The way to meet up with Johnny Hwin, one of the best-connected kids in San Francisco, is to stand at the garage door of a small repair shop in the iffy section of the Mission District and dial his cell phone until it stops ringing into voice mail and the call goes through. This takes a while, sometimes, because Hwin silences his phone and forgets about it. In the meantime, there’s a lot going on at the corner—commuters edging by with messenger bags, shirtless men in dire straits wandering past. After half an hour, maybe a lot sooner, Hwin will call you back and tell you to stay right where you are, because he’s just leaving his place. It’s unclear from which direction he is coming, or how far, and so you might meander toward a nearby mural, called “Diversity in Progress” (it depicts a blooming tree beside a guy in a sombrero), or perhaps toward a pentagon-shaped house squatting among Victorians like the lost piece of a Lego set. At this point, Hwin will call again to say that he cannot see you. When you finally fall into his sight line, you might get a high five and a low-key welcome (“Hey, man”) before being shuttled through a gate and up a dingy flight of stairs illuminated by a snarl of Christmas lights. This is an art-and-tech collective called the Sub, where Hwin has been since 2009. Today, it’s part of a network of places where the new mode of American success is being borne out.

Hwin is twenty-eight, but could be younger. He has a blissed-out grin and an impish dusting of freckles. His hair is buzzed on the sides but topped with choppy bangs, a rocker coif that makes it look as if a wad of hair just landed on his head from a great height. He often wears a miniature harmonica around his neck, over a black T-shirt, to underscore his musical affinities. For several years now, he has been working as a musician, a tech entrepreneur, and an investor in other people’s startups. His two-person band, Cathedrals, just released a début single and is producing an album in the coming months. At the moment, he and a friend are managing investments of up to two hundred and fifty thousand dollars in private companies.

The Sub has no doorbell or real street address, and its space had been an auto-repair facility until some plywood walls made it a place where people—certain people, anyway—might spend their days. Hwin, who moved in four years and two business ventures ago, now has space in a structure that he calls “the doll house.” It is a precarious-looking loft of two stacked rooms done up with paint and fake flowers to resemble a fairy-tale cottage. The doll house is the most comfortable of the Sub’s five spaces (one guy hangs out in an old elevator shaft), but comfort is not the venue’s premier selling point.

People come to the Sub to be in the swing of things, and the things in which they’re swinging tend to reflect a blend of business and small-scale creative art. At least once a month, the Sub puts on an event to bring together creative and influential people. Possibly there’s a concert or recording session by a musician passing through town (Hwin has co-hosted Twin Shadow and Grimes at the Sub), or maybe the residents will drop their big projection screen and run NED Night (an evening of TED-ish colloquy). The events nurture some odd intersections. For instance, the Sub’s walls are decorated with works by Hwin’s friends, and sometimes a Silicon Valley multimillionaire stopping by for a party will buy something for an honorable sum. Hwin calls intersections like these “pushing culture forward.”

I first met Hwin one afternoon in early summer. He had just been in London as part of something called British Airways UnGrounded, a junket that introduced people like Hwin to other Hwin-like people. “Van Jones, the CNN guy, adviser to Obama,” was there, he told me in the Sub’s living room. “Craig Newmark, from Craigslist, was also on the plane. It’s like we’re all just getting drunk together, but also really talking about interesting policy initiatives.” Besides the small table where we sat—possibly a piece of garden furniture—the room had a couple of mismatched couches, a throw rug, and a gigantic beanbag onto which Hwin would periodically flop. He was wearing a purple hoodie, open to reveal a T-shirt that said “ABANDONED WORLD”; the Cardigans’ 1995 album “Life” was playing in the background. I asked what sort of people he brought to the Sub. “It’s become this underground community hub for creators,” he said. “It just happens that a lot of creators now are entrepreneurs.”

Most of the time, Hwin speaks with a surfer’s lexicon, imbuing words such as “man” and “dude” with a range of courtly inflections. But when he talks about business—about “dealflow” or “product-market fit”—the mellow recedes, his brow furrows, and he says things like “Building an investment company is the manifestation of all my experiences.” Then he offers up a lax woodpecker chuckle (“uhuhuhuhuh”) and goes back to discussing the awesome event that his roommate Alex, the d.j. and Airbnb developer, is about to spin.

“Please understand I can offer you only the fleeting illusion of happiness.” Facebook

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Hwin grew up mostly in Hercules, California, a commuter town of pleasant tract housing and parched hills on the far-eastern cusp of the Bay. His parents were refugees from Vietnam; his mother started a few nail parlors. Johnny was born when they were in their forties. “My mom likes to say I was a gift from Jesus,” he says. (His mother is a Buddhist.) He went to Stanford on a full financial-aid package and majored in psychology. That was where he became interested in business, and also in the Bay Area tech scene. He built one of the first “viral, spammy” Facebook apps, called Quizzes, and it gained fifteen million users. He sold it, but he wasn’t proud of it, and so he used the money to found another company, Damntheradio—a Facebook-marketing platform ultimately used by Lady Gaga and other musicians looking to harness a social-media fan base. He sold that, in 2010, for a combination of stock and cash reported to be in the low seven figures. That’s when his experiment in pushing culture forward really began.

This all made sense in broad strokes, but at some point I realized that I still didn’t understand entirely what he did with his time, so I asked him whether he could walk me through his day. He chose to interpret the question literally: he swapped his hoodie for a heavier bomber-type jacket, and we ambled north. Hwin told me that he had found a happy medium between two worlds. Certain of his friends “spend all week doing due diligence, and other businessy things”; others “are, literally, starving artists in Oakland.” He’s set up his life to make neither sacrifice.

It was a clear, honey-colored afternoon, and the light on Market Street fell through the fronds of palm trees planted around the time of the city’s last big boom. Hwin had a room at the Veterans Community Media Center where he worked on his music, and we went inside. “This used to be a hippie community center, which is why you can see remnants of Buddhas and stuff in the corner,” he said. On one wall, he had hung a poster of the Smashing Pumpkins. Hwin strummed a guitar for a while, and then banged on some drums. Eventually, he proposed that we continue our walk through his day.