Books, apps, and tools people actually name.

recommends / book

“Timeless Way of Building by Christopher Alexander. He wasn't really an architect, but he, I think, taught in Berkeley. He has these interesting thoughts about building things and he focuses on buildings and towns and these kinds of spaces, but I think there's a lot of things that are also interesting for building software. The other book that I like is the Zen and the Art of Motorcycle Maintenance, because it also talks about the quality of things and I think that's one of the main themes of the book. The thing is also that quality is so hard to define. If you actually start thinking about it, it's like, how do you define it? It's really hard to pin down, but it's like when you try something or see it, then you know if it's quality or not.”

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recommends / book

“I will plug some books that have nothing to do with the internet or software or tech, but have been the most informative or instructive books for me I think in my career as a product person working on software, which are books about architecture and urban planning. The reason why I find this field so fascinating is because for thousands of years, people have been figuring out how to build spaces that help people interact with each other and build good spaces to occupy. We've only been doing this for, going back to the Kevin Kelly thing, for basically the blink of an eye on the internet and in the digital realm. There's one book in particular by an architect named Christopher Alexander who sadly just passed away earlier this year. He wrote this book in the '70s. It's called The Timeless Way of Building. This is the book that I recommend to the most people I have. I buy it in bulk and I just give it away to people. The basic premise of the book is that in the '70s, we had just gone through a couple of decades of just mass produced cookie cutter suburban house development in the US. His premise was like we've basically just lost the plot on this. No one likes living in these houses. If you think about why these houses all feel bad to live in, it's because the people building the houses now for the first time ever are different than the people living in the house. It's these developers, these real estate developers, these big companies, mass producing these houses. But for thousands of years, we've figured out what makes a good house. The people building the house are the people living in it and they get that, but now the incentive structure got changed and they messed everything up. I think there's a really interesting parallel there with the internet, specifically how the last decade or so has played out, where the people building the spaces that we occupy are operating under a very complicated incentive structure and it's leading to these suboptimal user experiences. This is what we work on at Substack. This is what I think is fun to work on right now. If you're working on something like this, I would highly recommend The Timeless Way of Building by Christopher Alexander.”

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