Of apps, hype cycles and the entrepreneur's journey: episode three

The Museum of Pop Culture is a Frank Gehry-designed architectural grotesque situated on the edge of Seattle Center. While I do love some of Gehry's buildings — the Guggenheim Bilbao or the Dancing House in Prague are beautiful, for instance — The Museum of Pop Culture, however, is not a design that is universally beloved. Supposedly the building is supposed to evoke the image of a smashed guitar à la Jimi Hendrix. It's been Seattle's own beloved eyesore, for good or ill.

That said, the interior is pretty cool, especially the Sky Church, the concert hall/event venue smack in the middle of the smashed guitar body. That's where I found myself in 2012, attending the Seattle 2.0 Startup Awards. The app OneBusAway, an open-source transit app I worked on, was nominated for Mobile App of the Year. The primary creator of the project tapped me to go because he was too much of an introverted engineer and not at all interested in industry schmoozefests. He thought I was much better at small talk and networking. I think I was just better at drinking cocktails.

The acceptance speech I had prepared asked for a show of hands: "how many of you have built something where you were literally hugged by strangers when they found out you created it?" With OneBusAway, that was true for me. It was my first personal example of how technology could truly make someone's daily life better.

OneBusAway was one of the first apps that provided real-time public transit data to end-users: when your bus was really going to get to your stop, rather than when the schedule said it was supposed to arrive. Its creator, Brian Ferris, wrote his PhD thesis on the basis that it made transit more accessible and user-friendly. It made people want to use public transit more, because transit was perceived to be more reliable.

The data itself wasn't always reliable, though. We didn't control the data, and sometimes it was just wrong. Sometimes it said the bus was coming late when it was really on time, and people would end up missing it. In those cases, a user might email "app support" — which was just my personal email address. I can tell you that a lot of people are very angry when they miss their bus because of bad data, and they take it out on the app developer.

It was also a great lesson in user empathy. No matter how angry they were in their initial email, I would apologize to them that they missed their bus, and politely explain that the app was supported by volunteers and none of us were making any money keeping it up. Once they knew that, they were much more appreciative of the work we were doing.

This too shall pass, and repeat

Getting back to that acceptance speech. I didn't get to give it that day. We didn't win Mobile App of the Year. Later that night, we were told by one of the event organizers that we were a close second.

While I was writing this, though, I became curious — I didn't actually remember who did win that year. What is some new startup whose app we all have in our pockets? Actually it was a game, Battle Nations by Seattle game studio Z2Live. The game itself would itself be shut down in four years' time after Z2Live was acquired. Such is the way of many acquisitions in the tech industry.

In fact, the entire list of apps nominated are a fascinating time capsule into the tech zeitgeist of 2012. In one app you could share your location with friends and family; another was a text input technology for smartphones from the makers of T9. Both, you may imagine, no longer exist, but we use tech like this every day. The winner of "Innovation of the Year" was Kinect for Windows, which I'm not sure anyone uses. One of the awards was sponsored by Silicon Valley Bank, which companies used up until its catastrophic failure in 2023.

It's said that history doesn't repeat itself, but it often rhymes. It's also said that Mark Twain said that, but there's no evidence that he did. In any case, it's also said about history, and we're not talking about history here. If there's one overarching theme to these stories I'm telling, it's that more often that not, the tech industry does have a way of repeating itself. It's the same cycles of boom and busts, the same peaks of hype and the same throughs of disillusionment. Just the buzzwords change.

Beginning the entrepreneur's journey

That amount of cynicism only came with 12 years of hindsight. Back in 2012 I was still a fresh-faced entrepreneur. I went to classes learning how to be a tech founder, created my first company with a couple of people, and started on the entrepreneurial hero's journey.

Why did I start down this path? To use another poetry metaphor, why did I take the road less travelled by?

I was talking with another developer at one point, and we were commiserating on how many projects we've been on that ended or failed. I told him that I estimated that 99% of the code I'd written in my life is no longer used anywhere. He replied, "I would guess that 99% of the code I've written never even shipped."

I've been on many failed products and projects in my career, projects into which I've put in my time and energy only to see them come to nothing. It becomes disheartening after a while, because the products didn't fail because of the code. They failed because of all the other reasons products fail: timing, wrong problem, wrong market, wrong solution. All the effort I put into coding was negated by factors beyond my control, like a football running back whose 30-yard chunk play was called back for holding: a huge result that doesn't make the stat sheet.

If I was going to fail, at least I could fail on my own terms. I wanted to make my own mistakes.

I also wanted to create something else where I was able to experience the same connection with users that I had with OneBusAway, where I could potentially also make money doing it.

Over the course of the next four years I would be involved in multiple startups, some successes, many failures, and a lot of lessons. And I did make a lot of mistakes. Too many to mention here, honestly, and I don't want this to turn into some form of behavioral interview question where I'm using STAR responses and showing how I tackled problems and learned.

If there's another theme to these stories, I suppose it's that my life also tends to repeat itself, or at least rhyme. By 2016, I was again tiring of the industry and needed a change. Once again, I had gotten myself into a position where I was being led away from what I wanted to do, which was to build purposeful products that made a real difference in people's lives. Another step needed to be taken, and it was a chance encounter with former entrepreneur who convinced me what that step was going to be.