Dylan Massey

When a sportsbook pays you in seconds, someone built the rails for it to happen. Dylan Massey is that someone.

Interchecks is not a name most people will ever see. It sits one layer beneath the apps they actually use - the sportsbook that pays out a winning bet, the lender that funds a loan, the neobank that lets you move cash without waiting three business days. Massey co-founded the company in 2016 and took the CEO seat in September 2017, and the bet he placed was simple: card networks cost too much, settlement takes too long, and the businesses moving money deserve more control over both.

A decade later the thesis reads like infrastructure. Interchecks has processed more than $50 billion in transactions, runs out of New York City, and powers money movement for a client roster that includes FanDuel, DraftKings, BetMGM, Fanatics Sportsbook and Credit Karma Money. The product is deliberately unglamorous: rapid deposits by bank transfer or debit card, fast withdrawals across multiple methods, and the compliance scaffolding that keeps regulators comfortable. Speed is the headline. Risk management is the fine print that actually wins deals.

Massey describes the founding in the language of wagering, which is fitting for a company whose biggest customers are sportsbooks. "Early bets we made on people, markets, and bank partners proved valuable," he said when the Series B closed, "and we couldn't be more excited to enter the next phase of our growth." It is a tidy summary of a strategy that timed the legalization of sports betting state by state and built the payment layer to cash in on it.

Economics, then Goldman, then a problem worth quitting for

Massey came up through the University of Chicago economics department, a place where markets are studied with the seriousness of physics. He graduated in 2014 and joined Goldman Sachs as an analyst, the conventional next step for a sharp finance grad. He stayed until late 2017, picking up a CFA Level I certification along the way - and he kept the company running on the side until the day job became the only job.

What he saw at Goldman was the gap between how fast information moves and how slowly money does. The card networks took their cut. Settlement lagged. Reconciliation ate back-office hours. Interchecks was the answer he built instead of the deck he could have pitched: APIs and no-code tools that let any company wrap instant payments into its product, lower its costs, and stop spending nights reconciling ledgers.

He did not build it alone. The co-founding bench is stacked with payments veterans - Brandon White (CTO, ex-CDK Global), Bob Chevlin (CPO, formerly TxVia and RBS WorldPay) and Tom Mainville (EVP Technology, also ex-CDK Global). It is a team that had seen the plumbing before and knew exactly where it leaked.