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John Collison: evaluation

10 Mar 2026 Cheeky Pint Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

“Obviously, good companies did this before AI, continuous process improvement, and it feels like that is the best thing to do.”

— John Collison

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Speaker
John Collison
Attribution
Verified speaker
Claim type
evaluation
Recorded
10 Mar 2026
Publisher
Cheeky Pint

Transcript context

…Hear me out, though, in this, because if you said, "I want to make the legal department more productive, so I want to make it easier to do red lines," and you optimize that. But why is the contract there? What is it for? If you're, for example, onboarding a supply chain vendor and you have hundreds of them, you might actually say actually making an abstract technology for your legal department to red line contracts more efficient is actually a harder, more general problem than for your supply chain vendors, because you might actually have very rigid rules around your supply chain. Let's say you're a CPG company, and you might actually have very specific saying, "Look, if you want to work with us, here's our core legal terms, here's the axis of independence." If you want to make an AI agent to automate that contract, that's actually a much more narrow problem domain that doesn't require general purpose redlining technology. In fact, if you reduce it, you could say, "Well, there are 10% of our suppliers where we let them negotiate their contract, but only for this spend." Let's have them go through our legal department. The rest, let's do it all with AI. My point on it is, if you look at it through the lens of an end-to-end business process, you can turn science into engineering. I think solving legal through AI, that's a science problem. This is my point, though, which is I think people are going through department by department. Similarly, there's not a person accountable for that end-to-end process. The more you can narrow the domain that you're solving with AI, the more you can build a harness or a scaffolding with existing technology to actually fully automate it. My hypothesis is most companies just aren't set up that way. That's just not how we're organized. As a consequence, we're all optimizing our silo. We're all just installing Copilot. Copilot is great, by the way. I didn't mean to insult it. But it's not actually like... But it's incremental. To be fair, that's the thing we're doing. Obviously, good companies did this before AI, continuous process improvement, and it feels like that is the best thing to do. I think what you're saying is there's no such thing as an AI lawyer. Instead, there's improving your commercial contracting. That is a thing that you can— Even more narrowly, pick one domain of commercial contracting and solve that. I actually think those are truly solvable. I think the companies that really think about their business that way, I think they can see the value. Again, I'll go back to the immaturity of the applied AI market is probably one of the bigger barriers right now. My hope is that as the applied AI market matures over the next few years, we'll see a step change in productivity.…

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