Trish Higgins
A life built to last.
Family, fitness and the everyday work of ownership: Trish Higgins is building Chenmark around businesses—and a life—worth keeping.
Trish Higgins has a practical answer to the problem of wanting too much from a day: choose what matters, then give it your attention. Describing her routine in a 2023 conversation, she named three priorities—Chenmark, family and fitness. CrossFit with her husband, James, was a regular release. When the gym was out of reach, she took calls outside, walking in rain boots and a jacket through whatever Maine weather had arrived.
At home, she described putting her phone on Do Not Disturb for the children’s bedtime, returning to work afterward. The ambition was to be present for one thing at a time, with permission to leave other things imperfect. A good workout could steady a difficult working day; time with the children could do the same. Her account offers an unusually concrete picture of a long horizon: it has to fit inside an ordinary evening.
The overlap between home and work is built into Chenmark. Higgins founded the Portland, Maine, business in 2015 with James and his brother, Palmer. The three set out to buy companies from retiring owners and keep operating them. A family building its own business through the succession of other businesses brings a particular intimacy to the enterprise. The founders share both an ownership project and relationships that extend beyond the office.
Higgins came to small-business ownership from global macro research. Chenmark’s approach redirects attention from movements in financial markets to the people and practical demands inside individual companies. Cash produced by existing businesses can help fund further acquisitions. In her account to Acquiring Minds, the intention was to hold and improve those businesses over time, allowing the work already done to finance the next stage.
One acquisition made the stakes unusually vivid. Chenmark bought Cap’n Fish’s Cruises in February 2020, just before the pandemic disrupted travel. The Boothbay Harbor operator took visitors out to see whales, puffins and the Maine coast. With passenger limits constraining a short summer season, the task became intensely specific: understand what each departure cost, combine trips where appropriate and make the available capacity work. Higgins reported that the business remained profitable that season.
The setting was picturesque; the responsibility was practical. Cap’n Fish’s still presents its vessels as working platforms for coastal excursions. Pink Lady II carries up to 149 passengers, with open decks, indoor seating and a galley. Its long history in Boothbay gives the business a life that predates Chenmark. Buying it meant taking responsibility for a continuing local service, with customers arriving for an experience that had to be delivered that day.
That kind of continuity runs through Chenmark’s stated beliefs. The name itself comes from a family expression for a question mark, a small acknowledgment of uncertainty at the center of an ambitious venture. The firm emphasizes incremental improvement, measurement and relationships maintained over decades. The appeal is cumulative: a better decision today can become a stronger operation tomorrow, provided someone remains engaged long enough to do the work.
Ownership also requires learning what to leave distinctive. In a separate discussion of Chenmark’s operating culture, James explained that individual companies should retain room to express their own identities. The shared organization was meant to connect them without erasing what made each one recognizable. For an enterprise assembled through acquisitions, that is a consequential ambition: growth introduces new colleagues, histories and habits every time.
The connections are deliberately human. James described shared lunches, leadership gatherings and conversations between managers facing related problems in different industries. A company leader could call another for experience with hiring, contracts or insurance. As the collection grew, preserving that ease of contact became a challenge in its own right. Scale was useful only if people could still reach one another.
Chenmark’s recruiting language makes the expectations plain. It seeks curiosity, resilience, humility and flexibility, and puts character ahead of a polished career history. Leaders may need to move among sales, finance, recruiting and operations. It is an invitation to people who want responsibility close enough to feel its consequences, including the uncomfortable ones. The work depends on being willing to learn in public and return after setbacks.
For Higgins, the personal question remains inseparable from the investment question: can this way of working sustain a life? A business worth keeping needs owners prepared to keep showing up.