Hello! I'm Oliver Roeder, a senior writer at FiveThirtyEight, where I've written about chess, Scrabble, the Supreme Court, artificial intelligence, math, show dogs, Russian trolls, game shows, nuclear war, Super Mario Bros., art collections, the Black Rock Desert, spelling bees, and a crossword puzzle plagiarism scandal that came to be known as #Gridgate. You know ... the usual beats. I also wrangle the news stories for our daily newsletter, Significant Digits.

I'm also FiveThirtyEight's puzzle editor and I oversee a weekly math and logic puzzle column each Friday called The Riddler. My new book, The Riddler: Fantastic Puzzles from FiveThirtyEight, is a collection of the best of that column along with some never-before-seen puzzles. Will Shortz promises that it will stretch your brain in new ways—it says so right there on the back of the book. (My publisher would like me to be known as the millennial Martin Gardner, and while I love Mr. Gardner, I am also happy to bore you with my lengthy argument as to why I'm not in fact a millennial.)

Before falling into (and for) journalism and professional math-puzzle making, I was an academic: I did a Ph.D. in economics at the University of Texas at Austin (Hook 'em) where I focused on game theory and political competition.

Proof: https://twitter.com/ollie/status/1050733377182199808

Comments: 92 • Responses: 37  • Date: 

LisaMcLisaFace531312 karma

I love FiveThirtyEight in general and your work specifically. How did you come to work for them? And if you hadn't, what do you see yourself doing instead?

oliver_roeder12 karma

Thank you! I was doing a postdoc at a center housed at NYU, working on some econometric stuff around incarceration and crime. I pitched a story about that research to an editor there at the time, Andrew Flowers. He said, "Well, we're not interested in THAT right now, but I see on Facebook you play competitive Scrabble" (which I did at the time). So I wrote a piece about the world's best Scrabble player, which sort of blew up (thanks, Reddit!). They commissioned a few more pieces, then Nate Silver and the managing editor took me to lunch and gave me a job.

In the absence of that stroke of luck, I may still be banging my head against the walls of academia.

CarsonAft9 karma

Not really a question but a request:

Once you release the answer to a Riddler, could you link it at the bottom?

oliver_roeder3 karma

A very fair request!

filbertsnuts7 karma

Would you describe Harry Enten as a wiz kid or wiz man?

oliver_roeder4 karma

Are those the only two options?

ChaoticScott6 karma

Jorts or cargo shorts?

oliver_roeder15 karma

I reject the premise.

GeorgeOfTheMountain6 karma

What's the story of your profile pic on Twitter?

oliver_roeder9 karma

That's Philip IV of Spain, as painted by Velazquez! A friend of mine pointed him and our similarities out to me a few years back and another friend Photoshopped the backwards hat, which I favor in real life. He looks exactly like me


And I enjoy visiting him in The Met—it's like visiting family. Although the paintings of him later in life don't augur that well for how I will age :-/

BlunderBear5 karma

Hey Ollie, big fan.

What riddle has surprised you the most? Any answers jump out at you as surprising? Any extensions of answers strike you as being rad?

How do you like being on the Politics Podcast?

Do you try to solve the puzzles before reading solutions when they are submitted?

oliver_roeder3 karma


I think the most surprising Riddler answer I think was to the Laser Larry problem, where Laser Larry was set to destroy the pentagonal Riddler Headquarters with his, well, laser, and the Riddler mathematicians had to move their equipment to safety: https://fivethirtyeight.com/features/can-you-save-riddler-headquarters-from-laser-larry-please/

The answer turned out to involve all this crazy and cool geometry, which one of our solvers animated like so: r/https://twitter.com/xaqwg/status/752137934246146048

I love going on the Politics Podcast—though I hate the sound of my voice.

And yes, always. The highlight of my week.

spoonerm3 karma

do you play chess?

want to play chess?

Portarossa3 karma

I've been a big fan of your columns for a while, so congratulations on the book!

What is it that makes a great puzzle great, in your estimation? Do you have any examples of particularly impressive puzzles that make you think Damn, that's clever?

oliver_roeder3 karma

Thanks very much.

I think there are a bunch of dimensions along which you can try to maximize to make a great puzzle. 1) A good story really helps. 2) Many paths of approach help draw many people in. 3) A correctly pitched difficulty level. 4) An "aha" solution. 5) A solution that you can take with you and see in other problems or even in the real world. (This last point is a big reason why I like game theory problems.)

I have one that succeeds on at least a couple of those dimensions: https://fivethirtyeight.com/features/can-you-win-this-hot-new-game-show/

I'll leave it to y'all to find the solution, but the puzzle is SO simple and the solution is SO fascinating.

temp98124890143 karma

Approximately how many hours a week does it take to run The Riddler?

oliver_roeder2 karma

It really depends! Probably an hour or so combing our (wonderful) user submissions for promising problems. An hour or so test-solving them. An hour or so combing our (wonderful) user-submitted answers for clever approaches or cool charts and illustrations. A couple hours writing the column itself. Then I respond to comments from my editor and our copy editors and produce the post in our CMS and so forth.

