The Derby Mill Series: Pushing AI to the Limit

How are companies using AI to improve the healthcare journey for consumers? And how will things evolve at the limit, where wearable technology integrates with electronic medical records and medical agentic AI analyzes everything on the fly to issue recommendations and improve outcomes? In other words, what are the implications of everyone becoming equipped with their own superhuman medical agent? 
Seen one way, a superhuman medical agent is what League is aiming to develop. Founded in 2014 in Toronto, League operates an AI-powered healthcare platform for insurance companies and other payers or providers. The platform allows users to manage health benefits as well as their own healthcare. As of early 2026, the company has more than 60 million contracted users and more than a billion consumer interactions annually. Customers include Highmark Health, Manulife, Shoppers Drug Mart, and Medibank. Last year, League gave 100 million healthcare recommendations, of which people clicked through or followed through about 65% of the time.   
In this episode, the Derby Mill team explores where League’s technology might go at the limit with League founder and CEO Mike Serbinis, who aims to expand the company’s capabilities to create a 24/7 infinite care platform—basically, an all-knowing doctor who knows as much as possible about you, your healthcare data, and the science of medicine. It’s a fascinating conversation that sees Sendhil observing how little the medical profession currently knows about optimizing health, or patients themselves, and Ajay challenging Rich to decide whether superhuman AI doctors would be better than having a doctor as a spouse today. (Rich says yes.)   
More on our guest: A serial entrepreneur, Michael Serbinis has also founded and run Kobo, the digital reading company, cloud storage pioneer, DocSpace, and Critical Path, a messaging service. Serbinis is chair of the board for the Perimeter Institute and on the board at the Vector Institute for Artificial Intelligence. He sits on Canada's AI Strategy Task Force.

HOSTS AND PANELLISTS
Mike Serbinis, founder and CEO, League
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, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred

LINKS    
League website. League explainer video
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
00:38 Introductions
01:19 League explainer
01:55 Serbinis explains League
05:28 League’s AI today
08:09 More AI: Content recommendations
12:00 League’s data inputs
13:55 AB testing
19:10 Healthcare archetypes
22:15 Max health v. max engagement
25:30 Business model
27:00 At the limit: Rich 
29:00 Married to a doctor
29:42 At the limit: Sendhil
31:10 Healthcare becomes you
33:37 ROI is huge
38:06 Suzanne: Robot paramedics
42:53 Serbinis responds
46:20 Infinite care team
49:16 Sendhil’s wrap up

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.


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit insights.intrepidgp.com

A response from the Derby Mill team of AI experts to Anthropic co-founder Jack Clark’s recent Substack essay, “AI systems are about to start building themselves.” In the essay, Clark predicts that “no-human-involved AI R&D - an AI system powerful enough that it could plausibly autonomously build its own successor - happens by the end of 2028.” Clark notes: “If that happens, we will cross a Rubicon into a nearly-impossible-to-forecast future."
With that in mind, Ajay tees up a discussion among Rich, Niamh, Sendhil and Suzanne. Is Jack Clark correct that we’re heading toward a future of self-replicating, self-optimizing AI? What are the implications? Does that actually lead to the singularity? And should we, as Rich Sutton says, treat AI the way a parent treats a child, recognizing that mistakes are inevitable? 
“There’s some spookiness being implied here,” Mullainathan says, “about it coming alive and taking over a whole set of decisions we didn’t intend to cede it… and if that’s the case, that freaks me out, too.” 
“The thing that they’re scared about…” says Niamh Gavin. “It’s the fact that you have, in essence, an irreversible positive feedback loop of successive self-improvement cycles, that accelerate it toward what they call a singularity, whereby artificial intelligence exceeds human intelligence and control.”
Are the concerns outlined by Jack Clark warranted? Or are the fears about a harmful singularity overblown? The Derby Mill experts provide their views in our latest episode. 
Finally, another fascinating thread in the episode comes from Suzanne Gildert. “It all comes down to the reward function,” says Gildert. “So there’s this thing that [AI is] still limited by us telling them what to do, because we’re the ones who want something… But that’s eventually going to break because the way the whole reward function in ML works at the moment — it’s all based on our economy… It’s based on people exchanging money for goods and services. All that’s going to break if people can’t work anymore... So that’s why I think we really have to understand what the reward function should be, because the way we’re implementing it now is not going to work beyond the point where [AI] can do all human labour for us.” 
HOSTS AND PANELLISTS
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, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred
LINKS    
The Jack Clark Substack post that triggered the discussion. Jack Clark is on X @jackclarkSF
Subscribe to The Derby Mill Series at our Substack (main site) or on YouTube, Spotify or Apple Podcasts. We post highlights from the show on YouTube.  
Derby Mill is created by the team at Intrepid Growth Partners and produced by Ghost Bureau. 
DISCUSSION POINTS
00:00 Cold open
01:06 Jack Clark post
02:56 Rich Sutton reaction
08:37 Sendhil’s reaction
16:22 Suzanne’s reaction
18:14 Niamh’s reaction
23:48 Wrap up
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.


