Co-Founder of Blogger, Twitter, Medium, and Mozi — The Art of Pivoting, Strategic Quitting, and More

In this live Austin conversation with Tim Ferriss (opened by Kevin Rose), Ev Williams traces his arc from a Nebraska farm to founding Blogger, Twitter, and Medium, and now Mosy. He argues that strategic quitting and recognizing opportunity cost matter more than the celebrated myth of pure perseverance, using Odeo's pivot into Twitter as the central example. He champions the book 'Why Greatness Cannot Be Planned,' explaining that truly novel creation can't be plotted toward a fixed goal. Williams also opens up about underinvesting in relationships, learning to 'feel your feelings,' and the personal-growth work (therapy, psychedelics, meditation, the Hoffman Process) that reshaped him after being fired from Twitter. Mosy, he explains, is his attempt to build a real social network focused on in-person connection rather than performance, media, or advertising.

• Williams concluded Odeo wasn't on a great trajectory and told investors he wanted to stop, even though the company wasn't dead, because he wrote a convincing pivot strategy doc and then realized he simply didn't want to do it.
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• He cites the idea that 'it's okay to quit' as underappreciated, pointing to Annie Duke's book 'Quit' and arguing people underestimate opportunity costs far more than sunk cost.
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• Williams reveals he stepped down from running Medium a couple years ago because he realized he was continuing out of ego, pride, and others' expectations rather than genuine drive.
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• He names getting fired from Twitter as his biggest perceived failure, describing being devastated, but in hindsight says he's probably far happier than he would have been otherwise.
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• Mosy's wildest-dreams vision is to be a ubiquitous social network like Facebook once was, but designed for real relationships, not media, advertising, performance, or status-building.
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• The Mosy team built a whole system of customizable digital business cards with fonts and colors, then killed it, recognizing it was noise compared to the core utility of knowing where friends are.
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• Reading 'Why Greatness Cannot Be Planned' while running Medium gave Williams a deep sense of relief, validating that he'd always treated products as a creative process you figure out as you go.
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• Williams credits exercise and daily meditation, started seriously in early COVID around turning 50, with dramatic life improvement.
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• Williams' first internet product, in 1994, was a two-hour VHS tape filmed in his basement explaining how to FTP by terminal and use Usenet and Gopher, with only about three minutes on the web.
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• Odeo was a podcasting company Williams co-founded in 2005; Apple released podcasts in iTunes that summer, blindsiding the team and obsoleting months of their work overnight.
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• Twitter emerged from an internal Odeo hackathon when the company had roughly 12 to 14 employees, with Twitter informed by Jack Dorsey's prior work on courier and status systems.
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• Twitter hit its inflection point at SXSW 2007 in Austin, where the team paid about $11,000 to put a screen in the conference hallway streaming tweets instead of taking a trade show floor.
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• Williams strongly recommends 'Why Greatness Cannot Be Planned: The Myth of the Objective' by Ken Stanley (an early AI researcher) and a co-author.
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• Williams calls the Hoffman Process the best thing he's done for personal growth, describing it as '20 years of therapy in a week': a week-long Petaluma retreat where you surrender your phone and can't share your last name or job.
  00:36:36
• Williams says he is 'long psychedelics' for their therapeutic ability to help people, hoping they remain generic rather than patented.
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• He's been reading 'The One' by Henry Poss, about monism, the idea that the universe is one thing and separation is an illusion, recommended by his Obvious Ventures partner James Joaquin.
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• Williams uses the meditation app The Way, created by Henry Shukman, which Kevin Rose sent him during its beta.
  00:41:49
• Williams admits he watches a lot of YouTube, gravitating to music-creation content and quantum physics videos, following his curiosity despite no formal physics background.
  00:48:39

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