There’d be calls to Justin Crabbe’s Richmond Hill home from teachers worried about the boy frittering away class time staring out the window.

Turns out, having his head in the clouds wasn’t such a bad thing.

Now, at 32, that bored student is a self-made millionaire and the brains behind Jettly, a sort of Uber of the air that is taking the disruptive sharing economy to new heights.

A simple observation — look at all those private planes sitting idle at the airport — led Crabbe to develop a system that links the owners of those aircraft with passengers wanting to eschew commercial flights for charters, whether it be companies transporting executives or, perhaps, the ultra-wealthy planning a golf trip to an exotic locale.

While about 70 to 80 per cent of its business is corporate, Jettly recently arranged for 20 planes, at about $55,000 on average (all figures U.S.) per round trip, to take revellers from New York to the Burning Man festival in Nevada, the planes landing on a temporary landing strip in the desert. Some of those flyers wanted high-end catering and, in one case, that included 40 bottles of champagne at $3,000 a pop.

Another recent multi-stop charter went from Vancouver to Fiji with a price tag of $689,000.

“These people are booking at the click of a button,” Crabbe says. “It truly is amazing to see these types of numbers come through. So, as you can imagine, the growth can be tremendous in this particular market.”

Jettly got off the ground in 2016 and now has 15 employees and can fly to 190 countries and territories.

It took off because Crabbe, a serial entrepreneur who figures he’s started between 40 and 50 companies, is also a pilot.

When he’d fly out of Buttonville Municipal airport it struck him how little support there appeared to be for the owners of those underutilized private planes. While there were other online, on-demand charter services as well as brokers — who connect customers to flights with varying markups — he believed he could come up with a streamlined approach that offered better value to flyers while getting more of those planes off the ground.

As a proficient computer programmer — apparently his concerned teachers were wrong — he set to work.

Through an app he developed, the owners of more than 9,000 planes are now connected with 28,000 potential customers who pay between $370 and $997 monthly for a Jettly membership, depending on how many flights they foresee booking. Non-members can also charter a flight for a fee.

While charter flights remain, largely, play toys for rich individuals and large corporations, the story of how Crabbe came to carve out a piece of that lucrative market has more of a common touch.

It didn’t arrive out of thin air but is instead the latest business endeavour for a self-described hustler. He’s been mining data on the internet and building businesses with that information since he was a teenager.

“While my friends were playing sports or out drinking or whatever they may have been doing most of the time, I was hunkered down on the computer,” he says. “I still work between 60 and 80 hours a week, depending what we’re doing. But for me, it’s not work. It’s fun.

“Creating a business is a hobby for me.”

Even as a child, back when teachers fretted about Crabbe — his dad recalls Justin as being “average or just a little shy of average” as a student — there were hints that he had an innate ability to profit from people’s needs.

Not to the extent, perhaps, that anyone expected him to one day be mentioned in business articles alongside Warren Buffett, but Crabbe always seemed guided by a wise-beyond-his-years marketing moxie.

It was evident in Grade 3, when buying and trading POGs — game pieces based on milk bottle caps — was the schoolyard rage. Crabbe cherished his own collection that easily filled a shoebox. Then one day they were gone.

“I sold them,” he told his dad.

“But you loved those things,” his father protested.

“But in six months nobody will want them,” the boy explained.

“So he caught the top of the market essentially,” recalls Justin’s father Don, a Richmond Hill lawyer. “It started really young, those instincts to make money in a market environment.”

He was also enough of a computer whiz that in Grade 9 he became the go-to guy for diagnosing the laptops used in St. Robert Catholic High School’s e-learning program. It fell to him to decide if they needed to go back to Toshiba for repair. He had little interest in parsing a sentence but he could take a computer apart and put it back together. He just learned differently.

“There’s something gifted about the way his mind works and how he can process things,” says Demetra Mandrapilias, a friend from those teenage days, who worked with Crabbe on his early e-commerce ventures. “We all knew Justin was destined for success but not in a conventional way.”

