Why do some businesses thrive on cold outreach and educational content while others find these tactics completely ineffective?

Peter draws on his own recent experience where, despite running monthly webinars all year with heavy promotion across multiple channels, his property management company barely attracts 20 live attendees (half being employees). Meanwhile, a hastily organized webinar for his other audience of property management business owners pulled 250 attendees with minimal effort.

"You can't cold call somebody and say, 'Hey, do you have any leaky pipes?'" Jon quips, making the point that property management marketing differs from other industries. When someone needs a plumber, they need one NOW. When someone needs a property manager, they either desperately need one or they don't. There's no middle ground you can market your way into.

Next, Jon and Peter talk marketing economics. With a $45,000 lifetime value but a one-year payback period where they lose money, Peter's property management business faces unique challenges. Jon proposes radical solutions: downselling to free management forever (monetizing through maintenance fees) or creating intro offers that recover customer acquisition costs immediately.

They explore the difference between home services (search-driven, time-sensitive, skilled labor constrained) and home improvement (demand creation, higher ticket, schedulable). Property management sits awkwardly between these models, explaining why consolidators prefer acquiring 150-door portfolios over organic growth.

Finally, Jon pushes Peter toward more aggressive marketing tactics: exploding offers, upsell sequences, and the Hormozi principle that "sales create sales." While Peter worries about cheapening his brand, Jon argues he's nowhere near that danger zone.

Understanding your industry's fundamental dynamics matters more than copying tactics from other sectors. The real work of leadership is setting and showing the standard, whether that's in marketing strategy or morning standups.

Key Topics: (04:34) Why Companies Acquire vs Grow Organically (17:23) The 3% Buyer's Pyramid Problem (25:05) Free Management Forever Downselling Strategy (32:05) The Power of Enriched Data Collection (36:50) Hormozi's "Sales Create Sales" Philosophy (42:55) Setting Standards as Leadership

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

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

Jon and Peter dive into one of those ideas that sounds crazy at first but might actually be brilliant: buying luxury vacation properties as a business expense that doubles as a killer member benefit. Jon's been noodling on this concept for months, and it's finally survived his brutal idea-filtering process (which involves annoying everyone from his CFO to random Twitter buddies until the bad ideas die off).

Here's the pitch: Sagan would purchase several properties—think ski chalets, beach houses, maybe something in Mexico—and offer them to members at 50-75% below Airbnb rates. The kicker? Thanks to bonus depreciation and some creative tax structuring, the whole thing could essentially pay for itself while adding a premium benefit that helps with member retention.

Peter initially pushes back hard on the operational nightmare this could become. Nobody wants to field calls about broken ice makers or dirty towels. But as they hash it out, the vision gets clearer: professional property management with multiple layers between Jon and any actual guest issues, properties strategically located for both vacations and corporate retreats, and a focus on serving their high-trust member base rather than random Airbnb guests.

Successful entrepreneurs develop strategy not through formal PowerPoints and weighted decision matrices, but through relentless debate, pattern recognition, and asking "will this actually f***ing work?" over and over until the answer becomes clear.

Key Topics: (01:49) The Art of Business Ideation: Volume Shooting vs. Analysis Paralysis (11:56) Introducing the Vacation Property Concept for Sagan Members (15:29) Bonus Depreciation and Tax Strategy Explained (21:29) Solving the Property Management Problem Before It Starts (27:51) Facilitating Global Team Meetups at Member Properties (31:11) Location Strategy: East Coast, West Coast, International (34:06) Building the Management Structure and Avoiding Operational Headaches

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