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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 candid solo episode of Exit Five, Dave Gerhardt answers 15 questions from his team about work, life, marketing, and everything in between. The episode covers his LinkedIn content creation process, daily routines, reading habits, career advice, and personal quirks in a refreshingly honest and unfiltered way. (02:05)
Dave Gerhardt is the founder of Exit Five, a private marketing community with nearly 5,000 members. He previously served as VP of Marketing at Drift and CMO at Privy, building his career expertise in content marketing, copywriting, and brand storytelling. Born in Worcester, Massachusetts, Dave has built a reputation as an authentic voice in B2B marketing through his popular LinkedIn content and podcast.
Dave shares career-defining advice from David Cancel at Drift about focusing on natural talents rather than trying to become well-rounded. (19:53) Cancel recommended Peter Drucker's "Managing Oneself," which teaches that it's better to become exceptional (A-grade) at your strengths than to improve weaknesses from D to B level. Dave was naturally gifted at writing, communication, and storytelling but wanted to become a "growth hacker" with technical skills. By doubling down on content and copywriting instead, he built the foundation for his entire career success, eventually leading to Exit Five's creation.
Dave's LinkedIn strategy has evolved from methodical planning to spontaneous, authentic writing that stands out in an AI-filled world. (02:08) He keeps ideas in Apple Notes and writes "off-the-cuff" posts during morning coffee, often including typos and unconventional capitalization. This authentic approach has helped him grow to nearly 200,000 followers because his writing style is distinctly non-AI. The lesson: in a world of polished, artificial content, being genuinely human and imperfect can be your competitive advantage.
Dave's definition of a perfect day centers on early morning discipline and physical activity before work begins. (09:37) His routine includes waking at 5:30 AM, working out from 5:45-6:45 AM, taking kids to school, then completing a 3-mile hike or ruck by 9:00 AM. This foundation of fitness and family time before "easy" computer work creates a sense of accomplishment and reduces stress. The key insight: front-loading your day with the hardest but most rewarding activities makes everything else feel manageable.
Dave struggles with online criticism but has learned that engaging with detractors is counterproductive. (15:02) He references Jay-Z's wisdom: "Don't argue with fools because people from a distance can't tell who is who." Despite receiving personal attacks about his marketing community, Dave chooses not to respond online, instead letting his work and in-person interactions speak for themselves. Many people who meet him say he's "way nicer and funnier than expected," proving that authentic character ultimately trumps online noise.
When feeling unmotivated, Dave draws inspiration from his friend Matt, a Marine who served in Afghanistan while Dave was "messing around in college." (21:56) This perspective immediately reframes any work challenges as manageable compared to actual combat situations. The technique works because it provides immediate context for how fortunate and relatively easy most professional obstacles are. This gratitude-based motivation strategy helps him tackle difficult calls, meetings, or travel with renewed energy.