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‘Flying is the ultimate escape because it allows you to unplug from the world,’ says Anthony Lacavera, founder and past CEO of Wind Mobile.Kevin Van Paassen/The Globe and Mail

He's made a living out of being in touch, but it's the moments of complete disconnection that Anthony Lacavera treasures the most.

For the Wind Mobile founder, those moments occur when he flies his four-seat airplane to Ottawa, Montreal or Ontario's Muskoka region in the summer, where he has dinner by the lake before heading home to Toronto.

"Flying is the ultimate escape because it allows you to unplug from the world. When the weather is clear, allowing you to see all the lights over the city, it's absolutely beautiful," says Mr. Lacavera, 41.

A lifelong aviation enthusiast, Mr. Lacavera took two years to build a kit airplane from Oregon-based manufacturer Lancair, along with engineers and aircraft experts who did the lion's share of the work, he says. "I got to see every step of the assembly, from start to finish – I was just fascinated by the whole process," says Mr. Lacavera, who has since sold that plane.

"I'm always racing on so many different projects that it's been amazing to be able to carve out this time for myself."

These days, Mr. Lacavera has more time to pursue his wide-ranging passions. Late last year, he sold Wind Mobile to Shaw Communications Inc. for $1.6-billion – handing over the reins to a wireless communication provider he launched in 2008 out of frustration after he couldn't afford to pay his cellphone bills in university, and which he let go "with mixed emotions," he says.

While his aptitude for math and fascination for how machines are built led him to pursue an engineering degree, the telecom entrepreneur also has a talent for theatre that fell by the wayside when his career took a very different direction.

"My parents' position was to get a degree in something you can get a job; at the time it was about getting into Microsoft or Nortel," says Mr. Lacavera, a third-generation Italian-Canadian who worked at an automotive factory every summer to pay for his tuition.

"But I loved being on stage in high school – I was everyone from Scrooge to Mr. Kirby in You Can't Take it With You; I was in Grease, as one of Vinny's posse. … I loved the emotional engagement involved in putting yourself into someone else's life – and I always told myself I would go back to that.

"I miss being up there. I think about it all the time. I often tell myself that it takes an enormous personal and emotional commitment to do it properly, and I have no training – so my next first step would be to get that. … I love doing things well."

Nevertheless, Mr. Lacavera has still remained firmly planted in the creative scene for the past 10 years, by way of producing several successful theatre productions on Broadway and in London, including the Tennessee Williams classic Cat on a Hot Tin Roof, which won the Laurence Olivier award for best revival in 2010.

"I have met so many interesting people in so many different walks of life in creative industries – from stage and lighting experts to the actors themselves. For the last three I years haven't produced anything because I was so focused on stabilizing Wind, but I'm getting back to it. I'll be producing a play on Broadway this fall," he says.

As the founder and chairman of the Globalive Group, Mr. Lacavera has helped found, finance, operate and divest of numerous companies in the Internet, communications and technology sectors. He's also been able to tap into his resources to assist small charities, leading him to pursue yet another passion – philanthropy for lesser known, often neglected causes.

In 2007, he started charity consultancy Shamba Foundation.

"About 99 per cent of funding goes to 1 per cent of charities in Canada. Canadians are very charitable by nature but tend to only give to causes they recognize like the United Way, Habitat for Humanity or Sick Kids [Hospital for Sick Children in Toronto]. But there are thousands of small causes out there that are starving and not being recognized."

The foundation has gone on to raise more than $1-million to help 42 charities, ranging from the Ontario Arts and Crafts Council and Lawyers Without Borders to Little Geeks, which gives Internet and computer access to underprivileged children.

"We give them space, staff their fundraisers and show them how to collect, pursue and report use of funds, so donors and sponsors feel more comfortable, and they become much better at serving their respective causes," says Mr. Lacavera.

He also puts in 20 hours a week sponsoring and supporting young entrepreneurs through incubator and accelerator groups such as The Next 36 and Creative Destruction Lab.

"We help them create business plans and consider new market opportunities – I think it's very effective. They appreciate having more seasoned entrepreneurs to talk to, who can say, 'Did you think about this?'" he says.

"I didn't know anything about business when I started. I made tons of mistakes – the first five years could have been so much smoother if I had role models and mentors. My story isn't one of spectacular patents, access to capital or special relationships. I didn't have any of these things but I did have good old-fashioned perseverance and hard work.

"I've always had a tremendous affinity for the underdog. I'm very comfortable being one, and that's a big part of what drives me to do the things I do."

Editor's note: An earlier version of this story incorrectly spelled the name of aircraft-kit manufacturer Lancair. This version has been corrected.

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