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Here’s what the worst day in my professional life taught me about business

When I first founded Knuckleball Comedy in 2016 we started by only running after-school improv comedy classes for kids. We still run those after-school classes, though now it’s only a tiny part of the business. But back then I didn’t run our corporate team building or professional development workshops. And I didn’t know logistically how to work with kids during the school day. So all we had were these after-school classes.


We began with one after-school program and then quickly grew to 15, then 20. We were doing good work but it wasn’t quite enough to run a really robust business because we were only providing programming from 3pm-5pm on school days and that was it. Before developing our in-school residencies for kids and our team building workshops for companies, I had one other idea of how to have more business going during the day.


And boy let me tell you, it was a terrible one.


I thought to myself, you know who is free from 8am-3pm with nothing to do? Really old people. So I developed a curriculum that I thought would work to provide fun, unique and valuable programs to senior citizens at senior centers and assisted living facilities.

(Two Knuckleball Comedy performers performing at an assisted living facility in Chicago in 2017)


I got my grandparents and some of their friends to help me make a promotional video. Somewhere in the deep depths of youtube I’m sure it can still be found. I wrote some marketing material and created another website page for it. And then I put my sales hat on and started calling senior centers and assisted living facilities to try to sell them my improv comedy program specifically built for the elderly.


I received some bites and we began running a few programs, a few times a week at a few different facilities during the 8am-3pm time period. No one was under the age of 85 at any of those programs. And I would say they went as well as anybody could have expected an improv comedy class to go with a group of 85-100 year olds.


When you work with a group of kids, it’s hard because they just can’t sit down. When you work with the elderly, it’s hard because they just can’t stand up. I joke but it’s oh so very true on both accounts.


Those programs went fairly well and they invited us to come back, which we did for a while. Though I laugh now at how little we were getting paid for those classes compared to what I now know we need to make in order to have a thriving business.


But after we booked some of these daytime classes, we then moved on to providing evening entertainment. And let me tell ya, in the “programs for the elderly” world, running a daytime class is Rookie Ball and doing the evening entertainment is the Big Leagues.


The daytime class might have had at most 10 people. The evening entertainment might have been the entire home with 75-100 audience members. It was the next level.


So I booked a few of these evening entertainment performances and I brought along another performer, who also happened to be one of my best friends, Sean, to perform along with me. We were excited and nervous though we really didn’t know what we were walking into.


I actually remember speaking with the directors of the senior homes as I pitched them and told them why their residents would love our performances. I remember them all saying that they’d never had any type of comedy performance before - usually just solo musicians. And then I would confidently say, “Oh well I know they’ll love us! You won’t be able to wait to have us back!”


Everyone has to do something for the first time otherwise you’ll never do it. No one wants to be the first person to do business with a company, but somebody has to be the first and as a business owner, in order to get your business off the ground, you have to be so confident that they can’t believe just how confident you are. And that’s exactly how confident I was.


The first performance we did was aggressively mediocre. We did have a little bit of audience participation and I remember we actually got some smiles and laughs when we sang some improvised songs. All in all it seemed like it was worth trying to do again and see if we could learn and improve.


Then came the second performance. While I was hoping for learning and improving, I forgot about the option of crashing and burning. The first bad decision I made, which might be the decision I regret most in life, is that I invited my grandparents to come and watch. The facility we were performing in was near their house, and I thought to myself, what would my grandparents enjoy more than watching their grandson on-stage performing? On this particular occasion, the answer was just about anything else.


The room we were in had about 40 chairs in it and there was a small stage area, but not an actual elevated surface. As the room filled up and we were about ready to begin, we ran into our first hiccup.


Just as we were about to introduce ourselves, a nurse walked in while rolling a resident in a hospital bed hooked up to some type of breathing apparatus. There was no room in the audience to put the bed so she rolled the bed onto our stage. We went from having an already tight 15-foot long stage to a 5-foot long stage. Not to mention the breathing apparatus was so loud that it really seemed like every breath this woman took might be her last.


Our two-person improv comedy show had suddenly turned into a three-person show. For the remainder of this story, let’s refer to this bed-ridden woman as Dianne.


We began by each telling a little joke. I know exactly the joke I told and I stand by it’s hilarity. I told the joke well and I emphasized the punchline with a huge smile on my face, and the crowd went from silent to deadly silent. And in a room full of people in their 90s, you really never know. After I told the joke the only person I knew for sure was still alive was Dianne because I could hear every breath she took.


When the joke fell flat I whispered to Sean and Dianne, “this could be a long night.” At least I was right about something.


After our jokes, we then began our first improv performance game. I acted as the host and Sean sat in a chair and created a fun character. The game is I try to get the audience to ask Sean questions and his character answers in ways that become increasingly more entertaining and hopefully increasingly more hilarious.


So I began coaxing the audience into asking questions so Sean could answer. I gave examples, I had a lot of energy, I began calling on people. Nothing. No one said anything. Finally, after seemingly an eternity, a woman in the second row raised her hand. I think I speak for Sean and Dianne when I say we were all thrilled to see that hand go up.


So I called on her. And then she delivered the line that now I’ll never stop laughing about. With a frown on her face she asked pointedly, “When is this going to get funny?” I laughed inside and then looked at Sean and he said so everyone could hear, “hopefully soon!”


It did not.


After that debacle, we only had a mere 55 minutes left in our hour long performance. At the time I thought surely that was the low point of the night. But unfortunately for Sean, Dianne and myself, it wasn’t. The next 55 minutes were a blur to me, I don’t think it became worse than the beginning but I know for sure it didn’t get any better.


In most ways it wasn’t a big deal. Comedians bomb. Even your favorite comedian bombed plenty before they became famous. It’s part of the process. It’s not fun but ask anyone, it happens. Even at the time, I would have embraced this absolute bomb and laughed it all off. But unfortunately, my grandparents were there. So I had to live with having my grandparents see the worst day of my professional life.


But wait, it still gets a little bit worse.


We finished up and began packing our things, I didn’t want to stay a second longer than we had to. I didn’t even want to say goodbye to my grandparents. I actually wanted to pretend like I didn’t have any grandparents. I wanted to pretend that I was raised by wolves which explains why I thought it would be a good idea to do an improv comedy show at an assisted living facility.


Just as we headed for the door, one of the women who had just been chatting with some others came up to us with a smile on her face. Given the smile on her face we were all hoping she’d say something nice. She did not. She said, “I was just chatting with some of my friends and we all have something to say to you.” I politely said ok. And then she said with a huge evil grin on her face, “Don’t quit your day job!”


Now it was one thing to say this to me. But to wrap Sean and Dianne in this? I think that was too far.


Plus, the joke is on her. This is my day job! It was my day job then and it still is now. And since then we at Knuckleball Comedy have made over 25,000 people laugh in our kids shows and corporate team building workshops and our corporate entertainment options. And we don’t plan on stopping anytime soon.


Sean and I said goodbye to Dianne and ran out of there and went to a bar where we laughed and laughed and laughed about it. About five years later and we still love laughing about it.


Running a business is a journey with good ideas if you’re lucky and always some bad ones. But it’s always a learning experience. It’s safe to say you won’t find any Knuckleball Comedy programming at any nearby assisted living facilities.


I’ll never forget that day even when one day I’m in the audience for one of those. It was just one tiny blip in the Knuckleball Comedy journey. As an entrepreneur you have to try things and that sometimes means failure. This is still my day job and I am happy to say Knuckleball Comedy is doing better than ever.


If you’d like us to come make you laugh at an event where the majority of the crowd is under 85, contact us HERE.


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