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Jordan Gnat, CEO of Playmaker, at his home in Toronto on July 19, 2021.

Jessica Lee/The Globe and Mail

Jordan Gnat will freely admit his foreign-language skills aren’t his best calling card.

“As my kids say, my Sesame Street Spanish isn’t going to be very helpful,” said Mr. Gnat, 49, in an interview. And how is his Portuguese? “Obrigado,” he responds with a self-effacing laugh. “That’s about as good as I get.”

Over the past few months, though, Mr. Gnat has planted a series of flags in the Latin American digital sports media space, bringing a growing collection of websites, social media accounts and other online properties under the purview of Playmaker Capital , the Toronto-based startup he joined as CEO last December.

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Strictly speaking, as Mr. Gnat will tell you, Playmaker isn’t a startup so much as a roll-up: It went public in early June on the TSX Venture Exchange through a reverse takeover of Apolo III Acquisition Corp., a capital pool company co-founded by Vincent Gasparro, who recently served as principal secretary to Toronto Mayor John Tory.

In April, Playmaker had already acquired Futbol Sites, a Miami-based operator of more than 10 soccer-focused websites, branded under the name BolaVIP, targeting fans in Brazil, Argentina, Chile, Colombia, Mexico, Peru, Ecuador, Central America and the United States. Citing Comscore rankings, the company announced that BolaVIP Brazil was the highest-ranking sports website in that country in May, with more than 15.4 million unique visitors.

A couple of weeks after its TSX-V debut, Playmaker added Fanáticos Por Futebol: Facebook and Instagram fan pages with a total of almost 4.5 million followers.

And last Tuesday, it made its first major English-language move, buying Yardbarker, a Silicon Valley-based site that aggregates thousands of pieces of sports and entertainment content for an estimated four million unique users per month, and publishes a morning newsletter sent to more than 350,000 subscribers. A news release announcing the transaction pegged the value of the deal at up to US$24-million.

If digital media strikes some investors as a gamble – the number of properties seemingly infinite yet growing every day, the rates for display ads often correspondingly tiny – they would be getting the right idea: Betting is a big part of Playmaker’s strategy.

Online sports betting, that is. Mr. Gnat believes the company is well positioned to take advantage of that industry’s growth, which is expected to be explosive as governments across the Americas legalize and regulate it, by becoming an affiliate-marketing partner of sites trying to reel in new bettors.

Affiliate marketing is one of the Internet’s more lucrative practices – certainly far more lucrative than display advertising. If a reader is on a music site or other kind of digital property (newsletter, social media account, etc.) and they click on a link to buy a concert ticket or artist merchandise, the site gets a share of that revenue.

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“I want to be in the fan monetization business,” Mr. Gnat said. “Playmaker is really a business that is being set up to live at the intersection of sports, gambling, media and technology. And we’re rolling up digital sports media assets, finding assets that we can put together, that we can leverage synergies between them, to be able to build an ecosystem of highly engaged and loyal sports fans that we can deliver to sports betting companies, teams, leagues and Fortune 500 advertisers.”

“The regulated sports betting market on this side of the Atlantic is in the top of the second inning,” said Mr. Gnat. “The appetite for growth is humongous. So the need to continue to feed the beast [with new bettors] is going to be there for quite a while.”

Affiliate marketing for online sportsbooks is big business. The Bettor Collective, which Mr. Gnat cited as an aspiration for Playmaker, is a global affiliate giant worth more than US$11-billion. But he and others insist there is room for more players.

“I think that, tactically, Jordan understands where the competition currently exists, currently focuses and currently dominates, and he understands where there’s opportunity,” said Nic Sulsky, a daily fantasy sports veteran who was recently named chief commercial officer for the Canadian division of the online sportsbook Pointsbet. “So, I think that the Latin American focus, and the Spanish-language focus, provides a really great launching-off point to build into the U.S. and Canada.”

So far, investors have been underwhelmed: Playmaker shares were off about 30 per cent at the end of the week from their debut price of 53 cents a share.

Mr. Gnat says he is on the prowl for properties “from the top of Canada to the bottom of Argentina,” the same territory he trod in his last job, as the group senior vice-president for The Stars Group. Beginning in July, 2018, he headed up corporate and business development for the Americas with that Toronto-based online gaming company probably best known as the operator of PokerStars.

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He has spent more than 15 years in the gaming industry, including stints as president and CEO of the bingo hall operator Boardwalk Gaming; more than seven years with Scientific Games, which provides casinos with products such as slot machines and gambling terminals; and CEO of Casino and Gaming Television (a.k.a. CGTV), which was owned in part by his father-in-law, Larry Tanenbaum, the chairman and part-owner of Maple Leaf Sports and Entertainment.

Another notable scion in Playmaker’s executive ranks: Its chief operating officer is Jake Cassaday, the 33-year-old son of John Cassaday, who formerly served as president and CEO of Corus Entertainment and, before that, of CTV Television Network Ltd.

Playmaker also has a well-connected group of backers and board members. It was created under the auspices of Relay Ventures, the Toronto-based venture capital firm whose co-founder and managing partner, John Albright, took a seat on the Playmaker board. Mr. Albright is also on the board of theScore, the Toronto-based digital sports media company that launched a sports betting operation in the U.S. in 2019 and is currently waiting to do the same, now that single-event sports betting has been legalized in Canada, in whichever provinces create a regulatory regime for the activity.

The Playmaker board is chaired by Maryann Turcke, the former Bell Media president, who most recently spent two and a half years as chief operating officer of the National Football League. “I think there’s value in aggregating eyeballs,” Ms. Turcke said in an interview. “It’s also just bringing eyeballs together and then serving those eyeballs up to adjacent spaces, whether it’s gaming or sports betting. We aren’t a betting company, but lots of betting companies are going to want our eyeballs, because it’s people that are hip deep in sport, they are superfans, and those are the kind of people that you can migrate into gaming and betting, and those spaces.”

“I’ve known Jordan for years, through my time at Bell Media, and then when I was at the league and he was at Stars, our paths sort of just kept crossing,” she added. When Mr. Gnat asked her to join the board, “I thought, ‘Jordan’s the real deal, he’s an authentic leader. John [Albright] is the real deal. Sure, let’s give this a go.’”

And so, as Mr. Gnat seeks out more deals, he insists the language barriers aren’t as significant as one might think: You work with local firms you can trust, and you get a good translator. You become adept at reading body language.

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And there’s one other key he says he learned from a mentor, who taught him how to manage in international settings. “You need to bother,” he said. “You need to bother to understand the basics: How do you say hello? What are the proper colloquials? Do you shake someone’s hand, do you not shake someone’s hand? In some cultures, do you bow, do you not bow? Those are things that are really important. Because the audience on the other side is watching, to see if you have bothered.”

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