Dan Cassaro

Dan Cassaro is a wise man. A graphic designer, illustrator, animator and an excellent hand-letterer, he spends his talent and time using typography to make words accountable for themselves.

Dan is the founding force behind a small but scrappy design practice based in Brooklyn, called Young Jerks, which focuses on type, lettering, logo design and 70s rock. His client work includes Carhartt, Billabong, The New York Times, ESPN, Rolling Stone, Levi’s and Lands’ End, just to name a few.

In his words, he is just trying to herd his horses. In our words, he is saying big things with simple words. On top of travel and design, Dan and his wife just announced that they are expecting their first child. Congrats, Dan!

Q. What is your least favorite letter?

J is pretty shitty. I say that because it is a nightmare to draw as a simple sans serif and also as a fancy script. Whenever I do it, it always ends up looking a little malnourished.

Q. What is your favorite show on Showtime?

Dan Cassaro No RegretsI have no answer for this. I was going to say that I only watch porn.

Q. Coffee or cigarettes?

Both! But I just quit smoking a year ago, or maybe a little longer than a year ago. I don’t miss the 16 other cigarettes I’d smoke a day, but I do miss the one or two I’d smoke with my coffee.

Q. Jeff Rogers told us to ask about your wedding reception.

Umm, our wedding reception was great. I danced with my mom to Rainbow Connection. There was a lot of Bruce Springsteen. My wife and I love the song “Shout” and specifically dancing to the song at weddings, so we had two showings of the song, an early showing and a late showing, because we didn’t want to do it just once. I’d say that was an interesting centerpiece to our wedding reception, multiple playings of the song “Shout”.

Q. Jeff Rogers also said that when he first met you, he confused you for Jon Contino. Who could you confuse Jeff Rogers for?

It’s adorable now that I think about it, because Jeff is the sweetest guy in the world. But I get that all white guys from Long Island look the same. (Dan proceeds to ask his wife, in the background, who they agreed Jeff Rogers looks like) Yeah, that modern Sherlock show, the crappy one. Elementary, I think it’s called. He looks like Johnny Lee Miller from that show, especially when he hasn’t shaved but doesn’t have quite a beard which Jeff tends to always have.

Q. How many women named Judy or Linda did you work with at Lands’ End?

Dan Cassaro Lands' EndThere was a bunch of them and they were all sweethearts. There was a shit ton of Tammys and Todds, too. It’s such a mom store, and everyone there has that maternal air about them.

Q. Bruce’s butt or Mick’s wang?

This is my favorite question that I’ve ever gotten in my life. I feel like you know the answer has to be Bruce’s butt, because I need to defer to Bruce Springsteen in any situation where he is an option. But if we are doing a general 1970s rock challenge, I feel Rod Stewart needs to be in the running. If you Google any photo of him from back then, every single pair of pants he’s wearing has a perfect outline of his junk. The 70s in general were a great time to show your hog.

Q. What is your meditation mantra? If that is too personal, have any good birthmarks?

I feel like the rule with Mantras is that they have to be a secret, and if you tell people they lose their powers. But I do have a ton of birthmarks. I have a bunch of birthmarks all over the top of my head. And I didn’t find that out until I was in 2nd grade. I got a crew cut, shaved my head, and then there was a bunch of brown spots on my head, and I was like I am never doing that again.

Q. What is your favorite highway in America?

I’m gonna say Carefree Highway, which is a Gordon Lightfoot song. I can sing it for you.

Q. When’s the last time you drew a dragon or dinosaur?

Dan Cassaro Young Jerks Design WorkOh, really recently. I drew a dragon last week actually. Me and a bunch of my studiomates and friends just started, as adults, playing Dungeons & Dragons for the first time. We got together and paid a Dungeon Master to teach us how to play, and all of us are fun and creative, so we spend most of the time doodling what’s going on in the game.

