The unexpected opportunity

When Andrew Arruda (JD’14) graduated from the College of Law in 2014, he knew exactly what he wanted to do and where he wanted to go… until he received that phone call.


Andrew Arruda (JD’14) is one of those rare few who seem to move through life with eyes (and mind) wide open.

He’s made a name for himself as co-founder and CEO of ROSS Intelligence, the world’s first artificial intelligent (AI) legal research assistant.

He’s also become a sought-after speaker on AI, legal innovation and access to justice. He’s a member of the Forbes 30 Under 30 class of 2017 and has been quoted in The New York Times, Fortune, Inc. Magazine, Forbes, La Monde, TechCrunch, The New  Scientist, The Guardian, The Atlantic, The Financial Times, the BBC, CBC, CBS and CNBC.

Impressive credentials. During a telephone interview where one of us was enjoying the balmy climate of San Francisco where ROSS Intelligence is now based and the other was in a bunnyhug to ward off minus 35-degree temperatures, it’s no surprise that he talks easily about goals and ambitions. But he also talks about his experiences and lessons learned with remarkable mindfulness. It’s almost unsettling—Arruda’s just turning 30, after all.

It’s this mash-up of exuberant entrepreneurialism and laid-back humility, youthful optimism and wise-beyond-his years insight that have Arruda carving a place for himself as a speaker, collaborator and mentor in the global world of AI.

“The fact that my grandparents moved to Canada late in their lives so that we could have a better education, that’s the most entrepreneurial thing I can think of,” said Arruda.

Setting sail

A first-generation Canadian, Arruda grew up in Toronto’s Little Portugal, a vibrantly diverse community where his parents and grandparents settled after emigrating from Sao Miguel. It’s an island in the Portuguese Azores, a stunning archipelago in the middle of the Atlantic Ocean. It’s where Arruda traces his entrepreneurial roots.

“My grandfather was a fisherman who learned early on that he could make a better living by signing on to fishing boats sailing north. He’d be gone for five and six months at a time, while my grandmother stayed home to raise their family. She also ran a small accounting business and had a side business salting and selling fish, which actually turned quite a profit,” Arruda said.

Arruda grew up on his grandfather’s stories about faraway places, chasing your dreams and doing the things you love.

“When I think of early influences, it’s those stories and those lessons that come to mind. My parents and grandparents strongly believed in the importance and value of education—that was why they came to Canada.”

Growing up first generation

The Arruda family’s hope of a good education for their children came true when Andrew went off to private school in Toronto. He got good grades, played sports and served as co-president of the school’s student council in Grades 11 and 12.

“It was such an interesting time of life. I learned about making hard decisions in short timeframes and how to motivate people when things go bad. You learn that people are counting on you. For me, that was always an honour,” said Arruda.

Arruda jumped right from high school to the University of Toronto (U of T), where he lived in residence on the downtown campus. It was the first of many moves beyond his familiar Toronto “bubble.”

Hitting the high seas (sort of)

With his undergraduate days drawing to a close, Arruda was scoping out his next step—law school. In high school, he’d been impressed by a boutique law firm in Little Portugal.

“I saw their impact on the community and how they represented businesses and people in my neighbourhood, and I wanted to be part of that,” said Arruda.

Arruda wanted to attend a law school outside his Toronto comfort zone. “I benefitted when I moved away from home for university, and I realized that I needed to move even farther away to expand my horizons—a bit like my grandfather.”

It was a summer visit to campus that sold Arruda on USask. “I fell in love with the campus, but it was more than that. I felt immediately accepted, like it was an environment where you could explore different ideas. I felt cared for by the professors and the community as a whole,” said Arruda.

Glen Luther (LLB’81), his criminal law professor, was a favourite. “I would call him Professor Luther and he’d insist I call him Glen. That’s how the college felt, more like a family network than a school.”

In Luther’s class, Arruda began to realize not everyone had access to legal services, and our society’s easy notion of “justice for all” didn’t always work.

“We travelled to the penitentiary to work with people who’d been deemed noncriminally responsible, which exposed me to people who were overlooked in the legal system. I thought, that’s where I want to make a difference,” said Arruda.

While at USask, Arruda started up the college’s chapter of Canadian Lawyers Abroad (now known as Level). After convocation, Arruda returned home and began articling with the neighbourhood law firm he admired. Things were going along swimmingly—until that phone call.

Hello, this is your future calling

On the other end of the phone was Jimoh Ovbiagele, a U of T computer scientist. He and Arruda had met at a party and talked about artificial intelligence and what role it could play in making the law more accessible.

“It wasn’t a really long conversation, but the idea just wouldn’t go away,” Arruda said. “When Jimoh called a few days later to ask me to join him and Pargles Dall’Oglo, another U of T computer scientist, in developing an AI platform to democratize the law, I couldn’t say no,” said Arruda.

And the rest is history? Arruda laughs softly over the phone.

“Actually, it was more work than I ever imagined. But then, I can’t say any of us really knew what we were getting into. It was the sheer energy and excitement and belief in what we were building that pushed us forward, and also maybe some naivete about how long and how hard we’d have to work to get it going.”

