8 min 19 sec

Teacher Makes Money Asking Questions Outside the Classroom

A West Virginia high-school teacher hosts trivia night for extra income—then earns a share for other hosts who use his equipment.
Events Low Startup Potential Service Teacher Hustles

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What It's About

A teacher takes on trivia night!

Business Model
Skills Required
Trivia Building & Organization
Profit Potential

Words of Wisdom

If you want to become an entertainer, get comfortable in front of a microphone, work on your delivery, and get good at being in front of a crowd. Only then, do you buy your own equipment. You can always make arrangements to get the equipment you need as you get better (just like the two gentlemen in this story did!).

Fun Fact

There’s a lot we can learn from Brad, whether from his example or from one of his trivia games. Trivia games have been extremely popular, with several mobile trivia game apps consistently having more than 1 million players. Guess we are all a curious bunch!

Notes from Chris

Episode 770
Growing up, Pittsburgh native Brad Bonenberger always liked hosting events. In high school, he co-hosted his own Public Access TV show where he would give a bi-weekly recap of athletic events. When he attended West Virginia University, he joined the college radio station and became the play-by-play announcer for the women basketball team. After graduating, he took his talents to an award-winning radio station, where he worked as a DJ.

While Brad enjoyed his job, he decided to pursue a further degree in secondary education at his alma mater. This would give him the skills and experience to teach high school students, which is what he does now full-time.

But as he started his graduate studies, he needed extra money, so he moonlighted as a club DJ. During one of his gigs, Brad stopped by a club, which was coincidentally hosting a trivia night. Intrigued, Brad spoke to the host. He thought that this line of work could be especially suitable for him given his background. If it worked, it was also something he could count on each week, which was nice since his income at the time was sporadic.

As he left the club, Brad started formulating a plan to land clients who would hire him to host trivia nights. He started by reaching out to his contacts in the bar and restaurant industry. From there, he was able to get recommendations and the first few gigs coming his way.

Before long he’d achieved his goal of hosting trivia three nights a week, so he started wondering what he could do to scale up his business.

He had some good gigs, but as he says, “good is only good until you’ve had better.” He started climbing his way up to more established outfits. At one of these events, Brad started meeting players who wanted to know if they could get involved in trivia game hosting, especially since it looked fun and was profitable. One of them was willing to commit, so Brad thought about what he could do.

They ended up making a simple arrangement—his partner would secure his own gigs as an independent contractor while Brad would loan him all the equipment he needed for half of the revenue he made. Shortly after, Brad came across someone who was interested as well. At this point, not only was Brad making his full share of the 3 shows he hosted weekly, but also half of the revenue that the other two contractors made from their own shows.

As he gained more experience, he was able to gauge the type of questions that his audience would find compelling, and the manner in which they were asked. Becoming a better writer was essential to ensure that these questions were elegant yet witty, and Brad put in the work, researching and writing 60-75 trivia questions weekly. The average game he hosts accommodates about 8 teams and 55 players, but after getting better, Brad quickly found that he could host games with over 100 players easily. Although he had started out hosting the events at casual clubs and restaurants, Brad now has no issue delivering at weddings and corporate events as well.

From mics, mixers, and powered speakers, the list of equipment that one requires to host events can add up. Brad himself spent about $1,000-$2,000 initially to ensure that he could provide a good experience for his clients, and that has certainly paid off. He now charges a bar $150-$175 nightly, and a bit more for corporate events.

He’s proud to say he never cancels no matter how small the crowd is. He also hosts a customer appreciation day twice a year. He puts up a $1,000 prize purse for this game and teams up with local liquor reps to ensure that there would be merchandise for the raffle and prizes.

It’s a no pressure side hustle, and Brad is enjoying himself. As he says, quoting from a Beastie Boys song, “my job ain’t a job, it’s a damn good time.”


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Become comfortable in front of a microphone, work on delivery, and get good at being in front of a crowd. Then, buy your own equipment."
—Brad Bonenberger #SideHustleSchool

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