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

Mar 17 · twitter

New York is, and continues to be, this incredible place for tech.

By the numbers, it’s probably the second biggest hub. But if you want great quality of life AND a thriving tech scene, it feels like number one.

When I visit the Bay Area, I get why so many tech billionaires set up there. Still, within the city of San Francisco, there’s not a ton that inspires me compared to what I find in New York.

New York is alive in every industry (arts, media, finance) and that cross-pollination creates more interesting companies, in my opinion.

With Next Wave New York, we wanted to invest in founders who embrace that ‘New York state of mind,’ which isn’t strictly about zip code. Our ultimate goal is to back creative, AI-forward founders who see the city as a big platform.

We’ve made ton of investments so far, and nearly all of them have New York roots. One we did was from the Bay Area. Funny enough, they traveled here for a generative AI demo day, won the pitch event, and that’s how we got connected. So even folks not based here recognize the stuff that makes New York special.

In a world that feels increasingly remote, New York is still a magnet for people who want to build among the energy of this city.

Mar 13 · twitter

Got my @LimitlessAI Pendant finally. Excited to see how it changes how I interact with folks in the real world. Paying full attention when having a conversation, no note-taking, no distractions, and full recall/recollection after the fact. Let's see how this goes. https://t.co/irbJXuYmVH