Jesse Middleton // Flybridge
Investor on The Pitch Seasons 12, 13 & 14
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.
Nov. 21, 2025
The Hot Mic: Should You Start a Venture Fund?
Ever wanted to sit at the table in The Pitch Room and ask the VCs your burning question? Three listeners got the chance on our new segment, The Hot Mic, a live listener Q&A where you get to ask the investors anything. In this...
Nov. 12, 2025
#174 Investrio: QuickBooks for the People
Joyce and Laura are done with clunky finance tools. So they built Investrio, an AI bookkeeper for solopreneurs. With only 25 paying customers in a market where QuickBooks reigns supreme, will the VCs make an early bet? This i...
Nov. 5, 2025
#173 STAG: The Tesla of Construction Equipment?!
When Adam and Patrik met on the Slovakian National Swim team, they never imagined they'd build a startup together in the US. Can they get the VCs on board with their made-in-America electric mini skid steer, or will the blue ...
Oct. 29, 2025
#172 My Town AI: ChatGPT Meets SimCity
Nichole Sterling built the AI product she wished she had as an elected official. Will investors see the $2.2 trillion opportunity she sees? Or will this pitch get stuck in committee. This is The Pitch for My Town AI . Featuri...
Oct. 15, 2025
#170 Original Sunshine: The Best Bagel You've Never Heard Of
Co-founders Brad & David sneak into The Pitch dressed as caterers with a bagel so good you'd never know it's gluten free. Their blind taste test wins the room, but is the brand strong enough to land a deal? This is The Pitch ...
Sept. 24, 2025
#168 Finnecto: Where Deals Don’t Die
Ariel Puga wants to save deals from dying in procurement purgatory. His traction is strong, but will the investors see how big this could be in Latin America? This is The Pitch for Finnecto . Featuring investors Paige Finn D...
Sept. 17, 2025
#167 Levee: Cleaning Up Hotels' Dirty Secret
Knock, knock! AI wants to inspect your room. Al Lagunas grew up watching his mom clean hotel rooms. Now he’s building Levee, an AI-powered app to make her job easier—and keep the staff from getting yelled at. But with just on...
May 14, 2025
#163 CurieDx: AI Pocket Doctor
After a decade in the ER, Dr. Therese Canares built CurieDx—an AI-powered app that can detect strep throat from a smartphone photo with 88% accuracy. But when she pitches both a consumer and enterprise play, the investors pus...
May 7, 2025
#162 Jungle: Your AI Study Coach
Julian Alvarez wants to turn every student into a super-learner. With $1M in ARR and 180,000 monthly active users, he’s off to a strong start. Can Jungle become the Duolingo for studying, or will ChatGPT steal his lunch money...
April 23, 2025
#160 Science On Call: AI Agents… for Restaurants
Forget slick dashboards—Luisa Castellanos is betting that the future of restaurant tech support is... texting. Her startup Science On Call is already in 900 restaurants. The question is, can it scale to thousands? This is The...
April 9, 2025
#159 Aura Finance: Chasing the Ghost of Mint
With deals from LinkedIn, Figma, and a Fortune 100 giant, Kelsey Willock’s startup Aura Finance is off to a strong start. But will early traction be enough to justify a steep valuation in a competitive space? This is The Pitc...
March 19, 2025
#156 Barberino’s: Italian Luxury Takes on the American Dream
Michele Callegari has grown Barberino's to the #1 luxury men's grooming brand in Italy. Can he replicate the same success in the US – and if he does, will the Italian investors want their cut? This is The Pitch for Barberino’...
March 12, 2025
#155 Folio: The $1.2B Opportunity Nobody Saw
Cathy Huang wants to unlock millions of dollars for millions of new internships. But with her round already closed, will there be room for everyone who wants to invest? This is The Pitch for Folio . Featuring investors Jesse ...
March 5, 2025
#154 Lockstop: Secure the Bike, Save the World
Mike Burton wants to help every city turn drivers to riders with his smart bike lock. But will his “no checks under $100k” approach leave him backpedalling? This is The Pitch for Lockstop . Featuring investors Jesse Middleton...
Feb. 19, 2025
Season 13: The Human Side of Venture
A Johns Hopkins ER doctor, a Formula 1 engineer, and an artist walk into The Pitch Room... meet this season's extraordinary founders! We screened 2,000 companies, and 12 made the cut. But with negotiations turned up to 11, wi...
Nov. 20, 2024
#152 Oma Health
Khaylah Epps wants to change the face of healthcare in the south. This is The Pitch for Oma Health . Featuring investors Cyan Banister , Charles Hudson , Elizabeth Yin , Mac Conwell and Jesse Middleton . ... Watch Khaylah pit...
Nov. 13, 2024
#151 Feedback Intelligence
Is your AI hallucinating? This AI can fix it. This is Chinar Movsisyan's pitch for Feedback Intelligence . Featuring investors Cyan Banister , Charles Hudson , Elizabeth Yin , Mac Conwell and Jesse Middleton . ... Register fo...
Oct. 30, 2024
#149 Dopl
Could robots bring healthcare access to rural America? This is Ryan James' pitch for Dopl . Featuring investors Cyan Banister , Charles Hudson , Josh Muccio and Jesse Middleton . Register for our virtual Season Finale Watch P...
Oct. 23, 2024
#148 ESAI
Can a college advisor disrupt the system from the inside? This is Julia Dixon's pitch for ESAI . Featuring investors Cyan Banister , Charles Hudson , Elizabeth Yin , Mac Conwell and Jesse Middleton . Register for our virtual ...
Oct. 9, 2024
#146 ReCraft Beer
Two of Josh's favorite hobbies—beer and startups—collide in The Pitch Room. This is Dean Eberhardt's pitch for ReCraft . Register for our virtual Season Finale Watch Party on December 11th pitch.show/party Applications are no...
Sept. 25, 2024
#145 immersionED
Chad Wilson wants to disrupt history class with video games. This is The Pitch for immersionED . ... To invest with us, become an LP in thepitch.fund Register for our virtual Season Finale Watch Party on December 11th pitch.s...
Sept. 18, 2024
#144 Bridgefy
What happens when disaster strikes and the internet goes down? This is Jorge Rios' pitch for Bridgefy . ... Register for our virtual Season Finale Watch Party on December 11th pitch.show/party Applications are now open for ne...
Sept. 11, 2024
#143 Vital Audio
What if you could take someone’s vitals, using just the sound of their voice? This is Nyamitse-Calvin Mahinda's pitch for Vital Audio . Featuring investors Cyan Banister , Charles Hudson , Mac Conwell , Jesse Middleton and Le...
Aug. 21, 2024
#140 geCKo Materials
Biomimicry (noun): the design and production of materials, structures, and systems that are modeled on biological entities and processes. Founder Capella Kerst invented a material that mimics a geckos' gravity defying grip. T...
Aug. 14, 2024
#139 FutureMoney
Phil Barrar sold his last company for $65 million. Now he’s back in the game with FutureMoney , an investing platform that helps parents create generational wealth for their kids with the Junior Roth IRA™. To invest with us, ...
July 31, 2024
Season 12: Tear Down The System
A new season is here! Fourteen pitches start August 14th with one crazy season finale to tie it all together. These startups will blow your mind, and if you’re an investor on the show… your wallet. BONUS: Stick around at the ...