WePay

Bill Clerico grew up around computers and technology, studied computer science at Boston College (graduating 2007), and worked as a technology investment banker starting in 2007. After witnessing both the boom and the 2008 financial crisis, he decided he'd rather build companies than advise on them. In mid-to-late 2008, while still working as an investment banker, he kicked around ideas with his freshman year college roommate Rich Aberman, who was in law school. They got excited about making it easy to collect money from friends—splitting dinner checks, paying rent together, going on trips. On August 28, 2008, they incorporated the company and both quit their jobs to focus full-time.

Two 23-year-old kids with no payments industry experience, they literally walked into a bank branch and asked "how do we do this?" They received blank stares. The early product was rough. In year one, they processed only $15-$20 in total payment volume—just money between themselves and close friends. Year two wasn't much better at $20-$30k. But they were learning the hard way about fraud, compliance, regulatory issues, and getting banks to work with them. After about two years, they got a bank partnership and figured out the regulatory landscape. However, they realized person-to-person payments was a brutally tough business: competitors like Venmo were offering the service for free, making monetization impossible.

Around the same time, they got into Y Combinator, which gave them just enough to survive. Then in December 2009, August Capital led a $1.6-1.7M seed round (with angel Eric Dunn) post-YC. The team was tiny—just Bill, Rich, and their first employee Eric Stern. The pivot came when they realized their real competitive advantage wasn't user experience for peer-to-peer payments; it was the hard-won expertise in payments infrastructure itself. They decided to expose everything via API and let other entrepreneurs build on top of them. This meant platforms like Constant Contact, JotForm, Fiverr, Gig economy marketplaces, and niche players like Time To Pet (dog-walking marketplace) could plug WePay in and offer payments to their users without reinventing the wheel.

The old business model didn't work because trying to charge fees on peer-to-peer payments destroyed traction—people expected it to be free. The pivot to B2B API worked because they could provide genuine value: software platforms needed payments and were willing to pay for reliable, compliant infrastructure. They grew by focusing on API quality, end-user experience, speed, and customer support—not undercutting on fees (the industry standard was ~2.9% + 30 cents, mostly going to card networks, not WePay). By 2016, they were processing low single-digit billions in TPV and doubling year-over-year. The company raised multiple rounds: $1.7M (Aug 2009), $7.5M (Aug 2010), $10M (May 2011), $15M (Jan 2014), and a monster $40M Series D (May 2015) as they approached the acquisition.

In October 2017, WePay was acquired by JP Morgan Chase for a reported ~$400M. Bill (then 32) stayed on as CEO, motivated by Chase's thoughtful approach to incentivizing the team to keep growing. They were under 200 people at acquisition and planned to double the team and expand office space. Bill emphasized that the exit was a win for shareholders and allowed WePay to operate with the backing of "the best-funded FinTech startup in Silicon Valley" (now backed by Chase). Looking back, Bill credited his and Rich's lean lifestyle ($1,000/month burn rate in Boston, $2,000/month in San Jose with roommates, eating frozen Costco burgers and ramen) for giving them the runway and optionality to survive the pivot and early scaling phase.