Why Your 100-Person Newsletter Beats a 100,000-Person Audience (And Commands 10x the Price) | Lazy Leverage #69

Jon and Peter crack open one of the most perplexing puzzles in modern B2B marketing: why Peter's tiny 15,000-subscriber newsletter drives a significant fraction of what Daring Fireball makes with 2.5 million monthly visitors. And why Shaan Puri, with his top-10 business podcast, converted exactly 6 customers from 550 referrals to Somewhere.

The conversation starts with their origin stories - Jon's 2009 CrossFit philosophy blog that got him flown places at 24, Peter's Twitter journey that Moses Kagan pushed him into -but quickly evolves into something more profound. They're seeing a fundamental shift in how skeptical business owners make purchasing decisions. The old playbook of interrupt marketing, Facebook ads, and growth hacking for maximum eyeballs is dying.

Replacing it are high-trust vertical communities where people actually pay to participate. In fact, Jon says that he’d rather own a vertical community than a vertical SaaS right now. In an era of AI-generated content slop, business owners will increasingly retreat to closed communities for their most important decisions.

Jon and Peter dissect why generic business influencers fail while niche operators thrive. The secret sauce isn't just authenticity - it's having skin in the game and being willing to piss people off. As Jon puts it, channeling Chappelle: "You don't always have to be funny, but you always have to be interesting."

Key Topics: (08:15) The B2B Marketing Crisis: Why Vendors Can't Reach Customers (11:00) Shaan Puri's 1% Conversion Rate Problem (19:29) Jab, Jab, Jab, Right Hook (22:58) Why Vertical Communities Beat Vertical SaaS (27:57) The Peter Playbook vs. The Media Playbook (32:21) Authenticity and Showing Up Online (35:47) The Michelin Guide Strategy for Customer Acquisition (41:00) Having Skin in the Game: Why Business Influencers Fail (45:46) Final Thoughts: Automatic Blinds and AI Customer Databases

Stay connected for more insights and strategies by following: Jon: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@MatznerJon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ on X and at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠lazyleverage.beehiiv.com⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Peter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠@pslohmann⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ on X and at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠peterlohmann.com