A Gen Z entrepreneur drives under the influence of Hugh McColl

But here we are on Providence Road, sitting in a Lincoln Navigator about a mile from his house, blinker blinking, cars lining up behind us while we wait for an opening.

Myles McGregor, the 25-year-old driver and owner of the luxury transportation service Charlotte Immaculate, laughs at the discomfort he’s causing McColl, the 87-year-old banking legend and perhaps the most powerful person in Charlotte history.

They’ve been together now, driver and passenger, Gen Z and octogenarian, white banking legend and young Black entrepreneur, for nearly two years. Very few people in the past half-century have dared cross McColl. But when it comes to the way home, McGregor follows a computer-generated path, while McColl follows landmarks and memory.

Why it matters: Pop culture and the internet can leave you believing we’re always on the cusp of generational warfare, but McColl and McGregor always seem to find the way home.

• And along the way, their discussions on everything from dating to business reveal that for all that’s changing in this world, relationships are our most valuable currency.

“I don’t have a GPS, and we disagree about the way to go just about anywhere,” McColl says. “But it doesn’t matter. [He’s] driving. I’m not.”

I visited with McGregor and McColl a couple of times over the past few months, partially for this story, partially for the entertainment value. McColl’s advice for McGregor ranged from solid career tips (“Find what you’re good at and keep doing it.”) to navigation/life tips (“Nothing beats a straight route.”) to old Southern wisdom (“Don’t get into a pissing contest with a polecat.”).

“Whenever I go and talk to Mr. McColl I make sure to have at least two or three questions, whether that’s family questions, girlfriend questions, life,” McGregor says. “Anything just to pick his brain. I just want to soak it in.”

The big picture: McGregor represents a new generation of entrepreneurs. He’s a 2016 Davidson Day grad who founded a company that provides luxury concierge service. On any given day he may drive someone like Ernst & Young Charlotte managing partner Malcomb Coley to a meeting, or pick up a Lowe’s executive at the airport, or drive McColl and his wife, Jane, to a family funeral in rural South Carolina.

• But that’s not all: McGregor also has a digital marketing agency that, among other things, produces social media content for the Charlotte-area YMCAs.
• And oh, he’s a musician with a degree from the University of Miami’s Frost School of Music.

McColl, of course, joined a company early in his career and kept making it bigger, evolving North Carolina National Bank into NationsBank and eventually Bank of America.

• Born in 1935, he left tiny Bennettsville, SC, and went to UNC Chapel Hill before entering the U.S. Marine Corps.
• He still tells the story today about how, being a young white man from a segregated South, being a Marine taught him that people of all color and background “put their pants on the same way.”
• McColl went on to become one of the most progressive business minds in America. He loved using his “simple Southerner” persona. Once he showed up to a big meeting in New York wearing a tie with watermelon slices on it — to put everybody from business leaders to politicians under his spell, then walk out with whatever he came to get.

Zoom in: McGregor got his start in business because of his music prowess. After college at Miami, he signed an 18-month contract with a record label that included a $10,000 distribution bonus. He saved that to start his company.

“I didn’t have a lot of money, but it was enough at least to get my wheels turning,” he says, so he moved back home to Charlotte.

His father, Raki, owned an Escalade and let Myles use it to get his driving business started. Now he has 12 employees across his businesses, a fleet of six cars and SUVs, and partnerships with Lowe’s and EY.

• His first high-profile client was Coley, the EY managing partner. Coley knew McGregor’s dad, and one day he needed someone to drive to Georgia to pick up several cases of wine for his collection. McGregor nailed the assignment; Coley introduce him to a few friends, including McColl.
• McGregor’s first time driving McColl, he took Hugh and Jane to Steak 48. Along the way he tried to make one of those naked left turns. Hugh cursed. Jane told him to stop. “If he’s going to be my driver he needs to know,” Hugh replied.
• Within the next year, McColl joined Coley in helping McGregor expand his business.

Zoom out: McColl has long fed off the energy of young people and their ideas. He’s told me on countless occasions that any good city needs young professionals and diversity.

• Going back to the 1970s, McColl is credited with instituting affirmative action hiring requirements at the bank that exceeded the federal government standards.

• In more recent years, he’s helped the owners of No Grease barbershop expand their business by finding loans with lower interest rates.

Now, McColl’s relationship with McGregor, 62 years his junior, might be one of the most important. McGregor isn’t just receiving McColl’s wisdom, he’s helping McColl become OK with relinquishing some of the independence that made him great.

• McColl still drives himself many places. He has a BMW SUV and a 1993 Ford Ranger in his driveway. But for important meetings, airport trips and nights out with Jane, McColl calls McGregor.

“I read somewhere that it’s more dangerous to ride with an 86-year-old than it is with a 16-year-old,” McColl tells me. “And I have to say that I’m beginning to agree with them. They talk about your reflexes slowing down. But I think it’s your attention span. I think I don’t pay nearly as much attention to the road as I used to. I get distracted by looking at something and I’ll look at it too long and nearly run into somebody all the time.”

Back to that late January morning, waiting on Providence Road to make a left.

• “Turns out I would’ve definitely been right,” McColl jokes about his way vs. McGregor’s way.

We’d driven here from west Charlotte, where McColl had a meeting at the offices of the architecture firm Shook Kelley near Five Points.

• All along the route, McColl’s delivered little history lessons. When we arrived at an intersection near the campus of Johnson and Wales, McColl said, “I built this building there, the flatiron like building. People said this will never be developed, but of course, we put a million square feet [of office space] right here.”

At Trade and Tryon streets, the heart of Charlotte, to our right was Thomas Polk Park, which the city recently announced would be rebuilt and renamed for McColl. To our left was the tallest building in the city, Bank of America Tower, which McColl built.

“When was the last time you went to the tower?” McGregor asked.

“Last week,” McColl said. “I go about once or twice a week to my office. But I’m only on [floor] 41 now, so it’s not quite as good a view as it used to be. … I moved from 58 to 54 [after retiring from the bank], and then when we founded McColl Partners I moved to 51. And then after we sold McColl Partners and founded Falfurrias Capital and moved to 41.”

McColl pauses and considers the passing years.

• “I say if I live to be 100 I’ll be on the ground floor,” he says of his office demotions.
• “You’ve got some time before that,” McGregor says.
• “Yeah,” McColl says. “13 more years.”