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Toronto Raptors forward Kawhi Leonard (2) passes the ball during practice for the NBA Finals in Toronto, on May 29, 2019. The Raptors’ first Finals run is against a team that has won three of the past four NBA championships.Dan Hamilton/USA TODAY Sports via Reuters

Toronto’s tech community is used to battling with Bay Area talent. With the Toronto Raptors in the NBA Finals, it’s no longer fighting that battle alone – and it’s putting money on a win.

On Thursday, advocacy groups TechTO and sf.citi announced the #TechBet – a friendly charity wager on the Raps’ historic series against the reigning champion Golden State Warriors. Each has pledged an initial $10,000 for the bet, challenging the Toronto and Silicon Valley tech sectors to grow the pot as high as $100,000 a city.

The groups are hardly shying away from the obvious metaphor. The scrappy Raptors’ first Finals run is against a team that has won three of the past four NBA championships – a situation that’s fully emblematic of Toronto’s continuing emergence as a beacon for tech talent and investment, in a sector that regularly loses talent and capital to Silicon Valley giants.

But the groups are betting on their homes rather than themselves. A Warriors win would hand the pot to Circle the Schools, which helps prepare San Francisco students for their careers and life with the help of tech companies. A Raptors win would see the pledged money go to Canada Learning Code, which provides skills training for underrepresented groups of Canadians including women, Indigenous youth and people with disabilities.

Tobi Lutke, Shopify’s founder and chief executive, offered $10,000 for the cause Thursday. Andrew D’Souza and Michele Romanow, co-founders of Canadian lending startup Clearbanc, are pledging $5,000 to support the bet. “The entire Clearbanc team have been Raptors fans a long time," Mr. D’Souza said. "We moved our company from San Francisco to Toronto because we felt this is the best ecosystem to build the company.

“It’s poetic and fitting we’re passing the torch from a technology perspective from the Bay Area to Toronto,” Mr. D’Souza continued. "… But we’re also passing it from the Warriors to the Raptors. They’ve had a great run, built a dynasty, but now it’s time for the next generation to take over. It mirrors what is happening with technology.”

The bet was born late Monday, when the TechTO team contacted sf.citi with the idea. The groups had gotten to know each other over the past few months after sf.citi organized a conference of peer organizations that bridge technology with their home cities.

“We reached out to say, ‘Hey, we have an opportunity,'" said Alex Norman, TechTO’s co-founder. “Raptors versus Golden State is a great opportunity to support our local teams, but also to use tech for good and make our ecosystems rally behind our teams – and have a friendly wager which benefits the wider cities that we operate in.”

The details came together in just 36 hours over texts, tweets and e-mails. “They were really quick on it,” said Jennifer Stojkovic, sf.citi’s executive director. “Here in San Francisco, we’re used to the Warriors making the Finals – but they’re getting really creative in Toronto.”

Ms. Stojkovic is a native Torontonian who insists she is “agnostic” on the result of the series. But she’s as proud of how Toronto has grown since she left eight years ago as she is aware of the metaphor underlying the bet. “The symbolism is so staunch, eh?” she said with a laugh. “It’s incredibly impressive what we’ve been seeing coming out of Toronto."

Ron Conway, chair of sf.citi and an early investor in major firms such as Google, Facebook and Twitter, pledged the first $10,000 for a Warriors win. Mr. Norman and fellow TechTO co-founder Jason Goldlist pledged the first $10,000 for Toronto.

One question might linger for those hoping to participate in the bet – which kind of dollar are they trying to raise 200,000 of?

Turns out it depends where you live: the Canadians are raising Canadian dollars, and the Americans are raising U.S. dollars. “Golden State is considered the favourites – not that I believe that,” Mr. Norman says. “But we look at the exchange rate giving us some leverage for our bet.”

With a report from Sean Silcoff.

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