Twitter and Square cofounder Jack Dorsey has a thing about living by large bodies of water.

Airbnb recently asked Dorsey to put together a wishlist of places he wanted to stay on the site that lets strangers rent out their homes and other forms of lodging. He picked 15 houseboats.

You'd think he'd have enough ocean in sight, having bought a $10 million house in San Francisco overlooking the Golden Gate Bridge earlier this year.

Perhaps by way of explanation, he quoted Pablo Neruda in May: "I need the sea because it teaches me."

$166 a night for a vintage houseboat in the center of Amsterdam.

$191 per night for this white-walled, modern houseboat, also in central Amsterdam.

$136 per night for this Amsterdam houseboat on the Amstel river. The sleeping quarters are a bit cramped.

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Silicon Valley is a pretty self-congratulatory place, so it's normal for CEOs to issue plaudits when someone gets a big new job, as Marissa Mayer just did running Yahoo.

But we couldn't help noticing how quick and effusive Twitter chairman Jack Dorsey and CEO Dick Costolo were with their praise.

"THRILLED that @MarissaMayer is now running @Yahoo. It's the perfect fit. Congrats Marissa!" Dorsey tweeted.

"Congratulations on the new role for one of the Valley's brightest minds," Costolo wrote.

Here's our tea-leaf reading on those statements: Mayer's departure weakens Google, which has pretty much been gunning for Twitter with its Google+ social network.

Yahoo has been drawing closer to Facebook with the settlement of their patent dispute and a new partnership built around live event coverage—a specialty for Twitter.

But Mayer is an angel investor in Dorsey's other company, online-payments startup Square, and a fairly enthusiastic Twitter user, despite Google's push to have employees use Google+. So Dorsey and Costolo are likely betting that Mayer as Yahoo's CEO will be more of a friend to Twitter than interim CEO Ross Levinsohn might have been.

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The Fancy is the New York-based Pinterest competitor that is killing it in social commerce.

It may now have the most powerful business figure in the world—Apple CEO Tim Cook—signed up as a user.

There's an account with the username "timcook" on the service. That's easy to fake. But The Fancy, like Twitter, verifies some high-profile accounts. The timcook account is verified.

CEO Joe Einhorn makes the rounds at Allen & Co.'s Sun Valley conference—Allen & Co. is The Fancy's investment bank and also a backer. Two years ago, The Fancy, then known as ThingD, was the cool mystery startup everyone was talking about at Sun Valley.

This year, Apple CEO Tim Cook also attended.

We emailed Einhorn, who called us back and said he "may have met" Cook at Sun Valley this year.

He also confirmed that his company takes steps to verify the identity of famous users before marking them as verified. But he said he couldn't comment on the account specifically.

"We think the world of Apple and of Tim Cook," said Einhorn.

A lot of famous Internet moguls feel similarly about The Fancy. Twitter founder Jack Dorsey is an investor and board member. Path CEO Dave Morin uses the site, as does Facebook CEO Mark Zuckerberg. (Of course, using the site just indicates that they've signed up and are curious about it—it's not an endorsement per se.) 

The timcook account doesn't appear to be particularly active. It hasn't "fancy'd," or bookmarked, any interesting objects or followed other users. But it has more than 37,000 followers—an unusually high number.

Einhorn notes—again, without specifically commenting on any user—that people are increasingly using the site to buy things rather than for its social features. Users who just buy things with the service won't show any social activity on their profiles.

Here's a screenshot:

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Almost every Friday, Square CEO Jack Dorsey takes new employees on an orientation walk from a statue of Gandhi in back of San Francisco's Ferry Building to the payments startup's headquarters downtown.

Last week, there were 33 people at the statue. "Our biggest Square new hire group yet," Dorsey tweeted.

That group included several people from Google's former Atlanta engineering office—a group of seven, according to Scott Blum, who posted about the move on his Google+ page. (If you squint, you can make out Blum standing next to Dorsey in the photo.)

 Google annonced plans to shut down its Atlanta engineering office after its manager, Bruce Johnson, left to form a startup called Monetology, and released the software-coding tools Blum and his colleagues had been working on as an open-source project.

