Puzzle-Maker Wyna Liu's Just a Little Mean

Summary

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Podcast Summary: Humans — "Puzzle-Maker Wyna Liu's Just a Little Mean"

Host: Hank Green
Guest: Wyna Liu (writer of New York Times Connections)
Date: June 11, 2026

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Episode Overview

This episode of Humans features a deeply engaging conversation between host Hank Green and Wyna Liu, the founding writer and editor of the viral New York Times game, Connections. They discuss the psychology behind puzzles, the art and craft of creating a hit digital game, ritual and low-stakes meaning, and the “just mean enough” philosophy that makes Connections a compelling daily challenge for millions. The episode intertwines Wyna’s personal story—including her creative process, career path, and family background—with broader ideas about human cognition, culture, and the meaning to be found in everyday rituals.

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Key Discussion Points & Insights

1. Why We Love Puzzles

• Certainty & Satisfaction: Wyna explains that puzzles offer what life rarely does—a clear answer and the pleasure of “getting it right.”

  "Growing up, you just want to do the right thing. And sometimes you're like, oh, maybe there is no right answer... But with puzzles, there is." (01:45 — Wyna)

• Feeling of Dialogue: Hank feels a personal connection playing Connections, almost in mental ‘dialogue’ with the creator.

  "I feel in dialogue with the puzzle creator. Does this seem right to you?" (03:37 — Hank)

2. Inside the Design of Connections

• Game Mechanics: Connections gives players 16 words to sort into four categories, often with the categories arranged by difficulty from easiest (yellow/green) to trickiest (purple).

  "Connections is a category matching game where you're given 16 cards and you have to sort them into four groups of four by identifying the thing that they have in common." (02:07 — Wyna)

• Personality in Design: There’s a unique “voice” in Connections—opportunities for humor, cultural references, and surprise.

  "It's true that Connections, I think, is a little like voice-ier than some games." (09:18 — Wyna)

• Empathy & Prediction: Wyna tries to anticipate what millions will notice or miss, commenting on the empathy and cultural awareness needed for wide-appeal puzzles.

3. The Human Element & Cultural Context

• Cultural Overlap (and Limitations): The game relies on shared knowledge that is specific to its (mostly American) audience. When British players try it, for example, they find unexpected cultural disconnects.

  "You don't have to design something that's gonna work for someone in Vietnam, but it seems like it's very human work." (04:32 — Hank)

• Puzzles as Community and Ritual: Solving Connections connects players not only to the game designer but also creates a sense of being part of a vast community.

4. The Puzzle Maker as Celebrity

• Microfame: Unlike most puzzle creators, Wyna has become a minor celebrity; her personality is felt in the game and players are often keenly aware of “her” as the architect of their daily experience.

  "People seem to care about you... You're like a little bit of a micro celebrity and you are saying yes when people ask you to go on podcasts." (08:51 — Hank)

5. Building Puzzles: The Craft and the Challenge

• Origin Story: Connections was born during a New York Times “game jam” after the acquisition of Wordle (10:03–10:44).
• Testing, Feedback, and Difficulty: There is an editorial/tester process for vetting puzzles; category difficulty and color assignment are more art than science.

  "There is a question on the tester feedback form that is like, did the colors match your solving experience? And if there's a consensus for a change, I'll happily make the change." (54:30 — Wyna)

6. Game Evolution, Voice, and Sharing the Craft

• Wyna's Hope for Guest Boards: Wyna is open to personality and variety—she'd love to see others create boards, but acknowledges the challenge of maintaining quality and coherence.

  "Because there is so much room for personality, it'd be cool to see, like, I'd love to see your boards." (15:20 — Wyna)

• No Submissions (for Now): NYT Connections doesn't currently accept outside submissions due to the overhead involved in editing and testing.

7. Personality, Being “Just a Little Mean” & Red Herrings

• A Mean Streak—In a Good Way: The most memorable and fun puzzles are sometimes the ones that frustrate solvers just enough—Wyna enjoys being "a little bad" but not outright cruel.

  “I love people, but I also love being bad.” (19:01 — Wyna)

• The “Chiclet” (Rainbow Herring): Wyna and Hank discuss the in-game phenomenon of a clue that looks like it fits every category—a particularly sly puzzle trick.

  “A Chiclet is a red herring that has a color from every category.” (17:26 — Hank)

8. Low-Stakes Rituals and Their Importance

• Why Low-Stakes Still Matter: Both agree on the deep value of low-stakes, “unimportant” daily rituals as sources of satisfaction and structure in life.

  “I think it's good to just have a thing that doesn't mean anything.” (26:34 — Wyna)

• No Effort Is Wasted: Wyna’s philosophy is that time spent on interests—even those with no clear “goal”—is still valuable.

  “No effort is wasted.” (41:13 — Wyna)

9. Personal Background: Family, Art, and Radio

• Creative Roots: Wyna shares how her parents—owners of AM radio stations, her dad a former DJ in Taiwan—inspired her openness to both creative and practical pursuits.

  “My dad was a DJ in Taiwan in the 50s... His dream was to come to the States and to have a radio station. My name is actually an acronym of my parents' initials.” (45:14 — Wyna)

• Making as Learning: For Wyna, artistry is about “making stuff” in order to understand and engage with the world.

10. Advice and Lessons Learned

• Embrace Evolution: Wyna’s parting wisdom:

  “There's an idea that things can evolve... You don't always know when you start doing something what it's gonna be, and that's okay... You will do a lot of stuff. You'll put in a lot of work that doesn't go anywhere, but it's part of the process, and that is okay.” (56:36 — Wyna)

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Notable Quotes & Memorable Moments

• On Connection and Empathy in Puzzle Design:

  "You're not just making puzzles. You're building little experiences inside of millions of other people's minds." (00:08 — Hank)

• On the Value of Play and Low Stakes:

  "Low stakes, but very much not meaningless." (00:56 — Hank)

• On Her Creative Process:

  "Sometimes I'll finish a board and it just makes me smile and I'm like, I think this is a good one." (18:19 — Wyna)

• On Being 'Mean' and Puzzle Philosophy:

  "I love people, but I also love being bad... It's so great." (19:01–19:04 — Wyna)

• On Iteration and Growth:

  "You don't need all the answers first... It's okay to build in some knowledge or expectation that the thing that you start doing will not be the thing it is a year down the line or whatever." (56:36 — Wyna)

• On Why We Do Puzzles:

  "It's like a fun and safe way to use your brain... you can expect at the end you'll get, like, some satisfaction." (52:27 — Wyna)

• On the Safety of a Well-Crafted Puzzle:

  "When I'm playing Connections written by Wyna Liu, I'm like, I know that this puzzle will not betray me... It'll make sense." (53:04 — Hank)

• On No Effort Wasted:

  "No effort is wasted." (41:13 — Wyna)

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Important Timestamps

• 00:08 — Hank’s introduction and framing of Connections’ significance
• 01:45 — Wyna describes why people love puzzles: "With puzzles, there is a right answer."
• 02:07 — What is Connections? Wyna’s elevator pitch for the game
• 09:18 — On the unique personal 'voice' in Connections
• 10:03–10:44 — Origins: How Connections was developed at the Times
• 14:33 — Hank’s theory of knowledge as ‘scaffolding and connections’
• 17:26 — Introduction of “Chiclet”—a multicolored red herring concept
• 19:01–19:16 — Wyna's 'bad' side: the pleasure of being a little mean in puzzles
• 26:34–27:02 — Value of low-stakes activities
• 41:13 — Wyna's philosophy: "No effort is wasted"
• 45:14 — Wyna’s family story: the dream of American radio
• 56:36 — Wyna’s final lesson: embracing evolution and uncertainty

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Tone & Atmosphere

The conversation is lively, candid, and delightfully nerdy—filled with warmth, humor, and mutual respect. Both host and guest are unafraid to geek out about game design minutiae, but always loop back to larger questions about creativity, culture, and being human. Wyna’s humility and Hank’s enthusiasm make for a charming dynamic that will appeal even to listeners who’ve never played Connections.

