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24/7 executives

Greg Bobolo, CEO of SendtoNews, never travels without his running shoes. Which means they’re always with him, because he flies about 225,000 miles a year.Chad Hipolito/The Globe and Mail

24/7 Executives is a series of stories on high-performing professionals who are as serious at play as they are in the conference room. See the other stories here.

Before Greg Bobolo completed his first Running of the Bulls in Pamplona, Spain, he devoured information about the 500-year-old event.

"I wanted to know the traditional way. Why it was a rite of passage. Why you wear a sash," said Mr. Bobolo, chief executive officer of SendtoNews, the Victoria-based company that buys rights to sports content and distributes it to media outlets. "It's similar to how I do business. I do huge research. It comes down to really knowing your stuff."

Wearing the traditional white shirt and pants, red neckerchief and sash, he was the only one of his several friends who risked death by stampeding alongside bulls about 15 years ago. "It was terrifying. Everyone I knew chickened out," said Mr. Bobolo, 39. Three years later, he repeated the few minutes of testosterone-infused street panic.

Being fearless and fully-primed are how Mr. Bobolo, who was not injured in either sprint, approaches work and play.

"You have to be prepared for the unexpected and be able to form a new plan or new strategy," said Mr. Bobolo. "You can't steal second base without leaving first."

Art Aylesworth, a well-known Victoria entrepreneur, has been chairman of SendtoNews since 2009. In 2011, he recruited Mr. Bobolo, who was then the sales and marketing boss at Seeker Solutions, an information technology company.

Mr. Aylesworth, 62, saw in Mr. Bobolo, a trait they share. "He's really hard to kill," said Mr. Aylesworth, referring to the tenacity, competitiveness and fierce drive embodied by Mr. Bobolo, a 2006 finalist for Ernst & Young's entrepreneur of the year award.

"He's also an incredibly hard worker, a 24/7 guy who never turns off," Mr. Aylesworth said. "When something doesn't go his way, he realigns his attack and goes back and approaches it from a new angle. He's always on the offence."

Conscious that he didn't "go to the right schools," the Langara College marketing graduate who launched his first business, Bobolo Publications at 22, in Vancouver, admits he's had to be intrepid. "When I started, I was punching way above my weight class," he said.

And as Mr. Aylesworth notes, a voracious appetite for learning exists. "He takes information from others and shapes it into his strategies. Most type-As think they know everything. Not Greg."

As for Mr. Bobolo's "gaps," other SendtoNews staff fill them in, Mr. Aylesworth said. Mr. Bobolo's role is to be the face of SendtoNews, the "classic business development guy."

For example, Mr. Bobolo was at the Global Sports Summit in Aspen, Colo., a few years ago and spotted former professional baseball manager Tony La Russa. He grabbed the opportunity to gather some intel.

"I wanted to know what it was like to lead three World Series championship teams, what's the difference between winning and losing, because I run a business that works with professional sports and we all build teams," he said.

Mr. La Russa, voted baseball's manager of the year four times, had two tips for success.

First, the one-ass rule. His teams had only one problem player. Once there's more than one, it becomes an unmanageable team.

Second, become a family. Stick together and respect one another.

Since joining SendtoNews, Mr. Bobolo has had to fire four people, dismissals that came quickly to keep the family happy, But, he adds, "I want everyone to fail. If you're not failing, you're not trying. But, don't fail more than once," he warned.

After Mr. Bobolo joined the family four years ago, SendtoNews experienced bullish growth. The company, with 36 employees at offices in Victoria, New York, San Francisco and London, distributes game highlights, player interviews and other sports content from roughly 75 sports leagues on four continents. Content is syndicated to more than 1,000 television, radio, print and online news outlets. The company makes money from advertisements that accompany the sports bites.

In 2013, SendtoNews's content generated 28-million views in North America. In 2014, that ballooned to 430-million views. Mr. Bobolo predicts the content will reach 1.2-billion views in 2015.

And this month a financing deal worth up to $20-million, from primarily European and U.S. investors, should be complete. The money will be used to expand SendtoNews's New York operations and hire several more executives to further the company's global expansion.

Fond of international sports gatherings, Mr. Bobolo was at the Laureus World Sports Awards in Rio de Janeiro, Brazil, in 2013 when he rubbed knuckles with athletes such professional boxer (and current Kiev major) Vitali Klitschko – "I couldn't imagine being hit by him" – Marvin Hagler, Magic Johnson, Martina Navratilova and Boris Becker. I want to know firsthand about these people. When you can sit across the table from them, it normalizes them. We put them on pedestals, but they're incredibly real, down-to-earth," Mr. Bobolo said.

Eva Longoria, whom Mr. Bobolo had a crush on, also happened to be floating around. The boy from Canada was promised a dance with the actress at the event's gala, but he spotted a sought-after contact. "I had to make a decision. I went for the long-term business relationship."

Mr. Bobolo admits that deal-making for SendtoNews is done among stars of various stripes. Not long ago he was on a mega-yacht in Monaco with NASCAR executives and advertising bigwigs. At 3:30 a.m., after several hours of carefully-nursed drinks, he had a casual but orchestrated meeting with an executive. "This is when you get the real deals," he said.

As the guy who has to seek and then seal the deals, much of Mr. Bobolo's time is spent travelling. "I've been in every major-league office," he said. In 2014, he flew 225,000 miles, about 19,000 miles a month, taking red-eye flights so he doesn't waste the workday. "Getting enough sleep is a problem, but with my sleep mask, I'm out in three minutes," he said.

While he spends almost as much time in New York, Mr. Bobolo uses Victoria, where his 13-year-old daughter Haley goes to school, as his fixed address. In New York, it's routine for him to do quick runs in Central Park before marathon business sessions. "Running helps me to add clarity, to focus, going into meetings," said the former youth hockey and soccer player who never travels without his running shoes. "I ran up a mountain a while ago. It was really fun."

A surfer since the age of 10, Mr. Bobolo has also tested the waters around the world. In April he had a four-day break in Maui, Hawaii. "I golfed, surfed, did some beach running, mountain-climbed. It was awesome."

Charmaine Crooks, a five-time Canadian Olympian and winner of a silver medal in 1984 for the 4x400-metre relay, has known Mr. Bobolo for three years. "He's got the high-performance attitude all the time, mentally and physically, on the business side and his lifestyle," said Ms. Crooks, 53, president of NGU Consultants.

His ability to excel at activities such as scuba diving, skiing and surfing give Mr. Bobolo the skills to handle delicate meetings or constant travel, she said from Vancouver. "Greg has the energy to navigate through a growing schedule. For him, it's all about delivering. Anyone who can take this Victoria-born company onto a global level is to be applauded."

His method? "I like to work from the top down, to eat the cherry first," Mr. Bobolo said.