Jesse Middleton
Flybridge
Check size: $20K – $50K
Jesse Middleton has invested in 6 startups on The Pitch, deploying $270K across categories including Live Shows, Consumer Tech, Fintech, Subscription, Fund I Portfolio, Edtech. Typical check size ranges from $20K to $50K.
Investment Thesis
What Jesse Looks For
“I am so sick of people that are building stuff for building stuff's sake.”
— S14 · Ep 2
“There are some companies where we can make a lot of money on it, but it's also great for the world. And if it only returns half my fund, I'd still feel really great about backing that company.”
— S13 · Ep 1
“If they're incredible, sometimes you just gotta bet on them. They're gonna figure it out.”
— S14
“You need to show that you have figured out some really strong, early, repeatable traction model.”
— S13 · Ep 9
About Jesse Middleton
WeWork pioneer turned maverick VC at Flybridge. After his tenure as a founding team member at WeWork, Jesse made the transition to venture capital and has backed over fifty pre-seed and seed stage companies as an angel investor and GP at Flybridge. His investment focus centers on the future of work, emphasizing areas such as creativity, culture, collaboration, and communication.
Portfolio
Investments on The Pitch6 investments
Live ShowsLIVE in NYC: 3 Startups, 3 Investors, 15 Minutes to Invest
Jesse has invested $270K across 6 companies on The Pitch since Season 12.
Episodes
Top episodes featuring Jesse31 episodes
S13FundedLockstop: Secure the Bike, Save the World
S13CurieDx: AI Pocket Doctor
S15Your AI Website Sucks. PeachWeb is the Future
S13FundedScience On Call: AI Agents… for Restaurants
S14FundedSTAG: The Tesla of Construction Equipment?!
S14My Town AI: ChatGPT Meets SimCity
S14Investrio: QuickBooks for the People
S12FundedBridgefy
S13Barberino’s: Italian Luxury Takes on the American Dream
S13FundedAura Finance: Chasing the Ghost of Mint
S13Levee: Cleaning Up Hotels' Dirty Secret
S12FundedOma Health
FAQ