Unosquare’s Humble Beginnings Pay Off in Next-Gen Succession

Mike Barrett’s career story took an abrupt turn in 2009 when he found himself jobless and in debt, with no safety net, while scraping by to pay his mortgage and support four kids during one of the most difficult job markets in the 21st century.

At 45 years old, he had been working in the outsourcing and nearshoring space when he decided it was time for a change after recognizing differences with his employer’s leadership. He decided to give a three-month notice of his resignation, planning to use that time to find his next opportunity.

He was fired on the spot.

On Tuesday, he spoke with Nearshore Americas from his Portland home with the walls behind him lined with surf-related art and memorabilia. He talked about an upcoming family vacation to Fiji’s Tavarua Island, which he described as one of the world’s premier surf destinations.

It’s a far cry from where Barrett found himself just 17 years ago before founding Unosquare.

Now retired, the Los Angeles native speaks proudly of what the company achieved in such a short time, but he really lights up when talking about the next generation of leadership that has taken over.

Mike’s son, Joel Barrett, is the company’s chief commercial officer, and Giancarlo Di Vece is the brother of co-founder Mario Di Vece, who partnered with Mike in 2009 as a 25-year-old software engineer from Guadalajara.

“It’s unique and it’s rare that a company that’s founder-led, after 15 years, transitions to a second generation of leadership successfully,” Barrett said. “And where everyone still loves each other and gets along.”

It’s rare for a reason. The handoff from founder to successor — especially when family is involved — can and often does turn into a disaster, according to global business studies. Disputes over compensation, lingering ego, brewing resentment, lawsuits between relatives — Barrett has seen it, and he’s read the case studies.

However, much like Unosquare defied the odds in getting off the ground, it’s also defying the odds and thriving under the new guard. The handoff has resulted in shared respect, loyalty and a second generation that Barrett insists is taking the company further than he ever could.

To understand how that happened, you have to go back to the beginning — back to the moment when “founder” wasn’t a title.

Fired, Broke, and Out of Options

Rewind to the financial crisis of 2009, Barrett had no savings, no retirement fund and was about $30,000 in debt.

“I was very scared,” he said. “And the only thing I knew how to do was this whole outsourcing nearshoring thing.”

Barrett wasn’t an engineer. He had never written a line of code. What he did have was a network, a feel for what executives needed, and the ability to earn trust through a strong ethical compass and a desire to serve the customer.

During his time in the industry, he had grown fond of Mario Di Vece, who at the time was working as a project manager in Mexico and 20 years younger. He wasn’t calling to make a pitch. He was calling to tell him about his plans to leave the company he had worked for.

What Mario said surprised him.

“He said, ‘Well, I’m leaving also, and I’m going to start a company,’” Barrett recalled. “‘I’m going to do software engineering for Mexico.’ And he goes, ‘What are you going to do, Mike?’ And I said, ‘I’m going to sell software engineering from Latin America.’ So we decided to do it together over a phone call.”
Barrett borrowed $30,000 from his mother to erase his personal debt. Then he put $5,000 into the company to get it off the ground.

“I just became an animal. I became a selling, marketing and sales animal,” Barrett said.

Keeping the Lights On

Unosquare’s first wins didn’t come from a brand name or a marketing machine. They came from relationships — people who trusted Barrett enough to give him a shot.

The first client was MedAssets, a publicly traded healthcare company, which contracted with Unosquare to hire three software testers. The contract was signed, but Barrett had no laptops, desks, or cash.

So Barrett asked for help.

“I called the CTO… and I said, ‘Randy, I need you to do me a favor. When you get our invoice, I need you to pay us upon receipt of invoice.’”

Barrett got the answer he was expecting.

“No.”

MedAssets was a $400 million company. Barrett would be lucky to get paid in 60 days, the company told him.

“I said, ‘Randy, I really need you to do me a solid here, because if you don’t, we’re not gonna make it. We’re gonna actually go out of business.’”

The CTO called the CFO. MedAssets ultimately agreed to pay upon receipt — but only for six months.

That six-month grace period turned into an indefinite period. Leadership at the company changed, then changed again, but no one seemed to notice that the special payment arrangement had been set up. Barrett’s fledgling company was benefitting immensely from the cash flow provided by MedAssets’ quick payments.

“By that time, the team had grown with about 25 people,” Barrett said. “And it funded our company.”

Still, Barrett says those early years were brutal. The company that Barrett and Mario left tried to sue them. They had to settle. The former employer also tried to sue some of UnoSquare’s earliest clients.

“It was a horrifying time,” Barrett said. “It was a brutal, scary time.”

In the middle of it, an industry veteran offered him some words of encouragement. He said that when the company reached 40 employees, the pressure will seem to melt away.

