Jesse Middleton

Jesse spotted the remote work revolution over a decade before COVID. He has turned his prescient market insights into extraordinary returns for founders and investors alike. As an early WeWork executive who helped scale the company to 4,000 employees across multiple continents, and later as an angel investor with a 16x portfolio MOIC, Jesse has consistently backed transformative companies reshaping how we work, collaborate, and build community. His venture career spans both notable successes and instructive misses, fueling his deep commitment to supporting early-stage founders who are creating platforms that enable the future of work.

In the last few years, Jesse's focus has turned to investing in Full-Stack AI Native Applications —These products are often manifested as an end-user product for consumers, prosumers, and SMBs, and were impossible to build just a few years ago. These platforms will power the next generation of 10x humans, just as we saw when the shift to cloud-based development platforms created 10x engineers.

Over the past decade, Jesse has invested in over 50 companies, both as an angel investor and venture capitalist, laying the groundwork for the future of collaboration, communication, culture, and creativity. By strategically investing in and supporting companies that align with these themes, Jesse aims to contribute to the evolution of how we work and interact over the next decade and beyond.

During his time as an angel investor, he served as an key advisor to several early-stage technology startups, providing them with valuable guidance and support. Notable ventures included fitmob (acq. by ClassPass), inDinero, Jackpocket (acq. by DraftKings), Squire, and YourTrove (acq. by LiveNation).

Jesse became a General Partner at Flybridge in 2016 and has been an integral part of the last three funds leading investments in companies like Arcee, CarEdge, Chief, HiFi (acquired by Square), Imperfect Foods (acquired by Misfits Markets), Splice, and Teal. His commitment to the startup ecosystem extends beyond his role at Flybridge. Jesse built and supported a community of thousands of founders in WeWork Labs. He most recently created Next Wave NYC, a pre-seed fund that allows builders of iconic New York companies to back the next generation of founders in their community. 

Before Jesse leapt into the startup world, he led the technology group at LivePerson (NASDAQ: LPSN) and was a network security engineer for a number of Global 2000 public and private companies. His passion for technology started much earlier, in elementary school, when his third grade teacher offered an Apple IIgs computer to him to tinker with, destroy, and ultimately put it back together.

Beyond his professional activities, Jesse takes pride in his role as a devoted husband to Catherine, and a loving father to an exceptional and curious eight year old boy, and a beautiful baby girl. Their family prides themselves on traveling, with the kids, all over the world — Holden was on more than twenty four flights before he was two years old and Charlie has already traveled on more than sixteen in her sixteen months of life. Jesse has lived in NYC for over 15 years.