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Takeaway

This episode celebrates the overlooked richness of so-called “trivial” daily rituals—how games like Connections illuminate how our minds work, bring us together, and offer comfort and meaning in low-stakes play. Wyna Liu’s story shows that creativity is both solitary and communal, planned and serendipitous, and, above all, embedded in the quirky rituals that make us human.

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Transcript

[A]

This is humans.

[B]

Humans, Humans. Humans. Humans, Humans.

[A]

I'm Hank Green. Winna Loo makes one of the most successful pieces of culture on the Internet. Every day, millions of people open up the New York Times game Connections and spend a few minutes trying to figure out how 16 words fit into four categories. And this sounds, I think, small, and in some ways it is like a small thing. But I also think that there are ways in which it is big because to make a game like Connections well, and I know this because I've tried to do it myself, you don't just need to understand words. You need to understand people. You need to understand how we look for patterns, how we get tricked by our own assumptions, but also, like, not just what connects words to words, what connects people to people. And this is what fascinates me about Winna's work. She's not just making puzzles. She's building little experiences inside of millions of other people's minds. She's trying to predict what we're going to notice, what we're going to miss, what some people, but not all people will see, and what kind of challenge will make us just mad enough, but not too mad. I know this because I play Connections a lot. I play it by myself, and I also play it publicly at the end of some of the videos I make. In these videos, you can watch me try to get inside of Wina's head after she has already tried to get in mine, or rather all of ours. So I want to talk to Winna about connections, but also about what designing a game like that teaches us about humans, about ritual, about culture and taste, and about attention and about what it means to make something that is low stakes but very much not meaningless. Welcome to humans. Winna Lou. Why do we like puzzles?

[B]

Hi, Hank. Why do we like puzzles? Sometimes I want there to be answers and there's no answers. And that starts sort of realization just through life. Growing up, you just want to do the right thing. And sometimes you're like, oh, maybe there is no right answer. You just have to just do something. But with puzzles, there is.

[A]

Even when it feels like there isn't, there is. Yeah, Real quick, for the people who don't know, tell me what Connections is.

[B]

Connections is a category matching game where you're given 16 cards and you have to sort them into four groups of four by identifying the thing that they have in common.

[A]

And the groups have colors based on theoretically, the level of difficulty.

[B]

Maybe, maybe. And theoretically, yes.

[A]

So I like to try and get purple first, which is the hardest category. But the nice thing about getting Purple first is that it also makes it so that it is easier to get the other categories correctly because it means that you've done a lot of the work of trying to match things up and make sure that you're not missing anything before you get your first, though, sometimes I identify a category that I think is going to be purple, and I get it first, and it feels very good, even without getting other categories first. And sometimes I think it's gonna be the purple, and I'm wrong, and then I get mad at you.

[B]

I'm sorry. For everyone who doesn't agree with the color assignments, I'm sorry I let you down. I like to think of it as most straightforward to tricky, trickiest. But that's.

[A]

This is.

[B]

We're just saying words you shouldn't.

[A]

Yeah, yeah. You're just gonna make more people more mad.

[B]

Cut that part out.

[A]

But also there's this forgiveness to connection, where if you can get three categories, you get the fourth.

[B]

Yes. I've been thinking a lot about this. With a crossword, you have a blank grid, and you have to put stuff in. And, you know, it's good because there are boxes, so you know that, oh, this has a certain number of letters or whatever, but with connections, it's all there. And you just have to sort it.

[A]

Yeah.

[B]

You have the answer in front of you.

[A]

I find it much more enjoyable than a crossword puzzle, and I find it is very much that. I am playing a game with you in a way where I'm trying to understand what you're up to, and I feel in dialogue with the puzzle creator. Does this seem right to you?

[B]

I think so.

[A]

Do you feel in dialogue with me? Have you watched me play Connections?

[B]

I have. It's delightful. I love it. Sometimes it's like, I'll see you do something that I didn't think of, and sometimes you do something that I did think of, and it's very satisfying.

[A]

Do you find often that there are little half categories that you didn't ever intend?

[B]

Oh, yeah, for sure.

[A]

You just make sure that if there's a full category, you did intend it.

[B]

I think it would be unlikely to be a full category that was unintended just because it's, like, kind of hard to make a category.

[A]

So I want to talk a lot about, like, the actual design of Connections, but I want to talk about other stuff first.

[B]

Great.

[A]

But I think that people get the idea of what Connections is. You were the founding editor of it. I think that you've been the person who made all of the puzzles.

[B]

I'd like to say that I'm the writer.

[A]

Sure. Yeah.

[B]

Just because, like, I've written all the boards that have run the thousand and five or whatever.

[A]

I have written some myself, and they're very fun to do. But having written them, it makes me realize that what you are doing is actually not easy and not even in, like, the. You have to do a lot of them way. But I can see a lot of creativity inside of these things. And I also feel like you are trying to predict what millions of brains will do when presented with this ambiguity. And millions of brains is a weird thing. And of course, the New York Times audience is this particular set of millions of brains. You don't have to design something that's gonna work for someone in Vietn, but it seems like it's very human work and very empathetic work. And, like, you have to understand a lot of different people at the same time. Does this make sense to you?

[B]

Yeah. Making puzzles in this way is really similar to solving puzzles, right?

[A]

Yeah.

[B]

If you solve a lot of puzzles, you kind of know what you expect when you see certain stuff. It feels like a very sort of fluid relationship between, like, what I think would be something versus what a solver might also then think. And I feel the same way when I'm solving.

[A]

Yeah. I also feel this way about writing fiction where you would think that. And it may be this way for other authors, but you would think that when you go in, you have this constructed idea of what's going to happen, and you do a little bit. But also, suddenly, problems are presenting themselves. And what drags me through the actual laborious process of writing is like caring about the characters, wanting to know what's going to happen to them, and wanting to, like, solve their mysteries and solve their puzzles for them in a way that will be satisfying for me. Like, I'll feel good about what happened to these people who I care about, but also will be satisfying to a reader. And, you know, in a way, those are almost the same thing, weirdly, because, you know, I'm imagining my reader in the same way that I'm imagining my characters in that, like, I can only imagine what it's like to be one person, truly, which is myself, and barely even that. So in the same way, I'm projecting my understanding of humanity onto both my readers and my characters.

[B]

I think you said it right. I think that it's the only way to even approach the thing that you said earlier, which is the idea of, like, millions of brains if you think about it like that, it's like, I have no idea what, like, five people are thinking.

[A]

Yeah.

[B]

You know, like, much less, like, what a majority or whatever. So you kind of just try to, like, use yourself. What do I think, as a solver? Like, what are my experiences? And you kind of use those experiences to inform. And, like, sometimes that ends up working out pretty well and it ends up being generalized or whatever. Yeah.

[A]

The fact that your job is possible, the fact that the connections puzzle as a phenomenon is possible, I think, like, reveals something about how much cultural overlap there is between people inside of a particular culture.

[B]

Yeah.

[A]

But also how much. You know, it's interesting how fast it breaks when it goes to England. Like, when British people play Connections, they're like, what the hell is going on? You know? And, like, you think that it's just like, lift an elevator. But it turns out that there's so much shared cultural experience that we don't understand that we have with each other.

[B]

Totally.

