Josh Gondelman: comedian, writer, former teacher, and all around fantastic cardigan-loving guy. You may know him as the co-creator of the genius Modern Seinfeld Twitter handle. Maybe you have seen his work in esteemed publications like The New Yorker, New York Magazine, and McSweeney's. Or could it be that you have seen him on a stand-up show around New York City or a comedy festival? No matter where you've seen him, he's definitely one of New York's most talented entertainers, and I was lucky enough to get an interview with him.

Tell us a little bit about yourself. Where did you grow up? What and who has been influential in your life? What do you like to do in your spare time?

I grew up just outside of Boston in a little town called Stoneham. My family is great. I have a lot of wonderful friends from there. I'd count them all as influences. When I was a kid, I was really into Mel Brooks and SNL. Those were definitely formative comedy touchstones for me. I also very much consider myself influenced by Massachusetts townie-ism.

What are you doing now for work?

I'm a writer for Last Week Tonight with John Oliver on HBO. It is a very fun job, and I'm very happy to be working there!

That sounds pretty amazing. John Oliver is great. How did you get your start? Did you always know what you wanted to do?

I did a lot of sketch and improv in college, and I started doing standup after my freshman year at Brandeis. I always knew I wanted to write, and I intentionally went to a school where I could do a creative thesis. Even before that, though, I acted and wrote plays and sketches in high school. And I guess before that, I was just a general goofball. My "start" is hard to pinpoint, I think!

So how did you get to where you are today? Do you think it was talent, being at the right place at the right time, where you went to school, a combination, or something else entirely?

It's always a mixture. For me, the progress I've made comes from having some natural ability and a family that encouraged me to explore it, then going to a college where I had a ton of opportunity to get onstage (on campus and in/around Boston), then moving to a place where I could apply that practice where there were more opportunities.

Do you think “funny” can be taught and/or learned?

I think it's like any skill/talent combination. Everyone has a different ceiling on how funny they can be, but it can only be maximized through practice and hard work. Not everyone can be Chris Rock in the same way that not everyone can be Michael Jordan. Or, I guess, in my case, not everyone can make the starting lineup for the Stoneham High School JV basketball team, sophomore year. I am one of those have-nots.

What is the biggest mistake you’ve made in your career and how did you bounce back from it?

Hmm. I'd like to think that I didn't make any huge mistakes, but we all like to imagine that our paths led us to where we are now, so they were right and valuable. (I read that somewhere. I am not smart enough to have made it up.) The thing I'd change, if I had to do it again, is that I'd spend more time post-college writing scripts and essays and submitting them places. I was really keyed in on standup, which I love (and am happy I worked hard at), but I neglected to cultivate those other skills until I moved from Boston to New York. Granted, I was busy teaching preschool and tutoring and doing shows and trying to see my friends, but I could have used that time better. I really dove into other forms of writing when I came here.

Being in the entertainment scene in New York, you have probably met some famous people. Which comedian(s) have you met that left you absolutely starstruck?

There was a period in early 2012 when I met Dave Chappelle, Robin Williams, and Dane Cook in the span of about a month, and that was pretty exciting. All three were under kind of cool circumstances where I didn't have to be a weird fanboy about it. I was still pretty flustered. Robin Williams was just like: "Hi, I'm Robin." And I had to struggle not to say: "Yeah. OF COURSE YOU ARE."

What is the most annoying question you get from people? 

"Are you going to tell us a joke?" Almost exclusively delivered by the boyfriends of female friends.

Want more Gondelman? You can find Josh on Twitter & check out his website for upcoming shows and news. He most recently co-wrote You Blew It!: An Awkward Look at the Many Ways in Which You've Already Ruined Your Life with Joe Berkowitz, and the book is available for pre-order on Amazon.