What I Learned From Giving MY Pitch 100+ Times in 2 Hours

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Earlier this week RajNATION Innovation exhibited as a finalist for the Chicago Redeye’s Big Idea Awards.

Hundreds attended to interact with 15 other finalists and myself.

Each finalist had a folding table and tablecloth to work with, the rest was up to us…

My Big Idea stemmed from the approach I take to working with startups.

In case you’re unclear, RajNATION Innovation helps startups not suck at telling their story so they can pitch and raise capital.

A big reason the RajNATION process is different from anything else is we leverage my 12+ years experience as a rapper (aka wordsmith), blending performance and entertainment principles with branding to create pitches that sing.

So, what was my Big Idea? “Raise UP!” — The first ever rap album about startup life and raising capital. Think Schoolhouse Rock meets startups.

Over the course of about 2 hours, I delivered the RajNATION Innovation & Raise UP! elevator pitches over 100 times. Here’s what I learned.


1. Ask permission to give your spiel.

It seems obvious at an event where people have literally paid to see you that they should know you’ll launch into your pitch right away, and the reality is most people do expect that. But early in the evening I noticed a stark difference in the nature of the interaction when someone approached my booth and I first asked, “Can I give you my spiel?” as opposed to just diving right in.

Here’s why this works: If you dive in without permission, the listener doesn’t realize until a few lines in that you’re trying to explain your business. They poke around at what they see on the table, and then when they see you’re talking about something specific, they realize you’re pitching, and actually start paying attention.

If you get permission first, you lock in their full attention.

And because they granted that permission, they take on an extra responsibility themselves to lean in and listen.


2. Know what you’re saying, every single time.

You 100% HAVE to have your ‘spiel’ — your pitch — locked down pat.

You have under a minute (on the high end) to get your point across. You can’t waste any of that time thinking about what you want to say. You have to go in knowing exactly what you’re going to say every single time.

When you know what you’re saying, your confidence is at its highest and your energy is infectious. When people see that you’re excited, they WANT to approach you, and that gives you even more energy.

Of the 100+ people I pitched to, only one person said, “wait, I’m confused,” and that was more because of a language barrier than anything else.

Don’t worry about looking or sounding stupid for saying the same thing over and over again.

There were many instances where I delivered a pitch to one person, then a few more people walked up and I gave them the exact same pitch while the original person was still there.

It’s not weird to keep saying the same thing.

The audience knows it’s what you’re there for, and if anything hearing it again will make it stick in their brain.

In contrast, if you say something different every time, or are caught up not knowing what to say, you send mixed messages to your audience and fall out of favor because they perceive you don’t know what you’re doing.

(Pro tip: You can preserve your voice by speaking to groups of people at once. You can multiply your reach by asking individuals if they came with any friends/colleagues, and if so, ask the individual to bring them over — they are usually hovering somewhere nearby.)


3. It’s YOUR job to get people to your table.

I often hear exhibitors at events complain that no one will come up and talk to them.

Just because you showed up, doesn’t mean they have to engage with you — Yes, even if the point of the event is for them to engage with you. The audience is not obligated to go up to every single person.

That’s why it’s on YOU to do whatever you need to draw attention in a non-threatening way.

Call them in.

Whenever someone hovered within 10 feet of my booth and/or made eye contact with me, I immediately shouted, “Hi! How are you?! Can I give you my spiel?” (See Takeaway #1).

Be the friendly face that engages with them, and you’ll draw them in.

If that makes you uncomfortable, then make a joke out of it. Act like you’re a carnival game person and shout to them, “Hurry, hurry, step right up!” It takes the pressure off you, and they’ll smile or laugh, which breaks down any tension.


Unfortunately I did not win my category, but I knew going in I was at a disadvantage having just a concept as opposed to an actual product.

I was able to validate the concept, however, by having two demo tracks on display for listening.

With that said, I would like to share with you here one of those tracks. I give you, ‘Wake Up, Raise Up’. In this song, I rap from a woman’s perspective about the frustration of being a female entrepreneur trying to raise money in a man’s world.

Enjoy, and share with your fellow founders if you like it.

If you want updates on album progress, and want to learn how to make YOUR pitch a head-turner, join the RajNATION Innovation email tribe using the subscribe button below.

Caroline Pestel