It's a cool, early spring night in Santa Monica, California, and Ian Rogers is sitting cross-legged on the floor of his house, a glass of red wine at his side, a Minor Threat record on the stereo.

The lean-framed Rogers, a few months shy of 40, is dressed in jeans, a light sweater, and sneakers. At my request he's giving a tour of the many tattoos he's accrued over the past two decades: a smiling visage of Sly Stone, the logo for Steve Jobs' NeXT computer, the names of his two daughters.

They're all blood-borne testaments to the three passions—music, technology, and family—that have propelled Rogers for most of his life. Today he's CEO of Topspin Media, a company that helps artists interact with (and sell to) their listeners directly. But that's just the latest pivot in a career full of deep-horizon foresight and Gump-ish good luck.

- Better Than Human

Rogers got his start in the industry as a college kid in the early '90s, when he built one of the first music sites on the web—a crude but dense tribute to the Beastie Boys. Since then he's been a firsthand witness to the music's bumpy, grumpy transition into the web era. He helped midwife the MP3, sold albums online well before iTunes, and foresaw the pay-what-you-like model back when people were happy to shell out $19 a disc. Later, as a dotcom exec, he spent years trying to build a streaming service that would have looked a lot like Spotify does today.

Rogers has always urged the industry to make music easier to get—advice the major labels have consistently ignored, choosing instead to erect an obstacle course of odd laws, adversarial formats, and frustrating software. Partly as a result, the business has slowly deteriorated from a cash-moated kingdom to a midapocalyptic crazytown, with all sides locked in gainless combat.

Today, though, Rogers is through trying to tell the labels anything. With Topspin, he's hoping to prove that musicians are better off kicking out the middlemen and doing the grunt work themselves. They can use Topspin's software for everything from selling concert tickets to collecting fan data to distributing MP3s and merchandise. Topspin isn't the only direct-to-fan company, but it's one of the biggest, with tens of thousands of users and a client list that includes Eminem, Paul McCartney, and the Pixies.

But Topspin's biggest lure might be Rogers, who's long been an inadvertent oracle for the industry; many of his commonsense solutions have gone on to become the law of the land. If anyone understands how to steer the perpetually transmogrifying music biz, it's him. Not just because he's a smart dude but because his own life—like that of his industry—has been a series of sudden, momentous, and fateful changes. Strangely, understanding Roger's personal story is helpful in understanding both the missteps and the future of the recording industry.

It's an unlikely tale, given that the only "plan" Rogers ever really made, back when he was a teenager, was to get stoned and skateboard the rest of his life.

But, like most grand plans, it all came undone when he met a girl.

It is the fall of 1987 and Rogers—lanky, barely 15, with a long-banged skater hairdo—is playing hooky in his buddy's Firebird Trans Am, rapping along to LL Cool J's "I'm Bad" as the boys make their escape to the Michigan border. Behind them is Rogers' hometown of Goshen, Indiana, a small industrial city with a population of about 20,000 people—many of whom, it seems to Rogers, do not care for him. He and his friends are skateboarders, and in the mid-'80s, for reasons that still won't make sense years later, skateboarding is viewed as a social ill, somehow more akin to devil worshipping than, say, loitering. Rogers and his crew are chased away from wherever they try to lay down wheels. They feel genuinely hated.

Just when Ian Rogers thought he'd get stoned and skateboard forever, it all came undone. Since then, his life—like the music biz—has been a series of sudden, momentous changes.Which is why, every once in a while, they ditch class and take hours-long road trips to Illinois or Michigan, where they coast the concrete with a minimum of hassle. Today the boys are headed to Ann Arbor, and once they arrive Rogers will look around and think the same thing he does whenever he leaves home: "This is the real world."

But at the end of these short furloughs, Rogers and his friends always wind up back in Goshen. Odds are it will stay that way. No one talks to him about going to college, though he's a smart kid—a bit of a prodigy, even. Before he was 10 years old, he was taking computer programming classes. There's a picture of him from that time, sitting in front of his stepdad's Apple II, his mullet swaddled in a giant pair of headphones. A few years later, his stepdad moved out, taking the Apple with him, and money got tight. Rogers hasn't really touched a computer since.

