Randy Kuhn is best known for installing superior low-slope and steep-slope roofing systems in the Chicagoland area since 1978, but a passion for sailing the Great Lakes is also evident, as Kuhn has finished first in his class in the Chicago to Mackinac race on three separate occasions.

Randy Kuhn is best known for installing superior low-slope and steep-slope roofing systems in the Chicagoland area since 1978, but a passion for sailing the Great Lakes is also evident, as Kuhn has finished first in his class in the Chicago to Mackinac race on three separate occasions.

Kuhn, owner of Windward Roofing in Chicago, started his roofing business nearly three decades ago. "We do low slope, steep slope, sheet metal, masonry - we really do it all on the roofing end," he says. "We’ve done well, between $8 million and $10 million in sales. We’re profitable each year, as you need to be to survive."

Sailing Came First

"I started sailing with my dad when I was three or four years old. He got me involved," Kuhn says. "I started racing competitively in college - actually had a football scholarship, but chose sailing."

It was sailing that first put Kuhn on the path to becoming a roofing contractor. "I started the roofing company based on my passion for sailing," Kuhn says. "The reason I started the company, I thought at the time, was all the people in sailing were wealthy. I thought this was a good segue into working opportunities through sailing."

From the beginning, Kuhn has merged roofing and sailing. "I’m at Windward roofing - that’s where I got the name," he says. "I’ve been sailing longer than roofing."

Kuhn started sailing on Lake Michigan, learning how to cross the giant freshwater lake. He eventually took on worldwide sailing adventures, including sailing the Pacific Ocean in 1982, traveling from the Panama Canal to the Galapagos Islands to Tahiti.

"That trip took place with only a crew of six or seven guys in the middle of winter - a good time to go sailing on the Pacific," Kuhn says. "I started racing competitively. And once you start to get good, you start sailing in other competitions."

Kuhn has taken part in sailboat races like the Rolex Cup and Chicago-based regattas on weekends, and that’s when he admits he becomes "more serious."

"In 1998, I bought my own boat, a CNC 40 (from a Canadian yacht maker)," Kuhn says. "It’s a 40-foot sloop that was built as a race boat."

Chicago to Mackinac

With a $70,000 sailboat in tow, racing took on a new meaning for Kuhn in 1999 when he put together a crew and entered his first 330-mile Chicago to Mackinac race. "I took some of the older guys who raced a lot with me, and the first time we raced we got second in the Chicago to Mackinac," Kuhn recalls. "We’ve won our class (Chicago to Mackinac) in 2001, 2003 and 2005."

One of Kuhn’s crew members, salesman Bryan Shaffer, is among the sailors who crew for Kuhn aboard his boat, Cheep N’ Deep. "I have eight guys who have sailed with me for some 20 years, all good sailors," he says.

Kuhn, the captain of his sloop, says the best part of sailing is getting his 40-footer to reach speeds of 13 knots, although 6 to 8 knots is the average speed. "The Port Huron to Mackinac is a faster race; I haven’t done as well in that one," Kuhn says. "You go 285 miles and go around a mark. You have two paths to choose from. The Port Huron race is nowhere near as challenging and freethinking as the Chicago to Mackinac. The lake is wide open, and you can choose any path."

Kuhn competed in the Chicago to Mackinac Race this July, finishing in the bottom third of his class. But as the saying goes, every day spent sailing is still a great day. "Sailing actually takes you away from everything else in life," he says. "I’m totally in the moment. That’s what I love about sailing: I am totally involved. Who owed what, what percentage of the job was completed - those are things you don’t worry about when you’re sailing. It’s nice to be in that position, free of thought."

Kuhn says John Cherchi, the chief financial officer for Windward Roofing, runs the office when he’s sailing. "John runs the financial part of the business, and my superintendents run the jobs when I’m gone," Kuhn says. "The boat’s still part of the job. I take customers out all the time. Most go golfing, but with my salesman, we take people out two times a week in the summer. There’s nothing like it on the water."