Brett Colvin, co-founder and CEO of Goodlawyer, knows exactly what it means to go all in. During his keynote speech at this week’s Startup Canada Tour in Calgary, Colvin shared the raw and revealing story behind his leap from corporate law to startup life – a journey marked by grief, grit, and unwavering belief.
Colvin had been a junior associate at a top-tier law firm, seemingly on the fast track. Today, he leads a Calgary-based legal talent platform built for high-growth companies looking for world-class legal support without the overhead of traditional firms.
A Personal Crisis and a Professional Awakening
Colvin’s path to entrepreneurship wasn’t linear. As a kid, he had the instincts – painting houses, and running a high-speed lawn aeration company. But it was a whim that led him to write the LSAT and a desire to appease divorced parents that pushed him into law school.
The pivotal moment came in Vienna during a law school exchange. His father died suddenly from a stroke. “The future I’d been haphazardly contemplating suddenly felt irrelevant,” he said. He returned to Canada with a clearer—but still reluctant—vision: attending law school was the “safest hard thing” he could do. Colvin became a lawyer.
Burning the Boats
At his firm, Colvin quickly gained a reputation as “Mr. Ideas Guy” – a nickname not meant as a compliment. His breaking point came when a partner told him to “keep his ideas to himself.” That was the spark. He quit, moved into his grandmother’s basement, and began building Goodlawyer with every dollar he had. “I knew it was time to burn the boats,” he said—meaning, no fallback plans.
Startups Are Pirate Ships
Inspired by Steve Jobs’ famed pirate flag over the original Macintosh team, Colvin likened startups to pirate ships: scrappy, underfunded, risky, but bold. “If you’re lucky, you find a few brave souls who think you might just make it,” he said.
Not everyone stayed. His original co-founder returned to corporate law within a year. But the ones who remained – Parker Smith, Tom Alvarez, Grant Lahring – were true believers. “Sometimes all it takes is a handful of maniacs who just won’t quit,” he said.
Fundraising, One Call at a Time
In Goodlawyer’s early days, Colvin took on fundraising solo, creating his own investor list and pitching relentlessly. He closed $500,000 from over 25 individuals—many friends, lawyers, and former colleagues. “More than a few said it was the biggest check they’d ever written,” he noted. It wasn’t the million-dollar round he hoped for, but it was enough. “Enough to burn the boats. Enough to keep my pirates. Enough to make my dad proud.”
Build with Belief – and Keep Your People
Colvin’s talk turned practical as he urged founders to value the people around them. “It’s not just about finding great people – it’s about keeping them,” he said. Everyone on the early Goodlawyer team made $48,000 a year. “Communist Goodlawyer wages,” he joked. But they stayed because they believed in the mission.
He closed with a nod to his supporters—his team, investors, Calgary’s startup ecosystem, and most of all, his mom, who even joined their Slack channel at work. “Their belief is what kept me going,” he said. “Because being a founder is hard. It’s lonely. It’s overwhelming.”
The Final Message: Go All In
Colvin’s parting advice was simple but serious: “Eventually, you have to burn the boats. Otherwise, you’ll never get there.” For those still side-hustling their dreams, he urged pragmatism – cut personal costs, build a nest egg – but also boldness. “The opportunity to create something meaningful is worth it.”
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