For an ascendant musician turned venture capitalist, D. A. Wallach certainly has the proper trappings. He’s got the requisite house in the same hills where generations of Hollywood stars have lived; parked in front is a Tesla, a fitting nod to Silicon Valley.
Wallach greets me inside his airy abode decked out in all black—save for his shock of curly red hair—and takes a seat, cross-legged, on a cabernet-colored velvet couch. Though he’s in his mid-thirties, Wallach has already parlayed a critically acclaimed music career into a full-time role as a venture capitalist, securing stakes in companies from Spotify to SpaceX. At times, he’s played yenta between startups and some of the entertainment industry’s biggest names.
Wallach’s role as connector had an inauspicious beginning. In 2007, while still a senior at Harvard—where he first met schoolmate Mark Zuckerberg—he brokered an introduction between the Facebook founder and Interscope Records’ then chief Jimmy Iovine, who’d just signed Wallach’s band, Chester French. Iovine was looking for a way to expand into the tech world and decided to fly to the Bay Area to take meetings.
“Jimmy is forty-five minutes late to this meeting,” Wallach recalls. “And he says, ‘Oh, I’m sorry I’m late. Our jet got in…and then we swung by Apple to see Steve.’ Like, my big buddy, Steve [Jobs], and not sort of realizing that Zuck was very quickly going to be a bigger deal [than Iovine].”1
Wallach had imagined himself orchestrating the first of many significant pacts between the music industry and the emerging social media world. He felt that a connection between a founder like Zuckerberg and a label chief like Iovine could start to harness the power of Facebook for the benefit of musicians; perhaps features like the company’s “Like” button could help artists develop a direct line to their fans. But Iovine didn’t make much of a first impression on Zuckerberg.
“Jimmy, you’ve used Facebook, I assume,” Wallach began.
“No, I can’t use Facebook,” Iovine replied. “People are going to be messaging me left and right and I’m going to be overwhelmed with stuff.”
Man, I set up this big meeting, this is me throwing everything I have, Wallach thought to himself. This is the sum total of my powers that I can introduce these two. And Jimmy doesn’t know what Facebook is, basically.
After about five minutes, Zuckerberg concluded there wasn’t anything to be gained from sitting there any longer. The young billionaire had allocated an hour for the meeting, and Iovine had burned through most of that before he even entered the conference room.
“Sorry, I have a hard stop at three thirty,” Zuckerberg declared. “I’m not sure what we could actually do together, but I appreciate you coming here. Nice to meet you, and I’ve got to go.”
Though the meeting proved unproductive for all involved, Wallach and Iovine would both find a way to get in on two of the next big platforms for musicians, Spotify and Apple Music. And, thanks in part to Wallach, several A-List Angels—along with a host of other creators—grabbed their piece of the streaming revolution as well.
One day in 2006, Iovine went for a seaside stroll in California with longtime pal Dr. Dre. They started discussing a shoe deal the superproducer had been offered, not dissimilar from the ones Jay-Z and 50 Cent had inked several years earlier. “Fuck sneakers,” said Iovine. “Let’s sell speakers!”2
And that’s more or less what they did. Iovine and Dre initially teamed up with Monster Cable Products’ Noel Lee to design, engineer, manufacture, and distribute headphones, giving him a mid-single-digit stake in their company, Beats by Dr. Dre. Smaller stakes went to the Black Eyed Peas’ Will.i.am and NBA star LeBron James; Iovine and Dre held the largest. Universal also received a piece of the company, encouraging its biggest stars to place the headphones in music videos—especially acts on the Iovine-helmed Interscope, one of Universal’s top labels. By the end of the 2000s, Beats were popping up on famous heads from Lady Gaga to members of the U.S. Olympic basketball team.
Around the same time Dre and Iovine took their walk, two men who’d just started a music streaming company were yelling gibberish at each other in an apartment in Stockholm, hoping to stumble upon a nonsensical name that hadn’t yet been used anywhere else on the internet. Daniel Ek misheard his cofounder, Martin Lorentzon, thinking he’d said “Spotify,” and found zero Google hits for the name. The Swedish serial entrepreneurs—Ek in his twenties, Lorentzon in his late thirties at the time—hired engineers to design an interface and spent two years trying to convince European labels to license their catalogs. The service still reeked of Napster to many, and it wasn’t until Spotify’s founders proffered million-dollar advances that the labels relented.
