The Day You Become a Better Storyteller with Harry Dry (Founder of Marketing Examples)
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
Harry Dry, creator of Marketing Examples and copywriting expert, delivers a masterclass on storytelling fundamentals for B2B marketers at Drive 2025. (05:27) Through engaging examples ranging from Napoleon's invention of the can to modern B2B companies like Asana and Basecamp, Harry demonstrates how positioning differs from storytelling and why conflict is the foundation of every compelling narrative. (08:27) He breaks down his "five immutable laws" of storytelling while emphasizing that the secret to great marketing stories isn't technique—it's knowing more about your industry's problems than anyone else.
• Main Theme: The critical difference between positioning ("we do X") and storytelling ("why we do X") in B2B marketing, with conflict as the essential ingredient that makes any story compelling and memorable.Speakers
Harry Dry
Harry Dry is the creator of Marketing Examples, a popular newsletter that reaches 150,000 marketers, and has built one of the most comprehensive marketing swipe files available online. He's recognized as one of the best copywriters on the internet and works as an advisor with companies like Ramp, where he's created viral LinkedIn campaigns that have generated millions of views.
Dave Gerhardt
Dave Gerhardt is the founder of Exit Five, a private community for B2B marketers, and co-author of "Conversational Marketing." He hosts the Exit Five podcast and organizes the annual Drive conference for B2B marketers in Vermont.
Key Takeaways
Story is Conflict - The Foundation of All Compelling Narratives
Harry emphasizes that every great story requires unresolved tension that gets resolved. (11:38) He demonstrates this through book titles, showing how "Steal Like an Artist" outsold eight other creativity books combined because it was the only title with inherent conflict. The exercise of rewriting "The cat sat on the mat" to "The cat sat on the dog's mat" illustrates how introducing opposing forces immediately makes content more engaging. This applies directly to B2B marketing - instead of saying "move work forward," create tension between the current broken state and your solution.
Know Your Problem Better Than Anyone in Your Category
The most crucial advice Harry offers is becoming obsessively knowledgeable about your industry's core problems. (34:02) When he met a billionaire who claimed to "know more about the problem with the education system in America than anybody in America," Harry realized this depth of understanding is what enables great storytelling. Companies like Basecamp excel at storytelling because they've written over 100 essays on project management problems. The test: you should know so much about your category that you could write a book about it.
Positioning vs Story vs Storytelling Framework
Harry provides a clear framework: Positioning is "we do X," Story is "why we do X," and Storytelling is "how you get it in the customer's head." (21:18) For example, Loom's positioning is video messaging for work, their story explains why (remote communication sucks), and their storytelling includes homepage copy, social media posts, and promotional tweets. The story must always point back to and justify the positioning, making it logical and compelling for prospects to choose your solution.
The Three Types of Marketing Enemies
Every company can create compelling conflict by identifying one of three types of enemies: direct competitors, competing approaches, or beliefs you stand against. (19:23) Apple vs. PC represents direct competitors, while London Underground vs. taxis shows competing approaches to the same problem. Cruise's self-driving cars position against the belief that "humans are terrible drivers." The key question to identify your enemy: "What are we actually competing against?" This helps determine which type of conflict will resonate most with your audience.
Write Examples, Don't Write Explanations
Harry's fifth immutable law states that explanations kill stories - you must show, don't tell. (33:34) He references Good Will Hunting where Robin Williams doesn't explain love as "an active commitment," but instead gives a specific example of sleeping in a hospital room for two months. In B2B marketing, instead of explaining that your software "saves time," show the real cost breakdown of a $5 coffee expense that actually costs companies $55 in employee time and interruptions. Concrete examples are infinitely more powerful than abstract explanations.
Statistics & Facts
- Asana spent $345 million in advertising last year, while Basecamp spent only $2 million and achieved similar customer numbers. (09:19) This comparison illustrates the difference between throwing money at marketing versus mastering storytelling and writing.
- The real cost of a $5 coffee expense is actually $55 when accounting for employee time (3 minutes), manager approval (1 minute), finance processing (4 minutes), verification (1 minute), and final reconciliation. (32:00) This breakdown demonstrates the power of making abstract savings tangible and specific.
- 40,000 Americans were killed last year in car crashes, a statistic Harry suggests could be used by companies like Cruise to position against the belief that humans are terrible drivers. (20:17) This shows how real data can support belief-based positioning.
