The Best Pitch of All Time

Welcome to 2023.

Big dreams, bold predictions, and good intentions reign at the beginning of every year.

So before we begin I want to share two quick quotes to help you through this year.

1. "What we appreciate, appreciates."

As you march forward in 2023, don't forget to celebrate the wins. A founder and friend told me this back in the beginning of 2021 and it's helped me in the toughest times.

2. "You'll be amazed but not surprised."

Ever wondered why all those fitness programs have people take pictures on day 1 and again on day 90? It's because we forget how much progress we make unless we can look back at something tangible.

This is my quote as I always tell any founder I coach or work with to expect this. Amazed because of how far they go, but not surprised because they put in the work.

Let's get to it.

-Robbie

DEEP DIVE: Don Draper: Pitch Master

If you know anything about me, you know I’m obsessed with the greats. Tom Brady, Amanda Gorman, Michael Jordan, Martin Luther King, Steve Jobs, Serena Williams...The list goes on and on.

I love learning about what makes them tick and then applying those concepts to my own life.

And since a lot of my work involves perfecting pitches, I of course have a favorite sales pitch—one that I think is perfect in every way.

It might surprise you, though, to learn that my favorite sales pitch of all time isn’t even real. It’s from Mad Men, a fictional TV show about an advertising firm in the 1960s.

I know that sounds crazy, but I don’t think so. We can learn a lot from art because it shines a light on humanity in a way that real events sometimes can’t. We’re provoked to action by the heroism of Iron Man in the Avengers movies or motivated by the discipline and grit of Rocky Balboa. My favorite show, The West Wing, shaped the way I show up in the professional world more than anything I learned from a law professor or mentor.

It may sound crazy but The West Wing played a critical role in a closing argument I gave to save a man wrongfully accused of murder.

With that in mind, what follows is a breakdown of my favorite sales pitch. I’ll explain why what Don Draper does is so effective and how you can apply those concepts to your own pitches in real life.

You may already be a Mad Men fan and remember the scene that I’m talking about, but for an optimal experience, it’s probably best for you to watch the scene first here:

Mad Men: The Carousel Pitch

The Challenge

Don Draper is tasked with creating an ad campaign for a new piece of technology Kodak has developed—what we know as a carousel slide projector. The Kodak execs insist they want to focus on how innovative and technologically sophisticated the product is. They also want Don to work the product’s name “The Wheel” into the pitch.

Don, of course, is dubious.

The Hook

Don starts his pitch by doing two things. One, he establishes his superiority to other agencies by showing (not telling) his unique approach. Two, he frames his mission—for customers to form a deep bond with the product.

I say showing and not telling because Don conveys this information through an anecdote about a former co-worker. He transforms this co-worker into a character by giving just enough detail that his audience can picture him: a Greek named Teddy who wrote ad copy for a fur company.

It’s such a clever way to begin because you can’t even tell if the pitch has started.

Don now has the room’s undivided attention.

The Emotion

Don then continues with something that’s powerful. He taps into emotion to keep bringing the audience closer. He does this both by showing personal photos of himself and his family and through his word choice. It’s a brilliant choice because it appeals to both your visual and auditory senses at the same time.

The visuals enhance Don’s emotional connection with his audience because they convey vulnerability. He shows slides of intimate moments with his family. The slides portray him as a caring, family man with strong values—which, if you’ve ever seen the show, is pretty ironic. The old adage about a picture being worth a thousand words rings true here. There are no charts or graphs in this presentation. Instead, Don found a way to use visuals in a way that captured his audience’s emotional brain.

Likewise, his word choice throughout the pitch is incredible. Just look at these two sentences:

“In Greek, nostalgia literally means the pain from an old wound. It’s a twinge in your heart far more powerful than memory alone.”

See the way those strong words evoke emotion? Nostalgia, pain, wound, twinge, heart, powerful. The audience has already forgotten the product because Don’s not selling the product. He’s selling a feeling.

Also pay attention to his non-verbal cues. Look at the way he carries himself and his delivery. His flow is controlled. He lets words sit with you. You can feel the emotion oozing out of every word he says.

By the end of the pitch, it’s clear Don is FEELING the nostalgia himself. Look at the glint of tears in his eyes.

And notice the power this emotion has over his audience. One colleague is so overcome with feelings, he rushes out of the room crying.

It’s good to remember this simple fact: People make decisions based on emotion, and they justify with logic. If you want people to do what you want them to do—whether that’s buy your product, work with you, or invest in your company—you have to speak to their emotional brain and THEN speak to the logical, rational brain to justify it.

The Risk

The big problem Don’s facing with this pitch is that Kodak has made clear recommendations about what they want. They want to focus on the technology aspects of the product, and they also want to call it “The Wheel.” Don knows those are the wrong choices, but he has to present alternatives in a way that doesn’t feel threatening.

Now that he has his audience emotionally on the hook, he’s ready to introduce his strategy. He does this by reframing.

“This device isn’t a spaceship,” he says, alluding to Kodak’s desire to boast about this fresh new technology (remember this is set in the 60s during the infancy of the space program). “It’s a time machine.”

By reframing through metaphor—the space ship, the time machine—Don subconsciously shifts his audience’s expectation about the ad strategy from one of innovation to one of nostalgia and emotion.

He then lays on the emotion—”it takes us to a place where we ache to go again”—before dropping the hammer and taking the biggest risk of his presentation.

“It’s not called the Wheel” flies directly in the face of what his client was asking for! But because of the way he approaches it, it doesn’t feel confrontational or insubordinate.

It’s also softened by the way Don follows this sentence—the offering of a BETTER name and concept that jibes with the tenor of his pitch. He does this deftly in the same sentence.

He follows it up with a knockout punch full of emotion-laced rhetoric:

“It lets us travel the way a child travels, round and around, and back home again. To a place where we know that we’re loved.”

Mic drop.

His audience is so compelled, they’ve totally forgotten their preferred pitch angle. Don has successfully reframed the client’s request.

The only way you can get someone to agree that the different choice is the right one is to frame it the right way. You do this by pulling the right levers at the right time—analogy, rhetoric, anecdote, delivery.

The way you show up and the choices you make allow you to position yourself the way you want to. You own the room, the way Don did in this scene.

This pitch may be fiction, but you can learn a lot from it.

Implement these lessons, and you can take any audience on a ride to any place you want.

RESOURCES for Founders and Storytellers

What else can you learn from Don Draper? This ScreenRant article pulls out 10 solid lessons for both business and life.

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In terms of trends for 2023, many investors believe that under-represented founders will secure more funding. Here's hoping this plays out. This Tech Crunch article explains why,

FINALLY...

The Live Story Redesign was a massive hit. It's something we are exploring to run as a semi-regular event.

If you'd like to stay up to date and you didn't attend the last one, shoot us an email and we will add you to that mailing list.

Now let's go crush 2023.

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