Ben Pugh’s new beginning comes with someone who has seen him begin before. At The Brydon Group, he is joining forces with Michael Chen, an old colleague from McKinsey. This will be their third time working together. In a career announcement full of forward motion, that little piece of arithmetic is the detail that holds the eye. Three collaborations mean a relationship has survived more than an introduction and a promising first conversation.
The photograph accompanying the announcement offers a pleasantly uncorporate picture of partnership. Pugh and Chen smile across a restaurant table. There are glasses, folded napkins and a baseball cap. Nobody is pointing at a chart. Business relationships require charts often enough; it is nice to encounter one that can also accommodate lunch.
Pugh is now a CEO-in-Residence at Brydon, the Washington investment firm that backs operators pursuing small-business acquisitions. His background includes actuarial work, software engineering, consulting and founding. Each occupation has its own language. His current job asks him to bring those languages into a business where other people already have their own habits, expectations and ways of getting things done.
A number worth keeping
To understand the route here, go back to Penn State. Pugh graduated from its actuarial science program in 2013. In the following January’s student newsletter, he offered advice to people coming after him. He had arrived at university without a calculus background and went on to pass his first five preliminary actuarial exams.
He also described a change in his study routine. His first exam had taken more than 400 hours of preparation. A later exam took 120, and he earned a higher score. The striking feature of those figures is the question they invite: what had become more useful about the time he spent?
A professional examination is a tidy arena for this problem. The deadline arrives. The questions appear. The result comes back. Running a business is a less courteous arrangement: several questions arrive together, the deadline moves, and the result may take months to become clear. Both settings reward the ability to reconsider a method while staying committed to the task.
That distinction gives the student episode its staying power. There is something reassuring about a future operator having once been a beginner in a demanding subject. Expertise can look inevitable when compressed into a biography. At its point of origin, it often consists of a person trying to get through the next difficult page.
Four students, one deadline
Pugh’s university years also included a different test. In 2013, he was part of the Penn State team that placed third at the University of Southern California’s Marshall International Case Competition. His teammates were Nick Fakelmann, Devin Weakland and Samantha Jarmul. USC invited 30 schools from around the world to a competition built around a 24-hour case.
The team brought together different areas of study: actuarial science and economics, marketing, accounting and finance, and supply chain and information systems. A case competition puts those disciplines in close quarters. There is a limited amount of time to make separate judgments fit into a shared recommendation. Eventually, somebody has to present the answer.
Penn State’s trustees recorded the result as the highest finish among the participating American universities. It was a team achievement, and it belongs in Pugh’s story with all four names attached. The habit of giving one person an entire team’s trophy is convenient for biographies and rather less convenient for the other three people.
For a student preparing to enter consulting, the setting supplied a useful rehearsal. Analysis mattered, but so did choosing what to say, resolving differences and working toward a common deadline. A correct calculation could contribute to the answer. It could not deliver the presentation on its own.
The founder learns about endings
After graduation, Pugh went into Deloitte Consulting as an analyst. He later worked at McKinsey, where the relationship with Chen began. His professional path then included founding RelayCare. By 2020, the company had a two-person team based in a Washington coworking space. Whatever the ambitions of a small company, two people still have only four hands.
In 2021, Pugh announced that RelayCare was winding down operations and that he would join Sidecar as Head of Business Analytics in April. His announcement began with the weather: Washington had reached 83 degrees. That opening is a small pleasure in a genre usually devoted to being thrilled, humbled and delighted before the reader learns what happened.
He thanked the family, friends and fellow entrepreneurs who had supported him. The acknowledgment matters because an ending is part of a founder’s work, too. Entrepreneurship comes with a vocabulary for launches. It has fewer elegant words for stopping, moving on and deciding where the accumulated experience might be useful next.
A winding-down announcement has to serve several audiences at once. People who helped deserve recognition. People who followed the business need to understand the change. The person making it has to find a way to carry the experience forward. Pugh’s announcement made room for gratitude alongside the next job.
The transition also complicates the usual tidy progression from consultant to founder to executive. A career can double back, change scale and exchange one kind of responsibility for another. The experience of starting a company remains part of the operator who subsequently joins an existing team. An ending does not empty the toolbox.
Five months on the calendar, one month in the work
At Covera, Pugh held a strategic analytics leadership role. A published account of a data project described an estimated five-to-six-month schedule condensed into one month with Bentley Ave Data Labs. The work moved manual processes toward automation. The account credited the collaboration with reducing ongoing maintenance costs by more than 90 percent.
These are project-level results, rather than a scorecard for one executive. Their interest lies in the kind of work they describe. Data architecture rarely lends itself to a triumphant photograph. When it improves, the visible consequence may be that somebody can finish a task without repeating yesterday’s labor.
That is a useful counterweight to the language of leadership. A business can have an articulate strategy and still depend on a cumbersome process. Making that process easier can give the strategy somewhere to stand. The people using the system are likely to notice the improvement before anyone writes a speech about it.
The work after the transaction
Brydon supplies the setting for Pugh’s next chapter. Its model connects an operator with the search for a company, the acquisition and the work that follows. The firm describes a preference for smaller businesses with recurring revenue and limited customer concentration. Those preferences belong to Brydon’s investment approach; they set the context in which Pugh is now working.
The CEO-in-Residence program includes committed capital, an onboarding process, operating resources and access to experienced advisers. Its intended destination is a business the operator can lead. There is a particular kind of patience in that sequence. The executive title arrives while the work of finding the right company is still part of the assignment.
For an owner considering a transition, the identity of the next leader can matter alongside the transaction terms. Employees will meet that leader after the papers have been signed. Customers will encounter the decisions that follow. A change of ownership becomes practical through a succession of ordinary interactions.
“Instead, I’ve chosen to help build new business models that turn novel ideas into something real.”
Ben Pugh, on joining Brydon
Pugh has described the appeal of Brydon in terms of assistance with finding a business and launching its new leadership. That leaves him able to concentrate on moving the company forward. It is an operator’s explanation of the arrangement: support has value because it makes room for work.
The familiar partner matters here, too. Chen brings his own background in consulting, mathematics, actuarial work and product leadership. Their third collaboration provides a human connection inside an institutional structure. A firm can arrange capital and advisers. A working relationship develops through experience between the people involved.
Pugh’s next chapter therefore gathers several earlier ones around the same table: technical training, collaborative analysis, the experience of a founder and the responsibilities of an executive. None supplies a ready-made answer to every business problem. Together, they offer ways to ask more useful questions.
The restaurant photograph is a fitting place to leave him. Two colleagues are starting something together again, with history behind them and work ahead. For all the formal machinery of an acquisition, a company will still need people who can make decisions together. Pugh has chosen to begin this part of his career with someone he already knows across the table.