Ian Black doesn't like following other people's rules – even when it comes to his lunch.
Sitting at a table at Colette Grand Café in downtown Toronto in late October, the 30-year-old general manager for Uber Canada approached his menu as mere suggestions – a starting-off point for negotiations.
He ordered a turkey club sandwich, but then wrinkled his brow at the "Charlotte Salad," composed of endive, avocado and almonds – all of which he deemed unnecessary. "Do you guys just do a plain green salad with a simple dressing?" he asked the waitress. "Or do you only do off the menu?"
The waitress shot him a strange look, but acquiesced. His judicious use of "please" and "thank you,'" and his characteristically disarming niceness, didn't hurt, either.
Mr. Black takes a similar just-do-it approach in his professional life.
There are many who would disagree – many of them taxi drivers – but the mild-mannered Mr. Black doesn't consider himself a rule-breaker. To him, it's simply about changing rules that don't make sense to him – an approach he has helped to apply at Uber Canada as well.
Uber, the Silicon Valley-based tech giant known for an aggressive shoot-first-ask-questions-later approach, has angered taxi companies and lawmakers around the world. After launching operations in more than 60 countries – often ignoring laws and regulations – critics argue that the company operates, at best, in a regulatory grey zone and, at worst, illegally.
Because of this aggressive approach, in just a few short years, Uber has expanded to more than 30 municipalities and regions across Canada. It has plans to launch in 20 more within the next two years.
But even Mr. Black acknowledges that, in order to continue expanding at the pace it has been keeping, the company has some more growing up to do.
Over the past year, Uber has attempted to shift its approach – and public image – globally from brash and bullying to conciliatory and willing to compromise. Instead of flouting existing rules, its staff have worked with officials to help create new ones. In Canada, this shift began happening around the same time Mr. Black was hired.
After graduating with an economics degree from Queen's University, he had gone on to work at management consulting firm Bain & Company in Toronto and New York, before completing his MBA at INSEAD in Paris and Singapore.
But while working at Bain, he said, he was hit with the itch to "go do something." Several of his former colleagues at the company – including his friend Andrew Macdonald – had gone on to work for Uber.
So in May, 2014, at the age of 28, Mr. Black was brought on to lead the company's Toronto operations – a team of six at the time, which has since grown to a staff of about 50.
As an ambassador for a new, "nicer" Uber, he fits the role perfectly.
Between his student-government experience at Queen's, and his penchant for describing everything – from the pace of growth for Uber to his team's willingness to work 90-hour weeks – as "amazing," Mr. Black comes off more as millennial do-gooder than rabble-rouser.
When he says in his unique accent – a mix he describes as part Newfoundland and part British (his grandmother is from Britain) – that the worst rule-breaking he has ever done is throw water balloons at some cars as a kid, you believe him.
"He's a lot easier to get along with than some of the other people in that organization," said Karl Baldauf, a vice-president at the Ontario Chamber of Commerce, which has worked with Uber on promoting the so-called sharing economy.
Mr. Baldauf added that he has heard from colleagues "who say they wish there were more people like Ian at Uber internationally."
Others, like Mr. Macdonald, who preceded Mr. Black as Uber Toronto's manager, credits him with fighting to ensure that the Canadian operations are adequately resourced.
Still, Mr. Black says he had a steep learning curve in his first few months at Uber He remembers sitting in a meeting just six months after he started, and shortly after launching UberX – the controversial service that allows ordinary drivers, and not licensed cabbies, to pick up fares – when he received an e-mail from the company's lawyer.
He quickly turned on the television to see city staff hosting a press conference saying they were launching legal action to try to shut down Uber.
"That counts as a surreal experience. We had all been going about our day, excited about the business we were growing, excited about the fact that a lot of people were using the product and enjoying the product," he says.
To this day, Mr. Black says city staff never met with Uber, or made attempts to speak with the company before launching legal action – a claim that city staff say is not true.
Through a spokesperson, the city's licensing director, Tracey Cook, said the department met with Uber on a number of occasions from 2012 to 2014. After the launch of UberX in September, 2014, she said, city staff offered to meet with Uber, but no meeting ever took place.