[A]

But of course, it is also very true that the New York Times game playing audience is a particular subset of America. But there's also this sense of, like, getting a clue that I am a part of something that I am bound together with not just you, but all the other people who play this game. I will often feel the sensation of, like, I know so many things and not just me, but, like, all of us together. Like, sometimes I'll play a puzzle where I'll, like, run into a clue and I'll be like, this word fits into. Or like, Blondie was this way for me. It wasn't Blondie. It was one of the other comic strips. And I was like, this fits into that box for me. But I couldn't tell you anything about it.

[B]

Yeah, but I know it.

[A]

It was Bloom County. But I was like, I don't know why I've heard of Bloom County. I don't know anything about that. It gives me, like, insight into my own brain in a weird way.

[B]

I just feel like doing puzzles. And I think maybe for me that the first exposure is through crosswords, where there are a bunch of stuff I only know from seeing him in puzzles. And I don't actually know anything about anything. I just kind of have heard of it, but you kind of get to keep it and use it again when it comes up. So it's like, yeah, it's very satisfying.

[A]

Like, you know things only because of puzzles, not because. Oh, my God. Totally. I guess that makes sense. Another thing is happening to you, which seems to happen more to you. Than to the average crossword puzzle designer. People seem to care about you. Is that right? I don't know if they. I'm not saying that I'm not that they're like, oh, I wonder if Win is having back pain today. But they're, like, thinking about you. Yes. You're like a little bit of a micro celebrity and you are saying yes when people ask you to go on podcasts.

[B]

It's true that Connections, I think, is a little like voice ier than some games. There's a lot of room for, like, editorial stuff and little references to things. I understand why that would be the case.

[A]

I think that there's also a piece of it that might be that there is only one of you. You know, there's no other connections puzzle that is, you know, mainstream. So you're like a pioneer in that way. What a wild thing to have happen to you.

[B]

I agree. I got very lucky.

[A]

Are other puzzle people jealous?

[B]

Oh, I don't know.

[A]

I feel like you just blushed. Is that right?

[B]

I mean, I just got assigned to do this sort of feels like right place, right time kind of thing.

[A]

Right. So the origin story of Connections that I have heard is that you have, like a code sprint, but for puzzles.

[B]

Yeah, a game jam. Yeah, a game jam. Yeah. Yeah. So there's like this annual event that they started having in 2021. The Times acquired Wordle.

[A]

Yeah.

[B]

And so I started at the Times in 2020 as a crossword editor. And so, like, all the puzzle editors work on the big crossword together, but we also manage our own projects. And so it was just really crosswords. But there's also the mini and spel. Then after the Times acquired wordle, they started developing games in house. And so they had these game jam events. And so Connections was pitched by a couple of my colleagues and then went through this, like, brand new green light process. And then when they wanted to release it publicly, they just needed an editor to, like, write the 60 boards for that 60 day beta trial. And so they were like, winna, you don't have a game. Do you want to try doing this?

[A]

And you were like, yes, I will be so good at it that it will take over America. I'm going to make you so much money. New York Times. Do you ever think about how much money you make for the New York Times?

[B]

No, no, no.

[A]

I would think about that all the time. You know, it's such an important part of the news business, and it's always a little bit been that, you know, where like crosswords or Classifieds have been an important piece of what actually funds journalism. And it's hard to get people to pay for the thing that is the actual value. But you can feel good about that. We have to find the business models for the things that are important. And we are really in a re establishing moment there to figure out how all those things are gon. Yeah, But I also wanted to ask, like, when you do these game jams, what makes a game good? And I ask this because I get sent a lot of games now, but I get sent a lot of games that, like, are kind of fun one time or are a little bit too complicated or are a little bit too the same as other things I've played. It's really about not the game, but it's about people. It's about, like, how I'm interfacing with the game. Does that resonate?

[B]

Yeah, as much as I love word games, sort of. My favorite game is variety Sudoku. I like, love Sudoku because it's so clean and it's just like logic. It's just kind of a break from interpreting stuff. It feels like relaxing, but with a puzzle that's well constructed, you are asking yourself, what is this person thinking? And then it's very satisfying when you are right about what they were thinking. Right. It sort of feels like a mutual. That does kind of feel like a click, like a communication. I think good puzzles do that. And good puzzles, I think, are also, like, funny. You know, I feel like there's, like, humor in stuff. It's like, kind of silly or sometimes when things are too complicated, it's like, less fun.

[A]

And connections gives you a lot of opportunities to make little jokes. I don't know which one I was playing recently, but it was like, things that have a boss, and one of them was the E Street Band.

[B]

Extremely stupid.

[A]

Yeah, very, very good. But also, like, I don't know, it's so hard to figure out what people will know. So I assume it goes through some kind of editorial process where you toss it off to people and find out that you maybe thought that people knew something that people don't know all the

[B]

time at this point, I'm like, is this just something that I know growing up in the 90s and does anyone know this anymore? Was that like a flash in the pan? And I was just at a formative age and this is just kind of baked in. I check a lot. I mean, there's a ton of stuff I don't know.

[A]

Question. How would you make a connections board for an alien?

[B]

Mm. That's really hard. I mean, I guess my assumption is that it would maybe be like less English language focused. Right? For sure. So maybe it would be. I mean, I don't know, aliens maybe know every language, including, I have no idea, like what's a category. And they're not all language based. Some of them are just like visual. Right. Things that look a certain way. And it's interesting to translate some of those concepts into words. It's like things shaped like a Y, Right. You can say those words. But maybe in an alien connections board there would be pictures. Well, I guess maybe that would be less good because then you'd see it and you'd see all these Y shaped things and be like, that's easy, just the Y shaped things. But like, my gut response, although maybe this wouldn't work at all, is it would be visual, right?

[A]

Yeah, I think it was for like you. There was recently the one that was like the pips on the die. And like, that's cultural. And I was so surprised to find that I click on all of those and I was like, oh, that's exactly what the pips on a die look like. Whereas, like, the two is this way and the three is this way. And I was like, I couldn't have told you that. But apparently I did know that. Also, this happened with pool balls. Like the colors of pool balls.

[B]

I think I used a pool ball in things that are red or something. Or things that are orange, maybe.

[A]

Yeah, yeah, exactly. It was like the three and it was red. And I was like, why do I know that? That's a wild piece of information to not realize. I have in my head the color of the three ball and pool.

[B]

Yeah, all the stuff that like could be in your brain, but all these like other useless things are kind of floating around.

[A]

I actually don't think that way because I don't think that's how it works. I don't think that we like have a mount and then like stuff starts spilling out when we put new stuff in. Oh, I think that it's all about scaffolding and connections. Connections where most stuff doesn't sit on its own. It has some kind of internal structure that it is hanging off of. And when you add to that structure, it just gives you more structure to hang yet more things off of.

[B]

I love that because it really. I mean, the way I normally think about it is sort of like everything that comes in pushes something else out. I feel like it's a very limited bandwidth. I don't think so I'm glad to hear.

[A]

Otherwise, I would have forgotten way more stuff. How would connections change if you gave it away or if somebody else did boards, do you think?

[B]

I don't know, but I feel like, because there is so much room for personality, it'd be cool to see, like, I'd love to see your boards. You know?

[A]

Wait a second. How much would I get paid? No, I'm kidding. Look, if I got an email one day that was like, hank, we are inviting guest editors, I would say yes very fast, and I would also take it very seriously, and I would be very scared.

[B]

I think those are reasonable responses.

[A]

Yeah. I wouldn't want to invite someone who would not be afraid of the opportunity because I think a lot of people don't understand the extent of the work you are doing to make them fun. Do you feel that that is the case? Do you feel like people don't get it?

