Jack Dorsey
The CEO OF Square on the cash register of the future.

He's best known as the programming whiz who created Twitter, but in 2010, Jack Dorsey launched Square, the mobile-commerce technology that lets you make and receive payments with your phone. Here, the 36-year-old predicts how we'll buy things in the near future.

Cash isn't going anywhere.
"Buyers and merchants will always have a use for it. What we're striving for is not cashless transactions but paperless ones. Money, receipts, accounting—electronic payments can make all that paper go away."

Digital wallets aren't in the cards.
"Battery life is a constraint: You don't want your wallet to be out of power. People also need wallets for IDs, though India is introducing digital identities. The U.S. is behind in terms of identity infrastructure, which is key for ditching the wallet."

Physical stores are sticking around.
"Digital media has created an efficiency that's hard to compete with, but people will continue to crave the warmth you get in a favorite store. Physical stores should leverage that huge advantage with curation—like record stores where you see notes from the owner about what CDs they like and why."

Your phone will save you time.
"iTunes is a good model: You've stored payment credentials with Apple, so you click one button, and that's it. All commerce should be as fast and efficient. You'll be able to order an espresso so it's there when you arrive at a coffee shop. That's coming very quickly."

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Three More Reinventors of Retail

Rachel Botsman
35, director, Collaborative Lab
Mission: Advise organizations that want to join the emerging economy built on consumers' sharing services (like Zipcar and Airbnb) rather than purchasing products.
Backstory: After leaving a job at the Clinton Foundation, Botsman cowrote What's Mine Is Yours (2010), the definitive treatise on the idea of "collaborative consumption," then founded Collaborative Lab.
The next big idea: "Reputation will become a currency. We will think about our reputation trails like we think about our digital footprint today." Naturally, that's the subject of her next book, due next year.

Jared Schiffman
36, founder and CEO, PERCH Interactive
Mission: Modernize retail with elaborate Minority Report–like touch-screen displays in stores. Schiffman's clients include Cole Haan and Kiehl's.
Backstory: Schiffman studied computer science at MIT before starting his first company, Potion, in 2005 to devise one-off retail solutions, then launched PERCH last year as a full-fledged service for stores.
How to beat Amazon: "We're pushing a whole new platform—interactive displays that are information-rich and entertaining. When you go into a store, it should be just as exciting as using your iPad."

Chris Morton
30, CEO and cofounder, Lyst
Mission: Enable fashion lovers to view store inventories, select and save favorites, and get recommendations from celebrities online.
Backstory: The stylish Brit left his career as a venture capitalist to start Lyst because he believed fashion wasn't adapting to digital realities quickly enough.
Midstream makeover: Lyst originally launched as a platform for friends to share fashion picks but nearly folded. So Morton rebooted it to let users follow tastemakers (Nina Garcia), labels (Alexander McQueen), and stores (Topshop). "Fashion is one place where people still want expert opinions," he says.

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The Digital Mavericks

Jack Dorsey (Square)
+ 3 More Reinventors of Retail

Kenna (Myspace)
+ The Protégés of
Apple's Jonathan Ive
+ The Evangelists of Tumblr

Carter Cleveland (Artsy)
+ The Race to Create
the Instagram of Video
+ The Rise of the Social-Media
Image Consultant

Jennifer Pahlka
(Code for America)

+ 3 More Digital Change Agents

Evan Sharp & Ben Silberman

+ 5 More Entrepreneurs

Jared Leto (VyRT, The Hive)
+ How Twitter Became
the Best Place for Comedy