A Day in the Life of TrivWorks’ Founder & CEO

Trivia.hosting.corporate.events.NYC.jpgTrivia hosting corporate events NYC

Today is a special day for me. Exactly five years ago on this date, I left the security and stability of employment at a nonprofit organization, in order to take TrivWorks full-time.

It was both an exhilarating and terrifying time. Up until that point I had, for the previous six years, been Director of Adult Education Programs at the 92nd Street Y in Manhattan – a prestigious cultural & community center, which has gained new global prominence in recent years as the originators of “Giving Tuesday.” Also during that time, I had been hosting bar trivia nights on the side for over five years, and a couple of years prior, in 2009, I had established TrivWorks as a side business. I also had a wife who was just about to give birth to our first child.

So yeah, exhilarating – but scary!

Today, it’s almost like a completely different company altogether – so much has changed in the past five years! Our client list has grown exponentially, as has our number of media placements; our hosting roster has broadened to now include a bench of exceptionally skilled and experienced corporate event emcees (click here for more), as well as “Special Talent” emcees including comedian Christian Finnegan, magician Ryan Oakes, musical improvisation comedy troupe Broadway’s Next Hit Musical, and Double Dare’s Marc Summers; we offer trivia/karaoke and trivia/dance party experiences with DJ BayBFace; and NY1’s Pat Kiernan and I established the largest public trivia night series in NYC at The Bell House in Brooklyn.

Perhaps the biggest change, however, is that this past summer I relocated to Long Beach, California to establish a West Coast presence, enabling us to better service clients with corporate event entertainment in New York City, Southern California, and literally everywhere in between!

When I went home from 92Y the evening of December 15th, 2011, with a bag full of all my personal belongings and an uncertain future ahead, I was in a much different situation than I am now. Back then, this company truly was just me – I was doing literally everything: promoting, selling, bookkeeping, administration, writing all the trivia, producing every event, hosting just about every event (with the exception of the one other emcee I was working with, Pat Kiernan). Before long, I would add “taking care of newborn infant” to this list, which I did at home with my wife during her three-month maternity leave, then for another seven months on my own after she went back to work. Life was a grind, to say the least.

What’s my life look like today? I thought I’d paint you a brief picture, to help understand what it’s like being the CEO of a professional trivia event hosting company!

Most weekday mornings begin at or before 6am, when my wife’s alarm sounds. I say before, because we now have two children – and as anyone with kids under five knows, sleep is a privilege, not a right.

Assuming I’ve had a (somewhat) full-night’s sleep, I’ll roll over and grab my iPhone, where I’ll see that I’ve already got a half a dozen Emails that have come in just that morning: new business inquiries, Emails from clients, news alerts, the usual stuff. All of this serves to remind me that even though it’s the crack of dawn where I am, back on the East Coast where much of our business happens, the workday is already well underway – and I’m basically starting three hours late.

My wife and I will work together as a team to get the kids up, dressed, fed and then out of the house to their respective schools – I take one, she takes the other. Then it’s time to head to the office, where I fire up my desktop, have a quick breakfast and coffee, and dive right in headfirst to the business of the day.

I thrive on having multiple, diverse things happening at once – I was trained to deal with and in fact enjoy this type of environment, both from my years working at PR agencies juggling multiple clients, as well as my years at 92Y, where I was personally responsible for programming over 500 annual classes, lectures and events. In my current life, that means the first half of my day could be consumed by any number of things: responding to inquiries, drafting/sending event proposals and contracts, taking calls with clients or staff members, researching and writing trivia questions, prepping materials for my hosts, producers and grading staff who have events scheduled. I also keep abreast of what’s happening in my industry and the world at large, reading the news of the day as well as what’s being said about my brand online.

A big chunk of my day is also devoted to promotion. I like to dedicate at least a couple of hours a week to writing blog posts such as this one, but I also invest a significant portion of time to pitching reporters, as well as researching and reaching out to prospective clients and partners. If you’re reading this, than you’re probably also aware of our active Twitter feed, @TrivWorks, which I like to keep fresh with timely humor and trivia, as a means of extending our brand.

I’ll usually grab either a quick lunch by my desk or take a lunch meeting out in Long Beach somewhere (or, if I’m lucky, I get to have lunch with my wife), but then it’s right back to work – again, being three hours behind the East Coast means I have to finish any business there as soon as I can. When possible, I like to then use the later part of the day for “big picture”-type stuff: strategic planning, dreaming up new offerings and trivia corporate entertainment experiences, and basically trying to envision where I see things going. Before I know it, it’s already getting dark out, and time to pick up the kids. Any other work to be done will have to wait until later that evening, after bedtime, or early the next morning, when I start it all over again.

But of course, I’d be remiss if I didn’t illustrate what happens on days when I have gigs – I am, after all, not just a trivia event producer, but a corporate trivia host myself!

If I’m going to be personally attending an event, be it as a producer or as a host, Game Day brings with it an entirely different set of responsibilities – albeit in addition to, not in place of, everything I’ve mentioned above! If there’s a gig that night, I’ll be spending a good portion of the day being like Santa: making my list, and checking it twice. I’ll make sure my gear bag is packed with all of the materials we’ll need (score sheet packets, answer keys, branded pens and lip balm/other small prizes, my portable amp and microphones, iPod, Tablet computer, extension cord, and anything else that’s required). I’ll head over to the gig (which may involve a car, train or plane), where I swiftly put on either my production or hosting caps: for the next several hours, I am then completely and totally immersed in whatever is happening in the room, making sure the event is a success.

No matter what time of year or what’s on the schedule, it’s always a full day, and I’m never twiddling my thumbs. I truly love being my own boss – though it’s not without its stressful moments, and I assure you this type of entrepreneurial lifestyle is not for everyone. But I’m having a blast with it, love doing what I’m doing, and can’t wait to see what the next five years bring!

For another article on why I started my own trivia company in NYC in the first place, follow this link.


  1. Kabir on December 16, 2016 at 11:10 am

    Its quite amazing and inspirational, what you have done with TrivWorks, Dave. We love ya! Keep it up! Kabir and Nicole

    • david on December 16, 2016 at 11:58 am

      Thank you both!

  2. Mark young on December 16, 2016 at 3:50 pm


    Hello from a fellow former 92y colleague – so proud of you buddy – what an inspirational awesome story of following your professional and personal dreams and making them come true. I have a busy wife and two young kids and a busy job (still in the Jewish world) like you, but no where near the instensity you have and risks you’ve taken. Very impressed David and keep rockin’ it!

    Cheers, Mark S Young

    • david on December 16, 2016 at 3:54 pm

      Thank you Mark for the kind words! I greatly appreciate it – best of luck to you and your family as well!

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