The New Titans of Tech

The latest generation of web entrepreneurs look and act nothing like their awkward predecessors. We styled the men behind four of today's hottest start-ups to show you the new face of techland. Forget geek chic—these guys are just chic.

Airbnb: Grooming by Soni Marron at workgroup-let.com. From left: Suit by Gucci, shirt by Theory, tie by Alexander Olch, pocket squae by J.M. Dickens, shoes by John Lobb. Suit and shirt by Simon Spurr, Tie by Bottega Veneta, pocket square by Tallia Orange, Shoes by Johnston & Murphy, glasses by Oliver Peoples. Suit by Calvin Klein Collection, shirt by Prada, tie by Ralph Lauren Purple Label, pocket square by Bottega Veneta, shoes by Church's. Foursquare: Grooming by Balery Gherman at De Facto for Dior Men. Shirt by Steven Alan. T-shirt and pants by Oliver Spencer. Flipboard: Grooming by Soni Marron at workgroup-ltd.com. Blazer and pants by Brunello Cucinelli. Sweater by Prada. Shirt by Dunhill. Pocket square by J.M. Dickens. Quora: Grooming by Soni Marron at workgrou-let.com. Jacket by Save Khaki. Shirt by Oliver Spence. Jeans by Polo by Ralph Lauren.
Airbnb: Grooming by Soni Marron at workgroup-let.com. From left: Suit by Gucci, shirt by Theory, tie by Alexander Olch, pocket squae by J.M. Dickens, shoes by John Lobb. Suit and shirt by Simon Spurr, Tie by Bottega Veneta, pocket square by Tallia Orange, Shoes by Johnston & Murphy, glasses by Oliver Peoples. Suit by Calvin Klein Collection, shirt by Prada, tie by Ralph Lauren Purple Label, pocket square by Bottega Veneta, shoes by Church's. Foursquare: Grooming by Balery Gherman at De Facto for Dior Men. Shirt by Steven Alan. T-shirt and pants by Oliver Spencer. Flipboard: Grooming by Soni Marron at workgroup-ltd.com. Blazer and pants by Brunello Cucinelli. Sweater by Prada. Shirt by Dunhill. Pocket square by J.M. Dickens. Quora: Grooming by Soni Marron at workgrou-let.com. Jacket by Save Khaki. Shirt by Oliver Spence. Jeans by Polo by Ralph Lauren.

__NATHAN BLENCHARCZYK, 28

JOE GEBBIA, 29

AND BRIAN CHESKY, 29

Founders, AIR BNB__

Airbnb founders Brian Chesky and Joe Gebbia were just looking to make some quick cash when they turned their San Francisco apartment into an impromptu B&B for out-of-town conventioneers. But soon the two college friends, along with Nathan Blecharczyk, a former Microsoft employee, realized they were sitting on a legitimate business opportunity: a website that could pair savvy travelers with underutilized spaces. To help fund their start-up, they raised $30,000 by selling collectible breakfast cereals called Obama O's and Cap'n McCain's. Three years later, Airbnb has more than 100,000 listings—ranging from urban lofts to Yorkshire castles—in almost every country in the world, leading to new vacation experiences for travelers and new income streams for people with spare bedrooms. "We'll probably have more rooms than Hilton by next year," Chesky says.

VITAL SIGNS

Year Founded: 2008

Home Base: San Francisco

Number of Employees: 130

Number of Nights Booked: More than 2 million

Estimated Valuation: $1.3 billion

USER DATA

How Airbnb job training is different:

"The place where we started is really important to our history, so we bring every new employee to the apartment to give him an hour-and-a-half tour." — Chesky

The celebrities you'll find at HQ:

"We had an office-warming with, like, 500 people. Our DJ was none other than MC Hammer. He's a huge fan of Airbnb. We actually had a dance-off. It was a little bit surreal." — Gebbia

What it's like to get the celebrity treatment yourself:

"I have an extra bedroom that I rent out. I have a lot of young entrepreneurs from out of town stay with me. When they ask what do I do, I say I work for a start-up, and they say, 'What start-up?' I tell them Airbnb, and the reaction—it's pretty awesome." — Blecharczyk

Favorite Airbnb stay:

"I had this one, like, a block from Dolores Park in San Francisco. It was beautifully furnished, and you could step out of the apartment and feel like a local." — Chesky

