Dreams can come true in New Jersey, VPV Transport owner Pablo Bossi proves
Las Piedras is a quaint city in Uruguay about 30 minutes north of the coastal capital Montevideo, surrounded by lush rolling hills and granite quarries. It’s a place most truckers would now find a dream spot to retire.
It’s there that José “Pablo” Bossi was born and raised—but could not rest. The year was 1987, and the South American nation was far from paradise. The country was suffering the aftershocks of economic collapse and a recently toppled military dictatorship. His mother warned she “would not have a lazy guy at home,” he recalled. Since he wasn’t into formal education, he realized “that it was going to be very tough to build a future” in the town.
Reasoning that “America is the land of the dreams,” Bossi, then 16, set his eyes on the U.S., and off he went to find success in Elizabeth, New Jersey. That’s more of a Monkey’s Paw wish than a dream, as the crack epidemic reached its zenith in ’87 and he was just outside the epicenter in Newark and New York City.
But Bossi couldn’t worry about any of that. He had a dream to fulfill. And all he had was one night’s stay at a distant relative’s house and a phone number to a job. No green card or work visa, no English, and his mother’s words echoing in his mind: “Don’t be lazy.”
DIY Skillbuilding
Great leaders know how to delegate. But when it comes to building up your own managerial skillset, as the old saying goes, “If you want it done right, you have to do it yourself.”
No one else is going to care more about which rung of the ladder you end up on, or how fast you get there. Both are dependent on how much effort you’re willing to put into career development and unlocking your leadership potential.
Keeping with that spirit, we are focusing on several leaders in the fleet maintenance sector who have climbed up to the C-suite by pulling on their own bootstraps and using methods available to everyone.
Take a look at the profiles of our other DIY leaders:
- Charles "Chas" Voyles, Jr., associate director of customer service and fleet,
International Motors: Journey from the bathroom to boardroom - Vincent Myles, president, Myles Truck Repair: Legacy repair leader leans on shop smarts, not classroom, to scale
- Tyler Neumann, director of corporate maintenance, Foodliner & Quest Liner: "Grounded approach to innovation"
He made the phone call and got a framing job at a construction company. He lasted three weeks. “You have to work three floors high on a 2x4, and that was not for me,” he said.
He found a job at a tire retreading plant. The room was hot and the tires heavy, but he kept at it, taking English classes in his off time. He also learned Portuguese, because that’s what nearly all the other workers spoke. An American joined the line and helped Bossi learn at least one new word a day.
The young immigrant had one thing going for him: an earnest charm that compelled others to help him. He used this inherent skill to befriend the truckers coming through the loading bay. One took him out for a ride, and Bossi was smitten. His father was already a trucker in the U.S., and Bossi realized owning and operating a truck could lead to his true independence. Maybe he’d own several someday. All he needed was a Class A driver’s license and enough to make a down payment.
Bossi knew he would have to take several months off to take the driving classes, so he’d have to earn enough to live on during that time. Not even 20 yet, Bossi was still in an incredible hurry, so he got three jobs at Newark airport: delivering food to the planes, and cleaning both Terminal A and B. For three months, he barely slept, working seven days a week, the airport his de facto home.
In 1990, he got his license, working a drayage route. After six months, he could finally afford a 1980 GMC Astro stocked with a Formula 300 Cummins engine and 7-speed transmission. The drawback was no working heat or A/C.
Though saturated in sweat, he said he was still ready to learn from every trucking source, “like a sponge, trying to absorb every single drop of knowledge that I could get in order to apply it later.”
He knew enough about math to know that “if you make $4, but spend $3 on the mechanic, things are not going to work.” Bossi found a shop that would allow him to pay for the repairs and do the work himself, with a tech’s oversight. He would also help around the shop when not driving.
In two years’ time, Bossi saved enough to upgrade to a 1988 Kenworth T600, known for its aero styling, a move that also helped control fuel costs. Money was even more important as he was dating his future wife, Monica, at the time. They got married in 1994, and the dream was truly beginning to materialize.
Next on the list was buying a brand-new truck. That came in 1996 when he bought a chromed-out Kenworth W900 with a studio sleeper, 550-HP CAT engine, “and as many lights as you can imagine.” It even had working A/C.
A bigger gift came soon after: the birth of his first of three daughters, Viviana. This only intensified his drive and miles traveled. He admits he missed several holidays and birthdays, driving coast to coast.
But he slowly built his fleet up, hiring new drivers, finding time to get his citizenship, and starting the company VPV Transport (for Viviana and sisters Paola and Valentina) in 2003. He has 110 trucks, all Kenworths, and serves the ports of Newark, Philadelphia, and Norfolk. The fleet does all its own maintenance, too. Bossi, now 55, keeps a set of coveralls in the office so he can climb under the trucks on occasion.
His daughters and son-in-law all work at the company. Viviana is the operations manager, Paola is the safety director, and Valentina is the shop manager. Bossi is certainly not a helicopter parent/boss.
“He kind of just threw us out there the way he had to go through it,” Viviana affirmed proudly, clarifying that he will show them first and let them figure out the rest.
Her father also “knows when it’s time to just let us go,” she added.
The family, though, is now closer than ever, catching each other up on industry trends and changes over dinner. Bossi had to miss hundreds of family dinners because of work when his daughters were young, but because of work, he spends more time with them as adults, Viviana noted.
For many, sacrifice may be the toughest leadership skill to master, but Bossi looks at it as another simple math problem.
“Especially at the beginning, you’ve got to give it 100%,” he explained. “A lot of young people say, ‘I’m young, I want to party, I want to enjoy life.’ And I tell them, ‘You’re young, you’re strong. Go to work! When you get older, and your bones and knees start to hurt, then enjoy life.’”
Bossi also pays all the help he received forward by mentoring any young owner-operator who knocks on his door for advice, Viviana said.
Nearly forty years after he left Uruguay, the big question is whether the sacrifice was worth it.
“I think it was worth it,” Bossi proclaimed without a beat. “Today we can enjoy a quality of life that I could never have imagined back in Las Piedras. My daughters are by my side every day, running this company—and that’s the real reward to me.”
About the Author

John Hitch
Editor-in-chief, Fleet Maintenance
John Hitch is the award-winning editor-in-chief of Fleet Maintenance, where his mission is to provide maintenance leaders and technicians with the the latest information on tools, strategies, and best practices to keep their fleets' commercial vehicles moving.
He is based out of Cleveland, Ohio, and has worked in the B2B journalism space for more than a decade. Hitch was previously senior editor for FleetOwner and before that was technology editor for IndustryWeek and and managing editor of New Equipment Digest.
Hitch graduated from Kent State University and was editor of the student magazine The Burr in 2009.
The former sonar technician served honorably aboard the fast-attack submarine USS Oklahoma City (SSN-723), where he participated in counter-drug ops, an under-ice expedition, and other missions he's not allowed to talk about for several more decades.





