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Zirtue Founder Dennis Cail’s 600-mile Ride Across Italy

A 600-mile bike ride across Italy showed fintech co-founder Dennis Cail that leadership is not just for frontrunners.
| |Photography courtesy of Dennis Cail
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Epic Views: Dennis Cail was inspired by the country’s scenery during his bike trek across Italy.

By the fifth day of pedaling across the high-heel of Italy’s boot-shaped landscape, Dennis Cail had convinced himself he could finish the 600-mile cycling tour that his buddies had talked him into. “It’s this battle between your mind and your body, and the first few days, those things are very much in conflict,” the co-founder and CEO of Dallas-based fintech Zirtue says.

Over 10 days, the group scaled several mountains, some at a 25 percent incline, ranging from 60 to 70 miles a day. Cail often brought up the rear, trailing his avid cyclist cronies, but the solitude gave him time to reflect. “I learned that to lead something, you don’t always have to be at the front,” he says. “There are so many things you can make contributions in just by being your best and strongest self, and I learned that everyone’s not going to always get to the same place at the same time, but if you’re going in the same direction and to the same place, that’s OK, too. I think about Zirtue; we need people to hang back and work on the backlog of things we have going with a product. Not everyone can be working on the latest and greatest features, and that should be OK,” Cail says.

Cail says his friends often raced to see who could reach the town at the end of each day’s trek first. He tried to keep up initially, but soon realized that took away the joy of the journey. Instead, he learned to pace himself, reaching each milestone on his own time. He hyped himself up with hip hop music during much of the ride, reflecting back on life memories and lessons as he rode. “It’s a big mental deal. It’s more mental than physical,” he says.

While on the bike, he also learned to focus by enjoying the scenery along the journey. “I think we all need to find new energy,” he says. “What is that one thing that you are just oblivious to or not paying attention to? Somehow, some way, if you stopped, you’d say to yourself  ‘I like this. I want to see more.’ The work still must be done—I still have to go 60 miles—but at least I’m in the right head space to do that now.”

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Kelsey Vanderschoot

Kelsey Vanderschoot

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Kelsey J. Vanderschoot came to Dallas by way of Napa, Los Angeles, and Madrid, Spain. A former teacher, she joined…
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