In New Orleans in 1996, Michael Bontrager watched an investment banker offer his client invitations to golf and hunting outings. Bontrager had brought no comparable entertainment package. His company, Chatham Financial, was five years old. For a moment, he felt he was losing a competition whose rules everyone else understood.
Then the banker left. The client confided that he did not trust him. The invitation had failed to purchase the thing Bontrager was trying to earn. It was a useful discovery for someone whose business depended on giving advice: clients could distinguish between being entertained and being looked after.
Three decades later, Bontrager is still working through the implications. His arena now includes a beer garden, a motel full of murals, rental homes, and a proposed network of trails. These are ventures in and around Kennett Square, Pennsylvania, the place where he built his financial firm. Retirement has given him a crowded desk.
01The apprentice with questions about the invoices
At thirteen, Bontrager worked for an appliance repairman for a dollar an hour. He admired the repair skills and questioned the business arrangements. Even then, he found himself wondering how he would run the operation. An adolescent who can look at a repaired washing machine and see an organizational problem is probably headed for entrepreneurship.
His childhood took him from Greenwood, Delaware, where he was born, to Cincinnati, then to rural Lancaster County. His father was a Mennonite minister. Bontrager went to Lancaster Mennonite High School and then Wheaton College, where his ambitions briefly included college soccer.
He asked his coach for a candid assessment. Competing would require making soccer his life, the coach told him. Bontrager redirected his energy toward student government and campus organizations. He could accept an unwelcome answer when it helped him decide what to do next.
He also carried a fondness for the band Kansas into adulthood. His four daughters learned the songs. A family can inherit an entrepreneurial disposition; apparently it can also inherit the playlist.
02Nine years learning the other side of the table
Bontrager earned a BA in economics at Wheaton and an MBA at Wharton. Before starting Chatham, he spent nine years at Chemical Bank in credit, corporate finance, and derivatives roles in New York and Zurich. He became a vice president in its Derivative Products Group. His apprenticeship in finance was considerably longer than his apprenticeship in appliances.
The technical problem was real. Companies faced exposure to interest rates and currencies, and derivatives could help them manage it. The people selling those instruments understood them thoroughly. Buyers needed expertise on their side of the conversation, too.
In 1991, Bontrager founded Chatham. A company buying a hedge needed to understand its price, its obligations, and its fit with the underlying business. Independent advice could have commercial value precisely because the transaction was complicated. Knowing the mathematics was part of the job. Helping the client make an informed decision was the point.
By 2015, the company reported serving more than 1,600 companies and employing nearly 350 people, with operations stretching from Pennsylvania to Europe and the Asia-Pacific region. That June, Bontrager received EY’s Greater Philadelphia Entrepreneur Of The Year award in the services category. A business begun in a home garage had acquired a rather different floor plan.
Financial founded
services award
Collective founded
03A principle with a price tag
One of Bontrager’s stories about trust begins with an error. He reversed a foreign-exchange trade and discovered the mistake minutes later. He told the client and offered to cover the difference. The client instead asked Chatham to waive its transaction fee. The offer exposed the company to a cost; it also gave the client a reason to believe the advice.
Dave Hall, the first full-time employee, joined in 1995. Bontrager needed people who could help build an institution around this way of working. His Christian faith informed his values, while colleagues could share the commitment to transparency without sharing his faith. The practical question was how to make those values survive more employees, more clients, and more decisions.
In a 2017 conversation with Luke Zubrod, the discussion extended to everyday conduct: each employee interaction and client engagement offered a chance to strengthen trust. Sometimes that meant giving advice that would cost the firm a transaction fee. The awkward detail in any corporate statement of principle is usually the moment someone has to pay for it.
“Trust is always going down, like gravity, unless you proactively work on building it up.”
From the 2017 Work and Life conversation
04The beer garden has a job to do
Bontrager stepped away from the Chatham CEO role at the end of 2018 and turned to Square Roots Collective in 2019. The new organization gathered business and nonprofit ventures around a local ambition: make it possible for people with different backgrounds and resources to participate in the same community.
Its model gives the hospitality businesses two jobs. They need to work as places people want to visit, and their profits support community causes. Square Roots describes its structure as a 501(c)(4), combining commercial activity with a broader social purpose. A customer can encounter the organization first through a meal rather than a fundraising appeal.