Square now has more than 350 employees, we're told, including its new Atlanta engineering office. In the United States, it has offices in San Francisco, St. Louis, and New York. It's making a major push to expand internationally, too.

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Square is about to raise $200 million in a round led by Rizvi Traverse Management, the New York Times is reporting.

The deal would give the San Francisco-based online-payments startup a valuation of $3.25 billion—double what it was worth a year ago, but short of the $4 billion to $5 billion valuation it was reportedly seeking.

In the spring, we noted that Square CEO Jack Dorsey and COO Keith Rabois were taking trips to Boston and Baltimore, the homes of big money managers like Fidelity and T. Rowe Price.

But those firms seem to have lost their appetite for late-stage investments in private tech companies, having been burned by the post-IPO performance of Groupon, Zynga, and Facebook. Typically, they recycle profits from those deals into new investments. Since in many cases those companies are trading below where the private-equity investors bought their shares, there's simply less money available in that asset class for companies like Square.

But Rizvi Traverse, run by Suhail Rizvi, is in a different category. For one thing, it's a known quantity to Square management as an investor in Dorsey's other company, Twitter. And it is flush, having recently sold talent agency ICM and Summit Entertainment.

Square isn't commenting on its fundraising. But it is definitely showing signs of bullishness. In June, it reported that it was now processing payments at an annualized rate of $6 billion a year. It also hired a new CFO from Salesforce.com.

And Dorsey recently tweeted about the group of 33 new hires he took on an orientation last week—the largest group ever, he noted. Square now has more than 350 employees.

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Twitter and Square co-founder Jack Dorsey will be worth more than $1 billion after his latest fundraising round for his mobile payments startup Square closes, Bloomberg reports.

Square is about to raise $200 million in a deal that would value the startup at $3.25 billion, according to an earlier report by the New York Times.

Dorsey will own a 26 percent stake in Square after the new round, valuing his stake at $845 million, Bloomberg reports.

Taking into account the dilution from the new shares issued, that ownership stake is consistent with what we reported earlier this year, when we noted an Alaska state filing that showed Dorsey owning 28.3 percent of the company after a prior financing round.

Dorsey joins the likes of Mark Zuckerberg and other high-profile Web 2.0 entrepreneurs in being some of the richest founders in the world.

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We have some confirmation of the report that Square raised $200 million at a $3.2 billion valuation.

On July 13, Square filed a revision to its articles of incorporation authorizing the issuance of 1,815,870 shares of Series D Preferred stock at a price of $110.14 per share, according to VCExperts.com.

That adds up to precisely $200 million—the figure that the payments startup is reportedly raising in a round led by private-equity firm Rizvi Traverse Management, also investors in Dorsey's other company, Twitter.

VCExperts told us the previous round, which reportedly valued the company at $1.6 billion last year, was done at a price per share of $57.98. That means Square's valuation per share is up 90 percent. Including the new money in, once Square's round is complete, it will be worth just over $3.2 billion.

And cofounder Jack Dorsey will be a billionaire.

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We spotted Square CEO Jack Dorsey Thursday night at a San Francisco fundraiser thrown by actress Eliza Dushku and blogger Ben Parr for ThriveGulu, a charity which helps victims of the Ugandan civil war.

Dorsey is also the executive chairman of Twitter, and he's described his work schedule as eight hours a day at one company, then eight hours a day at the other.

So this is proof that he doesn't always stick to that brutal regimen, perhaps!

Or perhaps not: Dorsey arrived late—just in time for a mention that ThriveGulu was taking donations using Square's iconic credit-card swiper. And he spent the whole time wrapped in conversation with Jean-David Blanc, the French founder of AlloCiné who's also an investor in Square.

So fair to say he was working the party, too.

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Square CEO Jack Dorsey and Jim McKelvey, his cofounder in the online-payments startup, negotiated a great deal for themselves when they started the company.

According to documents reviewed by Business Insider, the founders have a right to sell shares alongside the company in any equity financing. And all they need to do is drop a letter in the mail.

