Jesse Middleton

General Partner at Flybridge. Partner at Next Wave NYC. Co-Founder of WeWork Labs.

Jesse Middleton is a prominent seed investor at Arcee.ai and a general partner at Flybridge Capital Partners. He has a significant track record in the venture capital space, having invested in over 50 companies, primarily focusing on early-stage startups that are innovating in the fields of collaboration, communication, and technology.

Career Highlights

WeWork: Jesse was a key member of the founding team at WeWork, where he played a critical role in scaling the organization to nearly 4,000 employees across multiple locations worldwide. His experience there has deeply influenced his approach to supporting startups and fostering community among entrepreneurs.
Investment Philosophy: His investment strategy emphasizes backing companies that are shaping the future of work and technology. He has a particular interest in Small Specialized Language Models (SSLMs) and their potential to transform enterprise AI solutions. His recent investment in Arcee.ai reflects this focus, as the company aims to provide secure and efficient AI model solutions tailored to specific industry needs.1 2 3
Advisory Roles: Beyond investing, Jesse has served as an advisor for several startups, helping them navigate early growth challenges. Notable companies he has advised include fitmob (acquired by ClassPass) and Jackpocket.1

Recent Involvement with Arcee.ai

In January 2024, Jesse announced his investment in Arcee.ai, which is developing a platform for training, deploying, and monitoring SSLMs. This investment aligns with his belief in the need for precision and customization in AI applications, particularly for enterprise clients. Arcee.ai's approach focuses on security and operational efficiency, allowing companies to manage their AI models within their own infrastructure, thus addressing concerns about data privacy and vendor lock-in.2 3 4

Personal Background

Jesse's background includes a role as a technology group leader at LivePerson and experience as a network security engineer. He has a long-standing passion for technology, which began in his youth. Outside of his professional life, he is a family man, residing in New York City with his wife and two children.1

Through his investments and advisory work, Jesse Middleton continues to significantly impact the startup ecosystem, particularly in the realm of AI and technology innovation.

Highlights

Nov 11 · twitter

A lot of VCs talk about "adding value beyond capital." Here's what that actually means to me:

When we started growing our portfolio at Flybridge from dozens to hundreds of companies, we faced a fundamental challenge... "How do you maintain high-touch support at scale?"

The answer wasn't hiring more partners. It was rethinking how value flows through a network.

It's simple math: If I spend an hour helping one founder, that's valuable. If I spend an hour connecting four founders who can help each other, I've created 12 potential value exchanges.

What we've learned:

The best knowledge often comes peer-to-peer
Founders trust advice from those who've just solved their current challenge
Every founder has something valuable to teach
Community creates unexpected collisions of ideas

Real examples from our portfolio:

• CTOs helping each other with technical decisions • Founders sharing hiring playbooks • CEOs advising on fundraising strategies • Teams collaborating on market insights

As the network grows stronger, it becomes a magnet for new talent, ideas, and opportunities.

The only way to play the long game is to build a community that scales beyond any one person and outlasts any single individual.

Oct 30 · twitter

Imagine user interfaces that adapt in real-time to fit individual needs—a radical shift from the one-size-fits-all approach. With GenUI, AI can generate interfaces tailored for each user, enabling new levels of personalization and engagement. check out @dpr_648 and Holley’s latest exploration into this space from @Flybridge.

View our full post about GenUI over here: https://t.co/Yxpr5SNc0q

We will be hosting an event in NYC to discuss the future of user interfaces. Make sure to register in this link: https://t.co/XrOKSlnLQA