How did this book come about?

In 2000, fresh out of college and with the bubble bursting, I got my first taste of a well-run formal software development process. I saw what it looks like to use bug tracking with a structured approach. At the time, I took it for granted, assuming that every company executed similarly, but then I was laid off. I quickly learned it was the exception rather than the rule.

At my next job, the company had hired an external development agency to build an application. As development started to make way for testing, I asked the team where I should report issues. They sent me a PDF, with instructions to print it out, fill it in, and fax it. That was the last time I took quality assurance for granted.

For the next eight years, I was fascinated with bug and issue tracking. As time went on, I started to notice how difficult it was to get smaller, less technical teams to invest in formal processes for quality assurance. There were tools, but they were all just too complicated or heavy for your average small team.

So in January 2008 I left my full-time job to build a bug tracker focused on small teams. In hindsight, I had unrealistic expectations, incorrect assumptions, and an incomplete plan of attack. I had a reasonable amount of development experience, but I only had a very loose knowledge of the steps needed to launch and support a production web application. Some things came easily to me, but most of the time I was covering new ground and figuring it out as I went along.

For years, I balanced bill-paying work with Sifter as a side project. As I transitioned to work on Sifter full-time, I made a variety of decisions and learned some lessons the hard way. I also got engaged, got married, bought a house, got a dog, moved a couple of times, added a couple of daughters to our family, and spent three years fighting medical issues that ultimately led to a left below-knee amputation. Eventually, I sold Sifter and, through the due diligence process, learned about even more mistakes I’d made. I had a lot of new lessons to share.

I took some missteps with Sifter, but I learned plenty about shipping software and making our customers happy. As I approach a decade of experience with SaaS, much has changed, but a lot more hasn’t changed a bit. I made a ton of mistakes, and I’d rather you make your own mistakes instead of repeating mine.

Starting your own company can look glamorous from the outside, but it’s messy. I’ve spoken with quite a few other founders over the years, and if there’s anything everyone agrees on, it’s that things get tough from time to time.

In the decade before I started Sifter, I averaged a year and a half at any given job. With Sifter, I spent over eight years pouring myself into one project. That time has been both the most difficult and the most rewarding of my career. I believe many of us bounce from job to job looking for fulfillment when—for some of us—that path may have less to do with finding the right job and more to do with pursuing something that moves us.

I don’t know whether you’re in the same boat, but I hope this book can help you on your journey. Mine wasn’t a walk in the park, but it was worth it. Looking back, I know that if I were to do it all over again, it’d be much easier the second time around—and that knowledge is what this book is about: it would be easier for me on a second pass. So I hope this book can help make it easier on you as well.