Professional trivia host New York City

Something remarkable happened to me a few weeks ago. I was driving with my wife and kids to see family out of town, and my phone rang. It was my best friend from high school – one whom I had lost touch with about fifteen years ago, didn’t have a Facebook account, and I haven’t seen or spoken to since my early 20s.

We set up a time to chat later that evening, and got fully caught up. He is now a police officer in the city we grew up in, is married with two kids like me, and was just tooling around on the Internet and happened upon the TrivWorks Website – and saw my face staring back at him! So he called, and I’m so glad he did – we had a great chat, and I look forward to meeting up with him soon.

Of all we discussed during that hour-long telephone conversation, one thing he said to me in particular stood out. He said, “Dude – you started your own fun cool company, just like you always said you wanted to!”

Why was this striking? Here’s a guy who knew me well – VERY well – in my teens and early 20s. We lost touch after I moved to the city for graduate school, and as a result he hasn’t seen me at all since then – hasn’t seen me change, grow, mature. His views and memories of me are basically frozen in ember from another era, when I was essentially another person whom I myself wouldn’t even recognize today.

Yet he comes out and says this, and I was like, “Wow…is that REALLY what I said I wanted to do back then?”

I honestly don’t remember ever talking about creating a fun, cool company, or even having a “cool job” – what I DO remember, however, was that my first job out of college was an unmitigated disaster. I entered the workforce with zero direction – I mean, ZERO. No clue what I wanted to do, where I wanted to be, what passions I wished to pursue or dreams to chase. I did know, however, that I had to find a full-time job, and quickly, both to support myself as well as start building up a resume of professional experience.

Luckily I found work at a pharmaceutical company, which had its corporate headquarters just a few towns away –and I hated it. HATED it. I probably would have thrived at an Internet startup company, other “cool” place with a hip, young culture – but no, that’s not how things worked out. After four years of college and a few months off, I suddenly found myself as an entry level office drone making $30K a year, in a cubicle, wearing a tie, entering data and manipulating Excel spreadsheets all day. The environment was rigid, my fellow employees humorless and anti-social; there were never any happy hours, and we rarely hung out after work.

Now, anybody who knows me – both then and now – knows that I am a creative person, not an analytical one. This was basically the worst type of job I could have possibly taken for my personality and skill set, and I was miserable. I complained bitterly to friends and family about how much I hated getting up for work every day, how I longed for the weekends, how I was just putting in my time until my 1-year anniversary so that I could quit, and have at least a measure of stability on my resume for my next employer to see – though I had no idea at all what that next job would be.

I was basically Dilbert.

So being in that state of mind, while I don’t recall actually stating it, I can definitely see myself pining for a “cool job” at a “cool company,” perhaps even starting one myself someday. It’s ironic that that’s actually what I eventually did, even though that in and of itself wasn’t the impetus for me founding TrivWorks.

Today, I think most people would agree that I have a “cool job.” There’s plenty of grunt work involved, no doubt – however, the actual meat and potatoes of being a trivia host NYC, employee team building and corporate entertainment activities in New York and nationally, is undoubtedly fun and awesome. My job is to make people happy – people I’ve never met, whom I don’t work with, but whom I can create an extremely fun and positive shared experience for none the less.

It’s not uncommon when I’m emceeing an event to have people come up to me and say, “You have a REALLY fun job.” I’m truly grateful for that, but also kind of in awe as well. Because when people say that, all I can think about is this 22-year-old kid, sitting angry and depressed in a cubicle wearing a tie and punching in data, and how I had the polar opposite of a fun job. Now, not only do I get to enjoy a “happy hour”-type experience every time I go to work, but I get to bring the excitement and amusement as well – and that kind of blows my mind!

When I launched this company as a side business in 2009, I never actually thought I’d take it full-time; to me, it was simply a means of supplementing my income by doing something I enjoyed, which I also just happened to be good at. When it became my sole form of income in 2011, I of course took it seriously, as I still do – it’s still called “work,” after all, and as fun as my job can be, at the end of the day I’d still rather be spending time with my wife and kids than “at the office.” But hearing from my high school friend out of the blue like that, who reminded me that it was in fact always my desire to do something “cool,” has made me wonder: just how much of me creating this company was a natural progression of an interest in trivia event hosting, versus perhaps a much stronger, long-underlying desire to have a “cool job?”

Who knows – but I’m definitely much happier than when I was Dilbert either way!