Most startups have two broad categories of stock: common and preferred. Within the preferred, each round of financing represents a different series—hence "Series A," "Series B," and so on. Preferred shareholders usually have more rights than common shareholders—for example, liquidation preferences that ensure they get repaid first in the event of a sale.

Square has three categories: common, preferred, and Series FF. A source familiar with Square tells us that Dorsey and McKelvey are the two holders of Series FF shares.

Holders of Square's Series FF shares have the right, whenever Square does an equity financing, to convert their shares into the class of preferred shares that's being sold and sell them.

Series FF has been much-discussed in Silicon Valley circles. But its actual implementation appears to be rare.

Private sales of startup shares are less controversial than they used to be. Investors frequently allow them, even without the explicit license granted by a structure like Square's, to keep entrepreneurs happy.

This founder-friendly behavior can backfire—for example, when Digg's board allowed founder Kevin Rose to sell some of his shares after the company turned down acquisition offers, he grew less interested in driving the company's success.

But unlike those arrangements, where a board grants permission, Dorsey does not appear to need permission from his board to sell his FF shares. Here's how he exercises his rights according to Square's articles of incorporation—by old-fashioned mail:

Any notice required by the provisions ofthis Section 4 to be given to the Corporation shall be deemed given if deposited in the United States mail, postage prepaid, and addressed to the Board of Directors at the principal business address of the Corporation.

No board vote, no fuss, no muss. Just a stamp.

Whether or not Dorsey has sold any shares, the extremely driven entrepreneur does not show any sign of distraction. If anything, despite his ongoing role at Twitter, where he is cofounder, executive chairman, and product czar, he appears to be more focused on Square as of late.

Square appears to be in the midst of a new round of financing. Two weeks ago, it filed papers authorizing the issuance of $200 million in shares at an implied valuation of $3.25 billion.

Square's Series FF shares represent about 3 percent of the company's shares outstanding, according to an analysis by VCExperts.com—and those are now worth just under $100 million, according to the price the company set for its latest share issuance.

Most of Dorsey's holdings are in common stock—just over a quarter of the company, taking into account dilution from the recently authorized shares. He would need the board's permission to sell those.

Earlier this week, Square held a board meeting, according to a tweet by Dorsey. That's an obvious occasion for ratifying any pending investment deals, such as the rumored agreement to sell the shares it authorized to an investor group led by Rizvi Traverse Management.

Is Dorsey selling in this round? We don't know. The point is, he can if he wants to.

A Square spokesperson did not respond to a request for comment.

Here's Square's articles of incorporation.

Square's Articles of Incorporation

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On a trip home, we had the pleasure of riding in one of the first 10 cabs equipped with Square, a mobile payments point-of-sale device plugged into an iPad (which faces the back seat) and an iPhone.

The cabs started carrying the devices two weeks ago. They're powered by Google maps and show your exact location — including nearby subway stations.

Square is run by Twitter co-founder Jack Dorsey. It started as a simple dongle that connects to your iPhone to read credit cards, but it's since expanded and positioned itself as a complete replacement for cash registers and card readers.

It looks gorgeous. We couldn't tell it was a Square device until the driver had to restart (because of a slight glitch) the iPad.

Like the other New York taxis, you're given an option to tip between 20 and 30 percent for the ride, and it'll send your receipt to an email address you type in (or text it to you).

Square announced that it would begin fitting New York taxis with Square devices in early March, but we were told they first began carrying them about two weeks ago.

Either way, the experience was vastly superior to your typical New York taxi. We're looking forward to seeing more of them hit the streets.

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Starbucks, the giant coffee seller, just invested $25 million in Square, the San Francisco-based payments startup.

In an email announcing the news, Square just acknowledged what we reported last month: The company is raising a Series D round of financing.

Starbucks is taking a small piece of that round. Square authorized $200 million in new shares at a valuation of $3.2 billion. The company didn't say who—if anyone—is buying the rest of the new shares, but the New York Times reported that Rizvi Traverse Management, an investor in Playboy and Twitter, was leading the round.

The deal has a lot of other aspects:

• Starbucks CEO Howard Schultz is joining Square's board.

