Fred Dionne turns a passion for technology into a prosperous legal career

October 02, 2017

When Fred Dionne first set eyes on his sister’s brand new home computer—back when home computers ran on DOS and featured a black start screen with a white flashing prompt—he immediately wanted to learn everything about how it worked.

So he scoured the library for any book that could offer insight into the world of computer programming. He picked the brains of friends who dabbled in coding. Finally, he tried his hand at it himself—and, unsurprisingly, he loved it. By the age of 17, he was coding productivity software for his mom’s heating and air conditioning business—and improving her sales as a result.

Since that time in the late 80s, Fred has followed his passion and leveraged his interest in technology to pave an interesting and prosperous career path—albeit an unconventional one. He didn’t land a job in Silicon Valley—or even obtain a computer science degree, for that matter. Instead, he pursued the law as a means of satisfying his technological itch.

Trying careers on for size

That’s not to say he didn’t try to take a more traditional approach. His post-secondary career started as a Computer Science major at the Université de Montréal—but it just didn’t feel right.

“I went into computer science, but four out of five courses were purely math and my brain doesn’t work that way. I just wanted to be creative and code some software,” he recalls. “So I quit and, for a while, I didn’t know what I wanted to do. But I was fascinated with international diplomacy, international laws and the United Nations, so I ultimately decided to go into political science—and I did very well, because I was passionate about it.”

This interest in foreign affairs—and, in particular, the UN Blue Helmet peacekeeping missions taking place around the world in the early 1990s—also inspired him to join the Canadian Forces.

“I was fascinated with conflict resolution, so I decided to join the army. Well, I am not sure this sounds right. But I was young and fearless.”

“I wanted to become an officer, not just a soldier—a platoon commander where I could lead about 35 people, make decisions, understand tactics and lead by example,” he says. “It was fascinating, but probably the most difficult experience of my life.”

Over two summers, Fred went through gruelling training as a platoon commander. He was barked at by “crazy commando teachers” virtually every day and was forced to go on very little sleep. Despite all this, he battled on, and became one of the 25 percent to make it through the final phase of training. He ended up serving as a platoon commander with the Fusiliers Mont-Royal.

“I did it, and it changed my life. It altered the way I saw change and challenges. After that, I felt like I could do anything.”

An introduction to law

In 1994, in between summers of platoon commander training, Fred applied for—and was accepted into—law school at the Université de Montréal. At the time, he didn’t know much about becoming a lawyer—he just knew he wanted a good job one day.

“I had no clue what the Civil Code of Québec was. I didn’t know there was a distinction in Canada between civil and common law. I was really more interested in international law.”

“In those early days in law school, I discovered business law and was immediately hooked. I loved learning about how corporations work—the roles of shareholders and officers,” he recalls. “So it didn’t take me long to switch from an international law focus to corporate law.”

His love for corporate law ultimately led him to a junior associate position at Stikeman Elliott in Montréal, where he spent his time working on M&A, securities law and general corporate matters. But around 2000, as the tech boom heated up, his passion for technology re-emerged—and he decided to leave law to launch a technology company focusing on location-based services.

“At the time, we were looking to use location technology and the GPS capabilities of cell phones—there were no smartphones back then—to pay for taxi rides with phones. And this was way before Uber came onto the scene,” he laughs. “But the big players in that space at the time were telecom companies, not Internet companies—and they didn’t want to share any data. A few months after starting our business, the telecom industry crashed and it became really difficult to run the company.”

Technology pioneer

Looking back, Fred believes his business idea was about 10 years premature—and says it’s a testament to the importance of timing in business. Regardless, in 2001 he was contemplating his next step. A friend of his from Stikeman had already moved to Osler, and convinced Fred to join him to help build the top legal technology business group in Montréal.

As the tech bubble burst, the Osler team reached out to some of the Silicon Valley lawyers that were suddenly unemployed or eagerly wanted to come back to Canada and invited them to join the firm. Before long, the Osler technology business group was formed in Montréal. And it was an amazing experience.

“It was night and day compared to my early years in law. I was able to become a really good attorney and work on a lot of interesting deals.”

While Fred’s focus was primarily on technology, due to the set-up of the Osler office, he was also granted the opportunity to team up with other lawyers in different areas. He worked with big venture funds and technology companies, and while the tech bubble did have an impact on the market, the group drummed up enough business to become true pioneers in the space.

“My time at Osler really shaped the way I am as an attorney. The four years I spent there were really crucial,” he says. “It’s cliché to say, but it’s important to have mentors. Mine at Osler affected my practice in a really positive way—they taught me the importance of writing good contracts, having good judgment, understanding client needs and adapting your advice to those needs.”

On his own

In 2005, Fred’s entrepreneurial itch once again reared its head. He wanted—needed—to break out on his own and start his own company. He just didn’t know immediately what that company would be. After a few months, he started to notice a distinct demand for his legal skills in the technology industry, so he set out to launch blue HF—a boutique law firm focusing solely on SMEs and early stage companies in the technology sector.

“I never intended to start a law firm, but that’s what happened.”

“It was a one man show at the beginning, but then I became too busy so I started recruiting former colleagues,” he says. “It’s been a very successful law firm for more than 10 years—we’ve built an excellent reputation and often work alongside the big firms.”

Fred practised full time at blue HF until 2014 when, once again, he set his sights on new experiences.

“I was starting to get bored—and I was seeing a new shift toward mobile video in the market,” he explains.

The law firm had earlier given discounts and some very flexible payment terms to a promising new start-up in exchange for warrants in the company. Around 2014, that start-up sold for a substantial amount of money and Fred, in turn, had some “venture” cash to play with. So he decided to start—now a shoppable video platform and technology company for interactive video content.

“I wanted to go back to my roots—computer science and technology. Technology has always been a big part of my life. I figured I’d create the product, build a team and succeed. But it’s never that easy,” he laughs.

That’s not to say things aren’t going well. is currently in the process of creating a new interactive video experience protocol that will work on blockchain and use crypto economics. And Fred plans to eventually take it far beyond video to include virtual reality, augmented reality and artificial intelligence.

“We plan to launch our product by the end of the year and I’m very excited,” he says. “We talk a lot about the shared economy with applications like Uber and Airbnb, but now we’re seeing a new model called shared prosperity. It’s a different way to look at business and technology innovations.”

Technology is the future

While Fred doesn’t expect everyone to be as technologically-minded as he is, he does believe lawyers—particularly those starting out—would be well-served to understand the space moving forward.

“Artificial intelligence is probably one of the first technologies that will disrupt the legal industry, so I think up and coming lawyers should understand AI and technology,” he says. “You can’t only rely on your legal skills going forward—you need to understand what’s going on in the technology space.”

That said, he does believe in the merits of gaining legal experience early on, to make it easier to decide what route your career will ultimately take.

“The more experience you get—the more transactions you work on—the better. You need a lot of exposure, so don’t be afraid to sweat at the beginning of your career,” he advises. “You won’t always see the value of the hard work you’re doing—and you’ll likely want to do more interesting work—but it’s important to remember that it’s a process. By the time you get your first five years of experience, you’ll really discover what you want to do in life.”

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