Originally published on mashable.com. 

“I don’t have a credit card,” Jason Richelson’s roommate told him. “I can’t spend any money on this Internet thing.”

That thought helped pave the way for InternetCash, a financial technology company that offered prepaid cards for online shopping. InternetCash was a failure. The company launched in 1999, just before the Dot Com bubble burst. It hired too many people, purchased unnecessarily expensive software systems and invested “crazy amounts” in marketing that didn’t work.

“We made every mistake in the book,” Richelson, one of the company’s four co-founders, recalls. “InternetCash went out of business like everyone else back then.”

When Richelson decided to launch ShopKeep, another financial tech startup, nearly a decade later, he tried to apply many of the lessons he learned from the mistakes at InternetCash. Chief among those lessons: focus on growing “slowly and measured.”

Richelson started ShopKeep, a service that provides iPad point-of-sale systems to independent retailers and restaurants, in 2008 after struggling with the point-of-sale software available for the two wine shops and a grocery store in Brooklyn that he operated at the time. The startup was privately funded for the first two and a half years and was staffed with contractors. Then in late 2011, it pulled the trigger, raising outside funding for the first time and broadening its customer base.

On Thursday, ShopKeep announced that it raised a $25 million Series C round of funding. The round was led by Thayer Street Partners and brings the startup’s total funding to more than $37 million.

ShopKeep currently processes more than $1.8 billion in payments annually and is used by more than 10,000 businesses in the U.S. and Canada.

The goal, according to Richelson, is to use the latest round of funding to open up a new office on the West Coast, expand its presence in the U.S. this year through additional investments in marketing and its product teams, and later expand its operations in Europe.

Though the company is sometimes compared to Square, a mobile payments service, Richelson is quick to point out the difference.

“Square has done a really great job of making it easy to accept credit cards,” he says. “Our service is to support retailers and restaurants and help them run a better business.. Credit card processing is just one thing.”

Alissa McCue

Alissa McCue

Alissa McCue has over 10 years of marketing and public relations experience working for top brands in retail and technology. As Senior Manager of Public Relations at ShopKeep, a leading iPad Point of Sale System, Alissa is focused on highlighting ShopKeep's major achievements and thought leadership in the POS and technology space for independent businesses.