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Our New General Partner Jesse Middleton and How We Recruited Him

June 20, 2016

Welcome Jesse Middleton as our Newest General Partner.

I met Jesse Middleton nearly five years ago, shortly after he had joined up with the WeWork team to start WeWork Labs. A mutual friend thought we’d hit it off and they were right. We had similar backgrounds. We both grew up in small towns and studied computer science in colleges not far from home. We both started our careers in network security. And we both came from entrepreneurial families and wanted to start our own companies from a young age.

My first recollection of spending considerable time with Jesse was at SXSW, a year after we were introduced, spending the day on a houseboat on Lake Austin along with a group from the NYC startup community … sponsored by Macallan scotch. That day started around 10am and ended around 5am, crowned by karaoke and Austin’s finest late night chicken and waffles.

I learned two important things about Jesse that day. The second most important thing was how much he genuinely loved people – he was authentically friendly and warm. The first most important was how passionate he was about helping startups. WeWork Labs – the in-house incubator dedicated to building and nurturing a community – was an insanely fast growing initiative at WeWork servicing their startup customers. Jesse’s enthusiasm was infectious and I was blown away, if not a bit incredulous, by his vision on how WeWork would become a de facto home for technology innovation. He was more right that I could have imagined.

Jesse and I stayed in touch over the years and I have observed and cheered as he and the WeWork team have built a monster of innovation and global impact. His work at WeWork has been amplified by his personal angel investment activities – 15 exciting seed stage startups, as well as his insatiable commitment to the New York startup community.

I couldn’t be more pleased to welcome Jesse as our newest general partner in the New York office of Flybridge. We are excited to have him join us to help lead the next chapter of our firm. And we’re very happy to have Magda, Jesse and Holden as part of our family.

Our Search Process

Rewind to six months ago, January 2016. Our close friend and partner, Matt Witheiler, told us he was leaving to take an incredible opportunity to run Wellington’s billion dollar late stage venture fund. While we were sad to be losing Matt, we saw a great opportunity to add a new general partner to our New York office who would bring a different background to our team; hoping we would find someone who shared our values, but someone who could complement our thinking because of their own strategy, philosophy and experiences. Someone who would bring a different lens to look at Flybridge; to question and challenge and improve the way we work with startups and serve entrepreneurs.

This search became the most important task for Flybridge -This was the first time we have hired a General Partner since I joined eleven years ago. Our spec for the ideal candidate comprised the following:

  • is a great cultural fit
  • generates deal flow
  • has a great reputation in the NYC startup community and beyond
  • has been founder, CEO, or among first 10 employees of a successful or in-process successful startup
  • comes from the tech industry, media, journalism, investment banking – cast a wide net
  • is an active angel investor with a good portfolio and strong deal flow
  • is a magnet for great entrepreneurs
  • is a thought leader
  • wants to be a VC for the long haul (i.e., not dabbling)
  • has demonstrated intellectual curiosity and range of interests and sectors
  • has a strong social media following
  • has the potential to help lead the firm for the next 20+ years
  • is creative, strategic, aggressive and ambitious

This list was an aspirational one and Jesse Middleton was the precise prototype. I reached out to Jesse early in our process but wasn’t sure we’d be able to land him. Like any strategic executive recruiting mission, we cast a wide net. I was fond of saying “We want to move quickly to meet people, but take our time to get to know them.” The stakes were super high and we had to make sure we were being thorough and thoughtful. We screened hundreds of potential candidates and met with dozens of really incredible individuals.

We were completely blown away by the quality of the people we spoke with during the search. As we got more serious about candidates, we wanted to figure out a way to “game time simulate” them being part of our investment team. We decided the best way to do this would be to invite candidates to our Monday staff sessions and to meetings with startups pitching us.

Jesse vaulted to the top of our list. Jesse attended staff meetings in NYC and BOS, and it was as natural as if had been with us for years. We attended sessions with promising startups Jesse had been working with; and we invited him to sessions with startups we were evaluating. He checked us out with references we gave him and many we didn’t. We did the same, holding ourselves to the same high standards we encourage with our portfolio companies to pursue in their searches.

Important Thanks

In addition to incredible candidates, we spoke with a number of NYC startup “super connectors” to get their ideas and feedback. They gave us countless hours and made important contributions as we turned the spotlight inward. We can’t thank them enough. A special shout out to our advisors, Paul Blumenfeld and Bob Freier of Genero Search – who helped me cast the widest net we could.

I want to thank the amazing people I met during the search. It was an energizing experience to be marketing and selling Flybridge. I learned so much from the insightful questions asked by these brilliant people and several of these discussions have caused me to think differently about the future of Flybridge and the venture industry. More on that later.

We are more than excited to have Jesse on board. He has hit the ground running and I am wearing a constant smile as I think about working with him to continue building and improving Flybridge.


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