[B]

I'm not sure I know how much work I put into it. It is, like, very great to hear when someone's like, I can tell you put a lot of work into this. I feel very, very happy to hear that. But there's something. It's like, oh, if people think it's easy, that's also kind of good, maybe, because it maybe implies that you did a. It's like the work you don't see.

[A]

Yeah. If somebody watches a YouTube video and doesn't see the work, then that's the ideal situation. I don't want people to be like, wow, I can really feel like this guy was pulling teeth.

[B]

Yeah.

[A]

So do you have favorite boards?

[B]

I do. There are some boards that stick out in my mind. There was one that was like, it was a long time ago, but all the cards were movies, like, movie titles, but you didn't need to know any movie trivia about them.

[A]

Gotcha.

[B]

So that was like, that's great. That was kind of fun.

[A]

Do you sometimes feel yourself stumbling into situations where you're like, oh, I can actually get a second red herring out of this, and that's gonna make it really fun to have a double red herringboard or something like that.

[B]

It's unusual, at least that it's intentional that that happens, but it has happened. There was one board that was like, white, green, peacock, scarlet. And it also had like, Yeah, I remember this one. Peacock Prime, Paramount. And so it was like, oh, streaming services and include characters. But like, neither of them were those.

[A]

Do you know what a Chiclet is?

[B]

A gum. A piece of gum?

[A]

No, I get to tell you. Connections, information.

[B]

Tell me, Tell Me.

[A]

A Chiclet is a red herring that has a color from every category.

[B]

Oh, I've heard that referred to as a rainbow herring, but I like Chiclet. Why Chiclet?

[A]

Because the Chiclets are like little squares of different color and that's what they look like. When you accidentally choose the Chiclet, it looks like a bunch of Chiclets.

[B]

Excellent look.

[A]

This is one of the earliest episodes of this podcast and if you are not into connections, a lot of this is going to be a little much. But at least you're hearing two people geek out about something they love. So do you have a sense of when you've done one that's really good? How do you, like, know when you're successful? Is it before it comes out?

[B]

I think it's before it comes out. And actually I haven't always confirmed this later because I don't always know when the boards run and I'm not on social media, so I miss a lot of the discord.

[A]

That's probably the healthy way to be. The connections editor is not on social media.

[B]

Yeah. I feel like maybe it's a little self protective, but there are times when I finish a board that I will be like, oh. And usually for me it's because there's some fun words, there's some unexpected words that I just think are kind of jazzy or have fun letters or something or weird. And maybe there's one or two categories that make me smile for some reason that are just different than some synonyms or whatever. It just. Sometimes I'll finish a board and it just makes me smile and I'm like, I think this is a good one.

[A]

Is part of it. When you're like, that's gonna make people a little mad.

[B]

I. Well, I was gonna say my intention is to not make people mad. I love people, but I also love being bad.

[A]

So being bad,

[B]

it's so great.

[A]

This is the most adorable way to be bad. I love being a little bad by making a puzzle game that people will be a little frustrated by.

[B]

It's very tame.

[A]

You're a real rebellious spirit. Winnaloo.

[B]

There are some times I think people will like. I know that people really don't like it when a word is repeated in the category name Interesting on one of the boards. Yeah, I try to avoid that, but, like, sometimes I.

[A]

Sometimes it's very hard.

[B]

Sometimes it's very hard.

[A]

You've got like four synonyms and there isn't a fifth synonym.

[B]

There isn't a fifth synonym. Yeah. And it's very cumbersome to avoid. So sometimes I know people are mad and sometimes I'm like, it's okay.

[A]

That's interesting now that I know that you're fighting for that, because sometimes I feel like the category name is a bit of a strange.

[B]

There's some real, like, gymnastics it takes to avoid the word. And sometimes I'm just like, you know what? I'm just gonna say the word.

[A]

Yeah.

[B]

There's also sometimes categories that are just like. It's like a joke. It's a bad joke. There was one that was like. It was like earth, onion, Photoshop, hen house.

[A]

Things that have layers.

[B]

Yeah. You didn't even flinch. Yeah. And like, the hen house is like, layers.

[A]

It's very good, right? Yeah.

[B]

It's like ones that lay eggs. Yeah.

[A]

Different kind of layer. Yeah. It's so fun.

[B]

Thanks, Hank.

[A]

I think this is just one man's opinion. You could be meaner. Whoa. People get so mad and I'm like, that's why I'm doing this. Are you not aware of what a puzzle is?

[B]

The next time people are mad at me, I'm going to say, this is why.

[A]

If it were easy, it would not be fun.

[B]

You wouldn't be puzzled. People have different relationships with that. Right. There is a sweet spot. And I think it's different for everyone. I think some people just want to be.

[A]

Yeah. Yeah. I mean, I also, like, cannot believe that some people choose a category before finding a second or third category. I'm like, why would you do that? You know what she does? She's going to get you. Are you busy right now? That's the only reason I ever do that is when I'm like, I just got to get through this. I don't have time.

[B]

Or just like the rage. The rage. Solving someone is just like, it will be, you know?

[A]

Yeah. Or if I'm actually racing someone, which I have done and is very fun.

[B]

Oh, how. How do you do? Do you win?

[A]

I do.

[B]

Well, yeah. I bet. Who would challenge you to a connections match, I wonder?

[A]

I mean, I'm sure that I would be like, not in the top 1% of ranked players if this was actually happening as a thing. But maybe you should introduce a time metric.

[B]

I'm just saying I am very anti timer myself personally as a solver, because I get extremely stressed. But I. I don't think that the

[A]

timer should be on the screen.

[B]

I agree. My ideal of Dreamworld is that there is a timer and it's default off, but you can go in the settings and turn it on, and you can see it if you want.

[A]

Yeah, yeah. Look, I'm paying, like, money for this. They should be popping out new features all the time.

[B]

What other features?

[A]

No, you first.

[B]

Mine are not always realistic. I don't play it, you know.

[A]

Oh, yeah, I guess so.

[B]

Like, I feel like there's a big. In terms of, like, usability.

[A]

You play it in your mind a lot, maybe.

[B]

Yeah, yeah. But I wouldn't want to ask people who spend more time with it. But I think that it'd be cool to be able to, like, mark up things. Yeah. Like in the colors.

[A]

Yeah, yeah, yeah. There's actually a plugin that does that.

[B]

Yeah, yeah. I heard there's, like, a site or, like, you know, color.

[A]

Like, little color tags that'd be, like, easy mode almost. So I actually have a personal story for you. So I went through chemotherapy, and that really does a number on you. And one of the things that it messes with is, of course, like, cognitive function, so I couldn't think as well. And this was very unpleasant for me as a guy who prides himself and who is, like, publicly known as being, like, a thinky guy. And so I played Connections all throughout chemo, and it was, like, harder on the harder days, and I was like, I'm dumber sometimes now. This was actually before the ranking was introduced, so you didn't actually know how hard the puzzles were. But coming out of chemo and feeling like I was getting better at Connections was a little gift from the world. Being like, you're getting better in a way that there's no other way to measure. That was part of, like, when I first started to love the game, though, if I hadn't gotten better, I don't know how I would have responded. How do you feel about being a part of so many people's daily lives? Do you feel that?

[B]

I feel. I mean, it's sort of amazing, right. I really try to not take it for granted because, you know, everyone who makes stuff experiences this at some point, which is, like, I've made a lot of stuff that no one cares about, and it's, like, impossible to get anyone to look at your thing or care about your thing that you've, like, worked really hard, and, you know, you get used to that, and that's fine. And so I feel very lucky and grateful that something I'm doing that I love doing, that I work hard at is something that people care about that is amazing.

