers. Those were fun, but never amounted to much.

The first side project I did with the goal of making money was a self-published ebook about building e-commerce sites with Rails. This was in 2006, when Rails was young, and that $12 ebook sold pretty well.

In 2007 I started freelancing full time, and I decided that I needed a product with recurring revenue to help even out my cash flow, so I started on Catch the Best, a SaaS app that scratched my own itch. I launched that in October of 2007 (working on in it part-time while working on client projects), and it got some paying customers from day one. The revenue from that app has never been large on a MRR basis, but it has been consistent, so I’m pretty happy having that as a cash machine.

In 2008 I was building a SaaS billing system in Rails for the third time. The first time was for Catch the Best, and second two times were for clients that had engaged me to build SaaS apps for them.
It occurred to me that other developers might be interested in buying what I had built so that they could save themselves the time of building their own. So I cleaned up the code I had written and launched RailsKits to sell that billing code to other Rails developers. I priced it starting at $250, and it was a hit. It effectively replaced my freelance income for a while, and while it doesn’t make as much as it used to (since other options for implementing billing have become available), it still is a consisitent revenue stream for me.

After RailsKits, I knew I wanted to do another SaaS project, and in 2012 I found the right one: Honeybadger – an application health monitoring service for Ruby developers. It has been an incredibly fun project with awesome co-founders. Since its launch in the fall of 2012 it has grown consistently, allowing me to cut back and eventually eliminate my freelancing business.

I didn’t set out with a plan to start with an ebook, then move to a larger product, then move to a recurring revenue product, but after having considered Rob’s Stairstep Approach and having reflected on the past decade of my own experience, I can certainly recommend going that route. It’s not the only way to go, but it does give you a variety of opportunities to learn how to find customers and sell something to them, and it can be a whole lot of fun.