I had never heard of comedian Aaron Karo until recently, which surprised me considering he is all over the place and has a massive following. Karo isn’t your typical stand-up. He is a forward thinking-business man-author-hard core bachelor-stand-up. He can literally thank the internet for much of his success. The road that led him to become an author and comedian started with an e-mail he sent as a freshmen in college to a group of friends back home about college life, which spawned into a regular e-mail column that spawned his career. He has never looked back, never stopped partying, and never stopped writing. He has published three books and created the popular site Ruminations.com. His first stand-up special is airing on Comedy Central Friday, November. 19th. Karo chatted with SO about his career, his comedic style, his stand-up special, and even his cure for hangovers.

Serial Optimist: Hey Aaron, thanks for taking the time. How are you? What kind of mood are you in as you respond to this interview?

Aaron Karo: Well, I enjoy talking about myself, so that’s good. But I’m sober, so that’s bad. I guess we broke even.

SO: You are a stand-up comedian and author. You founded a user generated website. You have made what you could call a franchise off of Ruminations. And this all started by you sending out a funny email as a freshman in college?

Aaron: That is correct. I sent the first “Ruminations” email from my dorm room at the University of Pennsylvania in September 1997. That set off a series of events that led to me being able to spend the majority of my adult life without wearing pants.

SO: When did you decide stand-up was something you wanted to pursue? Did you have to teach yourself how to be funny on stage? What was the transition like from basically writing funny things and not having to perform them, then writing funny things and having to perform them live as a stand-up?

Aaron: I had been writing since 1997 but didn’t start doing stand-up until 2002. My transition was aided in part by naïveté. I didn’t really know what you were and weren’t supposed to do on stage so I just took ideas I had written and expanded them into longer stories. And that worked for me. The best part about performing vs. writing is that you get instant feedback…and it’s easier to meet groupies.

SO: What would you say your brand of comedy is, or your style of comedy?

Aaron: Fast-paced anecdotes about drinking, dating, and fornicating.

SO: What exactly is Ruminations.com? Where did the concept/idea come from, and is it doing as well as you imagined? Are users as active as you hoped? More active? What kind of response are you getting?

Aaron: Ruminations.com was inspired by the fact that my fans were always responding to my column my writing their own observations and sending them to me. So I decided to create a site where they could share them with the world. The site is basically Digg meets Twitter meets Seinfeld. People write original jokes within a certain character limit and the community votes the best ones to the top. The response has been ridiculous. People love it. Fans have met on the site and hooked up (we call it “rumi-dating”). There’s even a Ruminations Fantasy League. It’s bananas.

SO: Does your material, or way of thinking, change at all as you begin your thirties? Or is it all still the same, and age is just a number?

Aaron: It’s constantly evolving. Five years ago, none of my friends were married. Now they all are. And babies are on the way. Plenty more to riff on.

SO: How much do you, on a daily basis, live the life that you portray through your books and comedy? I guess my question is: how much of your act is an act?

Aaron: Everything I talk about actually happened. There’s a track on my last album entitled “PukeBerry” about how I got drunk, vomited on my BlackBerry, and attempted to call T-Mobile for support. True story. In the special and on the album there’s an anecdote about me trying to take a chick home from a bar in Tokyo and trying to explain the definition of “one-night stand” because she didn’t speak English. Fact.

SO: Will there be a Ruminations on Thirtysomething Life book? Do you feel pressure to stay single and live the crazy life so you can keep making material?

Aaron: My third book, I’m Having More Fun Than You, is probably as close as I’ll come to Ruminations on Thirtysomething Life. But I don’t feel any pressure to live a crazy life. The stories come to me, I don’t come to them.

SO: Tell us about your Comedy Central stand-up special, The Rest is History, which premieres on 11/19. How pumped are you for this? Will this be your first major TV special? Where was it shot?

Aaron: The special was shot at the Wilbur Theatre in Boston. The first thing I do is shout out the Yankees and then I get drowned out in boos, which was awesome. It is my first TV special and I’m super pumped. The title The Rest Is History comes from the phrase that all bridesmaids use at the end of their awful toasts. The bulk of the show is about dating and relationships and how a lot of my friends’ marriages began with a random drunken blow job. The finale is what a bridesmaid speech would sound like if she actually told the truth.

SO: Is the Comedy Central special what people will find on your new album by the same name, or was that recorded somewhere else? Where can people find the new album?

Aaron: The album was filmed simultaneously, but the awesome part about it is that it’s uncut and uncensored. So while the special will have bleeps and will be cut down for commercials, the album is about twenty minutes longer and full of F-bombs. You can actually download the full audio or the full video – at iTunes, Amazon, or anywhere that sells digital music. I’ll also link them all at TheResIsHistory.com. The album is being released by New Wave Dynamics on 11/20 the day after the special airs.

SO: What current comedians are you in to; who are you a fan of?

Aaron: I am and will always be a Chris Rock groupie. No one does it better. Chris, if you’re reading this, call me!

SO: What’s the best cure for a hangover?

Aaron: I have a reputation for going out after my shows and getting drunk with my fans. The only trick I’ve found to avoid a hangover is to never go to sleep. So I’ll go out all night, get back to my hotel, shower, pack, head to the airport, and by the time I get on the plane I’m not drunk anymore, so I pass out then wake up sans hangover. I should patent that.

SO: In one sentence, sum up why people should watch your comedy central special, and why people should know who Aaron Karo is. Don’t worry; it can be a run on sentence.

Aaron: Since most of my fans are female I will direct this to them: if you want to find out what is going on inside the typical male mind, be sure to tune in. It’s terrifying.

SO: It really is terrifying. Thanks Aaron!

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SO Note: Make sure to watch Karo’s Comedy Central special, The Rest Is History, Friday, November 19th at 11pm, and look for the uncut/uncensored album and video that will be released digitally on November 20th through New Wave Dynamics on iTunes. For more information go to his website, www.aaronkaro.com, and follow him on Twitter @aaronkaro.