Brenda Irwin, the founder and general partner at the Relentless Venture Fund, was leaving her Kitsilano home one day when she stepped awkwardly on her stairs, stumbled, and snapped her foot. She was in excruciating pain and was pretty sure—but not 100 per cent sure—that she had broken a bone. With a meeting scheduled in the financial district shortly, she had a dilemma. She contemplated what to do next, ultimately deciding to get in her car and drive downtown. She parked at St. Paul’s Hospital and limped to the office of IWJ Law, where she regularly holds meetings because her lawyer Dayna Forsyth is a principal there.

She made sure to arrive early so nobody could see her struggle. She then sat through an entrepreneur’s first ever pitch to a venture capitalist (VC). She endured the entire presentation in immense discomfort. If there was ever a moment when she evoked the spirit of her firm’s name, it was definitely this act of obstinacy. “My analyst Isabella was there too,” Irwin told me, leg brace on, as we sipped coffee at Musette Caffé, a couple of weeks after the break. “I didn’t tell her until the entrepreneur left, and then I looked at my foot and I said, ‘I think I need to go to the ER.’”

This wasn’t Irwin’s first broken foot, and technology investing is not Irwin’s first career. Long before her name became synonymous with health tech-focused capital, Irwin was a science and physical education teacher on the other side of the country. Ironically, she showed up to meet her new principal and learn the specifics of her first teaching assignment with a cast and cane too.

Now, in the same way that her first experience of breaking a bone helped her manage the second time, it’s clear that her first career—all those years connecting with diverse people and communities, coaching teams, and managing difficult personalities—has given her a few secret weapons to sagely navigate the frenetic world of startup investing. The way Irwin sees it, both endeavours have, in unique ways, allowed her to do what she does best: “What I love about business and venture and investing, and what I loved about teaching,” she explains. “It’s finding the potential in people and discovering the unexpected.”

A chronicle of Irwin’s life experiences turns up a number of common factors in her journey from Mount Elgin, Ontario to her current seat at the head of the proactive health startup table. They include chance encounters with remarkable individuals, the forming of unique bonds, hard work, and many trips through uncharted territory. Irwin has followed that path more than once, and it’s clear that, so far, her internal compass has been pointing in the right direction.

Back in the 1980s, after Irwin finished studying human biology at the University of Guelph, one of her first tastes of the tech industry was a job at EMJ Data Systems. EMJ was founded by Jim Estill, one of Canada’s most prolific angel investors, executives, and philanthropists. He was a founding investor in RIM and in 2015, he garnered international recognition for personally pledging $1 million to settle 50 Syrian refugee families. Irwin has known Estill since she was ten.

At EMJ, she worked as a marketing manager and remembers when the first 100MB hard drive came out. “I was like, what? 100 megs,” she recalls. “That’s not possible.” EMJ was the only distributor of Acer computers at the time. It eventually became a publicly traded company on the TSX.

Irwin was busy with her day job, but she also happened to continue studies at the University of Guelph taking evening English courses (an eclectic mix of Shakespeare and children’s literature), eventually getting to the point where she just needed a full semester to get a second degree. She ended up taking a leave of absence to complete it. As we know now, she didn’t stop there. She applied and got into teacher’s college and then went on to teach in North York for five years.

“You are going into the era of: You don’t need to have the same career for your whole life,” a female business leader shared at an assembly when Irwin was in grade 12. She weighed this advice when considering if she might leave her job as a teacher. Disillusioned with the direction that the Ontario education ministry was heading, she decided that the time had come for her next adventure. Partially on a whim, Irwin studied for the GMAT over one March Break week and wrote the official test on the Saturday. She got a decent score and then applied successfully for her MBA at the University of British Columbia (UBC).

It was through her MBA studies that Irwin met a man by the name of Raphael (“Raffi”) Harry Amit. Raffi, as Irwin calls him, was one of her UBC professors. But he isn’t just any professor. Right now, Raffi is currently The Marie and Joseph Melone Professor at the prestigious Wharton School at the University of Pennsylvania. Raffi gets quoted in publications like the New York Times, Wall Street Journal, Bloomberg, and CNBC. Raffi is, as Irwin describes it, “one of those rare professors who is also quite active in the business community.” And here’s a fun fact for those of you who know your B.C. technology history: Raffi served as chair of the board of directors of Burnaby-based Creo Products Inc. for 6 years, right until the company was acquired by Kodak in May 2005. Raffi is the real deal. He taught Irwin a strategy course. His significance does not stop there, however.

Part of the MBA program Irwin was enrolled in featured an international component, which allowed her to finish the degree in Asia at Hong Kong University of Science and Technology (HKUST). One day while studying abroad, she received a short email from Raffi. He wrote, “There’s a job you need to apply for.”

The position was at BDC Capital in Vancouver. Raffi had given the recruiter for the position Irwin’s name—and only Irwin’s name. Which explains why Raffi was so furious when he found out that Irwin had applied, and the recruiter initially rejected her application as “not a good fit.” Irwin was okay with the initial rejection. She wasn’t sure if she really belonged in finance. But Raffi was having none of it. When they connected on the phone soon after, he literally yelled at her. “He was a very passionate person,” Irwin says. “He wasn't angry, he was frustrated, and he said, ‘You have to trust me. This business, this industry needs more people like you.’” Raffi would also tear a strip off of the recruiter, telling him, “There’s a reason I only gave you one name.”

