Comedian & Author Jessica Delfino: This idea creates empires, improves the world and millions of lives a day; It brings smiles to children’s faces, it educates those in need, it creates award-winning 
By: Alexandra Spirer
Tags: Comedian, Entrepreneur, Authors

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I started working in comedy when I met a comedian in the park near my college. I stupidly went back to his house with him to “watch comedy videos”, but his story checked out. He actually had comedy videos, we actually watched them, and I became hooked on the idea of being a comedian. Writing is an intrinsic part of creating comedy, and I like being able to use that muscle in a variety of different formats, whether it’s on the stage, on paper or in a grocery store parking lot when the moment requires me to spit out a smart-mouthed comment at a well-deserving stranger.

Can you share the most interesting story that happened to you since you began leading your career?

One cold, rainy weekday evening, I traipsed through the Lower East Side in New York City at an odd hour to yet another comedy show in another drafty basement. I’d almost called to cancel, because it was such a lousy night, but my dedication to performing drove me to put on pants and get out the door. When I arrived, I was disappointed to see no more than five shadowy figures in the audience. I did my set to the best of my ability anyway. Upon getting off the stage, I made my way out to where the people were sitting and was surprised and delighted to see the “five shadowy figures” were Dave Chappelle, The Beastie Boys and Morgan Spurlock. Dave Chappelle put me in the Chappelle show pilot, and Moran hired me to write for his TV show on MTV and other projects over the years. It was good that I’d put on my pants and gotten out to the show! I have a million stories like this one.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I still remember awkwardly approaching a big deal industry rep who was flirting with a male comedian outside of a comedy club. I handed her my card, and she took it like I’d just handed her a dirty diaper. I was mortified.

What do you think makes your company stand out? Can you share a story?

When I was in my early 20s just starting performing in NYC, I was writing material that I’d describe as a cross between Liz Phair and Joni Mitchell, with a little 2 Live Crew mixed in. I wrote jokes and funny songs that were about bold, mostly female-oriented themes. When I was doing that, there were few other people who did it. Now there are millions of these kinds of songs online and out in the world, but I guess you could call me a pioneer of the vagina song. I am also probably one of a small club of comedians to be denounced by the US Catholic League over my material.

Are you working on any exciting new projects now? How do you think that will help people?

I just wrote a book called Dumb Jokes for Smart Folks. It features wordplay, puns and jokes and takes a stab at being a “mom jokes” book. It was a #1 bestseller on Amazon. I think it will help people laugh and have a happy minute in the middle of their day. It will also help moms reclaim the idea that only dads can tell dumb jokes!

What advice would you give to others following your path to help them thrive?

Be nice to everyone you meet. Don’t try to judge if someone can help you or not, or reserve good treatment for only certain people in your business. It doesn’t matter. Just treat everyone with kindness and respect. Always. Even if you have to be frank with someone or set boundaries, do it with respect. That, and send everyone a holiday card, even if it’s a digital card. Don’t let people forget about you!

What advice would you give to other female comedic writers about the best way to manage their own careers?

We all have teams, and teams are important. No one is an island. Look around your world of family and friends and see who could be a member of your team. Who is a law student or lawyer who might advise you within your budget or barter? Who is an accountant who helps your parents or someone you know in your same line of work? Partner with others to stay on top of your accountability or to write material or trade ideas. Join writing groups. In addition to writing, set aside time to do work that benefits your personal goals every day. Build your team of trustworthy people and treat them with respect and kindness. Pay good attention to your health, and call the people you love often. Keep learning. Don’t date other comedians!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am very grateful to so many people. I could literally write a list of 10,000 people who have helped me along the way. Once when I was very young, I didn’t have much money, so I hitchhiked to Montreal to go to perform at the Montreal Comedy Festival. I got picked up in Vermont by a guy who seemed a little sketchy, but I really wanted to get to the festival, and I was cutting it close on when I needed to arrive. He drove me to the border of Canada, and stopped the car. “I can’t take you any further,” he said. “I have a warrant out for my arrest.” He then handed me $50 and said, “Good luck to you.” I asked him to give me his address so I could pay him back someday, and he refused. As he drove away, I realized he was a ghost. JUST KIDDING! He was a real person — a kind stranger who helped me out when I was desperate, broke and young. I have A MILLION stories like this.

How have you used your success to bring goodness to the world?

I don’t know. I like to think that I’ve inspired people, that I’ve inspired laughter and happiness in people, that I’ve brought honor, joy and pride to my family, that I’ve been a good friend, sister, mother, wife, daughter and neighbor. I regularly contribute to charities and all that kind of stuff, but I also love to build community in any and all ways that I can. I do this by offering whatever I can to people who need it, be it information, an ear, friendship, support, advice or even just a phone call to say hi. I strive to be a positive force in the world, and doing what I love enables me to be able to do that with more gusto.

What are your “5 Leadership or influential Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

I have learned that every person is valuable in your life. Even the ones who might seem lousy offer lessons to be learned. Treat all people the same. Give more than you get. You won’t always get what you give back, and it doesn’t matter.

I have learned that leaders build people up, they don’t break or tear them down.

I have learned to study what my strengths and weaknesses are, and to use each when it is appropriate. I have loads of weaknesses that actually make pretty sweet tools, when need be. For example, I apparently do a bad job when I change the cat litter box, hence, my husband usually does it.

I have learned that networking is not what people think it is. People think that networking is meeting people who are more powerful for you who can do you favors. But that’s not what it is. Networking is meeting people who at your stage in your industry and working together to lift each other up as you all grow in your careers.

I have learned that life is short, and most of the little things really don’t matter. Focusing on the bigger things will bring the most joy: goals and dreams, family, health. Floss regularly. Moisturize. Eat more vegetables than cookies, drink more water than beer.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I often spend time thinking about how I can help others, and then trying to implement those ideas. I think that is the best thing I can do. It is something that anyone can do, no matter their level in life, age or what abilities they have or don’t have. This idea creates empires, improves the world and millions of lives a day. It brings smiles to children’s faces, it educates those in need, it creates award-winning entertainment and beyond. Anyone can think, “Who can I help? How can I help them?”, and then implement the ideas they unearth. It’s an easy thing to do. The rewards of helping others are real. Not only does this please and honor the community and the helper, but helping others can become addictive and can replace other, more negative addictions. Every time we help someone else, we get a dopamine rush. It’s as good as drugs, baby — not that I’d know! J It’s even better, because instead of breaking down the world around us, it builds up everything around us.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I really love Mae West’s “Those who are shocked easily should be shocked more often.” It’s easy to look at this in a negative light, but I see it like, people live in shells. It’s beneficial to look out of that shell once in a while and read something challenging. Grow. It’s beneficial to be less shockable, by knowing and learning more about the world around us. It doesn’t mean I go out seeking things to be shocked by, or that I spend time doing things that are harmful to my psyche. But education is a wonderful thing. Books are truly magical. I also like “a rising tide floats all boats”.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’d like to reconnect with an old friend, Nick Kroll. I lost touch with him years ago and I think of him fondly. Plus, he owes me $5.

How can our readers connect with you on social media?

I’m at @JessicaDelfino on Instagram and Twitter and @JustSomeMom on TikTok.