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Jesse Middleton
InvestorGeneral Partner at Graduate Syndicate 2025 · General Partner at Flybridge Capital Partners
NYC and Boston
Writes $1.5M checks · typically $1M
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About
General Partner since 2016 focused on future of work, native AI applications, and serial entrepreneurs. A former early WeWork executive and prolific angel investor, he has led investments in companies such as Arcee, CarEdge, Chief, HiFi, Imperfect Foods, Splice, and Teal.
Contact· self-published, not guessed
Invests in
AI & Machine LearningCloud ComputingConsumerDeveloper ToolsE-commerceEnterprise SoftwareFintechFuture of WorkPropTechSaaSSocial
Investments
Investor
3ClapsAgtonomyArcee.aiBulletinChiefChurchaiCommsorCovenantDNKFamososFlyngCatHandsome AppHyrImperfect ProduceJackPocketJungleLaunch HouseLaunchHouseMarco ExperiencesOhiOmniPelgoPitzRemote YearSkillistSpliceSquireSunflowerTealWETHOSYour Auto Advocate
Per curated public sources.
Colleagues at Graduate Syndicate 2025
Network2
Investors connected to Jesse in public investor directories — a warm-intro map.
Frequently asked questions
- Who is Jesse Middleton?
- General Partner since 2016 focused on future of work, native AI applications, and serial entrepreneurs. A former early WeWork executive and prolific angel investor, he has led investments in companies such as Arcee, CarEdge, Chief, HiFi, Imperfect Foods, Splice, and Teal.
- Where does Jesse Middleton work?
- Jesse Middleton is General Partner at Graduate Syndicate 2025 and General Partner at Flybridge Capital Partners.
- What does Jesse Middleton invest in?
- Jesse Middleton invests in AI & Machine Learning, Cloud Computing, Consumer, Developer Tools, E-commerce, Enterprise Software, Fintech, Future of Work, PropTech, SaaS, Social.
- What check size does Jesse Middleton write?
- Jesse Middleton typically writes checks of $1.5M.
- What companies has Jesse Middleton invested in?
- Investments tracked here include 3Claps, Agtonomy, Arcee.ai, Bulletin, Chief, Churchai, Commsor, Covenant, DNK, Famosos, FlyngCat, Handsome App, and 19 more.
About this profile. Compiled from public sources — Graduate Syndicate 2025's own website and public professional profiles — and summarised by Fundraising Fox; every fact is kept with where it came from. Spotted an error, or would rather not be listed? Email privacy@fundraisingfox.com · How we build profiles · Your rights