31 August 2021
My team lost its first three games of the summer camp season. A diverse group of boys all bunking in the University of San Diego dorms while the real college kids were back home with their families, we all had the same two goals: improve our basketball skills and win the championship. Losing three straight to start the schedule was not the way to snag a trophy.
We were coached by one of USD’s men’s basketball players. He knew what he was doing because he was playing college ball. And yet, we were losing. Two games a day, cafeteria food for breakfast, lunch, and dinner, and stories told only as boys could tell them in dorms reserved for kids much older than them. It was the time of my life.
Except for the losing part.
My team, a bunch of shirts in a sea of skins, was not bad. We had the big guy who could crash the boards. We had the point guard who could lead an army through a minefield. And we had the outside shooters. The guys like me. The guys who, posted like snipers on a rooftop, would fire from a distance. But we were losing, and we were mad.
So mad, in fact, that we asked the coach if we could throw his playbook out the window. To his credit, and perhaps as a representative showing of his actual coaching prowess, he said yes. He gave us the keys and told us not to crash the car.
And we didn’t.
We won every game. Two games a day for the remaining four days of the camp, and we won them all. We won our way right into the championship game. My parents came, ready to take me home only to realize they’d have to sit through one more game before it was time to leave. My sister was there, wondering what the big deal was.
The big deal was that this was the game. Everything every single boy in that camp had done had culminated in this game. Most of them sat in the stands with the parents, just waiting to go home, wishing they were still on the court. But not me. Not my team. We were the focus, the stars. The team that couldn’t win became the team that couldn’t lose.
But we did lose.
By a single possession, we lost, and the magic was gone. The focus was gone. My parents congratulated me and took me home. My team, and my five days living a college life as a pre-teen, faded back against the hills of San Diego, California.
The way I felt that summer, for those five days, were so powerful and painfully distant that I thought about them nightly. I thought about them all the way into adulthood.
In a phenomenal post about playing “the game” Ali Montag compares former high school football stars with today’s internet sensations. The high that comes from being wanted, needed, appreciated, and loved is hard to give up. But like with high school football, the glory days of internet fame are fleeting. And as Ali suggests, the fall from the spotlight is all the more amplified.
It’s easy to see this comparison take shape across what we now call the creator economy. Building an audience and performing for that audience is not a niche reserved for the few who have already cracked the inner circle. It’s everyone’s job every day on the internet, or so it seems. But outside the creator economy (or perhaps inside still depending on your definition), there is another form of glory chasing that is hard to shake.
I should know. I’m still chasing my glory days.
It wasn’t that basketball camp in San Diego. It wasn’t sports at all. What got me was way more technical. An app that people actually used and liked.
In high school and college, you learn public speaking. Or maybe you don’t because you managed to skip that class or take another elective. But most do. And most never use it in the way it was presented. Most people give presentations to a room of dozens at most.
I took public speaking in high school. I was forced to practice it in college. I didn’t expect to use the skills I’d learned. But in March of 2018, I found myself on stage in Berlin presenting to a room of more than 200 people. The secret no one tells you about public speaking is that it doesn’t matter how many times you’ve practiced your speech, you’re still going to almost freeze and die right on stage in front of all those people. Maybe that’s not totally fair, but that’s how I felt.
My old high school public speaking class carried me through the short talk. That short talk led to press. A lot of it. The app I built, at least on its idea, resonated. People began using it, tweeting about it, complaining about it. The complaints were, in my mind, the highest form of validation. People tend not to take time out of their day to complain about something unless they really care about it.
The app lived in a niche environment. In the Venn diagram of productivity tools and blockchain, there was Graphite and nothing else. This allowed it to gain adoption quickly. It became the top application on a particular blockchain protocol. In fact, it became the face of that protocol. For a while, at least. The protocol wanted Graphite featured at events, and they were willing to pay for me to go to these events and talk about this thing I built. I traveled to Oslo, to London, to New York City, to Austin, to San Francisco, and more. I gave talks about the power of user experience in a market where everything was so new that it felt like a research experiment. I talked about learning to code just so that I could build this app.
These talks generated even more press. They also generated interest from companies I was not well-suited to handle. Companies like CNN and Buzzfeed wanted demos. They asked questions I didn’t have answers for. I doubled down on trying to find those answers, trying to build solutions for the questions they asked. I committed to The Enterprise.
I quit my job to work full-time on the app, receiving grant money along the way from the protocol. In the circles I hung out in, people knew my name. I was asked to appear on podcasts and do live interviews. People wrote blog posts about my software, they posted on Reddit and Hacker News. Investors reached out to me.
And then, it all went away.
You know how when you think back to childhood memories and try to recount those memories only to find out you can’t remember the full details? That’s often how I feel when thinking back on Graphite. Am I getting the details right?
I doubt I am getting it all right. I am sure I bend the story one way or another at times. My memory of events is shaped by my emotional state at the time of the event. Could Graphite have continued? Maybe. Did I give up? Maybe. Was it really as good as I think it was in the early days? Maybe not.
These are the things that linger in the back of my mind, and I think they are the same thoughts and feelings that linger in the back of all entrepreneurs’ minds. These thoughts and feelings drive nostalgia, yearning for what once was. They result in an endless chase of the glory days. Like a broken former football star, re-living the moments when you felt on top of the world can be exciting. But when you snap back to reality, you’re left with two options:
Continue the chase or move on to something new.
I’ve done a decent job at moving on to something new, but I think about Graphite every day. I think about my missteps, I question whether I quit on it or not. These are the things you live with as a maker, a builder, an entrepreneur.
I once wrote that writers should let their old short stories die. They shouldn’t revisit them and try to revive them years later. And yet, as an entrepreneur, I am tempted every day to try again. I think we all are. This is where the term “serial entrepreneur” comes from. In some cases, though, it is literally trying again. It’s not trying again in the sense that you start another company. It’s trying again in the sense that you rebuild what you once had created, but you do it with the lessons you learned acting as the wind at your back.
I’m not sure that’s what I’m doing now. But I am building another document editor. Collaborative, private, blockchain-based. This time, I’m building it with a friend. With someone I trust. This time, I’m building it for the public good. Revenue comes last.