When Apple decided to roll out its now defunct social networking service Ping back in 2010, Steve Jobs turned to an unlikely duo for some informal consulting: Lady Gaga and her then manager, Troy Carter. He invited them to the company’s Cupertino headquarters to check out the product and provide feedback.

It was an unlikely pairing: Carter, a thirtysomething executive with the slight frame of a teenager, eternally decked in stylishly blocky spectacles that added a decade or two to his appearance; Jobs, who famously favored blue jeans and black turtlenecks; and Gaga, known for showing up to important events encased in outerwear ranging from a giant translucent egg to a dress made of meat. On this particular day, though, Jobs’s design sensibilities were the main attraction.

“You see that table right there?” the Apple chief asked, after ushering Gaga and Carter into a conference room. He pointed to an array of a half dozen objects, including the iPhone, iMac, and iPod. “That’s our entire company. Every single product that we make is sitting on that table. Don’t think about things in terms of scale. Think about simplicity. Think about really getting a product right, or a few products right.”

Jobs’s advice stuck with Carter.

“This was a very valuable lesson,” he tells me over the phone one winter afternoon. “You don’t always have to have a million products to be successful. Focus was important.”1

Carter heeded Jobs’s words in his own career, paying particular attention to his investments in Uber, Lyft, Spotify, and a few others. Gaga did, too: she turned herself into one of the world’s biggest stars despite releasing a total of just four solo studio albums in her career at press time, thanks partly to the monumental impact of each one as well as her ability to amplify her reach with the help of the platforms invented toward the beginning of her career.

Though Kutcher was the first person to reach 1 million followers on Twitter, Gaga and Justin Bieber each quickly accumulated north of 100 million followers across all platforms, opening important doors for themselves and their tech-savvy managers.

“The beauty of social media and this era of technology was [how] we were able to disintermediate aggregators and distributors and gatekeepers,” says Carter. “What we found out was a lot of the technology companies became gatekeepers themselves.…Our philosophy was, ‘How do you build a platform to be able to reach these audiences yourselves?’”

For Carter, sitting with Jobs was a key moment on a remarkable journey that began in southwest Philadelphia and blossomed into a fruitful career as a venture capitalist—and a role as one of the few young black venture capitalists in a world dominated by old white men—all following a failed career as a rapper in his early days. “I was broke,” he says. “I didn’t even have a car, let alone any money to invest.”

Carter started his hip-hop run as a teenager, forming a trio with a pair of friends. (“We called ourselves 2 Too Many because we only used to have enough money for one of us,” Carter explained.) They decided to hang outside a Philadelphia recording studio frequented by DJ Jazzy Jeff and Will Smith every week in hopes of meeting their hometown idols—and one day, they did. After playing their demo, they signed a $35,000 record deal through Smith’s production company, releasing their album via Jive Records. Carter went straight to a car dealership and bought a stick-shift Audi, burning through his advance—and his clutch—within weeks. To make matters worse, 2 Too Many’s debut, Chillin’ Like a Smut Villain, bombed.

“We found out…that we sucked,” said Carter, who simultaneously discovered something more important. “More than anything else, more than even the music, [Jeff and Will] respected our hustle.”2

On top of jobs at McDonald’s and Burger King, Carter caught on as a personal assistant—first for DJ Jazzy Jeff, then for Jeff and Will Smith’s manager (now business partner), James Lassiter. He ran the latter’s phone calls, looping in contacts and staying on the line to take notes. Lassiter, who lived eight blocks from Carter’s childhood home, amazed his young charge with the way he could hold his own with the heads of studios and record labels, and gave Carter a blueprint for how executives carried themselves in the entertainment world.

Carter started promoting concerts on the side, luring hip-hop acts from the Wu-Tang Clan to Notorious B.I.G. for shows. One night in the mid-1990s, he booked Biggie for a gig at the Philadelphia Civic Center, only to have the rapper cancel the night of the show. This led to an argument with Biggie’s manager, which turned into a shouting match with Sean “Diddy” Combs, the twentysomething chief of Bad Boy Records. Carter managed to convince the impresario to return Biggie’s performance fee—and to give him a job as an intern, where he learned even more about show business.

