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Jesse Middleton
Co-Founder And Chief Executive Officer at Wework
My investment interests include the sharing economy, SMB platforms, mobile, SaaS, big data, consumer and e-commerce. Prior to joining Flybridge in 2016, I was an early executive at WeWork, one of the fastest growing and most valuable startups in history. I co-founded WeWork Labs in 2011, which became WeWork’s global startup incubator, and ran WeWork X, M&A, startup investments, business and digital product development as well as inside sales during my five-year tenure at the company.
Prior to WeWork, I was the co-founder and CEO of Backstory, a venture backed startup. I began my career traveling across the United States, the United Kingdom, Mexico, Israel and China as a network security engineer based in Philadelphia. I moved to New York City where I became the head of information technology at LivePerson in 2010.
Prior to Flybridge, I was an active angel investor and serve as an advisor to many early stage technology startups including 3Claps, Authenticated Digital, Benny, Camelot Metrics, Eight, fitmob (acquired by ClassPass), inDinero, Jackpocket, Leo Health, Morsel, Rukkus, Squire, Symple, Thunderclap, Uptown House and YourTrove (acquired by LiveNation).
Highlights
$1B run rate, profitable, three years after nearly going under. micro1 has become the data layer behind the frontier labs, and Flybridge is a proud investor. Congrats @aliansarinik and @micro1_ai — nobody handed you this one.
Muse had an unfair advantage when I started using it.
Instinct had already spent a few weeks teaching me how to use a personal agent.
By the time I tried Muse, I was much more comfortable handing things over. A half-formed thought was enough. The agent could come back with questions if it needed something from me.
When I asked both products for my usage, Instinct reported roughly 3,500 messages over 30 days. Muse came back with 1,686 over about two weeks, even though I'd only started using it heavily a few days earlier.
Those are the numbers they gave me, so take them for what they're worth. For context, my ChatGPT usage was in the hundreds of times per month. The step-change in how often I reached for an agent is pretty obvious.
I love to tinker with new AI agents. If you or someone you know is early-stage building something like Muse or Instinct, I'd love to chat.
Tag them below or DM me.