[A]

How separate from it. Do you feel like. Do you feel like you are in there? Do you Feel like people see you in it and they personify you as a connection sport.

[B]

Now I'm just imagining just a lot of squares.

[A]

That's your new Halloween costume this year,

[B]

probably. And that's okay. It's like, whatever. What were they gonna think anyway? You know what I mean? It's like thinking that versus thinking nothing. I don't know. It's fine.

[A]

Yeah. I am, like, jealous of you in a way that there's this one. There's this very limited way that you get to create for people and they get to see you through this lens that you have a lot of control over. Where I have set myself up in a way that I have chosen and that there are lots of advantages to. But to have a lot of me to be interpreted in a lot of ways.

[B]

Yes. Yes.

[A]

Yeah.

[B]

How do you manage that? How do you sort of separate or do you.

[A]

It's the biggest question in my life. I mean, this sort of big piece of that is like, what you see is me, but not all of me, you know, with you, like, we know that. You know, we know that what I'm seeing is something that you have made, but it is not winnow. Whereas the way that I do what I do, it looks like you're seeing all of me, but it's not. I want people to understand that, and I want to, like, signal that in ways when I can, but I forget to. And there's advantages to not doing that, and I'm glad to have been doing it for a long time so that I have both built up tools for doing it better and for handling it when it goes badly. But, yeah, it is. It's wild, man. I think anyone creating in public is volunteering to be misunderstood.

[B]

Yeah.

[A]

And we all. And that's why everybody thinks you're bad. Evil. Mean. Witch. Winner.

[B]

Cool. I always think of how lucky I am that making puzzles or whatever is something that people feel very passionate about. But like you said, low stakes, basically zero stakes. You can be mad, but it, like, doesn't matter. Right. Whereas, like, there are real things in life that are important and high stakes and serious and people care about, and it's like, that's hard. That's really hard. But, like, our thing is easy, you know?

[A]

Yeah. What do you think about, like, low stakes activities as, like, important in life?

[B]

I think they're important. Like, Sudoku is. I mean, I wouldn't call Sudoku important, but, like, it's something that I just, like, do. I don't know.

[A]

Well, important is the interesting word there.

[B]

Right? Right. Right.

[A]

Because, like, it kind of can't be important if it's low stakes. But also maybe, like, the very fact that it is is what is important.

[B]

I think it's good to just have a thing that doesn't mean anything. You know, I was just thinking about the idea of, like, maximizing and how much, like, energy I spend trying to think of, like, what's the best way to do this, what's the best whatever. And it's like, well, I'm pretty sure the amount I've already spun my wheels and like, the amount of, like, mental anguish I've put myself through even thinking about that is not the best way. Like, I've already kind of messed it up and it's just like, maybe it's fine to just do stuff and it doesn't matter and it, like, who cares?

[A]

Yeah. So I don't like to start with biography, but I like to get into it a little bit. You were a crossword editor. From whence did this come. It seems like a hard job, even if you're good at it, like, to actually get the gig, I think, with

[B]

like, any sort of niche thing. There's no school that you go to, like, you know, for a journalist, you can go to journalism. You know, there are sort of, like, ladders that make sense for, like, a lot of things. But I mean, you know this, right? Like, how did. Yeah, right. Like, for certain other things, there isn't necessary clear cut path, which is actually one of the cool things about puzzles, because everyone kind of comes at it as a hobby, as an enthusiast, from different backgrounds and stuff. So I think that with the crossword, it's a relatively small community of sweet nerds who really like to do puzzles. And with the Times, there's an open submission format. So all the puzzles that are published are submitted by just anyone. Anyone can submit a puzzle, whether you're a professional constructor or just like, first time just trying it out for fun, whatever. And so the editors review all the submissions, and then it's sort of in some ways, like your resume. Right. Like, everyone kind of knows everyone's work because everyone's a fan of everyone. You see different puzzles run in different publications, but I think that, like, from the editorial side, you kind of know what people's puzzles are like. And so editing crosswords, a lot of it's just like writing clues. Right. So I think the editors kind of have an idea about how you would write clues. And every venue has a different voice. Yeah, I was submitting a lot of puzzles at the Times.

[A]

And do you paid like one off? Like, they'll be like, yes, we like this one. Here's your money.

[B]

Exactly. Yeah. Everything's on spec. And then.

[A]

Yeah, yeah. But you had to like start writing crossword puzzles. Were you like a puzzler?

[B]

Yeah, I was solving the Times puzzle for maybe like 10 years or something before I started making them. Yeah, everyone I know who is into puzzles makes puzzles. Like we all start the same way, which is just.

[A]

You become obsessed with doing crossword puzzles.

[B]

Yeah, exactly. Yeah.

[A]

Like, when did that start for you?

[B]

I think it was like maybe my like mid-20s. And it's because I had a crush on a guy who works at like all things. Yeah.

[A]

This is why I know so many words to Rush songs.

[B]

Really?

[A]

Uh huh. Who had a crush on a girl who was super into Rush and then she was like, why do you know so many Rush songs? And I was like, weird coincidence, huh?

[B]

Exactly. I would like walk by and I'd be like, oh, you're doing the New York Times crossword. I do the New York Times. I'd never done a crossword before, but I like would just.

[A]

You lied.

[B]

I lied.

[A]

You lied.

[B]

Yeah.

[A]

And then you were like, I got to get good at this fast or he's going to find me out. And what's he doing now?

[B]

I don't know.

[A]

He's not in the other room.

[B]

He's. No, no, no, no. We became friends doing this. We became friends doing this and we actually went to a tournament together. Yeah.

[A]

Oh, wow. And then you like play semi professionally or whatever it is. I mean, you're not making money, but it's like you're actually like engaging in. In the community of crossword solo.

[B]

I think that that's the right way to put it. There are crossword tournaments and there are people that are competitive, who are the best in the world and are extremely fast and very good. I am not one of those people. I compete in the loosest sense of the word. But it's just a thing that takes a solitary pen and paper pursuit and it makes it social. So you get to meet other people and other people who just like solving puzzles. And that's where the community goes.

[A]

And do all of those people dream of someday becoming Winnow?

[B]

No. Why? Why?

[A]

I mean, it does feel strange to me that there is like, you know, you have a fan base in a way that, I mean, I don't know, maybe there's other crossworders who are like. There are people who are really into their work. I assume this is true.

[B]

I Think so. Like, I think most people just are like, oh, all crosswords are, like, made by an AI. Right. Or, like, made by a computer. Right. But I think that the people who know that there are people who write them and construct them, they're the people who, like, there's good ones and bad ones and, yeah. Like, oh, I love their work. Their work, you know?

[A]

So when I get a game sent to me, a new game, I think that the thing that is hardest isn't creating the game itself. It's creating all of the games. It's actually writing each individual puzzle, which is a huge amount of work, especially when people aren't paying attention to you yet. And to be like, here's my next absolute labor that I have been grinding on for the last week that isn't going to necessarily get seen. The writing really matters.

[B]

Yeah.

[A]

And I think that, like, we can miss that because we think, oh, I know what connections is 16 words. There's four different categories. There's four words per category. But that's not really what Connections is. Like, if I made a Connections board, it wouldn't be Connections. Like, Connections is specifically the version of Connections that is done by the New York Times, and right now it's done by you.

[B]

I want. I mean, I. Oh, yeah.

[A]

Interesting. You disagree.

[B]

I don't know if that.

[A]

Like, you think if I did a Connections board and was not edited by the New York Times, that would be a Connections board?

[B]

Yeah. Why not?

[A]

Well, because. What about Only Connect?

[B]

What about. I mean, you know, I feel like they're all the same. I don't.

[A]

Only Connect is a British game that is very much like Connections, just for people who.

