Richard Branson arrives at the Manhattan showroom of Shinola, an American-made watch company. There are no flashing cameras nor any deals in the making. He just sits on a couch in founder Tom Kartsotis's office, tea cup in hand and a few pastry flakes leaving a subtle trail from his chin, down his shirt, to the croissant resting on a napkin in his lap. He smiles and gently slips "beautiful" and "brilliant" into the pauses as Kartsotis steers the conversation.

On this bright September morning, Kartsotis and Branson sit in contrast to each other. Both dropped out of school decades ago to start businesses. Yet despite his commanding presence, Kartsotis has avoided media coverage in the decades since starting his first company, the watchmaker Fossil, holding the idea that quality products best sell themselves. Branson, the quieter of the two, is the face and spirit of Virgin.

His public bravado has been at the core of Virgin's marketing strategy, even though Branson insists it hasn't come naturally for him. "I know this sounds very, very strange," he says, "but I was a shy lad once and I had to overcome that."

Today Branson is one of the wealthiest entrepreneurs in the world, holds a portfolio of hundreds of companies — airlines, banking, telecom, space travel — and projects a larger-than-life public persona. Yet it's hard to track down a business professor who has closely studied either his personal or professional idiosyncrasies.

That may be because, contrary to a common assumption, he is not the CEO or chairman of Virgin Group. His title is simply founder, though he does own a large chunk of its holdings (Forbes estimates his wealth at $5 billion) and is considered its vision keeper and chief brand promoter, even if it means dressing in drag.

Yet, despite some business flops (Virgin Brides, for example) and publicity stunts gone too far (a hot air balloon crash at sea), Branson's class-clown strategy has largely paid off. The United States is home to several of his big endeavors. Delta bought a 49 percent stake in his airline Virgin Atlantic, and recently increased trans-Atlantic flights; his U.S. spinoff, Virgin America, is set to go public this fall; and the first Virgin Hotel will open in Chicago in December.

The marketing tactics for all of these ventures rely heavily on Branson, who has long anchored Virgin's brand campaigns. In person, however, he is more bashful and bumbling than suave and self-assured.

"I learned the art of using myself to promote my companies," Branson says in the New York office of Virgin. It is a small space on Bleecker Street. You could walk right in and ride the tiny, rattling elevator up to the sixth floor to a bright loft space with open desks and just a few glass meeting rooms. Branson keeps each Virgin office small — opting to splinter into multiple locations when the staff size gets too big — so that it doesn't feel like a bureaucracy. For that reason, Branson also doesn't keep a desk anywhere, preferring to meet employees on their own turf.


Richard Branson conducts a TV interview at the Virgin office on Bleecker Street in New York City, September 9, 2014. Carlo Allegri/For The Washington Post

He is here to tape a promotional video for the hotel launch, and his agenda for the few days he is visiting New York is smattered with media appearances, a party for clients and the occasional business meeting. At a panel discussion that morning for the Global Commission on Drug Policy, Branson is the only one whose remarks received applause, despite a small show of nerves. As he spoke, one hand pressed tightly between his knees, he rocked slightly in his chair.

"Strangely, I think it made me more real not to be slick, which may have helped us in business rather than hindered," he says later.

There is another trait Branson has turned to his advantage: He is dyslexic.

He recalls cheating off grade-school classmates in order to pass his tests, and how that condition shaped his career in two profound ways. The first is that it prompted him to drop out of school at 15 to start a magazine, his earliest entrepreneurial venture.

"If I hadn't been dyslexic," he says, "almost definitely I would have carried on in a conventional education and most likely wouldn't be sitting here today."

Also, dyslexia strengthened his recruiting and delegation skills, as it gave him a certain humility to count on others. "I think that applies to a lot of dyslexics," Branson says. "You excel at things you can do, and you maybe find other people to do the things you can't do."

One of those things is managing the operations for his many companies. Branson does not run any of them. He brings in a cadre of executives with the expertise he doesn't have, and likes to tell the story of how he didn't know the difference between net and gross until he was 50 years old (he's now 64). A look at his senior team at Virgin Group is full of former consultants, lawyers and investment bankers from top firms such as Goldman Sachs, McKinsey, Bain, and Slaughter and May.

"You barely know a single name of anyone who works for him. They're all quite private, from-the-shadows kind of operators, but he's got some serious grownups who run his businesses," says Richard Hytner, a former Saatchi & Saatchi CEO who is now a marketing professor at London Business School. "The leadership genius is that he has genuinely subordinated his ego to let very, very good people run his businesses for him."

The command these figures have over Virgin businesses is partly what allows Branson to spread himself across so many projects and continents. And as with other moguls, Branson has put more of his time toward social causes and philanthropic efforts as he gets older. His two days in New York were sandwiched between trips to Toronto and Ukraine, where he and other business leaders went to, as he says, "see if we can get some sense behind this horrible conflict."

Beyond his propensity to delegate, Branson attributes much of his globe-trotting and issue-hopping to the difficulty he has saying no. It's the same trait that has gotten him, say, to dangle from a helicopter while flying over Sydney to a mobile phone launch party. Branson and several close colleagues admit that he's rarely the one dreaming up the stunts, but that his willingness to say yes has spurred others to come up with ever more outlandish ones.

It all started, really, when Branson entered the airline business in 1984. Doing crazy things for Virgin became an explicit business strategy. It was inspired by a conversation with Freddie Laker, a former airline entrepreneur who ultimately failed to compete against British Airways. Laker told Branson the only way to survive against a giant incumbent was to grab attention no matter the personal cost. "You're going to have to get out there, make a fool of yourself, get on the front pages," Branson recalls being told. So he did.

In 1987, he made headlines when he was rescued from the Irish Sea after his hot air balloon crashed en route from Maine to Scotland. "He's not someone who naturally stepped out into the limelight," says David Tait, who worked for nearly 20 years with Branson on Virgin Atlantic. "That was very much on Freddie's advice that Richard started doing crazy things."

It is unclear how long Virgin will keep him at the center of its marketing, and how much it still needs him as the link to customers. Branson, for his part, says that all those risky stunts have given him ample occasion to contemplate what would happen to the Virgin empire if he disappeared. His conclusion: "It will definitely outlive me." And yet, Branson isn't quick to move on to life beyond the business.

"He was a willing victim, let's put it that way," Tait says. "He would say, 'I'm only getting on this balloon for the good of the company.' And he'd say it with a twinkle in his eye, which made you know there was a little more to it than that."

Jena McGregor contributed to this report.

Also: Listen to the On Leadership podcast conversation with Richard Branson.