Teach Me How to Startup

Mo’ Money for Rap Genius: Impish Ivy Leaguers Raise Millions for Internet Decoder Ring

How three Yale alums convinced Silicon Valley's most powerful VC firm that they could explain everything.

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Tom Lehman, Ilan Zechory and Mahbod Moghadam, from left. (Photo: Sumner Dilworth, courtesy of Vibe)

Visitors who search for Harlem rapper Azealia Banks’ breakout hit, “212,” on Rap Genius, an online platform that crowd-sources explanations of hip-hop lyrics, will find nearly every verse annotated by the site’s users, who clocked more than 2 million monthly uniques in August, according to comScore. Click on the line “Now she wanna lick my plum in the evening / And fit that ton-tongue d-deep in,” and a pop-up immediately appears explaining that Ms. Banks is employing a metaphor for cunnilingus and that “She stutters the words tongue and deep to mimic the stuttering that occurs when one receives such a gift.” That exegesis received 11 upvotes, earning the contributor jamima-j, a female “slam poetry writer,” a healthy bump in “Rap IQ” points on the site.

Readers might find her analysis either amusing or unnecessary. But the reigning kings of Sand Hill Road, venture capital firm Andreessen Horowitz, view Rap Genius as “one of the most important things we’ve ever funded,” co-founder Ben Horowitz told Betabeat last week. The prominent V.C. firm, which clawed its way into the Silicon Valley firmament in just three years by aggressively plowing millions into fast-growth tech start-ups like Facebook, Pinterest, foursquare and Airbnb, often at towering valuations, were the sole investors behind the site’s $15 million Series A.

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Mr. Horowitz (Photo: C Flanigan/Getty Images)

“When I first brought it up, [Marc Andreessen] kind of laughed at it,” admitted Mr. Horowitz, the rare V.C. who can quote the appropriate Rick Ross rhyme for every occasion.“He was like, ‘Really? Rap Genius?’”

The site’s potential finally clicked for Mr. Andreessen after he used it to try to understand the Kanye West and Jay-Z song “No Church in the Wild.” Click on the lyric “Is Pius pious because God loves Pius?” and the site walks you through Plato’s Euthyphro, Pope Pius and Immanuel Kant. “It’s a big philosophical question just, like, dropped in the middle of a Jay verse,” Mr. Horowitz said with admiration.

Despite the platform’s name, contributors have already used Rap Genius to annotate a number of texts outside the world of hip-hop, including the Supreme Court decision Plessy v. Ferguson, the Mayflower Compact and the Digital Millenium Copyright Act. Last week, author and NYU professor Clay Shirky added the iTunes terms of service for dissection. Users obliged by appending a cartoon of The Human Centipede.

After the Jay-Z song, Mr. Andreessen went on to read annotations of The Great Gatsby contributed by high schoolers whose teacher added chapters to the site. His favorite part, Mr. Horowitz said, was a reference to old money versus new money that read, “In the days of The Great Gatsby, it was better to have old money, unlike today, when it’s better to have new money.”

No doubt the investor and Netscape co-founder, who was photographed on a gold throne for Time’s “Golden Geeks” cover in 1996 and recently named No. 2 on Forbes’ Midas Touch list of tech investors, appreciated that reading.

Mr. Horowitz’s abiding obsession with rap has been well documented. He notoriously starts every post on his business blog with a couple of expletive-laden lines from his favorite MCs and has nicknamed his partner, Mr. Andreessen, Big Tunechi, in reference to Lil Wayne’s childhood nickname (just ask @LilTunechi’s 8.7 million Twitter followers), because he thinks the two moguls are similarly prolific. It ultimately fell to “Big Tune” to articulate the site’s grander vision: turning Rap Genius into an “Internet Talmud” that, Mr. Andreessen said, will drop the same “knowledge on knowledge” in other arenas, like law, the Bible, poetry and even country music—to eventually “annotate the world.”

The site’s three 20-something co-founders are currently beta-testing the idea of rolling out those content areas into separate verticals: Stereo IQ (for indie rock), Poetry Brain, Country Brain, Law Genius and Bible Genius.