ROSS is a legal research engine that uses AI to automate legal processes, making them more efficient and less expensive. ROSS can read through a million pages of case law in a second and find relevant information in minutes.

The idea had legs from the get-go. A few months in, the team had garnered investment from Dentons, a global law firm, and Y Combinator, a Silicon Valley-based accelerator.

“About a year in, after we released the first versions, we started hearing from lawyers about how valuable it was, how easy the platform was to use, how much they loved it—that feels so good, you never get tired of hearing it,” said Arruda.

In 2017, the company opened ROSS North, its AI research and development head quarters in Toronto. Toronto’s mayor, John Tory, and U of T president Meric Gertler, were among the dignitaries on hand to welcome ROSS back to Canada.

The partners have stayed true to their vision of democratizing law.

“Everyone needs a lawyer at some point; the catch-22 is that we can’t all afford the lawyer we need,” Arruda said. “We always knew AI could benefit law firms, but we made a promise from day one to also give our product away for free to deserving organizations—and we’ve done that.”

Mentoring connections

Increasingly, Arruda has found himself in demand as a speaker and mentor. After speaking at a TED Talks event in San Francisco on AI and access to justice, he’s been invited to speak at events in the Czech Republic, Sweden, Norway, Singapore, France, Sweden, Italy, and across Canada and the US. He’s inspired students from USask to Harvard, Duke and Vanderbilt universities.

“I love it,” he said. “You see the world through such a diverse lens, and that makes me a better CEO. It’s the same with collaboration, the more we collaborate, the more effective we become. I see myself acting more and more as a connector—I  connected a company in Singapore to one in Sweden. That’s exciting. Sometimes, it’s even hard for me to believe it’s me doing it.”

In the world of start-ups, collaboration transcends business. A quick check of Arruda’s LinkedIn profile shows he’s currently serving on several international boards and groups. Nor has he forgotten his alma mater. Arruda was named to the College of Law Dean’s Advisory Council in late 2018 and has been a mentor with Co.Labs, a Saskatoon-based tech incubator, since 2017.

That’s the other thing about collaboration; it isn’t just lip service, it demands real time and energy.

“As a Co.Labs mentor, I have formal office hours and set aside a block of time to meet with founders and talk about pressing issues,” Arruda said.

Why make time in an already busy schedule? “I just knew I wanted to be part of it. Saskatchewan was founded by people who had to push through hard times to create something, and that mirrors the entrepreneurial spirit of start-ups.”

Always mindful of life’s journey, he added, “I feel like I was born and raised in Toronto but grew up in Saskatchewan.”

Creating a tech culture in Saskatchewan

Jordan Dutchak is slowly changing Saskatchewan's tech culture at Co.Labs, a nonprofit tech incubator dedicated to enhancing the province's growing tech sector.

Leslie-Ann Schlosser

When you walk into Co.Labs, you can immediately sense the space is a little different from your traditional cubical-laden office.

A mini Silicon Valley in its own right, Co.Labs is a non-profit, provincially and federally funded tech incubator that provides Saskatchewan startups with the mentorship, space and programming to expand their businesses locally instead of moving to different centres, like San Francisco or Toronto.

Startup technology and Saskatchewan— something that traditionally does not have a strong connection, but a perception that Jordan Dutchak (BCOMM’16), executive director of Co.Labs, and the rest of the Co.Labs team is slowly transforming. Tech  culture has shifted on the Prairies in recent years as more young people graduate from courses, like USask’s computer science program, with the knowledge required to transform the industry.

Since his days as a USask student, Dutchak saw this trend coming and recognized that there was a community forming around it and there was an opportunity to catalyze in its growth.

Co.Labs has helped over 73 startups generate more than $5.5 million in revenue, raise $6 million in investment, and hire 93 employees since its inception in 2017. Dutchak said it’s the collaborative nature of Co.Labs that makes him excited to come to work every day.

“Being able to sit down with these companies and prevent them from making the same mistakes as other startups [can] rapidly increase their speed. When you take the culmination of these conversations and meetings over time, you’re constantly learning and expanding a collective ‘brain trust’ that can scale over time to help new aspiring tech founders,” said Dutchak.

Townfolio is just one example of a Co.Labs success story. Have you ever had questions about towns or municipalities that Google just can’t answer? That is where Townfolio comes in. The company’s database provides over five million visualized data points on over 38,000 cities and towns.

It is one of the first companies to get their groundings with Co.Labs and has since partnered with 600 government economic developers across North America from small town to big cities who use its data for investment attraction.

Ryley Iverson (BCOMM’13) is the co-founder of Townfolio. He says Co.Labs was able to give him the base for his company and offered the collaboration and support needed to grow. He encourages the next generation to take a leap into tech culture.

“Alumni and students [should] consider that this is a thing here. Our tech scene is amazing. Given the resources put into it, it is very phenomenal where it’s going.” 

If you are a USask alumni working in tech, at home or abroad, and want to get involved as a Co.Labs mentor you can email for more information.

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