Conversations with Brendan Sargent

Today we’d like to introduce you to Brendan Sargent.

Hi Brendan, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I first started hosting trivia games in 2014, when I was teaching high school in Chelsea, Massachusetts. I was working for a company called “Pop Quiz,” and I had a couple of weekly games that I ran around Boston. I moved to Los Angeles in 2016 and hung up my cleats for a few years, not sure if I’d have the time or inclination to keep hosting games in a new city.

Fast forward to 2020 – basically as soon as the lock down began, I started writing weekly trivia games to play with my friends and family over Zoom. It began as a way to stay connected with people, and to be quite honest, a way to maintain my sanity to whatever extent that was possible. It expanded in size as the weeks went on, and eventually people were insisting on paying me to run these games. I wasn’t really interested in that; I had gainful employment throughout the pandemic & it didn’t feel right to be taking peoples’ money for myself when I didn’t really need it. So instead, I started collecting $5/player , and then the “prize” for the winning team was that they got to donate all of the proceeds to the charity of their choice. Eventually this expanded to splitting up the pot for the top 3 teams, so we could spread the love a little bit. By the time the world opened back up, we had raised over $10,000 for a variety of charities and progressive political causes.

In November of 2020, I got the call I had been waiting for (almost literally) my entire life: I was going to be on Jeopardy in the following year. After a brief, moderately successful run on Jeopardy, I decided that between my newfound 15-minutes of fame, and my almost 50 trivia games I had written, that maybe bringing these trivia games into the world might be a good way to make some extra money. In November of 2021, I booked my first in-person weekly trivia game at Ye Rustic Inn in the Los Feliz neighborhood of Los Angeles. Sundays at 9pm at the nastiest dive bar you’ve ever heard of. It was a dream come true.

Almost 6 years later, and Lucky Guess has grown in ways I genuinely could never have imagined. We’ve got more than 25 partnerships with bars, breweries, restaurants, and private clubs around Los Angeles. We’ve also expanded into the Las Vegas Valley, and (recently) all the way to Portland, Maine. I’ve got a fleet of freelance hosts who bring their own flare to every game, and I (humbly) believe that I have a product that rivals any and all of the larger, more established trivia companies in the country.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It most definitely has not been a smooth road! I’d say the biggest struggle was in May of 2023, when I was laid off from my full-time position at the non-profit where I had worked for almost 7 years. This was sort of a make-or-break moment for me: I could begin applying for other jobs, find another non-profit to work at, go back to teaching, etc. Or I could take my severance check and spend every last dollar of it trying to build up the business and grow it into something serious. At that time, I believe the company had 3 weekly games, so it was far from a sure thing.

Can you tell our readers more about what you do and what you think sets you apart from others?
Our trivia games are designed to be fun and accessible for the maximum number of participants. This ensures that people are staying for the entirety of our two-hour games, and that people are coming back week after week to play trivia with us.

One of the things that sets us apart is our format – rather than a linear scoring format (1 point per question, or something like that), we use a wagering system that I adopted from my last trivia company in Boston. Basically, you can assign higher point values to the answers you’re more sure of, which helps keep games closer. People are able to play more to their strengths.

We also utilize song clues for every question, which gives players a related but entirely different in-road to each question. For example, if I ask a question where the answer is “Canada,” I might play a song by a Canadian artist like Justin Bieber or Shania Twain. If the answer is SNL’s Maya Rudolph, I might play “Lovin’ You” by Minnie Ripperton, her mother. That sort of thing.

One of the ways we ensure accessibility across ages and skill-levels is something I’ve created called “Dynamic Difficulty” – each question has at least a half-dozen variations that the host can choose from to make a question more or less challenging. This could mean an extra detail (“what singer” vs. “what 25-year old singer”) or a song clue that’s a little bit more helpful. This way, the host can adapt to the crowd’s needs and make sure that the most people are having the best time.

Before we go, is there anything else you can share with us?
I just love trivia! I find that it’s an incredibly effective and fun way to bring people together. I’ve gotten to meet all sorts of incredible people, made some wonderful life-long friends, and found a career that I absolutely love. I just hope that my passion for trivia comes through my games and impacts the people playing on a weekly basis. Also I was born on National Trivia Day, which is pretty cool.

Pricing:

• $200/game (weekly)

Contact Info:

• Website: https://luckyguesstrivia.com
• Instagram: https://instagram.com/luckyguesstrivia