#800: Ev Williams — The Art of Pivoting (e.g., Odeo to Twitter), Strategic Quitting, The Dangers of Premature Scaling, Must-Read Books, and More
Episode
63 min
Read time
2 min
Topics
Relationships, Investing, Startups
AI-Generated Summary
Key Takeaways
- ✓Strategic Quitting Framework: Quit when ego and pride drive persistence rather than genuine belief in the vision. Williams quit Odeo despite raising VC funding because he lacked personal conviction, even though metrics showed modest growth. Opportunity cost of continuing outweighs sunk cost fallacy.
- ✓Innovation Without Objectives: Planning works for formulaic goals like running marathons but fails for unprecedented innovation. Book "Why Greatness Cannot Be Planned" argues breakthrough products emerge from trying new approaches rather than plotting rigid roadmaps. Evolution succeeds through experimentation without predetermined endpoints.
- ✓Premature Scaling Trap: Medium failed by attempting to build an entire publishing ecosystem simultaneously instead of perfecting core features sequentially. With more than handful of employees, internal pressure to show progress forces premature feature expansion. Eighty percent of startup advice should be do less.
- ✓Twitter's Accidental Discovery: Twitter emerged from Odeo hackathon where twelve employees explored text messaging alternatives to podcasting. Initial version showed only latest status update, not full feed. South by Southwest 2007 hallway screen placement for eleven thousand dollars created critical mass among early adopters.
- ✓Relationship Investment Shift: Williams recognized decades of underinvesting in relationships while overinvesting in business and information. Mosey addresses this by enabling city-level location sharing with trusted contacts only, requiring mutual phone book presence. Privacy controls allow selective plan visibility rather than broadcasting to all contacts.
What It Covers
Ev Williams discusses pivoting Odeo to Twitter, strategic quitting versus perseverance, premature scaling mistakes at Medium, building Mosey for real-world connections, and embracing ambiguity over rigid planning in innovation.
Key Questions Answered
- •Strategic Quitting Framework: Quit when ego and pride drive persistence rather than genuine belief in the vision. Williams quit Odeo despite raising VC funding because he lacked personal conviction, even though metrics showed modest growth. Opportunity cost of continuing outweighs sunk cost fallacy.
- •Innovation Without Objectives: Planning works for formulaic goals like running marathons but fails for unprecedented innovation. Book "Why Greatness Cannot Be Planned" argues breakthrough products emerge from trying new approaches rather than plotting rigid roadmaps. Evolution succeeds through experimentation without predetermined endpoints.
- •Premature Scaling Trap: Medium failed by attempting to build an entire publishing ecosystem simultaneously instead of perfecting core features sequentially. With more than handful of employees, internal pressure to show progress forces premature feature expansion. Eighty percent of startup advice should be do less.
- •Twitter's Accidental Discovery: Twitter emerged from Odeo hackathon where twelve employees explored text messaging alternatives to podcasting. Initial version showed only latest status update, not full feed. South by Southwest 2007 hallway screen placement for eleven thousand dollars created critical mass among early adopters.
- •Relationship Investment Shift: Williams recognized decades of underinvesting in relationships while overinvesting in business and information. Mosey addresses this by enabling city-level location sharing with trusted contacts only, requiring mutual phone book presence. Privacy controls allow selective plan visibility rather than broadcasting to all contacts.
Notable Moment
Williams describes getting fired as Twitter CEO after two years as his biggest perceived failure, devastating at the time due to ego and identity attachment, but retrospectively recognizes he avoided years of unsuitable work while retaining equity ownership.
Episode Transcript
Hey, folks. Tim here. My best selling card game, Coyote, which I made with the amazing team at Exploding Kittens, just won the Pop Insider best geeky game of 2025 and also best stocking filler in the made for mom's toy awards twenty twenty '5. It is on sale everywhere. It's cheap. It's fast to learn. It has 4.8 stars out of five. People are loving it. Coyotegame.com will take you to all the retailers, but you can find it everywhere. It is a game of thinking fast and laughing faster. Think charades meets hot potato meets a bunch of brain fun. It's good for your head. It's perfect for families with kids age 10 or adults who are kids at heart or don't take themselves too seriously. A lot of adults love this game. And as I said, it's available everywhere. Amazon, Walmart, Target, 8,000 plus retail locations, you name it. So please check it out. I loved making it. People are really enjoying it. It has 300 or 400,000,000 plus social views of gameplay online. And try it. Enjoy it this holiday season. Check it out, coyotegame.com one more time. That's coyotegame.com or anywhere you buy your games. Now back to the episode. Hello, boys and girls, ladies and germs. This is Tim Ferris, and welcome to another episode of the Tim Ferris show, where it is my job each interview to deconstruct world class performers, to tease out the habits, routines, influences, and resources that you can apply to your own lives from people from every discipline imaginable ranging from entertainment to the military, to technology and beyond. Today, my guest is Ev Williams and what a story he has. Ev is the cofounder and chairman of Mozy, a new social network that helps you connect in person with the people you care about most. Over the past twenty five years, Ev has cofounded several companies that have helped shape the modern Internet, including Blogger, Medium, and Twitter. Ev is also the cofounder of Obvious Ventures, an investment firm that focuses on world positive companies addressing major systemic problems. Ev grew up on a farm in Clarks, Nebraska, has two sons, and lives mostly in the Bay Area. This particular episode, this conversation was recorded live in Austin, Texas at the DigNation relaunch. That's dignation.show for the show itself, and that is where dig.com was relaunched. It was recently acquired by its original founder, my good friend, Kevin Rose, and Reddit cofounder, Alexis Ohanian, formerly arch nemesis, but they have joined forces and invited me along for all the fun and surprises as they celebrated the relaunch. Go to dig.com and sign up to get early access when the invites go out one more time. Dig.com. That's digg.com. You can find Mosey, that is Ev's newest creation, at mosey.app. That's available on iOS right now. You can find Obvious Ventures at obvious.com, and you can find him on Twitter. That is also known as x@ev,atev. We're gonna …
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Books
Why Greatness Cannot Be PlannedRecommended“Book "Why Greatness Cannot Be Planned" argues breakthrough products emerge from trying new approaches rather than plotting rigid roadmaps.”
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