Diddy “was the guy who literally could party until three in the morning and still be the first guy in the office,” says Carter. “That really resonated with me. Just to be able to have that sort of maniacal work ethic, but also be able to deal with the guys in the streets…and all the corporate partners as well.”3

After his stint at Bad Boy, Carter moved to Los Angeles to work for Lassiter. He didn’t have a car, so he started using the company’s cab service for transportation—both for work events and to visit a woman he’d gotten involved with. When Lassiter found out, he fired Carter on the spot, and the youngster moved back to Philadelphia, he says, “with my tail between my legs.…I thought I knew everything.”4

Carter dusted himself off and in 2001 teamed up to start a management company with J. Erving (the son of NBA legend Julius “Dr. J” Erving), taking on clients including hip-hop songstress Eve and actor Idris Elba. Three years later, Sanctuary Group—a bigger management company whose leadership included Mathew Knowles (father of Beyoncé)—gobbled up Carter’s outfit. The cultures of the two companies clashed, and by 2007, Carter was out of a job. Soon he and his wife were nearly out of their home, too. Then Carter got a call from an old friend who wanted him to meet a potential client signed to Interscope Records: Stefani Germanotta, soon to be better known as Lady Gaga.

“She walked in with these big sunglasses on, no pants, fishnet stockings, and played hit after hit,” Carter recalls. “What I loved was it looked like she landed from another planet, but she owned it.”5

He agreed to manage her, launching a new company called Atom Factory to house his operations in the Culver City section of Los Angeles. When Gaga’s first single, “Just Dance,” didn’t immediately light up mainstream radio stations upon its April 2008 release, he put her on a Diddyesque schedule, sometimes playing as many as four shows a day. To further boost her reach, Gaga started using Twitter, Facebook, and YouTube for promotion.

Most record labels were still suspicious of tech-based platforms during their post-Napster hangover, but Carter saw social media as a cheap way to reach large audiences. Following the May launch of Gaga’s “Just Dance” music video on YouTube, the song crept up the charts, taking the top spot after twenty-two weeks, eventually clocking more than a quarter-billion views. He even brought Gaga to Twitter’s headquarters.

“She talked a lot about how she’s fairly shy and this actually gave her a voice,” says Elman, who worked at Twitter and remembers a parade of celebrities showing up to learn about the increasingly important platform. “Kanye came through the office and sang a little bit and just talked about how this is the first time he’s had a chance to talk to his community in a direct way, and actually have a voice, and didn’t have to wait for the interview or find the right show. He could just say what was on his mind.”6

Gaga’s debut album, The Fame, went on to sell some 15 million units worldwide, and Carter saw an opportunity to leverage her growing social following for more than just promotion. He helped her fund the video for her song “Telephone,” featuring Beyoncé, by teaming up with Interscope to place a lengthy list of brands in the footage. In one sequence, Gaga feeds diner patrons a batch of poison-laced sandwiches topped with Miracle Whip (a paid integration confirmed by the company); in another, she uses a cell phone from Virgin Mobile (her tour sponsor) and headphones by Beats (her own Heartbeats line).7

Gaga earned $62 million in 2010 and another $90 million in 2011, by my estimates, and Carter’s bank accounts suddenly swelled with his eight-figure managerial cut. Finally flush, he still worried about what would happen if the cash stopped flowing—always a possibility, given the whims of entertainment and entertainers alike. So when Guy Oseary pointed him toward a chance to invest in a video messaging startup called Tinychat, Carter leapt in, quickly reorienting Atom Factory’s mission to include startup investment in addition to artist management. An outlay into eyewear startup Warby Parker soon followed.

“Few people understand the way that information travels and trends start better than Troy,”8 noted the company’s chief, Neil Blumenthal. Or, as Elman puts it: “Troy was very early at making relationships with these companies and really trying to understand how to have his artists use them to grow their own influencing communities.”9

Perhaps more than anyone, Ron Conway helped Carter get his bearings in Silicon Valley. The manager spent the better part of a day sitting in the angel investor’s San Francisco apartment, taking notes on a legal pad about how to build his investment strategy. Conway’s strategy of cultivating a circle of savvy friends and following each other into intriguing deals made sense to Carter, especially as his Northern California circle grew.

“The network from being a talent manager fit quite naturally into some of the needs that young founders were looking for…in terms of business development, marketing, branding support,” says Carter. “Just having that experience of working with talent over the years was transferable to the work that I’ve done with founders.”10

In 2012, when arguably the world’s most famous pop star was seventeen years old, I wrote the Forbes cover story on him with the unlikely title of “Justin Bieber, Venture Capitalist.” Yet when we sat down for the interview in a Hollywood recording studio, it was the singer, not the reporter, who opened with a question.