Like many of the people who have come into Irwin’s orbit, Raffi knew her gifts: the empathy, the thoughtfulness, her ability to steer complex human social relationships, her comfort in unfamiliar situations. He learned about these attributes when he recruited her for an internship during her MBA. Alongside the generous benefactor “Maury” Young, the namesake for UBC’s W. Maurice Young Centre for Entrepreneurship and Venture Capital and Research and The W. Maurice Young Centre for Applied Ethics, Raffi supported Irwin with a project to explore the challenges First Nations youth were experiencing engaging in the business sector. They were impressed with her work and proud of the resulting recommendations.

(What’s more, nobody had applied for the internship because it was a 'not for profit' engagement, yet in what Irwin calls a “cosmic twist of fate,” the lead on the posting was Young, who had gifted UBC its new VC research centre. Raffi had asked Irwin to apply because of her background as both a teacher and camp director. She was intrigued and only later found out that she would be working closely with one of the most influential businessmen in the city. Unfortunately, Maury passed away one year after Irwin finished her internship.)

Irwin did end up being invited to interview at BDC for the venture capital job. She flew from Hong Kong to Vancouver for two days, interviewed with five different people and was given a formal offer the afternoon before she flew back.

It goes without saying that the technology industry moves fast. Everything changes. Even the people involved. Ten days into Irwin’s job as an investor at BDC, she was abruptly reminded of this. While attending a board meeting that her boss couldn’t make, she received a phone call which would shift her new VC life into hyperdrive. What was the call about? “Three people, of a team of six, at our office quit,” she recalls. “And it was just gob smacking what my responsibilities became, quite in terms of the portfolio and board positions I immediately inherited. I wasn't even a month into this, so it was an escalated experience in venture because of this unexpected change at the office.”

Irwin’s thirteen years at BDC, as well as her transition to angel investing, have been documented before. Like all VCs she had her hits (Celator Pharmaceuticals’ $1.5B exit) and misses (a forest biotechnology company that went from 200 employees to shutting its doors). She met Olympic gold triathlete Simon Whitfield at a business networking event in 2013, they connected over mutual personal and professional interests, and within a year, they had formed Relentless Pursuit Partners, an angel investing group that became, in some ways, the foundation for her new venture fund. But what hasn’t been detailed is where Irwin and Whitfield’s bond began, and what initially drew Whitfield, essentially a celebrity athlete, to Irwin.

One of Irwin’s colleagues at BDC was Geoff Catherwood, who is currently still a partner for their industrial, clean and energy venture fund. It was Catherwood who invited Irwin to the social event, which involved a 50-kilometre bike ride, barbeque and startup pitch in Deep Cove.

26 guests attended. Irwin, the only woman in the biking group, wasn’t even planning on staying for the pitch, but after a few conversations with the other guests during the ride, she decided to stick around. As she recalls, the CEO pitched, and “it was just tragic.” And what didn’t help was that many of the investors present felt the need to show everyone that they knew more than the entrepreneur. “Like it wasn't a good presentation,” Irwin explains. “He hadn't been coached well in terms of getting prepared, and then it was made worse by a couple of the guys in the group, basically humiliating him.” Irwin’s sympathy gears kicked in, and she attempted to change the situation. She asked questions she knew the answers to just to help the guy. Whitfield appreciated Irwin’s approach; the way she tried to change the dynamic and give the guy a chance. “I like the way you connect with people,” she recalls Whitfield saying.

In some ways, that evening was the launching point for Relentless. It was also an absolutely pure example of Irwin’s capacity for fostering connection in novel environments—what she is known for in investor and startup circles.

The author and tech influencer Kelly Hoey has actually written about Irwin’s approach to networking and relationship building, specifically what she does when meeting with potential limited partners (LPs): “Establishing trust and confidence (including listening for ways to support them in other interests) comes well before the investment pitch,” Hoey wrote in Forbes, of Irwin’s style. In a follow-up piece, Hoey went into more detail: “Irwin's focus is intentional, and experience based: she has no intention on filling her calendar with endless coffee dates or wasting her time by hitting send blindly on emails with pitch decks attached. Rather, Irwin relies on activities that are also building the ‘active living’ brand Relentless Venture Fund is becoming recognized for; activities that are also providing potential investors with unique opportunities to really learn more about the people behind the fund.”

Irwin’s methods seem to be paying off. Within the last year, her fund has announced Vancity as their lead institutional investor, a debut investment into Canary Medical Inc., and recently, a slate of high-caliber advisors and principals, including Alison Twiner, a former Facebook executive, and Todd Humphrey, a SVP with the new Seattle NHL franchise. Also, on her team are Zach Bell, a retired Canadian champion cyclist and Olympian, and Shane Luke, Nike’s senior director, machine learning and AI, who in the past developed their FuelBand.

Beyond the business imperatives, there’s a reason Irwin spends so much time on building real connections. “I think one of the realities of the investment world is people are always pounding their chest and trying to demonstrate how smart they are, how good they are, or what their track record is, who the entrepreneurs are that they have backed, or who they know,” she says. “You have very few moments where you know much about the person outside of the transaction part of the business.”

To change this and the atmosphere at board meetings and dinners, Irwin gets everyone around a room or table to share something that nobody else in the room knows about them—a fun fact or story. “It's fun to share and talk about being human and what your kind of drivers are that people don't know; whether it's you're more left or you're more right brain than they think you are,” she says gleefully. “They think they've got you nailed down and then you just throw them for a loop. For example, I used to be a wedding singer. How about that?”

Photographs by Barbara Jun