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Twitter's Jack Dorsey dishes the softer side of tech

The Twitter co-founder and Square CEO ruminates on love, empathy, hyper-personalization, fun, and whimsy--as it relates to tech of course--today at GigaOm's RoadMap event in San Francisco.

Jack Dorsey at GigaOM's RoadMap 2011
James Martin for CNET

SAN FRANCISCO--For a guy who's done his share of industry disrupting, Jack Dorsey is sure eager to opine on tech's softer side.

Today at GigaOm's RoadMap conference here, Dorsey took the stage for nearly half an hour and dished mostly about love, empathy, hyper-personalization, fun and whimsy--as it relates to tech of course.

And why not?

As Twitter's co-founder and Square's CEO, Dorsey, 34, is a sort of bon vivant of entrepreneurship. With his hip styling and pithy and sober delivery, he looks and talks the part. As he straddles leadership roles at two of the hottest startups in Silicon Valley, @jack as he goes by on Twitter, is the man of the hour. In a span of six years, Dorsey and his teams have not only upended the messaging space with Twitter's real-time social network and microblogging service, they are also in the midst of disrupting mobile payments and real-time transactions with Square.

During the far-ranging interview, Om Malik, founder of GigaOM, did his best to push Dorsey to divulge his take on what's next. So what did we learn? Dorsey puts people first. Whether it's product design, the impact his startups and products have on humanity, or the sheer delight of connecting with other entrepreneurs in Silicon Valley. People are at the center of Dorsey's universe.

"The arc I'm most fascinated by is the tech that reminds of our own humanness," he told Malik. And to that end, Dorsey explained that people are the underpinnings of both Twitter and Square.

As for product design at Square, for example, "it's very much user-focused first," Dorsey said. "We start with a user script--a user story--and we share the document with engineering, marketing, and risk." That way everyone in the organization gets it and understands what it's all about. To Dorsey, putting humans first helps tool creators be more "relevant." The end result, he said, is a breakthrough payment technology that creates a "frictionless" experience for merchants and consumers. What's more, Dorsey continued, Square lets anyone who wants to create a business start one immediately. There's no need to fork over a load of cash for bulky machines to process purchases, he said.

"The ability to take payments right away unlocks everything," Dorsey said. To him, the most exciting thing is to be able to walk into a coffeehouse like his favorite, Sightglass Coffee, and "not bring out my wallet."

Dorsey also spent some time talking simplicity too. Another key ingredient for any of his products and services--that and craftsmanship. At his favorite coffee house in the city (yes it uses Square), Dorsey spoke lovingly about the handmade lattes and espressos. Good craftsmanship, he says, is about "making things fun--we're in a very serious industry and very serious time..."

Dorsey closed out the talk with this: we need to design products that "have fun, have some whimsy. That is craftsmanship to me."