Sometimes we'll do a participatory Riddler, like the massive Colonel Blotto battles over fictional castles that we've run. For those I've got to write some code and clean some data and so forth. Those can take quite a bit longer—but they're fun!

miclugo3 karma

Why are you not a millennial?

oliver_roeder4 karma

Why thank you for asking! I think millennialdom has everything to do with the internet. I think the cleanest generational distinction here is whether or not one has conscious and real memories of a world without the widely available internet. I have such memories. Oh, yes, do I have some lovely memories...

kyrgioat3 karma

What is it like working with Nate Silver? Besides Nate, if you could write a book with any other writer at FiveThirtyEight who would it be with and what would it be about?

oliver_roeder9 karma

Wonderful. This is the only job I've ever had in journalism, and everything I've learned about the field I've learned from folks that work or have worked here—Nate, Mike Wilson, my editor Chad Matlin, our amazing copy desk, our viz team, and so forth. They are, to a man and to a woman, sharp and generous and brilliant. I am biased but it's also true.

oliver_roeder6 karma

Oh and as for the book: my colleague Christie Aschwanden lives in Colorado and I'd like to do a sort of John McPhee book with her about a band of rogue mountain climbers or guerrilla winemakers or something. Basically what I'm saying is I need to spend more time outdoors.

SeniorWiggins3 karma

Do you all just have a bunch of cream soda in your fridge untouched these days?

oliver_roeder4 karma

I assume Harry provided a forwarding address.

James_D_H2 karma

How can I improve my odds of winning the lottery?

oliver_roeder4 karma

Buy more tickets?

Adamworks0 karma

Buy 2 tickets.

oliver_roeder2 karma

Better yet, buy three!

1sttimeAMAer2 karma

I think I have some significant digits that you might find interesting for your newsletter. Do you consider data submissions?

oliver_roeder2 karma

By all means.

EveryFreyday2 karma

Hey Ollie! I'm thinking about going to graduate school for economics. Do you have any recommendations?

oliver_roeder5 karma

I hesitate to give advice because the world is a very complicated place but I will say that a PhD is only worth the time (and effort and heartache and your 20s and so forth) if you are completely passionate about the subject and research and completely sure you want to take it on and do academic. Steven Levitt told me that—I ignored him and went anyway. And well ...

EveryFreyday2 karma

Thanks! If you don't mind I would like this to share with #EconTwitter. What about academia burnt you out so quickly? Did you ever see yourself teaching?

oliver_roeder2 karma

Share away.

I loved teaching actually. I TAed and I taught a couple classes at St. Edward's in Austin. But teaching and pedagogy are, for complicated reasons I think, not emphasized in the standard doctoral program—or at research institutions in general. It seems to me like an unfortunate arrangement which dates back to like the Middle Ages and got messed up on the way to the present.

In any case—academia is as political as any other field, and it takes energy to play that game and to do research (and to teach) and you've got to really want it.

Thatguy7552 karma

What is your favorite place to eat in Austin?

oliver_roeder2 karma

El Caribe, on Lamar, and it's not particularly close. (If I still lived there I'd be loath to let this secret slip, lest I blow up my own spot.) Ironworks for BBQ—I like the deck and it's not as crowded as other spots. Salt Lick if you're up for a drive and have a well-stocked cooler. I've never been to Franklin's so don't ask ;)

platypusgiraffe2 karma

what is your lichess username? (or worst case, Lichess rating at different time controls/variants)

oliver_roeder2 karma

It is a secret because my single biggest phobia is whatever the Greek for fear of embarrassment is.

ADoseOfTransReality2 karma

What was the hardest riddle you've received?

oliver_roeder2 karma

I recall the dog and duck and pond problem being insanely tough: https://fivethirtyeight.com/features/will-the-dog-catch-the-duck/

There was also a puzzle about a lonely king and the elimination of his subjects that was fascinating and weird and really gnarly: https://fivethirtyeight.com/features/the-puzzle-of-the-lonesome-king/

TheUnknownStitcher1 karma

On which game show would you dominate as a contestant and why?

oliver_roeder2 karma

The Wall. Is that show still on? I have a deep obsessive love for The Wall.

GeorgeOfTheMountain1 karma

It just got renewed for a 3rd season!

Wiki link for the lazy

oliver_roeder1 karma

Heck yeah! I wrote about the show once upon a time https://fivethirtyeight.com/features/what-if-god-were-a-giant-game-of-plinko/

Chtorrr1 karma

How did you first get into this work?

oliver_roeder1 karma

Sheer and utter dumb luck.