• Starbucks customers will be able to use Pay With Square accounts to find nearby Starbucks stores and pay for purchases.

• Starbucks will keep making its own mobile apps, which will eventually include a directory of Square merchants.

• Square will process U.S. credit and debit transactions for Starbucks. This is huge: Starbucks's annual sales in fiscal 2011 were almost $12 billion, about two-thirds of that in the United States.

NOW READ: Here Are Three Mysteries Square And Starbucks Just Solved For Us

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We freely admit that we obsess over Square, the innovative San Francisco-based payments startup.

Now it has joined up with another object of our fascination: Starbucks, whose payments and e-commerce ambitions are poorly understood but just took a major step forward with its agreement to invest $25 million in Square.

We've been puzzling over a few things that this deal just snapped together for us.

Why did Square CEO Jack Dorsey take a trip to Seattle last month?

Duh. He had to have been meeting with Starbucks to seal this deal. Dorsey is very deliberately open with his tweets; for example, he openly tweeted about a trip to Boston and Baltimore this spring when he was courting mutual-fund giants in those cities as investors.) 

Why did Howard Schultz quit the Groupon board in May after only 16 months?

Okay, Groupon has been a total mess lately and Schultz may have just wanted to wash his hands of it. But here's an alternative explanation for Schultz's short tenure on the Groupon board: Could he have been thinking about a Square deal even then?

Groupon CEO Andrew Mason must be secretly relieved that nobody is taking his big strategy shift seriously. All the better to quietly rebuild his company as a one-stop shop for local businesses—attracting new customers, scheduling store traffic, and yes, ringing up payments.

Groupon and Square will be competing soon enough. Did Schultz just switch teams?

Why did Square apply for a money-transmitter license in April?

When we wrote about California's innovation-killing Money Transmitter Act last month, we noticed that Square had only applied for a money-transmitter license in April, 15 months after the law first went into effect.

We've since spoken to a source familiar with payments law who has a different take on what's going on. He believes that California's Department of Financial Institutions has an overly strict interpretation of the law and that pure payments processors like Square shouldn't fall under it.

But if Square has broader payments plans—like, for example, getting into stored-value cards—it may need a money-transmitter license. (California's law governs stored-value cards, too.)

Starbucks does a big business in stored value; it's issued 400 million cards worth $10 billion since it introduced the Starbucks Card in 2001.

It's not clear if the Square-Starbucks deal embraces Starbucks Card transactions, too. But if it does, that might explain why Square is covering its regulatory bases.

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We've spent a lot of time over the past few months patiently explaining how Square and Stripe, despite both being in the payments business, are really nothing alike.

Forget about that! The Square-Starbucks deal just made us throw away our cocktail-party script.

Here's how they used to be different:

Square, led by Jack Dorsey, offers in-person payments to small businesses, letting them swipe a credit card and buy physical goods or services.

Stripe, run by Patrick Collison, lets startups like Foursquare and App.net build payments into their websites or mobile apps—no physical card required.

It may all sound like paying for stuff to the layman, but in the payments business, those are seen as totally different categories. Whether the card and the customer are physically present even changes the rates businesses pay.

That's why it was totally cool that, for example, Sequoia Capital was an investor in both companies. They didn't really compete before.

Here's how Starbucks made a mess of things.

Square is now processing all credit and debit cards for Starbucks in the U.S., not just ones made using its Pay With Square app.

That includes loading value onto your Starbucks Card. If you link your credit or debit card to your Starbucks Card on Starbucks.com, it will automatically reload for you whenever you run low.

That transaction, Starbucks confirmed for us, will run through Square, as will other purchases on Starbucks.com.

So Square is now officially in the e-commerce payments business, just like Stripe.

Starbucks may be a one-off, special deal that gets Square access to Starbucks's thousands of physical coffee shops. There's no sign that Square is interested in taking on Stripe's startup customers. And it makes no sense for Stripe—at least right now—to try to serve gigantic retailers like Starbucks.

But it does show just how hard it is to draw lines in the payments business.

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Adam Brotman, the top Internet guy at Starbucks, is in the spotlight after his company unveiled a big deal to take Square in its 7,000 U.S. coffee shops and invest in the San Francisco-based payments startup.