“We bet our personal fortunes, and sometimes we bet the entire company,” said Ek. “We led with our conviction rather than rationale, because rationale said it was impossible.”3
Record sales had declined precipitously in the post-Napster universe following their 2000 peak of 785 million U.S. album sales. Though the advent of Apple’s iTunes store in 2003 offered a bit of relief, the service also trained consumers to buy music by the $0.99 single, rather than album to album. Total sales dropped 45 percent from the beginning of the new millennium through 2008. By the time Spotify came along, the major labels had gotten desperate enough to mull ideas once considered unacceptable.
Spotify’s success in Sweden, where it reversed a decade of industry-wide declines by 2011—accounting for half of the country’s recorded music revenue from a combination of free and premium subscriptions—caused the majors to give Ek a long listen. Some may have regretted not striking a deal with Napster to create a Spotifyesque service a decade earlier. The majors didn’t seem deterred by the involvement of old foe Sean Parker, who reportedly paid $15 million for 5 percent of Spotify in 2010.
In any case, the major label executives knew they held a great deal of leverage, given that there could be no Spotify without access to the virtually unlimited buffet of music their catalogs offered. And, like the creators who’d watched companies such as Facebook and YouTube grow, they wanted a piece of the platforms themselves. They decided to bargain accordingly, eventually amassing about 10–20 percent of Spotify. The labels’ blessing cleared the way for Ek to raise $100 million at a valuation of around $1 billion ahead of Spotify’s U.S. launch in 2011.
“He solved the puzzle and gave people an incredible platform, with all the music you can eat and with the most incredible interface, and changed the game,” says Oseary. “Of our many investments, we haven’t made many in our core community. [With Spotify] we saw something in our world and jumped in on it. And understood the potential: if the record companies supported it, we could see where it could go. And they did, and the rest is history.”4
Wallach wasn’t able to link Facebook and Interscope, but he’d soon find a way to help foster another intersection of technology and creativity, something he’d almost been designed to do. He grew up in Wisconsin loving computers and music, uniting the two in high school as an audio engineer (“which is, essentially, basically, primarily computer programming,” he argues).5 Wallach didn’t think much about business until college, when he started to contemplate how he might begin to monetize his music with Chester French (Zuckerberg was an early fan).6
“We were part of the first generation of artists that built its audience mainly through social media, not mainly by driving around in a van,” says Wallach. “I didn’t choose for these technological things to happen in my early career, but they did. And my early trajectory was driven by my choice to embrace those things, and really think from the beginning about, ‘What does it look like to build a band in a social media world? What does it look like to make recordings in a digital recording world?’”7
In 2007, Wallach moved to Los Angeles, where his music career took a promising turn. Pharrell Williams heard Chester French and signed the band to his Interscope label, releasing its first album, Love the Future, which peaked at No. 77 on the Billboard charts in 2009. Through a mutual friend, Wallach met fellow midwesterner Kutcher, who’d snagged a piece of Popchips—the snacking love child of rice cakes and potato chips—shortly thereafter. The next thing Wallach knew, he was negotiating with the company’s executives as they rolled out an influencer marketing campaign.8
“They were raising money and they go, ‘Do you want to invest in us?’” Wallach recalls. “So I put five thousand dollars into Popchips…I’d never done this before. Five thousand dollars was a pretty big purchase for me. And it wasn’t tech; it was a potato chip company.”9
For Wallach, the investment represented a way to establish a foothold in the venture capital world, even if it wasn’t the ideal company for him. (Today, is his outlay worth $1 or $20,000? “No idea,” he says).10 If he’d waited a little longer, Wallach could have made a much better first investment. The year after tucking into Popchips, he was still living in his mother’s house in Milwaukee when he received a call from Shervin Pishevar, then working at Menlo Ventures in Silicon Valley.
