May 6, 2024 · 1h 14m · how-i-built-this
Twitter, Medium and Blogger: Ev Williams
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of How I Built This, host Guy Raz interviews serial entrepreneur Ev Williams about his journey from a rural Nebraska farm to co-founding Blogger, Twitter, and Medium. Williams candidly reflects on pioneering modern digital publishing alongside the personal leadership flaws, boardroom conflicts, and sudden ousters that shaped his career.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 33.1% of the talking time here. How this is scored →
Guy as informed peer 2.0 Guest teaching 1.5 Guest disagreement 0.1 Guy pushing back 0.4
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:10 Challenging company strategy at O'Reilly Media
Williams describes his rebellious refusal to conform at O'Reilly, openly circulating critical memos arguing why products were inferior and should not be released.
Hardest push from Guy ▶ 1:03:03 Raz confronts Williams on his Twitter leadership flawsRaz directly confronts Williams with tough public criticisms of his Twitter CEO tenure, specifically calling out his slow decision-making and favoritism in hiring.
Biggest teaching moment ▶ 1:01:00 The three-criteria framework for selling a companyWilliams articulates an analytical framework on why companies sell—founder burnout, existential crisis, or undeniable financial premiums—explaining why Twitter refused Facebook's $500M offer.
Guy holds their own ▶ 35:41 Raz cites Adam Curry's pioneering role in podcastingRaz demonstrates domain knowledge by noting that former MTV VJ Adam Curry was the true early pioneer of podcast distribution before mainstream adoption.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Announcement: Launch of the New Newsletter | 1 | 0 | 0 | 0 | Guy Raz delivers an introductory monologue and newsletter plug, contextualizing Ev Williams' career across Blogger, Odeo, and Twitter. There is no active dialogue in this setup segment. | |
| Growing Up on a Nebraska Farm | 1 | 1 | 0 | 0 | Raz prompts Williams about his upbringing in rural Nebraska. Williams explains how agricultural life fostered an entrepreneurial mindset of self-reliance and independence. | |
| Dropping Out and Early Mail-Order Schemes | 2 | 1 | 0 | 0 | Raz asks Williams about dropping out of college and following copywriter Gary Halbert to Key West. Raz looks up Halbert mid-conversation to confirm his legendary status. | |
| Early Web Development in Lincoln with Plexus | 1 | 1 | 0 | 0 | Williams describes his early website development company Plexus in Lincoln and the intimidation he felt about moving to California until following his girlfriend to San Francisco. | |
| Working at O'Reilly Media in Sebastopol | 1 | 1 | 1 | 0 | Williams recalls working at O'Reilly Media and admitting he was a rebellious, critical employee. Raz lightheartedly remarks on how 25-year-old employees tend to annoy senior colleagues. | |
| Personal Homepages, Evhead, and First Web Tools | 2 | 2 | 0 | 0 | Williams details building Evhead.com and creating single-button web posting scripts before blogging was a recognized medium. | |
| Co-Founding Pyra Labs with Meg Hourihan | 2 | 1 | 0 | 0 | Raz asks about founding Pyra Labs with Meg Hourihan and bootstrapping via contract programming during the dot-com era. | |
| The Accidental Creation of Blogger | 2 | 2 | 0 | 0 | Williams explains turning the internal blogging script into Blogger.com and refusing to pivot to enterprise software even when funds ran dry. | |
| Missed Payroll and the Pyra Team Walkout | 1 | 1 | 0 | 0 | Williams details the painful mass walkout after missing payroll and the strange liberation of maintaining the site entirely by himself. | |
| Conflict Aversion and Early Leadership Flaws | 3 | 2 | 1 | 2 | Raz presses Williams on criticism from former Pyra employees about his poor management skills. Williams candidly agrees and elaborates that his fundamental flaw was deep conflict aversion. | |
| Blogger Pro, Google Acquisition, and Corporate Culture Shock | 2 | 2 | 0 | 0 | Williams explains monetizing Blogger through Blogger Pro, the subsequent acquisition by Google in 2003, and his struggle to fit into corporate structures. | |
| Founding Odeo and Apple's Sudden Podcasting Entry | 3 | 1 | 0 | 0 | Williams explains founding Odeo and how Apple instantly rendered their iPod-syncing software obsolete by adding podcast support to iTunes. Raz cites Adam Curry's role in pioneering podcasting. | |
| The Struggle to Pivot and Building for Oneself | 2 | 2 | 0 | 0 | Williams reflects on the mistake of building tools for podcasters when he was not a creator himself, leading into the company hackathon where Jack Dorsey presented status updates. | |
| Naming Twitter and Protecting the Nascent Spark | 2 | 2 | 0 | 0 | Williams discusses naming Twitter and quotes Biz Stone's metaphor about keeping Twitter a small ember so it would not get suffocated by too many resources. | |
