A year ago today, a day changed my life.
One of my closest friends, Bryan Wish, invited me to volunteer for a kick-off conference announcing a new Venture Capital fund he was working for, Kairos Society. At the time, I was living and working in Costa Rica, but I decided to buy the ticket, make the trip to New York City, and take a chance. It sounded cool.
I landed at Laguardia Airport and caught an Uber to the Rockefeller Estate in upstate New York, the venue for the VIP welcome dinner. The volunteer coordinator took off her horn-rimmed glasses and wiped her lenses as she told me I'd be an "airport greeter" this evening. She yawned and went back to work.
When I asked for more information, she simply handed me a face sheet of all the VIP attendees and told me to chat them up until there were enough people to fill up a 12-person Mercedes Benz luxury bus. This bus would shuttle them from the private air strip to the Rockefeller Estate.
I arrived at the Terrytown airstrip and met the CFO of Kairos, Alan. We became buds, and he recommended I familiarize myself with the face sheet, so I would know who I'm talking as the VIPs arrived. As I paged through who I'd be greeting, I was blown away.
One of Kairos' sponsors, Blade (think Uber for private plane/helicopter charters), would be shuttling four VIPs at a time from Manhattan. These attendees ranged from the president of Mexico, Dr. Oz, the creator of Siri, billionaire VCs, executive editors of major press outlets, and more. What had I signed up for?
These amazing people started showing up. I found myself casually chatting with the founders of Periscope and Casper, two former Kairos fellows. I taught a former board member for Facebook how to use the airport's fancy coffee maker. I told Dr. Oz where the restroom was. Since it would take about 20 minutes to have enough people to fill one of the buses, these fleeting interactions usually turned into deeper conversations.
Eventually, when they would ask what I did for a living, I would stop telling them I was a volunteer for the weekend, and I would just go straight into my elevator pitch for Brawl for a Cause, my heart and soul. As more and more of these people responded positively to the concept, I became more and more confident in my passion project. Since I was able to pitch it dozens of times in a row to the VIPs in a few hours, I honed the Brawl story, iterating it based off what struck my audience most, or what would lead to the best followup questions.
By the end of my "airport greeter" shift, I had about 20 cards and saw Brawl for a Cause with new eyes. If these people thought it was cool or saw potential, why didn't I? Why hadn't I made the leap to full-time? Why didn't I have the gusto or cojones to go all-in on my dream? Maybe it was time.
The last Blade helicopter landed, and it was time for Alan and I to catch a ride with the last group of VIPs back to the Rockefeller Estate for our next assignment. I found myself seated between Naveen Jain, billionaire entrepreneur, and Jacqueline Novogratz, founder and CEO of Acumen. Much to my surprise, I was caught in the middle of a philosophical debate over humanity's role in the world.
Naveen argued a self-first mentality. We are meant to take care of ourselves so that we are able to take care of others. We should accumulate wealth and power, then focus on helping the world in our way. Jacqueline disagreed based off her life experience of putting others first, which lead to doors being opened that she would have never chosen or pursued herself. In a moment of self-awareness, Jacqueline turned to me. They had been arguing over me for quite some time, and she apologized for my being caught in the middle, then she asked what I thought.
I stumbled through something about it being in the balance of my and other people needs being met and making decisions on a case-by-case basis. I didn't think there was only one way to do it that worked every time, and the guy with messy hair and beat up Ray Bans seated directly across from me nodded and smiled.
When we arrived at the estate, affectionately called the "Play House" because of the golf course, tennis courts, bowling alleys, pools and more, my new Ray Bans buddy and I struck up conversation. We talked about travel and hikes we had done; about how we've never felt so alive than when we've been pushing our limits close to death. He was cool.
We reached the front of the check-in line, and the volunteer handing out name-tags freaked out when he saw my line-mate. "I'm sorry Mr. Night-Skat (?), I know this is unprofessional, but could we get a picture together?"
They snapped a selfie and the supposed celebrity walked in. I had no idea who he was. The volunteer turned to me and said, "I can't believe I just met Casey Neistat..."
I asked who he was, and he told me to just Google him. Then, he asked me for my name.
"Matt"
"Matt, what?"
"Matt Thomas"
"Ok, what company?"
"Um, Brawl for a Cause..."
"Ok, here you go. Have a good night Mr. Thomas."
I put on the name tag and walked in without thinking twice about what had just happened. This star-struck volunteer assumed I was a VIP because I was next to Casey Neistat, made me a name tag, and drastically altered the course of the rest of my weekend.