“The criticism is: ‘Ben, I can’t believe you’d invest in something so frivolous as rap,’” Mr. Horowitz acknowledged, but he pointed out that Andreessen Horowitz engendered the same eye-rolls when the firm was part of a $2.75 billion deal to buy Skype from eBay. Two years later, Skype was sold to Microsoft for $8.5 billion. “People who kind of understood the basics [of that deal] were like, ‘Oh, that’s stupid. Those guys are idiots.’ But if you looked a little deeper and saw what was really going on, you would say, ‘Well, this is a magical opportunity.’”

Rap Genius’s co-founders, who met as undergraduates, have been expounding on the idea for some time now—that the Internet needed this kind of pop-technology, a Rosetta Stone by way of Urban Dictionary, to decode the Western canon—but it wasn’t until Andreessen Horowitz came along that anyone believed them.

If you spend any time with the trio, you can understand the skepticism.

As their origin story goes, the co-founders were treading lucrative career paths when they started the site, first called Rap Exegesis, as a side project. Tom Lehman was an engineer at the hedge fund D.E. Shaw. Ilan Zechory was a project manager at Google and a former writer for Deadwood, and Mahbod Moghadam, a Stanford law school grad, was on deferral from the law firm Dewey & LeBoeuf.

In 2009, deferral was code for a recession-related year off for a fraction of the salary. With his free time, Mr. Moghadam was slated to start a free internship with Warren Buffett when Berkshire Hathaway found his blog, Beneficent Allah, in which he had drafted a satirical billable memo referencing the “Ballstate Insurance Company” (Allstate was a client) on “the probabilities of inheriting the Earth.” Mr. Buffett’s conglomerate didn’t appreciate the irony, and neither did Dewey. The same day he was fired, Mr. Lehman built the site.

“We’re more into writing than underwriting, you feel me?” Mr. Moghadam told Betabeat last week, sitting in the start-up’s new headquarters: a penthouse apartment in Williamsburg overlooking the East River.

Mr. Lehman, whose actual apartment is four floors down, had returned moments earlier with three trays of sushi for the team’s dinner. A handful of the company’s fresh-faced 20 to 30 employees were unwinding in the back bedrooms.

Mr. Moghadam was sporting a striped button-down and walnut-colored dress shoes that came to a masochistic point. He introduced Mr. Lehman as a “swagged-out Mark Zuckerberg,” but between Mr. Lehman’s upswept column of curls, electric blue T-shirt, neon Nikes and sweatshirt from A Bathing Ape, he looked more like a dubstep deejay just in from Tel Aviv. Mr. Zechory, in emerald green Nikes and a pastel button-down, fit somewhere in between.

Months before they raised that Series A, another New York start-up entrepreneur described the braggadocious trio of Yale graduates, who sometimes borrow the vernacular of the rappers they admire, as “total characters and a pile of contradictions”—a representation that speaks to their awkward, if so far potent, positioning at the nexus of the tech and hip-hop worlds.

Sitting in the living room, amiable and unguarded, the co-founders seemed to suffer from the interloper’s dilemma: They’re one “swag” too cocky for the tech scene and a “tight” too Ivy League for the rap game.

Up until last month, outside of verified accounts from artists like Nas, 50 Cent and 2Chainz, the start-up was best known for two things. The first was an essay in The New York Times magazine that devoted considerable column inches to critiquing Rap Genius’ “wrongheaded conclusion” that every hip-hop rhyme had or was in need of an academic annotation.

The second was a misguided late-night video of a shirtless Mr. Moghadam mocking the rap group Das Racist, who met at Weselyan, after one of the MCs equated Rap Genius with “white devil sophistry.” The closing line? “I’m trying to dis you, but you ain’t even famous. You’re like a slim anus.”

“I’m embarrassed of my freestyle dis,” Mr. Moghadam admitted of the video. “I want to take it down, but these guys say, ‘Hey, it’s a meme now!’” He added, “My body looks all right, but I can do much better raps than that.”

Mr. Horowitz acknowledged the trio’s bluster. “They have a real personae-slash-performance art to them,” he said. “They play the part. It took me a little bit to get past the surface pretense, just because it is so unusual. At least in my world—in the tech world.”