| Mid-Show Teaser: Twitter's Expansion and Leadership Shakeup | 1 | 1 | 0 | 0 | Williams describes buying back Odeo and Twitter through Obvious Corp and trusting intuitive product feel over premature metrics. | |
| The SXSW 2007 Breakthrough Moment | 2 | 2 | 0 | 0 | Raz and Williams break down the breakout marketing move at SXSW 2007, placing hallway plasma screens showing live tweets to create critical network density. | |
| Viral Scale and Unintended Societal Consequences | 3 | 2 | 0 | 2 | Raz asks whether the founders anticipated Twitter becoming an engine for societal division. Williams compares it to early processed food manufacturing where unexpected systemic side effects took time to manifest. | |
| Co-Founder Friction, Jack Dorsey's Ouster, and CEO Transition | 3 | 2 | 0 | 2 | Raz probes into the co-founder friction between Williams and Jack Dorsey that led to Dorsey's ouster. Williams takes accountability for failing to provide direct, healthy feedback as the senior leader. | |
| Turning Down Mark Zuckerberg's $500M Buyout Offer | 2 | 2 | 0 | 0 | Williams describes meeting Mark Zuckerberg in 2008 and outlining a three-part framework to the Twitter board explaining why they should turn down Facebook's $500M acquisition offer. | |
| Reflections on Conflict Aversion and Twitter CEO Tenure | 3 | 2 | 0 | 3 | Raz pushes on the prevailing industry criticisms of Williams' CEO tenure: indecisiveness and hiring cronies. Williams acknowledges both flaws, attributing them to deep-seated imposter syndrome and conflict avoidance. | |
| Getting Fired as CEO of Twitter | 2 | 1 | 0 | 1 | Williams recounts the devastating shock of being fired by the Twitter board via executive coach Bill Campbell despite massive 10x top-line growth. | |
| Founding Medium to Rethink Online Publishing | 2 | 2 | 0 | 0 | Raz and Williams discuss the founding of Medium, with Williams contrasting Medium's networked distribution against Blogger's isolated URLs. | |
| Stepping Down from Medium and Current Life Pursuits | 2 | 1 | 0 | 0 | Williams discusses handing Medium's CEO reins to Tony Stubblebine, backing Mosey, and balancing hard work against sheer luck in startup outcomes. |
Statements from this episode (31)
Williams recommends founders work at an established company before starting one
“Thinking, maybe you should work at a company before you start a company. Yeah. Which is a tip that I would recommend to most people.”
Williams wrote 1990s essay arguing Amazon should strictly remain a bookstore
“There was a couple essays I wrote that were, the only one I remember is why Amazon shouldn't expand beyond books.”
Williams paid off $10,000 in back IRS payroll taxes from first startup
“By the way, when I got to O'Reilly, I was in debt To the IRS. Cause I didn't pay payroll taxes at my first company, but I made enough money to pay off the 10,000 dollars or whatever it is, which seemed insurmountable before that.”
Williams: Late 1990s Silicon Valley fundraising was strictly a connections game
“And it was frustrating because everything you read is like, oh, it's so easy to raise money just rolling down the Sand Hill Road, and I didn't know anyone. Like, especially at the time, it's very, very much a connection game”
Williams preferred Blogger going out of business over an enterprise pivot
“And so, like, company blogging, I was like, fine, maybe we can make money, but I'd kind of rather go out of business. It's, that's not interesting. Let's, let's not do that.”
Pyra Labs staff entirely walked out after Williams paused salary guarantees
“And then I sat everybody down and said, we don't have any money to pay you past this next pay period. So you're welcome to come back. I think this is on Friday. You're welcome to come back. I'm going to keep working. If you come back and work, you know, we'll …”
Blogger's server costs dropped from $50,000 to $5,000 after staff departed
“Once everybody left, my costs went from 50,000 a month to 5000 a month still to pay for the servers, and I just wanted to keep building it, so I kept building it.”
Williams admits being conflict-averse and poor at relationship management at Pyra
“I would say, worse than that, I don't think I was good at relationships, which, even more fundamentally. I mean, management is a particular skill, but I wasn't good at relationships, i.e. How to deal with conflict, the most important thing, and I avoided confl…”
Williams: September 11 attacks forced mainstream journalists to take blogs seriously
“Nine 11 was actually a big moment for blogs, and it's when, the way I would describe it, it's when journalists started taking them seriously.”
Blogger was Google's first acquisition involving employees rather than just IP
“We were literally the first acquisition that involved people. They had bought some IP, but we're the first group of employees to come in who were Googlers, but not.”