So he skates, dodges the local jocks, and tries to get out of town whenever he can. When he's not on his board, he listens to music. Rogers grew up with his older brother's hard-rock albums in one ear and his mother's country collection in the other, but lately he's been taken with hip hop and punk, two genres that smart, stranded kids tend to glom on to out of desperation. There's this one song, by Minor Threat, that he plays all the time: I can't keep up, I can't keep up, I can't keep up, the lyrics go. Out of step with the world. Whenever he hears that song, he feels as though he's listening to friends he simply hasn't yet met.

But that kind of music can be hard to find in Goshen, where the closest decent record store is more than 20 miles away and MTV-ignored bands like the Misfits are all but urban legends—rumored to exist, impossible to verify. Rogers has to depend on either his friends' mixtapes or the records he mail-orders from the back of fanzines.

One day, not too long after his Ann Arbor trip, a 7-inch EP from a Bay Area punk group called Isocracy arrives in the mail. On a song called "Funky Brakewire," one of the members gives out his home phone number. Rogers calls it, and someone answers. It's not the most revelatory conversation, but for a moment the distance between Goshen and the rest of the world doesn't seem so vast.

He winds up calling the band several times, so much so that, almost 25 years later, he will still recall the number. Yet nothing about those talks can change the fact that Rogers is stuck in Goshen. He vows to do little more than get high and screw around, and he spends the next few years sliding through strange cities with his friends, always in motion but never really going anywhere.

Geek dad: Ian Rogers and his daughter, Zoe—who was born when he was just 17—grew up together at the center of the digital music revolution, with a little help from friends and surrogate family members the Beastie Boys.

And then: an unexpected bump. It appears on the belly of his girlfriend, Susi, and she decides to let it grow.

In a strange way, Rogers is prepared for this. His own mom gave birth to her first child when she was around 16, and though his parents have since split up, Rogers' dad stuck around town, living within walking distance of Ian's mother's house. They made it work, but Rogers knows such a situation is rare. "I've got to figure out how to deal with this," he thinks, "because if I don't, I'm going to live in a trailer park."

He and Susi graduate from high school early and decide to get married—mostly because it will qualify them for more financial aid. One morning in February 1990, the couple gets into Rogers' Chevy Nova and heads down to the courthouse to fill out the paperwork. Their moms have to come with them. They are 17 years old.

Rogers works two jobs: one as a dishwasher at a hospital kitchen and one as an announcer at a local jazz station, where he digs into the record library. He hates the syrupy fusion stuff but gets lost in albums like Miles Davis' Pangaea—records that, at first, are assaultive and unpredictable, kind of like punk.

The station offers Rogers a full-time job for $10,000 a year. But when he looks at all the costs of raising a kid—even with the help of WIC cards and Section 8 housing—he realizes jazz radio is no way to make a living. Rogers' mother had decided in her late thirties to go to college; maybe he could do it too.

"You've got a kid. You're gonna need money," Rogers' stepdad told him. "Get a computer science degree. You were always good with that shit."Rogers finds a community college an hour outside of Goshen, and baby Zoe arrives just a few weeks before his first class. At night, when he's not studying, Rogers paces around his living room with her in his arms, listening to the Beastie Boys' Paul's Boutique. One time he falls asleep with her on the couch, only to wake up in a panic, wondering if he dropped her.

They are getting by. But the commute to school is tough, and their options in Goshen are limited. All Rogers can think is "We gotta get out of here."

Susi has taken a year off to be with Zoe, but she got a scholarship to Indiana University, Bloomington, and the offer is still good. They decide to move out there together, and Rogers is able to enroll as an education major. "Thankfully," he'll say many years later, "I knocked up the smartest girl in school."

One day Rogers talks to his stepfather, a truck driver who's been divorced from Rogers' mom for a few years. "You've got a kid," his stepdad tells him. "You're gonna need money. You don't want to be a grade-school teacher. Get a computer science degree. You were always good with that shit."

