John Street and the business of getting out of the way

When John Street was asked what he wanted to be as a child, he began with a promisingly impractical answer: “A dinosaur!” Then came the correction. That was his brother, who liked the prospect of standing around and eating all day. Street’s own ambition took a more conventional shape in high school, when his girlfriend’s mother, a guidance counselor, suggested that he consider owning a business. One brother had identified an appealing lifestyle. The other now needed to learn accounting.

The joke suits a founder whose career can look, from a distance, like a procession of technology companies. Telephone Express. USA.NET. MX Logic. Pax8. Look closer and the connective tissue becomes more interesting. Street has repeatedly concerned himself with the arrangements that let other people get something done: make a call, manage email, buy software, build a career, sustain an orchestra. The products change. The interest in how people work together persists.

Today he is Pax8’s founder and chairman, having handed the chief executive’s job to Scott Chasin in May 2024. He also chairs the Colorado Symphony’s board. For a piano player who has spent decades assembling businesses, the combination has a certain logic. There are plenty of talented people in both settings. Making room for them is its own occupation.

First, learn the plumbing

Street studied accounting at the University of Notre Dame, attending from 1974 to 1978, and went to work at Arthur Andersen. The training gave him a practical vocabulary for business before he had a company of his own. His credentials include a Bachelor of Business Administration and a CPA qualification. The route into entrepreneurship began with learning how an enterprise accounts for itself, a useful precaution for someone planning to take responsibility for one.

There was a substantial detour. In 1980 and 1981, he served with the Peace Corps in the Philippines. His later reflections connect that experience with an emphasis on empathy and people at work. It is an unusually useful detail in a technology biography: before building organizations that would reach across countries, he had spent time serving outside the professional world in which he had trained.

Consulting work eventually brought him into troubled telecommunications businesses. A mentor persuaded him to run one of the companies he had helped turn around. By 1986, he had moved to Colorado Springs to work on a struggling long-distance provider. Telephone Express grew to annual sales of $85 million and reached No. 13 on the Inc. 500 in 1992. An accountant had become an operator, with the daily obligations that the title entails.

The next problem was hiding in the last company

Street founded USA.NET in 1995 and MX Logic in 2002. The former built an internet email business that, at its peak, managed more than 33 million mailboxes. The latter supplied email and web security and was acquired by McAfee in 2009. Across those ventures, he worked on successive complications of an increasingly connected office: getting communication online, then making that communication safer to use.

Pax8 grew out of a complication that became visible at MX Logic. A cloud service could be useful and still have a difficult journey to its customer. Traditional distribution did not supply everything a software vendor needed to scale. Someone had to make the commercial machinery work for subscriptions and for the IT businesses serving smaller customers. A new product category was arriving through an old purchasing system.

Street and his fellow founders Ryan Walsh and Klaus Dimmler started Pax8 in 2012. Its early code addressed work that rarely earns a dramatic demonstration: consolidated billing, automated provisioning and integrations with the systems IT providers already used. Technical support and education accompanied the platform. For a business buying software on behalf of many clients, these are consequential details. Each additional subscription needs to be ordered, administered and accounted for.

There was also the familiar difficulty of opening a marketplace. Vendors needed buyers. Buyers needed products worth buying. Street has described that early dependency as a chicken-and-egg problem. Neither side could be summoned simply by declaring the other inevitable. Building the company required persuading both to participate while the market itself was still learning how to buy cloud services. Distribution had acquired a new set of verbs, and everyone needed practice.

A billion-dollar business in the unglamorous middle

In April 2022, Pax8 raised $185 million in a round led by SoftBank Vision Fund 2, valuing the company at $1.7 billion. Catalyst Investors, Sageview Capital, Blue Cloud Ventures and Liberty Global Ventures also participated. The financing was intended to support technology development and expansion into additional markets. It was a substantial vote of confidence in a business whose everyday value involved making other companies’ technology easier to purchase and manage.

