Michael Barrett and the art of letting go

Michael Barrett offered his employer three months’ notice in 2009. He was fired immediately. There went the transition plan. At 45, with four children to support, he had to work out what came next during a recession that was hardly handing out invitations. He knew outsourcing. He knew how to sell. He knew an engineer in Guadalajara named Mario Di Vece. A spare bedroom in Lincoln City, Oregon, became the starting point for Unosquare.

Seventeen years later, the more interesting part of the story is the chair Barrett no longer occupies. Giancarlo Di Vece runs the company. Barrett’s son Joel leads its commercial work. The founder has had to learn a skill that rarely appears in an entrepreneur’s first business plan: allowing other people to carry on.

Between those two moments sits a career built around human proximity. Customers, colleagues, partners, family members: Barrett keeps returning to the question of how people come to trust one another. Sometimes the answer involves financial discipline. Sometimes it involves crossing a border. On one memorable occasion, it involved being told to stop kissing the receptionist.

A salesman and an engineer, twenty years apart

Barrett grew up around Los Angeles, the son of an LAPD sergeant. He began surfing at ten, an interest that survived the arrival of business responsibilities. His education took a less direct route. He started with business, switched to theater, then settled on communications. His LinkedIn profile lists Judson University, where he studied from 1984 to 1988. The eventual profession would make use of the last of those subjects every day.

His background was in sales and marketing, including work with TCS, Xavient and Centerlogic. He came to software services through the commercial side. Knowing what a customer would buy and knowing how to build it are different skills; the partnership with Mario gave the new venture both.

Mario was twenty years younger. Barrett admired his engineering ability. Even the name the pair chose carried the partnership’s geography: one part Spanish, one part English. After finding numerous alternatives already taken, they settled on Unosquare. Barrett liked its association with the center of town. An international software business could apparently begin with the modest ambition of being somewhere people could find.

The sales pitch was a shorter distance

Unosquare connected software engineers in Latin America with businesses needing engineering capacity. Barrett’s argument for nearshoring gave time zones a starring role. An engineer close enough to work overlapping hours with a customer can ask a question while the person who knows the answer is still at a desk. A problem can become a conversation before it becomes tomorrow’s problem.

That sounds almost too ordinary to count as a business thesis. Software development supplies plenty of occasions when ordinary things matter. Requirements change. A description leaves something out. The person commissioning a feature and the person building it can use the same words and mean slightly different things. A convenient hour for a call has practical value.

Barrett also stresses that engineers need to understand the business behind the instructions. His prescription for leaders includes visiting the office, having dinner together and learning some Spanish. There is a pleasingly physical quality to this view of digital work. The software may travel instantly. Understanding still benefits from somebody getting on a plane.

Permission to distribute the money

By September 2017, Barrett was describing a business that had grown from three employees to almost 400 while remaining profitable and avoiding debt. His explanation was unusually specific. He paid attention to gross margin, limited overhead and kept a tight grip on cash leaving the company.

Shareholder distributions had to clear three hurdles together: at least 40 percent annual growth, at least 40 percent gross margin and at least 10 percent net profit margin. He also described limiting overhead to 30 percent of gross margin. The figures belonged to his operating model. They were conditions, rather than promises that every business should produce the same results.

“Bigger is not necessarily better. Debt-free and profitable is better.”MICHAEL BARRETT / 2017

It is an excellent sentence for spoiling a room’s enthusiasm for a revenue chart. His concern was the flexibility available to keep growing.

He allowed for exceptions at larger scale, including acquisition opportunities. That qualification matters in a career that would later include private-equity partners. The early rules describe how he built the business; the later transactions describe another stage of its ownership.

A lesson in greetings

Barrett’s confidence did not make him an automatic authority on every workplace he entered. Early in his work in Mexico, he watched friends and colleagues greet one another with hugs and kisses on the cheek. He adopted the practice. His partner eventually explained that his repeated greetings to the receptionist were sending the wrong message.

It is the sort of management anecdote worth preserving precisely because the manager is the person who gets corrected. Barrett had observed a custom and missed its context. Good intentions had arrived at the office without sufficient local knowledge.

He learned to pay more attention to family meals and the invitations colleagues extended. He also gave part of his annual staff address in Spanish. His point was that a leader should make the effort to learn basic language and understand what matters to the people doing the work. Running a company across several countries put him in the position of being a learner as well as a boss.

There is some theater in any annual speech. The communications graduate had found a useful reason to rehearse.

Belfast joins the conversation

In April 2017, Unosquare announced a Belfast engineering center and plans for 100 software engineering jobs by the end of 2019. Invest Northern Ireland backed the project with £650,000 of support. The company already had two engineering centers in Mexico. Belfast gave it a European location and another pool of engineers.

Barrett explained the choice in terms of available talent and a business environment that would help the operation get started quickly. In June 2019, Giancarlo said the Belfast team was on track for the original target and was examining further growth. The connection had become more substantial than a dot on a map.

Barrett’s interest in the wider industry also found an organizational home. He helped co-found the Nearshore Executive Alliance. In a later account, NeoGroup founder Atul Vashistha recalled Barrett inviting him into a group that brought together buyers, advisers and suppliers. The invitation was to help develop the market. Competitors would still compete, but first they needed customers to understand what the region could offer.

The company outgrows one person’s job

When Barrett announced the CEO handoff in 2019, he said Giancarlo had already demonstrated his ability to lead. More than 500 employees, along with customers and partners, had seen the benefits. “We are in great hands,” Barrett wrote. A founder could have filled the announcement with his own achievements. He spent it endorsing the person taking responsibility.

Family connections run through the leadership, though the jobs are distinct. Mario is Barrett’s co-founder. Giancarlo, Mario’s brother, is CEO. Joel Barrett is chief commercial officer. The company’s current leadership roster also includes executives responsible for finance, delivery, people and technology. The family relationships sit inside an operating organization with work to assign and customers to serve.

The business has continued changing. In June 2025, Ridgemont Equity Partners announced its recapitalization of Unosquare, describing more than 1,000 professionals on three continents. Its announcement said the founder and management team would remain significantly invested. It also identified debt financing for the transaction. The distinction between an early bootstrapped business and a later financed transaction deserves to survive the telling.

By 2026, Unosquare was reporting more than 2,500 projects and over 100 active clients. Its present-day offices stretch across the United States, Mexico, the United Kingdom, Colombia and Bolivia. The spare bedroom had acquired a considerably larger address book.

Retirement has several definitions

Barrett has tried another operating role since leaving Unosquare’s CEO chair. In August 2022, identity-authentication company Cozera appointed him CEO, joining founder Abrar Ahmed. Barrett and his wife Donna had been early investors. His remit included commercial planning, operations and investor relations. It was familiar territory applied to a different product: helping financial institutions authenticate customers and prevent account takeover.

His investment interests extend beyond software services. The portfolio he lists includes construction-workforce platform Toolbelt, Mexican small-business lender Aspiria, Elevate Capital and Romano Capital. In describing how he and Donna invest, he emphasizes involvement with founders and their teams. Writing a check is followed by getting to know the people responsible for making it count.

Public speaking and writing give him other places to put the experience. He has published an executive guide to nearshoring in Latin America. His current speaking work draws on entrepreneurship and the task of building businesses across borders. An audience gets the operating lessons with the awkward greetings left in.

And there is still the ocean. Barrett has surfed with Joel in Fiji; his Portland home has been described as lined with surf art and memorabilia. The connection predates the company, the titles and the succession discussion. For a founder learning to make room for the next generation, an interest that has lasted since childhood seems a useful thing to keep.