Jesse Middleton was employee #5 at WeWork where he co-founded WeWork Labs, giving him rare operator experience in scaling a globally recognized community-centric company before becoming a VC at Flybridge. He focuses on helping founders identify specific 50x growth scenarios rather than incremental improvements, and actively educates founders through detailed content on fundraising, positioning, and how to stand out in pitches. Jesse Middleton was employee #5 at WeWork where he co-founded WeWork Labs, giving him rare operator experience in scaling a globally recognized community-centric company before becoming a VC at Flybridge. He focuses on helping founders identify specific 50x growth scenarios rather than incremental improvements, and actively educates founders through detailed content on fundraising, positioning, and how to stand out in pitches.