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Get to Know a C.E.O., with Ilan Zechory

If there is one thing we can all agree with across the education landscape, one facet of the learning experience with which even the most flamboyantly progressive reformer and the staunchest traditionalist would find common ground, it is that sparking a child's interest is the surest way to drive academic success. If a student can find a passion to latch onto, they have a natural incentive to explore the depths of their brain, soak in knowledge, and (mostly important) try hard.

My sometimes co-author Matt Greenfield has a parable of sorts he likes to tell from his professorial days at CUNY that I am likely about to butcher something fierce. It goes as follows: he once had a student that was clearly a bright young man, but was also clearly a poor writer lacking in basic argumentative structure. Matt took him aside and asked, "What is it that interests you in life? What is your passion?"

The answer, as it turns out, was cars. While the student did not think he could write, he was confident in his knowledge of the ins and outs of an automobile. So Matt assigned him the project of explaining why it was he loved cars so much. After refining that piece, Matt then had the student write a research piece explaining the pieces of an engine and how they work together. From there, a piece on how the shape of a car can influence aerodynamics and yield better performance around a sharp turn. On and on this went, until by the end of the semester, the student was right in line with his class: a true writer that could outline a thesis and concretely back it up with data points and grammatical structure. Matt then tasked the student as follows: learn about an auto-mechanic for a NASCAR team, find out the necessary steps it took for that mechanic to reach his chosen profession (from calculus to engineering to various certifications), and outline a path you need to take in order to reach this end goal.

True, the student had managed to eschew the traditional curriculum that called for essays focusing on a predetermined literary set; but what was the goal of that student's education? Was it to retain knowledge surrounding the courtship of Petruchio and the shrewish Katherina, or was it to develop a set of critical thinking and expressive skills that will carry him through his career?

Tapping into a student's passions is undoubtedly the surest path to learning without the student even realizing it, which leads me to introduce a company that has gained amazing traction and a cult-like following (not to mention $15 million in venture funding from the likes of Andreessen Horowitz) in just a few years: Rap Genius. While on the surface the site is merely a crowd-sourced directory of rap lyrics and their meanings, the reality is the platform has morphed into a vibrant community of critics debating everything from hip hop (before you scoff, I would argue that if Bill Shakespeare were around today, he would make his home on 106 and Park) to Warren Buffett's letters to his shareholders.

I recently met with Ilan Zechory, one of Rap Genius's co-founders alongside Mahbod Moghadam and Tom Lehman (Author's Note: not him), to discuss the site's transition to the education space (Ilan is the one rocking the tan robe and woodman's button down in this video). While not quite as wild as their reputation may suggest, it was none-the-less an entertaining conversation.

This intro has gone on for long enough, and there is still much to get to. I will now quit my rambling. Let's get to know Ilan Zechory:


Elevator pitch: what is Rap Genius, and what problem are you trying to solve?

Rap Genius is... a lot of things. It's a Wikipedia of annotated texts that started out as a side project for annotating rap lyrics. It was just a few friends talking about rap lyrics and throwing out interpretations, interesting historical information, and poetic analysis. It quickly grew and expanded to music beyond rap, music in other languages, non-musical texts like poetry. Before we had 15 songs on the site, there was a Bob Dylan song. Before there were 50 songs, there was an Emily Dickinson poem. We started noticing that people interested in annotating rap were really interested in annotating lots of different stuff, not just rap. Rap was obviously a fruitful place to start for annotation because it is so dense - there's a lot of wordplay and reference and whatnot.

So Rap Genius has grown and expanded into a platform for annotating all sorts of texts. It's not just a platform in terms of a technology (as hard as the technology has been to develop - and it's important to make the technology very good), it's more like a movement, a community, and without the people it would be nothing. There are hundreds of thousands of contributors worldwide who add annotations to the site, and there's a core of about 1,000 editors who are really obsessed with the site, who edit other people's work to make sure it's good quality. Then there is a core of about 150 top moderators who find other editors and do a bunch of the hardcore editing work. These guys are up all night on email lists and various groups making sure Rap Genius is a healthy community.

