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  1. Google's open-source Gemma launch failed to account for community infrastructure, creating a poor first impression with key stakeholders.

  2. On a personal note

    Reflecting on a transformative period of recovery, exploration, and the decision to build something new in the age of AI agents.

  3. When risk-averse leadership replaces visionary founders, the focus shifts from innovation to asset protection.

  4. People aren't inspired by a hero's journey of suffering—they're inspired by movement and momentum.

  5. It's hard to admit this

    My first company failed because I tried to solve everything at once, lacked product-market fit, and didn't listen to users.

  6. I shut down Spine

    After co-founder disagreement, shutting down the project in an evening freed me to find a new direction within a week.

  7. In 2010, I left a great role to build a product focused on fair algorithms.

  8. A tribute to Allen Romero—a fellow founder who persevered for ten years on a mission to bring people closer together IRL.

  9. Compete with yourself, not others.

  10. If you manage a work queue, you already know feature prioritization.

  11. Countless companies try to kill the spreadsheet.

  12. You have a cultural problem.

  13. A decade of hustle culture experiments that made me no more successful—just less enjoyable to be around.

  14. Thoughts on the Expensify email blast—I agree with the message but object to the channel.

  15. We're not going back

    Written March 2020—the remote work shift has already happened.

  16. Algorithmic bias is a known problem.

  17. Two years ago, Lime was a great addition to guacamole, rather than a sidewalk.

  18. The top 10 tech companies spent $4.7 billion on healthcare acquisitions since 2012.

  19. Trump blames Amazon for the Postal Service losing billions.

  20. Autonomous cars will eat short-haul air travel.

  21. The next land rush might not involve land.

  22. Would you be comfortable buying glasses sight-unseen?

  23. Americans spend 29.6 billion hours a year commuting.

  24. Amazon is buying Whole Foods for $14 billion.

  25. Tyrant in the code

    AI isn't biased because it's evil.

  26. Dear President-Elect,

    You’ve won.

  27. Apple's slow-squeeze strategy against Google's search revenue is becoming clear.

  28. Understanding that reality is constantly changing and absolutes are rare; learning to accept uncertainty.

  29. Accessibility is a huge problem in the tech world that we don’t talk enough about.

  30. The story of why Social Media couldn’t scale to provide us all a voice.

  31. You’re too good for clickbait, so you should read this.

  32. On criticizing Mayer

    There isn't a pundit criticizing Mayer that has ever managed a turnaround at a large company.

  33. More toxic than vanity metrics is the celebrity worship within the entrepreneurial community.

  34. When you read advice from folks like Evan Williams and others who have a well-known brand, it’s important to step back and realize that…

  35. I'm not a fan of many models beyond: 1) talk to people, 2) build something, 3) try said something.

  36. Three Steps

    I take a lot of steps every day.

  37. Almost There

    The best is yet to come.

  38. It’s their fault.

    Us and them.

  39. Being Grateful

    Baby steps to happiness.

  40. A Life Through Glass

    After spending some time with Glass, I wanted to address questions I’ve received, provide tips for new Glass owners, and share some of the shortcomings of the alpha device.

  41. Starting with Hello

    Learning to start cold conversations.

  42. Posts and photos require more subtle notification methods.

  43. Please, for the love of God or in spite of Her, stop reading and writing articles about the “Ten Best Ways to Launch a Company,” “Marketing Secrets of the Super Rich,” or the “Seven Biggest Failures You Never Knew About.

  44. 2am and there was a fire in my downtown San Francisco apartment complex.

  45. We’ve all sat across from someone who’s in a bind and ends a story with, “What do you think I should do?

  46. My Mother

    I’m thankful for the fact that when I couldn’t speak, she understood me.