Not just an episode about tax law! The Derby Mill team’s conversation with Benjamin Alarie, the co-founder and CEO behind Blue J, the fast-growing tax research platform, explores numerous fascinating threads. How will AI change the practice of law and the litigation process? Will trying a case in the justice system be necessary when AI can predict with high accuracy the likely outcome? In other words, will AI make litigation obsolete?
Separately from the discussion about the legal profession, in a section that will be useful for any entrepreneur seeking to tune foundation models to provide the most current results on fast-changing bodies of knowledge, Alarie describes the techniques that Blue J uses to ensure the platform’s responses reflect the latest regulations.
Also useful for entrepreneurs is the discussion on whether specifically tuned, highly specialized models will be more useful to humans than general-purpose LLMs that can provide guidance on a wide variety of topics.
ABOUT BLUE J: Founded in Toronto in 2015, Blue J aims to make the law more transparent and accessible for tax practitioners. In early 2026 the company counted 5,000 businesses in the U.S., United Kingdom and Canada as clients who count on it to provide them with answers on numerous different bodies of tax law. (Intrepid is an investor.) A 2025 Series D valued the company at more than $300 million USD, according to the Globe and Mail.
The platform is able to predict litigation results with greater than 90% accuracy. “Blue J is now the best way to do tax research, flat out, across any other possible technology being deployed today,” Alarie says, arguing that Blue J is better able to provide guidance based on the current state of fast-changing tax law because it licenses proprietary up-to-the-minute regulatory information from taxation organizations in the jurisdictions it services. Just 0.085% of Blue J’s responses are rated thumbs down by clients, and the net promoter score is over 80, with both stats improving as Alarie’s team optimizes the platform.
ABOUT GUEST BENJAMIN ALARIE: In addition to being the co-founder and CEO of Blue J, Benjamin Alarie is full professor and holds the Osler Chair in Business Law at the University of Toronto Faculty of Law. He earned a B.A. at Wilfrid Laurier University, an M.A. and J.D. at the University of Toronto, and an LL.M. at Yale Law School. In 2004 he joined the University of Toronto after clerking at the Supreme Court of Canada. His research focuses on tax law, judicial decision making, and artificial intelligence. He has published extensively and is responsible for coining the concept of the “legal singularity” in 2016.
NUGGETS FROM THE EPISODE
Will AI reduce litigation and increase speed of judicial decisions?
If we have AI agents that are better able to predict judicial decisions, before we go through all of the work to ultimately get a judicial decision, then do we actually need a judicial decision? Ajay and Niamh explore the provocative idea of preventative law.
Will AI make the legal system more complex—or less?
Blue J CEO Benjamin Alarie goes back to the Hammurabi code of laws to make some predictions about how machine learning will affect litigation.
HOSTS
Ajay Agrawal, co-founder and partner, Intrepid Growth Partners
Richard Sutton, senior advisor, Intrepid Growth Partners, 2024 Turing Award recipient, pioneer of reinforcement learning and professor, University of Alberta
Sendhil Mullainathan, senior advisor, Intrepid Growth Partners, MacArthur Genius grant recipient and professor, MIT
Niamh Gavin, senior advisor, Intrepid Growth Partners, applied AI scientist and CEO, Emergent Platforms
Suzanne Gildert, senior advisor, Intrepid Growth Partners, CEO, Nirvanic Consciousness Technologies, quantum physicist
LINKS
Link to Ben’s books: The Legal Singularity. Superjustice.
Alarie’s co-authored article: Legal Order in the Age of AI Agents
Webpage for Blue J. Media coverage on Blue J’s 2025 Series D investment round from BetaKit and the Globe and Mail.
Another podcast featuring Alarie: The Startup CEO Show.
Subscribe to The Derby Mill Series at our Substack (main site) or on YouTube, Spotify or Apple Podcasts
Derby Mill is created by the team at Intrepid Growth Partners and produced by Ghost Bureau.
DISCUSSION POINTS
00:00 Cold open
00:48 Blue J and tax law
02:20 How Blue J works
06:33 Blue J vs. major LLMs
12:30 Managing liability
15:21 Blue J value prop
17:15 The Blue J story
19:36 Blue J operating mechanics
23:02 General purpose vs. special purpose models
28:42 Will AI make litigation obsolete?
35:10 Rich: Code is law
40:55 Ben responds to Rich
45:12 Legal singularity
48:26 Faster settlements?
51:33 Trend toward legal complexity
55:55 Law as learning machine
56:51 Niamh reacts
57:54 Rich reacts
59:50 Suzanne reacts
1:00:57 Ben reacts
DISCLAIMER
The content of this podcast is for informational and educational purposes only and should not be construed as marketing, solicitation, or an offer to buy or sell any securities or investments. The opinions expressed in this video are those of the participants and do not necessarily reflect the views of Intrepid Growth Partners or its affiliates. Any discussion of specific companies, technologies, or industries is for illustrative purposes and does not constitute investment advice. Viewers are encouraged to consult with their own financial, legal, and tax advisors before making any investment decisions.
