Jesse Middleton

Jesse's venture career has been marked by a series of notable successes, a number of misses, and a deep commitment to supporting early-stage company founders. Jesse has focused on building and investing in companies developing platforms and communities at the center of the future of work. His belief that work would shift to a more distributed, global, and flexible model back in 2009 led him to becoming a key member of the founding team at WeWork where he scaled the organization to nearly 4,000 employees in dozens of cities and countries.

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.

Furthermore, Jesse's commitment to the startup ecosystem extends beyond his role at Flybridge and The Community Fund. Jesse built and supported a community of thousands of founders in WeWork Labs communities across NYC, SF, LA, and beyond. During his time as an angel investor, he served as an advisor to several early-stage technology startups, providing them with valuable guidance and support. Notable ventures in which he played an advisory role include fitmob (acquired by ClassPass), inDinero, Jackpocket, Squire, and YourTrove (acquired by LiveNation).

Before Jesse lept 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 ealier, in elementary school, when his third grade teacher offered an Apple IIgs computer to him tinker, destroy, and ultimately put it back together.

Beyond his professional accomplishments, Jesse takes pride in his role as a devoted husband to Catherine, and a loving father to an exceptional and curious seven year old boy (born on Leap Day, 2016) and a beautiful baby girl (born in 2023). Jesse has lived in NYC for nearly 15 years.