jesse.blog

Official Blog of Jesse Friedman





Jesse Friedman


  • 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…

  • Why



    1–2 minutes

    AI should be empowering, not fear inducing. Period. Are we there yet? No, I don’t think so. One of my core philosophies around the use of AI is that it should empower me to focus on what makes me special, what skills I can cultivate, what talents I can enhance. For example, I want AI…

  • Adversity is a terrible thing to waste



    1–2 minutes

    In this episode of the Daily Stoic, Ryan Holiday interviews Will Guidara, author of Unreasonable Hospitality — read it if you haven’t. I paused when Guidara said: “Adversity is a terrible thing to waste.” It’s a well-formed phrase for an idea I’ve been turning over for a while. You see, lately, I’ve been thinking about…

  • Half Blind



    1–2 minutes

    Most art forms are shaped by the artist in sight of the whole. Step back from a large sculpture or a massive mural. Compose a song and play it back in minutes. But a book? You can never step far enough back to take it all in at once. Long-form storytelling may be the only…