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit insights.intrepidgp.com

Not just an episode about tax law! In fact, 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 investment round 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.
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, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred
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
28:42 Will AI make litigation obsolete?
35:10 Rich: Code is law
40:55 Ben on code is law
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.


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit insights.intrepidgp.com

When the right answer is a matter of life and death, how do you ensure that your AI systems avoid fatal mistakes? Signal 1 is a software platform for healthcare that functions as a control panel for deployed AI systems in hospitals. Rather than building individual models, Signal 1 focuses on improving the safety, observability and governability of pre-existing AI models used throughout the patient experience. The platform enables health systems to track real-world performance, detect drift and risk, enforce approval workflows, and tie AI predictions to improved clinical and operational outcomes.
Tomi Poutanen is Signal 1’s CEO and co-founder. His earlier start-up, Layer 6, employed artificial intelligence to provide financial services companies with predictive analytics, and was acquired by TD Bank, where Tomi served as chief AI officer. In this episode, Tomi works with the Derby Mill team to discuss the future of healthcare, whether machine learning could make hospitals obsolete, and how to improve the management of systems that include numerous different AI agents working together.  
GUESTS AND HOSTS
Tomi Poutanen, CEO, Signal 1
Ajay Agrawal, co-founder and partner, Intrepid Growth PartnersRichard Sutton, senior advisor, Intrepid Growth Partners, 2024 Turing Award recipient, pioneer of reinforcement learning and professor, University of AlbertaSendhil Mullainathan, senior advisor, Intrepid Growth Partners, MacArthur Genius grant recipient and professor, MITNiamh Gavin, senior advisor, Intrepid Growth Partners, Applied AI scientist and CEO, Emergent PlatformsSuzanne Gildert, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred
LINKS    Signal 1 website
Media on Signal 1 from the Globe and Mail, Betakit and the University of Toronto
Derby Mill series website. Derby Mill is created by the team at Intrepid Growth Partners and produced by Ghost Bureau.
Be sure to catch every episode of The Derby Mill Series by subscribing on the following platforms: YouTube // Spotify // Apple Podcasts // Substack

DISCUSSION POINTS
00:00 Cold open
00:44 Ajay’s tee up
01:22 About Signal 1
04:11 Tomi’s Signal 1 explainer
06:25 Mechanics of Signal 1
07:10 Tomi’s first-order question
08:45 Signal 1’s core value prop
09:29 Patient experience perspective
12:27 Taking MD out of the loop
13:56 Why Signal 1 focuses on AI
18:20 Evaluating AI systems
22:46 Rows
23:13 Ajay’s segue
24:42 Part 2: Signal 1 at the Limit
25:12 Niamh’s sci-fi hospital vision
29:04 Rich questions the premise
31:25 Sendhil: Division of labor for AI
34:50 Tomi: Niamh’s vision is real
38:22 Tomi: Competitive healthcare
43:55 Sendhil: Virtues of randomness
49:44 Niamh: Multiple agent drama
52:54 Tomi’s final remarks

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.


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit insights.intrepidgp.com

OpenClaw, the latest AI chatbot to go viral, has some key differences from ChatGPT, Claude or Gemini. The agentic AI developed by Peter Steinberger is open source and hosted on your own computer. You also can talk to it via messaging apps like WhatsApp. So how does OpenClaw work? What are the implications for the AI industry overall? How will it affect the adoption of artificial general intelligence, or household robots? And what are the security concerns that OpenClaw may trigger? Host Ajay Agrawal explores these issues and more with the Derby Mill team.  
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, CEO, Nirvanic Consciousness Technologies, quantum physicist, co-founder of Sanctuary AI and Kindred

LINKS    
Background on OpenClaw: 
Y Combinator interviews OpenClaw creator Peter Steinberger 
OpenClaw explained
Subscribe to The Derby Mill Series on YouTube, Spotify or Apple Podcasts 

DISCUSSION POINTS
00:00 Cold open 
01:05 What is OpenClaw?
02:08 Difference from chatbots
03:44 OpenClaw’s abilities (Niamh)
04:49 WhatsApp interaction
06:14 Sendhil Mullainathan’s take
09:39 Suzanne Gildert’s take
12:50 Rich Sutton’s take
14:44 OpenClaw security concern
17:27 Niamh on OpenClaw implications
19:05 Final implications: Sendhil

CREDITS
Derby Mill is created by the team at Intrepid Growth Partners and produced by Ghost Bureau. 

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.


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit insights.intrepidgp.com