Almost a year later – and after the city's legal case was dismissed by an Ontario judge – Mr. Black describes that as one of the most harrowing experiences of his leadership. "We had our team, and that's a pretty scary thing to face as a team member. So I was giving all my thought to 'How do we reassure everyone? … How do we ensure people in the office and also on the roads – the drivers and riders – don't look at this and want to panic?"
These days, Mr. Black's attention is on continuing down the path of rapid expansion – and working with lawmakers across the country to make that happen. In Toronto, city council and staff are working to create new regulations that could legalize Uber.
Last month alone, the company launched in Calgary, and sat down with officials in Winnipeg to explore the idea of opening there too. Mr. Black says any city or region across the country with more than 50,000 people – places such as St. John's, Moncton, Kingston and Sudbury – are prime candidates.
In order to do that, he says, the public needs to be onside – meaning that Uber can no longer afford to be seen as an arrogant rule-breaker. It will also need to keep working with regulators to get new rules created – especially in Toronto, the company's largest Canadian market, which Uber hopes will set a precedent across the country.
Uber also needs to promote a positive image, contrasted with what Mr. Black describes as the "conflict narrative" for which it has become known.
The company will have to grow up in other ways too.
On an average day, Mr. Black gets to the office around 8:30 in the morning and stays until about 11 p.m. Between the Uber rides he takes to various meetings around the city and the meals he has delivered to the office via Uber, he eats, sleeps and breathes work.
The same with his staff – a team of mostly people in their 20s and 30s. Part of that, he said, is generational. "It reflects a different type of work for our generation, which is to go all-in on a project, see it through, and then pause and onto the next one." But also part of it, he contends, is Uber's "hard-driving" culture.
"I don't think myself or anyone on my team could do what we do, the way we do it, for 10 years without totally burning out," he says.
So he says he has turned his attention to developing in the long term a workplace where staff can work hard, but also "be able to go pick up their kids from school."
He acknowledges that the idea is somewhat at odds with Uber's role as innovator and a so-called disruptor. "It's always going to be a group of people who are pushing the envelope, and pushing things forward," he says.
After salad, the waitress walked over with Mr. Black's sandwich. Again, she shot him a look. The sandwich was served with another green salad, almost identical to the one he had gone to the trouble of ordering.
Mr. Black let out his high-pitched laugh. "This is why the waitress gave me a funny look," he said. The side salad had been listed on the menu, but he had not noticed.
Does he not pay attention to details?
"I don't," he admitted, laughing. Still, he said, eyeing the second salad, "I'm excited."
Resides: Downtown Toronto
Place of birth: St. John's
Education: MBA from INSEAD in 2012 (Paris and Singapore campuses); bachelor's degree from Queen's University in 2007. When he was in primary school, his parents, both lawyers, were dissatisfied with the quality of his education. "They looked around and didn't see a lot of great schools in St. John's. So they got a group of parents together and started a school."
Family: Married to Julia, who works for a not-for-profit, since 2013
Favourite Books: Oscar and Lucinda by Peter Carey. "The last book I read was Conrad Black's history of Canada, and I had to admit I skimmed that because it's about 2,000 pages long. … I think that maybe scared me off books for a while."
Favourite movie: The Royal Tenenbaums. "I'm a big Wes Anderson fan, and I think it's my favourite of his."
Favourite music: "I'm a CBC Radio 2 sort of person. I listen to a lot of classical." Also, Canadian indie rock, like Broken Social Scene.
Favourite cuisine: "Pasta. I could eat pasta every day of my life. Probably from Terroni. … I'd be fat and happy."
As a kid: He wanted to be a politician. He door-knocked for the Conservative Party as a teen ("I lived in Alberta, so there was really only one party"), and even devised a plan with his friends that would see them all run for Parliament and form the cabinet. Later, at Queen's University, he participated in model parliament, and was vice-president of the student government.
Now that he has seen politics up close – and especially the tightly controlled party system – he says he is no longer interested. "I'm not good at being constrained or having too many rules to follow."
Uber in Canada: The company operates in more than 30 cities and regions across Canada. In the Toronto area alone, there are about 500,000 Uber rides per month, according to the company. Some Canadian cities, such as Toronto and Edmonton, are moving ahead with regulating Uber. Others, such as Vancouver, have successfully pushed Uber out entirely.