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From coast to coast, a scattered group of aficionados speak about an online trivia contest in hushed tones: Do you know about LearnedLeague? Its 30,000 members – you have to know someone in LearnedLeague to gain entry – competed in the 97th iteration of the contest earlier this summer.
They’re led by 51-year-old Shayne Bushfield, who started the league as an office contest in 1997, quit a job planning data centers for Microsoft in 2014 to run it full time and goes by the alter ego Thorsten A. Integrity in the game.
He spoke with Milwaukee Magazine about LearnedLeague and what makes a great trivia question.

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How did LearnedLeague get started?
LearnedLeague started as a little trivia game that I did with some people I worked with in the office in New York City in 1997. It was not online – it wasn’t even on email yet. We were playing these other games in this group I was running and we started doing trivia. And then it became a league, head-to-head, like it is now.
Then I left to go off to business school and restarted LearnedLeague with a website in 2000. But it was really small – maybe like 24 players, a super primitive website – and it stayed like that for quite a long time. When I moved to Seattle in 2008, it still had only about 180 players. It was just kind of a hobby on the side that didn’t take very much time, but it kept growing and growing. The modern era of LearnedLeague probably started around 2012, somewhere in that range. That’s kind of when it really started to spike, and 2014 is when I left my job at Microsoft to do LearnedLeague full time, as a job. I was working on the business side of things, in strategy and operations. You know the cloud, right? I worked for the part of Microsoft that’s responsible for the physical cloud – data centers and servers and networking.
It evolved fairly slowly from something that I just did as a hobby on the side to asking for donations to help cover my costs to being required to pay a little bit, but whatever amount you want, to now the membership levels. Each step of the way, there is basically a test like, can I do this? Can I actually, can I ask for money? Can I require money? Can I charge this much? And it kept growing at every stage. So it got to a point where I had to decide and either step aside from LearnedLeague and wind it down, because my job at Microsoft is getting bigger, or leave Microsoft and see what I can do continuing to grow LearnedLeague.
The symbolism of Microsoft data centers versus, you know, running your own trivia league – those are two very different things.
I mean, at the time it was not a hard decision, and it was the right decision. But it’s also insane to think about, like, that’s actually what I chose to do! And Microsoft, everything was fine there. But I left all that to run a trivia league online.
How big is LearnedLeague now?
There are quite a few members who don’t play every season, but the number of members is right around 30,000, and 28,380 were in the last league.
What is it about trivia that made you want to quit a pretty good job and do it full time?
Well, it really goes back to childhood, I guess. I did it with friends and did the high school quiz bowl stuff. But the thing that got me really interested in it, and this shows my age a little bit, is Trivial Pursuit. I was an only child, so the way I “played” Trivial Pursuit was basically just going through the cards, reading the questions and writing down the answer for each one. Then I flip it over and see how I did. And so I did that with, you know, card after card after card. But one thing that I did, and this kind of is reflected in LearnedLeague, is I would keep track of how I did in every category, so I had this data. I remember geography was my best category – I don’t know, 73% at that, or something. And the pink category, entertainment – because I was a little kid, you know, and they were all ’50s movies and stuff…
Yeah, pink and brown were always the worst for us!
Yeah, so I tracked all that. And that’s a big part ofLearnedLeague now, with all the data. And so I guess, LearnedLeague, for me, is kind of about two different things. It’s about trivia, and just having fun with trivia questions and answering trivia questions, and also having fun with stats, and data. Being kind of a stathead and sabermetrics, you can really dive into all that stuff.
It seems like there’s a sense of community that has developed around this – I mean, 30,000 people is a pretty good-sized city. Did that surprise you, the community that LearnedLeague has become?
I think of community and LearnedLeague in a couple of different ways. So there’s one LearnedLeague community of 30,000 members. That exists, and people meet each other in different places, and they occasionally find out the other person is in LearnedLeague and they connect that way. But that community is extremely loose, because there aren’t really a lot of mechanisms for connection. There’s a message board on the website and a private messaging function, but in the grand scheme of things that’s not actually used that much. But LearnedLeague is really this larger network of smaller communities that by and large a function of how people come into the league – somebody has to tell you about it and you have to be referred in order to join. So your friend is already a member and these networks develop, and that’s really the communal experience for most players. They experience the competition and they have a small group of friends or acquaintances who they interact with – branches of the same group. And they might communicate with Slack groups or text groups, things like that.
