What are you drinking?

This is a Japanese green tea made by Ito En. I ordered it from Amazon. My wife Hiromi is Japanese so I spend a lot of time in Japan and it’s like Coke there, it’s everywhere. I’ve never really liked coffee so I always just have these.

When it came to your role as Chief Technology Officer for Obama’s reelection campaign, you’ve said that failure was not an option. Being given such responsibility at 32, did you ever feel in over your head?

You just kind of did what you needed to do. Recently there was a study done on different types of people who are all doing extraordinary things in their lives, from documentarians who are embedded in war zones to athletes who are no-hitter pitchers. They talked to all of these people and just asked, “How did you do it?” One of the groups of people they featured were Navy SEALS and the SEALS were talking about how during training they always pushed you to your very end and then the next day they would double it, and then the next day they doubled it again and there are a couple things that I think are really interesting about that. One is that humans are very extraordinary in our ability to expand to handle challenges. The other is that we have no idea of our own limits. When things get hard you think, “Okay, now this is the baseline for hard,” but the next thing that is hard might be twice that or even three times. Very quickly you begin to realize you can a lot handle more than you ever thought you could.

Are the politically charged movies and TV shows an accurate reflection of how the world of politics really works?

It’s hard to say yes to this question because it paints us political type people in a terrible light. Because none of those movies are like, “Yeah and everybody got along! And it was perfect!” You know? But what was it, the “Ides of March”? I did not see that movie but a friend of mine who was involved in the campaign and a long-time political operative said that one hit a little too close to home and I think that happens a lot. I recently watched “House of Cards” and I don’t think that’s an accurate reflection of politics but I do think that those people are out there, the people who are the fixers like Frank’s partner the chief of staff. Those people exist, they really are around and you interact with them. It’s like the movie “Michael Clayton” where George Clooney plays the fixer for a law firm and you think, “This guy’s a mother fucker!” He’ll do anything, he’s gonna solve the problem and that’s the dark side of politics. I mean there’s no killing, right? But there is a lot of competition.

What did it feel like being on the inside of such a cut-throat industry?

It’s like being around a campfire, the middle is this person of power and everyone wants to get closer so people will do crazy things. One thing that shielded me from a little bit of that is I had no interest in going into politics so I didn’t really give a fuck about what happened next. But for some people their entire careers are built on the power that they are able to grab during that time. And this happens in every place at every job. So the question of is it accurate, these movies? I think sometimes, yeah and it’s kind of depressing. People near people of power do really bizarre things.

If you could offer 20-something dreamers one piece of advice, what would it be?

Just focus on what’s right in front of you. A musician friend of mine was talking about how when he plays shows he only sees the front row so it doesn’t matter if there’s 1,000 people or 10 million people watching, he only focused on this little tiny bit. As long as you don’t stress about the big picture it is much more relaxing and easy.

You have a great sense of humor. Is there room for that in politics?

Yeah. I think engaging in humor is probably one of the most important ways to mitigate stress and frustration, even if sometimes that means the humor is very dark.

What kept you sane during the long work hours?

One of the things that I did every night was eat with Hiromi, whether it was going to Papajin in Wicker Park randomly because it was on the way home or cooking together. No matter what we would eat together and sometimes it wouldn’t be until 11 o’clock at night but it really was an important thing to me. It was a call for me to come home from work and also a break where I could think about things, relax a little bit, talk through some stuff with her and also be there to support her in her job and her life. It was very nice to know that we could do that still even though it was a very busy time.

Self-proclaimed one of the coolest guys ever, what would you hope people say is the coolest thing about you?

Obviously my modesty and how humble I am. [Laughs] No, I don’t know. That was a funny thing. A good friend of mine Jake Nickell who hired me at Threadless is really fun and he had something like “World’s Coolest Guy” on his blog. It was back in the day when SEO was really important and his goal was for people to search for the world’s coolest guy and for him to be the first one that came up. So I was just like, “Fuck it, I’m gonna be the awesomest!” and we had a little competition going. Then it became this thing where people would look for information about me and the only thing they could find was my bio saying that I’m incredibly awesome and then people started publishing it. So now it’s like, what else can I put in there? Incredibly successful and good looking?

Do you read your own press?

I don’t watch speeches. I don’t read articles but I’ll have other people read them. I’ll just ask my wife or my business partner Dylan [Richard], “Can you let me know if it’s good or bad?” There hasn’t been a lot of bad press but even the good ones I don’t read. I will read comments though because they’re fuckin’ hilarious. I tried to watch one of my speeches once but then was like, “Fuck that!” because it’s embarrassing, right? It’s like hearing your own voice, most people don’t like that because it sounds super weird … It’s been fun but very bizarre. Now I have this box of magazines and articles that I want to frame or put on a wall or something but I don’t know. A friend of mine has that where you go to his house and he has a whole wall of all the press he’s gotten and you’re just kinda like, “Really?” It’s kind of silly. I think one of the biggest lessons I’ve learned is one that I have hanging in my office that says, “You’re never as the press says you are.” That’s a really important mantra because the story that the press says is never the real story so you always have to make sure that you’re 10 times as good as what is written.

Last time you’ve been in a suit?

I don’t own a suit but I do own a tuxedo and the last time I wore the tuxedo was at the Inauguration.

It’s midnight on a Saturday night; what are you typically doing?

Man, usually reading. I used to spend a lot of time at clubs but I’m 36 now. I’m almost dead.

Most influential book you’ve read?

“Hackers” by Steven Levy had a big influence on me because it showed that you don’t have to follow the rules and in fact all these people that you admire never followed the rules either.  I think not following the rules is a really important part about technology because if we all just followed the rules we’d never have these groundbreaking apps like Google or even Snapchat.

What would it take for you to shave your facial hair?

Nothing, just boredom. This is 100 percent based on the lack of shaving, not based on the want of a beard.

Last time you were embarrassed?

Sometimes my inner bro shows up. I said something to my friend recently and he was like, “Harper, that was a little too bro. You don’t have to be like that.”

If you could have a drink with anyone, who would it be?

Maybe Richard Feynman, a physicist. Or maybe David Bowie? That’d be fun. The problem is people are always people, it doesn’t matter the things that they’ve accomplished or what they’ve done at the end of the day they are just a normal person. All of your friends and all of the people around you, those are the ones that you should be having drinks with. It’s like the idea of, “What would you do with a billion dollars?” You’d hope that you would just hang out with your friends and family, right? And just do what you’re doing now but just in much more gold. Obviously I’d wear gold pants and a jetpack.

KIRSTEN MICCOLI / A DRINK WITH