That's the question at the heart of a provocative Vanity Fair piece "Twitter Is Betting Everything On Jack Dorsey. Will It Work?" \n\nDorsey has shades of Steve Jobs in his story. He was the longest serving CEO of Twitter, most notably during its high growth years, but was kicked out for "non-CEO like behavior," spending his time learning to sew and doing hot yoga.\n\nSince his ouster, Twitter has struggled. Recent reports suggest that Snapchat just passed it in daily active users. Ouch!\n\nMeanwhile: Dorsey has matured as a CEO. In his time away from Twitter he launched Square, which is now valued at a measly $5 billion. And then he was asked to re-join Twitter and take the helm as CEO. He likes Square so much, he has remained its CEO while also becoming Twitter's CEO. That's either a great sign of self-confidence or foolishness. Dorsey is stepping into a hornet's nest. From the Vanity Fair piece:\n\nTwitter, which was once among the hottest companies in Silicon Valley, had stopped being cool. It had lost out on news to Facebook; on millennials to Snapchat; on China and India to WhatsApp. Instagram was eviscerating it on images. In a remarkably short time, it had slid from the second-largest social-media company to the ninth. And while Twitter still had 300 million monthly active users—or M.A.U., as they are known in Silicon Valley—it had stopped growing. And there is nothing scarier in Silicon Valley than a company that has stopped growing. As a result, Twitter’s stock had been on a jagged decline for 18 months. \n\nThere aren't many CEOs that can step into that situation and turn it around. Jobs did it for Apple. Can Dorsey do it for Twitter?Dorsey remains a sometimes controversial figure. He was called out for being a billionaire that was wearing a "Stay Woke" shirt. Dorsey remains a sometimes controversial figure. He was called out for being a billionaire that was wearing a "Stay Woke" shirt.