Hey! Can I paint a big white dot on your roof?

That’s the question Stephanie Avery will be asking Torontonians as she embarks on a decidedly awesome art adventure.

The 30-year-old artist is behind “Connect the T-Dots,” a project that will turn aerial and satellite views of Toronto into a giant number puzzle.

“I think at first people might think it’s a bit of a joke,” she says. “But once they see how much fun it will be, hopefully they’ll be offering up their rooftops.”

Avery, the first-ever Toronto Awesome Foundation grant winner, was handed a paper bag stuffed with $1,000 in cash on Thursday night at the organization’s launch party.

The Awesome Foundation — a concept that began in Boston and has since expanded to 13 chapters around the world — gives out monthly no-strings-attached cash grants to people with great ideas.

Avery’s pitch beat out more than 250 wild ideas submitted by hopefuls across the GTA.

Her rooftop dots will be white, numbered and three to four metres in diameter. When connected, they will form various shapes unique to each city neighbourhood. In Cabbagetown, for example, the dots could form the shape of a cabbage. Avery plans to solicit shape suggestions from community members.

The Awesome Foundation grant, she says, will pay for the first neighbourhood connect-the-dots puzzle, including the cost of renting a helicopter for aerial photos.

Avery’s biggest challenge is kind of obvious: she will have to convince business and homeowners to let her make a mark on their roofs.

Her strategy is simple. “Ask nicely. It’s worked for me in the past with other strange projects that I’ve done.”

The strangest of them all was probably a sculptural installation made entirely of human teeth and dental floss. Avery, who studied visual art at York University, approached local dentists and convinced them to hand over more than 500 pearly whites for the piece.

“It’s amazing what people will help you with if you just ask.”

Avery’s quintessentially Canadian approach is one of the reasons the Awesome Foundation chose her project.

The Trustees of Awesome also favoured it for the “huge participation possibility” in the crowd-sourcing of images and local rooftop volunteering. They also felt the project could draw global attention through Google Maps.

The obvious play on Toronto’s nickname helped, too.

“It is fun and awesome,” said Geoffrey MacDougall, the foundation’s Dean of Awesome. “But it has intellectual cred at its core.”

Loading... Loading... Loading... Loading... Loading... Loading...

Awesome Foundation grant pitches are due on the 15th of every month.

Avery says she’s a little bit intimidated to be the foundation’s first recipient, but is confident she can pull it off.

“What do people use their roof for? Not much, usually. This way they get to be a part of a piece of art.”