Frank Gaspari and the business of starting over

Frank Gaspari arrived at FlexTG’s 2025 sales kickoff in Las Vegas wearing a designer sweatsuit. In an industry long accustomed to a suit and tie, it was a small declaration of independence. The company had gathered at the Wynn to talk about growth, recognize its salespeople, and look ahead. Gaspari had numbers to discuss. He apparently felt no obligation to dress like a spreadsheet.

The outfit is an entertaining detail in a career built around a less photogenic subject: keeping office printing working. Gaspari has spent decades finding business in that everyday obligation. He has founded companies, sold companies, and started again. The recurring move is to take something familiar and reconsider how it ought to work.

By the time of that Las Vegas meeting, he was describing a business that had expanded tenfold in nine years. Yet the more revealing thread runs back through Chicago, two earlier ventures, and an Arizona restart. Gaspari’s career has plenty of accumulated experience. He seems particularly interested in what to do with it tomorrow.

A fresh start, 2,000 miles away

His entrepreneurial career began in Chicago, where he co-founded Column Office Equipment in 1990. Image Manufacturing followed in 1998. Global Imaging Systems acquired the first company in 1999 and the second in 2004. Gaspari also served as president of the group’s Chicago Office Technology operation, whose team received multiple Chairman’s Awards for performance.

That sequence gave him experience on both sides of a business sale: creating an independent company and working inside a larger organization. It also gave him a practical education in an industry where the equipment could look much the same from one seller to another. A copier was still a copier, however enthusiastically it was introduced.

Before the next venture, he took time to review what he had learned. He later described leaving Chicago to start again roughly 2,000 miles away in Arizona. FlexPrint began in Mesa in 2005. He saw an opening in the proliferation of printers across organizations and the difficulty of managing them coherently. The familiar market contained an unresolved problem.

Gaspari’s family biography supplies a different kind of scale: he is the seventh of eight children of Richard and Isabelle Gaspari. He remains a Chicago sports fan, though his home is now Paradise Valley, Arizona, with his wife Anne and their two daughters. The businesses moved west. The sporting allegiance proved less transferable.

The sale was only the beginning

FlexPrint’s proposition concerned what happened across a customer’s organization after the equipment arrived. Gaspari described targeting businesses with many devices and multiple locations. Their needs could involve costs, processes, unnecessary printing, or environmental goals. A useful answer required understanding which problem the customer actually wanted solved.

There was an interesting complication in that approach. A business earning money from printing could help customers reduce discretionary print volume. Gaspari discussed that possibility openly. The relationship depended on delivering something the customer could measure, even when the improvement involved less of the activity that gave the industry its name.

It is an unusually practical way to think about reinvention. Gaspari worried about distinguishing the business as competitors adopted similar language. A claim of being different had to survive the meeting. The equipment might be familiar; the customer still needed a reason to answer the next phone call.

The company’s early results gave the idea some substance. FlexPrint reached the Inc. 500 in 2010, making it the second Gaspari-led business to do so after Column Office Equipment. By the 2013 Elite Dealers assessment, FlexPrint had 150 employees and approximately $30.4 million in annual revenue. Its managed print segment had grown 22% over the previous year.

Those figures describe a company already operating beyond a local dealership’s boundaries. They also help explain why the next chapter grew out of FlexPrint itself. Gaspari had a service model and a national ambition. Expanding that model would require more people, more locations, and partners prepared to join the undertaking.

A bigger map, with familiar faces

In 2015, he used FlexPrint as the platform company for FlexTG, working with Oval Partners to assemble a national group of print dealers. The aim was to serve enterprise and major accounts across the United States. For Gaspari, it was another change in the shape of the business, built on work already underway.

An acquisition strategy also means asking other founders to make consequential decisions. Dan Reilly of Caltronics described getting comfortable with the people at Oval and FlexTG before choosing the partnership. He had heard positive accounts of Gaspari through industry peers. The ability to work with the people mattered to him. Financial engineering still required a human introduction.

The company’s stated model preserves local management and services while adding national resources. That arrangement carries an obvious responsibility: a local relationship must continue to feel dependable as the organization grows around it. The attraction of joining a larger group depends partly on what happens to the business someone has already spent years building.

