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Stand and Deliver

Careers

This article originally appeared in the Bentley Magazine.

Stand and Deliver

The Seriously Funny Madison Malloy '05

As a student, Madison Malloy ’05 dreamed of a job on Wall Street. Two years as an analyst in residential mortgage-backed securities and a stint as a partner in an e-commerce company convinced her otherwise. In 2009 she made a radical shift, built on her lifelong love of telling jokes. Today, the Denver native is a comedian, actress, producer and writer.

Funny to the bone.

Comedy is one of those things: You’re either born with it or you’re not. I’ve been telling my jokes my whole life. I always wanted to gather people around to tell jokes. Even at Bentley, when Wall Street was my dream, I had the greatest jokes. We’d be sitting in one of the apartments, and I’d be telling jokes. But being at Bentley and being business-minded, no one thought of it as a career.

Career path, with detours.

I really had that entrepreneurial spirit my whole life. So I left Wall Street when I had the opportunity to run a B-to-B e-commerce website. I was 24 at the time. Around the same time, my dad and I had a conversation. I thought at that point I had screwed up my life. My dad said the biggest mistake people make in their life is to chase the money and not chase the passion. He asked what I would want to do [if money didn’t matter] and I said I’d go around the world and tell jokes. He said, “That’s a professional comedian.”

Starting out.

I first went into comedy part time. I wanted to try it out, so I did it at night. You don’t get paid when you start out. You start with open mics and you have “bringer” shows, where you bring your friends and you get stage time. You just keep meeting people, networking, writing and working on your craft. Then you get booked on shows; you start headlining.

Business of comedy.

A business magazine once wrote a story saying if you want to run a successful business, go talk to a comedian. Their product is the joke. If the joke doesn’t work, they go back to the drawing board and they alter it until it works. I have focus groups every night. I’m in front of live audiences testing this material.

Point of view.

When you start, you go to that shock value. Then you evolve. You start writing stuff that’s true to you. You have to find your POV, your point of view, and until you do, you don’t have your voice in the comedy world. But once you find that POV, your character becomes developed. Now someone can be sitting in the audience and they can say, “I get this guy, this is what he’s thinking. I know his life through his comedy.”

Material matters.

I write about things I find funny, whether it’s my family, dating, certain fears, etc. If I think it’s funny, I talk about it.

Show time.

You’re always nervous: You don’t know how you’re going to do. But I have found that how I feel on the inside directly impacts how I do in that show. If I’m feeling insecure or negative, if I’m having a bad day, I’ll have a bad show. When you’re feeling positive, the audience can sense it. When I’m just having fun, they are going to have fun. They’re going to get to know you.

Fearless marketing.

Marketing for me is about social media, being funny, getting out to do shows as much as possible. I’m on stage four, five, six times a week — sometimes not that many nights, but I’ll do two or three shows a night. You have to be consistently creative and coming up with new material. You have to be constantly thinking and seeing the funny in things. Marketing is just putting yourself out there, and being vulnerable. This goes to any business you’re doing, whether you want to be the senior vice present of a bank or running the next big computer company. You have to be vulnerable and unafraid. Fear is what holds everyone back from doing what they want.

Discipline at work.

I’m going to meetings, talking to producers, I’m writing, I do consulting gigs. Yesterday I was a character on one of my friend’s Comedy Central shows. I’ve been on Sirius XM and Fox News; I’ve performed at rock concerts and other big festivals. I’ve had really cool opportunities. But work is a discipline. It’s a discipline to keep going after you’ve been told “no” a hundred-plus times. There have been so many times I wanted to quit. But if I did, I’d regret it. Knowing that is what keeps me going.

Serious advantage.

One advantage I have compared to most is the business background. If I didn’t have my Bentley experience, I would not be able to write the movie [I’m working on], find the person to budget the movie, come up with a more strategic way to get these big projects done, and be in on the ground floor. Without it, I would not be able to understand the producing side — the budget and the finances and the equity of the film versus what goes to the investors and to the creators and the producer pool, and how to divvy that up. Otherwise, I would just be a person saying, “Put me in a movie, listen to my jokes!”

But this is a business, and I need to accomplish X, Y and Z to reach my goals. At the end of the day, I’m a business person. I’m just running a very different business. I’m running my LLC.

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