A Fortune tech writer comes clean about his early take on a not-so-Obvious startup.

By Miguel Helft
September 13, 2013

FORTUNE—I was wholly uninterested in Twitter. Frankly, I thought it was dumb. It was November 2006, and I had gone to interview Ev Williams.

Already a serial entrepreneur, Williams had become something of a Silicon Valley rebel. He was speaking publicly about turning his back on venture capitalists. Bruised by the failure of his latest startup, Odeo, Williams put his money were his mouth was and did something unheard of: he dipped into his pocket to buy back Odeo from its venture investors to the tune of $2 million (Williams had sold his earlier company, Pyra Labs, to Google, for a much larger sum). Williams renamed it the Obvious Corporation and said he would use it incubate “sustainable” companies. Mostly free from investor pressures, he said such companies would be more fun and allow for more creativity.

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Williams’ rebuke of the Valley’s entrepreneurship model had made him something of a cause celebre and I wanted to write about that for The New York Times, where I worked at the time. Williams greeted me at the door of his South Park offices in San Francisco, and took me upstairs to discuss his thoughts on entrepreneurship. As we talked, he insisted on showing me Twitter, one of Obvious’ first projects. Spawned at Odeo, Twitter’s assets returned to Williams’ control when he repurchased the startup.

I kept asking Williams to talk about his ideas for Obvious. He kept coming back to Twitter, which he thought had potential. He pulled out a feature phone to show me how it worked. I was unimpressed. The number of users — I believed it was in the thousands — was unimpressive, even for a service that was only a few months old. And anyway, why would anyone need a new way to communicate online?

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Williams said Twitter was perfect for the Obvious model. It was small, not mature, and only needed a handful of people. But, exactly what was it, I asked? “It’s a blogging app but it is all about quick little updates,” he said. It’s for “real time blogging,” he added. Twitter barely got a mention in my Times story, where I described it as a “blogging-like tool for quick updates.”

Williams was wrong. Twitter would need VC funding. I was far more wrong, though, and I refused to admit it for almost two years. I began tweeting in August 2008.

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