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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
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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.
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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.123
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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.234
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
At Flybridge, we reinvented the Scout model.
Most “Scout” programs work like this:
- Scout finds deal
- VC reviews it
- VC decides yes / no
At NextWave, we gave partners the authority to make all of their own decisions. In other words, I can't veto a decision. Neither can my partners.
If two scouts agree on an investment, the check gets written. Even better, if things go well, their fund/team gets 100% of the carry.
Today, we have 50-ish scouts across four NextWave funds.
• Harvard grads backing Harvard grads • Female founders backing female founders • Big Tech alumni backing ex-colleagues • NYC operators backing NYC builders
One of our partners helps run the startup program at Anthropic in NYC. She sees founders before they've even incorporated and writes $50-100K before anyone knows they exist. That gives us 3-4 months to build a relationship and earn the right to lead their seed.
We’ve been doing things this way for a while now. I absolutely love this model, but I’m also aware that there’s a ton of other Scout programs out there doing great things. Which firms do you think are doing a great job at this? I’d love to hear/learn.

I just got a massage from a robot. It’s the first time I tried @aescape’s robot massage therapist. Honestly, it was pretty good. Other than it being a little odd that you get yourself all setup (making sure the bed is clean, etc) it was a great time. Strong “hands”, even pressure, and pleasant sounds the whole time. Highly recommend you try it out.

