What Does It Take to Succeed in Land with Direct Mail? Featuring Jessey Kwong of Pebble
About this episode
Jessey Kwong discusses the evolving landscape of land investing and the importance of direct mail strategies.
In this episode, we sit down with Jessey Kwong from Pebble to talk about what’s changing in land investing and what the data is showing about direct mail. Jesse explains why the market has become tougher for people who treat land investing like a side hustle, while those who stay consistent and treat it like a real business are still finding opportunities. He also shares why follow-up and remarketing are working better than simply sending one campaign and moving on. The conversation breaks down what’s working in direct mail today, from simple 4x6 postcards to personalized messaging and using satellite images of properties. Jesse explains why knowing your market, targeting the right sellers, and building trust matter more than relying on generic templates. As the market gets more competitive, strong marketing and sales skills are becoming harder to ignore. Jesse also shares where Pebble is headed as AI and automation continue to change the industry. While AI can make administrative work easier, he believes land deals will still depend heavily on real conversations, trust, negotiation, and relationships. The tools may change, but the human side of doing business isn’t going away…
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