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Angie McMahon of Wisecrackin: “Fight for your idea”

I had an idea to do an interactive online show. I was trying to pitch it to different clients but no one really understood what I was getting at. So after a few months of trying to pitch it around I just said F it, I am just going to do it and maybe then […]

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I had an idea to do an interactive online show. I was trying to pitch it to different clients but no one really understood what I was getting at. So after a few months of trying to pitch it around I just said F it, I am just going to do it and maybe then I can have something to show clients about how it works. The big problem is Zoom comedy shows are mostly terrible. We all felt it very quickly. You are telling jokes to a quiet room while a side chat that has nothing to do with you scrolls along side your face. People staring at you from there desks sipping drinks. It is just such a hard sell. We ALL want to go to a club again and have that in person experience. We all miss it. So I thought what if I could make a show that was still showing comedians skills (joke writing) and spontaneous (live) and interactive for the audience (audience challenges in the chat) so that everyone is protected in their own space but still very much so connected. So that is why I came up with the show Wisecrackin. Comedians are pitted in a head to head competition to write a punchline to a set up they have never seen. The audience votes live on their favorite and play along in the chat.


The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Angie McMahon, Executive Producer and Host of the weekly livestreaming Comedy Game Show “Wisecrackin”. She is also a faculty member at The Second City in Chicago where she teaches sketch comedy writing, stand up, and storytelling. She currently resides in Chicago with her husband and two daughters.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in the suburbs of Chicago. I thought when I was a kid I wanted to be on Broadway. I was in a competitive dance troupe that toured and taught dance till I was in my mid 20’s. The big problem with my Broadway dreams was I can’t sing a lick. So I kept being cast in the non singing “funny” roles. This eventually turned me completely toward comedy. After graduating Columbia College Chicago I went on to train at The Second City (where I work today). I do a lot of Freelance writing for clients who are usually looking to inject humor into their brand. So I make a lot of tweet, social media posts, and sometimes scripts for short sketches.

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

The glass is not half empty or half full. It is refillable.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

ANYTHING written by David Sedaris. I devour his books. I guess because they are so funny and so personal. I always feel like I am sitting down with an old friend chatting over coffee. AND the first hit play I ever directed (actually it was the FIRST play I ever directed and it just happened to become a hit) was “The Book of Liz” by David and Amy Sedaris. That was a huge turning point in my career and when people started really taking notice of my directing.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

In 2017, I sold my Comedy Theater out of financial distress. All I had ever done in my adult life is work in store front Theater in Chicago. So it was a big change for me to step out of those roles. I stayed artistically fulfilled helping my students do shows. While I worked on my freelance work. So I was a remote worker when this all happened. I was performing very infrequently, I wasn’t really seeking out opportunities unless they came to me.

What did you do to pivot as a result of the Pandemic?

I had an idea to do an interactive online show. I was trying to pitch it to different clients but no one really understood what I was getting at. So after a few months of trying to pitch it around I just said F it, I am just going to do it and maybe then I can have something to show clients about how it works. The big problem is Zoom comedy shows are mostly terrible. We all felt it very quickly. You are telling jokes to a quiet room while a side chat that has nothing to do with you scrolls along side your face. People staring at you from there desks sipping drinks. It is just such a hard sell. We ALL want to go to a club again and have that in person experience. We all miss it. So I thought what if I could make a show that was still showing comedians skills (joke writing) and spontaneous (live) and interactive for the audience (audience challenges in the chat) so that everyone is protected in their own space but still very much so connected. So that is why I came up with the show Wisecrackin. Comedians are pitted in a head to head competition to write a punchline to a set up they have never seen. The audience votes live on their favorite and play along in the chat.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

I was doing virtual Easter with my family and my baby sister told me about Quiplash by Jackbox Games. It is a fill in the blank game. I shared my screen and we all played over Zoom. The kids could play (unlike Trivia they don’t know) so everyone can get involved. It was such fun, AND they have a feature where you can write your own show (customize it) that was the aha moment.

How are things going with this new initiative?

Slow. But good. People who see the show say really nice things. But getting people use to a new kind of entertainment is tricky. There is a lot of education that has to come with it. It is a show you watch on your computer (like youtube) but also you play along with your phone (that can feel intimidating to people who are not super comfortable with technology. Plus we want you to chat with us as part of the show. So the audience is very involved.

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?

This show happens every week because of the cast and writers. We have 22 writers that write us a brand new show every week. We have a cast of about 15 people that rotate in the show every week. Every single one of them is a GD saint. I am so lucky to have crossed paths with any of them.

Can you share the most interesting story that happened to you since you started in this new direction?

I guess the biggest arch if you will has been with Jay Mohr. I somehow tricked him (not really tricked but almost felt like it) to be on the show. He ended up leaving half way through because he was confused and frustrated and it was causing panic. We talked again and he agreed to do the show again the following week. I was so overly worried about what happened that I came on VERY strong with email and texts trying to set him up for a good experience. Anyway he ended up not doing the second show and we haven’t talked since. It bothers me the way it ended and I wish I could change it or move past it. I am sure I will. But it became this huge lesson of trying to work with celebrities. They have to do a rehearsal. Hands down, I can never have ANYONE on the show again without a 10 min tech rehearsal. So I learned that lesson. Also it is so hard to balance being excited to do a show with a celebrity and being an overwhelming fan. I am a medium talent at best so I have only really done shows with any type of celebrity maybe a dozen times. But I am always awkward around them. I am sure it has to do with imposter syndrome. Anyway it was crazy cool fun and also really upsetting all at the same time. And now my kids know who Jay Mohr is. So I guess that is something.

What are your “5 things I wish someone told me before I started leading my organization” and why. Please share a story or example for each.

  1. Fight for your idea. Don’t let someone mess with your idea before it is even tried.
  2. Try other peoples ideas. Really give it your all to see if it will work before you give up on it or dismiss it.
  3. Let your friends fail. Don’t try to fix everything. People learn more from failing them from succeeding.
  4. Fail, let yourself mourn your frailer, then move on. Give yourself time to be upset. It is ok. But after that time is up don’t look back.
  5. You are using Twitter wrong. It can actually be a very joyful fun place if you go seeking that. But if you just want to get on and fight about clash of ideas you will find it to be a terrible place to hang out.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

I want to stay informed. So at lunch I give myself 20 min to look at the news and feel whatever I am going to feel about it. Then once after dinner. But I can’t do more than that. It really effects my mood if I do. I try to also take a lot of breaks and check on everyone in the house to make sure they are supported in what they need for a successful day.

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?

In 2010 Jon Stewart put on a Rally to Restore Sanity (I happened to organize the Chicago satellite rally with no connection to the Washington Rally). He had a wonderful quote that stuck with me and drove me during that time. “We can agree to disagree without calling each other Hitler”. That has become my mission statement for life.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

I guess besides Jay Mohr (really to get closure on that whole thing) I would love to sit down with Ken Griffin (owner of Citidel investments) my husbands boss. Just to pick his brain. My husband wont’ even let me entertain the idea.

How can our readers follow you online?

Twitter.com/angiemcmahon

Twitter.com/Wisecrackin

Wisecrackin.com

Thank you so much for sharing these important insights. We wish you continued success and good health!


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