Case Study: Joining the Team You Want to Be On

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It’s August, which means I’m marking a number of unique milestones. For starters, it’s been exactly ten years since I hosted my very first trivia event – a pub quiz in Manhattan (read the story here). However, even before I became a professional trivia host in New York City, I was in the events and entertainment world. I spent six years as director of adult learning programs at 92Y, a major cultural & community center on the Upper East Side, where I grew the area to more than 500 annual offerings. I also spent two years freelancing at City Hunt, one of the premier scavenger hunt companies, where I learned the art of producing NYC corporate team building activities.

But before ALL of that, in August of 2000, I got my very first events job.

Exactly sixteen years ago, I was out of college and had just completed my first year in the “real world.” I wish I could say it was going well, but really it wasn’t. Being a completely unfocused young lad back then, I had taken my college degree and promptly gone back home to Stamford, CT, where after a few months of mindless temping I landed a full-time job at a pharmaceutical company. I realize in hindsight it was actually a good place to work, with good benefits, perks and opportunities for growth. But my job duties were awful; I was basically a data entry drone. And I had to wear a tie.

One morning in August, after a year of misery and not knowing what to do, I woke up and turned on the TV – to find that then-Democratic presidential nominee Al Gore had selected Senator Joe Lieberman to be his running mate.

Now, I want to emphasize that at that time I had literally zero interest in politics, or the election – I honestly wasn’t even paying attention, and didn’t feel passionately about either candidate or either party. I had voted in only a couple of elections by then, but had pulled the lever for candidates on both sides of the aisle. It had never excited me – until that very moment.

I instantly felt a strong connection to Lieberman. I didn’t know a thing about him or his positions (or even about Gore’s, frankly), but I did know he was a Jewish guy from Stamford, Connecticut – just like me. Like most other people back then, I was shocked Gore had picked him, an Orthodox Jew, to be his running mate. We’ve since seen other major political glass ceilings broken in this country over the last sixteen years, including an African-American President, two Attorneys General and two Secretaries of State, many openly gay elected officials, and the recent nomination of the country’s first female presidential candidate by a major party. But it was the Lieberman pick which resonated deeply with me, not because of my political ideology, but purely due to the closeness in both faith and geography. I’d have felt just as excited had the Republican nominee picked him – it truly wasn’t about politics; it was just the feeling of “this guy’s like me.”

I soon found out that both Gore and Lieberman were coming to Stamford the next day, for a “homecoming” rally to celebrate the new ticket. I knew I had to be there – again, not for political reasons, but purely personal ones. To me this was historic, and something I just had to be a part of; after a year languishing in an emotional purgatory, I was suddenly jolted into excitement, and had a mission: get to that rally!

The event was being held the following evening at the Italian Center, an event space long accustomed to political events, but which only holds a few hundred people. It was a ticketed event, and shockingly, all of the tickets had been grabbed up moments after being announced. Undeterred, I did something completely out of character for me.

I just showed up.

Heading straight to the venue after work, I encountered the expected madness: a frenzy of media trucks, security, and people waiting out in the sweltering hot August sun to go inside. Not really sure what to do, I glanced around, and then saw him: a guy in the parking lot, struggling to lift this enormous “Gore/Lieberman 2000” sign. It had been professionally produced, and this guy was clearly part of the event. Without even thinking, I went right up to him. “Here, let me help you with that,” I said, lifting the other end. He was incredibly grateful, and directed me towards the entrance.

We carried the sign through front doors, through the metal detectors, and were then waved into the main event space. It happened so quickly, I didn’t even have a chance to process it. The guy I had helped out thanked me, then disappeared – leaving me alone. The space was a hive of activity – I’d never been inside a venue setting up for a major event before, but there were important-looking people with serious faces scurrying around left and right. The event wasn’t scheduled to start for a couple of hours, and I knew that if I didn’t act quickly, somebody would catch wind of the fact that this random guy was milling about, and I’d be ejected.

And so…I put myself to work.

I rolled up my sleeves, went right over to the cluster of most-important looking people, and said, “Hi, I’m David – how can I help?” And for the next two hours, I helped. I set up chairs, hung banners and signage, and basically did whatever was asked of me. I kept in perpetual motion, certain that at any moment somebody would realize I didn’t actually have any business being there – but no one did. The fact is, this event had been put together extremely quickly, and they needed help – and I was there to help!

They finally let the press in, then the huge crowd. I’d never been to a political event in my life, and even if you’re completely unattuned to the political scene as I was at the time, it’s still electrifying. After several introductory speakers, out came Al Gore, Joe Lieberman and their wives, as Van Halen’s “Right Now” blared through the speakers. It was so surreal to me to have just seen these people on TV, and now here they were, right in front of me!

Both candidates spoke, the crowd went wild, and then they departed. I was walking on air, elated that I could be a part of history in a way, and could say I was there. But as I was filing out of the venue into the humid night with the rest of the crowd, I felt a hand on my shoulder.

Oh CRAP, I thought. BUSTED.

But you know who it was? It was that guy from earlier in the afternoon, the one who I had helped carry a sign in. He was smiling at me.

“David,” he said, “You were REALLY a big help today. Have you meet the Vice President yet?”

Kind of stunned, I sort of just stood there stammering – I think I eventually just shook my head.

“Come on,” he said, leading me back inside. We went through the kitchen, out the back door away from the crowds, to a small fenced-in area right next to the parked motorcade vehicles, where a few other beaming volunteers stood. “Just wait here,” he said.

So, I waited.

About ten minutes later, out comes Al Gore and Joe Lieberman. They both walk right over to us, shake our hands and say, “Thank you for helping out!” Then they pile into a waiting limo, and the motorcade takes off.

I turned to that guy who had brought me there, and asked him, bug-eyed, what exactly HIS role was. He told me he worked on the campaign’s advance team – something I’d never heard of before. Seizing the moment without even thinking, I said, “Umm…can I join that team?”

He smiled again, handed me his business card, and asked me to give him a call – which a day later, I did.

Not longer after, I gave my job two weeks’ notice, packed my bags, and soon found myself flying all over the country to help out at campaign events. I had zero experience in events, zero background in politics, and was understandably a bit different from the passionate idealists who I was working alongside. But I was having a blast, doing something exciting, and learning so much every single day about how to produce events at a professional level. It was really an invaluable experience, and while it didn’t last long (or well, as you are probably aware), it helped point me in the direction I would eventually go.

Today, I am a full-time event professional. And it all started sixteen years ago this month, when I sneaked into a campaign rally!

For more on what I’m doing now, visit

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