Looking for Sales Pitches in all the Weird Places

Robert Lucas
7 min readNov 15, 2019


Photo by Jonathan J. Castellon on Unsplash

I have a friend named Kevin.

Well, his real name isn’t Kevin, but that’s what I’m calling him in this article to respect his privacy.

Recently, Kevin saw a beautiful girl while walking out of a bar. But he didn’t say anything to her. He got in his car and drove off.

But halfway around the block, he said:

“I kinda wish I would have gotten her number.”

So Kevin pulled a boss move.

He drove back to the bar, parked, walked in and said something like:

“Hey this is really random, but I’m on my way out and I just thought you were beautiful. So I wanted to meet you and see if I could get your number and maybe we could hang out sometime?”

And wouldn’t you know it…

It worked!

But it wasn’t all sunshine and roses…

Unfortunately, this girl (we’ll call her Emily) ghosted my friend after one text. (If you’re not single in 2019, you should know that “ghosting” basically means not responding to someone who has either texted or called you.)

But there was an even bigger problem:

Emily was only in town for the week. So if this date was going to happen —

It needed to happen soon.

So what did Kevin do?

A lot of guys would try to play it cool in this situation.

Act like they weren’t that interested anyway and move on.

But Kevin is more honest (and dramatic) than that. He doesn’t have a big ego. He’s not afraid of putting himself out there. And he really wanted to get to know Emily better.

So he decided to go for the Hail Mary touchdown pass…

He sent her a 3-minute long voice memo making the case for why they should go out before she left town.

As he was telling me about it last night, I realized something:

Holy sh*t. That’s actually an incredible sales pitch.

I pointed out some of the copywriting tactics he used in his voice memo, and he said something like:

“Wow. I didn’t even know I was doing that!”

So, because I think this is a fantastic story — and a fantastic example of salesmanship — I’m going to break down his message from a copywriting perspective.

Here we go…

(Some quotes have been edited for clarity + simplicity + confidentiality.)

The Lead

“Emily, what’s up? It’s Kevin — the random dude from the bar on Monday night.

I normally would not be double-texting somebody, but this isn’t exactly my normal scenario.”

This is so simple and so effective.

Kevin is acknowledging that this is a bit of an awkward situation. What’s important to note is that, during the voice memo, he’s kind of laughing at himself as he says the first line.

By acknowledging that this is a weird situation and having the sense of humor to laugh about it, Kevin is showing that, although he might be a random dude from the bar…

He’s socially aware and isn’t afraid to poke a bit of fun at himself. He’s likable and trustworthy.

Beyond that, he says that he “normally would not be double-texting somebody, but this isn’t exactly [his] normal scenario.”

This is subtle, but important. It shows two things:

  1. He’s not desperate. He “gets it.” He doesn’t normally badger people to hang out with him. This makes him trustworthy. Nobody wants to buy anything from an overly pushy or aggressive salesman.
  2. This situation is different than what he’s used to. He’s willing to go out on a limb to spend some time with Emily. We’re all more likely to trust someone if we know that they’re over-extending themselves — even a little bit — for us. We all just want to feel special — both as partners and customers.

The “Reason Why”

“I thought about calling, but that seemed psycho and texting just seems fake…so I figured I would send a voice memo and throw out a couple options…”

When someone does something out-of-the-ordinary, we want to know why they’re doing it.

For example, if you see that a company is offering you 90% off their most expensive product, your “bullshit detector” will probably go off loud and clear until the company explains why they’re giving you such a crazy discount.

This situation is similar.

Kevin is self-aware enough to know that sending a 3-minute-long voice memo to a random girl you’ve only talked to for 30 seconds is a bit out-of-the-ordinary.

So, he’s acknowledging that and providing a clear reason why he’s doing it.

Beyond that, he highlights why the other options weren’t valid and helps her arrive at the same conclusion he did…

In this scenario, sending a voice memo was the best option.

This is important in sales copy too.

If you’re offering your customer something unique or just doing something out-of-the-ordinary, you need to be very clear about why you’re doing it.

Future Pacing/Risk Reversal

(This one is a doozy, but it’s worth it, so stay with me.)

“Option one: You get on that plane this weekend and fly back to Vermont and we don’t hang out. You go back to your life ‘as is.’

And, you know, maybe in the back of both of our minds, we always wonder:

‘Huh, what could have been? What could have happened if I would have met up with that random person that I met at the bar?’

Option two would be meeting me for coffee either tomorrow morning or Friday morning.

And, worst case scenario:

You have a good story to go home with about how you met up with this random guy who walked out of the bar…

Literally got in his car and was ready to go…

And then came back in because he knew that he wanted to ask you out and learn about who you are.

And you get a free cup of coffee to get your day started.

Best case scenario:

Things go well. We enjoy each other’s company, and who knows?

Call me crazy. But maybe in like a year or so, we find ourselves on some cool trip halfway around the globe or something.

And we’re super glad we got coffee with that random stranger that we met in the bar for a little bit.”

In this part, Kevin plays out the two possible ways this thing could go.

They either get coffee together or they don’t.

If they don’t — they’re risking missing out on a potentially amazing relationship.

If they do — they could fall in love and take a trip around the world.

Yes, it’s dramatic. And yes, it’s a long shot. But that’s a genuine picture of Kevin. The dude believes that anything is possible, and he’s not afraid to say it.

And, regardless, in the worst case scenario, Emily will get some free coffee and end up with a good story.

There’s pretty much no risk in saying “yes” to this date.

With any decision, there are multiple ways the situation could play out. This is true in purchasing decisions as well.

If you’re trying to sell someone on an idea, a product, or even a date —

You’ll need to make them feel comfortable first and prove that there’s no risk involved.

The Close

“So yeah. The ball is totally in your court. Let me know which one of those options you want to roll with…

You’re probably now wondering if I’m either a complete psychopath or maybe you find it endearing and sweet and a little different. Obviously, I’m hoping for the latter of those.”

One of the biggest things to take away from this is the importance of Know, Like, and Trust.

If you listen to the audio recording of this (I can’t share it, because Kevin said he would kill me in my sleep if I did. Sorry.), you’ll notice that Kevin is halfway laughing at himself through part of it.

He recognizes he’s being over-the-top.

He knows it’s a bit dramatic.

And he clearly acknowledges that it’s not normal behavior.

It’s endearing AF.

Emily might not know Kevin (yet), but she’s on the way to liking him and trusting him because he has shown that he’s socially aware and trustworthy.

Finally, he lets her know that the decision is up to her. He’s provided some clear options, and it’s her move now.

It’s a call-to-action.

It’s marketing 101. You have to be clear about what the next step is for people and let them know when it’s their turn to make a decision.

The Offer

This is subtle, but important:

Kevin is NOT inviting Emily over to watch Netflix in his basement.

He’s inviting her to coffee…in a public place…in the morning.

This goes a long way to show that he’s trustworthy and really does have good intentions in meeting her. Had he invited her over to spend the night, this would be a much different conversation.

Just something to keep in mind.

Your offer has a lot to do with the way you present your sales pitch.

The Results


Emily leaves town tomorrow. But her and Kevin are planning to get drinks tonight.

Best of luck, you lovebirds.

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