Seriously: I pitched one story and ending up writing about Scrabble instead. The story did well for whatever reason, and the managing editor liked me for whatever reason, and the rest is a serendipitous history that I will be forever thankful for and never quite believe is real. [pinches self]

bonesaw_131 karma

Any famous (or not famous) chess match you consider to be your favorite?

oliver_roeder2 karma

It's tough to beat this if for no other reason that the comedy of it: http://www.chessgames.com/perl/chessgame?gid=1259009

Portarossa1 karma

Do you have any thoughts on why the Monty Hall Problem became such a big fudgin' deal in popular culture? Are there other famous historical puzzles like Monty Hall that deserve more love than they get?

oliver_roeder3 karma

IIRC, Martin Gardner popularized something similar called the three prisoners' problem. Gardner was a genius for popularizing cool math, so maybe that has something to do with it? I also think the result is just so unexpected before you get it, and so cool once you do.

It's not exactly a puzzle but Conway's Game of Life is the most fascinating thing and I tell everybody I meet about it. I don't have a lot of friends anymore, but I reject the obvious causal connection ;)

teamcrazymatt1 karma

After your Scrabble and chess matches, what's the next competition you would like to participate in against a top-level player?

oliver_roeder4 karma

Bridge! I'm currently learning bridge—I'm both personally fascinated and am also starting to work on another nonfiction book about games, their history, and AI games-players. It's fun research.

TicketToThePunShow1 karma

I do the riddlers every week, they are great!

Sadly I've never been selected as the winner, on a given week about how many winners enter submissions?

Or, to put it in "your words", what are my odds of getting selected as a winner assuming I have a 50% successful solve rate?

oliver_roeder2 karma

Thanks for solving!

The variance is big, and the number of submissions seems to be correlated with the difficulty and type of problem in ways that I don't completely understand.

On average, on the order of 1,000, maybe?

kidsincatacombs1 karma

Does Nate Silver ever sleep?

oliver_roeder3 karma

I have never seen Nate Silver sleep, for what it's worth.

trosiello1 karma

What websites do you get your chess news from? and what books/websites/things did you use to get better at chess?

oliver_roeder1 karma

Chessbase, mostly. Chess.com. Chessdrum. A bunch of super smart chess folks on Twitter. Nothing too unusual.

I used to take lessons at the Marshall Club here in New York. But really what I do is just play endless speed games on my phone or against my buddy Brin at the coffee shop—5 minutes a side. So, in other words, there is a reason I'm not very good.

trosiello1 karma

Thanks. Wondered what other great websites you read to get inspiration for the significant digits/the riddler?

oliver_roeder1 karma

A total grab bag for SigDig: Google News, Twitter, my friends, my colleagues (we have a Slack channel), my mom, actual physical newspapers and magazines, etc. etc.

nealywilly1 karma

What other fields have you become significantly more interested in (even if just reading, not writing about) since you've been with FTE?

oliver_roeder1 karma

Very interesting question.

Meta-science first of all. Christie Aschwanden covers this really really well. https://fivethirtyeight.com/tag/meta-science/

Public health, too. Chris Herring's stuff got me more into basketball. International relations and the formal, poli sci theory thereabout.

Grantselrich1 karma

What happened to the Cubs this year? Looking forward to meeting you tonight!

Also, what other publications besides FTE do you read/recommend?

oliver_roeder1 karma

The Cubs :( That's all I really have to say about that I'm afraid.

Oh gosh tough one because there are so many... Quanta. Aeon. I love those.

madmsk1 karma

First, I love your columns.

Second, I've got a background in mathematics and I'm currently working in finance. What would you recommend to someone looking to get into the kind of quantitative journalism you do?

oliver_roeder1 karma

Read lots of journalism. Write lots of stuff. Pitch good stories.

jrlund21 karma

Hi Ollie, how do you pick solutions to the Riddler?

oliver_roeder1 karma

I pick the solutions I highlight in the column by reading through the spreadsheet early in the week. I am biased toward including cool diagrams and charts—we're 538 after all. I am biased also toward brevity—ceteris paribus the shorter solutions are better, clearer, easier for a reader to hold in his or her head, etc.

I pick the winners that I name just using a random number generator.

LightenUpAndLaugh1 karma

I enjoy the Riddler even though I can seldom make much headway in either the express or classic. Any chance you might include something a little simpler every now and then?

oliver_roeder1 karma

A fair request. We've tried to do that a bit with the Express puzzles, but difficulty is something we've struggled with. It's a bullseye that I think we're always swirling around and hit sometimes. Some solvers are PhDs in math; others are 7 years old. And I want them all to enjoy their citizenship in Riddler Nation.

somethinghadtogohere1 karma

Do you have Carlsen or Caruana winning the World Chess Championship?

oliver_roeder3 karma

Caruana +300, maybe?