“I remember him calling me about Uber: ‘Hey, do you want to put a little fifty grand in?’” says Wallach. “I’m sitting there in my boxers at my computer with Shervin on the phone, and I’m like, Fuck, I don’t want to sound like I don’t have any money, but I can’t make a $50,000 investment. I barely have $50,000. So…I may have overweighted my skeptical theories of the company.”11
Wallach’s self-imposed pessimism faded as Uber’s valuation climbed from $300 million into the billions while he toured the world with Chester French—sometimes drawing decent crowds, but playing audiences as small as just a few people in one unfortunate tour stop in Bristol, England. Wallach itched for a way to delve deeper into startups—and found one in Spotify, which he first discovered in 2010, pestering early investor Shakil Khan for an introduction to Daniel Ek and Sean Parker. The young musician was impressed by the combination of the two (“Daniel was just so rational and so level-headed and kind of unemotional.…Sean had created the whole space, and he was a maniac and he was one of the best salesmen I’d ever met, and brilliant”).
Wallach desperately wanted to invest, but he still didn’t have enough cash to buy a meaningful stake. So he struck a deal: he would come on as Spotify’s artist-in-residence, serving as an ambassador to musicians. That meant working to create things like a dashboard that could tell acts where their streams were coming from, which could help prevent costly occurrences like Chester French’s Bristol debacle. In exchange, Wallach would be “significantly paid in equity,” grabbing a slice of a company already worth nearly $1 billion.
Even more importantly, Wallach became an evangelist for Spotify in a way that Pishevar had for Uber, especially after he set about raising a party round of his own in 2012. Three years earlier, Chester French had released a song with Diddy called “Cîroc Star,” an ode to Las Vegas partying that featured the hip-hop mogul and his Diageo-backed vodka, so Wallach called him up and extracted an investment.
Diddy was one of many creators Wallach brought along, but Spotify wasn’t necessarily an easy sell—particularly to artists who’d gotten hosed in the Napster era. Still, a handful saw a rare chance to own a piece of the platform that represented the future of their industry. Wallach helped the company ink deals with rocker Jack White, rapper Eminem, Blink-182 drummer Travis Barker, teenager Justin Bieber, and manager Scooter Braun, raising about $15 million in total. Braun was one of several prominent artist managers to grab a piece of the platform, and the involvement of his ilk didn’t sit well with everyone.
“I think they are actually distractions,” said venture capitalist Fred Davis, a founding partner at investment group Code Advisors. “Are they misusing their platform as a representative to an artist to sweet-talk their way into investment deals they should not be a part of, or are they good investors? Good investors provide value.”12
For Spotify, however, the support of managers and artists alike proved to be of immense value as the company continued to expand. Even though the labels licensed their catalogs to the streaming service, such deals generally have a defined term—meaning that the labels had lots of leverage when it came time to re-up. With high-profile managers and their clients holding stakes in Spotify, though, Ek and his pals had valuable supporters.
“It’s good to have a bunch of musicians investing in Spotify,” says Brian Zisk, cofounder of the SF Music Tech Fund and conference. “It’s really good to have when you’re theoretically gonna come under attack from an industry, to have the bread-and-butter folks of the industry involved.”13
While Spotify fought to establish itself in the U.S. market, Iovine and Dre busied themselves looking for new sectors to conquer beyond headphones, where Beats now controlled two-thirds of the premium side of the market. They’d gotten there by establishing headphones as a fashion accessory. As Best Buy’s chief, Brian Dunn, explained: “The consideration set [is], ‘Do I buy the Beats or the Air Jordans?’”14
Dre had found a way to compete with sneaker brands without even entering the shoe business as he’d planned before his seaside chat with Iovine. The pair received plenty of help from other famous stakeholders, including Will.i.am, LeBron James, and Diddy, all of whom displayed the Beats brand prominently in their highly scrutinized daily lives. And, after gobbling up music service MOG in 2012, Dre and Iovine employed a similar formula for streaming. Beats hired Nine Inch Nails front man Trent Reznor to head up the creation of its answer to Spotify, Beats Music, which debuted in early 2014; Ellen DeGeneres starred in an early commercial for the service.
