“I want to make my dad proud of what I’ve done for the business. That’s what drives me — to be able to be successful and make him proud.”
Continuing a Generational Legacy
Tyrone Bailey, Jr. had his eyes on a construction career from the start. Because his father works in the industry, he knew better than to believe the misconceptions about construction work being back-breaking, overly laborious or even dangerous. He knew it for what it is: a solid route to self-sufficiency; a career path worthy of supporting families with endless opportunities to learn.
“There’s a lot of money to be made,” Tyrone says. “Portland is constantly changing and growing. There’s a lot of stuff that needs to be worked on and needs to grow.”
Tyrone enrolled in Benson High School where he majored in electrical. But the next steps after graduation made him re-evaluate, and that’s when he landed on his life’s purpose: to prepare himself to take over his father’s business.
Tyrone Bailey, Sr. owns and operates Bailey’s Construction Unlimited, a full-service, MBE-certified hauling and trucking company—and a successful one, at that. For Tyrone Jr. to follow in his father’s footsteps meant he needed to prove himself worthy of the name: Tyrone Sr. is known for his work ethic, integrity and reliability, a strong reputation built over the course of his life.
“If I am blessed to take over my dad’s business, I’m living up to that [standard],” Tyrone Jr. explains. “I want to make him proud.”
It wasn’t a straightforward path for Tyrone’s father who grew up in New Orleans with his eight siblings that he helped raise. Once he found his way into construction, it took a community of relationships to help him arrive at his own business. Like so many successes in Portland’s Black community, that path led straight through Raimore Construction.
“Just being given a chance is all you really need,” says Tyrone. “For myself and my father, all we really needed was a chance.”
Tyrone’s father worked at Workhorse Construction, a Black-owned business. Workhorse hired him to drive heavy machinery and told him he could earn his own truck along the way—the seeds to start his own hauling and trucking service. When Workhorse sold to Raimore in 2012, they made good on their promise, and Bailey’s Construction Unlimited was born.
“In our family, he was the first to own a business,” Tyron says of his father. “I tell him all the time, ‘you’ve succeeded. I’m just trying to be as successful as you are.’”
Two years out of Benson, Tyrone Jr. earned his CDL and hit the road driving in-state until he turned 21 and became eligible for interstate driving. He gained valuable experience and made good money. With demand rising for products of all kinds to be delivered, and many truckers retiring, he felt job security too. But eventually, he knew he needed to augment those skills with business acumen and a construction-focused perspective. So, he turned to Raimore.
“I always kept a good relationship with the guys here at Raimore,” he says. “They knew that I was a pretty good worker, I got a good work ethic, and a good attitude, and they decided to bring me in and help me grow into a management-leadership role.”
Today, he works as a field engineer and project manager, learning to oversee every aspect of a project, from the trucking side, to asphalt, concrete, civil excavation and demolition work. The job is an ideal experience to prepare him to own a business someday.
“I always try to tell the guys I work with to pay attention to the smaller details because the smaller details will always get you into trouble. They can become bigger things,” he says. “Focusing on the details is what it takes to run the work, to properly schedule the work, to plan out the work—all these different things that come into play with running a business or any operation.”
Raimore is more than an opportunity to prepare for his future. It’s also an environment in which he can thrive and be his best self.
“One thing that’s so great about Raimore is being able to work with people who look like you, who have the same thoughts as you, who have the same feelings as you, and being able to have a voice,” he says. “Here at Raimore, I’m not a minority.”
That’s just one reason why Tyrone hopes to stay a while at the company. The other is fear—running a business is not easy, as his father knows well. Failure is a reality for many small business owners, and letting people down is a risk if the business ends up unable to perform. Alongside the risk, though, is the reward of challenging oneself to beat all expectations, to grow, to succeed, and to make people proud.
“I want to make my dad proud of what I’ve done for the business. That’s what drives me—to be able to be successful and make him proud.”