How does moderation work? Who are these people, and how do you incentivize them to drive usage?

It's a combination. There is some stuff on the product that gives you literal incentive, like RapIQ, which is the point system we have. It started out fairly crude, but it's actually quite sophisticated now as a measure of the quantity and quality of your annotations. So if you leave an annotation and I upvote that annotation, you are going to get some RapIQ because I am a reputable member of the community. If some new user comes and upvotes it, you will get some RapIQ but not as much as if an editor upvoted it. Further, if you leave an annotation and someone else edits it, and there's a final product that is basically half your doing and half someone else's, you two will split the RapIQ boost.

It's a pretty sophisticated system for basically acting as a proxy for how much knowledge you have imparted on the Rap Genius world, and people really respond to that.

More than that, there is a lot of personal relationship stuff to it. The site is still small enough that the main moderators tend to know who the other moderators are. They know each other through the Rap Genius Forum and through the live chat on the site, through interacting and having debates on the actual lyric pages. There is also some social infrastructure built out where if you leave an annotation and I come and edit that annotation, you are going to get a notification. If you're on Facebook, you have that little blurb that pops up to see that someone liked your photo. On Rap Genius, you are going to see if someone liked your annotation. You will click through and see who they are, what kind of stuff they have been annotating. You might want to leave that person a message, or get into a discussion about the lyric itself. Then a moderator might come in and synthesize that discussion into one final product. We are trying to facilitate debate, but we want that debate at the end of the day to spit out a really interesting "one" thing for somebody to read, rather than exposing the whole debate. You can see the whole debate if you click through to view the history, but like Wikipedia, there is one thing you can read--it's not authoritative, and it's not final, but it's still just one thing. When you Google "what's the meaning of such and such line?", sometimes you find debates in a forum or a long discussion, and that's often harder to consume. So we rely on the moderators and editors to streamline that sort of thing.

You are obviously starting to step out of just the rap game and branch off into several other directions. What originally inspired that, and was there any fear that your core users might get isolated through that transition?

Occasionally we will see some tweets like, "what is the Mayflower Compact doing on Rap Genius?" There are sports rosters on RapGenius (Author's note: seeing the box score of Dwight Gooden's 1996 no-hitter made me sad. A 10-year old Tom was scheduled to attend this game before he came down with the flu). What you see much more than users feeling weird about it is that people think it's cool. You see a lot of stuff like, "Woah, Cool, I didn't know all of William Carlos Williams's poetry was on Rap Genius!" Most people seem to have the "interested" reaction rather than the "let's just stick to rap, guys" response. A lot of the main contributors to the non-rap stuff came over from the rap community, and there are people now just totally dedicated to their own niche interests. A lot of the contributors that started annotating the Bible were first annotating Tupac. It's the same community, it's the same sort of flavor, it's people who like rap but it's really all the people who like close reading with friends with like-minded interests.

And it's not just individuals. It's classrooms too. For kids in a classroom, if the teacher introduces a new assignment, and the project is we are all going to get Rap Genius accounts and annotate The Great Gatsby, that's exciting for them. The kids in the class know what Rap Genius is, it's a site they use for fun, and it has all this cool music they like on it. So it's kind of cool that in school it's not just like, "ok the teacher is bringing us this generic annotation platform." It's like your teacher is saying, "let's bring in this piece of relevant culture to you as an educational platform." We could reproduce Rap Genius and call it something like "SchoolAnnotationPlatform.com," and kids using the exact same platform are going to be much less into it because it's not this toy that they want to use.

What do you know about your individual users? Can you tell when a classroom of students has registered?

There is undoubtedly a lot of activity that we don't know where it's coming from. There are definitely classes that are using Rap Genius to annotate interesting stuff that we don't know about. We do find out about it after the fact. Sometimes we will hear that "X" University has annotated all this poetry under one particular teacher. It's not like they reach out to us, they're just sort of doing their thing.

