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Instagram sale to Facebook made Jack Dorsey 'sad'

Much has been written about how disappointed Twitter's co-founder was to lose out on buying Instagram. A new Vanity Fair piece details the specifics of Dorsey's sadness.

Instagram CEO Kevin Systrom speaks at the LeWeb conference in Paris.
Stephen Shankland/CNET

It's been well-chronicled that when Instagram was sold to Facebook last year, it spurned similar interest from Twitter, probably leading to bad blood between the two companies and a tit-for-tat series of feature shutdowns and one-upmanship.

But a new Vanity Fair story by AllThingsD co-founder Kara Swisher spells out in detail just how disappointed Twitter co-founder Jack Dorsey was upon learning that he'd lost out on the opportunity not just to buy Instagram, but to acquire the talents of the photo app's co-founder, Kevin Systrom, a friend.

Dorsey says the news was [hard] for him to take, as he felt he had developed a bond with the younger entrepreneur. "I found out about the deal when I got to work and one of my employees told me about it, after reading it online I got a notice later that day since I was an investor," he says. "So I was heartbroken, since I did not hear from Kevin at all. We exchanged e-mails once or twice, and I have seen him at parties. But we have not really talked at all since then, and that's sad."
Jack Dorsey's final Instagram post, which he put up 56 weeks ago, just prior to the photo-sharing company's acquisition by Facebook. Screen shot by CNET

The Vanity Fair article covers a lot of ground familiar to those who followed the rapid rise of Instagram and its surprise $1 billion sale to Facebook (which became worth about $736 million in the wake of Facebook's sputtering IPO). There's been no shortage of news reports suggesting that Dorsey was unhappy with Systrom's decision to sell to Facebook, despite Twitter having tried to buy Instagram not long before. But Swisher may have gotten Dorsey to open up more about his reaction than has previously been revealed.

Square, the mobile payments company that Dorsey co-founded and of which he is CEO, did not immediately respond to a CNET request for comment.

In the year since the Instagram-Facebook deal was announced, Dorsey has yet to again use Instagram, a service he had been a big fan of and which he had used hundreds of times previously. He's been a vocal supporter of Twitter's own attempts to dominate photo sharing. (Dorsey is on Twitter's board, though he has no active management responsibilities at the social-networking giant.) Whether it was intentional or not, his final Instagram post -- as Swisher noted -- may well epitomize his feelings about the whole matter. Dorsey's caption was "a simple morning pleasure: an empty bus." But in the context of what went down between the two men, and their companies, the symbolism of the photo certainly could be read to convey much lonelier and darker emotions.