Brotman reports directly to CEO Howard Schultz, who is joining Square's board.

We caught up with Brotman by phone while he was in a taxicab in New York City rushing from one meeting to the next.

We learned that Starbucks is "doubling down" on its prepaid card and associated mobile app; that the company has been gearing up its infrastructure for more tech partnerships; and that Starbucks is continuing a big in-house development effort, now with Square's assistance.

Here's what you need to know about Brotman:

• He's a rising star at Starbucks. Originally hired in 2009, he started as a VP, added a general manager and expanded his role in early 2011, moved to a senior vice president position later that year, and got promoted to chief digital officer in March.

• He spearheaded Starbucks's innovative iPhone app. You can already pay with your phone in a Starbucks—and that's an initiative Brotman oversaw.

• He runs everything digital at Starbucks. That includes the Starbucks Card and its associated loyalty program; social media and digital marketing; and in-store connectivity and entertainment, including Starbucks Wi-Fi and the Starbucks Digital Network partnership with Yahoo.

• He's an entrepreneur, just like his new business partner, Square CEO Jack Dorsey. In 1996, Brotman started PlayNetwork, a Seattle-area company, which provides in-store music and other entertainment to a bunch of retailers—including, yes, Starbucks. He left PlayNetwork in 2006 to join Corbis, the stock-photo company backed by Microsoft cofounder Bill Gates.

Here's what we learned about the Square-Starbucks deal:

• Starbucks is keeping its Starbucks Card and mobile app. Together, the prepaid card and mobile version account for an estimated quarter of U.S. sales. But Starbucks didn't have a great mobile solution for customers who still wanted to pay with their own credit or debit card. The Square partnership is really for them. Over time, though the Starbucks loyalty program and Square's similar offerings will get more integrated, and Starbucks will encourage consumers to download Pay With Square, Brotman says.

• Starbucks has an internal API, or application programming interface—and Square will be one of the first outside companies to use it. Last fall, Brotman revealed the existence of this API at a conference in San Francisco, but that didn't make many waves. But among tech companies, having an API—a documented way of integrating outside pieces of software into your internal systems—is seen as a key to fast, innovative product development.
  
  Square is not the only company that will tap into it. "We still have ambitions to have a public API and have a number of folks integrated in our system," Brotman says.

• Starbucks is not outsourcing its mobile or digital development efforts to Square. If anything, Starbucks will now be doing more tech work to take advantage of Square's capabilities. The Square partnership will let Starbucks focus its innovation on things like mobile ordering and saving lists of favorite drinks.
  
  "We can leverage the fact that they have amazing developers," Brotman said.

Here's what Brotman thinks of Square and its CEO, Jack Dorsey:

• Design at Square extends to everything, not just products. "I'm so impressed by how Square is designing the company," Brotman says. "They’re designing [it through] the talent they brought in. They’re architecting it."

• Brotman had an intuitive sense that Square and Dorsey were the right partners. "As an entrepreneur, there's a certain sixth sense about things. You can vector out that they’re going to build something great. It makes it more exciting and gives more confidence about getting involved in that partnership."

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Technology Review editor-in-chief Jason Pontin interviewed Twitter and Square cofounder Jack Dorsey last night at the Bluxome Street Winery in San Francisco.

Dorsey said that great technology "gets out of the way completely." Pontin pressed him for an example.

"San Francisco does a great job of timing lights," Dorsey said, pointing to thoroughfares like Fell Street where the lights stay green. "When it works, it gets out of the way. When it goes down, you start thinking about the failures of technology."

That's a lot of weight to put on a red light. And these feelings might explain why Dorsey, despite being a billionaire, sometimes just rides the bus to work and reads a book.

Dorsey has a longstanding interest in how urban areas function, Pontin noted—an interest which helped shape his thinking about Twitter as a force for coordinating actions of large groups of people.

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We should consider Marissa Mayer a founder of Yahoo, said Square CEO Jack Dorsey at the TechCrunch Disrupt conference in San Francisco today.

What does that mean, since she actually joined the company some 18 years after its founding?

