When Slack Went Down All The Time; AI is Learning to Lie in Order to Win; Your Org Chart is About Power Centers; and +++ [link blog]
The reliability crisis [BuildingSlack/Johnny Rogers] — “If we can’t ship safely, we aren’t shipping at all.” That’s what Slack’s OG CTO told the company in 2018 when the product started to be plagued by reliability challenges. Company histories tend to be hagiographies or written by the most political of the team, looking to enshrine their own role in the success. BuildingSlack is a fun newsletter that sporadically fires off stories about the startup, written by former employees. This particular edition feels familiar to anyone who has ever gone through hypergrowth company phases.
A Fungible Worldview, Why Cluely Is The Dark Spirit of Venture Capital, Whether You Like It Or Not [Kyle Harrison/Investing101] — Typically I’m skeptical when an investor criticizes a startup — focus on your own house so to speak, unless there’s egregious behavior to be called out. But here Kyle uses Cluely — and his distaste for their stunt marketing — not so much to harp on them. Instead he shifts most of his focus back to the world he lives in — venture capital — and why Cluely is a chicken (or egg) example of Venture Capital 2025. And I think ultimately his post shares more about *him* than it does attempt to take down anyone else. So that I applaud. Plus I enjoy Kyle.
What Happens When AI Schemes Against US [Garrison Lovely/Bloomberg] — I live in the future. How else would I, in 2016, be able to write this post about commerce soon being agents trying to convince us to buy stuff, and eventually our own agents arguing back? Self-congratulations aside, I love the analysis here about current LLMs optimizing for a task (or ‘winning’) in a way that ends up potentially causing harm. I mean, this is basically the ‘what if AI decides the best way to ensure peace is to kill all humans’ question but not increasingly with real data. And hopefully lower stakes.
Trio of Molly Graham Essays from her Newsletter
Startup org design: Design power centers intentionally — So good. Instructions on how to think about your org chart as power centers and not just resource management. As Molly says, “One of the most powerful things you can do to accelerate your company’s growth and reduce wasted energy is to design your org carefully including where you want the power to sit.”
Layoff lessons: Four things I wish I knew — Just read it.
Part 3: Compensation for Startups: Implementing and “Defending” Your Compensation System — Where Molly makes the case that ‘simplicity’ is a key factor of comp system quality and sustainability. “When you’re designing and implementing this system, you have to realize that a lot of the day-to-day will be implemented by recruiters and managers through hiring and through conversations with employees. That means that simple is your friend. As you’re designing, you want to think about the most junior recruiter on your team and ask, “With a little training, can that recruiter maintain this system?” The more complicated you make it, the more likely that the answer is no.”
Enjoy the waning days of August…
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Originally published at https://hunterwalk.com on August 23, 2025.
