Everyone has some amount of following life where it leads you. Success is like mass. A small success pulls us a little. More and larger successes have a stronger pull.

I was interested in computers as a teenager in the 90s. I’d also been unusually successful in school. In 1997, I was an eighteen-year-old junior in Electrical Engineering at the University of Washington.

I might have looked like your average nerdy kid. I might have been one since average nerdy kids are a lot more interesting than some people think. I also had a heightened question-everything instinct or rebelliousness, or combination of both.

I knew life was short. I wasn’t going to plod through life like the antagonist of the punk songs I listened to. I didn’t feel what made me happy was what made others happy. If you believe what makes you happy is different, does it make sense to do what everyone else does?

I dropped out of college and traveled for a few years, backpacking around Europe and the Middle East. Like many people, part of figuring myself out was learning about the world I lived in. I wanted to live life like the one shot it is. I worked as little as possible and spent less than $2,000 in two years. Why sell my time if I could just spend less money?¹

After two years away, I settled back into normal life. I’d missed the dot-com boom along with a few years of pop culture. I intended to keep exploring new paths I’d never considered as a STEM wunderkind. I applied to a creative writing program run by beat generation writers. It was a Buddhist college, too. In Colorado.

Unsurprisingly, I was also considering computer science (at a non-Buddhist school). Once accepted into the creative writing program, I had to choose: continue expanding or dive deep back into where I felt the most potential for myself. Not far beneath my exploratory hippydom was the same machinery as had always been there. I fully turned my attention to bits and bytes.

Having grown increasingly interested in security, I realized I wanted to be a computer security expert. To get there, I’d need the fundamentals. Once I started a C.S. undergrad program, I only wanted to go deeper. I got involved with research, did work I was proud of, collaborated with people I’d looked up to for years, had my choice of PhD programs, and got an NSF fellowship. Just like when I was a kid, I could be very academically successful, even if at the cost of other facets of life.

A couple of years into grad school, I lost the ganas.² Maybe I’d satisfied my research curiosity. Maybe I was afraid of the job I’d end up in.

While in school, I had internships with Mozilla and Google. Neither one left me excited for my approaching career. I worked with very smart people on interesting problems I felt good about helping solve, but I didn’t feel fulfilled.

My brain had never figured out how to be successful working for someone else. Thankfully, I got an unwanted kick in a helpful direction. Life and circumstances are complicated and I ended up broke despite my fellowship. I certainly could have stayed in grad school, there were solutions. I didn’t want them. I wanted to take my new clarity and get on with confronting my unsolved fulfillment.

I wanted to work, to build things people used, and to put my skills to use, but I also accepted the need to work for myself to be happy. I didn’t know anything about business. I took it on as a new challenge: I was going to figure out this whole business thing. I’d gone deep on computer security, could I go deep on business? It doesn’t work like that.

I proceeded to confront the very humanly complex business world with my problem-solving brain. Computers: easy. People: hard.³

I stayed focused on achieving financial freedom. I loathed the idea of wasting years and having to start over. I certainly would have welcomed crazy startup growth, but that wasn’t the goal. I just wanted to be able to choose how I spend my waking hours.

It took time, but I got revenue coming in. Over eight years, I put together an amazing team of about ten people. I never missed a payroll. That level of success, though nontrivial to attain, certainly wasn’t freedom yet. At least I had a talented group of truly good humans with me now.

I didn’t have a clear vision that could inspire me, let alone inspire a team of thoughtful people. I had (and have!) many ideas, but ideas aren’t worth much. What I lacked was a larger vision that could inspire people and drive an organization. True vision requires a broader understanding of the world than I have.

Enter Allison. We met in 1996 as college students. The moment I met her and saw her in action leading people, I knew I could follow her my whole life. She brings out the best in people who are willing to go there. I would have followed her regardless, but I also get to spend my life with her.

I’d been telling Allison for years she could run this company much better than I could. She was understandably skeptical. Unfortunately, it’s hard to explain the CEO job. Wouldn’t she need a technology background? No. What you need to learn, you’ll learn. Allison doesn’t have a problem learning new things and rising to new situations.⁴

In 2020, she did take over from me as CEO. What changed? Serendipitously (that is, due to COVID), the healthcare world changed and it became normal to run a medical case management business remotely. Before that, she was a road warrior spending many wasteful hours a day driving up and down western Washington.⁵

Soon she understood why I believed she’d be a great CEO of this company.⁶ Of course, she could only evaluate herself on her record and it was still early days.

Fast-forward to today. Everyone in the company is so much happier. There is inspiration. No longer only a group of professional colleagues, the team is a true team where each individual’s unique contributions are understood and appreciated. And we’re continuing to evolve our thoughtful and intentional culture as we grow. I didn’t see any of that coming a year ago.