My venture into venture (capital)

Jesse Middleton
Jesse Middleton
Published in
3 min readJun 20, 2016

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In February I took a look at my journey into the angel investment world. I had been doing it for only a little over a year, but I learned a ton. I learned that I loved discovering and getting to know new founders. I learned that I enjoyed helping to solve some of the earliest challenges that those founders face. I learned that I had the ability to celebrate with the people I backed when they had huge wins and, more importantly, I learned I could be a shoulder to lean on when things (often) didn’t go as well. But my biggest takeaway was a personal reflection: that I wanted to focus on investing in and supporting these amazing founders full time.

These last five and half years helping build WeWork have been been a wild journey and I’ve loved every second of it. I got to experience the earliest days of startup life when we all came together at 3am to put the final touches on our first WeWork buildings. I also got to experience the meteoric growth and success as we barreled past 1000 employees and announced our 29th city. Thank you to everyone at WeWork for every single moment. But, as I announced in May, it was time for me to leave WeWork and become a full-time, professional investor.

Today I get to share the next big step of my adventure — I’m joining Flybridge Capital Partners as a General Partner. I will be leading our New York office alongside the one and only David Aronoff. I couldn’t be more excited to be a part of the Flybridge team!

David and I met five years ago at a Flybridge event. We became fast friends and I’ve been able to look to him for guidance and mentorship (and he’s always up for a drink) ever since. I met the Boston team a few years ago when I helped launch WeWork Boston and have loved our interactions as well. Flybridge has had a strong presence in New York for years. David opened the office here four years ago and the partners have invested in some amazing companies including 33Across, BetterCloud, Bowery, Codecademy, MongoDB, NS1, Raden, Shine and tracx. With my arrival, we plan to support our “family” of portfolio companies here even more while also doubling down on investing in the New York City startup ecosystem.

When I first sat down with the Flybridge team, we talked about what they were looking for in a new partner and where I wanted to take my journey next. Two things became abundantly clear very quickly:

  1. They were great investors, board members and champions of their portfolio companies and their founders.
  2. As good as they were at being great investors, they were even better people.

Every single person I talked to throughout the process echoed these two things. As I got to know them better, it quickly became clear that working alongside the whole Flybridge team just felt… right.

WeWork’s mantra is to “Do what you love” and that’s what I know I’m continuing to do now. I’m excited to dive in, to get to know the Flybridge Family (52 active companies and their thousands of employees) and to continue to support the New York community that I love.

If you’re working on something interesting, are looking for feedback on your new idea, thinking about raising your first round or simply want to shoot the shit about startups and NYC over a drink don’t hesitate to say hi. You can reach me at jesse@flybridge.com, on Twitter and on Facebook.

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