Stripe’s First Employee Just Bought a Community Bank

Darragh Buckley, the founder of fintech startup Increase and Stripe’s historic first employee, has secured a major ownership stake in Washington-based Twin City Bank following recent FDIC approval, aiming to support community banking despite fierce competitor pushback.

The transaction became public after Buckley’s purchase triggered a mandatory disclosure by the Federal Reserve Board, a requirement for acquisitions exceeding a 10% threshold. Located in Longview, Washington—roughly an hour north of Portland, Oregon—Twin City Bank is a local institution now backed by one of Silicon Valley’s prominent engineering minds. While Buckley confirmed the transaction, he declined to reveal the exact size of his stake, though he is not the sole owner of the institution.

Within the financial technology sector, observers widely assumed Buckley’s move was designed to fuel the growth of Increase, his banking-as-a-service (BaaS) venture. The acquisition reportedly sparked such intense anxiety among rivals that a mysterious competing entity hired a public relations agency to pitch negative stories about Buckley and the transaction to the media. However, Buckley revealed this is actually his third investment in a Washington state community bank, asserting his motivations differ from his competitors’ assumptions.

Buckley emphasized that this investment is not an attempt to absorb the financial institution into his startup. “Twin City Bank is, and will remain, a community-focused bank,” Buckley stated, clarifying his long-term vision.

The Tech Elite’s Shortcut to Banking Infrastructure

Increase operates an advanced API platform that allows modern financial services to run programmatically, managing automated clearing house (ACH) transactions, wire transfers, and real-time payments. Its client roster features high-profile fintech enterprises including Ramp, Check, and Pipe.

As Stripe’s inaugural employee, Buckley commands deep respect as an elite engineer. His reputation is so strong that even direct BaaS competitors regularly refer clients to Increase when facing technical limitations. Like most fintech platforms, Increase relies on partnerships with FDIC-insured institutions to deliver regulated services, avoiding the immense cost and regulatory hurdles of securing a banking license. Currently, Increase partners with Grasshopper Bank and First Internet Bank of Indiana, in which Buckley holds no personal financial stake.

Bypassing the Traditional Sponsor Bank Model

To survive in the highly saturated BaaS market, some fintech founders are bypassing traditional partnerships entirely by acquiring small community banks. Notable examples include Plaid co-founder William Hockey, whose fintech Column acquired Northern California National Bank for $50 million in 2021. Similarly, former Block executives Jackie Reses and Ronak Vyas acquired and now lead Kansas City-based Lead Bank.

Why This Fintech Pioneer Rejects Sponsor Banking

Despite industry trends, Buckley insists he has no intention of transforming Twin City Bank into a dedicated partner institution for Increase or its fintech clients. He warns that overloading small banks with fintech partnerships carries severe systemic risks.

This risk was highlighted by the recent crisis at Evolve Bank & Trust—a major partner to firms like Stripe and Affirm—which suffered a massive ransomware attack shortly after receiving a Federal Reserve cease-and-desist order targeting its risk management failures. Evolve was also heavily entangled in the collapse of BaaS middleware provider Synapse.

“Twin City Bank shouldn’t support sponsor banking,” Buckley explained. “Sponsor banking requires very specific capability and capacity to supervise partners safely and soundly. Only specialized banks should do it.”

Investing in the Underdogs of Finance

Rather than seeking a corporate shortcut, Buckley positions his investment as a vote of confidence in local financial institutions. He believes the tech industry frequently undervalues the relationship-driven model of local banks.

“There’s perhaps a prevalent view in the financial technology industry that community banks can’t grow on their own. But community banks’ strength is their relationships and knowledge,” Buckley noted.

While competitors remain skeptical and watchful, Buckley has already cleared the primary regulatory hurdles. He confirmed he has received the FDIC’s formal “non-objection for control” approval, officially closing the deal.