Podcast Summary

Podcast: The Dave Gerhardt Show
Episode: The Day You Become a Better Storyteller with Harry Dry (Founder of Marketing Examples)
Date: November 13, 2025
Host: Dave Gerhardt
Guest: Harry Dry

Episode Overview

This episode, recorded live at the DRIVE 2025 Exit 5 event in Burlington, Vermont, features Harry Dry—recognized marketer, copywriter, and founder of the renowned Marketing Examples website and newsletter. Harry delivers a dynamic, idea-packed talk on what separates forgettable companies from unforgettable ones: compelling, conflict-driven storytelling. He shares practical frameworks, real-world examples, and tactical exercises designed to make any marketer smarter and more formidable as a storyteller.

Key Discussion Points & Insights

1. Why Storytelling in Marketing Matters

• Harry kicks off with an unexpected deep-dive into the history of the can, illustrating the point: world-changing products are forgotten without a good story.
  • Notable quote:
    “If you can't wrap it in a compelling narrative, nobody will give a shit. People think they make decisions on facts, they don't. They're just responding to the shape of a story.” (06:04)
• Core lesson:
  • Facts don’t move people—stories with tension and conflict do.

2. The B2B Marketing Example: Asana vs. Basecamp

• Comparison between Asana and Basecamp: Asana spends an immense budget on unfocused messaging. Basecamp, run by storytellers Jason Fried and David Heinemeier Hansson, grows through compelling narrative and bestselling books.
  • Notable quote:
    “You want to grow twice as fast, you’ve got two choices. Throw money like Asana or learn how to tell a story.” (10:18)
• Takeaway: Narrative trumps budget for memorable B2B marketing.

3. Story Construction: It’s All About Conflict

• The Foundation:
  • Every story is built on conflict. Without tension, there’s no story.
  • Exercise: Harry invites the audience to inject conflict into bland headlines (“The cat sat on the mat” → “The dog wanted the mat too”).
  • “Conflict is the foundation. Nearly all writing could benefit from more conflict.” (12:30)
• Examples:
  • ‘Steal Like an Artist’ sells more than other creativity books because it contains inherent conflict.
  • Successful YouTube titles (Usain Bolt vs. a cheetah) vs. generic ones.

4. ABC: The Three Types of Enemies in Storytelling

• A - Direct Competitors:
  • Your brand vs. others (e.g., Stoli vs. American vodkas).
• B - Competing Approaches:
  • Your method vs. alternatives (e.g., Tube vs. Taxi, Loom vs. Meetings/Email).
• C - Beliefs:
  • Stand against prevailing beliefs that your product refutes (e.g., “Marketers shouldn’t learn writing”).
  • “Your positioning is ‘we do X.’ Your story is ‘why we do X.’ Story is conflict. There are three enemies: competitors, approaches, or beliefs.” (22:48)
• Key question: “What are we actually competing against?” (attribution to April Dunford)

5. Story vs. Positioning vs. Storytelling

• Positioning: What you do (“We do X”).
• Story: Why you do it (“We do X because…”; your narrative tension).
• Storytelling: The myriad ways you inject your story into customer minds—ads, homepage, sales pitches, content.
  • Basecamp example: “Slack is a day long meeting with no agenda.”
  • “Find your company’s version of six pack abs, and you tell the story over and over from different angles.” (26:10, paraphrasing Andy Raskin)

6. Five Laws of Storytelling

1. No Conflict, No Story
2. No People, No Story
   • People care about people, not generic abstractions. Example: Real employee ‘Calvin’ at Ramp makes the tech story human.
3. No ‘Buts’ and ‘Sos,’ No Story
   • Drive narrative forward with implicit “but” and “so” transitions, not endless “and...and...” lists.
4. No Ordinary, No Story
   • Make small things feel big with detail and specificity (cost of a $5 coffee can be more compelling than billions saved).
5. If You Start Explaining, No Story
   • Don’t explain concepts—show with examples.
   • Quote: “Spare me the explanation, give me an example. Backspace your explanation and write an example instead.” (29:50)

7. Know Your Category—The Heart of Storytelling

• Substance beats technique:
  • The best storyteller is the one who knows the problem-space deeply.
  • “If you want to get better at storytelling, stop reading books. Write one.” (36:50)
  • All the storytelling frameworks in the world won’t help if you don’t have insight and lived experience.