Generally we have some ways of tracking this stuff though. There is some classification within Rap Genius, whether something is rap or poetry or another type of text. We track that, and we have started doing some reporting for ourselves to see, "oh look, here is all the poetry that went out this week." It's a big priority for us to try to find out as much as we can about users.

Jeremy is the "Education Tsar" of Rap Genius, and how we discovered Jeremy was we were at the airport, hanging out waiting for a flight, just checking our phones, and we got an email (a Google alert) with a link to Rap Genius from some site. We clicked through the site and it turned out to be a syllabus that Jeremy had created. Jeremy, who we had never met, but was a very active Rap Genius contributor. He had 20,000 RapIQ, and by comparison I have 50,000 RapIQ and I've been at this since the beginning. Jeremy had this syllabus that was like, "why we use Rap Genius in an English classroom, what we are going to do with it, here are some screenshots, here's an example of an annotation" and so on. This was amazing to us, so we reached out to him and were like, "how did you figure this out? What were you thinking?" He was just very creative, very passionate about Rap Genius as a user, and he was also a high school English teacher with a PhD from the University of Texas. He was just an amazing guy. We got to know him a little bit better, and now his whole life (instead of going and becoming a professor) is spreading the Rap Genius gospel and bringing it into other classrooms. He was in California last week working with a bunch of teachers, getting their feedback, trying to train them on how to use the product and share his experiences using it in the classroom. There have been dozens of other classes now, high school and college, that have used it to annotate everything from poetry to novels to scientific papers. There is actually a biology classroom that used Rap Genius to annotate a very technical paper on hermpaphroditic fish, and they had to take each fish species and annotate it with some type of information about that type of fish, or they would take scientific terms that weren't obvious, label them, and expand upon those.

And some classes use it to annotate rap. Big sections of rap history are still not close to being done on Rap Genius. There are so many people in the community now that any new album that comes out, it's going to get annotated really quickly and densely (a lot of people are going to contribute to them), but if you look at stuff from the '80s, the early '90s, there are huge parts of rap's history that still need work. I think a lot of people in classrooms, especially classrooms focusing on hip hop, musicology, and history, like to go in and fill out the catalogue, and have discussions around that sort of stuff.

Now that you are formalizing this education-facing piece of Rap Genius, does that present a new business model?

Right now, we are focused on getting it into the classroom for free, which is hard enough. It's a very compelling product, but there are obviously some teachers that are like, "I don't know... there are some swear words on the page, how can I use this in my classroom?" Some teachers will not use a product like this. It's a challenge just to get people to use something for free. We'd like people to use it on a large scale. We think the idea of creating incredible digital editions of various texts is really exciting. Columbia University is going to be annotating core curriculum texts. They will have their whole freshman class annotating The Odyssey, The Illiad, stuff like that. When the collective mind of the Columbia students and their teachers giving feedback gets to this thing, I think you are going to have the best digital editions of those books in the world. We want to change the way people read a book by contributing and participating and annotating, but we also just want to create the best edition to read so in three years when you want to order The Oddyssey on your iPad or whatever device (Author's Note: :-) ) for your college class, you're actually ordering the Rap Genius version. You are taking in all those annotations, interacting with those annotations or creating new ones, and this sort of changes the format of the book. You could go out and charge schools for a product that they can then use as a teaching tool, or you can try to get schools and students to participate in this movement to create really interesting texts. We are more interested in getting people on the platform, using the tools and creating sort of like a MOOC (Massive Open Online Class, to the plebeian) which I am just now learning about. I hadn't discovered that word until a few weeks ago (Author's Note: tisk, tisk). That's something that aligns pretty well with our thinking about how this works, but it could be a business. The education portion of Rap Genius could end up being something that we sell into schools and develop a course management concept. It's a little far up field from what we are now doing. We are a small team trying to build a huge thing for regular people.

There are a lot of possible business models out there and education is one of them. Another one is the enterprise sale of Rap Genius software to solve some communication problems. If you think about the CIA, right now, having a team of people in another part of the world reading a memo, commenting on that memo, and having those comments go back to the original writer in some sort of fashion, Rap Genius is actually a great product for something like that. Selling separate versions that people can host on their own servers--that's a potentially lucrative business that we are fielding a lot of interest about. But for now, we are focused on building an iPhone App, building more features for our core contributors, stuff that makes it fun to use Rap Genius.

