Stand and deliver.
Posted by Justin in February 2021
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.
Ah, how easy it was to have such simple reasoning at the time. ↩︎
When I was an undergrad, I had eight shirts of the same color so I never had to make a shirt decision. I was honestly surprised when I found out people thought I only had one shirt. ↩︎
Degrees in biochemistry, philosophy, education, nursing. Highly varied careers and pursuits, success in all of them. At least sixteen Ironman Triathlons. Loved being an emergency room nurse. I’m sure I’m forgetting notable things. ↩︎
Washington the state in the northwest of the U.S. with the trees, coffee, rain, and polite people who won’t tell you what they really think. ↩︎
She could be great CEO of many other companies, too. What makes her so good at the CEO thing? I’ll keep learning more watching her in action, but one big part is her ego. It’s rare to see her ego and almost unheard of for it to interfere with her reasoning and rationality when making decisions even in stressful situations. She’s able to see everyone’s perspectives while understanding the underlying situation and aligning everyone in the same direction. In her last career, that was essentially her job: take a very complicated medical and human situation involving seriously injured workers where there is unfortunately no ideal outcome, identify the best way forward, align everyone including often doctors who disagree with one another, and see the situation through to until the injured person reached what’s called maximum medical improvement (MMI) in the healthcare industry. ↩︎