The job ad asked, “Do you want to get high legally?”
Khary Penebaker decided he did, and from that point on, his career path differed dramatically from those of his fellow college students at the University of Wisconsin-Milwaukee.
It was 1996, he was at UWM on a track scholarship and he had just taken a job with a roofing company.
“It was my first real kind of job,” said Penebaker, now the president of Milwaukee-based Roofed Right America. “I stuck with it and fell in love with it.”
Taking a job while in college isn’t unusual; owning a roofing company is. But by the end of his first year with the company, Penebaker was a part owner after the previous owners split the company into thirds and he bought one of them. He was an entrepreneur at the age of 19.
He took it a step further in 2001 after he graduated from college. The company he was running was geared toward residential roofing, and he preferred commercial, he said. So he broke away with his company, retaining the name The Penebaker Enterprises.
He ran it from 2002 to 2011, when he was forced to close. He said the economic downturn caught up to his company, and he couldn’t stay in front of his financial obligations.
Still, he said, the failure offered valuable lessons.
As a young minority contractor working with well-known contractors, Penebaker said, he approached it with a “don’t rock the boat” mentality, particularly when it came to collecting on bills.
“When the issues were there,” he said, “I failed to ask for help.”
He said he tried to get out of the industry after that, working for a sheet metal manufacturer for a couple years. But in 2014, Roofed Right approached, looking for someone who had succeeded, failed and learned from both experiences.
“When I got to meet the owners of Roofed Right,” Penebaker said, “that’s when I realized the mistake that I made with my company was I didn’t have anybody to help me at the executive level.”
He said he sees similarities between where Roofed Right is headed and where he wanted his company to go. But there’s a stronger foundation now, he said. Roofed Right, for instance, has 165 employees, he said, while Penebaker Enterprises had 50.
And no matter what roofing company he’s with, Penebaker has a healthy respect for the difficulties of the job and the people who do it.
“Roofers risk their lives every minute they are on the roof,” Penebaker said, “and yet we are disregarded as people who couldn’t do anything else.”
Since joining Roofed Right, Penebaker also has tried his hand at politics. He ran as a Democrat in 2016 in the heavily Republican 5th Congressional District against incumbent U.S. Rep. Jim Sensenbrenner, R-Menomonee Falls. Penebaker lost the election but said it was a great learning experience.
“Unless you’ve been on that side of the table in politics, you have no idea,” he said. “You see how the sausage is made, and it’s not a pretty sight at all.”
He might have fallen short in politics, but, he said, he’s happy with the choices he’s made.
“It’s not every day,” Penebaker said, “you get to work at a place where you enjoy being and with people you enjoy working with.”
The Daily Reporter: What surprises you most about your work?
Penebaker: I am often surprised at how important roofing is but how little importance some in our society place on it. I appreciate how there aren’t many people who grow up saying, ‘I want to be a roofer when I grow up,’ but there are a good number of us throughout the country and in Wisconsin. None of the beautiful Wisconsin buildings that make up our city’s landscape would be able to function without a great roof on them.
TDR: Which living person do you most admire?
Penebaker: Barack Obama
TDR: What other job did you consider trying?
Penebaker: I have been in the roofing industry for 20 years now. At a few points along the way I considered other industries, but nothing really compares to being able to put a roof on and taking pride in knowing that we are responsible for protecting that entire building.
TDR: What is your greatest fear?
Penebaker: The fear of not trying … and clowns.
TDR: What is your greatest extravagance?
Penebaker: I don’t have many, if any, extravagances in my life. A while back I did. I owned a brand-new Mercedes, and it made me feel that I had ‘made it.’ Unfortunately, I lost that car when my company closed six years ago. But I learned a lot from that entire experience.
TDR: What would you never wear?
Penebaker: A gun
TDR: If you could change one thing about yourself, what would it be?
Penebaker: I would get rid of my apparently incessant desire to take everything personally. I really need to stop that one. But to me, it is never ‘just business.’ It is always something personal involved in decision-making. Still, I have to stop allowing myself to take everything so personally.
TDR: What would your colleagues be surprised to find out about you?
Penebaker: I’m sure my colleagues, as well as others, would be surprised at how often I cry.