1099-compliance
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Openforce Built the Back Office for the 1099 Economy - Now It Has to Make the Mess Feel Invisible
The Scottsdale company moves $5 billion a year through the unglamorous machinery behind independent work. Its bet: the winner in contractor software is the one that turns paperwork, insurance and payments into one clean trail of proof.
Interchecks
Interchecks is a New York-based payments infrastructure company that moves money fast and safely for high-volume businesses. Through a single API and a no-code Payer Portal, it powers both funding (pay-by-bank deposits, account funding) and payouts (push-to-card, real-time payments, ACH, PayPal, Venmo, and checks), layered with built-in risk controls and 1099 tax compliance. Its platform is used across online gaming, prediction markets, on-demand payroll, and digital banking, and the company says it has processed more than $50B in transactions.
Dylan Massey
Dylan Massey is the co-founder and CEO of Interchecks, a New York-based instant-payment platform that moves deposits and withdrawals for sportsbooks, lenders, fintechs and banks. A former Goldman Sachs analyst and University of Chicago economics grad, he started the company in 2016 and has built it into infrastructure that has processed more than $50 billion, powering money movement for names like FanDuel, DraftKings, BetMGM and Credit Karma Money. In 2022 Interchecks raised a $16M Series B co-led by Senator Investment Group and Standard Investments.