Rogers walks into the school's computer science department and tells a faculty member he wants to switch majors. She hands him a card and says to send her an email. It's 1991 and he has no idea what that means.

A year later, Rogers is in an office on campus, listening to "Also Sprach Zarathustra." Most people who've heard the dramatic surge of brass and bombast have only experienced it on their stereo or perhaps while watching the opening moments of Stanley Kubrick's 2001: A Space Odyssey. But now it's playing on a school computer. Which in 1992 is really kind of bonkers.

Rogers is still at IU Bloomington, where he's worked his way into the honors program. As part of a computer science project, he's helping the school transfer its hefty music library onto NeXT workstations. For decades, students who needed to hear a piece of music would have to show up at a prearranged time, sit at desks equipped with headphones, and listen to a record en masse. Now all Rogers has to do is press Play and an .au file delivers the music.

This is such a novelty that the head of the music library occasionally marches people in to watch Rogers load up a song. Most people at this point still haven't experienced the Internet, and those who have are doing so mostly with some tight-gripped hand-holding from AOL or CompuServe. But Rogers has been exploring Usenet discussion boards, where he occasionally posts David Bowie lyrics and oversees a Beastie Boys FAQ. Through Usenet he can chat about music with people from all over the country. He is not alone anymore, and he starts to realize, in conjunction with the library project, that the days of long-distance record store schleps might soon be over.

"This is the future of music," he thinks.

Rogers and his colleagues have heard about the World Wide Web, which is mostly of interest to a small sect of academics, government workers, and futurist porn enthusiasts. Thanks to the library project, Rogers begins learning how to build sites, and in the fall of 1993 he starts an unofficial homepage for the Beastie Boys. There are virtually no templates to work from, so he fills it with everything he can find: lyrics, discographies, and photos and magazine articles he's scanned. The site doesn't look great, but it's remarkably thorough, down to the last obscure 12-inch.

Rogers spends hours creating the site, which he works on when not studying or taking care of Zoe. By now he and Susi have split up. They got married in part for the benefits, but Rogers knew it wouldn't last. They lived together until they could afford to live apart, with Rogers ultimately moving into an apartment across the street. Divorce at that age is easier than you might think: There's no money or possessions to argue over, and since Ian and Susi have agreed to raise Zoe together, it mostly comes down to logistics.

Then Rogers gets an unexpected call—from Beastie Boys manager John Silva. Rogers panics; he figures they're shutting his fan site down. Instead Silva asks him to take over the Beasties' all-new professional site—and, while he's at it, to do work for some of Silva's other clients. To Rogers, this almost doesn't make sense. The site is just something he does for fun. Why would anyone actually want to pay him for this? It's like hiring a bunch of 14-year-olds to copyedit Penthouse Forum.

But Rogers agrees and is soon charging $8.50 an hour to make sites for the Breeders and Bonnie Raitt, and even freelances a project for John Tesh: Live at Red Rocks. He hires some friends and starts his own business, all while studying for a graduate degree and raising Zoe. He has a new girlfriend now, but when she sees Rogers moving his bed into the closet to make room for more business supplies, she takes it as a bad sign and soon dumps him.

Eric Ray Davidson

In the summer of 1994, after months of working for the Beasties, Rogers is asked to meet the group in Indianapolis, where they're co-headlining that year's Lollapalooza. At first he declines the offer; he's terrified that they're only asking him to come out of obligation and they'll see him as some dweeby interloper.

But the Beasties don't just want to meet Rogers; they want him to show them what the Internet is. This gets him excited. He agrees to go.

They meet up backstage and spend the day shooting hoops, riding skateboards, and talking about punk rock. "All the things I thought about them from the music were true," Rogers says.

Toward the end of the day, Rogers asks them if they want to talk about the Internet. But they're out of time and need to get on the road to the next city.

"We like you," Beastie Boy Michael Diamond tells Rogers. "Why don't you just stay on tour, and we'll figure more of this stuff out?"

