How Stingray’s thrill-seeking CEO took his passion public

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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.

It's not even noon on a Wednesday, and no matter how much champagne Eric Boyko drinks, his flute is never empty. Every five minutes, it seems, someone comes to refill it and cheer his success.

On the terrace of Stingray Digital Group Inc.'s office in Old Montreal, the company's chief executive officer is mingling among a hundred or so employees as Kanye West's Good Life plays. Everyone keeps turning from their drinks to look at a big-screen TV near the door – not for lack of a good time, but because of what's on: Stingray's stock price, $7.20, two hours after it was listed on the Toronto Stock Exchange.

Staff at the acquisitions-hungry digital music provider – they run those TV channels of preprogrammed playlists high up on the dial in 111 countries – are pleased as punch as the price has crept up from its listing price of $6.25 and stabilized. (Its A-shares closed the first day at $7.25, up 16 per cent.)

Mr. Boyko works the crowd, champagne flute in one hand and BlackBerry in the other, telling anyone within earshot that it is the best day of his life.

As the celebratory soundtrack shifted backward in time, to Lil Jon, soulDecision and Puff Daddy, Mr. Boyko is happily looking ahead. Stingray raised $140-million in the initial public offering, though it could rise as high as $180-million. With the new backing, Stingray's debt can be cleared, boosting its cash flow so that Mr. Boyko can continue his global conquest. Half the world's countries isn't enough.

"When we get a new deal in Bolivia, I'm excited not about the money, but that we're in Bolivia," he says, stepping a few feet away from the crowd for an interview. "We conquer countries by having music there."

Mr. Boyko, 45, likes to call himself an explorer. He travels the world to kayak, climb mountains and trek unknown terrain. His office is plastered with photos from his adventures. Rarely able to sit still, he'd rather go heli-skiing in the Andes than sit on a beach. Stingray is that attitude distilled: He'd rather be scouting the world for like-minded services to snap up than spend his days at a desk.

A serial entrepreneur, Mr. Boyko spent his 20s working six days a week for little income at one of his first startups, eFundraising.com, before selling it at the height of the dot-com boom. For the first time of his life, he was flush with cash and had time to spare, started taking adventures to make up for lost time. "I started skiing at 30," he says. "I'm a late bloomer."

He has since, he says, climbed four the world's Seven Summits, and put himself into binds from which no human should have to extract themselves.

In what he calls "one of the best experiences of his life," he says, he and a guide were dropped by helicopter onto a mountain in Chile 10 years ago, only to find out the copter couldn't pick them up from their skiing destination once the air warmed.

"I ask, 'How do we get down from here?' And the guy says, 'I don't know, dude – I hope we find a way down.'"

Stingray, on the other hand, has been an upward climb. It launched in 2007, when Mr. Boyko and partners bought the Karaoke Channel from a North Carolina company and took over the music-streaming Galaxie TV channels from CBC.

Working primarily in TV gives Stingray the appearance of a tech play, but it's really in the acquisitions game, scooping up small competitors the world over and scaling up constantly. The company boasts that it's in 110 million households worldwide. The quest for expansion, Mr. Boyko says, is "like a game of Risk." Not coincidentally, the company boardroom has a custom, Stingray-branded, wood-cut Risk board, gifted to Mr. Boyko by a staff member.

IPOs by fellow Canadian companies Shopify Inc. and Cara Operations Ltd. ignited the public appetite for Canadian non-resource companies this year. But that hype wasn't around last December, when Stingray began mulling a public offering. At the time, the company was preparing for one of its original investors, Novacap Management Inc., to wind down its 29.5-per-cent stake in the company. (Another investor, Telesystem Ltd., was also preparing to sell much of its stake.)

There was talk of a private sale, but the investment partners couldn't come to a deal on a price. Going public was a solution that worked for both parties – especially so when a share structure was reached that gave Mr. Boyko majority control of the company through multiple voting shares. "I don't want to be in a position here I have to sell the company in six months," he says. "So that was the deal."

Selling investors on the IPO was another adventure. Stingray executives had 58 one-on-one meetings with key investors across North America, travelling to cities including Boston, New York, Toronto, Winnipeg, Calgary and Vancouver, says Mathieu Peloquin, the company's senior vice-president of marketing and communications.

"The road trip was like an exploration, because it was four weeks of meeting people every day, being focused," Mr. Boyko says. "Except for this road trip, instead of losing weight, I gained weight. Now I've got to officially start working out." It's clear Mr. Boyko squeezes fun out of even the most repetitive of endeavours. "He thought it was a boys' weekend," jokes Lloyd Feldman, the company's senior vice-president and general counsel.

Now public, the company will continue what it's best at. "We're in a great position to do a lot of acquisitions," says Mr. Boyko. "We're an international player, so we're very excited about accelerating our business."

The digital-subscription music industry is rapidly maturing thanks to growing awareness of on-demand streaming services, including Spotify, Deezer, Rdio and Jay-Z's Tidal. Stingray is sometimes erroneously described as a competitor to these services, when in fact it serves an entirely different market segment.

While Spotify and its brethren sell themselves as one-stop shops for on-demand consumption of millions of songs, Stingray is geared toward more passive listeners. It employs 85 music curators worldwide to craft its playlists – for its TV channels, its mobile app, and for in-flight soundtracks with carriers such as Air Canada. Preprogrammed playlists have lower costs than on-demand services, making it comparatively cheap for Stingray to scale up. So by targeting passive instead of active music fans, it's fairly easy to expand into new markets.

"We're a mass product for the 90 per cent of people who love listening to music, but can't name four jazz artists, and want to listen to the best jazz channel," Mr. Peloquin says. Stingray's customers, in other words, trust the company to keep on top of what they should be listening to.

As Mr. Boyko dances and mingles, Mr. Feldman chats with some of Stingray employees about which playlist the crowd is listening to. The group agrees that the mix, now heavily leaning towards '90s rap, is great. It turns out it's someone's personal playlist – not Stingray's. "Someone," Mr. Feldman says, "should make a channel out of it."