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Twitter Refused to Buy Medium for $500 Million

And other scoops from Nick Bilton's blistering new report on the embattled social media giant.
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When Jack Dorsey came back to Twitter in 2015, the board asked him if he’d leave his full-time job down the street at Square, the payments company he’d founded, to reclaim Twitter’s Iron Throne. He flat out refused. “I’ll do whatever you need me to do to help the company,” he said. “But I won’t leave Square.” The board, then, had no choice but to name Dorsey the interim C.E.O. of Twitter while he ran Square too.

That was almost one year ago. Now, Nick Bilton reports, Dorsey must contend with Twitter’s problems, including flat-lining user growth and Facebook’s increasing use of live news and broadcasting—Twitter’s bread and butter since its founding a decade ago.

Co-founder Evan Williams, who stayed on the board after Dick Costolo took over as C.E.O., tried persuading Twitter’s board to buy his news company, online publishing platform Medium. It was a move that stood to integrate both Williams and Medium into Twitter’s existing platform, allowing Twitter to move beyond its aggrieved 140-character limit. But it came with a steep price tag: $500 million. Ultimately, the board had to pass, Bilton reports.

The drama, which a board member describes as “Shakespearean,” extends beyond former co-founders trying to wedge themselves and their new products back into Twitter. Last year, before Dorsey again took the reins, Twitter investor Chris Sacca published an 8,500-word screed about Twitter, pushing for changes to the company. When that didn’t work to dethrone Costolo, he took to tweets and interviews haranguing Costolo, who finally had enough and ducked out. Before Twitter’s first quarterly earnings call with Dorsey back as C.E.O., Twitter C.F.O. Anthony Noto pushed Gabriel Stricker, the company’s Chief Communications Officer, under the bus by blaming Twitter’s nonexistent user growth on marketing and messaging. When Stricker pushed back, he got canned.

It’s Dorsey’s last rodeo as C.E.O. Dorsey is confident about live broadcasting as the future of Twitter, including the company’s plan to host live N.F.L. games this year. If he can’t pull this off, he won’t get another chance. “There is no Plan B,” Twitter executives say. “This is it.” There is a Plan B, of course: Twitter could theoretically sell itself, though it’s not clear who would buy it. Google’s Larry Page doesn’t seem interested, and while Facebook C.E.O. Mark Zuckerberg has tried twice to buy Twitter, he probably wouldn’t want to get into a bidding war to do it now, especially now that he’s taking on live news on his own.