“We used to want to be writers and artists and stuff like that,” Mr. Zechory said, when asked about the team’s self-presentation. “Then we got really busy working on Rap Genius, and we realized it’s all folding in on itself, and we have to never break character.”

That routine has gotten them this far. In fact, Andreessen Horowitz wasn’t the only firm eager to fund their vision.

“There were definitely other investors who gave them term sheets, and there were other investors who thought that it could be important, but in their minds, nobody else quite understood it or quite understood them, you know what I mean?” said Mr. Horowitz.

Rap Genius was the fastest-growing start-up in its class at Y Combinator, the archetypal Mountain View incubator. (Mr. Zechory says their Quantcast numbers show 10 million uniques, but that account has been made private.) During their three months in the Valley, “The elders were kind of wary of it,” said Mr. Moghadam. “They’re starting to come around now that they realize we’re gonna make a shit ton of money.”

That last claim remains to be seen. After all, despite its ubiquity in search engine results, Urban Dictionary is still primarily a website that sells ads.

Rap Genius’ business plan also calls for selling advertising, but according to the latest numbers from comScore, the site members occupy an industry sweet spot. Sixty-three percent of users are 18 to 34, 66 percent of them are male, and 29 percent boast a household income of $100,000 or more.

“We are gonna do the dopest ads of all time,” Mr. Moghadam declared, but they have other potential revenue streams in mind as well. “Law firms will pay $100K a year for Law Genius Premium,” he insisted over email. “Lexis and Westlaw are jank—you go from one case to another, and it’s sloppy and wack. … Law Genius will be legal footnotes on crack! Also it can include anything—video, audio—instead of simply citing a Supreme Court case, you can embed the oral arguments!”

And then there’s the merchandising. “Girl, we finna have an entire store of gear for each site,” he wrote in an email that could benefit from some decoding itself, “not just shirts, you can get a Rap Genius onesie, a Poetry Brain parka. …” The possibilities were endless.

Rap Genius has been remarkably successful in getting rappers to sign up to explain their own double entendres, regionalisms and allusions, partly by hosting the artists at Rap Genius headquarters both in Williamsburg and a villa they rent in “far Malibu,” where Mr. Moghadam said RZA and Black Cobain have both stayed.

The company is planning on moving closer to Los Angeles’ city center. “So with the Hollywood house, we’re always going to have rappers living with us,” he wrote. They even offer visitors use of a studio. “Our recording is decent; it’s not wowzers, but it’s pretty dope,” he added, explaining that it was more of a “chill vibe type situation.”

Earning the trust of the rap world wasn’t easy. A breakthrough was provided by 50 Cent’s former manager, the late Chris Lighty—“R.I.P.,” said Mr. Moghadam, tapping his heart twice. Over lunch a couple of months ago, Mr. Zechory recalled, Lighty “was like, look, if you want 50 Cent to gamble on Rap Genius, just get Nas to do it. Because 50 Cent will see Nas doing it and be like, ‘O.K., cool.’”

In a similar vein, it was Troy Carter, Lady Gaga’s manager and a start-up investor, who encouraged the founders to come up with their “verified artists” section.

It remains to be seen whether Rap Genius will have the same luck with indie rockers. Mr. Moghadam said that he tried talking to Chan Marshall, better known as Cat Power, into explaining her lyrics when he ran into her in L.A. “She was like, ‘I don’t want anyone to know what these mean! It’s so deep to me! Get away from me,’” he said, his voice dropping to a stage whisper.

Had he tried Fiona Apple? we asked. “She’s my queen,” Mr. Moghadam responded, wistfully. “Fiona Apple, if I could, I would just want to take her to sushi. I know what [her lyrics] mean!”

If Rap Genius succeeds, it will be because its founders have no other choice, a dynamic that happens to be of the V.C. firm’s investment criteria, said Mr. Horowitz. “Their whole lives are dependent on them making this work, right? They are all-in,” he said with a laugh. “It’s not like they’ll go work at Facebook! Nuh-uh. This is it. They have to make this work. And we love that.”

ntiku@observer.com

A version of this story appeared in the Oct. 17, 2012, issue of The New York Observer

Follow Nitasha Tiku on Twitter or via RSS. ntiku@observer.com

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