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exitfive Newsletter #199

Why I Love Marketing (Exit Five Newsletter)

November 20, 2025
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Hello and welcome to the Exit Five Weekly Newsletter — read by 42,000 B2B marketing professionals around the world. Exit Five is a membership site designed to help you build a successful career in B2B marketing. Join 5,700 other members at exitfive.com.

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TOGETHER WITH QUALIFIED

⁉️ Agentic Marketing: What is it and should you have it in your marketing strategy?

TLDR Plaid Case Study

Agentic Marketing isn’t just another AI trend, it’s how smart B2B teams are actually using AI inside their GTM.

Think AI agents running campaign orchestration, lead routing, sales handoffs, and never taking a day off. (Seriously.)

If you missed the live event, you can now watch the full recording of the Agentic Marketing Summit. Top CMOs and this year’s “30 Agentic Marketers to Watch” break down exactly how agentic marketing works in practice. What’s hype, what’s real, and what they wish they knew before they started.

You’ll see how real teams are using AI to drive pipeline and how to plug it into your own GTM.

The Day You Become a Better Storyteller (Thanks to Harry Dry)

Harry Dry

Editor's Note: Hey. It’s Dave again. One of the sessions I was most excited about at Drive (our annual event in Vermont) was Harry Dry's talk on storytelling. Harry runs Marketing Examples, writes for 150,000 marketers, and is one of the best copywriters on the planet. After years of being internet friends (it really does go down in the DMs) this was the first time we'd ever met in person and he didn’t disappoint. He showed up with a story about Napoleon, canned food, and why most marketing misses the point entirely. In fact - one of our members, Drew, came up to me at lunch and said “Harry Dry reminded me why I loved marketing” and man that made my YEAR. That is what we’re all about. Beyond B2B marketing, we all loved marketing first - who cares that it happens to be B2B. So today’s newsletter is focused on lessons from Harry. Enjoy.

“Does anybody know who invented the can?"

Not the most obvious way to start a marketing talk…

But within 5 minutes, Harry had the room hooked.

The can changed everything. It was the invention that made Arctic exploration, World War II, and space travel possible.

But nobody makes movies about it.

Why? Because the can itself isn't interesting. What's interesting is the human drama around it.

The struggle. The stakes. The people who made it matter.

Your marketing works the same way.

👥 Your Product Isn't the Story. The People Are.

The mistake most marketers make is thinking the product is the hero. It's not. Your customer is the hero. Your product is the thing that helps them win.

Most B2B marketing sounds like this…

Example 1

It's not bad. But it's not memorable. Here’s how Harry changed that:

Example 2

The post absolutely blew up. The difference? Making the customer the hero. Not the product.

✏️ Write to One Person, Not a Committee

The best marketing sounds like one person talking to another person. Not a brand addressing "users" or "decision-makers."

Example 3

That's storytelling. That's conflict. That's a real person talking.

When you write, picture someone specific. What keeps them up at night? What makes them feel stupid at work? What would make them look like a genius to their boss?

Then write to that person.

🔒 Conflict Is What Makes People Care

Which book do you think outsold all the others combined?

Example 4

Answer: "Steal Like an Artist."

Why? It's the only one with conflict. Artists shouldn't steal. They're supposed to be original, honorable. But here's a book telling you to steal. That tension makes you want to know more.

We're suckers for conflict.

Think about every story you've ever cared about. There's a problem. Someone's struggling. The outcome matters.

Your marketing should work the same way. Show the pain. Make it specific. Make it real.

🚫 If You're Using "And," You Don't Have a Story

The writers of South Park had a really simple rule.

When you put your story together, if the word "and" connects all the sentences, you don’t have a story. You have a shopping list.

What should connect your sentences? "But" and "so."

"I came to Burlington, but I nearly missed my flight, so I dashed through Terminal 6."

That creates momentum. That creates tension.

"But" and "so" drive the story forward. They create the constant tension that keeps you hooked.