Dorsey, who actually is a founder of both Square and Twitter, explained that Mayer wasn't a literal founder of Google, where she was an early employee, or Yahoo, where she's now CEO.

He was a big fan of her hire at Yahoo.

The vogue in Silicon Valley has been to favor founders as CEOs—the great example being Steve Jobs, who stunningly revived Apple when he returned to the company in the late '90s. 

Mayer can fill the founder's spot at Yahoo, Dorsey said, because she has "the drive, the commitment, the moral authority to change the company."

Older companies like Yahoo need to have "founding moments," Dorsey argued. 

"A founder is not a job," Dorsey said. "It's an attitude, it's a role, it's an idea that can happen again and again and again."

Yahoo still has one of its actual founders, David Filo, at the company—and one of Mayer's first moves was to have him report directly to her. (He'd previously reported to a number of different technology executives.)

And Mayer has a lot to do at Yahoo:

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When new employees start at Jack Dorsey's payments company, Square, they receive a welcome kit.

The welcome kit comes in the form of a sleek black box. In it, there's a square-shaped pamphlet that explains "The Four Corners Of Square"—a set of principles for the company:

1. We start small
2. We collaborate in commons
3. We round the square
4. We craft the entire span in a breathtaking way

There's also a Square credit-card swiper, a Field Notes notepad, and a big red book.

The big red book is a piece of literature Dorsey often quotes called "The Checklist Manifesto: How To Get Things Right."

Dorsey now gives it to everyone he employs.

The "Checklist Manifesto" was written by Atul Gawande, a doctor and writer for the New Yorker. Its premise: A simple checklist can help people manage complex situations. Gawande uses a number of examples across a variety of industries, from medicine, technology and even disaster relief to illustrate his point.

"Success metric for my work @Twitter: these books disappear from my desk. (you should read it too)," he tweeted in April.

He particularly likes this passage about venture capitalists choosing which startups to invest in. He quotes it on his Tumblr:

Smart specifically studied how such people made their most difficult decision in judging whether to give money to an entrepreneur or not. You would think that this would be whether the entrepreneur’s idea is actually a good one. But finding an idea is apparently not all that hard. Finding an entrepreneur who can execute a good idea is a different matter entirely. One needs a person who can take an idea from proposal to reality, work the long hours, build a team, handle the pressures and setbacks, manage technical and people problems alike, and stick with the effort for years on end without getting distracted or going insane. Such people are rare and extremely hard to spot.

- Atul Gawande, The Checklist Manifesto

Today is Andrew Borovsky's first day at Square. He's the cofounder of 80/20, a design agency, which Square recently acquired. Borovsky put the picture of his welcome kit on Instagram:

For more recommended reading material, check out 24 Must-Read Blogs For Entrepreneurs >

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This is part of our series on The Sexiest CEOs Alive. 

Jack Dorsey's continued success and dedication to change how we look at the world has led many tech pundits to call him the next Steve Jobs.

Dorsey has had a similar trajectory to Jobs and is quite the visionary. Just as Jobs got the boot out of the company he founded (Apple), so did Dorsey (Twitter). But both eventually found their way back into their respective companies and turned into the lead product visionaries.

How it all started

While growing up in St. Louis, Missouri, Dorsey became interested in dispatch routing, and wrote open source software to help dispatch taxis to waiting customers while he was just 14 years old. He eventually moved to New York City, the capital of taxis, to study at NYU. Several years later, in 2000, he started a company in Oakland, California, to dispatch couriers, taxis, and emergency services from the web.

The birth of Twitter

That same year, Dorsey signed up for LiveJournal, a social network where users can share blogs. Inspired by the experience, he thought of ways to improve the service: make a more real-time, up-to-date blogging service that you can share with friends.

"For the next 5 years I thought about this [real-time blogging] concept and tried to silently introduce it into my various projects," Dorsey wrote in the caption for a Flickr image of his sketch of Twitter (pictured), which he called "stat.us" at the time, in 2006. "It slipped into my dispatch work. It slipped into my networks of medical devices. It slipped into an idea for a frictionless service market. It was everywhere I looked: a wonderful abstraction which was easy to implement and understand."