Q. Would you rather be shot by an arrow once or have to wear a sombrero everyday for the rest of your life?

I would definitely do the arrow. It would be really painful, but if you are going based on stories, having a wound from an arrow in your hand is much better than the story you’d have to tell as to why you are wearing a sombrero for the rest of your life.

Q. Who was the biggest jerk when you were young?

Dan Cassaro Young JerksThere was this guy in my first grade class, and he was just a real jerk. He came over to my house one day after school and put a baseball on top of his glass of chocolate milk, and I told him not to do it. He then hit it with a Nerf baseball bat and shot chocolate milk all over the house. I told him not to do it, that it’s not like tee-ball, and he looked me in the eye and did it anyway. There was another time where he was playing with one of my trucks in class, and he broke it. He told me not to worry that he would take it home and fix it. He brought it back having smashed it with a hammer and it was in a million pieces. He was just a real jerk.

Q. What was your mom’s last Tweet?

She doesn’t tweet that much. Let me check. It was a retweet of something I tweeted. And then there is some retweeting of some Anti-Trump articles and another retweet of something I made. She is very supportive.

Q. Who is your favorite famous Dan?

I would say Daniel Craig, specifically because I really like Skyfall. I think it is one of the best Bond movies. Also, I am really impressed how he can fill out a speedo in that movie. He can wear that style of bathing suit and still look badass.

But wait, there's more....
Dan Cassaro Dumb Questions for Smart Designers
The Complete Series of Interviews

Marty Neumeier

Tarentino or Scorcese?
Chad Makerson Michael

Chad Michael

What cologne did you wear when you were younger?

Chalk & Brush

How do you feel about cargo pants?

Reyna Noriega

Q: Would you travel to Mars?

Tyler Spangler

Beavis or Butthead?
Debbie Millman

Debbie Millman

If you were in a font family, what style would you be?

Kevin Cantrell

Boomerang: The app or the tool?

Ariel Wilson

Q. Who’s Your Favorite Dad Bod?

Lauren Peters-Collaer

Q. What gives you goosebumps?

Luke Tonge

How are your nunchuck skills?

Mari Andrew

What noise does your spirit animal make?

Matt Curtis

If you were in a heist movie, who would be your assembled team?

Robert Fisher

What can you see from your window right now?

Beat Baudenbacher

What’s the last thing you apologized for?
Dumb Questions for Smart Designers with Paul Woods

Paul Woods

What is the best board game to flip over in anger?
Designer and Illustrator James Olstein

James Olstein

Would you rather drown in coffee grounds or cat hair?
Dumb Questions for Smart Designers with Victor Melendez

Victor Melendez

Where’s the strangest place you’ve peed?
Dumb Questions for Smart Designers with Courtney Macca

Courtney Macca

What’s your uncle’s name?
Dumb Questions for Smart Designers with Anna Laytham

Anna Laytham

How do you feel about sandwiches made with the ends of loaves of bread?
Dumb Questions for Smart Designers with Johnnie Cluney

Johnnie Cluney

Have you ever eaten something in a bathroom?
Dumb Questions for Smart Designers with Julieta Felix

Julieta Felix

How many bugs do you think you’ve killed in your life, whether by accident or on purpose?

Brian Van Gogh

What’s the last thing you licked?
Dumb Questions for Smart Designers with Randy J Hunt

Randy J. Hunt

If you started a cult, what would you make people wear?
Dumb Questions for Smart Designers with Jennifer Heuer

Jennifer Heuer

Do you think a world with adorable puppies on every corner would get annoying after a while?
Dumb Questions for Smart Designers with Syd Weiler

Syd Weiler

If animals could talk, which do you think would be the rudest?

