On Tuesday, we descended into the seedy depths of Williamsburg, Brooklyn to interview the pair of Yale College graduates who, in 2009, founded the company formerly known as Rap Genius. (It was recently rebranded as simply Genius.) Their office space is a simple suite of apartments in a condominium building overlooking the East River.

We caught them in the midst of a big transitional moment: This spring they’ll move into a new 44,000-square foot headquarters, putting to use the $40 million investment they received in July. They’ve also announced a new technology that will go on the website, allowing users to wield their annotation toolkit anywhere on the Internet. It’s all part of their goal: to make Genius an essential part of the Internet’s fabric. Tom and Ilan greeted us in slippers, offered us Pellegrino, and invited us to take a seat on their couch.

Ilan, the president, majored in religious studies at Yale, and worked at Google and HBO before devoting himself to Rap Genius. He’s also a certified hypnotherapist. Tom, who double-majored in Ethics, Politics and Economics and mathematics and philosophy, is currently CEO.

We’re Yale freshmen, and since being at Yale — since being in our position, you have gone on to —

Tom Lehman: Well I wasn’t quite in your position. I was in Pierson, which is a worse version of Davenport, and so even though I had that disadvantage —

You still made it?

TL: Well, I don’t know if I made it. But things are going okay.

What college were you in, Ilan?

Ilan Zechory: I was in Trumbull. Trumbull was the most run-down, it was like the art stoner vibe. I don’t know if it’s still that way.

What are your thoughts on the fact that you can kind of tell what college someone’s in? Why is that?

TL: If you’re in Grand Strategy, you’re maybe in Davenport. Does that answer your question? No offense. I had friends who were in Grand Strategy. Whatever.

IZ: In Trumbull, there was maybe one token strapping Christian kid. But it seemed like other colleges had a ton of them, and we just had a bunch of, you know, like pseudo-intellectuals, basically.

TL: It was the cool kids. Pierson didn’t have a lot of cool kids. Sorry, Pierson in heaven. Noah and Dave were good.

Shoutout to Noah and Dave.

TL: And others. I’m kidding! This is insane for me to say this.

You’ve gone on to start a multi-million dollar company, you know rap stars, you’ve traveled the world. Have any of the those experiences topped your Yale experiences in terms of craziness level? What are the most memorable Yale times?

TL: There’s a meme called the Yale Bubble, or whatever — you know, it’s not a literal bubble. But what it means is that you’re sort of insulated from the world. And I think that is very true in the sense that I thought, “Whoa, big time, I’m in college, I’m doing real work.” Yale was way more tame and chill. It’s nice, because if you’re a potted plant, and you want to transplant it, you’ve got to have it be nurtured in its original home.

IZ: And you’ve got at least four years or whatever to have that protection from society, and despite having homework or whatever it’s not that crazy or that hard, ultimately. Ultimately. You do hard work for sure.

TL: Anything that you’re doing that seems hard, but — oh wait, it costs a ton of money to do — that’s not hard. You’re paying a ton of money for it. When you’re trying to get paid …

IZ: … things can get hard.

TL: Yale is definitely a time when you can chill out compared to what life feels like now.

When you were at Yale, did you have any sense of where you wanted to go after that?

TL: I thought guaranteed: going to go to law school, hopefully a prestigious law school,  because I was into that kind of stuff back then. There was actually a major at Yale during my time where you had to apply to get into it. So I was like, “That’s the major for me!” I was an idiot. Anyway, I thought I was definitely going to go to law school, be a legal academic. I was very taken with constitutional law, particularly John Hart Ely, very taken also with law and economics. Word to Susan Rose Ackerman, word to Henry Smith. I thought that was going to be my thing. I thought “Okay, I’ll take a year in New York, I got this interesting weird opportunity at his hedge fund, it seems kinda weird and chic, but you also don’t have to dress up or whatever, and do something-something with computers, and a bunch of people are moving to New York. That seems like the thing — I’ll do that.” And then everything got all twisted and turned, so, yeah, I did [work at the hedge fund], but it was all wrong.

IZ: I came in freshman year, I was takin’ a bunch of different stuff. I didn’t know what I was gonna major in, I didn’t know what I was going to do with my life or whatever — I wasn’t too worried about it. But then around sophomore, junior year — that was 2004, 2005, so that was the birth of blogs, basically. So, I got a blog, and I had a lot of fun with it. And … perfect! Then I started taking writing workshops, and fiction writing and screenwriting, and writing on the side myself and thinking: okay, great, I’ve found my calling — I’m going to be a young, white, Jewish writer, in the mold of Woody Allen or Philip Roth! I set my sights on that kind of thing, and then I realized, or as time went on the world told me, and I told myself: that’s not interesting anymore. So, I still like writing. I still think writing is interesting. But that mold is over, I think — the white Jew. No one wants to hear what a white guy has to say anymore, which is good. I think that’s good.

TL: Also, college is a very individualistic thing. It’s like, okay, what are you going to major in, what’s your GPA … and so that encourages you in college to think about yourself as: I’m special, and I’m a rugged individualist. I’m going to be a professor! I’m going to be a writer! The reality is, in life, hard things — very difficult to do alone, and most important things or desirable things to do are very hard. And so, big difference between college and the real world is that — sorry to use that phrase — there are groups of people involved. There are group projects, and relationships, and so forth, and —

IZ: I think a lot of people learn about that through extracurriculars. But not me and Tom!

You’ve always had this – in interviews, and also as a company – this irreverent, playful tone, to some extent. I can see that its part of your personalities, but going into a corporate world, how much of that have you had to rein in? Or have you just completely said, “That’s the character of the company and we’re gonna keep it”? What’s the push and pull of that?

