Startup Trail is Oregon Trail for tech policy wonks

My setup was made public and it only took me about 25 minutes to get it done. I don’t remember what the company does, though I don’t think it really matters. I own 16 percent of the place, but after making some rash decisions about a legal fight and opting to set up a local office in India, the company is basically out of cash. However, users love us! So the future is bright for… whatever our name is. Does not matter. In a minute, I’ll start over and try something else.

I’ve spent too much of my day today playing start patha new browser game created by the technology policy website techdirt and Engine, a DC-based startup business group. The two organizations created the game, as by Techdirt Mike Masnick says so, to give people a little insight into the kinds of political decisions startups have to make, and why they’re rarely as easy as they seem. Especially for small businesses that don’t have the seemingly endless resources of Google or Amazon.

At the beginning of start path – which definitely has echoes of oregon Trail, and Masnick told me that the debate over whether dysentery should be involved raged all night before launch: You pick what kind of founder you want to be and where you want to be placed. I chose Mike, who has wealthy connections, graduated from “an elite institution with a reputation for producing startup founders,” and sounded pretty much like most of the Stanford graduate startup founders who walk Palo Alto. I chose to settle in “University Park”, where there was a lot of cheaper talent but not as many investors as I would have found in “Big Tech Valley”. In fact, I never got to choose what my company does because it doesn’t really seem to matter. Most new companies deal with the same things.

From there, my life as a founder became an endless series of questions, each one competing for my money, my time, and the talent of my team. Every time I made a decision—to fundraise instead of hiring, or to pursue content moderation issues instead of spending my limited capital to work on them—the meters on the left side of the screen moved. One tracked my financial health, another my user growth, a third my technology and talent. And underneath them all, three slowly disappearing clocks reminded me that time and energy are finite and I can’t do everything at once.

The biggest point of the game becomes clear pretty quickly: doing the right thing is hard, even when it’s obvious what the right thing is. (And it’s usually not obvious.) Even when faced with what seemed like easy options, like telling users when I’m going to turn over their information to law enforcement, I had to consider the time, money, and potential downsides of that decision (Pick a fight with the FBI). It’s a bit of a waste of time). When I decided not to worry about the competition, because all the CEOs of startups tell me they’re not worried about the competition, my competition finally crushed me. I had to decide who to raise money from and how much to raise, all with no idea what geopolitical or regulatory issues might come up down the line. I pulled out of Brazil rather than comply with a terrible new regulation, but I’m still not sure I did the right thing.

Image: Boot Path

techdirt has worked on games like start path before, mini-simulators intended to help people understand the complexities behind news topics. “We found that games as a concept are a really interesting way to explore difficult ideas, difficult political ideas, and also play with the future in general,” Masnick told me. In too many cases, he said, “everyone has their position and they’re really entrenched.” But when it comes to games, “just because of the premise, you’re saying, ‘Okay, put yourself in this other role. What would you do?'” techdirt ran a simulation, for example, to learn how misinformation could affect the 2020 election, and got some… discouraging results. And it is Magic: The Gatheringcard game style based on a CIA training program still a fun way to spend the night. Going forward, Masnick said the team is hard at work on an even more intense game dedicated to trust and safety issues.

When you get to the end of the game, you can share how it went. You get scores in each category, plus an overall score of five unicorns. (I got four unicorns, not to brag.) And eventually, if you’re lucky, you can decide what to do: go public, get acquired, go private, or hire another CEO and hang out on a yacht somewhere.

Masnick said that if there is a perfect way to play, even he doesn’t know what it is. “I know exactly how it’s scored, I have access to it, and I have no idea what the best path is,” he said. As I have played several times, most of the paths end in ruins. You run out of money, you get crushed by a competitor, some legal problem catches up with you and brings you down. In a way, I guess “patent trolls got you” is the 2022 version of dying of dysentery.

I haven’t met Elon Musk yet though. And if there’s one thing we’ve learned about startup life, it’s that eventually, if you grow big enough, you’ll run into Elon Musk. He is the real final boss of the game.