Leiweke admits he doesn't look out the window much anyway. "I'm a little bit more interested in staring at the people I'm meeting with - and trying to scare the crap out of them," he says. The easy laugh that follows makes it clear he's joking - to a point.
Leiweke is very serious about empire-building. The former president/CEO of Anschutz Entertainment Group, Leiweke was the architect behind the AEG model of combining club-to-stadium real estate with content in sports teams and live events, along with businesses such as ticketing, media deals, merchandising and sponsorships.
At MLSE, which he joined in June 2013, Leiweke oversees one of the world's premier sports-and-entertainment companies. MLSE owns the Toronto Maple Leafs (NHL), the Toronto Raptors (NBA), the Toronto Marlies (AHL), the Toronto FC (MLS), Air Canada Centre and its adjacent $500 million Maple Leaf Square district. The company also is invested in, operates and manages events at Toronto's Ricoh Coliseum and BMO Field.
Leiweke believes that much of MLSE's growth will come through sports, including a $120 million renovation of BMO Field and the growth of the Raptors, the NBA's only presence in Canada.
These days, though, Leiweke is zeroing in on boosting MLSE's music profile, in part through an expanded partnership with Live Nation, already the dominant venue player in Toronto.
"With his experience and desire, I think the sky's the limit, just based on what his partners want to do," says Jon Bon Jovi, whose band had Boxscore's biggest-grossing tour in three of the past five years, all promoted by AEG.
Live Nation first partnered with MLSE in 2011, and on Leiweke's watch the deal was renewed last November, through 2018.
The world's largest promoter, Live Nation owns and operates Molson Canadian Amphitheatre in Toronto and operates the city's TD Echo Beach at Ontario Place. As part of the alliance, MLSE sells and services Live Nation's sponsorships for its properties.
In what the former AEG executive calls a "great transformation," Leiweke has gone from competing fiercely with Live Nation at AEG to partnering with the company at MLSE.
"We were tired of beating each other up," quips Leiweke of his relationship with Live Nation CEO Michael Rapino. "Mike and I agree that Toronto could be one of the largest growth markets in the world for music, and we're both dedicated to investing real money and upgrading the infrastructure to make that happen."
While MLSE and Live Nation have done business together since 2011, "through the tenacity of Tim Leiweke, we've been able to dream even bigger and do more things," says Rapino, whose hometown is Toronto.
The next MLSE-Live Nation venture could be in one of the most robust sectors of live music: festivals. "We're [developing] a vision for a new festival grounds right smack in the heart of downtown Toronto that will be one of the best festival facilities in the world," says Leiweke.
While U.S. producers continue to fill the gaps between destination festivals in the United States, Toronto is "totally untapped" in that regard, says Leiweke.
He adds that the proposed festival venture with Live Nation would take place at an as-yet-unannounced location that is "as nice a site as I've ever seen. My guess is that Live Nation will be able to lock it down in the near future, and we'll be their partner on that."
Live Nation already produces the Digital Dreams EDM fest in Toronto. Rapino stops short of offering details of the new festival with MLSE, but he notes that "Toronto is a world-class city, and we're looking to bring country, more EDM and a big mainstream festival for Toronto under this partnership."
Meanwhile, Toronto has quietly become one of the world's foremost music markets. "This is one of the most diverse and fastest-growing marketplaces I've ever seen," says Leiweke.
Adds Rapino: "Forget that it's my hometown. I'm proud, and it's always nice to do well, but the numbers speak for themselves. This city sells a ton of tickets."