Rogers drives back to Bloomington, drops off Zoe with his mom, and travels to their next gig, in Detroit. Backstage, a roomful of musicians and managers watch as Rogers shows them the future of their industry via a series of slowly refreshing web pages on a monochromatic screen.

But the Beasties get it. They're no longer the beer-pissing wiseasses they were in the late '80s, when they acted like smirking Vikings, cruising from town to town with a giant inflatable dong. They're older now, if not necessarily mature, and they're one of the few acts to grow more self-sufficient as they get bigger: They run their own self-published magazine and label, and they're heavily involved with their own fan club. They see potential not just in the web but in Rogers.

A few months later, the Beasties ask him to go on the road with them again, this time for weeks, not days. He's supposed to be working on his PhD, but he decides to do it—and to take 4-year-old Zoe along for some dates. Together the two leave Indiana. They never really go back.

It's the spring of 1995, and Rogers is standing next to a stage at the Santa Barbara Bowl, watching floppy discs careen through the air. It's only the second night of this weeks-long road trip with the Beasties, and one of Rogers' duties is handing out discs featuring a Beastie Boys custom-made browser, which they'd built with a company called Spry (Netscape is still four months from going public). But instead the audience has turned the discs into ad hoc projectiles, and as Rogers watches one of them ricochet off the Beasties' keyboardist, he becomes convinced he's about to get kicked off the tour.

Yet the group keeps him around, and over time Rogers is upped from freelance devotee to full-time digital consigliere. He not only manages the website (which he updates regularly from the road) but also indulges the groups' borderline-nutso creative whims. The Beasties have always been culturally curious, staunchly DIY art brats, and this makes them ideal test pilots for the still-undefined web. While other groups are debating whether to hold an AOL chat, the Beasties are building CD-ROMs and filming QuickTime VR tours of their recording studio. "We would come to him with ideas and say, 'Hey, can we do something like this?'" Diamond says later. "And he'd look at us like we were crazy but say, 'Yeah.'"

The Beastie Boys were always culturally curious, staunch DIY art brats, which made them ideal test pilots for the all-new World Wide Web.One night on the road, Rogers finds Adam "MCA" Yauch writing postcards to Beasties fans. "Every day, I do a few of them," he explains. "I enjoy it." The moment sticks with Rogers. To him it all but defines what punk rock should be.

At this point, the web is seen within the industry—by those even aware of it—as either a vague threat or a far-off promise, and the efforts of Rogers and the Beasties mostly fly under the radar. That is, until the group's 1998 tour, when Rogers and the Beasties begin uploading live tracks from the road in a new, readily downloadable format—MP3. The songs are the kind of sample-heavy, legally iffy mixes that the group could never put on an album. To Rogers, people need to hear them.

But executives at the band's label, Capitol Records, freak out, and the ensuing ruckus winds up in The Wall Street Journal and on the cover of Red Herring. Eventually the MP3s are allowed to stay online, but to Rogers, the whole fight is ridiculous: Why would a label get in the way of its own artist?

It's a question he will face frequently over the next few years. Though he left Indiana to be with the Beasties, he's eager to stay in the tech world and starts toggling between working for the Beasties' multimedia company, Grand Royal, and for a series of dotcom companies. In 1998 he joins Nullsoft, which has recently launched its desktop MP3 player, Winamp. The software has millions of users, so Rogers naively goes to the major labels and asks if they want to partner up and sell MP3s directly to listeners. "Their response was (A) What's an MP3? and (B) No way, that will never happen. We'll never sell an MP3," Rogers recalls. "And it was so exasperating." Nevertheless, through Grand Royal, Rogers does spearhead the first ever simultaneous digital and physical release, making At the Drive-In's Relationship of Command available for purchase as an MP3 on the same day it hits the CD bins.

In May 1999, Nullsoft is acquired by AOL. Napster is the MP3 trading site of choice but is about to be sued into oblivion. So despite being owned by AOL, Nullsoft releases Gnutella, the first peer-to-peer MP3-sharing service, which quickly earns the ire of the parent company. Rogers soon finds himself pinging uncomfortably between the emerging capabilities of the evolving MP3 world and the interests of his friends, many of whom are musicians and are terrified of file-sharing. "Gnutella was really hard for me to defend personally," Rogers says today. "I had this circle of musician friends who were like, 'Ian, what the fuck are you doing?' And our response was 'Suing this will not work. What you have to do is put out an alternative to it.'"

