My October 2026 best business reads roundup

/If You Have To Read One Thing (Well, Make It Two)

Product Management is Still All About Telling Stories – Josh Elman, a16z

+ What AI Didn't Make Cheap - Jaclyn Konzelmann

Demos are almost free now. Working products are not. Because AI made code cheap, but good judgment still doesn't come for free.

/AI & Work

What on earth is going on with AI pricing and packaging? – Elena Verna

I guess no one really knows what they are buying when they are buying a bunch of AI tokens. At least this article treats it for what it is: a product problem.

Strategy as Simulation – Neil Perkin

AI modelling and synthetic audiences are too predictable? There's a concrete risk that they will flatten our strategies into the same mediocre one.

How Retailers Can Reinvent the Digital Flywheel for Agentic Commerce – Boston Consulting Group, Daniel Gospodinov, Lauren Wiener, Khaled Tawfik, Robert Derow, Tanmay Jain, and Coco Anderson

I liked the way they frame this: retailers play a destination game (convincing shoppers to buy directly) and an evaluation game (winning the agent’s selection). The same flywheel supports both games, and each puts different demands on marketplaces, loyalty and personalization programs, and retail media

/Strategy & Product

Some final words on Foursquare – Dennis Crowley

+ Some lessons learned from Foursquare – Steven Rosenblatt

After 17 years, Foursquare was acquired, with a $0 outcome for equity holders. These two reflections try to find hard lessons in the ride. There are many, at different levels, but the one that sticks with me is: don't fall in love with your company. Persistence has an opportunity cost.

/Bonus:

Thom Yorke telling Harry Styles that songwriting "is not divine intervention or anything like that. It's like you got to show up in order to find these things. You have to learn to accept the months of imposter syndrome (...) and then you'll pick up your notebook and there will be one line in it that sets you off. But the point is that you showed up, because it's really easy not to show up. It's the small acts that end up being the big acts".

Full video here: https://youtu.be/8N3PmjcvYtY?si=_WwHbUyfEzh1ltQE

Originally shared as a LinkedIn post. Check it out here.

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My September 2026 best business reads roundup