It was also in high school that Crabbe figured out how to access the computer code that allowed consumers to get in virtual line to purchase a Motorola Razr, the hot flip phone at the time. He began selling that code on eBay.

“I remember vividly making $600, $800 while I was sleeping every night,” he recalls. “And for a kid like that, that’s incredible money.”

Crabbe also made money burning music CDs and selling them to his friends. Then at an age when many kids are hanging out at places like McDonald’s, he was a 16-year-old manager of one the chain’s restaurants near his home, working evenings, weekends and overnights. He says he was told he was the youngest store manager in Canada at the time, an odd situation because he’d often be behind the counter with other teenagers from his high school.

“I’d be telling them what to do with the authority to do it,” he says. “That was pretty fun.”

But while he continued to tinker with computers and educate himself about the internet, Crabbe had a different dream. He wanted to be a police officer. He enrolled at Seneca College and did well in the two-year program. But as a 19-year-old graduate with no real life experience, he wasn’t ready to work in the field. So he enrolled at York University in sociology with the thought that would make him a better officer. A course in information technology there helped change his life’s path.

“We were doing projects on the internet and one was to create an online store,” Crabbe recalls of a time when Shopify was in its infancy and Amazon was not yet the behemoth it is now. “So I kind of fell into internet-based businesses and one grew to the next.”

That first project was a business importing chemicals for use in university labs and though he says he had only “rudimentary” business skills, he was making money. He left York halfway through his second year.

What Crabbe understood well was search engine algorithms and he learned to discern what people wanted, predict trends or to anticipate the next fad. Then he’d import those items.

Mandrapilias recalls her friend as someone who worked for everything he got; it wasn’t handed to him by his parents like some of their peers. He drove an old white pickup truck and would hang out with the gang but he wouldn’t linger. He’d go home to program his computer, toiling away on a keyboard in his parents’ basement.

“People see his success and are like, he just one day built a bunch of money-making sites and found success that way,” she says. “But it was this long process of figuring out how to create those types of businesses and marketing initiatives. He was very, very driven.”

At one point, Crabbe worked out of a rented 3,000-square-foot house in Richmond Hill that quickly filled with imported products. Crabbe recalls having a dozen employees including an art director, a photographer, web developer and customer-service staff packing and shipping items.

“I was 21 or so in this house. Instead of a kitchen we had desks all over. Instead of a living room we had a boardroom table and things of that nature,” he said.

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“And I lived upstairs. But I had so much flak from the neighbours because of the amount of trucks that were coming by and the fact that I was running a commercial operation out of a residential house. The city was called and there were a lot of problems. It was chaos. That was a short lease.

“That was very early days and sometimes you don’t really know what you’re getting yourself into until you’re in it.”

Crabbe moved into an office in Richmond Hill and rented a warehouse in Texas. He also came to understand that the big money was in importing “not-so-sexy” items such as gelatin caps for pharmaceuticals or tooth whiteners. He would travel to China twice a year, visiting trade shows, seeking products he thought would sell in North America.

He says he recalls multiple times he’d go to the bank with a series of cheques worth $100,000.

“This was all done with the power of the internet,” he said. “The internet has been such a pivotal thing for my life that I’m lucky to have grown up with it as a millennial.”

Crabbe still travels to China, but “finding products is not as easy. You’ve got services like Shopify that have made it very easy for anybody that wants to start a business in their basement. They can do it literally overnight where, when I was doing it, I had to code it myself. I had to create it by myself and develop and maintain it all myself. Now you’ve got services that make it easy and that increases the competition and the competition has flooded the market with a lot of e-commerce-type products.”

Crabbe says the growth now is mostly in mobile apps like Jettly, which he programmed himself to create the central booking platform.

He now considers American billionaire Buffett, though in a different financial stratosphere, to be one of his competitors. In 1998 for $725 million, Buffett’s Berkshire Hathaway conglomerate purchased NetJets, which sells fractional ownership in private planes, guaranteeing access for a certain number of hours annually.