“He told me, ‘Mike, when you get to 40 people, you’re going to feel like you died and went to heaven.’”

They hit 40 employees around year two or three and, sure enough, were confident in the company’s efficacy at that point.

The Culture that Scaled

Unosquare grew by getting specific. Barrett focused on healthcare, financial services and tech — verticals where executives were willing to pay for both competence and speed. The company invested in thought leadership, placing executives as experts in software delivery within those industries. The pitch wasn’t just “lower cost.” It was “faster deployment with the right people.”

And inside the company, Unosquare built a very simplistic hiring filter: SHHH — Smart, Hungry, Humble, Hardworking.

“If those employees were smart, hungry, humble and hardworking, they were very successful in Unosquare,” Barrett said. “And if they were missing one or more of those four things, they were not successful, and they did not last.”

Behind those four letters was a more immediate policy.

“You hire slow, and you fire fast.”

The other core ethic was what Barrett calls “serving through selling.” In practice, it meant telling customers the truth — even when the truth meant not taking the deal.

“Sometimes that means you don’t sell to them. Sometimes that means you refer them to a competitor,” he said. “Sometimes that means you tell them, ‘Hey, you should probably hire people internally for this.’”

It was a long game. It also built a kind of trust that’s hard to replicate, and it created customers who stuck.

Barrett says the company retained 98% of customers over its journey and expanded work with most of them. At exit, he said unosquare had about 1,200 full-time employees spread across seven countries.

The growth story is impressive on its own. But it isn’t the part that makes Barrett pause.

‘It Becomes Part of Your Identity’

Succession is where many founder-led companies break. Barrett doesn’t sugarcoat why.

“There’s a pride… on the side of the founders who are not willing to let go of the reins when they should,” he said. “Personally, I did deal with that. I struggled with it.

“It becomes part of your identity,” Barrett said. “The name Mike Barrett is forever connected to the name Unosquare. And it’s hard to give that up.

“Transitioning to the next generation is full of landmines,” he said.

Unosquare, he believes, avoided them for two reasons: strong advisors — and a strong bench built on earned credibility, not entitlement.

Earning it, not Inheriting it

The current leadership wasn’t given anything; in fact, they were treated less favorably than other employees. Joel Barrett joined the company at his father’s request, despite not feeling a drive to enter the industry and instead focusing on becoming a school teacher. His first salary? Minimum wage.

“It felt like a deviation from my path,” Joel said. “It took a couple of years to really feel like I had found my own purpose in the tech world, but at this point with 12-plus years in, it’s been such a blessing for me to have built these relaitonships spanning both industries and continents.”

Giancarlo, Mario’s younger brother, joined unosquare 12 years ago as a salesperson in Mexico. No salary, just commission.

“We refused to pay him a salary because we didn’t want to be accused of nepotism,” Barrett said.

It also mirrors what Mike and Mario went through as co-founders during the startup stage. Mike said it took about 6 years to be paid a salary that reflected the work they were doing.

Giancarlo followed Barrett on sales calls for years, learning the “bicultural, binational” work required to lead a company operating between Latin America and U.S. boardrooms. Barrett describes him as both intellectually and emotionally gifted.

“I believe he’s a way better CEO than I could have ever been,” Barrett said. “I spent years and years teaching him, and now he’s taking it to a level that I personally could never have taken it to.”

Barrett promised to teach Joel sales U.S. labor laws meant he couldn’t be commission-only, but Barrett says they paid him minimum wage plus commission.

Joel stayed and grew. Nearly 11 years later, Barrett says his son is the company’s number two leader in the business and that he possesses a “work ethic far beyond my own.”

At first, the two would talk about business constantly, but those conversations began trailing away after about a year, Mike said. But now, instead of operational discussions, the two will occasionally discuss higher-level business topics but generally avoid going into company specifics.

It was a learning curve for Mike, but his identity has become easier to let go.

Joel said his father instilled rules in him as a child, and also in unosquare as a founder. Those rules have proven to be pivotal in the company’s continued success. Lessons like “investing in the middle class in whatever city we’re working in,” have become part of the company’s culture. Sayings like “if it sounds too good to be true, it probably is,” are cliche, but it’s not incorrect.

At this point in his life, Joel is able to instill these lessons in his own children, aged 9 and 6, while also doing the same for his own team of 20 employees across the U.S. and Mexico.

Giancarlo became CEO in 2019, and all signs are pointing toward continued success for a company that has spent 17 years growing on solid business practices.

To those who have penned business studies suggesting the dangers of second-generation power transfer, it’s defying the odds. But, much like Mike’s entry into company ownership with Unosquare, defying the odds isn’t all that uncommon inside the walls of the Portland-based business.

“Onward and upward, as we like to say,” Joel said.