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.

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