After dropping out of NYU, Dorsey later found himself working at Evan Williams' podcasting service Odeo in 2006. It was there that Dorsey's idea fully manifested into Twitter and Williams named him CEO. 

In 2008, Twitter's board of directors and Williams pushed Dorsey out of the company because he was struggling to keep the site up and running. This effectively made Williams the new CEO and Dorsey the chairman of Twitter.

In an interview with Vanity Fair's David Kirkpatrick, Dorsey said that it felt like being "punched in the stomach" when the board ousted him from the company that he created. 

Square

After a friend of Dorsey's couldn't make a sale because he couldn't process an American Express card, the two realized they should build a system where anyone can accept credit card payments using a smartphone. Dorsey went on to launch mobile payments service Square in October 2010. 

“Payment is another form of communication,” Dorsey told Kirkpatrick. “But it’s never been treated as such. It’s never been designed. It’s never felt magical. About 90 percent of Americans carry cards, but almost nobody can accept them. We want to balance that out and just make payments feel amazing."

Dorsey later re-joined Twitter's day-to-day operations in 2011 to lead product development as Executive Chairman.

Making Life Better with Technology

While Twitter and Square are very different companies, they share the common goal of using technology to make life better, whether it be through connecting humans to each other or helping small businesses one credit card swipe at a time.

Dorsey has said that he aims for his products to help society work more efficiently and humanely.

"My role as an observer and as a technologist is to show everything that's happening in the world in real time and get us to that data immediately, so we can change our lives even faster, with better knowledge," he told Kirkpatrick.

While on stage at TechCrunch Disrupt, Dorsey revealed that he never wanted to be an entrepreneur, but rather an artist or a surrealist. He even has a deep-rooted interest in politics and has said he aspires to become mayor of New York.

And Dorsey's black, nine-inch tattoo of both an integral and the musical notation for F-sharp, shaped like an S, perfectly encapsulates his interests in math, anatomy, and music. 

But whether he wanted to be an entrepreneur or not, that's what he is today. And he's doing an amazing job at it.

Square is currently valued at an estimated $3.2 billion following a $200 million Series D round from investors including Starbucks and Citi Ventures in September. Twitter has been valued as high as $10 billion.

Dorsey took the #3 spot in our sexiest CEOs list. Who was #1? Read our complete list of the 50 Sexiest CEOs in the World >

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THE GREAT DEBATE: Why Aren't There More Women In Positions Of Power?

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Now we know how Jack Dorsey is handling two demanding jobs at two fast-growing companies.

He's not, really.

The Twitter cofounder made a triumphant return to the company in early 2011, after years away.

Already chairman (after having originally been CEO), "executive" was appended to Dorsey's title to make it "executive chairman," and Twitter CEO Dick Costolo gave Dorsey oversight over Twitter's products.

The new job was a big ask for Dorsey; during his exile from Twitter, he'd gone and started another billion dollar startup, Square, and he remained its CEO.

By June 2012, we heard Dorsey was spending less time at Twitter.

Now, in a profile of CEO Costolo, Nick Bilton of The New York Times confirms that Dorsey's role has been "reduced."

Bilton:

Mr. Dorsey’s role has since been reduced after employees complained that he was difficult to work with and repeatedly changed his mind about product directions. He no longer has anyone directly reporting to him, although he is still involved in strategic decisions.

Mr. Dorsey declined to comment on how people feel about working with him. But, in a statement, he said he considered Mr. Costolo to be one of Twitter’s founders. “He’s had a dramatic impact on the company and the culture,” Mr. Dorsey said.  “He’s questioned everything we started with and made it better.”

Mr. Costolo says he looks to Mr. Dorsey for ideas and sometimes has to pull them out of him. Although Mr. Dorsey is a regular on the media circuit, appearing on CNN, as well as “Charlie Rose” and other programs, he tends to be quiet in meetings.

“Dick does a good job of saying ‘Jack, what do you think?’ ” says Michael Sippey, director of consumer product at Twitter. Mr. Sippey works with Mr. Dorsey to make sure that new features are “Twittery.”

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