TrivWorks Founder Confessions: Why Did I Start My Own Business?

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I typically use this blog to publish articles and resources which I think would be helpful to event planners, whether they are seeking to produce group bonding activities in New York City, corporate party entertainment, conference/meeting breaks, holiday party entertainment or any similar event. However, occasionally I like to delve into something more personal and revealing, to let folks know more about me.

Today, I’ve decided to tackle just such a topic, and it’s a big one: why did I decide to start my own business in the first place?

Somebody asked me this recently, and I have to tell you, it made me stop and think. I’m so used to answering a slightly different question: HOW did I start my own business, or why did I choose trivia team building as a specialty? But why did I open my own shop at all? That’s astonishingly a new one. I’m sure I had a ready answer seven years ago when I first hung out my shingle, but it’s long since faded; it’s time that I once again answer this question.

I guess a little perspective is in order. Seven years ago, in late 2009, I was working at the 92nd Street Y, a very prestigious cultural and community center located in Manhattan, on the Upper East Side. I had been working there for over three years, starting as a junior event programmer, and eventually becoming director of all adult education and enrichment programs. Being an event programmer was a job which naturally suited my skills: creativity, establishing partnerships, dreaming up fun and compelling activities for others to enjoy. I often compared myself during this phase of life to a camp director for grownups – or, perhaps more accurately, a cruise director on a ship. It was fun, it was challenging, it was good for me. I was honored and proud to work at such a place.

As with any job, however, there were also things which weren’t so great. We were deep in the global financial crisis at the time, and the ground beneath the organization – and the entire island of Manhattan, really – was unstable. Earlier in the year, I had managed to avoid a round of layoffs. While feeling fortunate, I was none the less assigned the entire workload of a former colleague, who had not been so lucky. Forget additional compensation – I was told in no uncertain terms that I should be grateful I didn’t exit the building with a box of my personal belongings. And I did feel grateful, because the alternative WAS unemployment. But from that point forward, my attitude changed.

Up until then, my responsibilities had included programming I was generally interested in and enjoyed planning/running: food and wine events, game classes, walking tours and “behind the scenes” outings all across the city, personal development and career growth events, singles mixers – I even dabbled with creating some of the high-profile lectures which 92Y is renowned for. With the New Order, however, I was given programming responsibilities which I was decidedly NOT interested in: namely, overseeing language classes and humanities lectures.

To back up even further, I have never been good at or interested in foreign languages. My brain just isn’t wired for it. I struggled through five years of French between junior high and high school, and vowed never to have to go through that again. When I arrived for college at Tufts University, however, I was greeted with the harsh reality that my new school had a SIX semester foreign language requirement. Sick of French, I tried Italian – with miserable results. I got my lowest grades of college in my Italian classes.

Fast forward a decade or so, and here I was, being told I had to now administer dozens of foreign language classes. I wasn’t passionate about it at all, had zero motivation, and viewed it as a chore. Between that and the humanities lectures, which I also wasn’t fond of, I suddenly had a huge chunk of my workload devoted to stuff I just didn’t enjoy, didn’t care about, and really wanted nothing to do with.

I was unfortunately also stagnated in my role. I had reached as high as I could go as a programmer; the next level was department head, and for a variety of reasons that wasn’t going to happen any time soon, if at all (honestly, I don’t know if I would have even wanted it). Lateral moves were also out of the question, as the institution was in a “hiring freeze,” and everyone who still had jobs wasn’t going anywhere. I thought about looking for a job elsewhere, but was that really the time to do it, during a major recession? Assuming I could even find a new job, I knew as well as anyone that should things continue to go South, the new hires are often the first to be let go. I was stuck.

Horrible economy. Languishing position. No options inside or outside the organization. What could I do?

I realized I had just one choice. I had to become my own boss.

At the time, I was also supplementing my income with two side gigs. For three years or so, I had been hosting bar trivia nights in Manhattan, which were incredibly popular and well-received. I had also been freelancing at City Hunt, a great corporate team building scavenger hunt company, where I served as a writer, producer and guide. When the economy crashed, I realized that there was an opportunity here to create a brand-new form of office team activities in New York City and beyond, using customized trivia as a format.

And so, I established a company – first David Jacobson D.B.A. TrivWorks, then eventually, as it got bigger, TrivWorks Inc. I devoted massive amounts of time and effort to my new venture, waking up early before work, staying up until the late hours after work, even devoting entire weekend days/nights to it. I was a man obsessed: I built a Website, established a social media presence, wrote and rewrote copy. I read constantly, anything I could get my hands on about starting and growing a business. I started blogging, pitched myself to trade media publications, grew my client list, and gradually began obtaining testimonials. I knew if I kept it up, I’d reach my ultimate goal.

It took me almost three more years, but I finally did it. Three years of working a job I no longer felt passionate about, but that I knew was necessary to grow something which I was. I managed to save about a half a year’s salary, then took the plunge: I left my position as program director, and took my trivia company full-time (click here for more on how I did that).

That was almost five years ago. Today, TrivWorks looks completely different – I’d even say it IS a totally different company. Whereas it used to be just me, churning out work at my home desktop computer and hosting gigs, I now have an entire team of professional corporate event emcees who host events across the country. I’ve been fortunate to establish partnerships with a wide (and growing) range of “special talent” hosts including celebrities, media personalities, comedians, a magician, a musical improvisation troupe and more, as well as provide karaoke, social good, experiential marketing and other offerings. I’ve partnered with The Bell House in Brooklyn to create the largest public trivia nights the Big Apple has ever seen. I’ve even relocated to Long Beach, CA to establish a presence for my company in Southern California and the West Coast.

Anyway – that’s my characteristically long-winded answer to the question, “why did I start my own company?” Now that you know the back story, the short answer is: I was in a tough spot, but saw an opportunity to be my own boss. So I took it.

And I’m so glad I did!

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