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How Getting Rid of My Fear of Meeting People Helped Me Meet Daymond John
Daymond John

How Getting Rid of My Fear of Meeting People Helped Me Meet Daymond John

I had never really gone to a networking event before, but it had been a year since I graduated college, and I couldn’t bear to work at the company I was at for much longer. I had to do something. “I guess I better learn how to meet people,” I thought to myself.

My first networking event


It was a new tech event called Dart Boston, held at a bar in the city, so I figured at the very least I’d have a few drinks and if I was lucky someone would talk to me. But little did I know that the gentleman who organized the event, an alumnus of my university who was just a year my senior, did not leave these things to chance.

The minute I walked into the bar I scanned the scene of people talking to each other, dreading the thought of standing in a bar alone, when I noticed the guy who I would later come to know as Cort Johnson, founder of Dart, immediately catch my eye and approach me with a smile.

“Hi there, are you here for the Dart Boston event?” asked Cort, introducing himself. “Yes, I’m Sergei, thanks for having me.”

“What brings you here?”

I explained to Cort that the event looked cool and I wanted to meet other people interested in startups. Within about 30 seconds of talking to me, he walked me over to another attendee that he seemed to know well, and introduced us saying that we should chat.

That was it. Sounds simple doesn’t it? But I was blown away, so much so that I’m even talking about it now, 10 years later. It wasn’t anything in particular that Cort said to make me feel comfortable, it was his effortless ability to connect like-minded people that impressed me most.

All he did was come up to me and physically bring me to another person who at that moment was experiencing a lull in conversation, and not only did that make me feel special because he was paying attention to me, but with that small action he ensured that I would have a good time and would be much more likely to come back.

That moment stuck with me, and would come back to me every time I would go to an event and would feel myself going back to my old habit of trying to sip on my drink while avoiding awkward eye contact.

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Instead, I would force myself to walk over to someone and simply say hi if I had nothing better to say, and ask why they were there. It turned out that changing that one simple habit would open up a world of relationships to me that would otherwise never have a chance to happen.

Using that first lesson to build valuable relationshipsNetworking for introverts:

Cort’s friendly disposition kept me coming back to his events, and as I got more comfortable meeting new people, I expanded my network, and developed my relationship with him as the organizer. Months later, when I was working on starting a new venture with my brother, Cort was testing out a new event format where he would interview founders in a live, recorded event, in front of hundreds of attendees.

All I had to do then was ask, and he agreed to interview me and my co-founder right as the event was gaining momentum in Boston. This interview resulted in great exposure to the community for our nascent venture, and would have never happened had I not continued to show up to his networking events.

A year later, I was attending another Dart Boston event when I saw a young man I had never met before standing sheepishly near the bar. I came up to him and made some silly joke about one of the event speakers to try to make him feel comfortable.

Without hesitation, the guy matched my sarcastic tone, and we were instant friends. It turned out that he was a student at Northeastern University who had just gotten into TechStars, one of the most competitive accelerator programs at the time, with his business idea.

Praful and I would become way more than just two guys who liked talking about building companies. Over the course of the next few years we became close friends who spent a lot of our free time together, and we still stay in close contact, helping each other through business and personal challenges alike. He is now building his next company in Silicon Valley.

How I met Daymond John and worked up the courage to talk to him


Eight years later, I had moved to NYC and was working at a national non-profit running their entrepreneurship programs. It was our annual summer fundraising event where Daymond John, founder of FUBU, known for his role as a shark on the show Shark Tank, was speaking as a guest.

There were hundreds of attendees and, not surprisingly, everyone was trying to get Daymond’s attention, or at least ask for a selfie. I didn’t really want to bother the guy and figured that I probably wouldn’t get a chance to speak with him.

But about an hour later I saw him standing not far from the bar chatting with some of the young entrepreneurs in attendance, who were peppering him with questions. I was only about five feet away talking to someone else when I had a flashback of my experience meeting Cort at that first Dart Boston event years earlier.

By that time, I had developed a pretty thick skin when it came to meeting new people. I had founded my own business, given lectures, and as a result had to meet new people almost every day. Yet, I was still resisting my own internal desire to go talk to a man who I really looked up to because of some small lingering fear of rejection that evolution had coded into my DNA.

That’s when I decided to try and think of something to say to Daymond to start a conversation, and bit the bullet and approached him. When I noticed that he finished answering someone’s question and there was a split second pause in conversation, I approached and simply mentioned something about the young entrepreneur he had just finished talking to.

I didn’t rack my brain for the perfect thing to say, but just thought of a phrase that would act as a natural transition to the conversation I wanted to have with him. We ended up talking about the accelerator program I ran for the non-profit, and the awesome companies we were spinning out, and it gave me an opportunity to start a relationship with this inspiring entrepreneur and TV personality.

Why you should talk to as many people as possible

For many of us, the internal dialogue that prevents us from approaching new people in any situation never truly goes away. But the more you practice getting out of your own way and simply saying something, anything, to the people around you, the more lasting relationships you will build.

Nowadays, when I have students or aspiring entrepreneurs approach me after a panel or a talk, I always try and talk to as many people as possible because I know how hard it is to take the chance and start a conversation with someone new.

But there’s another reason why I stick around, and why I’m sure Daymond stuck around to talk to people after his speech; you never know how the person standing next to you could change your life, or how you could change theirs.

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