I went up to the overworked volunteer coordinator and asked how else I could help. She said I was free until the dinner bell rings, then I should help VIPs find their seat. Then, she asked how I got my name-tag. After I told her, she said I really wasn't supposed to have one, but that it'd be our little secret with a wink.
First, I went into the bathroom and googled Casey Neistat. After I watch "Do What You Can't," I immediately found him, told him what I had just done and how much I like his video, and asked for a similar selfie.
Then, I went to the bowling alley. I went head to head with one of the co-founders of a Y-Combinator company, then hit the bar for a few drinks with many of the others I'd met at the airport. Then, the dinner bell rang.
I helped guests find their seats, then found a spot near the outskirts of the tent while John D. Rockefeller Jr. welcomed everyone to his family's estate. I turned to the middle-aged woman next to me and commented how amazing the night had been so far, and how excited I was for what was to come. She asked how I was connected to Kairos, and I told her about Brawl for a Cause, then asked her about her connection.
"Oh, I'm Alex's mom." I didn't know who Alex was, so I asked. As I asked, John D. Rockefeller Jr. was handing the mic off to the CEO of Kairos, a guy in his late 20's named Alex.
" Oh, you must be such a proud mom!" She was.
She asked where I was sitting, and I told her the truth. I didn't have a seat. I was just a volunteer who was happy to be here.
"Nonsense. We had four guests not show up. Follow me."
As her son addressed the crowd, she led me through the room and seated me next to a 6 foot 6 Chinese man and the CEO of Foursquare, Jeff Glueck. She took the name-tag of the no-show and left me with a smile. Alex wrapped up his speech, and it was time for dinner!
Four courses came and went as chatter at each table produced laughter, aha moment,s and exchanges of business cards. I talked to Jeff a lot, and when my pitch to the tall Chinese man went poorly (Jack Ma's representative at the event wasn't interested in charity boxing), then a lady named Jacki Zehner moved next to me.
Her story astounded me. The first female partner at Goldman Sachs, she left finance to direct Women Moving Millions, a funding organization for female-run non-profits. She had just picked up boxing as a hobby, and we were fast friends.
After more presentations and dinner, the tables were removed and bars were rolled in for a happy hour before the after-party back in Manhattan. I struck up conversation with two ladies who were friends from Colombia Journalism School. One was managing editor of Inc, and the other for Entrepreneur.
Linda Lacina also headed up the podcast for Entrepreneur Magazine, and she seemed particularly interested in Brawl for a Cause. She asked all the right questions, and when her editor-in-chief, Jason Feifer appeared, she succinctly pitched Brawl for a Cause to him. As an entrepreneur, there is perhaps nothing more satisfying than hearing someone else pitch your company and do it well.
Afterwards, they asked me whether I'd like to be on their podcast's new season, which was centered on finding the courage to innovate. A few weeks later, that episode came to fruition. As our first national press coverage, we had sign ups in 17 cities around the country by everyday people who wanted to fight for what they believe in. I began to believe in Brawl for a Cause more than ever.
After the bars had last call, guests filed into the Mercedes buses and drove back to Manhattan. Once reaching the hotel that the VIPs were staying in, I shared a cab with an entrepreneur named Nanxi Lui, CEO of Enplug. I had already heard her present earlier that evening and was blown away by her story. She asked me mine.
When we got out of the cab, we didn't even walk into the after-party. Right on the curbside, we had our first boxing lesson. She was in heels and a dress, but she still threw a mean right hook. As we practiced jabs and crosses, the after-party ended and we developed a small audience of spectators. A few others joined in the curbside boxing lesson, then very abruptly, Uber XLs took everyone back to the Kairos hotel blocks.
Since I wasn't staying with the VIPs (just posing as one), I bid everyone else farewell and found myself alone on a noisy New York City curbside. As a southern boy who had only been to NYC a few times, I felt lost, alone, and out of place. To myself, I said, "Welllll shit, where the hell am I?"
Behind me, I heard laughter. It might have been the sweetest sound I'd ever heard, even though she was laughing at me. "Not from here?"
Then, I turned and met her. It was midnight on the day that changed my life. Since our conversation technically took place on the next day, I'll leave that story for another time.
I'll sign off with this - Leave space in your life for serendipity. If stars align, follow their path. Questioning luck and hesitating with opportunity won't do you any favors. Even if you're an oblivious volunteer, be yourself and go with the flow. Then, like me, you may find yourself an accidental VIP.
Has a lucky day ever changed your life? What happened?