Apple, meanwhile, was still mourning the loss of Steve Jobs, who passed away in 2011. Yet his death opened the door to a new plan for distributing music. According to Troy Carter, Jobs said in 2010 that the populace would never fully adopt streaming, and that people wanted to own their music. His successor, Tim Cook, had a different philosophy—as revealed by his decision to buy Beats for $3 billion in the spring of 2014.15
In addition to bringing the world’s most popular premium headphones into Apple’s fold along with Iovine and Dre, who joined the tech giant’s staff, the acquisition brought Beats Music itself into Apple’s core. The following year, the company launched Apple Music to battle Spotify, abandoning the digital download–first mentality that built the once-vaunted iTunes and its online store in favor of the streaming model launched by a team of creators headed by Dre and Reznor.
The deal underscored the gargantuan size of Apple, a company worth many hundreds of times what it paid for Beats, but it also showed the entertainment world once again the value of ownership. At the time of the deal, two veteran music producers—Dre and Iovine—took home centimillion-dollar checks; Will.i.am and LeBron James pocketed double-digit millions for their troubles. Thanks almost entirely to the Apple buyout, Dre clocked $620 million in pretax pay in 2014, by my estimates for Forbes, the highest single-year total tallied by an entertainer in recorded history to that point. These individuals had gone from rich to wealthy.
With Dre wrapped up in Apple Music and Diddy ensconced in Spotify, Jay-Z remained the last of hip-hop’s three top moguls (who also happened to be the three wealthiest musicians in America) without a significant financial interest in a streaming service. Jay-Z quietly went to work securing a platform of his own; one of his lieutenants pointed him toward Aspiro, a publicly traded Scandinavian company home to two tiny streaming services, Tidal and WiMP. In late 2014, an employee in Aspiro’s Oslo office got a call from someone acting on behalf of a wealthy U.S. investor interested in buying the struggling company (and thought it might be Donald Trump).16
As the year came to a close, Jay-Z emerged as the mysterious bidder—and bought the publicly traded Aspiro for $56 million, about 60 percent more than its open market value. At the time, most of Spotify’s musician-investors hadn’t been revealed (Diddy, for one, didn’t get outed as a stakeholder until the publication of my book 3 Kings). Apple Music had musicians like Dre in the fold, but it wasn’t an artist-owned company by any stretch. Jay-Z decided to distinguish his streaming service from all rivals by positioning Tidal as a company owned by and built for artists.
Other musicians had tried to create their own distribution systems in the past, with little success. In 2001, Prince launched something called the NPG Music Club. For $100 per month, the service would distribute new music directly to fans, provide early access to concert tickets, and offer a fan-hosted radio program. Prince lowered the price to $25 for a lifetime subscription before shuttering it altogether in 2006.17 Eight years later, Garth Brooks tried launching GhostTunes, a digital music store; he shut it down in 2017 after striking a multimillion-dollar deal with Amazon to bring his music to a streaming platform for the first time. “It’s no secret to anyone that I’m very involved in my business,” Brooks subsequently told me. “I know enough just to be dangerous…[but] my job is the fun.”18
Jay-Z aimed to differentiate his plan in typically bold fashion, holding a press conference featuring his roster of artists as they officially signed on as musician-owners. The lineup was impressive on paper if a bit awkward on stage: the masked DJ known as Deadmau5 whiffed on a high-five as he greeted Madonna, while country star Jason Aldean and rocker Jack White looked about as comfortable as in-laws meeting for the first time. Jay-Z, Kanye West, and J. Cole struck identical hands-in-pockets poses, and Beyoncé smiled uneasily next to the silent, chrome-helmeted duo Daft Punk. Coldplay front man Chris Martin and superproducer Calvin Harris joined via videoconference, making the event feel as much like a standard corporate sales meeting that happened to take place on Halloween as a gathering of musical superheroes.
Things got stranger as the Tidal investors all came up to sign some sort of document. Madonna suggestively slung her leg over a table as she added her signature, while Kanye West made a vague analogy to oil exploration and Alicia Keys quoted Nietzsche (“Without music, life would be a mistake”). Surreal as the event may have been, Jay-Z lured each artist with a very tangible offer—a low-single-digit percentage stake—in exchange for promises of exclusive content.19 It seemed he figured that was the best way to compete with Spotify and Apple Music, while granting artists an opportunity to own the next big streaming platform outright. “Right now, they’re writing the story for us,” Jay-Z said of the music industry’s established power players. “We need to write the story for ourselves.”20
He also took a different path than Spotify, which had to hand over a significant chunk of itself to the labels to get the licenses needed to stream an unlimited amount of music. In Tidal’s case, the process happened over a matter of months, not years—perhaps in part because the labels didn’t want to ruffle the feathers of some of their biggest stars. Indeed, Jay-Z’s roster included multiple acts from every major label and several indies.
