platform on which other software firms can connect and sell their file-related technologies. The only way Levie will become the next Larry Ellison is to insert Box at the nexus of a companyâs most important data. âI have to do everything, all at once, as quickly as possible,â said Levie, gleeful about the fact that he has bitten off more than he can chew. âIf I had a clue how this industry worked, I would not attempt to do what weâve done. I was blissfully ignorant.â
  CHAPTER 7 Â
Jack Dorsey, Twitter, Square:
Jack of All Trades
Jack Dorsey is arguably the most successful multitasker in business history. He cofounded two of the worldâs hottest tech companies almost on top of each otherâsimultaneously building himself a $1 billion fortune in each while serving as chairman of one and CEO of the other.
Twitterâs story, of course, is widely known. Promotional platform, democracy tool, news disseminatorâitâs all that, and Dorseyâs original microblogging vision, too. Twitterâs post-IPO valuation has flirted with $40 billion. Unless youâre a small business eager to accept credit cards, Square is less well-known and its outcome remains far less certainâthough itâs raised $200 million at valuations that, by 2014, had risen to $5 billionâgiven the huge competition emerging in mobile payments. But thatâs largely beside the point: When Eric Savitz spent time with him, the now-thirty-seven-year-old Dorsey was focused on the challenge that most successful entrepreneurs face: How does one allocate time so efficiently that a blockbuster can be achievedâmultiple times?
Â
Y ou cover a lot of ground hanging out with Jack Dorsey. In just the first fifteen minutes of a visit to the San Francisco headquarters of Square, which makes the device that turns a smartphone into a credit/debit card machine, we covered the way he structures his time, how the company organizes work, a recent acquisition, group meetings, corporate transparency, and what he eats for breakfast every morning (two hard-boiled eggs with soy sauce). We darted into the companyâs cafe, where he insisted I try a Kombucha, a fermented tea energy drink. He urged me to try the grape version; bottles of the cherry variety, he explained, tend to explode. âYou wonât like it at first,â he warned, correctly, of the vinegary brew.
Then we were off touring more of the third floor of the storied
San Francisco Chronicle
building. Dorsey looked over the shoulder of someone sitting in an open area among long rows of desks, plying a big-screen Mac, and then joined a discussion at a tall table between a group of graphic artists and marketing staffers. There are conference roomsâ21 of them, all glass-enclosed, all named after notable squares, like Tahrir (Cairo), St. Peterâs (Vatican City), and Old Market (Nottingham, where the legendary Robin Hood may or may not have hung out). In one darkened room a handful of engineers worked on integrating a large project with Starbucks, which invested $25 million in Square and now uses it to process all credit and debit transactions in its U.S. stores.
âWe encourage people to stay out in the open because we believe in serendipityâand people walking by each other teaching new things,â said Dorsey with a slight wave of his hand. âBut every now and then you need to focus as one team.â
This philosophical entrepreneur evokes a little bit of another technology wizard with mystical leanings. But Dorsey is nerdier than Steve Jobs (he is a programmer first, an impresario second), his ego seemingly in check. Like Jobs, Dorsey is a disrupter on an epic scale and a repeat offender. Twitter, the microblogging service he cofounded in 2006, has turned more than 500 million people worldwide into broadcasters of messages capable of starting revolutions. And by accepting e-payments with Square, more than two
  CHAPTER 7 Â
Jack Dorsey, Twitter, Square:
Jack of All Trades
Jack Dorsey is arguably the most successful multitasker in business history. He cofounded two of the worldâs hottest tech companies almost on top of each otherâsimultaneously building himself a $1 billion fortune in each while serving as chairman of one and CEO of the other.
Twitterâs story, of course, is widely known. Promotional platform, democracy tool, news disseminatorâitâs all that, and Dorseyâs original microblogging vision, too. Twitterâs post-IPO valuation has flirted with $40 billion. Unless youâre a small business eager to accept credit cards, Square is less well-known and its outcome remains far less certainâthough itâs raised $200 million at valuations that, by 2014, had risen to $5 billionâgiven the huge competition emerging in mobile payments. But thatâs largely beside the point: When Eric Savitz spent time with him, the now-thirty-seven-year-old Dorsey was focused on the challenge that most successful entrepreneurs face: How does one allocate time so efficiently that a blockbuster can be achievedâmultiple times?
Â
Y ou cover a lot of ground hanging out with Jack Dorsey. In just the first fifteen minutes of a visit to the San Francisco headquarters of Square, which makes the device that turns a smartphone into a credit/debit card machine, we covered the way he structures his time, how the company organizes work, a recent acquisition, group meetings, corporate transparency, and what he eats for breakfast every morning (two hard-boiled eggs with soy sauce). We darted into the companyâs cafe, where he insisted I try a Kombucha, a fermented tea energy drink. He urged me to try the grape version; bottles of the cherry variety, he explained, tend to explode. âYou wonât like it at first,â he warned, correctly, of the vinegary brew.
Then we were off touring more of the third floor of the storied
San Francisco Chronicle
building. Dorsey looked over the shoulder of someone sitting in an open area among long rows of desks, plying a big-screen Mac, and then joined a discussion at a tall table between a group of graphic artists and marketing staffers. There are conference roomsâ21 of them, all glass-enclosed, all named after notable squares, like Tahrir (Cairo), St. Peterâs (Vatican City), and Old Market (Nottingham, where the legendary Robin Hood may or may not have hung out). In one darkened room a handful of engineers worked on integrating a large project with Starbucks, which invested $25 million in Square and now uses it to process all credit and debit transactions in its U.S. stores.
âWe encourage people to stay out in the open because we believe in serendipityâand people walking by each other teaching new things,â said Dorsey with a slight wave of his hand. âBut every now and then you need to focus as one team.â
This philosophical entrepreneur evokes a little bit of another technology wizard with mystical leanings. But Dorsey is nerdier than Steve Jobs (he is a programmer first, an impresario second), his ego seemingly in check. Like Jobs, Dorsey is a disrupter on an epic scale and a repeat offender. Twitter, the microblogging service he cofounded in 2006, has turned more than 500 million people worldwide into broadcasters of messages capable of starting revolutions. And by accepting e-payments with Square, more than two
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