For Blair Wiley, the only career worth having is the one you’re passionate about.
If there’s one thing every lawyer can agree on, it’s that pursuing a career in law isn’t for the faint of heart. Like it or not, success is often linked to some measure of personal sacrifice. And in Blair Wiley’s opinion, if you’re going to log long hours at the office, that time at the office better be worth it.
“In this profession, it’s important to work hard, but it’s also important to be strategic,” he says. “Find the things that really light your fire, because this career is long and, if you’re not passionate about the work, it can become very difficult to reach your goals.”
It's a philosophy Blair adopted early on when he was a co-op undergrad student at the University of Waterloo. Back in 2003, his goal was to pursue a career in business until a co-op placement with in-house counsel at Ericsson, a network and telecommunications company, changed his mind.
So, Blair promptly set out to obtain his law degree at York University and landed a coveted position in Osler’s student program in 2006. The broad-reaching program allowed him to try on numerous different legal hats which, in turn, helped him determine which area of law he was most passionate about.
“I was always interested in business and, being in Toronto — the heart of Canada’s financial services industry — I was immediately drawn to the capital markets, banking and securities regulation,” he says. “My mentors at Osler helped me find my niche in the securities law area. It was definitely a natural fit for me.”
An aspiring Osler lifer
Blair thrived in Osler’s unique environment. After completing the student program, he returned to article and was offered a position as an associate in corporate and securities. In 2016, he became a partner.
Over the span of 12 years, Blair had the opportunity to work with many of Osler’s most important clients and on some ground-breaking files. After starting as an associate in 2008 — the week that Lehman Brothers collapsed in the United States — he played a hands-on role in the General Motors restructuring through most of 2009.
Following that experience, he got to support many of the firm’s largest financial industry clients — like the Canadian banks, Goldman Sachs, BlackRock and Morgan Stanley. His hard work led to a secondment at the Canadian Securities Transition Office, where he helped develop policy for the proposed national securities and derivatives regulator.
Throughout, he was consistently inspired by the humility of his more seasoned colleagues — and the team-focused Osler culture.
“At Osler, you’re surrounded by leading practitioners across disciplines and you get to work with some incredible clients. Yet those leading practitioners have a striking amount of humility,” he explains. “Osler has created a culture of excellence without bragging or boastfulness; it’s more of a quiet confidence. People are valued based on their hard work and excellence. It’s not about being the loudest in the room.”
Osler’s unique culture and work opportunities made it the perfect fit for Blair. So perfect, in fact, that he expected to play out his career at the firm as an Osler “lifer.” But when he shifted to the fintech realm in 2016 — focusing on emerging and high growth companies — he discovered a new passion he felt compelled to pursue.
A new normal
One of Osler’s first fintech clients, Wealthsimple, was a small start-up with global ambitions. Blair worked with its founding team over the years, and they were eager to get him on board. At first, Blair politely declined — but after a while he relented.
“It was a unique opportunity for someone in my stage of career and it was an exciting challenge,” he recalls. “That said, it wasn’t an easy decision to make. I loved working at Osler. But the opportunity to help lead a high growth start-up operating in an industry that I was really passionate about — was something that I ultimately couldn’t pass up.”
When Blair finally made the switch, he wasn’t struck by an overwhelming sense of culture shock. He still had incredibly busy days dealing with a wide variety of legal issues. That’s not to say there weren’t distinct differences. For one thing, he was no longer limited to giving legal advice to others. In his new role, he was also responsible for putting that advice into action. He also has the opportunity to flex his business muscle and help the new company achieve its strategic growth initiatives.
A year and a half on, he still finds working for a start-up incredibly rewarding — but without the support of a firm’s resources behind him, it can sometimes be challenging.
“At Osler, I had terrific support — researchers, students, junior lawyers and other partners who would help get me through almost any issue,” he says. “Start-ups don’t have those resources, so many things are bootstrapped. I kind of like that scrappiness, but at the same time I miss the depth of Osler’s resources.”
Fortunately, Blair still has access to those invaluable resources from time to time. Not only has Osler sent articling students and secondees to Wealthsimple, but Blair has maintained strong relationships with his former colleagues. “It’s really rewarding to maintain those personal and professional relationships. It’s something I’d hoped for when I left, and it’s been even better than I expected.”
These days, Wealthsimple continues to keep Blair busy — just as busy as he was while working at Osler. This makes it challenging for him to spend time with his family — his wife and two daughters, ages four and seven. As a result, he’s had to get creative with how he splits his time.
“It takes a lot of planning and I don’t think I’ve mastered it yet. I’ve tried to embrace working from the cottage over the years, which made it a little easier to work remotely during COVID,” he says. “But, to be honest, it’s really hard. I haven’t found the magic pill.”
When he does find the time, he enjoys getting outdoors in nature — either skiing in the winter or simply kicking back at the cottage in the summer. And he’s always looking for opportunities to better himself in some way, whether that’s through a good book or a compelling documentary.
“I’m committed to continual learning. I’m always looking for ways to challenge myself — to know more and be able to do more,” he says. “I just can’t be content with the idea that what I know is enough.”
Blair Wiley is the General Counsel and Head of Regulatory Affairs at Wealthsimple. Prior to joining the global fintech company in 2019, Blair was a partner at Osler, specializing in dealer/adviser registration, derivatives, asset management, investment funds, marketplace rules and fintech. He began his career at Osler in 2006.