“Did you see the Taylor Swift Punk’d?” he asked, referencing an episode in which he goads the superstar into joining him for a songwriting session in Malibu, convincing her to set off fireworks that appear to set a boat alight in the midst of a marine wedding. “She was like, ‘I hate you!’”11

Pranking celebrities was one of several ways in which Bieber was attempting to mimic Kutcher. With the help of manager Scooter Braun, the party promoter turned megamanager who’d discovered Bieber on YouTube in 2008 and guided his rapid ascent, he’d accumulated stakes in an array of tech companies. Bieber settled into a chair behind a keyboard as I began to ask him questions—most importantly: Why had he, a teenager from an obscure hamlet of 30,000 in central Canada, suddenly begun to invest in startups?

“The tech aspect is just fun for me,” he said, tapping out a fresh beat on a nearby drum machine. “I’m always finding new apps that I love on my iPhone and my iPad.”

Boom. Boom-boom chuk. Boom. Boom-boom chuk.

“But I’m not going to invest in something I don’t like. I have to believe in the product.”

Beeeep boop boop boop beeeep boop boop boop.

“Each week I’m learning something about my business and what I need to know for my career,” he continued, still clearly focused on the composition assaulting our eardrums. “I’m turning eighteen, you gotta take responsibility.”

Thunk. Thadunk dunk dadunk dunk-dunk.

“And I can tell Scooter what the young people like.”

Braun admitted the same. “He showed me Instagram before I knew what it was,” the manager told me of his teenage charge.12

Bieber was able to relate to youngsters in a way that Braun, twelve and a half years his senior, could not. But the latter knew his own demographic quite well—back in 2004, he attempted to place an angel investment in a nascent social networking site then known as Facebook.com. He emailed Mark Zuckerberg, whose contact information was listed on the site, only to be rebuffed; the Facebook founder wasn’t looking for any capital at the time. Had Braun been invited to plop even a five-figure sum into the startup at that point, he’d have become a billionaire years ago.

Braun found a worthwhile consolation prize: guiding Bieber to the top of the pop-culture heap throughout the late aughts. By 2012, Bieber was a social media demigod with 43 million Facebook fans, a greater total at the time than that year’s presidential candidates—Mitt Romney and Barack Obama—combined. He also had 21 million Twitter followers, more than anyone on earth besides Lady Gaga, and some credited him for helping build the microblogging site. Elman recalls his colleagues pinning a poster of Bieber on the office wall.

“To be honest, that was about the fact that he was very popular on Twitter and his fans were very rabid, not like, ‘Oh, he’s the reason we’re growing,’” says Elman. “Those were more cool things that it was nice to be an employee and see, but most of what we were building had nothing to do with celebrity.”13

Braun disagreed, and he was ready to capitalize. In Bieber, he’d found not only a generational pop star who would earn hundreds of millions of dollars before he was old enough to rent a car without paying extra, but a human password that would allow both of them to enter exclusive deals in Hollywood and Silicon Valley. And Braun took full advantage of the chance to build an empire of his own, starting in 2009. The idea: to leverage the newfound power a star like Bieber possessed through direct communication with his fans on social media.

“For the first time ever, artists themselves are their own network,” said Braun. “I grew up in a time when an artist didn’t get radio play, you didn’t hear about him, and he would fall out of existence. So [Bieber] and Lady Gaga, they could talk to millions and millions of their fans every single day…we’re never going to lose Twitter or Facebook.”14

By the time I interviewed Braun and Bieber, the duo had amassed stakes in a dozen or so companies. The duo usually joined more experienced investors—to get into social curation app Stamped, they teamed with Google Ventures and Bain Capital—or entertainment world peers: to invest in Tinychat, they joined Oseary, Kutcher, and Carter in a $1.5 million round. They also tried to focus on properties with a philanthropic hook. Ellen DeGeneres (who’s had Bieber on her show many times) pointed them toward Sojo Studios. The social gaming outfit had created a FarmVille-type app called WeTopia in which players earned virtual points that could be translated into real charity donations.

In most of these cases, Braun and Bieber were following the playbook written by Oseary and Kutcher: invest a mid-five-figure or low-six-figure sum in a publicity-hungry startup, leveraging fame for a chance to get in on a private company usually available only to high-flying Silicon Valley investors. It was a good deal for them, but perhaps even better for the entrepreneurs who couldn’t yet draw attention from the likes of Sequoia and Greylock. For such giants with billions to throw around, writing checks smaller than seven figures isn’t worth the trouble.

