A Foot in the Door 🚪👞

A spontaneous trip to meet Greg Isenberg for the first time, and to my surprise, Jack Dorsey as well.

Let’s start with the backstory.

Still fresh off the high of being in New York, I wanted to follow up my last article about Islands with a story you will never believe.

If you’re lazy and didn’t click the link to my article about Greg’s company Islands, here’s the short version. Greg tweeted that if you’re looking to join a team, then writing about the company and the space is the best way to get your foot in the door. Taking his advice, I decided to write about his company and the outcome was a night I will never forget.

After patiently waiting for Greg to come across my article, he found it once he hopped back on Twitter. We scheduled a call, hit it off, and he told me he would be in NYC on Sunday night if I wanted to meet.

Keep in mind, I’m still 19 years old. Naturally, the first thing I did was call my parents to tell them about what was going on. We spoke about the opportunity, and my father told me he was willing to drive me up to NYC from Philly (a four hour round trip) to see Greg and hear about a possible opportunity. Even though I was shocked that my Dad was actually into it the first time I was telling him, I wasn’t about to ask questions and we began to plan.

Greg and I scheduled to meet at the Mercer Hotel in SoHo on Sunday night, and that’s what we did. In the pouring rain, my Dad and I were en route to the Big 🍎. Waiting for Greg to get settled, I sat with my Dad at a bar close by and talked to him about the opportunity at hand, the feeling of optimism you have when you’re in NYC, and why in the hell he was even doing this to begin with. My Dad went on to explain to me that he just had a good feeling about the night and felt like it was the right time for me to take things with tech more seriously.

Now allow me to paint the scene.

Once Greg was set to go, I head down to the lobby/restaurant of the Mercer. I sat down on a chair waiting for him to arrive to this dim-lit room of the most beautiful people I’ve ever seen (almost all of them dressed in black). Once he did, we made the usual introductions and touched on some of the things we had spoken about over the phone the other day. In the middle of our conversation, Greg interrupts me to tell me that he thinks Jack Dorsey is in the corner of the room. I whip my head around to see if it’s him. I realize it is, and tell Greg bluntly that I was resisting the urge to cry. 😂

As you can probably infer, I’m really not one to keep things cool. My heart is worn on my sleeve at all times. In my defense, this really is every kids dream that’s trying to make it in tech. I don’t think I could’ve dreamt to have been in the same room as the CEO & Founder of Twitter and Square, let alone meet up with Greg!

Luckily, Greg was there to calm me down and laugh off how crazy this picture perfect moment was. As we laughed, we walked by Jack (and his friend, David) to head into the restaurant connected to the lobby. While we kept saying that it all felt like a movie, I wasn’t about to let the curtain close. I took the lead, swallowed hard, felt my hands getting warmer… walked around the door we came through and made direct eye contact with Jack.

“Excuse me, Jack?”

Thanks again, Jack Dorsey. 👊

What do you do in a moment like this?

I don’t think there’s any right way to bother someone who is famous, but we tried to keep it minimal and let Jack enjoy his night.

Greg and I introduced ourselves and I was able to tell him that I was a Philly student trying to make it in tech and that he was a huge inspiration to me. If at this point you don’t believe what you’re reading, he was even kind enough to let me take a photo with him! Without a picture, I don’t think that I would believe it either.

To be able to talk to someone you’ve stayed in on Saturday nights watching is a very surreal feeling.

We went on to ask his waitress what he was drinking and bought him a glass of wine with a note thanking him for meeting us that read… well, I’ll let you read it for yourself.

Still excited, we managed to calm ourselves down only to sit down at our table and…

After a brief moment of fanboying, we had our eyes back on the ball of the original conversation; building something that we might have the chance to show Jack later on. Islands. In order to reinvent an everyday process, you need to have the team to do it. After chatting further, Greg agreed to let me help strategize the growth of this amazing product. I couldn’t be more excited to help out on what I truly believe is the future of group communication.

So, what’s the real value of a foot in the door?

These are the moments that the internet was made for. To re-quote Greg, “The internet was supposed to be this place where anyone could be heard and anyone could instantly connect with people you wanted to know, not just the people you went to high school with.”

Part of the internet’s purpose is to enhance or serve as the interaction with people that you’ve never met or never heard, and lead you on the path to make memories and churn your emotions in a positive way.

While we do have to keep things cryptic, Islands is coming soon and we can’t wait for you to see what all of the hype is about. I hope it’s something that will enable you to have nights like these. Nights where you meet someone that you’ve been dying to meet or that fate needed you to. Nights that you’re able to hit it off with people you never thought you would. Nights that enable you to find your islands. 🌴

Go follow @findyourislands and check out islands.im

Thank you Greg for this opportunity. Thank you Mom, Dad, Abby and all of the people that support me and give me the confidence to experience these moments. Here’s to plenty more! 🍻

Stay tuned for what’s next! 😉

I hope this provided value to you or maybe inspired you to write about a company that you’re interested in! Throw me a ❤️️, would ya?

Find me at jamesxbase.com or (almost) anywhere @jamesxbase! I’d love to hear about you and the islands you might drift off to.