VC Jesse Middleton on why he cares about the state of Brooklyn tech - Brooklyn

Nov. 10, 2017 10:03 am

VC Jesse Middleton on why he cares about the state of Brooklyn tech

Flybridge Capital's Jesse Middleton says the distance the bridges cover is shorter than ever.
Jesse Middleton, VC at Flybridge Capital Partners, talks tech in Union Square.

Jesse Middleton, VC at Flybridge Capital Partners, talks tech in Union Square.

(Photo by Tyler Woods)

In the world of big data and artificial intelligence, venture capital investor Jesse Middleton values something a little different.

“One thing we look for is the ability to make fast decisions intelligently with incomplete data,” Middleton explained to Brooklyn.

In startupworld, particularly in the infancy of the seed funding stage, those decisions happen all the time, he said. “Up until the late stage of businesses, every decision will be made with limited or incomplete data. You’re making a decision that out of like 20 beta users, three really like this thing. Should I continue to build off that? It’s maybe not statistically significant but it’s super important.”

We caught up with Middleton last month to hear his thoughts on what he looks for as an investor and the state of the Brooklyn tech scene.

Now living in Harlem, Middleton lived in Brooklyn for much of his time in New York and has investments in several Brooklyn and Brooklyn-adjacent startups, including: Shine, Bulletin, Wethos and Thunderclap.

“I think the bridge spans less space than it used to,” he said during our interview, which took place partly walking around lower Manhattan and partly in Union Square Park. “I think there’s a brand to be built around Brooklyn but the vast majority [of startups] in Brooklyn choose to be as close to Manhattan as possible.”

That is starting to change, though.

While in the past, most startups were right over the bridge in Dumbo, more and more are setting up in non-riverfront neighborhoods like East Williamsburg, Gowanus and Red Hook. That was not happening when Middleton was building a Brooklyn startup eight years ago.

“The obvious change is that there are more tech startups based there now than there are then,” he said, of Brooklyn. “Probably like 10x. Back then it probably would be been a topic of conversation: How are you going to convince people to go there and work? But now workers live there a lot more. Williamsburg is good, Park Slope is good. There’s far more companies and there’s basically no stigma to being located there.”


Middleton’s tech career started early. When he was 16, he and a friend in suburban Philadelphia built a web hosting company called Get IT Connected. When they went to college, they sold the company for beer money. Middleton went to Drexel University in Philadelphia, an engineering-heavy college, where he studied management information systems. During a co-op semester (basically a four-month full-time paid internship) he fixed up their network security and they offered him a job. He dropped out of school and took it, living in Center City Philadelphia.

When he was 23, Middleton got married to his college girlfriend and they moved to Brooklyn’s Windsor Terrace neighborhood. He had a startup called ChefAMe. In going to the NY Tech Meetup (which was “much smaller” in those years) and being around the tech world, he met the founders of WeWork, who had just opened the first space, in SoHo. Many of the founders he knew at the time became their first members. ChefAMe folded eventually, but it opened him up to be one of WeWork’s first employees and the cofounder of its WeWork Labs, which he ran until last year.

Now a general partner at Flybridge Capital, which has invested in more than 100 startups and has upwards of $620 million under management, he explained the three most important traits he looks for in founders.

1. Being trustworthy

  • “We’re investing in a founder because we trust that they’re going to be good stewards of our capital and follow through on what they say they do.”

2. Emotional intelligence or “EQ”

  • “The founder’s ability to connect with other people the biggest reason they’re going to attract other people to their business.”

3. Good gut decisionmaking

“In human thought is there’s concept of Bayesian filters, where the mind runs through a shitload of scenarios every second and picks which one it should listen to. Fight or flight is a main one. It’s a split second decision with no idea what the outcome is gonna be.”


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