The traffic on the Hollywood–Silicon Valley highway grew heavier in the early 2010s, and the difference between investment styles grew sharper. While some startups remained insistent that all investors have skin in the game, others lured celebrities with the promise of free stock—known as “advisory shares” or “sweat equity,” with the latter suggesting a higher degree of involvement than the former. One startup known for giving away small stakes: Viddy, an “Instagram-for-video” app that brought on Bieber, Will Smith, and Jay-Z as minority owners and soon had racked up 50 million users.15

The company’s founders recognized that stars brought with them a relatively cheap way to generate impressions. One Facebook post by Bieber might not reach all 43 million of his followers, but if even 1 percent saw him post about Viddy and 5 percent of them downloaded the app, that’s more than 20,000 new users. As the cost of user acquisition approached $10 per customer and brand mentions on Kim Kardashian’s Instagram soared to $300,000, a single Bieber post could be worth several hundred thousand dollars on the open market—easily worth giving away a tiny bit of equity. And Bieber was one of many stars willing to make that trade.

“I don’t know where Twitter or Facebook or any of these things will be in ten years,” he told me. “There could be a new thing that’s going to be better, you never know. I’m always—and [Scooter’s] always—trying to find the next thing.”16

For Braun, still smarting from missing out on an early Facebook outlay, and annoyed that Bieber wasn’t getting anything out of Instagram aside from a massive amount of engagement, Viddy seemed quite attractive—for the right price.

“If we’re coming in and saying he’s going to be a silent investor and no one’s going to know, then we don’t ask for any special treatment,” Braun said. “But if we’re coming in and putting his name to it, and his brand and likeness and his social media power, then we will try and figure out a proper compensation for that.”17

Despite Viddy’s early promise, a change in Facebook’s algorithm gutted its traffic; Instagram itself became a destination for watching videos as well as browsing photos. Viddy sold itself to a company called Fullscreen for a mere $20 million in 2014—far from the nine- and ten-figure dreams held by its early shareholders—before closing down at the end of that year.18

Braun, Bieber, and their peers were learning that the companies offering free equity weren’t always the best ones. Tinychat served as another example: despite the Bieber plugs, the startup never became the next big messaging app. In cases where equity in such companies didn’t come for free, the result was fairly catastrophic for shareholders who’d actually paid for their stakes.

“The impression at first was, ‘Wow, what a great opportunity to invest in an early-stage technology company,’” says Carter. “It was a good learning experience, but not so great an investment.”19

To the techies who’d helped create platforms like Facebook and Twitter, it seemed entertainers had gained quite a bit from the advent of social media, even if they didn’t own stakes in the budding industry’s key players.

“The stars who really rose up during that era really were able to create a lot of value for themselves by building an audience in a direct channel to them in a way that they controlled,” says Elman. “A bunch of these early tech products grew and got very large just because they were great technology.”20

Many creative celebrities had other ideas. Aside from Bono and his early Facebook investment, stars felt they were generally missing out on getting a piece of the platforms where their work was consumed and shared. In 2011, Gaga decided she wanted to change that, with Carter’s help.

“We went through a stage, especially when Facebook and Twitter really started to gain traction, where it was this sort of direct way to be able to reach fans and communities,” says Carter. “This was something that we had never seen at scale before as an industry. Then, what we realized after making that time investment on these platforms [was] that, [at] any given moment, these companies can change the algorithm and start charging you for the ability to reach fans that you brought to the platform.”21

Gaga’s solution was called Backplane. Named for the board connecting the circuits of a computer, the startup began by creating the underpinning of her million-strong fan site, LittleMonsters.com, with the goal of using that template to build social networks for other brands. Joe Lonsdale, who’d previously cofounded data giant Palantir with Facebook investor Peter Thiel, came on to run the company. Silicon Valley titans including Google Ventures, Sequoia, Menlo Ventures, Greylock, and Conway’s SV Angel piled in for a $12.1 million Series A, valuing the company at $40 million. (Due to a nondisclosure agreement, Carter couldn’t comment on his or Gaga’s financial involvement, but it seems they received equity as founders of Backplane.)

