David Chessler

Active Investor

Managing Director at Chessler Holdings LLC

Sarasota, Florida

David Chessler, Managing Director at Chessler Holdings LLC is an active investor based in Sarasota, Florida. This profile covers what David Chessler backs, at which stage, and how founders can reach out in 2026.

Investor type: AngelVCPE
Stages: Seed
Invests in: FintechLending & CreditDeveloper Tools & DataGaming & EntertainmentMedia & ContentSports & FitnessMarketing & AdTech
Location: Sarasota, Florida
Typical check: $250K
Past investments: 13

Notable investments

Automated Retail Technologies LLCProtect My CarGreat White Shark Opportunity FundShark ExperienceGPS IndustriesUltimate Builders Serviceshttps://www.hustleusf.com/PlaySight Interactive Ltd.Edison InteractiveJust Baked KiosksBrick Street FarmsPlaySight Interactive

How to reach David Chessler

Angels and operators like David Chessler reply to specific, personalized notes that show real traction, not mass blasts. Build a verified list, write a note that fits their thesis, and track replies, all on Round Funded.

Frequently Asked Questions

What does David Chessler invest in?

David Chessler invests in Fintech, Lending & Credit, Developer Tools & Data and Gaming & Entertainment, typically at Seed. Match your sector and stage, then reach out with a personalized pitch.