ProCopy became an especially important relationship. In a 2025 remembrance of colleague Mike McGuirk, Gaspari identified it as FlexTG’s first major acquisition and a turning point in the company’s development. He remembered McGuirk as someone who would deliver difficult news directly. Their partnership allowed disagreement, followed by action. That is a useful acquisition detail to remember after the celebratory photograph.

The arithmetic behind the applause

The 2024 leadership gathering supplied a clear financial snapshot. FlexTG had produced $434 million in revenue in 2023, with 9% organic growth. Gaspari and his colleagues discussed reinvestment in employees, technology, and infrastructure. The meeting recognized dealers and individual employees alongside the presentation of financial results.

The attention to infrastructure is significant. A national business must coordinate the less theatrical work of invoicing, collecting, and supporting customers. At that meeting, Gaspari repeatedly acknowledged CFO Karen Roscher’s contribution. Growth had to pay for the organization capable of handling it. A larger map creates more places for an ordinary administrative problem to become an expensive one.

The next year’s operating figures make the geographical challenge tangible. For 2024, FlexTG reported servicing more than 330,000 assets from 37 vendors across 27,000 ZIP codes. It also reported 97% client retention across more than 31,000 customers, while adding nearly 2,000 new customers. These are dated measures of the operation Gaspari was discussing in Las Vegas.

Vendor variety is central to the proposition. A customer with different brands of equipment needs the service arrangement to accommodate that mixture. FlexTG’s business is organized around providing national support for such environments. The customer buys a workable relationship across the fleet; the company takes on the complications required to deliver it.

Who gets a chance to run the place?

Gaspari can be bracingly direct. Asked in early 2020 about industry developments that concerned him, he dismissed the familiar pessimism he said he had been hearing for decades. Asked about his New Year’s resolution, he began: “Last year is over, I’m over it”. His answer turned quickly toward learning, personal reinvention, and helping the business and its employees advance.

“Last year is over, I’m over it”Frank Gaspari, January 2020

The same interest in reinvention appears in the experience of Justin Rebhun. Gaspari gave him an opportunity to run a business at 33, despite his lack of previous executive leadership experience. Rebhun later described that decision with evident appreciation. Gaspari could have recruited an established industry executive. Instead, an employee inside the organization received the chance.

Rebhun had joined FlexTG in 2018 and progressed through enterprise sales roles before becoming president of FTG Texas. His account of Gaspari’s influence emphasizes returning to basic disciplines and continuing to change. It is one concrete example of what an expanding group can offer its people: a job can develop into a responsibility that did not exist for them when they arrived.

A smaller public moment catches Gaspari in a different register. Rodney Coleman’s employee introduction series began with a photograph of the founder; its 50th installment brought him back for a conversation. Gaspari expressed pleasure at seeing employees featured and wanted viewers to recognize the people themselves. The series had grown beyond the handful of introductions he initially expected.

The help he remembers

When Gaspari talks about assisting other entrepreneurs, he returns to help he received himself. In 2023, FlexPrint supported Whole Planet Foundation’s benefit and its work providing microloans, particularly to women entrepreneurs. He connected the sponsorship to the advice, support, and practical assistance that had mattered while he was starting and growing businesses.

That interest also had a local expression. FlexTG’s 2018 national charity golf invitational brought approximately 150 clients, employees, and sponsors to Scottsdale in support of Boys & Girls Clubs of America. The event placed the company’s commercial relationships in a different setting, with a shared purpose outside its own operations.

Gaspari’s stated ambitions in 2023 included entering additional segments and geographies, strengthening social responsibility, and pursuing more sustainable business practices. They fit a career in which the next undertaking has repeatedly grown from the previous one. Two Chicago companies became experience for an Arizona company. That company became the base for a national group.

The sweatsuit in Las Vegas makes a good opening image. The recurring decision beneath it is more durable: Gaspari keeps giving himself another version of the job. There are customers to retain, people to trust, and an operation that has to work after everyone leaves the conference. Tomorrow, someone will need the printer fixed.