Hey there Legal Rebels! 👋 I'm excited to share with you the 27th episode of the 2025 season of the LawDroid Manifesto podcast, where I will be continuing to interview key legal innovators to learn how they do what they do. I think you're going to enjoy this one!
If you want to understand how military discipline translates into disruptive legal innovation and the challenges of building AI tools that democratize access to justice, you need to listen to this episode. Alistair is at the forefront of challenging traditional legal gatekeepers and has a unique perspective on making legal services more accessible through technology.
Building Legal AI Without Permission
Join me as I interview Alistair Vigier, co-founder of Caseway, a legal AI platform that's shaking up the Canadian legal establishment.
In this compelling podcast episode, Alistair shares his unconventional journey from military service through various entrepreneurial ventures to founding one of Canada's most talked-about legal AI companies. He dives deep into how his military background instilled the discipline to "think less and do more," driving him to build practical solutions rather than getting paralyzed by overthinking. Alistair also reveals the dramatic story of being sued by CanLII for web scraping public court decisions, and how this legal battle became a catalyst for broader conversations about AI and access to justice.
His stories and insights demonstrate a fearless approach to legal innovation, including partnerships with the University of British Columbia to build what he believes will be one of the first legal LLMs, and ambitious plans to automate court form completion across thousands of counties. This episode is essential viewing for anyone interested in the intersection of military discipline, entrepreneurship, and legal technology disruption.
The Skinny
Alistair Vigier, co-founder of Caseway, brings a unique military-forged perspective to legal AI innovation. Growing up in a Navy family and serving seven years in the Canadian Army, including special forces training, Alistair developed a discipline-first approach that prioritizes execution over endless planning. After being injured during Olympic security training and transitioning through journalism, real estate investment, and law firm management, he discovered his passion for legal technology.
His company Caseway has grown to 4,000 users in just eight months by offering legal research at $49/month versus competitors' $200-300 pricing, while providing contract review and creation for free to gather user feedback. The company made headlines when CanLII sued them for web scraping public court decisions, a legal battle that highlighted broader issues about AI access to public legal information. Alistair's vision extends beyond current offerings to include bespoke AI agents trained on firm-specific documents, automated court form completion, and partnerships with UBC to develop a dedicated legal LLM.
Key Takeaways:
Military discipline taught Alistair to "think less and do more," focusing on daily task completion rather than getting overwhelmed by long-term goals
Caseway differentiates through aggressive pricing ($49/month vs. $200-300 for competitors) and user-driven product development rather than massive advertising spend
The company deliberately avoids venture capital to maintain flexibility, instead relying on angel investors and substantial Canadian government grants.
Web scraping public court decisions is legal and essential for democratizing legal AI, as court decisions are taxpayer-funded public information
The CanLII lawsuit generated massive media attention but ultimately went nowhere, with the forensic audit finding no copyright violations
Building a custom legal LLM is necessary to overcome limitations of general-purpose models like ChatGPT, including hallucinations, bias, and token size restrictions
Government funding for legal AI is substantial because 70% of people in the justice system lack legal representation, creating massive taxpayer costs
The goal is to make legal services more affordable and transparent through flat-rate billing enabled by AI efficiency
Notable Quotes:
"I did not really want to continue on as a psychologist. Statistics was interesting, but again, didn't really want to pursue it. So I was looking at either med school or law school, and I'm not very good around blood and stuff." - Alistair Vigier (07:49-07:59)
"When you're in the military, it's like you're going to go and shoot guns now. Now you're going to climb a mountain. Maybe you're going to jump out of a plane. Now you're going to do this. And you don't really have to think about anything. And you move towards a goal." - Alistair Vigier (09:27-09:41)
"I actually think that's a massive advantage with entrepreneurship. Because if you're sitting around and you're like, oh, how are we going to become a billion dollar company? How are we going to beat this company? You're going to get scared real quick." - Alistair Vigier (09:58-10:10)
"It's really hard to change law when you're in it. And that was something I always had a hard time with the law society, with all the regulations, with the lawyers being so afraid of losing their licenses or getting in trouble." - Alistair Vigier (22:22-22:34)
"We got sued by CanLII, and it was very, very bizarre. We had actually reached out to them and offered to do a partnership deal, and we wanted to pay for the content. And they responded with just suing us." - Alistair Vigier (35:05-35:15)
"Zero. It's all organic. It's all media. I think it's a big mistake at this time to throw massive money. There's a lot of companies that have raised venture capital and they're pouring it into pay-per-click." - Alistair Vigier (27:33-27:43)
"When you pump someone full of steroids or a company full of steroids, there's going to be two outcomes. Either they're going to die of a heart attack or they're going to win the competition." - Alistair Vigier (28:24-28:32)
"I want to help solve the access to justice problem, try and get that percentage down. I actually want more people to hire lawyers. I want to make it more affordable to hire a lawyer." - Alistair Vigier (53:17-53:26)
Clips
From Special Forces Aspirations to Unexpected Injury
From Ambition to Adversity: The Turning Point in Alastair’s Military Career
Martin’s Irony: Lawyer’s Paradoxical Relationship with AI
Military Mindset: Focus on Execution, Not Overthinking
Alistair's journey from military service to legal AI disruption exemplifies how unconventional backgrounds can drive innovation in traditional industries. His military training instilled a focus on execution over analysis paralysis, while his diverse experiences in journalism, real estate, and law firm operations provided insights into inefficiencies ripe for technological disruption. The CanLII legal battle, rather than deterring innovation, became a catalyst for broader conversations about AI access to public legal information and positioned Caseway as a champion for democratized legal technology.
What's particularly compelling is Alistair's strategic approach to funding and growth. By rejecting traditional venture capital in favor of angel investors and government grants, Caseway maintains the flexibility to pivot based on user feedback rather than investor thesis. This approach, combined with aggressive pricing and organic growth, demonstrates how legal AI companies can build sustainable businesses without the high-stakes pressure that often leads to premature scaling or pivoting away from core user needs.
Closing Thoughts
As someone who's been in the legal tech space for years, I find Alistair's approach both refreshing and strategically sound. His military background brings a unique perspective to an industry often paralyzed by risk aversion and regulatory fear. The willingness to challenge established players like CanLII, while controversial, highlights the tension between traditional legal gatekeepers and the democratizing potential of AI technology.
What excites me most about Caseway's trajectory is the focus on solving real access-to-justice problems rather than just creating another legal research tool. The vision of enabling flat-rate legal services through AI efficiency could fundamentally reshape how legal services are delivered and priced. When lawyers can complete complex work in a fraction of the time while maintaining quality, everyone wins - lawyers earn more per hour, clients pay less overall, and the justice gap begins to close.
For our Legal Rebels community, Alistair's story demonstrates that successful legal innovation often comes from outside traditional legal circles. His combination of military discipline, entrepreneurial experience, and genuine passion for democratizing justice shows how diverse backgrounds can drive meaningful change in our profession. The future of legal practice belongs to those who can execute quickly, adapt based on user feedback, and maintain focus on solving real problems rather than getting caught up in industry politics.
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