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Rutland County's Al Wakefield: 'I Take For Granted The Fact That I Stand Out'

Al Wakefield wears a hat, sunglasses and a multi-colored sweater in a Miami blue Porsche.
Nina Keck
Al Wakefield was born in Harlem in 1938 and spent much of his childhood in Columbia, S.C. during the Jim Crow era. He credits his grandmother's high expectations for setting him on a path to success in business, which eventually brought him to Mendon, Vt.

James Alvin Wakefield — he goes by Al — worked in New York City for a number of Fortune 500 companies, including: Mobil, Celanese, Singer and Avon. But in 1984, he moved to Mendon and made Rutland County his base for Wakefield Talibisco International, a global executive search firm.

Mary Cohen, executive director of the Rutland Region Chamber of Commerce, calls Wakefield a pioneer in Vermont’s remote worker concept.  He was also one of just a handful of black people living in Mendon.

(Full disclosure, Wakefield also served on VPR's board of directors).

At home

Wakefield's home is filled with artwork, family photos and musical instruments. He plays the flute and saxophone, and there are some African-style drums in the living room.

At 81, Wakefield still does a bit of consulting for his business.  But during an interview in his upstairs office, he admits he now spends more time practicing Bach and Mozart than anything else.

His other passion is in the garage.

“I’m driving a Porsche Targa 911 — I just got it,” he said. “This one is Miami blue. Yeah, it looks Miami gray now ... It’s all dirty with mud, I drive it in every kind of weather. I just gotta drive it,” he added, laughing.

Sitting in the seat of his expensive sports car, Wakefield is a long trip away from his humble beginnings. 

Wakefield was born in Harlem as an only child. He said his father, James, was an entrepreneur who struck out on his own at 15.  His mother Dorothy, who went by Dot, had a clerical job with New York’s Department of Motor Vehicles. She was tough, he said, and smart.

“She was extremely bright. High school education, no college,” Wakefield said. “But she was one of these people who read the New York Times every day and worked the Sunday New York Times crossword puzzle without the dictionary.”

Al Wakefield in a teal-blue Porsche.
Credit Nina Keck / VPR
Al Wakefield admits he has a thing for Porsches. He's owned them since the 1960s, and currently drives a 911 Targa in Miami blue. He said he likes colors that stand out.

His parents' marriage didn't last, however, and when Wakefield was 6, his mother sent him to live with his paternal grandparents in Columbia, South Carolina. James Wakefield, his grandfather, was a blacksmith and chauffeur. His grandmother, Carrie Ola, had just a fifth-grade education, but ran a boarding house and Wakefield says she helped put his uncle through dental school. 

“My grandmother was a little 4-foot-9, 4-foot-10 at best, obviously black woman, who believed that anybody that stayed with her had to get a college education, had do something meaningful in life," Wakefield said.

And for the most part, he said, all of the young black men who stayed there were on their way up. He remembered his grandmother always left one room available for black travelers.

Wakefield said he was amazed to see his grandmother’s name listed in a copy of the Green Book on display at the Smithsonian Museum. The Green Book was the Jim Crow-era guidebook for black travelers who couldn't stay at most establishments run by white people.

Looking back, Wakefield believes his grandmother’s high expectations and the professional black men he encountered at her boarding house had a big influence on him.

As an adult

After high school in South Carolina, Wakefield worked his way through New York University, where he studied English, German and philosophy.

Following his college graduation, Wakefield joined the Air Force in 1960 and spent the next six years flying and navigating B-52s. He was promoted to the rank of captain.

While Wakefield said he hated being in the service, he admitted it also taught him organization and discipline, as well as how to manage people and get along.

“Without any question, I think it gave me the base credentials which subsequently got me into corporate life," he said.

Al Wakefield smiles for a photo.
Credit Nina Keck / VPR
When when he first moved to Rutland, Al Wakefield said people weren't sure what to make of him. Now he volunteers as a mentor, serves as a justice of the peace in Mendon and is on several nonprofit boards.

In the late 1960s and 70s, Wakefield worked his way up at a number of Fortune 500 companies. He eventually became vice president of personnel worldwide at Avon, where he said he oversaw about 2,200 employees.

Along the way, Wakefield met Jerry Roche, a legendary headhunter who found CEOs for Apple, IBM and Walt Disney Company.

“Roche was a guru in the industry,” Wakefield said. “And he had just come from doing a search for the head of CBS, and he’d been working until 3 or 4 o’clock in the morning, and he told me the whole story ... And I said, ‘Wow, that sounds really exciting. That’s what I want to do.’”

Wakefield left his job at Avon to join one of the leading executive search firms in New York City, and he said he loved it.

But he also loved Vermont. Wakefield had been coming up to ski with friends since college, and in 1984, he and his then-wife, Patricia, moved with their two young children to Mendon. There they bought a restaurant in Rutland called Royal’s Hearthside and launched a gourmet food shop.

The restaurant had been started by a chef named Ernie Royal, who was the first black member of the National Restaurant Association. Wakefield said Royal took him under his wing and was wonderful, but the business wasn’t the right fit. Within two years, Wakefield went back to headhunting.

'Happy being a black guy in business'

Later on, Wakefield said he heard how people in town weren’t sure what to make of him at first.

“I take for granted the fact that I stand out,” he said. “When we bought the business from Ernie Royal, I remember standing out in front of the restaurant, and I had my hat on, and I guess I was just looking around at something, and I was subsequently told that people thought — some people, official people — thought that in fact, I was probably not a fine, upstanding person.”

He heard people thought he might be selling drugs, or that he was some sort of undercover agent.

“I know it had to do with — in fact one guy told me —that it had to do with being black, wearing hats, dressing flamboyantly and having an attractive white wife," he said.

Despite that, Wakefield fell in love with Rutland. And while he said bigotry exists in Rutland like it does everywhere, he also said he and his children have not experienced very much racism there.

"There are bad people around here, but they're by far the minority of people," Wakefield said. "This town is filled with really, really good people."

Al Wakefield plays a saxophone.
Credit Nina Keck / VPR
Now that he's almost completely retired from his executive search business, Al Wakefield said he has more time for passions like music and reading. He plays flute and saxophone with classical and jazz groups in the area.

In 1993, he and a colleague created Wakefield Talabisco International, and dozen years later, Wakefield launched Wakefield Global. Both executive search firms have taken him around the world. 

Wakefield married his second wife, Barbara Jeromin, in 2001. He said as he approaches his 82nd birthday, he feels lucky to have been born at what he calls the exact right time in history: He wouldn't have wanted to be born any earlier, but with today's news, he isn't sure he would want to be around in 100 years, either.

“I’ve been run out of Alabama," Wakefield said. "My then-wife and I were stoned and shot at in Selma a week after Martin Luther King walked across the Pettus Avenue bridge. I’ve been fortunately or unfortunately the only black to do this, that or the other."

But, Wakefield added:

“You could give me all the money in the world to be a white guy in business, I’m happy being a black guy in business. I’m happy being a black guy, period."

At the end of his interview with VPR, Wakefield picked up his saxophone and turned on some jazz to play along to.

"Living now feels good," he said. Then he started to play.

February is Black History Month, and all this week, VPR is featuring black entrepreneurs and business owners across Vermont. We'll meet a dairy farmer, a bar owner, a dentist and the owner of an executive search firm.

One in five Vermonters is considered elderly. But what does being elderly even mean — and what do Vermonters need to know as they age? I’m looking into how aging in Vermont impacts living essentials such as jobs, health care and housing. And also how aging impacts the stuff of life: marriage, loss, dating and sex.
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