But getting traction proved tricky. Even after a stream of exclusive releases from Jay-Z, Beyoncé, and Kanye, Tidal kept losing money—double-digit millions annually, according to numerous reports, with a few million subscribers by the end of 2016. That was a fraction of Spotify’s and Apple Music’s totals, and even that ballpark number seemed like it could be overstated (according to a pair of Norwegian business journalists who wrote an exposé on Tidal a year later, the real number of active users was probably closer to 1 million at the time; the larger numbers probably included inactive and closed accounts).21
In January of 2017, though, Sprint pounced on Tidal, investing $200 million for one-third of the company, and giving Jay-Z a corporate partner to cover the bills. The deal also gave him a tenfold on-paper profit, though only time will tell how wise his gambit was. Regardless, Jay-Z’s moves with Tidal represented a fascinating turn of events in which a creator had become wealthy enough to be on the other end of the content-for-ownership trade, doling out pieces to musicians who were merely rich. Interestingly, for a hip-hop star who’d once invoked Chris Rock’s famous bit by rapping “Fuck rich, let’s get wealthy,” Jay-Z’s strategy mirrored the comedian’s formula for spreading generational prosperity: Walmart’s owners pass down wealth by building new Walmarts, not by frivolously spending their cash.
“The equity ownership…that’s really important philosophically, not just from a dollars and cents perspective,” Jay-Z said. “All artists who come in—and this is an open platform, an open invitation—will participate in the equity upside. And that is important, too, because of that participation in the process, by having a board seat, by actually being an owner in this. It’s a different type of involvement.”22
While Shawn Carter busied himself doing battle with Spotify, another crucial Carter in the music business—Troy—would find a home at Daniel Ek’s streaming company as global head of creative services. But first, he had to be convinced of Spotify’s merit by Wallach.
The two first bonded in 2008 at a twenty-second birthday party for Solange Knowles (Beyoncé’s sister), where Chester French had played a set. Carter was so impressed with Wallach that he brought his band along on Lady Gaga’s Fame Ball Tour the following year. Afterward, Wallach took Carter on a hike in Los Angeles. The latter was still managing Gaga at the time (they parted ways in 2013) and felt ambivalent about Spotify.
“Troy and I had a two-hour hike deeply debating,” says Wallach. “At the end of it, Troy tentatively was down with what Spotify was trying to do.”23
Carter’s skepticism revolved around Spotify’s ability to get licenses around the world, much of which came down to the whims of the major label chiefs. Once he realized they were on board, he was, too—so much so that he invested in the company. The more he got to know Ek, the more he realized he agreed with the Spotify founder’s vision of where the music business needed to go. Soon Carter was fielding calls from other managers who were skeptical about bringing their artists onto the platform; his conversion made him a potent evangelist. In 2016, Carter joined Spotify full-time.
“It’s just one of the rare times that musicians have been able to capture value from one of the companies that captures value from them,” Carter says of the streaming service. “I think it was a great opportunity for the artists.”24
The bonanza wasn’t limited to musicians. Diddy introduced Wallach to Burkle, which led to an investment with his A-Grade cofounders. Kutcher quickly inserted himself into Spotify’s inner circle, befriending Ek and peppering him with ideas. A devoted Spotify user and avid jogger, Kutcher pointed out that there wasn’t a way to listen to music with his smartwatch.
“I’m calling Daniel going, ‘Dude, hack me together an application for my Moto 360 so I can listen to my Spotify offline, on my watch, with my Bluetooth [headphones],’” he recalls. “So we were trying to work out something there.”25
Wallach had emerged as another useful conduit between the worlds of content and technology, helping Spotify do what Napster couldn’t: win over scores of musicians, particularly the high-profile sort who could torpedo the service with vocal complaints or lawsuits (of course, plenty of musicians remain skeptical of Spotify’s model to this day, but not enough to sink the service).