As Carter’s community grew, so did his investment opportunities, allowing him to diversify his portfolio. Facebook was one of the first investors in Zimride, and Carter’s connection to the social networking giant allowed him a chance to get in early—before it turned into Lyft. Then he met Shervin Pishevar, an Iranian American investor who invited him to invest in another ride-sharing app: Uber, cofounded by Los Angeles native Travis Kalanick, of Scour.net infamy. Kalanick had crafted his new company to be a sleek limousine-on-demand app, a lineage that would later differentiate it from its crunchy competitor Lyft. Uber had other connections to the entertainment business: namely, its name, which Kalanick had purchased from Universal Music Group.22

Pishevar’s journey to the bleeding edge of the transportation industry traced back to his own father, who drove cabs in the United States after fleeing Iran with his family. “I basically grew up in a taxi,” says the younger Pishevar, who came to America as a child, speaking little English. His education got a boost when he was accepted into a program for gifted and talented students; in high school, he won a science fair for a project that fought malaria-infected red blood cells.23 After graduating from Berkeley, he started a handful of dot-com boom companies, including one that sold to Vistaprint for $118 million. He landed a job at Menlo Ventures after the first bust and guided the firm to lucrative investments in Warby Parker and Tumblr, among others.24

By September 2011, Uber was generating $9 million in monthly fares from its 9,000 San Francisco users and needed to raise double-digit millions to expand to other cities. Pishevar’s firm and Andreessen Horowitz were both eager to lead the round, with Kalanick initially preferring the latter, due to its reputation for entrepreneur-friendly terms. When it seemed the deal had been done, Pishevar congratulated Kalanick on the funding and said he’d happily remain on standby in case it fell through. Shortly thereafter, Andreessen Horowitz reportedly requested a larger pool of shares to be set aside for future hires, lowering the proposed valuation from $300 million to $220 million in the process.25

Kalanick, in Ireland for a tech conference, called Pishevar, in Tunisia for a speaking engagement. “He asked, ‘Hey, is that still on, what you said?’” Pishevar recalls. “I said, ‘Absolutely,’ and I got on the next flight to meet him.…I’m very thankful that I picked up that phone call. My mantra has always been: Get on the plane.”26

The pair spent an evening wandering the cobblestone streets of Dublin, and Kalanick told Pishevar for the first time that he wanted to not only take on the taxi business but challenge the notion of car ownership altogether. Pishevar wrote up a term sheet that valued Uber at $290 million later that night and texted it to Kalanick.

“I nearly had a panic attack waiting for his response, fearing he was shopping it to someone else to get a better deal, so I upped the offer,” says Pishevar. “But he didn’t negotiate. He said, ‘No, two hundred ninety [million] is fine. We’ll do it at that.’ Once I received that text, we closed the deal, and with the support of my partners at Menlo, we were off to the races.”

Pishevar had a plan. As he’d grown closer to Hollywood operators like Carter, he’d come to the increasingly popular realization that the entertainment industry’s renewed interest in Silicon Valley startups could be converted into a very cost-effective way of acquiring new users during Uber’s expansion. With Carter’s help, he put together what later became known as a “party round,” bringing in dozens of stars and handlers with the goal of increasing visibility.

“During that time, most people in L.A. had not heard of Uber, because it was only the black car service in San Francisco at that time,” says Carter. “Me being able to introduce [Pishevar] to some of the managers and artists and talent…pretty much helped fill out the L.A. round for Uber during that time.”27

Notably, the chance to invest in Uber gave creators who felt they’d missed out on owning a piece of the startups directly connected to their business a chance to leverage their fame in exchange for a piece of another valuable, if unrelated, property. Uber announced its Los Angeles presence in 2012 with a bash at a renovated garage venue called SmogShoppe, featuring celebrity investors including Kutcher, Ed Norton, and Olivia Munn. Norton took one of the first rides in the city, a fact that Uber made sure to publicize in a blog post.

They all wrote checks, mostly in the range of five to six figures, joining other stars from Britney Spears to Jared Leto (who has invested in dozens of startups, including zero-commission brokerage outfit Robinhood and meditation app Headspace). There was no free equity, but the creators got in at the same valuation as Uber’s regular investors in the previous round, meaning they’d made significant paper gains the moment they signed on. By 2016, their stakes were worth twenty times what they’d initially paid.28

Kutcher and Oseary had actually invested in Uber previously, after Kutcher persuaded Oseary and Burkle to plow some of A-Grade’s money in a fund operated by Chris Sacca. A onetime close friend of Kalanick’s, Sacca lived in Los Angeles and favored embroidered dress shirts that made him look more like a cowboy heading to a square dance than a high-flying venture capitalist (he has since retired from investing). Sacca got into Uber when the company was valued at less than $10 million, and A-Grade got a slice by extension. Like Sacca, Kutcher recognized that Uber wasn’t just taking on grungy yellow cabs but the very notion of purchasing automobiles.

