Courtesy of Caleb Madison

Caleb Madison ’15 is a young gun in the world of crossword constructors and solvers. Madison, once an assistant of the New York Times puzzle editor Will Shortz, has run dozens of puzzles for the Times. Now, Madison has moved on to greener fields: He’s been Buzzfeed’s puzzles editor for less than a year, but has already published crosswords with titles like “How Many Kardashian Sisters Can You Find In This Mini Crossword?” and “Swiper Start Swiping: Finally, a crossword as superficial as #millennial dating culture.” WKND spoke with Madison on what makes a good puzzle for millennials, Twitter harassment and Guy Fieri.

Q: I just finished the “Lil Crossword You Should Try” that was posted at 7:30 this morning.

A: Did you have fun?

Q: It was great. What was your favorite clue from it?

A: I wrote it down a little bit ago, but I think the “yoga” one I was happy with.

Q: [1-Across] Activity that’s for total posers? Yeah. How far can you push the envelope of being raunchy or inappropriate in your puzzles? (e.g., 9-Across, “Where your poop comes out.” Answer: ANUS. 7-Down, “Unwanted release portraying some much-wanted releases.” Answer: SEXTAPE.)

A: I have no standards of decency in my life. I try to carry it over to puzzles as much as possible, both because I think it’s funny to see, but also because I think if you look at an answer like that in the crossword, some of your preconceptions about what a crossword contains might be upended in a fun and surprising way as well. I like using vulgarity and stuff like that to let people know this is a different type of crossword, or at least trying to be.

Q: Is there anyone overseeing you at work drawing a line at any point?

A: Nope. No no no. [Laughs] They’re just interested in me making a successful puzzle, so however I think that is best done, they go with completely.

Q: I’ve tried doing the puzzles before — they’re hard! Where do you find that balance of being relevant to your audience but also being challenging?

A: I would ideally like to make them less challenging. A lot of people do them, but a huge barrier is not even whether or not you know the answer to a clue, but whether or not you can get past the language of the clue to understand what it’s asking for. I think what [trips] a lot of people up, especially people who’ve never solved crosswords before, is translating that weird clue language, which I’m trying to make more casual. I’m realizing it’s still a little hard for people.

Q: You talk about people who’ve never solved crosswords before solving yours — who is your audience?

A: I don’t know. I am slowly learning that, and it’s certainly been a learning process. We started off this year with New York Times-style, daily 15×15 puzzles. The puzzles the Times does are big, and they have themes (three or more answers are tied together in a certain way). That was my only model for doing something like this. I commissioned a bunch of those, and people were just like, “This is too big. I don’t have enough time to do this. And also, I don’t really understand what’s going on with the clues. And also, I don’t really like a theme. I don’t like having to figure something out on top of having to figure out the clues.” Which I totally understand.

That’s why I’ve been making these smaller ones that don’t really have a theme, and also trying to make the clue language a little more casual. My audience, I would say, is some subsection of Buzzfeed’s audience, and I think a huge part of it is liberal arts college kind of people, a demographic that’s both young and on the Internet and would be into doing a crossword every day.

Q: You’ve talked about some of the differences between the crosswords Buzzfeed and the New York Times publishes, but are some other differences between editing crosswords at Buzzfeed and doing the same at somewhere more established?

A: The Times has a formula they have perfected over the course of 80 years, where they have a huge built-in audience of people who solve a puzzle either online, but mostly on paper, and they have this huge reputation. They’re interested in maintenance and slow progress — adapting the formula for the Internet age but also retaining their massive fan base of dedicated solvers.

My job is to make a puzzle that doesn’t have that. I have no restrictions on what I can do. My only objective is to get people on Buzzfeed to solve this crossword. It’s very general, but it’s also a little more exciting to me because I get to figure out how the crossword translates to the digital age without any sort of standards to uphold. I have no audience who’s going to get really mad if I start making smaller puzzles or making different types of puzzles or changing how I clue things. I’m trying to erase all those traditional standards from my mind, and I try to just make a product that is still a crossword puzzle but has been adapted to make it more intuitively understandable and exciting for the younger, online, millennial, hashtag-y, Buzzfeed audience.

Q: What has the response been like in the last few months since you’ve launched?

A: This whole [project] is a process and an experiment, and I’m excited to be tinkering with this stuff. Buzzfeed’s a very experimental place in a bizarre way, in that as they’re tinkering around to crack that viral code, they’re willing to try any and everything.

And so, I’m going to keep doing crosswords until I find one that really sticks. I also tend to think that the measure of success for crosswords on Buzzfeed is going to be different from other posts because it requires more investment, more interaction. There’s some weird Frankenstein-y combination of a quiz and a list — it’s like a bunch of quizzes smacked together in the form of a list. Now we’re doing this thing where we’re trying to have people sign up for a newsletter [that emails a crossword] to your inbox every morning, which I think is more up the alley of how people experience crosswords, wherein it’s more ritualistic than scrolling through Buzzfeed and finding things to click on. It’s more about a repeated experience that you know is going to happen every day.

Q: Is there any one particular puzzle or clue you’ve been proud of lately?

A: Yesterday I did a puzzle — it didn’t do very well on Buzzfeed, but I was very excited about it. It was from the perspective of Kanye West, so all the clues were in his voice, and some of the answers were related to him. I thought it was really fun and I thought people would like it more.

Q: Were you inspired by his new album?

A: And his tweets. He’s a celebrity who has a really distinct voice that people respond to and is easy to parody in text, not even speech, because his Twitter is so iconic.

Q: Where else are you getting inspiration from lately?

A: Buzzfeed has made their success on seeing what works and transferring that into other forms. So, [I’m] trolling the Buzzfeed page, looking for how a puzzle can be framed, but also I love weird pop culture words and slang. I’m trying to think of what was in the one today — GUY FIERI, SEXTAPE — I just like frank things that you would balk at and be like, “How is that in the crossword?” I think that’s a funny reaction. I like that crosswords have a reputation for being old and crusty and it gives me a lot of room to be like, “No, fuck you.”

Q: What’s the weirdest or worst reaction to the Buzzfeed crossword you’ve received? Or most memorable.

A: They’re really not very creative. They’re usually, like, “I hate this.” Or, they’ll [reference] a clue and say, “Seriously, Buzzfeed?” And a classic one they do for every Buzzfeed post, because a lot of the Buzzfeed posts seem casual and easy to do: “Someone’s getting paid for this at Buzzfeed? Wow.” And I’m like, “Yeah, someone is. It’s me. Just relax.”

Q: Where do you see Buzzfeed Puzzles in a year? Or yourself in a year?

A: In a year, I see Buzzfeed Puzzles on every neon sign in Times Square. No one can really look up, everyone’s super invested in doing these puzzles, people are bumping into each other, I not only have one app but I have seven apps — one for every type of puzzle I can do. And myself? Kind of just King of Manhattan, I guess, in that world. I’m a humble man. But honestly, I have no fucking idea. One thing about post-grad is that you have to take it a day at a time, which I’m kind of enjoying.

Q: Do you feel like you’ve gotten a bigger Twitter following?

A: If a puzzle’s a little late one morning, people tend to harass me on Twitter.