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Greg Bobolo has engineered major deals that have made SendtoNews one of the major players in packaging and marketing sports highlights for the media.Chad Hipolito/The Globe and Mail

In August, Greg Bobolo was sitting around a table in Aspen, Colo., drinking beer and eating up stories about big sports stars and big sports deals. Sharing the pizza were heavy hitters such as former baseball player Tony La Russa, manager of three World Series-winning teams, and Jerry Colangelo, chairman of USA Basketball and former NBA coach.

Mr. Bobolo, 37, is chief executive officer of SendtoNews, the Victoria-based company that has been transforming how sports video is consumed by image-hungry fans around the world.

The public face and deal-maker for SendtoNews, Mr. Bobolo was attending the annual Global Sports Summit to make contacts at the three-day meeting for bosses of major sports franchises. "No cellphones, no tweeting, no media allowed," Mr. Bobolo said of the private gathering. Ironically, his life is based on technology; he travels with six batteries for his two iPhones.

Such high-level networking is a way of life for Mr. Bobolo, who joined SendtoNews in May of 2011. Since then he has been behind major deals, including contracts this year with the NFL and NASCAR, one of the most-viewed sports in North America. And he's predicting more of the same. "It's going to get very interesting over the next nine to 15 months because there's a lot of very big deals that are coming down the pipe."

SendtoNews was launched in January of 2010 by television reporter Keith Wells. The company had developed a platform that allowed non-accredited media to relay video from the 2010 Olympics to their local stations.

Today, SendtoNews and its 25 employees operate by spending millions of dollars to buy rights to professional sports highlights which are then distributed at no charge to more than 1,000 newsrooms in North America, including The Globe and Mail.

The venture-backed company, of which Mr. Bobolo is one of several shareholders, makes its money via the ads attached to each video. Ad revenue from the video is distributed between the rights holder, media outlets and SendtoNews.

The arrangement is a renaissance for media. "We're part of a bigger-picture solution. Newspapers know that a big part of their future is in video or online," he said.

When he attended the International News Media Association congress in 2012 in Los Angeles, Mr. Bobolo got a jolt. "Not a single publisher in the world had a video strategy, including USA Today. It was really shocking," he said. At the 2013 INMA event in New York, everybody had a game plan, he said.

According to Cisco Systems, roughly 85 per cent of all Internet traffic will be video by 2017, and a healthy proportion of that will be sports video.

At SendtoNews, growth has been significant since Mr. Bobolo's arrival. "We have a digital network that sees millions and millions of viewers every month, and it's growing steadily at about 100 per cent month-over-month," he says. By the end of 2013, SendtoNews will be the largest provider of short-form sports video content in Canada. And by the end of 2014, Mr. Bobolo is predicting more than 100 million monthly viewers in North America.

He doesn't expect audience numbers to stall. "We believe there's a huge audience in the digital landscape. Everyone who didn't see the race, or wants to see the race, is either watching it on their mobile phone or desktop computer and wants to see the highlights."

Aware that viewers hate to watch ads before a clip, Mr. Bobolo and his team are working with agencies to place ads in the middle of it or on a split screen, known as "deep-stream" advertising.

Fast growth is necessary because there's nothing proprietary about the technology used to upload and distribute the content.

"The technology won't be what allows them to be a success in the long run," said Brock Smith, head of entrepreneurship at the University of Victoria's Gustavson School of Business. "Anybody can do this, but SendtoNews has had a head start. What's interesting are the relationships that have been developed."

Long-term success thus comes down to the human element, Dr. Smith said. "It's a people thing, a matter of trust."

Dan Gunn agrees. He's the executive director of the Victoria Advanced Technology Council, or VIATeC, an umbrella group for the city's burgeoning technology industries. "SendtoNews had first-mover advantage, important when you're claiming the territory but you have to build relationships. Technology alone is seldom the secret sauce."

Mr. Bobolo knocked on a lot of doors in his quest to broker deals to sustain the fledgling company. "I've met with over 120 sports owners, from the NHL to the NBA," he said. "I love to go directly to the top."

Mr. Gunn noted, "A lot of people would be afraid to walk into a room of big owners, but Greg has that earnest confidence. He works harder than anyone else but has a large smile on his face."

As someone who never attended university, Mr. Bobolo does his homework. "It's quite interesting doing work with everyone from the NBA, the NHL, NFL. These are all Ivy League graduates that we're sitting with in the boardroom doing the negotiations. It's a great test. I love it. I'm not intimidated.

"I always try to learn and know more than everybody else in the room because I just feel I have to," he said.

And as the son of a mom who owned a travel school and a dad who owned an advertising agency, he credits entrepreneurship genes for some of his success. "Every day after school, I went to their offices. It was sort of a way of life for me."

Not one to drop the ball, Mr. Bobolo keeps an eye on SendtoNews's biggest challenger, London-based Perform Group PLC. "You're always worried about competition, but again, you always have to be doing homework, looking to see who's doing what. But remember, there's only so many sports teams, so there can be only so many players.

"Our goal is to have all content carved out exclusively so nobody else can get it, or if anybody wants it, you would have to come see us to get it," he said.

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