What I’ve Learned in 4 Years as a Full-Time Trivia Event Producer

trivia.host.for.corporate.entertainment.events.nyc.jpgTrivia host for corporate entertainment events NYC

Four years ago today, I made the biggest and scariest move of my life: I left the security and stability of gainful employment at the 92nd Street Y – an esteemed cultural and community center on Manhattan’s Upper East Side, where I had served as Director of Adult Programs for six years – to go out on my own as a NYC trivia host for corporate events.

I had started TrivWorks two years prior as a side business, in direct response to the economic crisis of 2008-2009; my intention was simply to supplement my income, as I had been doing since 2006 as a New York City bar trivia host – though I had it in the back of my mind that I could POSSIBLY make the leap, I never really thought I’d do this for a LIVING.

But alas, here we are four years later, and this is still my job, my sole source of income. I don’t think there is anybody else out there with the same unique experience as me: supporting myself by producing and hosting corporate trivia contests and employee team building activities. And yet, here I am.

As I look back on that day four years ago, with a wife about to give birth and when I knew money would no longer “magically” appear in my bank account every two weeks, I think about how much has changed in how I view my business, my industry, and the role I ACTUALLY play in my chosen field. Here are some of the key learnings I’ve picked up along the way, which may have run differently from (or even counter to) what I had assumed life would be like when I first hung out my shingle:

  • This is a Year-Round Job – Like many industries, this one’s got some busy seasons: holiday parties in December are quite popular, since trivia can be fun, festive and engaging; there’s also a spike during the summer, as we create exciting and memorable events for summer associates/interns of prestigious law firms and financial service companies seeking to recruit top talent. But there’s truly no telling when gigs will pop up – we could get a request for a group bonding activity the first week of January, or a mid-April “blow off steam event” for busy accountants. Gigs book months out, or the day before – you truly never know when that phone will ring, and this was an interesting thing to discover.
  • Have Trivia, Will Travel – As mentioned above, I originally intended my business to serve NYC-based companies who had been affected by the Great Recession. What I’ve found, however, is that there is a wide appeal for what I do not just here in the Big Apple, but in many other places as well. Since 2011, I’ve had the pleasant surprise of being whisked away by clients to Chicago, Orlando, Boston, Washington, D.C., Baltimore, Central and Southern New Jersey, Philadelphia, Connecticut and countless other places to produce events – as well as received requests for such far-flung places as Eastern Europe, South America and India. I was hesitant at first to book travel gigs, as I wanted to ensure that I could replicate the same experience as I do here in my “home turf.” What I’ve discovered, though, is that the same “turnkey” approach I use to make events simple and painless to produce in Manhattan can be easily reproduced elsewhere – my tech and logistical requirements are quite limited, and so long as I have some helping hands to assist with grading and administration, I’m golden.
  • Employees Aren’t The Only Audience – As mentioned, I created my business as a means for companies to say “thank you” to hard-working employees. However, since going full-time I’ve become aware of two other distinct audiences whom my services are sought out for: loyal clients, and dedicated brand enthusiasts. It was a surprise to me, however I’d say about half of the calls I get are actually for client entertainment ideas, as opposed to staff bonding events; I’ve also had a steady churn of requests for brands who want to go “offline” with a fully-immersive experiential marketing event, using trivia as the activity.
  • Diversity of Offerings is Key – In 2011, I essentially had one offering: a fully-customized competition, hosted either by yours truly or NY1 morning news anchor Pat Kiernan (whom I have since gone on to produce a successful public event series with at The Bell House in Brooklyn). But even though what I had to give was compelling, I found that both repeat and new clients were in fact looking for some variety. As such, I’ve since expanded my services to include “Special Hosts” in addition to Pat, including comedian Christian Finnegan, magician Ryan Oakes and former Double Dare host Marc Summers; I’ve also formed a collaboration with Spice & Spoon to offer a new in-office trivia/mixology experience, and recently rolled out a trivia/karaoke experience as well.

It’s truly amazing to me when I think back to who and where I was on this day in 2011, and how much different my life is now. I basically saved a half a year’s salary, and jumped into the unknown abyss of full-on entrepreneurship AND parenthood – since then, my wife and I have had two children, lived in three different apartments, and managed to make it all work somehow. I’ve had the pleasure of collaborating with so many wonderful people and institutions, and along the way firmly established The Bell House as New York’s premier venue for large-scale live trivia nights for the public.

It’s certainly been a learning process, and at times I’ve had to roll with the punches and find my bearings. But what is absolutely clear to me now is that A) I made the right choice to “go for it” and start my own business; B) despite the ups and downs inherent in any business, I’ve managed to plot my own course into what is COMPLETELY uncharted territory, in order to achieve success; and C) life can be unpredictable, but if you keep at it and don’t lose your focus, you can persevere.

Where will the next year, two years, four years take me and TrivWorks? Only time will tell – but I wouldn’t trade these past four years of unique self-employment for anything in the world. Thank you all who have been a part of this – bring on 2016!


  1. Brent Osborne on December 16, 2015 at 10:18 pm

    Nice read, David! We are looking forward to a great event at JCC Rockland. Congrats on this milestone!

    • david on December 17, 2015 at 9:42 am

      Thanks Brent! Looking forward to helping JCC Rockland’s staff enjoy a great holiday trivia party!

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