Known for its bullish view on Boston’s tech scene, Flybridge’s portfolio includes 21 Boston-area startups out of 52 total, and just 9 in New York.
The firm, which has done mostly enterprise-tech deals, even runs a “scholarship” program called Stay In MA to help university students in and around Boston get into local tech and entrepreneurship events at low or no personal cost. The idea is that helping students network will prevent brain drain from Boston when they graduate.
Middleton said he joined the fund, in part, to help Flybridge bring the same kind of energy, and find more great founders to back in New York. At least one of Flybridge’s best-known portfolio companies today is MongoDB, a New York City startup, he noted.
Prior to joining the firm, Middleton spent more than a year doing deals as an individual angel investor. And he helped build WeWork’s membership and empire of co-working spaces from just a local business in New York to the international phenomenon it is today.
His personal investments have been in consumer companies like ClassPass and Eight, as well as services for small businesses, like InDinero and Morsel.
Middleton said he believes that New York is having a tech and startups moment, which is one reason he wanted to become a full-time investor there.
“We have always had an edge in media in New York. That’s continued in businesses like Buzzfeed and Medium. But what’s new here is the number of seasoned entrepreneurs mentoring or ready to invest in other startups,” he said.
Middleton pointed to the growth of WeWork and Flybridge-backed MongoDB, as well as Etsy, Buddy Media, StackExchange, Droga5 and other Big Apple businesses.
He intends to continue to back sharing economy startups at Flybridge, but that doesn’t mean Airbnb or UberX for everything, he cautioned.
Middleton explained, “There are challenges when you have more people freelancing or starting their own businesses…and fewer people going after those Fortune 500 jobs. That could be around data, insurance or logistics. And it’s not a hard and fast rule, but I’m mostly interested in backing startups that can leverage marketplaces, or that can be valuable to them.”
The investor is also interested in seeing startups bring virtual reality and augmented reality to work. Experts coming out of major media companies in New York should have great ideas about what to do with these emerging media types, he said.
To-date, Flybridge has mostly backed companies that had ten or more employees, and signed $1 million checks at a minimum. When appropriate, Middleton said he wants to bring some even earlier-stage deals to the fund, backing teams of 4 and signing checks closer to $500,000 in some cases.
Middleton will be the firm’s fourth general partner, joining alongside: David Aronoff, Jeff Busgang and Chip Hazard. As TechCrunch recently reported, a majority of top-tier venture firms have yet to hire women as full-time investing partners.
Correction: A previous version of this article stated that Middleton would be Flybridge’s fifth general partner. He will be its fourth.