[B]

Well, I would say the other way around, which is Connections is a lot like Only Connecticut. The order is important. The order is important.

[A]

This may, in fact be the topic of some sensitivity that I'm not aware of. Is that the case?

[B]

I think Only Connect is amazing. I think Only Connect is really wonderful.

[A]

Okay, we're not going to get into it. We're not going to get into it. We've been instructed by the New York Times legal team to not talk too much about the relationship between connections and Only Connect. That's great.

[B]

I didn't say anything, But I think that the game is, like, the format, but I think there's space for a lot of different ways to do it. And so I, by no means consider, like, my voice to be like.

[A]

No, I don't think that your voice is. But I think in the same way that you were saying, like, different crosswords different publications have their voice, have their way of doing it.

[B]

Yes.

[A]

If I wrote a connections board for the New York Times, I would write it differently than if I just wrote it for my social media. Yeah, Very different.

[B]

I agree with that. Yeah, yeah.

[A]

And when I say if, I mean when. Whenever the door is open, I will be submitting.

[B]

So, like, we don't accept submissions. We only do that for the crossword because it's really hard to maintain a submission pipeline.

[A]

Oh, for sure. Connections would be so hard. I don't think that you should open to everybody, but I do think you should open it up to me.

[B]

Noted.

[A]

Is there a way that the game part of the New York Times team is, is it like a fun place? Is it like a serious place? Is it collaborative? Is it creative? Is it, like, locked down?

[B]

It's great. The other editors are really, really wonderful. And it's just. It's really fun to work with them. It's just like, get to talk about puzzles all the time.

[A]

Probably simpler and less tense than the newsroom, I imagine.

[B]

So the thing that we do is so silly. It's like, is this a good wordle word? Thumbs up, thumbs down.

[A]

I remember once I was opening up Connections to play because the conceit of my YouTube videos, if people aren't aware of this, is sometimes I'll get really mad about stuff and I'll have to calm down and I'll be like, I'm gonna play Connections real quick. And one time I accidentally just opened the New York Times and I was like, no, that's the opposite of what I wanted. It was like, such a weird thing that the New York Times both contains the day's horrors and the day's distractions. I think all the time about the pre New York Times era of, like, Hurst and Pulitzer yellow journalism and like, how the world that we exist in now is kind of reflective of that, where really everything's about how do we get and keep attention. And that has very much superseded credibility. That's coming back now where it's like, if you would like to have my attention, I would like for you to be credible. But for a while there and still that didn't really matter. It's like authenticity took the place of credibility where it was like, yeah, but he seems like the kind of guy that is legit. He thinks about things the same way I do. It doesn't matter if he changes his opinion every episode. And like, that was a bad time and led us to bad places. And I think that, like, we're having that on steroids right now because, you know, to do yellow journalism, you had to have a big city, really. And now you don't, because everybody's in the same big city. As long as you're on Facebook, you play the weirdest possible role in that, of being a way to pull people into the part of the media ecosystem that still lives or dies by its own credibility, which is wild.

[B]

I did a little presentation internally a couple weeks ago. I was just talking about how to brainstorm for connections, whatever. It was this fun, kind of lighthearted thing. And then everyone just falls silent and, like, turns their head and someone else walks in the room. It was Jodi Kanter, the incredible, incredible journalist.

[A]

Wild.

[B]

I stuck around to watch her presentation and just listening to her talk about her process of what she does, it was so inspiring and so incredible and such, like, hard, amazing work that I really did feel very lucky to be able to contribute in some way to support that work. That's the real. Like, that work is so important and so hard. And I really felt lucky.

[A]

Yeah, that's an interesting thing, too, because, like, I don't know, you probably don't think to yourself, like, maybe I could take connections and run off and start my own thing, but I could make more money if I have my own app. But, like, why would you want to when you're part of a big, cool thing like that?

[B]

It felt. Yeah, it felt very cool.

[A]

How often do you think about running off and starting your own thing?

[B]

I don't think I'd be very good at it. You know what you were saying about liking why you like puzzles? Sometimes you just want to have a job. You know, it's like, tell me the job. I want to do a good job. And I feel like there's a sort of other kind of brain that maybe you have, which is like, all the possibilities and, like, what can I make out of nothing? You know, it's much less intuitive, I think, for me to kind of think like that.

[A]

Wina may say it's not intuitive for her to create something out of nothing, but Winna Lou does this all the time. Actually, she is an artist, though she does not use that word. I'm not just talking about the artistry of her puzzles. She makes sculptures and jewelry. During our conversation, she's wearing a necklace and a ring that she made, and there is a white geometric deer head made out of some kind of plastic hanging on the wall behind her. Winna is a maker, and I ask her if that's why she is drawn to constructing Puzzles. Does she feel like she's building a thing when she's making a puzzle?

[B]

Yes, I do.

[A]

I love that you answered that question that way. That made me feel so good. I did a good job.

[B]

I think I've had a fraught relationship with the idea of being an artist. What I've landed on is I like to make stuff, but I've sort of tried to understand, and this is maybe my best working theory right now, is that, like, everyone's like, a different kind of learner. But it's like, when I get really into something in order to, like, learn more about it or experience it in a different way. Making something that you think is cool is one way to do that. I got, like, really into, like, practicing yoga, and I just, like, did teacher training because I loved yoga so much. And then I became a yoga teacher, but that was not the intention. It was just like, I can't get enough yoga.

[A]

I had this experience in college where I was like, I love chemistry so much. And then I went to work in a lab and I was like, I like learning about chemistry so much.

[B]

Exactly.

[A]

Can you describe the ways that your work works? A little bit, yeah.

[B]

The only thing I made on my wall is that deer thing. And that was made with, like, these white plastic pellets that you can melt in hot water. And then it's like a prototyping material. But I got really into magnets. Or do you want to see my. Hold on, hold on.

[A]

Okay. While it's gone, I'll do my best. She makes things that are constructed and that are three dimensional and that feel. Ooh, that's freaking cool. You guys, it looks like a magic trick.

[B]

This is a lodestone.

[A]

It's a lodestone that is bound in wire and on a chain, and that it is defying gravity by pulling the chain upward into a magnet.

[B]

And it's just, like, cool to see a rock wobbling around, but it, like, naturally occurs and it's just.

[A]

Yeah, it's cool. Seeing a chain brought taut by nothing. Magnets.

[B]

Right. I don't know how a magnet works. Here's another one. These are, like, little pulleys.

[A]

Oh, my God. That's cool. So I will attempt to explain that it's a brass contraption. It had two pulleys, I guess, for lack of a better term, wheels, that the chain was going around, and then the chain, you can move it, but there's a gap in the chain that is being held together by magnetism. And so you're moving the chain, and there's empty space in the middle of the chain as it goes around these two wheels. What? You have just convinced me, and this is gonna be a wild sentence to say, but by showing me your art, I am now convinced that I cannot make a connection. Sport.

[B]

No, no, no, no, no. That's not the takeaway. That's not the takeaway. That's not the takeaway.

[A]

I would never have made anything but one that cool, two, that, like, aesthetically pleasing on top of being cool.

[B]

Oh, thank you.

[A]

And that makes me think that, like, what you are doing inside of Connections is actually more complicated than I think it is. And I've thought a lot about it.

[B]

This is something that I feel like I see in your work, too, which is I identify as an enthusiast. You know what I mean?

[A]

What a great word. I came late to the term bon vivant. I had never heard of this word until, like, five years ago. And then I was like, maybe that's what I am. And Catherine was like, there's, like, connotations there that maybe are a little. Not like you, but enthusiast.

[B]

Right.

[A]

Is very good. If only we could all be enthusiasts. And I feel like it's an occupation. Not an occupation, but an identity available to all.

