From Teacher to Trivia Host: This Man’s Side Hustle Earns Him $125/Week

High school teacher Greg Tipton repeats a question into the microphone as he hosts Trivia Night at the Angry Pepper Taphouse in Seminole, Fla. Tipton organizes Trivia Night every Wednesday as a fun side hustle. Aileen Perilla/The Penny Hoarder

As the teams arrive for Trivia Night at the Angry Pepper Taphouse in Seminole, Florida, they find Greg Tipton sitting at the far corner of the bar putting together the final touches of tonight’s game.

He’s dicing up sheets of paper to make answer slips, sharpening dull pencils, testing the restaurant’s audio system and checking his questions one last time. As he walks around the high-top tables and booths passing out packets filled with game supplies, he welcomes his regular players and encourages newcomers to give his game a shot. And when the clock strikes 7 p.m., it’s time for trivia.

Tipton hosts Trivia Night at the Angry Pepper every Wednesday. A high school math teacher by day, he uses his questions to put restaurant patrons’ knowledge to the test. This fun side hustle pays him an extra $125 a week.

“I care about the product,” Tipton, 33, says. “I want it to be good. I want people to have fun. I don’t want to mail it in because that’s not the kind of person I am.”

Your Friendly Neighborhood Alex Trebek

Trivia participants high five each other as Tipton repeats the answer to a question. Aileen Perilla/The Penny Hoarder

Tipton says he had no intention of being a trivia host. When he started picking up bartending and server shifts at the Angry Pepper three years ago, the restaurant already had one.

About a year-and-a-half later, the existing trivia host decided to move on, and Angry Pepper owner Al Cowan asked Tipton if he wanted to take over. Cowan figured that the public speaking skills Tipton had developed as a teacher would make him a great host.

Tipton thought it over and realized it was “a no-brainer” to accept the gig — it would allow him to make some extra cash that he could put toward supporting his family.

Learning the ropes was stressful — especially with a live microphone in his hand.

Early on, if he asked a question with any shred of wiggle room in the answer, he would get 30 pairs of angry eyes glaring at him after revealing it.  

Or worse, those aggravated people would march up to his corner spot at the bar and passionately defend their answers. Tipton credits the conflict resolution skills he uses with his students to amicably resolve these disputes.

“It’s kind of a natural transition,” he says. “Teachers have that command over a classroom. In here you have a classroom that’s basically eating and drinking.”

Over time, Tipton found his rhythm as a host and figured out what type of questions his players enjoy. Now he looks forward to Wednesday nights.

“When I feel like we had a good week of trivia, I feel really positive about it,” he says. “I’m like, ‘You know what, I think everyone had fun; we had good questions,’ and that’s a great feeling, especially when they come up to you —– being on a losing team  —– and they’re like, ‘Hey, I like your questions this week. That was fun.’”

It’s All About the Questions

Tipton keeps a basket of answer sheets and file folders for both regular teams and newcomers. Aileen Perilla/The Penny Hoarder

On Monday nights, the pressure starts to build for Tipton to start writing questions. He knows that if he comes up with two, he’ll get in the zone and be able to write the remaining 14.

“I have come up with these trivia questions,” he says. “There’s going to be a hundred people that are depending on me so they can have a good time, and I care about it.”

His questions start off easy and then get progressively more difficult. If they’re too tough in the beginning, players might bail. Part of Tipton’s job is to keep people engaged so they stick around for a chance to win the prizes (and maybe order another round of food and drinks).

Early in the game, Tipton might ask: “The TV show ‘That ‘70s Show’ was set in what state?” (Wisconsin)  

Then in the later rounds, he’ll hit them with something like this: “Who was Al Gore’s running mate during the 2000 presidential election?” (Joe Lieberman)

The questions that Tipton gets the most joy in creating are meant for the middle of the game, when he wants about half the teams to get them right. He calls these the “I knew that” questions, because that’s what the players say when they get them wrong.

For example: “What is the name of the famous house that architect Frank Lloyd Wright built in Pennsylvania in 1935?” (Falling Water)

Tipton describes hearing the mix of half the room cheering and the other half groaning as “a euphoric feeling.”

“It’s a good feeling because [the players] respect those type of questions,” he says. “I think in that moment, they realize that was a good question.”

Kevin Brahm, 28, who plays with friends under the team name “Vape Naysh,” says Tipton’s laid-back personality and knack for never asking dull questions keeps the team coming back.

“Every now and again, there are president questions where we’re like ‘Aw… I don’t know the 11th president off the back of my head,’ but he keeps it fun and keeps the game moving,” says Brahm.

Playing for a Little Respect Around the Neighborhood

Kevin Brahm and Tom Nahon sit outside the Angry Pepper Taphouse as they wait for the rest of their team to show up for the weekly ritual. Aileen Perilla/The Penny Hoarder

If you plan on playing trivia at the Angry Pepper arrive early to find a good table near an audio speaker. About 45 minutes before game time, teams of four to seven people start to take their seats and order beer and smoked chicken wings.

On any given week, around 15 teams compete for the top prize. As many as 25 teams play during the peak winter months when the seasonal residents are back in town.

And what do they win? The top three teams receive $20, $15 and $10 gift cards to the restaurant.

“It’s not exactly high stakes, but people like to come in first, second or third place,” Cowan says. “Every week they’re challenging themselves to get on the leaderboard.”

The competition is fierce, as players lean across the table to whisper to their teammates.

“What is the name of each of the seven dwarfs?” Tipton asks. The teams write down as many names they can remember on their slip, then hand in the answer.

The noise in the restaurant dims as Tipton reads the list, followed by an audible moan when he says “Bashful” and “Doc.”

Even the players feeling grumpy about getting the Snow White question wrong leave smiling —  as long as teams play fairly. But they don’t always — and one time that caused a fight to break  out on Trivia Night.

Rule No. 1 in bar trivia: using phones to look up answers is forbidden. One night, a rowdy group of non-regulars  came in and decided to play. They were answering all the questions correctly. Tipton determined they were using their phones to Google the answers, so he disqualified them.

One of the regular players confronted the cheating team and ended up getting thrown into a booth.

Tipton, the servers and other patrons broke up the scuffle. The cheating team apologized and never returned.

That’s about as high as the drama gets at one of Tipton’s Wednesday night trivia games. Most times, it’s just fun-loving folks testing their knowledge trying to answer questions like this:

“Who were the two people who served as Speaker of the House in the 2000s?”

And the correct answer is…

Dennis Hastert and Nancy Pelosi

Matt Reinstetle is a staff writer at The Penny Hoarder. His side hustle of choice was hosting trivia in bars and restaurants around Lakeland, Florida.