Williams suspects Google has lost money running Blogger for 20 years
“Blogger, I'm happy to say, 20 years later, is still running. And anything written on Blogger 20 years ago, unless the author took it down or it was like a violation, is still up on the internet for free, and Google has, you know, Paid for that, and you know, p…”
Odeo's $5M pre-product seed round eliminated agility against Apple's podcast entry
“We made the mistake of actually raising too much money pre-product, really even pre-product, we raised five million dollars, which was a terrible mistake because it allowed us to grow the team to the point where We just weren't nimble enough to easily pivot”
Founders should build for themselves unless exceptionally skilled at user research
“One of my fundamental rules, I can believe, is if, unless you are really good at user research, Build, build products for yourself.”
Kevin Systrom and Jack Dorsey paired to build Odeo's desktop podcatcher
“We also had Kevin Systrom, founder of Instagram. Was working for us as an intern. So, Kevin and Jack paired to write our, I think our installable podcatcher, as we called them.”
Odeo board rejected Williams' offer to return remaining $3M in funding
“I actually went to the board. I think we had three of the five million dollars left. And said, I can't sell you on the future of this company. Maybe we should just give the money back and go away. And the board was like, well, we didn't invest in podcasting. W…”
Initial Twitter hackathon prototype included an audio feature that Williams removed
“I do remember a conversation where at first there was a version of what became Twitter presented that had audio, and I remember asking, what if it didn't have the audio piece?”
Williams: Intuitive product feeling matters significantly more than early usage metrics
“It felt like a thing, which has, I've come to realize, is the most important thing, and like, it's, feeling is much more important than metrics early on.”
Williams: Tech founders frequently over-index on data over intuition early on
“It's so easy to get Overwhelmed by data, especially in tech. And as soon as you have anybody using your product, the attention turns to numbers, and testing, and people try to be very scientific about it.”
Displaying live tweets on SXSW 2007 hallway screens created Twitter's tipping point
“Basically, everybody, everybody there got on Twitter. And, you know, it was a few thousand people, and again, lots of journalists, lots of bloggers, and so then they talked about it and wrote about it. It was a moment, just capturing lightning in a bottle amon…”
Williams owned 100% of Twitter through Obvious Corporation following SXSW 2007
“I still owned a hundred percent of it at that time through obvious, but it was clear that we needed to grow.”
Williams defends Twitter's heavily criticized trust and safety staff as integrity-driven
“You know, the team over the years gotten a lot of flack on the trust and safety side, but those people are some of the most earnest, hardworking, Integrity-driven folks I've ever seen in, in the world of business”
Jack Dorsey had never been a manager before becoming Twitter's CEO
“Jack went from individual contributor, he had never been a manager, I believe, before he became CEO of this very fast-growing company,”
Williams claims he did not plan to take over as Twitter CEO
“He was pushed out, and then I became CEO, which It's hard to believe, but it wasn't actually my plan. I still didn't necessarily want to be CEO. And we talked to a few other candidates, but then I was like, okay, maybe I'm the best person to be CEO.”
Facebook offered $500M in stock for 30-person Twitter in 2008
“Facebook, of course, was private at the time, but based on their valuation, they could do a stock deal that may value us around Half billion dollars, and that was a lot of money, and we were maybe, no, we were we were 30 people at the time.”
Founders should only sell for burnout, imminent failure, or undeniable money
“I thought about it very deeply, and I came up with this, like, okay, why would you sell a company? I think there are three reasons, and none of these meet that criteria. Three reasons being, you don't want to do it anymore, and so you need someone to do it for…”
Williams admits he was not a great CEO for a scaling Twitter
“I was not a great CEO by any stretch, and I think I was getting better at What I was very good at was product, and knowing, in my opinion, product and strategy, and knowing where to take the company, what we should build. But the company got to a size where lo…”
Twitter's conflict-averse board never gave Williams negative feedback before firing him
“Somewhat ironically, the board of Twitter had a lot of conflict aversion. Because they never, never gave me that feedback to my face. I didn't know I was going to be fired at all, because no one ever told me I was doing a bad job. So there was a whole culture …”
Twitter grew tenfold in valuation and headcount during Williams' CEO tenure
“The company grew 10 X in users and employees and valuation in the two years I was CEO”
Williams warns founders against accepting executive coaches hired by venture capitalists
“It was my coach at the time, hired by a VC, which is a bad idea Bill Campbell, who told me”
Social networks derive value from distribution and connectivity, not content hosting
“What we had learned from social networks was that
The value was in the connectivity. Like, if Twitter just did what Blogger did and posted your tweet to a webpage and didn't fan it out, if there wasn't this follow mechanism, it wouldn't be very interesting. I…”