When I was a kid in Ohio, watching high school quiz teams compete on WBNS 10-TV’s In the Know was a weekly ritual. It was fun and exciting, but more importantly, I felt in my bones that I would be on ITK someday.

It was like that — more a premonition than just a goal. This game was for me, and these people, weirdly, were my tribe.

So I made the Whetstone team as a sophomore, had a great run until late in my senior year, when we imploded in the quarter-finals at the hands of our archrival, North. Brutal.

This horrible defeat did not end my trivia life. When I got to college, College Bowl was a long way from its glamorous heyday in the 1950s and ’60s as “The Varsity Sport of the Mind.” But Amherst had a club team, I made it, and in our only actual game, we beat the faculty before an audience of students, professors and staff. Fun.

Then, in preparation for a trip to LA, I bought a Sunday LA Times at Out-of-Town News in Harvard Square. On the front of the Classified section were ads seeking game show contestants. Right there on the page was the Jeopardy! logo and a phone number. A few days later, I was sitting in a production office at a classroom desk taking the 20th Century, paper-and-pencil version of today’s Jeopardy! Anytime Test. That night, they called me at my fleabag Hollywood hotel and told me they had an opening the next day. A little while later, Alex was congratulating me for winning. As returning champion on the next show, I crushed the Jeopardy! Round…and then Jonathan, the pedi-cab driver from Honolulu, got the hang of the buzzer in Double Jeopardy! and beat me.

One and done. But I will always be a Jeopardy! champion.

I went on to make the MIT College Bowl team as a grad student, but as the lowly fourth alternate. My knowledge was a subset of the team’s star, and he was faster on the buzzer. I bowed out before the first game.

Thus began my pivot to trivia impresario.

At some point during my tenure at JP Morgan, I realized that on slow market days, I could run a trivia game for my colleagues and clients by sending questions and receiving answers via the message function on the Bloomberg terminal. We had a lot of fun. I once gave players the names of four celebrity sex tape scandals and asked them to put them in chronological order. Our head of asset-backed securities research submitted an answer and explained that he had opted to put them in order of quality rather than chronology.

You might surmise that the frivolity and reputational risk of this activity would lead management to conclude that it probably shouldn’t go on. It didn’t. Then, during COVID, at a different firm, I did some Zoom trivia games, again for clients and colleagues. At that point, people seemed desperate enough for diversions to overlook the risks and the frivolity.

Then came my move to IRL.

I was on vacation with my family and we were playing trivia at Parker Pie in West Glover, Vermont. We had a fun pizza/bar experience…and I vaguely recall that we actually won that night. At the end, however, the host announced that while the game would go on as usual the following week…they didn’t have a host.

Did anyone want to host?

I did. It went great. I came up with the categories and wrote the questions with a focus on fun, keeping the evening’s proceedings on a friendly arc, and staying mindful of the audience. We had young and old, local Vermonters, vacationers from the flatlands to the south, and maybe a few Quebecois.

I loved it so much. It was a strange and wonderful combination of improv, speed-dating, board games, trying to remember that book you read in 6th grade, competitive trash talk…a carnival of wonders held together by people connecting questions with answers while connecting with one another.

And since the fall of 2024, I’ve done the same thing…mostly at bars, restaurants and performance venues near home in suburban Boston, sometimes on the road. We have families and singles and working professionals, some arts-oriented, some science-y, ranging from Boomers to Zoomers, sometimes with children in tow. In 2024 Liana Emley joined — from the audience, she played one night. It’s a great night out.