Stripe’s First Hire, Now Fintech CEO, Quietly Acquires Stake in Community Bank

Darragh Buckley — Stripe’s first employee and now CEO of banking-as-a-service startup Increase — has acquired a significant stake in Twin City Bank, a small community bank in Washington. The purchase triggered a required public disclosure by the Federal Reserve, confirming Buckley now holds more than 10% of the institution.

While industry observers have long speculated that Buckley aimed to buy a bank to advance Increase’s fintech operations, he insists this is not the case. “Twin City Bank is, and will remain, a community-focused bank,” Buckley said, adding that this is his third investment in a Washington-based community institution.

Increase provides API-based financial infrastructure for companies like Ramp, Check, and Pipe. Rather than becoming an FDIC-insured bank itself, it partners with banks like Grasshopper and First Internet Bank. The BaaS space has grown crowded, and some fintechs — including Plaid co-founder William Hockey’s Column — have responded by buying banks outright. Buckley denies any such intention.

He emphasized that the investment is personal and unrelated to Increase’s operations. He also criticized the rising trend of “sponsor banking,” warning that only specialized banks should support fintech partners. Buckley’s investment has drawn scrutiny, including efforts from a rival entity to discredit the deal through media pressure.

Despite the speculation, the deal has already received FDIC non-objection approval and is finalized. Buckley frames the move as a bet on the strength of local banks: “Community banks’ strength is their relationships and knowledge,” he said.

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