Why we love what we do:

"We got an e-mail from a couple in New York City who lost their jobs. They decided, 'Well, why don't we just list our extra bedroom on Airbnb?' Their listing became so successful that they ended up being able to acquire the apartment across the hall and list that on the site as well. That story is not unique." — Gebbia

Airbnb: Grooming by Soni Marron at workgroup-let.com. From left: Suit by Gucci, shirt by Theory, tie by Alexander Olch, pocket squae by J.M. Dickens, shoes by John Lobb. Suit and shirt by Simon Spurr, Tie by Bottega Veneta, pocket square by Tallia Orange, Shoes by Johnston & Murphy, glasses by Oliver Peoples. Suit by Calvin Klein Collection, shirt by Prada, tie by Ralph Lauren Purple Label, pocket square by Bottega Veneta, shoes by Church's. Foursquare: Grooming by Balery Gherman at De Facto for Dior Men. Shirt by Steven Alan. T-shirt and pants by Oliver Spencer. Flipboard: Grooming by Soni Marron at workgroup-ltd.com. Blazer and pants by Brunello Cucinelli. Sweater by Prada. Shirt by Dunhill. Pocket square by J.M. Dickens. Quora: Grooming by Soni Marron at workgrou-let.com. Jacket by Save Khaki. Shirt by Oliver Spence. Jeans by Polo by Ralph Lauren.

__DENNIS CROWLEY, 34

Cofounder and CEO, Foursquare__

You may think that collecting badges and striving to become the mayor of your local coffee shop is kids' stuff, but Foursquare's 10 million devoted users think otherwise. The service, which Dennis Crowley launched two years ago with partner Naveen Selvadurai, has brought social networking mobile by persuading people to tell friends where they're eating, shopping, and hanging out via GPS-equipped smartphones. "We're solving very hard technical problems," Crowley says, "but the hardest thing for me personally is to figure out how to keep the company running efficiently as we get more people, more offices, and different personalities." Then there's the challenge posed by giants like Google and Facebook, both of which are eager to co-opt the check-in trend Foursquare started. But Crowley is holding strong: He has more experience in this realm than just about anybody, having launched his first location-based app, Dodgeball, seven years before the first iPhone—while still a student at NYU.

VITAL SIGNS

Year founded: 2009

Home Base: New York City

Number of Employees: 75

Number of Users: 10 million

Estimated Valuation: $600 million

USER DATA

Where I don't check in:

"My mom told me not to check in at church anymore. That's a new rule since I dropped my phone at Christmas Mass."

How demanding my job is:

"After we did the Series B round of financing, I went to the World Cup with my brother. That was the first time I took time off since starting Foursquare."

Why I'm based in New York:

"Tech is not the thing that defines New York—there's also finance, publishing, media, fashion. Our beta testers worked in all different industries, and the product became more interesting."

How people are using Foursquare:

"In the early days, we saw people checking in 20 times a day and I'd be like, 'You're not supposed to do that.' Whatever—people will check in however they want. The average user checks in, like, three times a day. I'd say I'm about that."

Airbnb: Grooming by Soni Marron at workgroup-let.com. From left: Suit by Gucci, shirt by Theory, tie by Alexander Olch, pocket squae by J.M. Dickens, shoes by John Lobb. Suit and shirt by Simon Spurr, Tie by Bottega Veneta, pocket square by Tallia Orange, Shoes by Johnston & Murphy, glasses by Oliver Peoples. Suit by Calvin Klein Collection, shirt by Prada, tie by Ralph Lauren Purple Label, pocket square by Bottega Veneta, shoes by Church's. Foursquare: Grooming by Balery Gherman at De Facto for Dior Men. Shirt by Steven Alan. T-shirt and pants by Oliver Spencer. Flipboard: Grooming by Soni Marron at workgroup-ltd.com. Blazer and pants by Brunello Cucinelli. Sweater by Prada. Shirt by Dunhill. Pocket square by J.M. Dickens. Quora: Grooming by Soni Marron at workgrou-let.com. Jacket by Save Khaki. Shirt by Oliver Spence. Jeans by Polo by Ralph Lauren.