Buffett, clearly believing in the future of charter travel, committed almost $18 billion in purchasing more jets in 2012. In 2018 NetJets announced the option to purchase 325 planes valued at up to $10 billion.

Crabbe invested $100,000 of his own money for his start-up, money used to set up the network and other development. He says he realized its potential when Jettly did more than $1 million in sales in its first year flying only within North America.

Jettly is similar to the travel website Expedia. On the app, a member submits a flight request stating desired dates and destination. That call then goes out to a number of operators and pilots in the area. Those plane owners then send notifications with their availability, cost and details about their aircraft. Options could be anything from a single-engine propeller plane to a Boeing 737 outfitted with first-class seating; some of the jets are owned by corporations that use the Jettly network to supplement the ownership cost.

The customer picks one. The average booking is in the $25,000 to $35,000 range.

Jettly makes its money off memberships as well as a 10 per cent flight arrangement fee on each booking. The primary target market for the company is executives who typically fly first class or business class but might find a charter more luxurious, convenient and, if there are several travelling together, cheaper.

John Gradek, who lectures on aviation issues at McGill University, says that despite someone like Crabbe “trying to democratize the world of aircraft charters,” it will always be a niche market for the wealthy and corporations.

Any value in a company like Jettly, he says, is for the airplane owners. Depending on the aircraft, it typically costs between $500,000 and $1 million in annual fixed costs to maintain a plane.

“So for them to get somebody to contribute to keeping those costs down, that’s what this game is all about,” he says.

While Mandrapilias says Crabbe is “not flashy at all” — his preferred attire is jeans and a golf shirt — he does enjoy his newfound wealth. It’s not unusual for him to fly off in his own Cherokee Piper to take a friend for an afternoon of shopping in Manhattan or for dinner in Niagara-on-the-Lake or Montreal. He has a $450,000 Icon A5 on order — a significant upgrade on the plane he has now — and hopes to take delivery soon. It’s the same plane former Blue Jays star Roy Halladay was piloting when he died in a crash in 2017.

He drives a Porsche — which he bought used because he couldn’t justify the cost of a new one — owns a two-storey penthouse condo in downtown Toronto and works out six mornings a week as a dedicated crossfit fanatic. He describes himself as “happily single” and travels frequently. Stops this summer included Spain and Greece for business but he made time for scuba diving in both countries. Crabbe is also an avid hang glider.

Typically, he doesn’t use Jettly when he flies overseas.

“I’m kind of a frugal flyer in terms of using the company funds when it comes to transport now,” he says. “Those flights can be $100,000 and I’m one person. I’d rather reinvest it in the company to grow.”

That changes in North America, where he mostly uses a plane from the Jettly network if he’s not flying himself.

Crabbe says he’s not sure what he’s worth but “I can guarantee you I’m a multimillionaire. I live well. I enjoy my life but I don’t splurge by any means compared to what I could be doing. I’m really focused on building businesses.”

Crabbe, who remains Jettly’s sole owner, says venture capital firms have asked to invest but so far he’s had no interest in giving up any control of the company. He hasn’t worked for anyone else since he turned 20 when his e-commerce ventures began in earnest.

But as he pushes to expand Jettly, he said he may reconsider that philosophy because of the expertise attached to some of those venture capitalists.

“It’s the information and the talent that can be brought in through the (venture capitalists) that’s more attractive than the actual capital,” he says. “It can ignite a business.”

With the majority of customers in the finance industry, the company is looking to add a London office to existing hubs in Toronto and New York. That’s a place, he says, where bookings are on the rise. He said Jettly also has many ultra-rich Russian businesspeople who use the app but getting a physical footing in Russia is a challenge without speaking the language and understanding the culture.

Crabbe feels he is at the beginning of a career creating businesses and investing. He’s now looking at developing app-based companies in real estate, financial technology and in the medical field.

“I’m in my infancy,” he says. “And the sky’s the limit.”

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