Before Signing That SaaS Renewal

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The signals

• Ankit: Clients are buying back 30 percent of the service and doing the rest themselves. His clients started telling him they love the package, but they can get about 30 percent of it now from software they already pay for, and their own team can absorb the other 70. The consequence is not a lost account, it is a repriced one, which meant cutting overhead, which is what sent him looking at his own subscriptions. "It definitely caught my pocketbook".
• Sam: A green run is not proof of useful verification. Six repositories with scheduled research jobs that check each other's work. On the Friday of Labor Day weekend one output was visibly wrong. The failure mode was not a crash: certain research failures came back empty, and as long as one leg of the cascade returned anything the run reported success. "And empty isn't an argument." Ankit had hit the same thing months earlier: "It returned nothing. And that counts because it did something."

The subtractions

• Ankit: HubSpot, and then the habit of buying. The trigger was refusing a year-long contract for a tool they were using a fraction of. He asked AI what open-sourcing the platform would look like, vetted five candidates, and pointed it at his own AWS: Twenty CRM and Chatwoot, company SSO on the front. Built in days, fully transitioned in two weeks against a planned month, and the help desk got faster. His own caveat is the load-bearing one: the speed came from building blocks that already existed.
• Sam: The decision system that made decisions without him. Nine months of building a decision layer into his own second brain, where pre-made decisions sat as lit fuses: unless he acted, the default fired. Then a family emergency took him away for a week and the cascade fired on decisions he had pre-approved under circumstances that no longer held. There was no safety mechanism, because he had not built one. He spent the day before the show defusing every fuse. Ankit's response named it: top-down is not trust, it is authority.

About this episode

The two subtractions run in opposite directions and that is what makes the episode. Ankit removed a vendor and it worked, because the substrate underneath was already his. Sam removed his own automation, because he had built it past the point where he could see whether it was working. Both are the same instruction: look at what is actually running, not at what is supposed to be.

The other thread worth keeping from the tape is where Ankit puts the line between code and models. His first question about any task is whether it is deterministic, or can be mapped until it is; if it can, it is code, every time. AI writes the program, it does not run the business. The worked example is vision insurance, where a prescription crossed with plan tiers produces hundreds of thousands of possible combinations and used to cost twenty minutes of a person's arithmetic per patient. AI learns each new plan and writes the mapping script; the pricing itself is deterministic code. Five to ten minutes saved per transaction, and more to the point, mistakes prevented, which is the kind of thing that kills a small business. He does not use AI for patient information or clinical decisions.

Also on the tape: he gave everyone AI, took it all away, and rebuilt around learning theory instead, chunking concepts and turning them into steps, which is how a 17-step blog-writing process came to exist. His closing hypothesis is that as models improve, the harnesses improve faster, and the scarce skill becomes understanding the concepts well enough to break them down, because the average answer is free now and the value is in the niches around it. Lean, he points out, is not really about removing waste. It is about creating value.

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The newsletter

Issue 68 · Sunday 13 September 2026 · sent on Substack and LinkedIn.

One signal, one subtraction, one analogy, in five minutes. It draws on this episode but stands on its own. Every issue.

The method from this episode is one page with its copy-paste prompt and schema: Empty Isn't an Argument and The Renewal Card, linked under the decision above. Every takeaway.