At the same time, Wallach served as another example that one needn’t be a billionaire venture capitalist or a megastar celebrity (or her manager) to grab a piece of the action. Along the way, he began to develop an investing methodology of his own, through a series of steps. First, he would dig deep into every company he considered, trying to come to a complete understanding of the markets in which they operated, avoiding those he couldn’t comprehend. Of the ones that piqued his interest, he’d spend time with management, talk to competitors, look at their financial models and sometimes build his own.
“You learn what different types of investment instruments mean in terms of the rights they give you as an investor and the liquidation preferences, and what will happen in different scenarios,” he says. “They’re the difference between you getting paid back your money or not, or getting a return or not, or getting diluted to hell. If you don’t know any of that stuff, you can be screwed very easily. There are a lot of snake oil salesmen.”26
Over time, he devoted more and more of his time to investing and less to music. Chester French released its last album in 2012 and it failed to chart; Wallach’s well-reviewed solo project, Time Machine, suffered the same fate in 2015. “He was just a multitalented individual who was also a musician,” says Zisk. “He seems to have done better as an investor than as a musician.”27
Wallach’s pal Burkle seemed to agree. The billionaire had been winding down his A-Grade investing activities with Oseary and Kutcher and was looking for other ways to pour money into the startup world—so he gave Wallach a call. In 2015, the duo started a fund of their own, dubbed Inevitable Ventures. There, Wallach has since gravitated toward businesses much more esoteric than Spotify. Among them: Glympse Bio, an MIT spinoff that uses advanced sensors for early disease detection, and 8i, which creates holograms of humans for use in augmented and virtual reality.
At the same time, Wallach has been thinking about the model for the modern creator-owner in the context of his light reading, like Thomas Piketty’s Capital in the Twenty-First Century. “His fundamental point is that the reason you get inequality in capitalism is because the returns on capital are much greater than returns on labor, and the growth over time in the returns on capital are much greater,” says Wallach. “In other words, having wealth has become a greater asset over time than it used to be. And relatively, labor has become a less valuable asset. I’m still in the process of going from being primarily a laborer to being a capitalist.”28
As Wallach and I wrap up our interview in his living room, he lets me in on another reason he gravitated toward investing with Burkle rather than the sorts of creators he helped bring into Spotify. Wallach enjoyed helping artists pile up equity, to be sure. But he found a poignant element at the intersection of creativity and capital, something he likens to a fictional fan going backstage to find Krusty the Clown (of Simpsons fame) chain-smoking cigarettes.
“All these artists I really admired as artists were just being dragged into this gutter of money conversations,” says Wallach. “These people are my creative idols and they kind of existed in this untouchable, platonic realm of pure art…even though they’re artists, they live in the economy, too, and they have to survive. And they have to think about money just like everyone else does in the world. And it was so sad to me to see them preoccupied with this stuff.”
As Wallach looked on, the desirability of startups as an investment roared back from post-recession lows amid the ensuing bull market. With governments around the world keeping interest rates low to boost what seemed at first to be a fragile recovery, stocks soared toward new heights, leading scores of wealthy investors—including individuals and government entities from Russia, China, Saudi Arabia, and elsewhere—to seek value by plowing cash into venture funds.
These outlays weren’t limited to the usual Bay Area suspects. SoftBank, the giant Japanese venture firm, raised $45 billion from Saudi Arabia for its Vision Fund; the kingdom has aggressively pursued other avenues toward startup investing, though most Silicon Valley outfits won’t reveal their backers publicly. Some don’t even accept investments from American public pension funds, probably because the required disclosures might reveal more about their investors than they’d like.29
In any case, the influx of capital helped push the demand for targets of venture dollars past the supply of worthy companies. “Relatively speaking, it put the entrepreneur in a greater position of power than the investor,” says Wallach. “With the exception of marquee firms like Sequoia and Andreessen Horowitz, the power dynamic went from ‘We’re a little startup; we’re so lucky to get Ashton Kutcher tweeting about us’ to ‘Jared Leto, you’re lucky if we let you put money into this thing,’ as if it’s risk-free, which is insane.”30
As such, the best startups became even stingier with free or discounted equity. But on account of the groundwork laid by early A-List Angels, savvy creators continued to find good startups—and in some cases launch their own.