The Creamery makes the idea easy to picture. Bontrager began reimagining the neglected Birch Street property in 2016. It became a beer garden and gathering place, with music, families, and public events. A $1 million state grant announced in 2025 would help stabilize an unused historic portion of the site and expand its usefulness.
The unglamorous structural work belongs in the story. Community life needs somewhere to happen, and old buildings have opinions about the maintenance budget. Reusing one takes more than an attractive sketch of people enjoying themselves under lights.
05Fourteen rooms, fourteen invitations to look
Artelo, which opened in 2024 on the former Birch Inn site, turns an overnight stay into an encounter with local and regional artists. Each of its fourteen rooms has its own mural. Guests choose a room partly by choosing the artwork they will live with for the night.
The subjects include nature, history, and the Underground Railroad. In one room, the collective Mz. Icar created work connected to Harriet Tubman’s injunction to keep going. Other rooms offer other ways into the place. There is no requirement that a motel room spend its entire career looking apologetic.
This is a revealing extension of Bontrager’s interests. A property can generate revenue while giving artists a commission and visitors a reason to think about the town beyond the parking space. The commercial and cultural purposes share an address.
The Creamery’s winter programming offered another experiment. An ice rink opened in January 2023 after an idea Bontrager had raised earlier was revived by the team. The question was seasonal and practical: how could a gathering place remain lively when cold weather changed the way people used it? An operating business has to answer such questions repeatedly.
06A town is allowed to answer back
Trails introduce a different kind of connection. Kennett Trails Alliance works toward a fourteen-mile loop linking the area’s outdoor spaces. The fourteen-mile loop is a planned network with sections already open. Paths require coordination across land, organizations, and municipal boundaries. A line on a map can conceal years of conversations.
Bontrager has argued that the relationships built during that work matter beyond the trail itself. Organizations that learn to cooperate on one project may find a way to cooperate on another. That is the appeal of staying in one place long enough to see what follows an initial investment.
It also brings scrutiny. By February 2026, Square Roots affiliates owned roughly forty of the borough’s two thousand houses. Residents had raised concerns about concentrated influence and conflicts of interest. Bontrager’s answer emphasized listening and meetings. The properties included market-rate rentals, with some rented to community organizations for their clients.
A successful founder can choose a company’s direction with a freedom that a town does not owe him. Neighbors have their own plans, memories, and objections. The same proximity that makes collaboration possible makes disagreement unavoidable. Any account of Bontrager’s second career has to leave room for the people who are unconvinced.
Kennett Decides offered a concrete way to invite participation. In 2025, Square Roots and Chatham each committed $50,000 toward a $100,000 project budget, with residents proposing ideas and people living or working in the borough given a vote. It placed a defined pot of money beside a public choice. Participation became part of the procedure.
A $100,000 budget for a community project, with public proposals and voting.
07A daughter becomes a colleague
Stephanie Almanza came to the work with more than a family connection. Before joining Square Roots, she had over a decade of commercial real estate experience, including oversight of a 3,600-unit multifamily and mixed-use portfolio. Budgeting, forecasting, and property management were professional skills she brought to the table.
Father and daughter discussed their collaboration publicly on Giving Done Right in December 2024. The partnership linked his experience of starting ventures with her experience of managing real estate. Family familiarity could provide a beginning; the work still needed a professional relationship.
Today, Square Roots lists Bontrager as founder and co-CEO and Almanza as co-CEO. His daughter Kymm leads internship and workforce development, while Zubrod, another connection from Chatham, serves as chief of staff. The team makes the continuity between the two chapters visible.
In October 2025, Kennett Township supervisors voted unanimously to award Bontrager their first Medal of Merit. The recognition acknowledged work that had become part of the local landscape. By October 2026, Square Roots had added a former trolley barn to its property portfolio, with plans for its future still undisclosed.
That open question is a fitting place to leave him. The teenager studying an appliance business grew into an adviser studying the relationship between banks and clients, then a founder studying how a town might work together. There are buildings to repair, budgets to reconcile, and neighbors to persuade. Staying put has supplied Michael Bontrager with plenty to do.