jesse.blog

Official Blog of Jesse Friedman





Jesse Friedman


  • If you are unsure of your vision, then talk to yourself



    2–3 minutes

    Giving the agent the ability to reference these passages across my reading and writing will be incredibly useful to me. It will not only help me to articulate, and qualify my own beliefs, it can be really helpful when I’m struggling, or becoming too egocentric.

  • Code for the People — Part One of Two



    10–15 minutes

    I was on sabbatical when Automattic filmed Code for the People — a documentary about the work I’ve dedicated my life to. I kept my promise to stay unplugged, and my ego has yet to forgive me. This essay is how I’m making peace with that: a deconstruction of the film, and an argument for…

  • Better URLs for Calendar Links



    2–3 minutes

    I wanted to share a simple idea — they are often the best — for managing your calendar links. Instead of sending a Calendly or Google Calendar url use your own domain and redirect it. Or buy yourself a shorter domain for redirects. If you’re like me you’re always switching between services and testing out all…

  • Human Authored; AI Inferred



    18–28 minutes

    I cover how a month of building human-centered AI taught me less about machines than about the work only I can do. Twenty years of sales instinct, finally written down because a machine couldn’t run on the same instinct. And how this fed my ideas for a talk in Chicago about what happens when the…

    Jesse Friedman speaking on human-centered AI at Dev/AI in Chicago
  • Chicago Cultural Center



    1–2 minutes

    Chicago, IL — June, 2026

    Black and White Photo of a woman standing in the Chicago Cultural Center
  • Dev/AI/NYC with Hilary Mason & Jesse Friedman



    1–2 minutes

    Join Hilary Mason and Jesse Friedman for a fireside chat on how AI is reshaping creativity, products, and human–computer interaction. Hilary, CEO of Hidden Door, previously founded Fast Forward Labs and served as Chief Scientist at bit.ly. Jesse leads WP Cloud at Automattic, bringing deep expertise in scaling platforms and shaping the future of the web. Expect a candid conversation with practical insights on what’s…

  • Are you able to sit in silence?



    1–2 minutes

    The rush and pressure of modern life are a form, perhaps the most common form, of innate violence.

  • The Future We Choose



    1–2 minutes

    A definite recommend from me. I think everyone, everywhere, of every age should read this book.

    The Future We Choose book cover
  • Accepted to the AI World’s Fair



    1–2 minutes



    I am very proud to announce that Derek Smart and I will be presenting ARC at the AI World’s Fair in San Francisco. Woven In: Building AI Around the Human Work It Should Not Replace Speakers: Jesse Friedman & Derek Smart Talk: How Automattic separated human-authored judgment from AI-inferred context and built ARC around the…

  • Real world colors



    1–2 minutes

    I love collecting colors I find in the real world. There is no competition, Nature is the best designer in the universe. But great colors schemes can be found on the plate at your favorite restaurant, on graffiti on the street, and in a ton of other places. Secret Color Garden is a project I’m…