Mitch Jacobs started with dinner. The banks came later.

Mitch Jacobs began with a problem that has troubled generations of students: dinner was elsewhere, and so was the money. At Dartmouth, he created the Green Card so students could pay businesses off campus through a prepaid account. It was an early education in a particular kind of entrepreneurship. Find the place where an ordinary purchase becomes unnecessarily awkward. Then spend rather more of your life fixing it than you originally intended.

By January 1994, the card worked at 14 Hanover businesses. The list had the agreeable variety of a college town: pizza, groceries, a service station, video rentals. Students deposited money into an account and spent the balance locally. A financial network had arrived wearing the modest disguise of an easier lunch.

Jacobs would go on to found OnDeck, the small business lender, and become its original chief executive. But the college card is a useful place to meet him. Across payment processing, credit and his current company, Plink, he keeps returning to the relationship between a business and the people buying from it. The transaction, in his telling, has considerably more work to do.

A very small network, with very real customers

The Green Card had prices, paperwork and customers who could quite reasonably complain. In early 1994, joining required $235: a $75 deposit, $150 to spend and a $10 term fee. Jacobs said 99 of the 100 students who had actively used it during the fall signed up again. More than 50 new applications arrived in the first week of winter term.

Merchant enthusiasm varied. Some restaurants welcomed additional trade; one shopkeeper saw much the same customers switching from cash. That distinction matters throughout Jacobs’s career. Making a payment easier and producing a new sale are different achievements. A merchant has excellent reasons to ask which one a financial technology company is actually delivering.

There was room for ambition without pretending the whole country had already signed up. Jacobs was considering other campuses, but said he would stay in Hanover until the operation was established. Before the grand strategy came the local business. Before expansion came getting dinner paid for properly.

The enterprise became Transaction Service Providers. Jacobs later described expanding it to 300 campuses before selling to Student Advantage in 1999. His first company had taken him from a student’s inconvenience into the daily machinery of local commerce. He had acquired a constituency as well as an occupation.

The motel with the payment processor inside

His next business, Tranvia, began in 2001. It brought several kinds of payment processing together, including credit and debit cards, gift cards and e-commerce. A merchant could deal with one service rather than treat every way of getting paid as a separate administrative adventure. Convenience becomes a respectable business proposition when enough people are inconvenienced.

The physical setting was less polished than the proposition. Jacobs recalled building the processing infrastructure in an abandoned motel in Rock Island, Illinois, complete with large generators and T1 lines. Moving money electronically still required a persuasive amount of equipment. The cloud, before it became a fashionable address, had plenty of cables.

Comdata acquired Tranvia in March 2005. Its parent, Ceridian, recorded the purchase at $8.2 million. The acquisition gave Comdata merchant processing capabilities that included authorization, settlement and reporting. This was a business handling the practical work behind card acceptance, where a transaction has to complete before anybody gets to admire the idea.

Jacobs had now worked on both a small, bounded campus payment system and the wider card networks. The repeated question was how much useful service could be built around the movement of money. Lending would provide a rather demanding answer.

When the shop’s numbers deserved a hearing

OnDeck began in 2006, after years of Jacobs hearing small business owners describe the same frustration: they believed their businesses were doing well, yet banks declined their applications. His response was to investigate the information behind the decision. A business left electronic evidence of its performance. Could a lender use that evidence more effectively?

The practical difficulty was partly economic. Reviewing a small loan could demand work that made little sense for a conventional bank. OnDeck sought to make that review less expensive by gathering and evaluating business data electronically. Its original ambition was to supply lending infrastructure. Building the machinery, however, also meant demonstrating that it could work with actual loans.

In May 2010, OnDeck reported that its platform had supported $60 million in lending to more than 2,000 small businesses. By January 2011, the company said it had passed $100 million and secured a $15 million Series C financing led by SAP Ventures. Its revenue had tripled during 2010. The proposition was moving beyond an interesting argument about bank underwriting.

Jacobs received the 2010 Ernst & Young Entrepreneur Of The Year award in Metro New York’s Emerging category. The label was apt: the business was still proving a different way to serve borrowers. Recognition and operating evidence had arrived together, which is a more useful combination than recognition alone.

The founder and the bell are different chapters

OnDeck’s early product history shows how steadily the idea became more specific. The company made its first loan in August 2007. Its first OnDeck Score, introduced in February 2009, analyzed more than 200 attributes relevant to business creditworthiness. By February 2012, the third generation used more than 800. More of the business could be examined before a lending decision was made.

The company’s leadership changed along the way. Noah Breslow became CEO and chairman in June 2012. OnDeck began trading on the New York Stock Exchange on December 17, 2014, having priced 10 million shares at $20 each. Jacobs founded the enterprise that reached the exchange; Breslow was leading it when it arrived.

The distinction gives the story its proper proportions. Founding a company, running its early years and taking it public are separate pieces of work. Jacobs’s contribution belongs in the first chapters, where a recurring complaint from merchants became an operating company. Its later milestones show how far that company traveled.

Main Street also needed a meeting room

Jacobs carried the financing question into policy discussions. He co-chaired the Micro Capital Task Force with Connie Evans, president and CEO of the Association for Enterprise Opportunity. The effort brought together participants from different parts of the financial system to examine how smaller businesses could obtain capital.

The preparatory work included more than 50 interviews with leaders from mission-focused organizations, technology companies, established financial institutions and government agencies. Recommendations were intended for Treasury, the White House and Congress. The problem demanded cooperation between people who did not necessarily share a business model, or even a vocabulary.

It is a revealing extension of his work. A useful piece of software still operates inside institutions, incentives and funding arrangements. Getting more money to a shopkeeper could require a better system and a roomful of people willing to change how their existing systems connected.

Back to the people at the register

In a 2019 essay, Jacobs returned to Charlie and Jimbo Dowd, longtime owners of Everything But Anchovies in Hanover. He remembered the point of sale progressing from paper receipts to swipe terminals and then tablets. The owners and their sisters were still greeting customers at the register.

That continuity supplied his argument for giving small businesses better personalization tools. Large retailers were investing in tailored customer experiences. The local merchant already understood the value of recognizing a regular; technology might help smaller businesses act on that knowledge more consistently. The people who sold him dinner remained part of his thinking years later.

“Digital banking gives money a user interface.”

Mitch Jacobs, August 2024

Plink brings him back to payments and the information surrounding them. The company’s team page identifies him as founder and CEO. He lives in Los Angeles with his wife, entrepreneur and author Samantha Ettus, and their three children. The college venture has become a long career, with a family life well beyond Hanover.

An advertisement asks the wrong question

Jacobs describes Plink’s inspiration as an irritation: seeing an irrelevant advertisement on Instagram, then encountering the same ad in his banking app. A bank already held information about spending. Why should its attempt to reach a customer feel so poorly informed? An annoyance on a screen had reopened an old engineering question.

His proposed answer is automated commerce: interpreting payment information and using it to deliver relevant merchant offers through digital banking. In August 2024, he said Plink’s platform served more than 300 community banks and credit unions, representing roughly 11 million cardholders. Those are his figures for that moment, rather than a present-day count.

The desired outcome is straightforward enough to describe over dinner. Customers receive offers that fit where they shop; merchants have a better basis for encouraging another visit; financial institutions help connect the two. Delivering that outcome requires the unglamorous work of identifying merchants and making transaction information usable.

There is a satisfying circularity here. Jacobs’s first enterprise connected students with nearby businesses through a card. His current work asks how existing cards and banking applications might support more useful relationships with merchants. The network has grown considerably more complicated. The person at the register still has the same reasonable question: will this help my business?