Why did you decide to use the alter ego Thorsten A. Integrity? It certainly lends this air of mystery and like, authority to the whole league.
It’s so dumb, that I have this pseudonym. I really should have gotten rid of it a long time ago, because it’s kind of embarrassing, especially when I meet people in real life and have this silly fake name. But it goes back to the very start of the league – you know, it’s just my friends and co-workers in this office on the 23rd floor of Radio City Music Hall. I’m running this contest and they all know me, so in order to have some sort of authority over this game, I felt like I had to come up with this fake alter ego. It’s not just Shane in charge of this, it’s Thorsten A. Integrity. I spent maybe a minute thinking about it and like, just threw it in one note to start a match or whatever, and it just stuck. And here we are 25 years later.
Kind of broadly, how do you view trivia from a game design standpoint?
So the trivia is kind of like a ball, and LearnedLeague is a sport that uses a ball, right? Like, basketball uses a ball in one way, football uses a ball in another way, baseball, etc. And so LearnedLeague is one way of using the ball of trivia and forming up in a game with rules and so forth. And what I like about trivia is the different ways that you can use that ball. There’s just knowledge, which isn’t so interesting to me, because, like, you know things or you don’t know things – that’s basically just taking a test. But what I tried to do with LearnedLeague, and what I think can make trivia fun, is if it’s a game where you can test yourself on knowledge and meta knowledge. So it’s not just what you know, it’s what you think you know, what you’re able to retain, what you’re able to pull, what you think other people know and using all of that to form a game out of it.
Just like, bouncing a ball is OK. But coming up with a game with rules to like, form up different ways to compete using that ball is a lot of fun. And so I’ve thought about it in the equivalent of, like, a three-point shot in basketball is just satisfying, you know? When you just shoot it from the top of the arc and you drain it, nothing but net, it just feels good, a tiny little jolt of dopamine. And you can get that same feeling with a really well written trivia question. Like, “What is the capital of Wisconsin?” Easy question. You know it, there’s not a whole lot of joy in getting that question correct. But a well formed trivia question makes you think, makes you recall something from your past, either about your life or how you learn a specific fact. It makes you think, “I should know this. So I’m going to try to figure it out.” Or it might even make you think, I don’t know this, but I want to know the answer. There are a lot of different ways you can come at it. But there’s always that dopamine shot at the end. And it’s just a little jolt, you know? It’s not an intense joy. But it’s just enough to like, make you want more.
I mean, maybe it’s a little jolt, but when I see an answer that I got wrong and just couldn’t think of, I’m like AAAAGH.
Oh, right, it can be the opposite, too.
Do you have a favorite type of question?
There are a lot of different ways to go about this. A really primo trivia question is like a really great dessert – too much diminishes it. With LearnedLeague, there are six questions in a day, and you can’t have six super deluxe questions in a day, because that’s just too much. You kind of have to temper it a little bit.
But the best kind of question, first of all, it can’t be too long. And it is something that is knowable and worth knowing – you know, interesting to know. And the question itself is written in a way that allows you different ways to come at the answer. So if you think of it as a big boulder that you’re trying to crack open, and there are lots of soft spots around it. And you can use your tool to kind of chip away at one part or chip away at another, or chip away at the ground underneath it – ruling things out. Having these different kinds of angles of attack, and not necessarily all of those angles of attack are the words of the question itself.
Sometimes you can get really juicy and kind of have meta clues, like what’s not in the question? There’s a word that’s conspicuously not being used. Like, I’m referring to a seagoing vessel, but I’m not using the word boat, you know, that might be because that’s part of the answer, or that’s a clue. Or it can get really creative and sometimes controversial, like, playing with the form and make it so the question rhymes, or the question is written in some meter, you know, or the question is written without a certain letter – all different sorts of things. It rewards a player for reading closely and identifying things. It’s something you can kind of sit with, and kind of luxuriate in, like, OK, yeah, this is something I can get to.
But LearnedLeague is for everybody. All you have to do is like trivia. There’s this impression that LearnedLeague is for elite trivia players – and yeah, there are many elite trivia players in LearnedLeague, no doubt about that. But it’s not for them. It’s for anyone who enjoys trivia, and the league is structured so that you’re playing against people who are roughly at your skill level. That’s a fundamental part of the design. If you like trivia but you think you’re not good at it – first of all, you probably are better than you realize. And second of all, that doesn’t actually matter a whole lot if you enjoy it. And if you’re OK with getting a lot of questions wrong, because that’s how it works, then I think you’ll like it.