But the Nullsoft experience proves instructive, particularly when it comes to Winamp. Though the player is distributed as shareware—meaning users are urged but not forced to shell out the $10 fee—the company still pulls in $100,000 a month. The lesson for Rogers is simple: Fans are willing to pay. You just have to give them a reason to buy. (Years later, when Radiohead's Hail to the Thief album is leaked online, Rogers urges the group's manager to put a button on the Radiohead website asking fans to pay whatever they want for the record—a strategy the band eventually uses with 2007's In Rainbows.)

A few years later, on a weekday morning in Los Angeles, Rogers is skating through the streets of Santa Monica, Zoe standing on the front of his board. Ian, Susi, and Zoe moved out here for good in the mid-'90s, when Zoe was about four. Zoe splits her time between her parents 50-50. On the days when Rogers drops her off at school, the other kids watch Zoe get off his board and tell her how cool her brother is.

She grows up around her dad's friends, most of whom are, like Rogers, twentysomething skateboarders. When Zoe is in third grade, she and Rogers move to the canyon town of Topanga, and he and Susi begin home-schooling her. The couple can't keep up with Zoe. They spend hours working on a lesson plan, only to watch her plow through it in 45 minutes.

Rogers makes sure there are plenty of extracurricular activities as well. He sets up a half-pipe in the backyard, and soon she's learning to ride. She also inherits her father's skill for coding and love of music. Together they rap along in the car to early-'90s hip hop like EPMD and the Pharcyde, and Rogers takes Zoe on regular trips to a local record store, where he manages not to wince when she picks out Korn and Mariah Carey albums.

Like her dad, Zoe spends a lot of time around the Beasties. Rogers always tries to bring her on the road with him for a few days, where Zoe watches the shows from the side of the stage. She spends so much time around the group that the Beasties record a song, "Unite," which mentions her by name in the lyrics. Whenever she's at one of their concerts, she runs around the stage as Yauch introduces her to the crowd: "Zoeeeeeeee"!

Throughout the '00s, Rogers consults for the Beasties from time to time but embarks on a series of high-profile new media jobs. After leaving Nullsoft, he cofounds a proto-cloud company called Mediacode, where Zoe accompanies him to so many venture- capital meetings she has the pitch memorized.

Eventually Rogers winds up at Yahoo, becoming head of Yahoo Music, where he oversees the site's streaming music and video services. He loves the gig, but working with the music industry head-on requires way too much time haggling over licensing and results in DRM software that takes forever to install. He grows tired of the pointless mazes the labels have erected around their music. He has long espoused his belief that "convenience wins, hubris loses," and it irks him to see the majors still undermining the very technologies that could save them. "I was fighting with executives over music-video rights," he says later. "It was depressing."

Rogers remembers what it was like having to work to find music—to make those hour-long drives to the record store a few towns over—and he doesn't want to be in the business of barriers. In 2007 he gives a speech at an industry conference in which he declares he won't accept any more label requests that make it harder for fans to get the music they want. "Life's too short," he tells the audience. "I want to delight consumers, not bum them out." Internet rumors put him as the top choice to spearhead Google's new music service. But Rogers is getting off the corporate wagon. A few months later, he leaves Yahoo for Topspin.

In the company's offices not far from Rogers' home, the heroes stare back at you from the wall: There are framed photos of Minor Threat and the Beasties, and the fold-out cover of Paul's Boutique—which the company helped reissue a few years ago—hangs near a Ping-Pong table. There's also an Elvis pinball machine and a drum set by the door, next to a bookshelf holding both Gene Simmons' autobiography and a guide to email marketing.

