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Jesse Middleton

Jesse Middleton

General Partner·Flybridge

New York, New York, United States

Bio

Professional summary

Jesse Middleton is a General Partner at Flybridge. The firm lists his investment interests as Future of Work, Native AI Applications, and Serial Entrepreneurs. Flybridge says he identified the remote-work shift well before COVID and was an early WeWork executive who helped scale the company to 4,000 employees across multiple continents. The firm also describes him as an angel investor with a 16x portfolio MOIC and says his recent focus has turned to full-stack AI-native applications. Jesse became a General Partner at Flybridge in 2016 and has led or contributed to investments including Arcee, CarEdge, Chief, HiFi, Imperfect Foods, Splice, and Teal.

Investment focus

Stage, sector, and overall fit

Stage

pre-seedseedpost-Series A follow-on

Sector

future of worknative AI applicationsfull-stack AI-native applicationsserial entrepreneurs

Thesis

Future of WorkNative AI applicationsSerial entrepreneurs

Notable companies

Selected portfolio companies the partner has backed

ArceeCarEdgeChiefHiFiImperfect FoodsSpliceTealWeWork

How to approach

Framing and angles for outreach

Pitch framing

Best fit for founders building AI-native workflow products or companies reshaping how people work, collaborate, or build communities.

Personalization hooks

  1. 1Frame the company as a full-stack AI-native application rather than a thin AI feature.
  2. 2Reference future-of-work or collaboration transformation if relevant.

Recent signals

What the partner has said or done recently

  • Flybridge profile states his recent focus has turned to full-stack AI-native applications.

Background

Career, education, and skills

Career history

  • Flybridge Capital PartnersGeneral Partner~2016 - Present
  • WeWorkFounding TeamPrior

Skills

Seed InvestingAI InvestingFuture of WorkCompany Building

Other partners at Flybridge

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