When I was in high school, a lot of kids used (and likely abused) SparkNotes to the point where they maybe... kind of... didn't read the whole book, and just read the chapter summaries (Author's Note to his English teachers: Not me! I read every word...). So I always felt like there was this stigma around using SparkNotes, even if you were just using it to get some ideas for class discussion the next day. Is this stigma anything that you would see as a fear when directly entering the education arena with this product?

Well, we always have the texts. That's what's different between us and SparkNotes: it's not a summary. I think SparkNotes is great.

One way to take the temperature of whatever you're doing is to do a Twitter search and see what people are saying. A lot of times, and especially in the last six months, we get tweets like, "Can't believe I just used @RapGenius to help study for my #finalexam in English (or whatever class)." And I think people are, and definitely for poetry. If you go to "The Wasteland" on Rap Genius, that's an amazing resource. It's really well annotated by a bunch of different people, and if you're reading "The Wasteland" in your English class, you can definitely get a lot out of it. I'm not saying people should go and copy the analysis for their essay, or that they won't get caught if they do that (it's definitely Google-able).

It's amazing that people are using it for school. I think SparkNotes has Harvard students write these articles, and they're high quality. But what's cool is if you're a kid studying for your English test, and you're using Rap Genius to cheat, there's a temptation to get in there and actually interact. So a lot of those kids that go on their to study or to steal some sort of interpretation to write about actually end up writing their own stuff on Rap Genius. It's just amazing how many kids we have seen over the past few years that started out at 16 as horrible writers, and we nearly kicked them off the site because they were such bad writers, but instead they stuck around, their writing improved, and now they are getting into good colleges. If you actually get involved as a contributor, it's much more valuable than if you are just reading and picking up on the annotations. The annotations are interesting if you can find what you are looking for, but if you actually start to write it's like exercising your brain... Everyone wants their kids in the classroom to do close reading, and that's what Rap Genius is. It forces you to use annotation to think pretty hard.

Venture Capitalists often have a hesitance toward investing in content businesses because, as Rap Genius is demonstrating, the internet and shifts in social tendencies are increasingly driving the price of content toward free. To what extent do you think there still needs to be an arbiter of what great content looks like, and one that is compensated as such? Or can the crowd truly source the best information?

I am always a middle path kind of guy. I don't think, "It's all the crowd, there's no reason to have any editors." I think if someone has outstanding abilities, writing talent, curating talent--those people can add a ton of value. The relationship between a person like that and the crowd is often very complicated. They are often just a very strong member of that crowd. Sometimes that person is in a totally different place from the crowd, is actually doing something quite different, or has a different level of privilege. But if our front page or any part of the user experience of Rap Genius feels a little too crowd-generated and content suffers, that means we may have to dial a knob somehow, whether that's changing the incentives that the crowd has, or having more resources trying harder to find the best people from within the crowd and give them special privileges. We are just looking for the best outcomes.

In any situation that we have seen so far where it looks like the crowd is a dominant player, there are all sorts of things going on at the margins that you don't know about. There have been articles talking about stuff like, "what's really going on at Wikipedia? Who are the main editors, and how do they promote content to the front page? How do edits take place, and how are they reviewed?" There's always this crazy power struggle, and there are people at the top, certain elements of hierarchy and elements of flat, crowd-based decision making. I think it's sort of like a wild west right now, I really don't know.

There are some people that say, "Rap Genius needs to hire professional writers because you can't trust the crowd to come up with interpretation." Well, I wouldn't trust three or four hired writers to do an excellent job annotating the entire corpus of music and poetry and novels and everything else. I think the crowd is incredibly powerful, it can't be denied. It's where history is going, and you just have to tweak the knobs correctly.

How did you get contacts with artists? How do you plan to make this more of a component going forward?

