Childhood friendship bears fruit with Fiserv acquisition
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Childhood friendship bears fruit with Fiserv acquisition

“Brian and I have a tremendous amount of mutual respect for each other, and we trust one another. We also have a tremendous amount of fun along the way.”

Brian Shanahan (left), Brian Gross (middle), Jon Halpern (right) started Pineapple Payments after meeting through Halpern and Gross’ previous business, AthleteTrax. Photo courtesy of Pineapple Payments.
Brian Shanahan (left), Brian Gross (middle), Jon Halpern (right) started Pineapple Payments after meeting through Halpern and Gross’ previous business, AthleteTrax. Photo courtesy of Pineapple Payments.

If the last nine years have been a dream, don’t wake Brian Gross and Jon Halpern.

The pair, along with partner Brian Shanahan, recently signed an agreement for Fiserv, Inc. to acquire their Pittsburgh-based payments technology company, Pineapple Payments.

The deal is the latest leg of a journey that started for the lifelong friends when they were detailing cars together while still in high school.

“The car wash and detail business was our first foray into entrepreneurship,” Halpern remembered. “We were able to convince certain locations to allow us to set up shop and, you know, pester people to get their car washed and detailed.”

Fast forward a few years and the Jewish duo combined their chutzpah and drive to create AthleteTrax in Halpern’s college apartment.

That company, launched in 2012, helped sports teams and leagues manage their businesses.

Gross said that when he returned to Pittsburgh after taking a break from college, he “ended up on Jon’s couch writing code for a lot of nights, weeks and months. It felt like we went to school together, but while Jon was in class we were working on a business behind the scenes.”

After acquiring a business that allowed them to assist sports facilities with AthleteTrax, they met Shanahan, who owned Cool Springs Sports Complex in the South Hills, Halpern said.

Shanahan had recently exited the day-to-day management of Card Connect, his fourth successful company in the payment processing industry, and was beginning the process of converting Cool Springs from a driving range to a large indoor sports facility.

Shanahan used AthleteTrax’s software to manage the complex, which, as luck would have it, now included a payment solution as well. After months of working together, the three decided to start a new company, Pineapple Payments.

And in the last five years the business has grown to 25,000 clients nationwide.

“We have a fairly broad-based group,” Halpern said. “Our core business is providing payment processing, credit card and ACH [automated clearing house] processing for small- to medium-size businesses, leveraging our technology platform, to take both in-person payments, as well as online payments.”

In addition to old-fashioned customer service, value-added tools and acquisitions, Gross pointed to the people and relationships that helped Pineapple Payments find success.

“You bring people from different background and experiences,” Gross said. “I’ll put our team against any other in any other business. We have all the core competencies covered from sales and marketing to product technology to finance. These are really smart people who are good at what they do and care about what we’re trying to accomplish together.”

The primary relationship, though, is the friendship between Gross and Halpern, both 29, that began when they were 5 years old. That relationship has evolved from playing Little League, to dating girls to finding customers to raising millions of dollars, Gross said.

Jon Halpern’s (left) and Brian Gross’ friendship has evolved from the little league field to the board room. Photo courtesy of Pineapple Payments.

“It hasn’t always been easy,” he added, “but we continue to learn from each other and grow.”

“Brian and I have a tremendous amount of mutual respect for each other, and we trust one another,” Halpern said. “We also have a tremendous amount of fun along the way.”

They have chosen to work with others for whom they have the same respect, and in some cases, similar history.

Halpern called Shanahan an incredible mentor and someone he and Gross have learned a lot from. He also pointed to David Goldfarb, the company’s general counsel.

“He grew up in Squirrel Hill with us and has been with us the entire time,” Halpern said.

Although Fiserv has acquired the business, Pineapple Payments will continue to operate in Pittsburgh with Gross and Halpern at its helm.

Pineapple Payments, located on Stanwix Street, has been operating remotely since the onset of COVID-19, Halpern said. There are no plans to close or relocate the business once Fiserv completes its acquisition, nor are there plans to eliminate employees, not just in Pittsburgh, but also in Chicago, Boston and even Iceland, where Gross is currently living with his family.

The success of both AthleteTrax and Pineapple Payments still amazes them.

“When you think about the journey,” Halpern said, “that all this started because the two businesses blended together. I mean, this really started with a college idea that created AthleteTrax and a small Pittsburgh connection led to Pineapple Payments, and here we are with a transaction with a behemoth like Fiserv. It’s definitely a surreal and cool moment for the two of us.” PJC

David Rullo can be reached at drullo@pittsburghjewishchronicle.org.

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