When Bob Goldstein looked back at the growth of Single Digits, one milestone came with an unusual unit of measurement. The company had reached 100 employees. He counted families. In 2014, he described those households as dependent on the company. For a founder whose work involved getting strangers connected to the internet, it was a revealing way to describe the connections closest to him.
A hundred people is a respectable number on a company presentation. A hundred families gives the number somewhere to go at the end of the working day. Goldstein’s remark makes his business story more interesting than a succession of rising totals. It suggests a founder looking past the transaction to the people who have to live with the result.
That concern runs through a career spent selling networks, building a Wi-Fi business with Steve Singlar, finding capital for its expansion and, eventually, helping other executives make decisions. The work changed. The question of who would take responsibility kept returning.
The customer had bought software. Now what?
Before Single Digits, Goldstein and Singlar sold networking equipment at Cabletron Systems. Goldstein disliked cold calling, although he credited it with teaching him business fundamentals. He later moved to RGS Communications, installing cable and learning the technical work. Sales had put him in front of customers. Installation put him closer to what happened after the promise.
They founded Single Digits in 2003, initially concentrating on software for guest Wi-Fi. Customers still faced the work of assembling a functioning network. By the end of 2005, the business had 12 people and was losing money. A year later, it had five people and a broader offer: a complete guest-internet service.
There is an awkward comedy in that reversal. The smaller company had accepted the larger job. A buyer could understand software perfectly well and still need someone to get the whole arrangement working. Goldstein and Singlar changed what they sold to meet that need. Their partnership helped them persist. As Goldstein put it, “It took two of us.”
A convention floor, then a financing problem
One early clue had appeared in 2002. Goldstein was consulting for a convention center that wanted wireless access for exhibitors and visitors. The venue needed a way to offer its own service. He and Singlar saw a business in giving properties the software and services to operate Wi-Fi themselves.
Their first years demanded a broad job description: support, installations, sales, marketing, finance and collecting bills. The founders were responsible for both making the promise and chasing the payment. Anyone wishing to romanticize the garage should probably spend a little time with the receivables.
Large hotel and mall deals arrived in 2007. More hotel customers followed in 2009, bringing a need for growth financing. An investment from the New Hampshire Community Loan Fund helped pay for key hires and larger premises. Within 18 months, the workforce expanded from 60 to more than 100. Growth needed room, people and money before it could become a satisfying figure on a chart.
The number that went home at night
By 2014, Single Digits had recognizable hotel groups and Simon Property Group among its customers. Its Open Network Exchange had received New Hampshire’s 2013 Product of the Year award. There were conventional business achievements available for Goldstein to celebrate.
He singled out employment. His account of management included hiring people who had been laid off, developing staff and promoting internally where possible. Expanding the office also meant trying to create a place where people wanted to work. These were practical choices about what growth should feel like to the people doing the growing.
Changing the business had required leaving some partnerships behind. Goldstein acknowledged the difficulty. A better model on paper could still mean uncomfortable conversations with people who had helped the company reach that point. His emphasis on reinvention carried that cost inside it. Changing direction does not erase the obligations accumulated along the old route.
“There are a hundred families that are interdependent on our business.”
Bob Goldstein, 2014
More capital. More responsibility.
In January 2019, GI Partners announced its acquisition of Single Digits. The company served more than 1,600 customers across hospitality, student housing, residential properties, transportation and other markets. Its offer combined authentication software with network design, installation, monitoring and round-the-clock support. The customer could buy a continuing relationship.
Bregal Sagemount exited its investment as part of the transaction. GI Partners brought experience in technology infrastructure, property management and software. For Goldstein, the announced plan included continued organic expansion and acquisitions. The financial partner was changing while the practical work of growing the company continued.
A transaction announcement gives a business a clean dividing line. Operations are less obliging. Networks still require monitoring, properties still need installations and customers still expect someone to answer. The acquisition sat on top of those daily commitments. The founder who had once helped collect the bills now had a substantially larger set of relationships to consider.
The founder changes his own job
Goldstein also changed his position inside the organization. After the acquisition, he moved from chief executive into corporate development. By the January 2020 account of the company’s expansion, Singlar was president and CEO, while Goldstein oversaw merger and acquisition activity. Their longstanding partnership was taking a different organizational shape.
The company’s purchase of Airwave Networks in 2017 had expanded its presence in student housing and doubled its size. Expansion brought additional markets and a wider leadership team. A founder could no longer solve every problem by remaining the person closest to it.
Goldstein moved to the Single Digits board in 2021. His career had come to include sales, finance, corporate development and governance. He held a bachelor’s degree in economics from the University of Southern Maine and an MBA from Plymouth State. The sequence gives his later advisory work a concrete background: he had occupied several different seats around the same growing business.
Double Digits, and the art of the useful question
His advisory practice carries a small joke in its name. After Single Digits comes Double Digits Growth. The services are familiar to anyone who has tried to take a business beyond its founders: strategic planning, performance measures, leadership development, acquisition planning, capital sourcing and exit planning.
The practice describes confidential conversations and regular meetings where needed. Some decisions require a spreadsheet. Others require a person willing to sit through an uncomfortable explanation before offering an answer. Its stated approach combines examining data with working through the choices facing the executive.
Exacom CEO Al Brisard’s testimonial describes Goldstein asking questions suited to the company’s circumstances and balancing ambition against what was achievable. That is a useful description of an advisor’s job. An executive already has plenty of possible futures. Help is valuable when it clarifies which one the business can actually afford to pursue.
The progression from operator to advisor makes sense on those terms. Goldstein’s experience supplies examples; the executive across the table still owns the decision.
Keeping the circle in New Hampshire
Goldstein is a partner at 10X Venture Partners and is based in Hollis, New Hampshire. His present work places him among founders as an investor as well as an advisor. The geography has remained consistent even as the jobs have changed.
In February 2023, he joined Stephanie Baxter on NH Business Review’s Down to Business podcast to discuss the Tech Alliance’s Ascending Leaders in Tech program. By June 2024, he was sharing his experience on a succession-planning webinar. The current program lists him among its advisors and facilitators for a course running from November 2026 to May 2027.
Those settings give a founder’s experience a different audience. A customer wants the network to work. An emerging leader wants to understand how to make the next decision. A business owner considering succession wants some idea of what may arrive unexpectedly. Goldstein’s later career has room for each conversation.
The napkin survives the anniversary
At Single Digits’ twentieth anniversary in February 2023, Goldstein recalled the beginning as “an idea written on a napkin.” The company reported more than 3,600 clients worldwide and over 400 employees. The original idea had acquired premises, colleagues, investors and two decades of consequences.
The name itself came from New England’s cold weather, as Singlar explained at the anniversary. A technology company had borrowed its identity from a local discomfort. It is an appealingly regional detail in a business built to connect people wherever they happen to be staying.
Goldstein’s work now extends into other industries. Spark Advisors identifies him as a strategic advisor and investor, with consulting and board engagements spanning energy, e-commerce and financial services. Its biography also describes his philanthropy concerning child and family homelessness.
The thread is easier to see when the totals are set aside for a moment. A venue needed usable Wi-Fi. A growing company needed financing and people. An executive needs someone to question a plan. Goldstein has spent much of his working life close to that point where an attractive idea meets the people expected to make it work. Eventually, the napkin has to become somebody’s working day.