Most marketing is just "and." We do this, and we do that, and we also do this other thing.

That's not a story. That's a list of features.

🤌 Start Small, Not Big

It's easier to make small feel big than the other way around.

Companies love to brag. At Ramp, everyone wanted to talk about the billions of hours they save. Impressive, but it doesn't connect.

Instead, Harry suggested starting with something ordinary: a cup of coffee.

How much does coffee cost? $5.

Every employee at your company will expense a cup of coffee at some point. You think it costs $5.

But here's the real cost: Employee uploads and tags the expense (3 minutes). Manager stops what they're doing to approve it (1 minute). Finance hunts for the expense (4 minutes). Double checks it (1 minute). Matches the receipt. Finally reconciles everything.

The real cost of that cup of coffee? Three employees. Four interruptions. Thirty minutes.

That's so much more impactful than bragging about billions of hours saved.

👀 Stop Explaining. Show Me Instead.

If you start explaining, you don't have a story.

Every time you're about to explain something, backspace it and write an example instead.

Take the bench scene from Good Will Hunting. Robin Williams could have said: "Love is an active commitment. It's the choice to value someone else's wellbeing as much as your own."

That's an explanation. But this is what he actually said…

"You wouldn't know about sleeping sitting up in a hospital room for two months because the doctors could see in your eyes that visiting hours don't apply."

That's an example. That's a story. That hits different.

🔎 Steal Good Ideas (And Know Where to Find Them)

Harry's newsletter goes to 150,000 people. You know how he comes up with ideas?

He collects everything. Ads he likes. Headlines that work. Stories that stick.

He has a swipe file. Not of templates, of moments. Of things that made him feel something.

When he sits down to write, he doesn't start from scratch. He pulls from what's worked before and makes it his own.

The absolute best marketers are curators. They notice what works, they see the pattern, then they make it their own.

🫵 What This Means for You

You don't need to be a professional copywriter to tell better stories.

You just need to stop writing like a company and start writing like a human.

Find the conflict in what you do. Make your customer the hero. Use "but" and "so" instead of "and." Start with something small and ordinary instead of bragging about billions. Show examples instead of explaining concepts.

Pick one thing from this to try this week. Rewrite a homepage headline to add conflict. Turn a feature list into a story with "but" and "so." Take your biggest number and make it small and relatable.

You already have the raw material. Customer problems. Real people on your team. Specific moments that show what your product does.

Now, you just have to tell it like a story.

– Dave

P.S. The thing that hit me most about Harry? He wasn't teaching theory. Every single point came with a real example which is exactly what he was telling us to do in our own marketing. He practices what he preaches which I love about him. So the real challenge now: how can you apply this to your B2B business? It’s not easy. We tried to do some of this on the spot with exercises from Harry at Drive. But it’s this type of thing that I want to leave you with. Great marketing is everywhere, you just need to know where to look - and then how to apply it back to B2B.

I am editing today’s newsletter from the couch, because I’m laid up. Things were going too well and I finally had to deal with a setback. I’ve been putting off this surgery for a bit, but last week I went in to get my hip fixed and I’m down for the count for the next 8-12 weeks after successful surgery to fix femoroacetabular impingement and labral tear in my right hip. I’m happy, healthy, and this is just because I have been pounding on that hip for so many years! But a setback nonetheless, and a good test of my mental fortitude right now - it’s very hard for me to sit and do…nothing. But that is what I must do. I asked Lya to take this picture for our newsletter - THOUGHT LEADER DOWN!

Dave Down

P.P.S. Send me lots of replies this week, I need them.

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📚 LATEST CONTENT

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✍️ NEW FROM EXIT FIVE

Do you need to learn more about AI in Marketing?

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Our head of marketing, Jess, just launched a new newsletter devoted entirely to AI. She’s sharing what she’s doing running marketing here and also talking about everything she’s learning about AI, new tools, workflows you can steal, etc.

Click here to subscribe to The Prompt and we can help you get an A in AI. 🍎

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