He Went from Jail to Running a $500M Real Estate Empire—All Because He Faked an Office for a Crucial Meeting How Dale Wills, CEO of Centra Homes, turns a checkered past into unlikely success.

In 2012, Dale Wills had a problem. He believed in his company, Centra Homes, but it wasn't yet established. When he landed a meeting with a lender that was selling off a large foreclosed-on real estate portfolio, he knew that if they could get the deal done, it would put them on the trajectory they wanted and needed.

But their office was, simply, not much to look at. So, Wills did something he's been known to do throughout his career: he got industrious, asking a friend who owned an office building if they could use his space and pretend it was theirs.

Wills recalls, "When the people from Textron Financial showed up, we had coached the receptionist to tell them, 'Yes, let me get Mr. Wills for you.' She called me on my cell phone, we hustled over there, came in through the back door and marched into the conference room like the whole operation was ours."

They closed the deal.

Related: How the Founder of Dave's Killer Bread Went From Jail to Selling His Business for $275 Million

Unlikely success story

Anyone who knew Wills as a kid surely wouldn't have predicted he'd be sitting atop the preeminent residential land redeveloper in the Twin Cities area. This is a kid, after all, who listened to his third-grade teacher tell his mother he'd never amount to anything.

But his mom saw that, although her son had gotten in trouble since birth, he was motivated in ways other kids weren't.

After the third-grade teacher's pronouncement, his mom explained that her son was already raising and selling pigs ("She was a very sweet mild-mannered lady, and that was one of the only times I saw her angry," Wills recalls). His mom, however, was a realist and told her son that he was destined to be a leader—she didn't know if it was going to be in prison or the boardroom.

The prison looked more likely, especially when Wills was expelled from high school for truancy.

Gas station education

After trying an alternative school where he was literally told that he could get A's if he just showed up every day with a pencil, Wills decided that getting a job would be more useful than attending a school where nothing was expected of him. So he started filling tanks and checking oil at an old-style gas station.

While the job wasn't challenging, Wills took it seriously and after he'd worked there for six months, the owner asked Wills if he'd manage the station while the owner went on vacation.

Sixteen-year-old Wills said yes and suddenly found himself supervising three mechanics who were in their 40s and 50s while managing a franchise that was part of a large chain. "Periodically, the company would conduct inspections," Wills recalls. "I sort of knew they were coming, but we were super busy the day they came, and I didn't pay him much mind, and barely had time to talk to him."

Two weeks later, Wills received a letter informing him that they'd given the station the highest rating possible and that they couldn't believe it was being managed by someone his age.

Jail Wake Up Call

Despite possessing the kind of professionalism that made him take a job filling gas tanks seriously, Wills was arrested three times over the next few years—one time for theft, another time for fighting and a third for not stopping when he was pulled over and then running away from the police.

It was during his final jail stint that he had his wake-up call. He says, "One day in jail, I just thought, 'This isn't the life I want.' I said to myself, 'I'm going to stop goofing off, I'm going to do better, I'm going to stop doing things that don't sit well with me ethically.'" After being released, he cut himself off from friends and activities that were a bad influence, got married and started pursuing various business opportunities.

Playing the Game

If there's any proof that Wills looks entirely different from what his background suggests, it's what happens when he visits schools like Harvard and USC to make presentations and meet with students he may recruit to work for his company.

"I remember hanging out in the conference room with some of these recruits one day, in between interviews," he says. "All of them were from elite MBA programs. One asked me: 'So where'd you go to school?' 'Charles Brown,' I answered. They'd never heard of it, but I told them it was a small school in California. 'Is that where you did your graduate work?' they went on. 'Oh, no,' I said, 'that was Herbert Green.' They all looked puzzled, but no one questioned me. They just assumed these were very small but elite schools they hadn't heard of. In truth, Charles Brown was my elementary school, and Herbert Green my middle school."

Wills finds the discrepancy between his past and present amusing. "People have these ideas about what are the credentials or indicators of success," he opines. "Sometimes you just have to play the game."