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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode of "What's Your Process?", Dave Gerhardt, founder of Exit Five, shares his copywriting methodology with host Dmitry Shamis. (09:53) Dave explains why he considers himself a "world-class copywriter" and breaks down his systematic approach to writing everything from landing pages to newsletters. The conversation covers his framework for creating compelling content, why formatting matters more than perfect prose, and how he decides when something is ready to ship. (23:48)
Dave is the founder of Exit Five, a community for B2B marketing professionals with nearly 5,000 members. He previously served as CMO at two tech startups that went through successful acquisitions and started his career in PR before transitioning to marketing. Dave has built his reputation as a content creator and copywriter, hosting hundreds of podcast episodes over the past decade.
Dmitry is the co-founder of OhSnap! and former Head of Brand and Creative at HubSpot, where he was one of the early pioneers of self-service brand systems for B2B tech. He hosts "What's Your Process?" podcast, conducting in-depth interviews with top marketers about their creative processes.
Dave's counterintuitive approach flips conventional writing advice on its head. (21:21) Instead of writing content first and then crafting a subject line or headline, he begins with what he calls the "hook" - the compelling element that will grab attention. This approach stems from his belief that "great writing is actually great editing," meaning the first idea is rarely the best one. For example, when his team member Erin sends him newsletter drafts, he rewrites every single subject line without fail because starting with something concrete helps his brain quickly identify what the real message should be. This method forces clarity from the beginning and ensures every piece of content has a clear, compelling entry point that will actually get people to engage.
Before writing anything significant, Dave systematically finds 1-3 high-quality examples of similar content to use as inspiration. (18:56) He explains that with billions of years of human history, "very few things are completely brand new and original." When working on Exit Five's newsletter improvements, he spent a week obsessing over Morning Brew and Lenny's Newsletter to understand what makes them successful. This isn't about copying - it's about understanding proven structures and approaches that work. The key is analyzing what you like about each example, then combining the best elements with your unique perspective and voice to create something that feels fresh but leverages tested frameworks.
Dave considers formatting one of the most underrated aspects of effective writing. (25:17) He uses the analogy "you eat with your eyes" - if content looks overwhelming or poorly structured, people won't read it regardless of quality. His approach involves breaking up text with clear sections, using headers to create visual hierarchy, and employing guardrails like "three core benefits" or "five reasons" to organize thoughts. He's particularly passionate about call-to-action formatting, preferring to hyperlink entire sentences rather than just words like "here" to maximize click real estate. This attention to visual presentation makes content more scannable and digestible, dramatically increasing the likelihood that busy professionals will actually consume your message.
Dave operates on a philosophy of strategic urgency, where the stakes determine how much polish something needs. (35:53) For high-stakes content like their marketing leadership retreat landing page, he sweats every word and includes personal touches like his actual signature. But for daily LinkedIn posts, he'll literally write while walking on a treadmill and post immediately, typos and all. The key insight is that in today's marketing environment, you get almost instant feedback on your work, unlike traditional advertising where you'd wait quarters for results. This allows for rapid iteration and improvement. He emphasizes that quality matters, but marketers often use "quality" as an excuse not to ship, when really they should be taking more at-bats and learning from each attempt.
Dave's biggest pet peeve in marketing copy is multiple competing calls to action, which he sees as a failure of strategic thinking. (30:30) Using the "risk of insult is the price of clarity" principle from Roy Williams' "The Wizard of Ads," he argues that trying to please everyone leads to confusing everyone. When editing emails, he'll remove four different CTAs to focus on just one primary action, even if it means disappointing internal stakeholders who want their projects featured. This philosophy extends beyond CTAs to overall messaging - instead of trying to communicate everything your product does, focus on guiding people through a logical next step sequence. The goal isn't immediate complete understanding, but building trust and credibility to earn the next interaction.