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Jesse Middleton: “The best thing about Philadelphia is the closeness of the whole community”

This is Exit Interview, a weekly interview series with someone who has left Philadelphia, perhaps for another country or region or even just out of city limits and often taking talent, business and jobs with them. If you or someone you know left Philly for whatever reason, we want to hear from you. Contact us. […]


This is Exit Interview, a weekly interview series with someone who has left Philadelphia, perhaps for another country or region or even just out of city limits and often taking talent, business and jobs with them. If you or someone you know left Philly for whatever reason, we want to hear from you. Contact us.
Jesse Middleton tells his story like small town boy makes good.
He went a small high school — graduating class of about 70 people — an hour north of Philly and got his first taste of city life when he attended Drexel University and then stayed a half dozen years.
“I found an amazing co-op job, traveled a lot and went on to do network security consulting, technology writing, SaaS implementations for enterprise companies,” Middleton says, “and finally moved to New York City.”
It was strictly about a job, he says, traveling where the money was good at the time but still harboring all the intentions to come back to the place he first made his home.
Below we talk to him more about what pushed him to leave and why he is so sure he’ll come back.


When did you actually leave?
I left at the end of November of 2009. It’s been a little over a year.
What are the primary reasons you left for NYC?
Primarily, I had a job offer from a great [customer service] company, LivePerson, in New York City. I was taking a great role in a publicly traded technology company. That was pretty cool. In addition, I got the job offer the morning of my wedding. My wife and I figured that we were already changing our lives by getting married, why not explore a new city together too.
Was there a specific event or moment that you realized you had to/wanted to leave?
It all happened pretty quickly. From job offer to moving was only a few weeks. We got married, found someone to rent our apartment, found an apartment in Brooklyn and hired movers to get everything up there. It was a pretty crazy November.
Was there anything that could have been done differently to keep you?
No, this was something that was bound to happen. I’ve traveled to many cities around the world — Hong Kong, Shenzhen, London, Warsaw and Chihuahua to name a few — and I always knew that I’d like to try living in some other cities. New York is just the first of many for me.
Do you think you would return to Philadelphia under appropriate circumstances?
It’s not a matter of if but a matter of when. I plan on moving back some day.
When someone you meet in NYC asks about Philadelphia and its startup community, what do you tell them?
Philadelphia is an amazing community for tech and startups. There are fantastic developers, brilliant designers and the food is amazing — this is important to most tech people. The best thing about Philadelphia is the closeness of the whole community. In New York, every event has a different group of people. This is great for certain things, but I do miss the fact that whenever I went out to an event or my local bar in Philadelphia, I’d find the same groups hanging out — my friends.
What is the perception you most often find of Philadelphia?
Philadelphia is too small and it doesn’t have the money or infrastructure to support startups. This is totally untrue.
What’s the latest you’re up to that we can plug or look forward toward?
I’m building a new company in the healthcare technology space called GetMinders. We connect people with their medical reminders, their medical professionals and their families and support networks all via a quick phone call or text message. We’re currently in a really early alpha but you’re welcome to share the invite code — for up to 30 people: ‘IMISSPHILLY’ with your readers. They can try it out here.

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