Nas was the first rapper to annotate his own lyrics on Rap Genius (Author's Note: I guess you could say he is trying to keep hip hop alive?). We were introduced to Nas by one of our early investors, Troy Carter, who is Lady Gaga's manager. Troy is a great guy, has always been such a huge friend to Rap Genius ever since we met him. He was always saying, "we've got to get artists involved in this site, we've got to do something special. You guys should at least meet with Nas, talk to Nas." So we decided, let's do an interview with Nas and let's ask him questions about his lyrics, because we're a lyrics site. We'll do an interview, do a video, and ask him questions about his lyrics: tell us the meaning of this, the back story behind that. We did this interview and it was great, and we decided to cut out those answers and put them on the page itself. So you can click on a line like "sleep is the cousin of death," and instead of some random collection of what kinds around the world said, you have Nas explaining what he was thinking. That was really cool, and we thought, "wow, this should show up differently than our annotations, which should be a different color or something like that, something to verify it like Twitter has 'verified accounts'."

So we built that, and then we built a sort of self-serve product for other artists to use. Any amateur artist could get verified and start explaining his own lyrics. So we started making a real effort. We got to other artists and record labels and managements and would say, "hey, look what Nas is doing! This is pretty cool. You've got all these fans searching for your lyrics, more and more are coming to Rap Genius instead of these other lyrics sites: do something with them! Meet them halfway, or give them something to consume so when you release a new song and millions are your fans are checking out the lyrics on Rap Genius, it's a really great experience for them to be clicking on the green line and seeing what you have to say." We have had a ton of success making that case to artists. They also like the part of it that's like, this is going to be around in 50 years, 100 years, and people are going to be consuming your song (whether it's on rapgenius.com or on some Google Glass Rap Genius App), it's going to be that information, that content. So a lot of artists think about it as leaving a little mark. I can tell this story, I can tell it one time, and it's just there forever when people click to consume my song.

So part of it is marketing and the same reason they use Twitter (get in touch with your fans, Fun + Marketing). But also, unlike Twitter and Instagram, you are making a lasting comment. You do a little bit of effort, and now the song is always carried on by your stories.

The main resistance we get from rappers is, "I don't want to eliminate the mystery for the listeners. Part of the beauty is them trying to understand my raps." Our response to that is, "well you don't have to explain that line, and you don't even have to explain any line, you just have to tell stories." So a lot of times it's like, "oh this is where I was when I came up with this verse, this is how I thought of it," or "here is a funny story, it's actually based on a friend of mine." Sometimes it's stuff that's not cryptic like a puzzle, it's more stuff you could only know as the lyricist. Artists have been really receptive. They really like it. The tricky thing is, many artists are not using computers on a day-to-day basis as much as they are using their phones or even iPads, and we don't (yet) have a mobile app for them to just quickly do some stuff. They have to sit down at their computer, they have to remember their password, so just getting them to use another service, especially someone as busy as an artist, is a trick.

So when do you get President Obama annotating his own speeches? How does that happen?

That has got to happen. We've got a couple of angles, we have actually tried to get Obama verified on Rap Genius. He went on Reddit and did the Ask Me Anything type of thing. It's gonna happen. All of his speeches, literally every speech Obama gives, gets uploaded on Rap Genius and gets annotated by a bunch of people. There's a lot of activity there. A friend of Mahbod (cofounder of Rap Genius) was a White House staffer in the early days of Rap Genius and said that they were looking at "99 Problems" on Rap Genius, Obama and a couple of his staff members. So he's aware of it, he's clearly into it, and it's just a question of his schedule... Maybe after he is out of office he will have a little more time and he can do some annotations.

Which teacher was most influential in your development, and why?

Wow. Umm... I guess I would say that this guy from college: Ludger Viefhues. I took a random class my sophomore year on religious theory and method in the study of religion with him, and it was so interesting, I decided to major in Religious Studies. It was also something that finally helped me understand what the point of theory was, and taught me a lot about close reading. He was really into all those things, and I think all those things kind of informed a lot of my life as a student and also at Rap Genius. He's just a great teacher, I loved him.

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