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Google's open-source Gemma launch failed to account for community infrastructure, creating a poor first impression with key stakeholders.
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Reflecting on a transformative period of recovery, exploration, and the decision to build something new in the age of AI agents.
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When risk-averse leadership replaces visionary founders, the focus shifts from innovation to asset protection.
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People aren't inspired by a hero's journey of suffering—they're inspired by movement and momentum.
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My first company failed because I tried to solve everything at once, lacked product-market fit, and didn't listen to users.
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After co-founder disagreement, shutting down the project in an evening freed me to find a new direction within a week.
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In 2010, I left a great role to build a product focused on fair algorithms.
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A tribute to Allen Romero—a fellow founder who persevered for ten years on a mission to bring people closer together IRL.
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Compete with yourself, not others.
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If you manage a work queue, you already know feature prioritization.
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Countless companies try to kill the spreadsheet.
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You have a cultural problem.
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A decade of hustle culture experiments that made me no more successful—just less enjoyable to be around.
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Thoughts on the Expensify email blast—I agree with the message but object to the channel.
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Written March 2020—the remote work shift has already happened.
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Algorithmic bias is a known problem.
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Two years ago, Lime was a great addition to guacamole, rather than a sidewalk.
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The top 10 tech companies spent $4.7 billion on healthcare acquisitions since 2012.
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Trump blames Amazon for the Postal Service losing billions.
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Autonomous cars will eat short-haul air travel.
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The next land rush might not involve land.
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Would you be comfortable buying glasses sight-unseen?
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Americans spend 29.6 billion hours a year commuting.
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Amazon is buying Whole Foods for $14 billion.
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AI isn't biased because it's evil.
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You’ve won.
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Apple's slow-squeeze strategy against Google's search revenue is becoming clear.
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Understanding that reality is constantly changing and absolutes are rare; learning to accept uncertainty.
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Accessibility is a huge problem in the tech world that we don’t talk enough about.
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The story of why Social Media couldn’t scale to provide us all a voice.
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You’re too good for clickbait, so you should read this.
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There isn't a pundit criticizing Mayer that has ever managed a turnaround at a large company.
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More toxic than vanity metrics is the celebrity worship within the entrepreneurial community.
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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…
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I'm not a fan of many models beyond: 1) talk to people, 2) build something, 3) try said something.
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I take a lot of steps every day.
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The best is yet to come.
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Us and them.
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Baby steps to happiness.
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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.
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Learning to start cold conversations.
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Posts and photos require more subtle notification methods.
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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.
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2am and there was a fire in my downtown San Francisco apartment complex.
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We’ve all sat across from someone who’s in a bind and ends a story with, “What do you think I should do?
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I’m thankful for the fact that when I couldn’t speak, she understood me.