Software Lead Weekly 
Issue #721, 18th September 2026
This Week's Favorite
The Religion of Speed
5 minutes read.
This is the classic Process Theater, where unprofessional work, lazy work, is being labeled as progress: "People rush through the part where understanding is supposed to happen, then spend ten times longer cleaning up the consequences. The original rushed work gets recorded as “fast.” The cleanup gets recorded as “unexpected.” The rework gets recorded as “iteration.” The confusion gets recorded as “alignment.” The preventable failure gets recorded as “learning.”"
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5 minutes read.
This is the classic Process Theater, where unprofessional work, lazy work, is being labeled as progress: "People rush through the part where understanding is supposed to happen, then spend ten times longer cleaning up the consequences. The original rushed work gets recorded as “fast.” The cleanup gets recorded as “unexpected.” The rework gets recorded as “iteration.” The confusion gets recorded as “alignment.” The preventable failure gets recorded as “learning.”"
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Culture
The Average Vibe Coded Startup
1 minutes read.
My humble effort to help you start the weekend with a smile.
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1 minutes read.
My humble effort to help you start the weekend with a smile.
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Making Startups Powerful
11 minutes read.
Paul Graham on why startups should open up their APIs: "Many companies shrink from that because they dislike the loss of control that comes with it. They want their software to be used only in the way they intended. [...] Especially now that agents are replacing human users. Who knows what they'll want to do?" -- This isn't just a startup problem: the moment agents start calling your platform on someone else's behalf, "intended use" stops being a safeguard and starts being the bottleneck.
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11 minutes read.
Paul Graham on why startups should open up their APIs: "Many companies shrink from that because they dislike the loss of control that comes with it. They want their software to be used only in the way they intended. [...] Especially now that agents are replacing human users. Who knows what they'll want to do?" -- This isn't just a startup problem: the moment agents start calling your platform on someone else's behalf, "intended use" stops being a safeguard and starts being the bottleneck.
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A Lever Made of Agents
14 minutes read.
"The margin story of AI is to replace humans with tokens. The growth story is to use tokens to make new forms of work and human agency economically viable." -- Taylor Pearson's own newsletter example proves the growth side: his agent doesn't just format faster, it routes every reading highlight into live projects, work that never existed as a job to automate in the first place. Which types of new levers you found in your day to day? What about your roadmap?
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14 minutes read.
"The margin story of AI is to replace humans with tokens. The growth story is to use tokens to make new forms of work and human agency economically viable." -- Taylor Pearson's own newsletter example proves the growth side: his agent doesn't just format faster, it routes every reading highlight into live projects, work that never existed as a job to automate in the first place. Which types of new levers you found in your day to day? What about your roadmap?
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Nobody Wants Your Software
8 minutes read.
Worth watching the interview with Yoni Rechtman or reading the key takeaways, since the world still runs on the same fundamentals, but AI unlocks different go-to-market (and product) approaches. Understanding GTM motions will help you think about how to structure the business, product(s), architecture, and org structure.
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8 minutes read.
Worth watching the interview with Yoni Rechtman or reading the key takeaways, since the world still runs on the same fundamentals, but AI unlocks different go-to-market (and product) approaches. Understanding GTM motions will help you think about how to structure the business, product(s), architecture, and org structure.
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Peopleware
Playbook to Manage Up
8 minutes read.
Managing up helps you hold yourself accountable for working on what matters and delivering value. Keeping track of it and reporting on it is a ritual worth practicing to learn how to spot higher value, present it clearly, and open a discussion for more opportunities worth chasing. Danielle Matarasso shares a great framework that you can use (yes, you can also leverage AI): "Managing up just means making sure the people above you know what you’re doing. That’s it. Your boss. Your boss’s boss. The client who pays you. They’re all “up.” Most people never get taught this. So they just assume: I did the work, so people know. They don’t. Your boss doesn’t. Your boss’s boss doesn’t. The other teams don’t. Your clients don’t. NOBODY is keeping track of your work for you. Not because they don’t care, because they’re busy with their own. "
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8 minutes read.
Managing up helps you hold yourself accountable for working on what matters and delivering value. Keeping track of it and reporting on it is a ritual worth practicing to learn how to spot higher value, present it clearly, and open a discussion for more opportunities worth chasing. Danielle Matarasso shares a great framework that you can use (yes, you can also leverage AI): "Managing up just means making sure the people above you know what you’re doing. That’s it. Your boss. Your boss’s boss. The client who pays you. They’re all “up.” Most people never get taught this. So they just assume: I did the work, so people know. They don’t. Your boss doesn’t. Your boss’s boss doesn’t. The other teams don’t. Your clients don’t. NOBODY is keeping track of your work for you. Not because they don’t care, because they’re busy with their own. "
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The AI Competence/Judgement Gap
6 minutes read.
Itamar Gilad has a great insight here: AI narrows the gap between what we can do and what we're actually good at, but it does nothing to close the gap between doing and judging. That mismatch is the real danger zone, producing code, contracts, or specs you're not equipped to evaluate, right when your confidence is highest and your self-awareness is lowest.
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6 minutes read.
Itamar Gilad has a great insight here: AI narrows the gap between what we can do and what we're actually good at, but it does nothing to close the gap between doing and judging. That mismatch is the real danger zone, producing code, contracts, or specs you're not equipped to evaluate, right when your confidence is highest and your self-awareness is lowest.
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Evals as Theory Building
8 minutes read.
"The smoke is real. The fire is not. Smoke rises behind a hill. We do not wait for the flames. We infer them." -- Same logic applies the moment you let an agent optimize against a KPI: the signal survives, the cause doesn't, and the dashboard has no way to tell you which one it's showing. This is why evals on their own won't replace Game Days as a way to own operational rigor. It won't replace talking with customers to see whether they find value in your product beyond what your KPIs tell you.
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8 minutes read.
"The smoke is real. The fire is not. Smoke rises behind a hill. We do not wait for the flames. We infer them." -- Same logic applies the moment you let an agent optimize against a KPI: the signal survives, the cause doesn't, and the dashboard has no way to tell you which one it's showing. This is why evals on their own won't replace Game Days as a way to own operational rigor. It won't replace talking with customers to see whether they find value in your product beyond what your KPIs tell you.
Read it later via Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@marclou: Underrated life advice: Everything that triggers you is a you-problem. You can either stay upset or work on yourself and become better.
- Oren
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.