“I remember the first time we heard about Uber, I was like, ‘Everybody wants to ride around in Lincoln Town Cars? What?’” he says. “Then you start to dig into the power of the network effect and the immediacy, and that you’re not actually taking on the limousine companies. You’re not even actually taking on the taxi companies…once it gets that foothold, the potential of it is, ‘Why own a car?’”29

Sacca was also helpful in recruiting celebrity investors to Uber, including ones who couldn’t write seven-figure checks, like actress Sophia Bush. Best known at the time for starring in the TV series One Tree Hill, she signed on for a low five-figure sum. “Quite low,” says Bush, who’d made her first startup investment in online beauty-booking service StyleSeat a year earlier alongside Kutcher, Sacca, and Uber’s cofounders. “But they were closing a round and it was essentially like, ‘This is what we have left, and this is how many people want in on it,’ and, you know, ‘What would you like to take?’ And I would have liked to have bought more shares than I was able to, but I basically essentially said, ‘I’ll take what’s left. Let’s go. This feels like it’s going to be a really big deal.’”30

Creators may have missed out on owning a sizable chunk of Facebook and YouTube. Still, with the help of Carter and Pishevar, stars from Bush to Jay-Z—a much more diverse cast than Silicon Valley’s traditional investor class—had leveraged their fame to get their cut of the next multibillion-dollar company. “I say all the time that Shervin made more people wealthy in Hollywood than any film or any album,” says Oseary.31 Adds Bush, who would go on to become a startup-investing regular: “Not going to lie, there was a part of me that wishes that of the checks I’ve written, I wish 80 percent of them I had just written to Uber, but it’s okay.”32

About a year after his inspirational visit to Apple, Carter approached Google about bringing Gaga to the company’s offices for a meeting ahead of the tech giant’s planned launch of music streaming service Google Play. Carter wanted to get a sense of what they were building and whether there were any collaborations to be had.

Larry Page, one of Google’s billionaire cofounders, met with Carter and Gaga, as did Marissa Mayer, who left the company to head up Yahoo! in 2012. The latter showed them two shades of green that Google had A/B tested for one of its products, finding that people were much more likely to click on a certain shade than the other. Page extolled the virtues of such research and asked Gaga if she did the same.

“Did Picasso A/B test his paintings?” she replied.33

Carter saw both sides.

“I do believe in pure art and letting art live and be expressive,” reflects Carter. “At the same time, when you have access to information and data of what’s going to work and what’s not going to work…it just shows the difference between pure gut and just going with what you feel is right, which works really well for an artist like Gaga, and going with data, that works really well for a company like Google.”

Despite the philosophical differences, Carter was able to broker a few deals between Gaga and Google, including a commercial for the company’s Chrome web browser and an investment from its venture arm, Google Ventures, in Backplane. Yet for Gaga, creating a platform of her own proved much more difficult than endorsing established giants: the company never really caught on, eventually suffering the same fate as Viddy.

“Technology companies fail,” says Carter, with a seeming shrug that carries through the phone line, toward the tail end of our interview. “I don’t think it’s specific to these particular companies.…look at Apple, [which] failed at Ping and trying to do social.…I think it’s execution.”

Another way of looking at it: no major artist is bigger than a major platform. As YouTube helped boost Google to a valuation in the hundreds of billions and Facebook’s Instagram acquisition ensured it would stay in the stratosphere, content creators gained new ways of distributing their work. But most of them had little to show in the way of equity for their efforts. Yes, Funny Or Die created some wealth for Will Ferrell and a few others, but it was always something of a niche property.

“Do I think one artist is ever going to have a platform of just their content with a billion users like Facebook?” asks Carter rhetorically. “It’s…next to impossible to build.”

But a handful of startups not connected to the entertainment business—like Uber—were beginning to enrich a slew of superstar creators. Those individuals would soon get their chance to own a piece of media platforms as well, thanks partly to the efforts of yet another A-List Angel.