[B]

Yes. Yeah. But everything starts there, right? I sort of believe that the number of hours you spend doing something or thinking about something is, like, no effort's wasted.

[A]

Yeah.

[B]

I like being interested in things and learning about how to make stuff. I'm really into, like, fabrication processes. I got really into machining. It's just, like, fun to work with materials and learning how tools work, because it just makes you feel really connected to the thing that you're making, which is why I think it's, like, sort of different, the thing I get out of it than, like, art, you know? I don't think that there's, like, no overlap, but I think that, like, the thing that's very interesting is, like, how things are built and put together.

[A]

It does not now surprise me that you ended up in a job that you didn't go to school for. That makes perfect sense. Also, you said, this hit me really hard. No effort is wasted. Wow.

[B]

Maybe it's something I tell myself for all the hours I've sort of spent pursuing frippery or whatever.

[A]

But why do you think that is?

[B]

I think if I'm doing something engaging that I'm interested in, it doesn't matter if it ever becomes anything. You know, it's, like, not about an end product. And maybe it's only one of those things that Kind of makes sense. Like, when you take a step back after, like, many years, and it's like, how did I get here? And you're like, oh, there's no straight line. But no one's surprised when you're like, oh, I did this, this, this, and now I'm here. It's like, yeah, that makes sense, right? Like, you probably wouldn't have ended up there if you didn't do this, that, and that. So that's my new working theory that, like, you know, this stuff, it means something. It goes somewhere.

[A]

Do you have any sense of why you felt safe doing that? Why you felt like it wasn't important for you to always be doing something that was working toward a goal?

[B]

In some ways, it's because I, like, I'm very close to my parents. I love my mom. She's the most wonderful person, but she's also very pragmatic. And I've always, like, loved doing, like, little art stuff for her. She's just like, you know, you need a job. And I think that makes a lot of sense. But I think that I sort of compartmentalized the idea of making stuff as just, like, a me thing. You know, that's something that I could do. And it is always, like, something that's, like, stayed with me. I never tried to, like, make it a job, a career, you know, I never tried to be an artist. I just always was able to make stuff. I don't know if that makes sense at all.

[A]

It does. I don't know that it answers it completely, but maybe it's not a thing that happened to you. Maybe it's just a way that you are. I think that I'm somewhat the same. I don't know. I may not be. I remember this was, like, one of the saddest moments of my mom's life. We were, like, walking together in Yellowstone national park, and she was like, why don't you ever draw anymore? And I said, it's just really hard to monetize. And, like, completely, honestly and openly, I was just like, that's, you know. And at that point in my life, I was.

[B]

How old were you?

[A]

I was probably in my late 20s. And that was really very important at that moment because I had been scraping by for a long time, and I felt some amount of guilt about the fact that I didn't have student loans when a lot of my friends did. I felt guilt about asking for help with rent when nobody I knew could do that. And I had kind of fixated on that as the goal that I Need to have this number go up so that I can have a situation where I am and am like worthy of all of the luck that I've had. And it turns out there's no getting to there. But I didn't know that then. There are still things though that I. And maybe the whole time there have been things that just hasn't been, I think, as maybe pure as what you're describing. When I have felt like this is really just about doing this thing and seeing where I go as I'm doing, it's so great that the world gives us those opportunities. As simple as a YouTube tutorial or the building material you were talking about with the deer that's on your wall, whatever that stuff was called, didn't exist in the 16th century. I'll tell you that.

[B]

I've been extremely, extremely lucky and privileged to have support for my family and to take art classes and pursue things and go back to grad school and stuff.

[A]

But you didn't feel locked into any particular direction by your parents or that they were expecting or would be disappointed.

[B]

So my parents have a radio business.

[A]

Have a radio business?

[B]

Yeah, I've always worked in the radio business.

[A]

What is a radio business? You can have a radio business. You can work in radio. Rupert Murdoch has a radio business.

[B]

They own and operate AM radio stations. Oh.

[A]

So okay, they've got a radio business.

[B]

So my dad was a DJ in Taiwan in the 50s. My dad is 90 dope. Yeah. Yeah, it's amazing. He like played Elvis and he played like rock and roll music and his dream was to come to the states and to have a radio station. My name is actually an acronym of my parents initials, but the W is because my dad thought that whatever comes first, our daughter or a radio station, we're going to name W Y N A. They're both going to be called W Y N A if it was west of Mississippi. Call letters are K, blah blah blah. So it might have been K Y N A, but they ended up in New York.

[A]

So you had to stay on the east of the Mississippi. That was not an option. That's amazing.

[B]

Yeah, so radio was always like my dad's dream since when he was, you

[A]

know, where is wina?

[B]

So WYNA actually doesn't exist.

[A]

Oh no. So he could have got it, but he didn't.

[B]

My parents had like a big break when I was maybe like 10 or something and got their first FM station which. So the call letters are for FM stations and they were gonna change the call letters to wyna. That was the whole plan. Right. For decades, this is the way my mom tells the story. I don't remember, but she said, they told me, they're like, we're gonna change it, so it's gonna be Wyna finally. And I was like, no, you told

[A]

them to not change it. He could have had his dream. You denied it.

[B]

But then later she said that they sold it. And my mom did later say. She was like, you know, it would have been harder to sell if it was named after you. So everything kind of worked out.

[A]

Oh, well, I've looked it up, and there is now an adult hits radio station in Calabash, North Carolina. Wyna.

[B]

Wonderful.

[A]

So, hey, 104.9 Bob FM. So it's a real thing now. It looks like the call sign has been passed around a few times over the years, but that's wild. So they're in the radio business. They have AM radio stations in New York City.

[B]

Yeah. In other states, too.

[A]

Oh, my God. Is it English language? Is it specific for.

[B]

It's many different languages, actually.

[A]

Gotcha. Okay.

[B]

Yeah.

[A]

Fascinating. He wanted to be in the entertainment industry. He made that dream happen for himself.

[B]

And so I guess after many struggles. Oh, yeah, No, I imagine, like, many, many iterations. Trial and. Yeah, it took a long time.

[A]

Yeah. And then they were open to you kind of doing whatever you wanted to do professionally, question mark.

[B]

There was just this expectation that I would work in the family business. And so, like, I would always work with them part time and then kind of do other things. And I'm just not very, as I mentioned before, very business minded. You know, it's not super intuitive. And so I've always just kind of liked doing weird little things. And when I was applying for the job, at the times, I told my mom, she was like, okay, great, congratulations. And it was very lovely. Yeah.

[A]

Do you feel like there is any overlap between your parents business and yours? Like, you're in mass media.

[B]

Oh, my God. Interesting. I. I've never thought about that. That's a great question. You know, for that, I guess. Yes. I truly never thought about that. That feels nice. Oh, yeah. I have a lot of respect for my parents. I've just seen them work hard my whole life and stuff, and it's, like, cool to feel, you know, connected to that in some way.

[A]

I. I know nothing about your parents, and I have a lot of respect for them.

[B]

Thank you. Thanks for saying that.

[A]

I saw you said that. It seemed pretty amazing. Well, yeah. I mean, people are, like, playing along with you. It does feel like I am In a way, playing with you like, you are in there in a way that I never imagined with a crossword or with Sudoku, which, like, I know that people make Sudoku puzzles, but it just

[B]

is math, you know, there's also the benefit because I, like, learned so much making the game as it went on. You know, there's like, a lot of kind of trial and error.

[A]

I've watched you figure out how Connections works.

[B]

Right? Right. Yeah. Yeah. Sort of like that. And I feel like in that way, because the game has changed and solvers have gotten better, there is sort of like a feedback cycle that kind of goes back and forth, and then you

[A]

have to work hard to not have the barrier of entry get too high.