__MIKE MCCUE, 44

Cofounder, Flipboard__

With the possible exception of Angry Birds, no iPad app has been more discussed than the media aggregator Flipboard, which was Apple's 2010 iPad App of the Year. The service, conceived by Mike McCue, a longtime Silicon Valley entrepreneur, and Evan Doll, a former iPhone engineer, emerges from a simple premise: iPad users value aesthetics, and most aggregators are ugly. So when Flipboard pulls from your Facebook, Twitter, and other social feeds, it reshapes the content to read like a magazine, with bold images, headlines that pop, and navigation that mimics page-flipping. Initially, the product generated more interest than the company could handle. "It was way more than we ever anticipated on launch night," McCue explains, "which crashed our servers pretty quickly." But as anyone who's seen The Social Network knows, that's an auspicious beginning. The next step toward world domination: Flipboard for iPhone, expected later this year.

VITAL SIGNS

Year Founded: 2010

Home Base: Palo Alto, California

Number of Employees: 42

Number of Users: 3 million

Estimated Valuation: $200 million

USER DATA

Aesthetic inspiration:

"The front page of the Wall Street Journal. I think it's a work of art. All the news of the entire world is boiled down to one page you can easily scan."

How to keep Flipboard feeds compelling:

"I have a Facebook list called 'Most interesting friends,' which is basically a subset of all of those friends who tend to post really interesting things, not just pictures of their dogs."

Start-ups are like having children:

"I have four kids. By the time you get to your second or third or fourth, you know what really matters and what doesn't really matter. It's very similar with a start-up."

Most obnoxious start-up lingo:

"'What's your exit strategy?' Anybody who goes into a start-up thinking about an exit plan isn't likely to build something of durable value."

Best way to blow off steam:

"Actually, my wife and I just went to Alaska. To have four days where you're totally, totally offline and all you're worried about is not getting eaten by a bear—that was liberating."

Airbnb: Grooming by Soni Marron at workgroup-let.com. From left: Suit by Gucci, shirt by Theory, tie by Alexander Olch, pocket squae by J.M. Dickens, shoes by John Lobb. Suit and shirt by Simon Spurr, Tie by Bottega Veneta, pocket square by Tallia Orange, Shoes by Johnston & Murphy, glasses by Oliver Peoples. Suit by Calvin Klein Collection, shirt by Prada, tie by Ralph Lauren Purple Label, pocket square by Bottega Veneta, shoes by Church's. Foursquare: Grooming by Balery Gherman at De Facto for Dior Men. Shirt by Steven Alan. T-shirt and pants by Oliver Spencer. Flipboard: Grooming by Soni Marron at workgroup-ltd.com. Blazer and pants by Brunello Cucinelli. Sweater by Prada. Shirt by Dunhill. Pocket square by J.M. Dickens. Quora: Grooming by Soni Marron at workgrou-let.com. Jacket by Save Khaki. Shirt by Oliver Spence. Jeans by Polo by Ralph Lauren.

__CHARLIE CHEEVER, 30

Cofounder, Quora __

When you want to dig up some obscure fact, you probably head to Wikipedia. But you won't get any sort of analysis or commentary there. That's why two Facebook expats launched Quora, Mark Cuban ("Should NCAA players be paid?"), and AOL cofounder Steve Case ("What factors led to the bursting of the Internet bubble of the late 1990s?"). Got a question for them? Ask away.

VITAL SIGNS

Year Founded: 2009

Home Base: Palo Alto, California

Number of Employees: 24

Number of Topics: 60,000+

Estimated Valuation: $1 billion

USER DATA

The moment I knew this was going to be big:

"One time, when I went to search for something on Google, the first result was on Quora—and it was a really good answer that I hadn't even realized was on our site."

What I learned from working at Facebook:

"Ten years ago, it was mostly just the nerds who were on the Internet. Now my grandmother can work an iPad. To make a competitive product, you have to put a ton of effort into designing a great user experience and simplifying things."

The apps I'm into right now:

"Photo-sharing apps like Instagram and Path. They're really simple, but pictures are so powerful."

How Quora can get very, very personal:

"There was a question about what it was like to be in the World Trade Center on 9/11, and a couple of people who were actually there chimed in. There's no way that I could've found out what that was like without being connected to those people."

One of the biggest compliments about Quora:

"A guy told me that he got a job through our site. He posted some stuff about a company that someone who works there saw. They reached out to him, met up, and eventually offered him a job."

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