CEO Ride 2

ROAM WITH A VIEW - The view from a motorcycle as riders head out.

CASPER -- If you happened upon a pack of bikers roaring north out of Cheyenne last month, you might have thought you’d found a cadre of confused of Coloradoans getting a two-week jump on landing a prime spot at the 77th Annual Sturgis Motorcycle Rally, which officially gets rolling in the Black Hills on Aug.4.  

However, while these riders did end up taking in the famous sites the northeast part of the state — and neighboring South Dakota — has to offer, they primarily there to learn how to be better leaders and corporate stewards.

The riders are participating in an innovative program that brings together chief executive officers from around the world for a series of conferences and peer-based networking opportunities woven into some of the nation’s iconic motorcycle rides. Now in their fifth full year, these “CEO Rides” are put on by Orlando, Fla.-based WaterMark International CEO and author Dwain DeVille, (author of ”The Biker’s Guide to Business,” 2009), who organizes these training adventures for business leaders from all backgrounds who also share a passion for riding.


The CEOs made the historic hamlet of Deadwood their home base for the ride and traveled famous byways like the Needles Highway, Iron Mountain Road and Spearfish Canyon on their way to destinations like Custer State Park, the Crazy Horse Memorial, the Badlands and Devil’s Tower.

“This was the first time the CEO Ride has been in Sturgis and the Black Hills,” said DeVille, who had just returned to Deadwood from an afternoon ride to Mount Rushmore National Monument., “We came two weeks before the main event so we could stay away from the crowds and craziness.” Past rides have taken CEOs through the Smokey Mountains of North Carolina and down the Vegas Strip. And a ride through the historic streets of New Orleans is scheduled for this fall.

DeVille said he has gone on rides through Wyoming before — he bought his boots in the state while passing through a couple of years ago — and he would like to bring more of the rides, which he bills as “a full-throttle business experience” here in the future. His current bike of choice is a big touring motorcycle, a Honda Gold Wing, which Deville said he switched to after riding Harley’s for more than a decade in order to “get back to his roots.”

Those roots include 35 years at WaterMark, where he helped companies navigate their way through the current business climate. “I help them figure out where they want to go and how to get there,” DeVille said. He explained that he had the brainstorm to organize his very first CEO ride back in 2004 after surviving a brush with kidney cancer left him with the desire to combine his “two great passions: business and biking.”

DeVille said at first he worked with outdoor vehicle manufacturer Polaris on early versions of the concept, before refining it into the program’s current form, which he said is best expressed by the CEO Rides slogan, “We’d rather ride our motorcycles thinking about business than sit in a conference room thinking about our motorcycles.”

For the Sturgis ride, seven CEOs participated including the head of a Canadian tech company, another Canadian who runs a large professional staffing firm and the CEO of an Irish tech business.

“We try to keep it intimate. The peer group process works best that way,” DeVille said. “The CEOs get to know each other better and they learn to share and care about people who can best understand what life is like for them. They can talk about things with each other that they could never talk about with anyone at their own companies.”

DeVille said the riders spend their mornings “digging into businesses” in a fairly standard setting — a hotel or resort conference room will usually do nicely — which they follow up with a ride in the afternoon and then dinner and more-casual business-oriented conversations in the evening.

“With everything, it’s usually a week-long immersive process with a main focus on business. But the rides break things up and gives people a chance to think about what we have been discussing. And that doesn’t stop after the ride is over.”

Incorporated in Wyo.

One of the CEOs taking part in the Sturgis ride was Stuart Bostock, whose company, The Security Centre, is a security and defense specialist based out of the Cayman Islands that had its beginning with incorporation in Wyoming under the state’s business-friendly structure for startups.

Bostock said he first became familiar with DeVille through “The Bikers Guide to Business” and that attending the CEO rides (Sturgis was his third) was a natural progression for him since he “finds riding the escape of my life.”

Bostock said The Security Centre (which does everything from manufacture and market blast-proof window blinds and high-tech security cameras and drones to provide uniformed security services and K-9 units) has been expanding steadily across the Caribbean in the past few years and has recently opened a southeast U.S. regional office in Chattanooga, Tenn. He said Wyoming’s pro-business environment and tax structure had it under preliminary consideration for a future “boots on the ground” base of operations for a possible expansion into the western U.S. market.

“We spent a lot of years researching the U.S. market and the non-U.S. security market and we don’t want to force anything,” he said.

“But eventually we will want to establish a foot print in the west so that we cover all of our markets,” Bostock said. “Coming from the Caribbean and entering such a large and advanced market as the U.S., so far, things have gone extremely well.”

Bostock said he wasn’t completely sure what to expect when he attended his first CEO Ride, but that he quickly saw the value in connecting with “like-minded” individuals, both on and off their bikes.

“I’ve met people completely different than what I would have imagined them to be,” Bostock said. “Now I see old faces, who have become trusted mentors and advisers. And good friends.

“You get a nice cross section of CEOs from large and small companies and you can learn as much from the little guy who had a nice increase in sales volume as from the head of a giant corporation.”

Bostock said the “safe environment” of being with one’s peers and the “shared experiences we have out of the board room” while riding were “head clearing.”

“You have so many epiphanies,” he said.


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