Jeff De Flavio and the art of starting again

In October 2020, Jeff De Flavio picked up the phone and asked Michael Kopko about starting a company. Kopko later remembered the month, the call, and the opportunity. The company became Pearl Health. Before the board seats and financing announcements, there was that very ordinary piece of equipment: a telephone, doing rather consequential work.

It is a useful place to meet De Flavio. His career can look like a crowded directory of companies, with founding roles and executive chairmanships arranged one after another. The phone call puts a person back into the list. Here is someone who has an idea about a business, identifies a prospective partner, and asks whether they might make it real together.

That invitation has become a recurring part of his working life. De Flavio co-founded Groups Recover Together, served as its founding CEO, and remains on its board. Through AlleyCorp, he has helped start other companies and worked alongside their leaders. His story concerns the curious interval when a problem has become clear enough to pursue, but the organization needed to pursue it is still being assembled.

A first address in New Hampshire

The first Groups location opened in Claremont, New Hampshire, in March 2014. De Flavio was still a student at Dartmouth. The location was about 30 miles from campus, close enough for an idea encountered during his education to become a business he could actually reach. A founding date can sound inevitable in retrospect. At the time, it meant opening the first place.

His educational path already crossed more than one discipline. He earned his undergraduate degree at George Washington University, studying philosophy, and later completed an MBA at Dartmouth’s Tuck School of Business. That combination gives his biography an unusual range: questions about how people ought to live beside questions about how organizations can work. The degrees belong to the record; the connection between them is an inviting way to read it.

Groups also began with other people. Joy Sun and Silas Howland were co-founders. Howland was a childhood friend of De Flavio’s, a detail that brings the early company closer to the scale of an actual life. A future collaborator can be someone who knew you long before there was a pitch to hear. The partnership had a history before the business had one.

There is a pleasing inconvenience in that fact for anyone hoping to reduce entrepreneurship to a formula. A founding team may involve expertise, timing, shared interests, and an old friendship. These are people choosing to work together, with all the familiarity and negotiation that choice implies. Even a company with ambitions beyond its first town begins with a handful of relationships.

An early account of Groups also described regular online meetings connecting staff, managers, and founders, with ideas able to move through the company. That is a more revealing organizational detail than another job title. A founder can open the first location; a growing business needs ways for people elsewhere to be heard. The meeting is a small piece of infrastructure, but it puts collaboration on the calendar.

The company before the capital

When AlleyCorp welcomed De Flavio in August 2020, its account included a revealing piece of business history. Groups and Tempest, another company he had helped found, had begun before venture backing became part of their stories. The organizations came first. Their relationship with investors developed afterward. That sequence matters in a career now closely associated with an incubator.

It places his earliest work in the practical territory of making an organization function before a financing announcement can explain it. Any founder can describe an ambition. Operating a business requires other people to understand what they are joining and what they are expected to do. De Flavio’s first CEO role put him directly inside that responsibility, before his later portfolio of chairmanships.

By November 2017, he was appearing on the business podcast A Healthy Dose as Groups’ founding CEO. The title captures a particular stage of his career: one person identified closely with the company he helped establish. In the years that followed, his public roles would multiply. The experience of starting Groups remained the first chapter to which those introductions returned.

A residence with several front doors

AlleyCorp’s public welcome arrived on August 10, 2020. The relationship was already underway. The firm said it and De Flavio had founded two companies together over the previous year. The announcement formalized a collaboration that had been doing work before it acquired an official introduction. In business, the press release sometimes arrives after the furniture has already been moved in.

The remit was broad: build companies, advise the team and portfolio, and mentor founding CEOs. Entrepreneur in Residence is a title with a faint suggestion of a comfortable chair. This version involved helping other people occupy the uncomfortable chairs that come with a new business. Founding, advising, and mentoring could sit inside the same working relationship.

The Pearl call followed that October. Kopko’s account names a partnership that also included Kevin Ryan and Ankit Patel. Four names make the company’s beginning more legible than an isolated founder portrait. De Flavio’s contribution included bringing a prospective leader into the conversation. The resulting company gave that conversation an organization, a team, and a continuing life.

The wider set of collaborations expanded. Kristin Muhlner described becoming involved with De Flavio in the creation of Affect. Chamber’s December 2023 introduction named George Aloth and Sameer Sheth alongside him as co-founders. Different companies brought different partners. The recurring element was the early work of combining an idea with people prepared to take responsibility for it.

There is a distinction between originating an idea and managing every subsequent decision. De Flavio’s roles make room for that distinction. A founding CEO, an executive chairman, and an entrepreneur in residence have different obligations. His career has included each. Reading the titles carefully reveals a changing relationship with the companies, from running the first organization to helping build and guide several others.

The chair changes; the work continues

In September 2025, Conduce entered another chapter. Switchboard announced its acquisition of the company and identified De Flavio as Conduce’s board chair. The announcement described technology and key team members joining the acquiring business. It was a concrete change in the life of an organization he had helped establish, with people and work continuing inside a larger operation.

That event belongs in the portrait because repeated founding can otherwise become an endless procession of beginnings. Companies also develop, change hands, and acquire new settings for their work. A board role places a founder near those changes. It is a different vantage point from opening a first location, yet it remains part of the same business biography.

Other projects continued growing. In July 2026, Pearl’s chief business officer described a financing package of $50 million in equity and a $60 million debt facility. Those are two forms of capital, with different terms and purposes. Together they marked another stage for the company whose origin Kopko had traced to a call six years earlier.

His own LinkedIn introduction offers a compact statement of purpose: “Seeking creative solutions to complex social problems.” The words leave considerable room for different companies and different collaborators. They also help explain why the biography keeps widening. A problem can draw him into an organization; another can lead to a new founding partnership. The public career has accumulated several forms around that recurring interest.

The next person at the beginning

For a more personal view of his working preferences, consider his recruiting questions. In a recent Operator in Residence invitation, De Flavio asks applicants to describe a difficult, unstructured problem they carried into execution. He also asks about choosing discomfort in a career and the capabilities they would hope to develop through sustained work together. These are questions about decisions made, rather than titles collected.

The invitation describes a founding partnership small enough for individual responsibility to be difficult to avoid. Its learning ambition extends beyond the immediate venture: the person who joins should eventually be better prepared to start a company themselves. Mentorship, in that description, happens through doing consequential work beside someone with experience. The apprentice is expected to have a hand on the machinery.

“someone who wants to learn by doing”

Jeff De Flavio, describing an Operator in Residence candidate

That phrase offers a modest, useful ending to a career full of company names. The first Groups location required a beginning. Pearl required partners willing to take a call further. Later ventures required new combinations of people, responsibilities, and judgment. Now another invitation is being made, with an expectation that the person accepting it will someday make a beginning of their own.

De Flavio’s biography keeps returning to that moment before the organization is fully formed. Someone must listen carefully, make a choice, and begin the work. He has occupied several chairs since Claremont. The small founding team still seems to have a place in his calendar.