[B]

Yeah.

[A]

Where it's starting to be like crosswords, where it's like, in order to play Connections, you have to play Connections.

[B]

Yeah, it is.

[A]

Which I do feel that sometimes, but I also still think that you should still be more mean. Can I give you an example?

[B]

Yes, please.

[A]

So on the thousandth day of Connections, there was a special Connections board that you got a special badge for playing. And this was a fun puzzle, but I wanted it to be mean. So the first line, sometimes in Connections, the first four words across the top say something. And this one said, one thou sand. And then the logo for Connections. And then the first thing that I spotted, and I think this is probably the case for most people, was thou being part of Wherefore art thou Romeo was the category. I really wanted that to be the red herring and 1000 connections to be the actual category. That would have been so mean.

[B]

That's great. Yeah. Taking some notes.

[A]

Everybody would have been talking about that. And that's part of the thing. You probably don't think about the way that the Internet deals with information in the way that I do. At least where, like, I'm always thinking about how will a message travel? What will get people to click on something. I'm thinking about this in terms of the way that nefarious actors commit their annoying little misinformation crimes on the Internet. And, like, rage is a huge part of it. And so, like, you should once a month be really mean. It will be good for the business.

[B]

Interesting.

[A]

Like, that's what gets people talking about it. Cause you've done this before. You've had the first line look like the red herring, but not be the red herring. And that's a moment that everybody's not gonna shut up about. But, like, you're not hurting anybody and don't do it all the time.

[B]

How often? Right. It's true. It's true. Because there was one board, the one that I'm thinking of said, lions, tigers, bears. Oh, my. You're like, that's not a category. But that was the category.

[A]

What I'll say, as a person who's had people be mad at him on the Internet. It's part of it. It's part of it.

[B]

Do you have a thick skin or do you like.

[A]

It really depends. It depends on the thing. If it's simple, then yes. If it's complicated, then no. Like, if it's hard, if it's actually, like, a difficult thing that I don't know how to handle, well, that's always very difficult because it's not really about people being mad at me. It's about whether or not I've done harm. And that's hopefully not something you have to worry about too much, though. Certainly there are things you have to be careful with in any media. So I'm going to ask you a question I asked at the very beginning again. Why do we do puzzles?

[B]

I think we do puzzles because it's like a fun and safe way to use your brain. You know, it's like. It's just. It's something that hopefully you do and you can expect at the end you'll get, like, some satisfaction. It's just like a nice way to do something. Isn't that consequential, but makes you feel kind of good after you feel good after you've solved a puzzle, there's something about it feeling knowable, and then you can just like, move on with your

[A]

life that highlighted something that's really important, safe. Because when I play connections that are just like from the connections subreddit, where people make their own connections, I don't feel safe because I know that there is, like, a fairly high possibility that it's a bad puzzle and that the reason I can't get it is that the writing is bad. But when I'm playing Connections written by Winna Lou, I'm like, I know that this puzzle will not betray me. It may get me, but it'll get me in a way that I'm like, ah, she got me. It'll make sense. And not like, oh, that's just a bad category, though. It may betray me in the way that you assign the words to the color. And I know that we haven't talked about that. And I know that that's like the chief frustration everybody has with it, but I have this frustration.

[B]

Let's get into it. Let's do it. Hit me.

[A]

You said on a podcast recently that purple was usually, almost always when it was about the construction of the word rather than the syntax or the meaning of the word. In the last week, that's not been true, like, four times. Oh, no. I should never have listened to this podcast.

[B]

Well, I'm sorry for. It's a very loose rubric.

[A]

A very loose rubric. Until you said that, I never thought that that was the case. I thought that it was literally like, which one was the hardest among your beta testers?

[B]

So there is a question on the tester feedback form that is like, did the colors match your solving experience? And if there is a consensus for a change, everyone's like, this, yellow is really blue, or whatever. I'll happily make the change. But the way I feel about it is, I think difficulty is really subjective because it's like, sometimes people just know a lot about music or something and someone knows a lot about movies. And one isn't necessarily harder than the other. It's very context specific. And sometimes something's hard because there's overlap. So you solve it. But it doesn't mean the category itself was harder. So I feel like there's different reasons something might be harder, which is why I try to move away from how maybe hard something is in terms of assigning the colors. It's like, oh, if it's a trivia thing, that'll be blue. If it's more specific, and if it's wordplay, it'll usually often but not always be purple. And if it's the yellow and green, which I have heard called grello or, you know, whatever.

[A]

Yeah, they're all. They're very similar.

[B]

It's very similar. And I don't think there's always a clear. Yeah. And so it's like, my general sense is like, if there's like a word that clearly defines the category that's like, not that ambiguous, that'll maybe bump it to yellow. But like, if parts of speech and, like, words are vague or like the group of synonyms is harder to see, then that'll be green. But it's very like, loosey goosey. You know, I don't feel like there's always, to me a clear thing, which is why I'm happy to outsource that. Like, I'm not very attached to the colors.

[A]

The problem is that we have introduced upon you the idea of getting the reverse rainbow, which is not. You didn't do that. We did that.

[B]

But now there's a badge.

[A]

I think now there's a badge. So you did do it. And now it does matter to me. I'm a little worried more than it used to.

[B]

You can always tell me what your opinion is.

[A]

Okay, again, we're new to this podcast, but I'd like to ask you a question that I'm thinking I might ask everybody at the end of the podcast.

[B]

Sure.

[A]

What is something that you have learned from this work that you wish everyone on earth knew?

[B]

There's an idea that things can evolve. You know, that you don't always know when you start doing something what it's gonna be, and that's okay. It is okay to build in some knowledge or expectation that the thing that you start doing will not be the thing it is a year down the line or whatever. And you don't need all the answers first. You don't need to know everything that you're gonna do or say or whatever, how it's gonna go and just doing it and like, doing wrong stuff and, like, doing a bad job is okay. And kind of like, I guess iterating and just being like, okay, well, the whole thing is a process, and that is okay. There's no good or bad about that. That's just kind of the way it is. And maybe also being just open to that and also knowing that the sort of no effort is wasted kind of thing maybe is tangentially related to. You will do a lot of stuff. You'll put in a lot of work that doesn't go anywhere, but it's part of the process, and that is okay. And it does something even if you can't quantify or see it or it's not material. So that is something that I have believed and I feel like I've gotten out of doing this for a few years.

[A]

This is very much true of my work where, like, John and I started and we were making a video blog every weekday, and the response to every video affected the next video in a really deep way. It makes me feel like the thing that you're doing is also a collaborative enterprise where you're building from our reactions and from our failures and from our successes and our frustrations. And you're, like, playing the game with us that you want to play with us.

[B]

We're all learning. We're all in this together, Right? Yeah.

[A]

And, like, of course, you would never know what it's going to be. And it's almost crazy to me that you had to write the first. Did you say 60? Without that feedback. And you're also, like, learning from the. The structure of the game. The game is teaching you how it can be played in new and different ways.

[B]

The constraints, Right.

[A]

Yeah.

[B]

Very hard to invent your own rules, but sort of easier in some ways to follow rules and just see where that takes you. Yeah. What would your advice be for the same question? Do you have an answer?

[A]

No. It's not about me.

[B]

Sorry, sorry, sorry.

[A]

Thanks to all the humans who helped make this episode. Morgan Levy is the show's supervising producer, and Greg Rippon is our engineer. Peyton Mitchell manages our social media. Andrew Huang composed the music, and James Barnard designed the artwork. You can and should follow us wherever you listen to podcasts.

[B]

Let's do it one more time.

[A]

Humans.