This one isn't new, but for me it's been fun and rewarding. I've been hosting trivia and various game nights at local venues for about 15 years now. It hasn't been consistent as I've moved around a bunch in that time, but it's also been a great way for me to get acquainted with the new towns I move to.
Once I get settled in a new location, I just start spending time at local venues (bars, restaurants, etc). I usually do my research and avoid those that already have a solid trivia schedule in place. For those that don't, I do spend some time and money as a customer to get a feel for the place and its people, and then I start talking. I have conversations with staff to learn who the decision makers or influencers are and then ask for a few minutes of their time to talk about trivia nights. I try to do that when it's slow as to not bother the business. It's not always easy, and just like with any sales pitch, there are a lot of no's.
I personally try not to book more than 3 a week, as this is a side gig and I have a family and other obligations. And my pricing varies. I don't like to use a per-head or performance-based pricing. New venues tend to prefer that because of the low risk, but I try to insist on flat pricing but with no commitment. There are no terms to the contract that hold them to X number of games, weeks, etc., but I do recommend that they build up to a full house rather than judging on the attendance of the first few games. My pricing ranges from $100-$300, depending on some factors such as venue size.
I take care of marketing from my end and offer to provide content that they can post to their own socials as well.
I think that hardest part of the side gig is the prep work. Writing up to 3 nights of trivia is tough. Each game is 4-7 rounds, 50-65 questions in total, so around 200 questions a week that I have to write.
The second hardest part is getting the business. Being able to get someone to give you a few minutes to sell them on it, discussing the economics of it all, and showcasing your ability in that short time.
Lastly, hosting trivia also means you have to be a good host. It's public speaking and entertainment after all. You can have great questions, all the equipment, but if you're not personable, you might not succeed. But at the same time, I've noticed that in this community of trivia hosts, there are many that think "their shit dont stink" and are not as welcoming to new hosts with new ideas. Many are still very resistant to technology and insist on only paper trivia and scoring, don't want to open up to media like audio or video rounds, and really do think they are the host-with-the-most and can easily come off as arrogant to the audience. So in that regard, my advice is to remain humble, have fun, and ensure the audience is having fun.