Inflection Points

It’s been a nutty couple months.

Peter, Nick, and I sold Cloak! It turns out selling a company can keep you plenty busy.

The sale was a surprise ending for us. It’s also an exciting new beginning.

We didn’t need to sell; Cloak was happily profitable, and those profits were growing. We didn’t necessarily think we wanted to sell, either, at least at first.

However, as we began to plot out Cloak’s next eighteen months, we realized we were at an inflection point. Our investments in engineering automation had allowed us to run lean almost to a point of absurdity. But our leanest days were clearly numbered.

It didn’t take long to realize that we couldn’t take the next steps without growing our team. We needed to ship native apps for Android and Windows. We had to move aggressively to better serve our growing list of corporate customers. We wanted to scale our VPN network. We hoped to make our apps behave more gracefully even in the face of less common network failures.

All told, it was clear that Cloak in mid-2017 was going to look quite different than Cloak in early 2016. We assumed we would lead that charge… until a few potential suitors knocked on our door. The question then became: would we lead the charge? Or would we team up with a larger organization to make the next big push?

In StackPath we found an ideal suitor. Their plans nicely complemented and strengthened our own. They had a deep bench of business, sales, and marketing talent that we knew we needed. And it didn’t hurt that StackPath understood the value of what we’d built, and was willing to pay a fair price.

So here we are! I’m a full-time employee of StackPath. I have a boss. We have a mission. It’s the same as the old mission, only bigger. I’m excited to see what we can build.