The Cookie That Closed a $150K Land Deal w/ Josh Pierce

In this episode, Ajay and I sat down with Josh Pierce, a fast-rising land investor who built a high-performing business from scratch in under two years. Josh went from having zero experience and no capital—literally funding the business on a credit card—to now running a team of nine and generating six figures in monthly gross profits.

What makes Josh especially fascinating is his unconventional but wildly effective approach to gaining trust from sellers. He sends gourmet cookie boxes. No joke. This “cookie closer” method has helped him win deals that most land investors would have lost.

We dig into everything, from how he transitioned from fitness coaching to land investing, what he learned from taking massive risks, building and scaling his team, and his unique take on building trust with sellers. Josh also shares the truth about texting vs. direct mail, his hiring strategy, and what most new land flippers are getting completely wrong.

If you’re serious about scaling your land investing business or just want a new way to approach sellers, you need to hear this.

Links and Resources

Key Takeaways

In this episode, you will:

• Learn how Josh scaled from zero to $400K in his first year by using credit cards to fund his business and hiring VAs within 6 weeks.
• Discover the “Cookie Closers” strategy of sending $50 high-end cookie boxes to motivated sellers as “deal insurance” to build trust and close more deals.
• Understand how diversifying from direct mail to SMS texting helped Josh reduce key-man risk while maintaining 7X ROAS on both channels.
• Explore Josh’s hiring strategy of starting with generalists who can “build the fire” rather than specialized roles, then expanding based on business bottlenecks.
• See how focusing on the customer journey and always doing what you say you’ll do creates trust that makes sellers choose you over higher offers.

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