By November that year, Pax8 had reached a $1 billion annual recurring revenue run rate. At the time it had more than 1,500 employees and 25,000 partners supporting over 400,000 customers. Those figures describe the company at a particular stage, rather than its present size. They also describe the scale of the coordination Street and his colleagues had taken on. Every new partner brought another set of customers, subscriptions and questions.

The distinction between a run rate and a full year’s revenue matters here. Annualizing a recent recurring revenue level gives a measure of pace; it does not rewrite the previous twelve months. Street’s story benefits from keeping that accountant’s distinction intact. The growth was significant without asking a number to perform a job it was never designed to do.

The employee comes before the spreadsheet

Street’s explanation of leadership starts with the people doing the work. Keep employees engaged and motivated, he argues, and they are better placed to look after customers. That, in turn, supports the business. It is a sequence with a practical demand attached: a leader needs to know what matters to employees and act on it. A cheerful statement about culture can be written in an afternoon. Sustaining the conditions behind it takes considerably longer.

At Pax8, the emphasis included promoting people internally and allowing them to move into work that better suited their abilities. In 2019, vendor product management leader Sophie Merrifield described managers asking about her interests early in her time at the company. Her account puts a concrete action behind the idea of developing employees: someone asked a question, listened to the answer and helped make a different role possible.

“When you’re leading a team, the more adaptable you are, the more room you can give your team to be effective in their own jobs.”

John Street, 2019

Street has described looking for talent, integrity, adaptability and an ability to avoid taking oneself too seriously. The last requirement is a welcome concession to working life. A company can have demanding ambitions without requiring everyone to become a monument to them. His own enthusiasm for collaborating with his co-founders suggests a founder who enjoys the conversation about where the business might go, as well as the eventual evidence that an idea worked.

Handing over the daily decisions

On May 1, 2024, Chasin became CEO. Street stayed on as chairman, focusing on oversight and strategic activities. The successor had been Pax8’s chief technology officer since 2021, but the relationship went back much further. Street had known him for nearly three decades, across earlier technology businesses. This was a transfer between people with a long working history, carrying their experience into a new division of responsibilities.

For Street, stepping back from daily operations also gave a different shape to a familiar leadership question. Giving capable people room is easy to recommend when it concerns someone else’s department. A founder’s own job is a more personal test. Pax8’s announcement assigned operating responsibility to Chasin and oversight to Street. The distinction gave the company a new chief executive while keeping its founder involved in what came next.

Another kind of ensemble

In August 2024, Street became chair of the Colorado Symphony board, having joined the trustees in 2022. His musical involvement already stretched to the Colorado Springs Philharmonic, where he is chairman emeritus and helped the organization recover from severe financial difficulty. For an entrepreneur, the attraction of an orchestra might appear to be a pleasant change of subject. Street’s history makes it look more like a continuing commitment.

Music had also taken him into recording. He was executive producer of Jumpin’ Jazz Kids - A Swinging Jungle Tale, nominated for a Grammy in the children’s album category in 2013. He was also coaxed into playing clarinet on the recording; the engineers improved his contribution. An entrepreneur can finance an album and still need help sounding right on it. He plays piano, too. The civic role and the private pastime belong together: supporting an institution that lets musicians work, while making music himself. There are less convincing ways for a technology founder to spend his time away from technology.

The public recognition continued in February 2025, when he received the Colorado Technology Association’s Bob Newman Lifetime Achievement Award. In an August 2025 conversation with Steve McIntosh, his interests extended from employee-first leadership to the Front Range’s cultural future. His stated ambition for the region includes a stronger place for the arts. The geography remains a constant: a Colorado native building businesses with international reach and supporting institutions close to home.

Asked how he spends free time, Street offered a compact answer: “I play the piano and do all the puzzles.” It is a good place to leave him. There is a keyboard, there is a problem to work through, and there is the pleasure of making progress. After years of building companies, he still seems interested in the work itself - and in giving other people enough room to get on with theirs.