Timestamped Memorable Quotes & Moments

• Why stories trump facts:
  • Harry: “People think they make decisions on facts. They don’t. It’s the shape of a story.” (06:03)
• Story is conflict:
  • Harry: “Nearly all writing could benefit from more conflict.” (12:30)
• Tension creates attention:
  • “You only need one thing—conflict. That’s why ‘Steal Like An Artist’ is a best-seller and ‘Make Brilliant Work’ is not.” (14:30)
• On people in stories:
  • “Stories are about people. If you want attention, talk about real people.” (19:09)
• On company knowledge:
  • “You want to tell a good story? You want to have a story to tell. Know more about the problem in your category than anyone else.” (36:55)

Audience Q&A Highlights

Q1: Can marketers force better storytelling inside dull companies?

• Harry: “You gotta take matters into your own hands. Do the work, send it straight to the CEO. If they keep saying no, maybe find another job.” (40:17)

Q2: How do you push leadership to embrace storytelling early?

• Harry: “Start with the sales deck. Any company doing sales has to explain why pick them over alternatives. Story lives there already.” (44:12)
• Dave: “Show them 10 great companies and ask—did any win without a good story?” (44:30)

Q3: How do you protect good copy from dying by committee?

• Harry: “Take matters into your own hands. Be too good to be ignored. At Ramp, the idea is yours—the buck stops with you.” (45:04)

Q4: On the “but/so” structure—should you use these words in copy?

• Harry: “It’s implicit, not explicit. Not ‘but’ between every line, but the forward momentum should be there.” (46:36)

Q5: How does AI fit into storytelling?

• Harry: “AI gives you ideas, but it lacks conviction. The best use—have it flag cliches, but real courage still comes from you.” (47:25)

Q6: What makes Ramp special?

• Harry: “They are persistent and act fast—find the right people and empower them. They care, and every employee has equity.” (50:01)

Practical Takeaways & Frameworks

• ABC Conflict Sources: Approaches, Beliefs, Competitors—create tension in your messaging by choosing an enemy in one of these buckets.
• The “But/So” Test:
  • When editing your narrative, check: do transitions have conflict or are they just “and…and…and…”?
• Make it Human:
  • Where possible, tell a story about individuals, not abstractions or technology alone.
• Start Small:
  • Use specific, relatable, everyday examples (e.g., the $5 coffee expense) to make big impacts.
• Substance Over Form:
  • Deeply understand your industry’s problem; the stories will follow.

Closing Advice

• Harry: “Forget arcs and whatnot. Just know your shit. … Know your problem space so well that you could write a book on it.”
• Harry: “If you can’t wrap it in a compelling narrative, nobody cares.”

For Listeners

If you work in marketing—especially B2B—implement these storytelling methods to make your product and company memorable. Create conflict, know your true competition, use specific examples, and, above all, understand your market better than anyone.

Notable Quotes (by Timestamp & Speaker)

• (06:04, Harry Dry): “If you can’t wrap it in a compelling narrative, nobody will give a shit. People think they make decisions on facts, they don’t. They’re just responding to the shape of a story.”
• (10:18, Harry Dry): “You want to grow twice as fast, you’ve got two choices. We throw money like Asana or we learn how to tell a story.”
• (14:30, Harry Dry): “‘Steal Like An Artist’ is the only best-seller here—it has conflict. ‘How to Be an Artist’ doesn’t.”
• (19:09, Harry Dry): “Stories are about people. If you want attention, talk about real people.”
• (29:50, Harry Dry): “Spare me the explanation, give me an example. Backspace your explanation and write an example instead.”
• (36:50, Harry Dry): “If you want to get better at storytelling, stop reading books. Write one.”
• (40:17, Harry Dry): “You gotta take matters into your own hands. Do the work... If they keep saying no, maybe get another job.”
• (45:04, Harry Dry): “Be too good to be ignored. ... The idea is yours. No one’s going to fuck with it. If it goes wrong, the buck does stop with you.”
• (47:25, Harry Dry): “AI is good at identifying cliche copy, but it won’t have conviction for you.”
• (50:01, Harry Dry): “At Ramp, they act fast. The story: find the right person, empower them, care about outcomes, and move.”

[End of Summary]