Selling is an art, it’s not necessarily about the product, it’s about the trust you build. Doesn’t matter if you’re selling shoes to a Cutco sales rep or lollipops to a nun, we live in an era where any solution you provide there are at least a hundred similar.
How Comedy Helped Me Hit My Sales Quota

Back in 2015, I worked for a tech company and every day for two straight weeks, I remember banging my head on my desk. At the end of each work day, I would see my name at the bottom of the sales leader board highlighted in red. It was the type of red that created internal panic, that type of color that caused you to accidentally do the harlem shake when you saw it.

Each color had a significance, it felt as if they all had some type of individual achievement attached:


Lesson #1: Work Smart, Not Hard

To this day the color red triggers me the same way all words trigger the politically correct, “hey you can’t say bald, it discriminates those without hair!”

I feel like a war veteran constantly having flashbacks anytime a car backfires. Similarly, every time I see the color red, I have the urge to start cold calling. For weeks I would go home feeling anxious and stressed as the sense of job security started to slowly fade away.

I tried everything I could to increase my sales. For example:

  • I would meet with all the top sales reps and shadow them
  • I would reach out to top sales reps on LinkedIn and bombard them with questions
  • I would study my game tapes (recording from sales calls) and look over the playbook (sales script) constantly.

After all this work, I was still in the red. It was a glaring sign of complete failure.


Lesson #2:The Path To Success Is Through Failure

About 3 years ago was the first time I stepped on stage, I initially did it to impress my date. I was told by many co-workers and friends that girls like funny guys. So I figured if I can show this girl I am funny during a comedy show, she would surely fall in love with me. Fortunately, much like the audience’s enjoyment, she never showed up.

At the time it felt like one of the most traumatic experiences in my life. It was like watching a one year old learning to walk for the first time, constant attempts at trying to be funny just to wind up falling to the ground.

The worst part was staring out at the audience’s blank faces, I never felt more demoralized in my life. Like the moment you realized Santa isn’t real, after you baked him cookies and sat out all night waiting for him.


After recovering from my full blown panic attack, my friend from Rutgers called me. His call was to teach me to “...never not believe in yourself.” That with enough drive, conviction and focus you can accomplish anything...literally anything. Although he was at risk of failing out of school, this man “... finally ate 6 big greasy fat sandwiches in 35 minutes.” 35 minutes! That’s about 1,500 calories per sandwich, roughly 15 Big Macs. He should legally be a vegetable right now, but after “4 years of practicing...” he accomplished one of his dreams.

His determination was inspiring, not Tiger Woods winning the 2008 US Open or Planet Earth II: Iguana vs Snakes video inspiring. But watching your little brother parallel park for the first time after months of failure inspiring. Sure he had some dents and scratches, but he did it. So with that news, I decided to continue down this journey of comedy, mainly for the girls.

Lesson #3: Be clear in your message

After months and months of bombing*, I started to notice a slight parallel between the way people behaved to my comedy and the way people reacted to my pitch, utter confusion. No one knew what I was talking about my message was not clear.

As I continued through this journey, more and more patterns started to emerge. I felt like Sherlock Holmes trying to connect the dots. I started to notice that sales and comedy are very similar, they both work if the target audience trusts you. In comedy, the audience trusts that you will be entertaining them, in sales it’s the trust you have a concrete solution to their problems.

Week after week went by with slow progress, I started to see small improvements with both with my comedy and my pitch. Still no one was budging, in 5 months I accounted for 0 laughs and 0 sales, but I started to celebrate the minor victories. Finally 6 months later, I got my first laugh. Not from an audience member, but from the whole crowd. It was the single, greatest moment in my life, also the moment that turned my life around. The crowd’s laughter can only be described as getting a hug from your constantly disappointed dad for a job well done.


Lesson #4: Be relatable

What I had said wasn’t ground breaking, but it was authentic, relatable and most importantly honest. This was the key I had been missing in my comedy. As I saw the light at the end of the tunnel I started to follow suit, I kept talking about things that related to me in my life and bringing that to the stage. As I continued to open my world audiences became more receptive. I felt as if my life was coming together, although I still had 0 sales I had a notion that will soon change.

On June 22nd, 2016, I saw a commercial for viagra. As I watched the commercial I realized it made no sense at all, for example why is there a need to end the commercial with two separate bathtubs. Anyway, I got so excited I decided to create an entire set based on the idea of selling.

Basically, I broke down three types of commercials and spoke about what they are selling and the ways to sell it. After this breakdown, I decided in the mist of the performance to sell my own product, a pill to help with Gastrointestinal disorder, I called it GIDDI (Gastrointestinal Disorder During Intercourse).


Lesson #5: People love the funny guy

As the show came to a close, I was at the bar ordering pineapple juice. There was a tap on the back of my shoulder, three audience members came to me not only to tell me how amazing my set was, but to let me know if that product ever exists they would purchase it for family members. In the midst of thanking them, another audience member barged into the conversation spewing the same rhetoric about my set. “Oh my god! That was hilarious! Just fantastic! I think I should buy my boyfriend this pill he definitely suffers from something like this. Please let me know when you have created it!”

In that exact moment as I sipped my pineapple juice, I realized people actually felt a connection to this pill, this made-up pill. This pill was essentially a solution for their needs, whether you had a flatulent boyfriend or a gag gift for your family. The way I presented the pill gave everyone with enough information and a sense of familiarity that they convinced themselves this pill is worth having.

I sat in silence, trying to comprehend everything that transpired. And just like that I was hit with a stroke of genius, I recognized that I needed to use comedy to sell. I noticed when people laugh, they begin to feel comfortable which is the foundation for trust. Also I noticed, people are able to digest information better when humor is involved.


Lesson #6: Learn to read your audience

I took this ideology and applied it to my sales calls. At first I would make minor jokes with the small business owners, then I started to share with them funny stories. Finally I would tailor each call to the prospective client I was speaking with so the jokes did not feel generic, yet more personalized. Slowly as I kept working on building the rapport, I noticed I became a natural with selling. Within the month I went from 0 sales to hitting my quota month after month.

I learned that the way information is presented makes a huge difference. That people not only cared about what you were saying, but how you said that information. They wanted to purchase something from someone they felt had their best interest at heart and was fun to talk to, someone that makes them feel better. Once I showed them who I really was they began to trust my judgement and the rest was history.

  • Bomb




Posted by Rishi Mathur
Rishi Mathur
Rishi Mathur is the Content Producer for LeadIQ and is one of the most important voices for this generation. Rishi has on many occasions been compared to the likes of Aziz Ansari and Gandhi based solely on his looks. He has helped with the growth of several different startups and has experience in both marketing and sales. He has been published in many major media outlets such as TealMango,, The Oregonian, and Highland Park Planet. He is a champion at building communities and would love to start his own cult worshipping the different cuisines around the world.

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