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Chris Duff

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AI Mailer Tactics – Slow Market Warfare

What I’m thinking about: Injecting life into difficult markets with a combo of bottom-up market analysis, AI assistance, and an eye for detail.

We just deployed our most sophisticated mailer strategy yet for our Louisiana subdivide (three top-of-the-line parcels stuck in a grinding market.)

NOTE: The market has started showing some green shoots over the past week, fortunately, and we continue to be positioned better than any other offerings on the market, with ~2.5x margin still built in.

That being said, this is not a market to be resting on your laurels. As I’ve mentioned in a previous article, we are treating this project as the #1 priority in our business.

Every single day, we ask ourselves if there is ANYTHING else strategic or tactical to help encourage a favorable sale.

Here’s a strategy we spent much of the last 10 days working on, and hopefully it helps your business.

The Postcard Optimization Marathon:

We had some hotspots of locations where people were routinely clicking on our listings (more on this later).

Our broker suggested we could put together a flyer that advertised our properties as “executive estates,” to homeowners in those hotspots, threading the needle between generating further interest in our offerings…while not appearing desperate for buyers, given our upmarket positioning.

We put together a draft of a two-page flyer utilizing ChatGPT based on the transcript of the conversation I had with our broker strategizing on the flyers.

The broker thought it was too wordy and sent back a Canva-generated draft of a double-sided postcard instead, showcasing beautiful images of the property and highlighting a well-designed QR code that linked to all three of the available parcels.

Our ops manager prompted AI to carefully review and grade the postcard based on perceived marketability, producing a report with several tactical updates about 80% of which we agreed would be optimal changes.

Key changes: better photo hierarchy, stronger proof elements, improved readability, tactical pricing presentation, etc.

(I debated including some of the exact suggestions from AI, but for the sake of article length and complexity, decided against it. Suffice to say, impressively detailed and thoughtful.)

Few brief examples:

  • Instead of raw prices, we anchored at “$35K per acre” and let buyers do the math for total cost. Psychological pricing that feels more accessible while maintaining premium positioning, and screening for tire kickers.
  • Added authoritative credibility builders: “#1 school district, per the Louisiana Department of Education.” When you’re fighting for attention, every proof point matters.
  • Included secondary CTA with a short vanity URL under the QR, since not everyone will scan.

Several iterations passed back and forth between myself, our Ops Manager, our broker, and AI to re-review.

When you’re trying to stir up buyers for near-half-million-dollar properties in a difficult market, every detail needs to be scrutinized.

The AI-Powered Targeting Process:

Our broker’s ListTrac MLS hotspot data showed areas where people were repeatedly clicking our listing.

Unfortunately, the granularity of the hot spots was limited, and most were in denser infill areas, potentially representing hundreds of households, where it could have been only ONE person clicking our listing in that area.

Mailing everyone in those hot spots would cost thousands of dollars that we did not have budgeted.

So we fed the challenge to ChatGPT: “Here’s our budget, here are the hotspots, here’s our premium property profile. Design the optimal buyer targeting strategy.” (paraphrasing of course, that’s a pretty terrible prompt on its own.)

AI delivered a priority tier system:

  • 60% budget: Recent acreage buyers, near our price point (5-20 acres, last 3 years)
  • 20% budget: Nearest neighbors within 2 miles
  • 10% budget: Active rural builders and custom home GCs
  • 10% budget: High-equity homeowners in hotspot suburbs

(Sound logic: recent acreage buyers already proved they’ll spend at our price point, and high-equity suburban owners have HELOC capacity for land purchases, or may want to go ‘up-acreage.’)

Plus, ChatGPT gave us the precise SOP on pulling those lists from DataTree.

Ultimately, we pulled about 500 scrubbed and qualified prospects in our primary batch and a few hundred secondary prospects to save for a subsequent mailer if we get calls, site visits, or even a sale from the first batch.

Also, we set up dual-touch strategy, where we will skip-trace and call/text the top ~10% highest-priority prospects…again, being careful to focus the marketing on a “Hey, did you hear about this premium land in the area?” vs. trying to dig up buyers to sell at a discount.

The 6 x 11 postcards will hit mailboxes this week. TBD.

TL;DR:

AI amplifies strategy, doesn’t replace judgment. Notice how integrated AI is in our decision-making flow. We don’t treat its output as gospel, but it’s a valuable consultant that allows us to optimize tactics that would take hours/days of trial and error or additional research to get to on our own.

Premium properties need premium presentation. In slow markets, presentation quality and thoughtfulness becomes your primary differentiators. While we got a bad first draft prepped almost immediately (a reminder to not wait to start taking action), almost a week’s worth of iterations were appropriate to get the output to the standard we needed.

Surgical beats spray-and-pray in wartime markets. We started with the constraint of a capped budget and worked back from there. So many other operators only consider overhead impact once they’ve already spent the money, and they wonder why their margins compress or even become negative. Business is a game of math.

Multi-touch maximizes qualified leads. A postcard gets attention, but phone calls and texts to top prospects is the extra mile that might land a ~$500K sale. Don’t be afraid of elbow grease.

Market conditions demand tactical evolution. Most folks in the industry are having a tough year. (Even though we’ve had our most profitable year by a longshot, and are sitting on a pile of cash, subjectively it hasn’t felt like it. We’ve had to fight and claw to win.) Either adapt your dispo tactics, or accept stagnation/death of your business.

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Need funding for your next premium land deal? Serious Land Capital specializes in higher-value acquisitions ($50K minimum purchase price) with sophisticated exit strategies. Our always-evolving tactical expertise in difficult markets means better protection and profits for your deals.

P.S. Our ops manager’s reaction when he sent over the final postcard draft, and I’m like “Well, actually…” XD

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