As Siouxsie and the Banshees plays overhead, Rogers and his team talk about one of the bigger fall projects: Bones Brigade: An Autobiography, a documentary about the team of pro skateboarders in the '80s. Topspin is expanding into film, but most of its clients are musical acts, ranging from stadium headliners like Maroon 5 and Lady Gaga to slow-build, grassroots performers like Band of Horses and Amanda Palmer.

The fan-artist dynamic has changed radically in the two decades since Rogers was stuck in Goshen. Nowadays, talking to that punk band on the phone would be "like getting an @reply today," he says—still thrilling but hardly a rarity. Most acts now attempt to forge some sort of communication with their fans, whether it's an emo late-night Tumblr confessional or a publicist-dictated Facebook page.

What's changed, though, is the way those interactions can now be tracked, analyzed, and used to sustain lifelong (or at least career-long) relationships, which is what gets Rogers most excited about Topspin. The Pixies, for example, used the company's software to collect email addresses of fans, pinpoint them by zip code, and book an entire tour playing cities often overlooked on normal touring schedules. Smaller acts can use Topspin to give away an MP3 or two and then grow their fan list to the point where they have 2,000 followers, then 5,000, then even more. "You build it up until you've got a little business," Rogers says. "That's a gigantic innovation for artists."

Ultimately, he says, he'd like to "fix the artists' end of the spectrum"—which could also be interpreted as a pledge to help bands sneak past the major-label structure as much as possible. In the nearly five years since he left Yahoo, the industry is still holding a tight rein on music. He cites Spotify, which spent years trying to build up all the proper licenses in the US. "It shouldn't be that hard. The fact that it has cost them that much money to get to where they are is not their fault. It's the industry's fault. The industry has stood in the way of building something the industry needs."

Of course, the ego-engorged, multi- tentacled suck-mollusk that is the modern music business still reigns—major-label acts maintain a greasy hold on the charts, and it's impossible to score a big hit without radio. But direct-to-fan companies like Topspin are starting to persuade even the least DIY-inclined artists to bypass the big-label system as much as possible. Eventually Topspin may represent one of the biggest power grabs for musicians since the indie-music boom of the '80s.

By Rogers' own admission, Topspin hasn't yet lived up to its full potential: The software has been tweaked throughout the past year to make it more user-friendly, and the company has had to wrestle with the various existential crises that come with trying to serve both time-demanding high-end artists and struggling newbies. Still, notes Pixies manager Richard Jones, "people have an element of trust in Ian, and are willing to gamble on what he's doing." After all, Ian has been seeing the future of music for more than two decades.

Back at home in LA, Rogers is scrolling through a playlist he's titled Second Acts, filled with bands that initially started out as sequels: New Order, Public Image Limited, Bell Biv Devoe.

Rogers' new wife, Julie, and their 6-year-old daughter, Lucinda, are asleep in the house, after a meal of pizza and guitar-shaped popsicles. Ian and Julie met at a Christmas party a few years ago; at the time, Zoe was taking care of a guide-dog puppy. "I showed up, like, in a suit, with a kid and a puppy," he says, laughing. "Which is a great way to meet girls."

Rogers shows me one of his favorite photos from his time with the Beasties: a picture of Yauch backstage, holding Zoe's teddy bear. Just a few weeks after we meet, Yauch will pass away at the age of 47, after suffering from salivary-gland cancer for almost three years. Rogers will fly to New York for the memorial service, and he'll spend the weeks following Yauch's death telling Julie random, suddenly remembered stories from his time with the Beastie—about their snowboarding trips, or how Yauch wanted to name their CD-ROM project Dingleberry Harvester.

But he'll also make another trip out East, this time to Boston, where he watches Zoe graduate from MIT with a 5.0 GPA. (She's now at Stanford, studying for a PhD in genetics.) That weekend Rogers posts a lengthy tribute on his blog: "What can I say?" he writes. "Not a damn thing. You've already gone further than I ever could have dreamed." Then he adds: "Congrats, baby. You did it. Take a breath. Please, be happy. Know you've already succeeded. Be OK with whatever comes next. Don't be afraid of changing course."

Contributing Editor Brian Raftery (@brianraftery) wrote about music-industry pundit Bob Lefsetz in issue 20.02.