The New Rules of Direct Mail Marketing with Jessey Kwong

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The REI Marketing Weekly with Josh Culler

Josh Culler

155 episodes

4 hours ago

If you're an active Real Estate Investor that wholesales, flips, holds, turnkeys, or anything in between, and you're struggling with inbound or outbound marketing, this podcast is for you. Josh Culler has been in the investing industry since 2012 and has helped over 250 investors in their marketing efforts. On this show Josh interviews actual investors that are crushing it in their marketing to share what they're doing in their actual business.

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The New Rules of Direct Mail Marketing with Jessey Kwong

The REI Marketing Weekly with Josh Culler

31 minutes 27 seconds

5 months ago

The New Rules of Direct Mail Marketing with Jessey Kwong

In this episode of the REI Marketing Weekly, I’m joined by Jessey Kwong from Pebble REI for one of the most refreshingly honest and strategic conversations I’ve had on the show. We break down why direct mail is still thriving for investors who know how to niche their messaging, personalize their approach, and pair mailers with other marketing channels. Jessey shares data-driven insights from his platform and real-world stories that prove the old-school method is not only relevant—but evolving in a big way.

We also go beyond direct mail to talk about how the smartest marketers balance being proactive and reactive. Whether you’re new to real estate marketing or a seasoned pro, this episode is packed with insights that will help you better adapt, optimize, and get the most out of your budget and time.

Episode Timeline & Highlights

[0:00] - Why staying updated on marketing trends is vital for success

[1:22] - Marketing is both proactive and reactive—here’s how to balance both

[2:20] - Introduction to Jessey Kwong and his CRM platform for real estate

[3:25] - Why direct mail still works: consistency in lead flow despite declining use

[4:08] - How investors are leveraging the drop in mail competition

[6:23] - Jessey’s take on traditional vs. problem-based messaging

[10:23] - The power of personalized mailers: maps, doodles, and human touches

[11:37] - What makes mailers stand out in today’s crowded marketing space

[15:28] - Combining mail with texting and cold calling for better engagement

[18:02] - Rising costs in direct mail: How to adjust your marketing budget

[21:24] - Don’t get spoiled—why all marketing channels eventually shift

[23:35] - Staying creative before your results decline

[25:11] - Why successful marketing requires delegation and expertise

[27:08] - Jessey’s platforms, podcasts, and ways to connect

5 Key Takeaways:

Direct Mail is Not Dead – While fewer investors are using it, those who personalize and target their campaigns are seeing consistent ROI.
Relevance is the Secret Sauce – Messaging that’s problem/solution focused and hyper-specific outperforms generic “we buy houses” mailers.
Pair Channels for Power – Combine mail with texts or cold calls to create a seamless, multi-touch experience that boosts response rates.
Adjust Budgets Proactively – Rising mail costs don’t mean giving up—work backward from margins and forecast smarter to stay profitable.
Marketing Requires Balance – Being both proactive and reactive is essential to adapting strategies that evolve with the market and customer behavior.

Links & Resources

Pebble RCI CRM for Real Estate Investors: https://pebblerei.com
Jessey’s Podcasts:
- Land Investing Business Secrets
- Wholesaling Secrets
YouTube: Pebble REI Channel

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