Kendrick Kidd

What kind of toilet paper do you use?
Dumb Questions for Smart Designers with Lola Landekic

Lola Landekic

How many tabs do you have open on your desktop right now and what are they?
Dumb Questions for Smart Designers with Shogo Ota

Shogo Ota

What is one thing Idaho and Japan have in common?
Dumb Questions for Smart Designers with Jordan Scott

Jordan Scott

Would you allow Jeff Goldblum to tattoo you?
Andy J Miller of Creative Pep Talk answers Dumb Questions for Smart Designers

Andy J. Miller

When was the last time you kissed someone on the hand?
Dumb Questions for Smart Designers with Josh Higgins

Josh Higgins

Q. Do you have any pet names for Mark Zuckerberg?

Amy Nicole Schwartz

If you were two kids in a trenchcoat, would you want to be the head or the body?
Stefan Sagmeister

Stefan Sagmeister

Would you rather ride in Air Force One with Trump or in a tank with Putin?

Christopher Ayres

How good are you at giving driving directions in California?

Chris Costello

Do you ever hold your pee too long while drawing?
Dumb Questions with Joshuan Taylor

Joshua Taylor

What Disney princess would you want to be?
Dumb Questions for Smart Designers - Jared Erondu

Jared Erondu

Someone you just met has food stuck in their teeth, do you tell them?

Zac Petit

At what age did you get to second base? And where did it occur?
Nicole Jacek Dumb Questions for Smart Designers

Nicole Jacek

Whose hair would win in a fight, yours or Donald Trump’s?
Dan Cassaro Dumb Questions for Smart Designers

Dan Cassaro

What was your mom’s last Tweet?

Cap Watkins

Man grooming, yes or no?
DanielleEvansHeadshot

Danielle Evans

If you had to make a slogan with raw oysters, what would it say?
Darren Booth Designer

Darren Booth

Who would you rather have escort your wife to a party, Ryan Adams or Ryan Reynolds?
Lauren Hom

Lauren Hom

What is your favorite flea market find?

Mikey Burton

What would it take for you to move back in with your parents now?

Gavin Strange

What was more painful, taking a bad skate slam or designing your website?

Becky Simpson

Do you own any domain names you don’t use?

Craig Frazier

Would you rather wake up for a day as Daniel Craig or Frasier Crane?

Mackey Saturday

What is the strangest rewards program you are a member of?

Sara Blake

Are you of the old school mindset, do you hand sketch everything first?

Jess Boonstra

Harry Potter or The Girl with the Dragon Tattoo or The Da Vinci Code?

Jeff Rogers

Tell us a personal story about glow sticks or hot sauce.

Chip Kidd

Who would run the country better, Donald Trump or The Joker?

The Heads of State

What do you think of the upcoming Ghostbusters reboot? Be honest.

Scott Allen Hill

What was the most inopportune time you broke, lost or forgot your glasses?

Timothy Goodman

If Donald Trump asked you to draw something on his Mexico border wall, what would you draw?

James Victore

Can you invent a clever bumper sticker slogan? We may or may not steal it.

Veerle Pieters

Since you never have had a boss before, would you rather have David Brent (The Office) or Gordon Ramsey (Chef) as your boss?

Gui Borchert

What do they write on your cup at Starbucks when you tell them your name is Gui?

Don Clark

What is your favorite show to watch with your kids on a Saturday morning?

Harvey Shepard

Would you rather shovel snow or go to a Nickelback concert?

Tad Carpenter

What’s your favorite children’s book?

James Flames

Who would you love to have design the poster for your 40th birthday party?

Jessica Hische

Can you give us an example of one thing you wouldn’t want your Momager to handle?

Steven Heller

You’ve interviewed a ton of people. Is there one person in particular that you haven’t that you’d want to interview?

Sara Blakely

What would your first thoughts be if you were asked to write Grease 3?

Josh Brewer

Elton John or Phil Collins?

Ashleigh Axios

If you’re going on a road trip with President Obama, what kind of car would you drive?

Matthew Manos

How do you feel about the term Millennials? Be honest.

Jean Jullien

If you had to get trapped for a month in one city’s subway system which would you prefer, NYC or London?

Bradford Shellhammer

Since your name sounds like that of a superhero, what would be the name of your arch nemesis?

Jon Contino

Would you rather be the brand manager or general manager for the Yankees?