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

Dec 6 · twitter

Do you know an amazing fractional CTO that would want to work with a fascinating consumer/prosumer AI company we're close to? Early days but incredible traction for the top users.

Dec 4 · Business Insider

Meet 45 rising stars of the venture capital industry who stood out in 2024

Dec 2 · twitter

Decision fatigue is quietly draining us, and we’re barely noticing it.

Every day, it creeps in…

What’s for dinner? Which restaurant works with the kids? Do we have the groceries we need? Where should we go this weekend? What fits into our schedule?

Each of these decisions takes a small piece of your energy. They’re too important to ignore but not important enough to justify the mental toll they create.

This is where AI can help. Not by automating everything but by working in smarter, more intentional ways.

I call it the 80/20 approach.

→ 80% of the work is handled automatically, like organizing schedules, understanding preferences, or sorting through options.

→ 20% for human input

This creates space for meaningful decisions while letting go of the ones that drain us unnecessarily.

What decisions in your daily life feel like a grind? Where could you use an assist?

Mar 6 · blog.arcee.ai

Arcee celebrates seed round & merger with mergekit