GrailPay spent years building a cheaper consumer checkout that merchants did not urgently want. The failed pitch left behind something more valuable: payment infrastructure, failure data and a map of the risk hiding inside bank transfers.
The Iowa fintech began as a 25-cent rebellion against card fees. Its second act - invisible bank-payment infrastructure - proved durable enough for NMI to buy the company in 2026.

An armored truck outside a San Francisco restaurant exposed a stubborn payment problem. Brian Hassan and his longtime co-founder turned that small contradiction into Kickfin - software built to move restaurant tips as quickly as the dinner check.
Access Softek has spent nearly four decades building the digital front door for community financial institutions. Its unusual edge is not a flashy consumer brand, but a founder-owned platform designed to make a local credit union feel as capable as a national bank.
Voltage began by putting Lightning nodes in the cloud. Now it is selling something more ambitious: instant payment rails that engineers can call by API and finance teams can settle in dollars.
Retrace is a San Francisco AI company rebuilding the plumbing of dental insurance. Founded in 2016 by dentist-engineer Dr. Ali Sadat, it operates what it calls the first natively-built AI healthcare clearinghouse - a network that reads X-rays and clinical records, compares proposed procedures against millions of adjudicated cases, and lets payers, providers and patients see coverage, cost and payout in real time so claims settle in seconds instead of weeks. Backed by Intel Capital and SoftBank, Retrace has raised roughly $18 million to automate the paperwork that sits between a dentist's chair and an insurer's check.

Gil Akos is the co-founder and CEO of Astra, a payments infrastructure company that lets developers move money bank-to-bank in real time. Trained as an architect with graduate work at Columbia, he taught himself programming, then earned a stack of Udacity nanodegrees in machine learning and AI to build the company he imagined. Under his leadership Astra crossed $1 billion in lifetime payments processed and pushed past a $2 billion annualized run rate, positioning the company as connective tissue for instant payouts across vertical SaaS, marketplaces, and earned wage access.
Astra is a San Francisco-based fintech that gives developers a single API to move money instantly between bank accounts and debit cards. Built on rails like Visa Direct, RTP, FedNow and ACH, its platform lets fintechs, banks and enterprises embed instant disbursements, account funding and accelerated transfers without building their own payments stack - going live in about 30 days instead of six months. Founded in 2016 by Gil Akos, Sam Morgan and Zach Nolan, Astra has processed more than $1 billion in lifetime payments and is backed by FPV Ventures, Nyca Partners and others.

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.