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Jesse Middleton

Jesse Middleton

General Partner at Flybridge, Co-founder of WeWork Labs and The Community Fund

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New York, New York
Joined January 2026
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Summary

Jesse Middleton is a seasoned venture capitalist and angel investor with a strong focus on community-driven companies and emerging technologies, particularly in the AI space. As a General Partner at Flybridge Capital Partners since 2016, he has led investments in numerous successful startups. His extensive investment history includes over 50 companies, both as an angel investor and a VC, demonstrating a consistent commitment to fostering innovation and supporting early-stage ventures. flybridge+2
A true community builder and entrepreneurial leader, Jesse co-founded WeWork Labs in 2011, establishing it as WeWork's global startup incubator and cultivating a thriving network of thousands of founders. This experience honed his skills in connecting entrepreneurs and providing essential resources, a philosophy he continues to apply as co-founder of The Community Fund VC and creator of Next Wave NYC, both dedicated to backing the next generation of founders. flybridge+2
Jesse's career trajectory began with a deep technical foundation as a network security engineer, traveling globally for consulting roles, and later leading IT at LivePerson. This hands-on experience with technology, starting from his early fascination with an Apple IIgs in elementary school, informs his strategic investment decisions and his ability to understand the intricacies of tech startups. flybridge+2
With deep roots in the New York City tech scene, Jesse has lived in NYC for over 15 years and actively contributes to its entrepreneurial ecosystem. He is a Board Member at Tech:NYC and has consistently championed the city's innovative spirit, with Next Wave NYC specifically designed to support the vibrant startup community there. technyc+2

Work

Education

Writing

A New Chapter for New York’s Startups: Introducing Next Wave NYC

April 12, 2024

Announces the launch of Next Wave NYC, a new pre-seed fund within Flybridge's Next Wave strategy, aimed at supporting early-stage NYC startups in AI applications and developer platforms. Discusses the importance of community and innovation in the NYC tech ecosystem.

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The Rise of Community, the Fund

September 1, 2020

Co-authored post announcing the launch of The Community Fund, a new venture fund co-founded with Lolita Taub. Details the fund's mission to invest in community-driven companies and Jesse's journey from growing up in rural Pennsylvania to becoming a VC in NYC, highlighting his passion for technology, community building, and supporting founders.

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Hobbies

Enjoys tinkering with and understanding computers, a passion that began in elementary school with an Apple IIgs. medium

Is a father to two children and a husband. x

Notes

KSKakul Srivastavasaid that if they were launching a consumer tech startup with a woman founder,
JMJesse Middleton
would be among their top picks for a pre-seed investor.

Feb 7, 2026

PKPam Kavalamsaid
JMJesse Middleton
is one of the most helpful pre-seed investors they've worked with.

Jan 21, 2026

LJLeon Jonsaid that if they were advising a first-time founder,
JMJesse Middleton
would be among their top recommendations for pre-seed investment.

Jan 16, 2026

SCSpencer Chandleesaid that if they were raising a Series A in NYC,
JMJesse Middleton
would be at the top of their list to have on their cap table.

Dec 30, 2025

JBJeff Bussgangsaid
JMJesse Middleton
is one of the most impressive founders or investors they know in New York’s tech scene.

Dec 12, 2025

JBJeff Bussgangsaid
JMJesse Middleton
is someone they've seen make a big impact helping VC portfolio companies hire great talent.

Dec 4, 2025

PFPatrick Ferdigsaid they've seen
JMJesse Middleton
consistently back promising startups at the pre-seed or seed stage in software and AI.

Oct 23, 2025

CHCharles Hudsonsaid they've seen
JMJesse Middleton
make especially thoughtful investments in areas like media, mobile gamification, or consumer platforms.

Oct 4, 2025

PKPam Kavalamsaid that if they were building a company in biotech or deep tech,
JMJesse Middleton
would be among their top choices as a founder or investor to work with.

Sep 28, 2025

CHCharles Hudsonsaid
JMJesse Middleton
is someone they trust to invest smartly across a wide range of industries at the early stage.

Jul 24, 2025