Why I Make Fun of My Life When I Pitch

by Scott - 5 Comments

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Every time I’m pitching someone, I always try to make fun of my life in some way. In fact, I intentionally seek out opportunities to do this.

Larry David

A lot of business development and sales is about likability. Given two equal products, buyers will purchase from the seller they like more. Hence, by making myself more likable, I increase my odds of succeeding.

There are many components to likability; some which we can control, others that we can’t (like being 6’4, tan, and really, really ridiculously good-looking – crap). One aspect of likability we can control is how relatable we are.

How Being Relatable Enhances Likability

People like people that they can identify with. There’s an inherent sense of understanding injected into an interaction when you connect on something. That’s why it engenders intimacy. Common things new acquaintances can relate on include:

  • Mutual friends: “You know Jen? Holy cannoli!”
  • Shared experiences: “You went to Bemidji State too? NO, WAY.”
  • Geographic familiarity: “ I spent a fortnight in Albania last year! Crazy that you lived there.”

Speaking about these topics can be effective ways to be more relatable, and I employ all of them.

One thing far less people intentionally try to establish a connection around are the funny quirks and dispositions in our lives. We all have them, yet for one reason or another, we rarely talk about them – especially with new acquaintances!

Because it’s so infrequent that these instances are brought up, establishing a connection around them can be incredibly powerful. Scarcity = amplified results.

I’ve found one the most powerful ways to catapult my relatability, and thus likability, is to make fun of the dispositions in my life.

Let’s say I’m pitching someone on a restaurant web-site builder. Here is an example of how I’d weave making fun of my life into a pitch:

It’s so important for restaurants to have a website because people make dining decisions online.

I always look online to decide where I’m going to eat. I try not to do it at work anymore though. After the 13th time I encountered a flash website that blasted something akin to “Everybody Dance Now” when I opened it, I decided I should probably stop doing that. I’m pretty sure the guy who sits across from me thinks I’m going to a Salt ‘N’ Pepa concert this weekend.

In this example, I’m pointing to a funny disposition in my life that I hope the person on the other end can relate to. The ideal outcome is to prompt a response along the lines of “OMG I thought I was the only person that happened to.” The feeling that we’re connecting on something unique strengthens the bond.

Beyond relatability, poking fun at my life signals a few other things that contribute to likability:


By making fun of myself, I’m making myself vulnerable. This signals to that person that I feel comfortable enough with them to subject myself to risk. +1 intimacy, likability


I’m projecting that I’m confident and comfortable with myself when I make fun of my life. Confidence balanced with humility is a very attractive combination. +1 likability

Appeal to Humanism

Even when someone can’t relate to a funny personal anecdote, they can relate to similar dispositions they face in their lives and the fact that they’re not perfect. Conveying that you’re human and not perfect puts people at ease. +1 likability 

No One is perfect

Poking fun of yourself can be used to engender intimacy in any situation. I just wanted to highlight the effectiveness within the professional context because I haven’t seen many people that have pitched me recently employ it.

As a BD or sales professional, the product and ecosystem which you sell in is often out of your control. However, your ability to be likeable and build a relationship so that you give yourself the best chance of winning a deal is. Optimizing on relatability by doing things like poking fun of yourself is one way to do this…especially if people in your family wear green tube socks and short-shorts when doing yard work like mine : ) Love you Pops


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