TL: The real answer is threefold. Part of it is that we are constantly trying stuff. I’ve got this whole philosophy: worse is better. Basically it’s this notion that you’ve gotta get out there in the world and try to do stuff. You have to try things. There’s this great book called “Art and Fear,” which I’ve never read — I’m ordering from Amazon now, but I read an excerpt from it — okay, this is how honest I am — and the excerpt talked about how an artist is setting up a ceramics class and runs an experiment. (Actually, I’m very into ceramics and wheel-turned pottery so this is particularly salient for me.) But the basic idea: A teacher tried this experiment. He said, “Okay, two groups. The quantity group  I’m going to take all the pieces you make, put them on a scale, and if it’s past a certain weight, you get the A.  The quality group – you just have to make one great piece.” What they found was that the quantity group actually ended up with the best quality, because the quality group was just stressed out, and the quantity group was trying and refining and trying and trying and produced a lot of crap but ultimately ended up producing something good.

So whether it’s the literal annotations on your website or the way your website works, or the way you interact with the world, you’ve gotta be trying new things. You can’t be afraid. You can’t be thinking: “Ah, how do I project to the world in a way that’s absolutely perfect, in a way that is kinda lighthearted but also underscores my seriousness?” We’re complicated people in the sense that we like jokes, but we’re also very serious about the work. And I think we’ve projected something that perfectly encapsulates who we are.

You’ve said that Genius is a 10-year project. What is the bulk of that? Because it seems like you have the basic technology in place. I guess you just came out with the embedding technology, last July. What are you trying to put in place over that timespan?

IZ: Last year we did the ability to embed. This year we’re doing the ability to literally annotate any website on the internet without embedding anything. Just going to any website and annotating using our special sauce — like, that’s an incredibly hard technical problem. So what are we doing for the next five years, or maybe the next 10, 15 years? Just building more and more technology, and building more and more of a movement.

TL: I agree with that. The scary thing is: You have to have new ideas. In other words, like, it’s so hard to have a good idea, and by good idea I mean something that anyone actually cares about, let alone a lot of people. It’s so hard to have good ideas that, whenever you have one, what you wanna do is just keep pouring gas on that fire, keep extending it. And you have to do that — keep pushing. But you have to have brand-new ideas. And ideally the ideas have a common theme, and they connect and whatever, but you have to have new ideas, and that is an extremely scary prospect, because, I put all the good thoughts I had in my first book! There’s an old saying. I got it from the Rawls character from “The Wire.” He says everybody has one book in them, almost no one has two. And I think there is a lot of truth to that. So you have to have new ideas, and the way to have new ideas is not to sit in a room and start thinking about it. We have this saying here at Genius: “Hi, modernism!” Good. High modernism, bad.

Some would say that Yeezy season is approaching right now. That’s the feeling right now. This is kind of a two-part question. One: How involved are you in the Yeezy circle? Have you been in contact with him? Is he on board with Genius?

IZ: Yeah, we have met and hung out with Kanye. He is just a truly great guy. Like, he’s a truly, truly great guy in the sense that a) just a nice guy, and b) super interesting. Like, a super fascinating person to be around. He says great, interesting stuff, also has a way of being in the world, that is, you know, related to what makes him a good artist. He’s just a deep and fucking interesting guy to be around. I have a ton of love for Kanye, not only as an artist, but in the times we’ve hung out, briefly or whatever, like — just really really cool guy, and he’s down with Rap Genius. He’s sent us an idea for how the site should look. He’s engaged. He’s got this new music coming out.

Have you heard it? Are we ready?

IZ: I have heard, I’ve heard all the songs. I heard “All day,” I heard “FourFiveSeconds,” I heard “Only One,” all a long-ass time ago. They were all different when they came out. Heard a real work in progress. I think I heard “FourFiveSeconds,” and Rihanna wasn’t on it yet. But it was a long-ass time ago, but he was just playing stuff, and it was amazing. He was so excited to share it. He played these 12 songs he had ready, like, five times in a row, and everyone was loving it. I think the album will be coming out, it seems like, very soon.

TL: The thing about Kanye is — if you think about the iPhone — what is special, truly special about the iPhone? What’s special about the iPhone is that the iPhone is the product that makes it so that the richest billionaire in the world and you know, a normal college or high school kid who’s got a little money, can still use the same phone. Like its not obvious this is the way it would work out. There was the ver2 phone, right, this $5,000 phone. Kanye is the embodiment of that notion — the richest billionaire in the world, Ben Horowitz, is still listening to “The College Dropout,” just like a college kid.

Part of his whole ethos when he’s talking about his new clothes or shoes — he doesn’t want it to be a limited edition, special sellout, $400 thing. He wants it be for the masses, the iPhone. That is very deeply woven into the Genius philosophy, that if you wanna understand something, you don’t have to be the billionaire of knowledge, the insider who went to Yale or whatever, who knows the guy who knows the guys who know the backstory. Everyone can know that. You don’t have to feel bad that you’re pretending to know who your friends are talking about. You just go on the thing and look it up. Likewise, when you’re annotating, you could be a billionaire who owns a newspaper and gets to control the words on the newspaper, but then anyone can go right in those words and annotate right on top of them and have the same stature as that billionaire. And so that philosophy — that Apple embodied, Kanye embodies — is also what we try to take some cues from. So Kanye is a major inspiration for us.

Note: This interview has been updated from the version that appeared in print on Friday, March 6.