Software Lead Weekly

How Brian Chesky Is Redesigning Airbnb for the AI Era (Video)
83 minutes read.

Brian Chesky is such a great thinker. You can see it in the examples he gives, the idols he follows, and the principles he shares to build a narrative. You need to listen to this conversation between Brian and Patrick O'Shaughnessy if you want to understand how your career should shift, how your team should transform, and how your company should be structured.

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vibeCodedAppSecurity
1 minutes read.

My humble effort to help you start the weekend with a smile.

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I Shipped a Facebook Feature So Fast Sheryl Sandberg Called an Emergency Meeting to Stop Me
7 minutes read.

Michael Novati puts an interesting question when it comes to delivering features with AI: "If an engineer doesn’t sweat through the weekend gluing the raw UI to the CDN signing logic, will they have the courage to stand in front of the COO and CEO of a major company and argue for a launch? Or does outsourcing the tedious, manual glue-work also accidentally rip out the human ownership that makes engineers brave enough to defy their own leadership?" -- I think the answer is still yes. It's rare to find engineers with a strong ownership mentality that look for the "why" behind a no and find solutions to push through the inertia of slowing down.

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Everything Is Recorded Now
7 minutes read.

"The historical bottleneck for verbal cultures was that the important context happened in conversation and then evaporated. When AI can attend every meeting and synthesize what happened, verbal culture finally scales. That’s not to say that written culture companies won’t benefit too: giving AI access to thoughtful writing is obviously also a good way to get it up to speed on what matters in the company. But, overall, I think AI is going to promote and enhance verbal culture disproportionately." -- Written culture will benefit more, as the value of written culture is not the fact that you have artifacts in writing, but rather people practice clearer thinking. AI needs that more (insights, "taste") than it needs raw information.

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Another Bad Article With the SaaS Is Dead Narrative
7 minutes read.

"The agentic era is assembling a new infrastructure stack and it is being assembled by incumbent software companies, not AI startups. [...] None of these companies invented these positions in the last 18 months. All of them built the underlying infrastructure over years or decades, for reasons that had nothing to do with AI agents. The agentic era arrived and found the infrastructure already in place. [...] Betting against software in the AI era is betting against the people who built the infrastructure the AI era runs on. Good luck with that." -- Sammy Abdullah is spot on here. The infrastructure enables deterministic (and cheap) workflows while providing the context for LLM-driven exploration.

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Do You Know What You Are *Really* Selling? (As a Senior Leader)
4 minutes read.

Understanding what you sell is about the feeling you create when others interact with you or your product. Worth reading the chat conversation to see how Shreyas Doshi challenges his thinking and Claude's responses: "some people tell you if you can't encapsulate it in 1 word, then you've got it wrong. but they're just trying to feel smart (or are otherwise not clear enough thinkers i.e. they have never thought about how the limitations of the english language get in the way)."

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Water Town: The Agent Swarm Data Stack
8 minutes read.

Building a community of agents with specialized roles and context is not much different from how we handle it now (humans). Should we mimic known structures or leverage new traits (agents don't sleep or get bored) to find different levers?

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@rakyll: Dealing with scale under a ton of ambiguity is hard. Decision making and execution slows down with success. It’s painful but is also nature’s greatest equalizer.

@shreyas: It took me 15 years of being extremely busy and super-stressed in my job to realize that more skill gives you back more time, energy, joy. Before that, I was chasing more skill just for career advancement. I then saw how leveraging skill for more time, energy, joy is amazing.