How to Stop Sending Boring Holiday Cards & Other Agents' AI Holiday Secrets 🤫

Happy Halloween! What was the best costume you saw? My wife and I joined her brother and his wife in Mexico City and we brought some Beatles energy to the Festivities 🎵

This week’s fun started early with a live training I co-hosted on Wednesday with Skye Michiels. We focused on how agents can make the most of holidays which we both believe is the most impactful time of the year for agents to grow their business.

The chat was on fire 🔥 with creative ideas. It reminded us that the best strategies combine high-touch personal connection with high-tech efficiency. We collected the chat transcript and used AI to summarize and categorize the best ones. Below you’ll find a few great ideas and examples of how you can use AI to execute your own.

🎁 High-Touch Gifting

Many agents stressed a shift toward handmade, hyper-local, and deeply personal gifts. The power of making your client feel seen cannot be measured. Examples included…

• Homemade food like peppermint bark or sugar-spiced pecans.

• Custom ornaments that mark a "First Holiday" in their new home.

• Memorial wind chimes for clients who have lost someone this year.

• Gift cards to local restaurants or bakeries.

🎪 Memorable Events

It was clear that the end of the year is not just a time for giving a thing, but for building the community that many clients are yearing for these days.

• Pampering at a local spot (like a nail salon, spa or winery) for some relief for your clients during a stressful year.

• Dessert Pickup where clients swing by to pick up their choice of many holiday desserts.

• Kids-themed workshops, like a gingerbread house building or a holiday-themed cooking class to give the parents an activity for the little ones.

🎙️The Personal Communication

How you deliver the message matters just as much as the message itself.

• Personalized video messages expressing gratitude on Thanksgiving instead of a mass email.

• Home Equity Report delivered as a high-value personal letter (not a salesy CMA).

• Community Cookbook created by asking for family recipes from clients and republishing them in a mini-book you send back to everyone.

⚡️ Real Estate Holiday Ideas, Before & After AI

All these high-touch ideas are awesome, but they take time—time to plan, write, and organize and most importantly, customize to your clients. This is where AI becomes your most powerful assistant.

Instead of: Sending a generic market update. Now: Use AI to analyze your list of past sales (with names and home addresses included). Have it write personal letters to each client, “It’s been a few years since you bought 123 Main St for $500k. The market is showing a 20% value increase and here’s some examples why.” A warm, 1-page letter as a 'Holiday Equity Stocking Stuffer will remind them that while they are building memories in their home, they’re also building wealth. Keep it personal and celebratory, not salesy.

Instead of: Guessing what your top clients might want or giving the same gift to everyone. Now: "Act as my lead database analyst. I've uploaded a CSV of my top 50 clients with columns for 'Notes' and 'Interests'. Segment this list into 3 groups and match each client to one of the following 5 gift ideas: [Local Restaurant GC, Custom Home Ornament, Golf Store GC, High-End Dog Toys, Bakery Gift Box]. Output this as a new table I can use."

Instead of: Sending a generic "Happy Holidays" email to your database. Now: "Act as my scriptwriter. Write a warm, 60-second script for a Thanksgiving video. The key theme is gratitude. Then, ask me 5 questions about my year and my clients to help me add 2-3 specific, personal anecdotes to make it memorable."

What is your most successful holiday idea and how has Ai helped you make it happen?

—Matt

🎉 Make the most of the Holidays

If reading this and thinking, “I’m running behind with my holiday ideas and wish I could use AI to help”, then this is your moment. My final AI Marketing System for Top Real Estate Agents course of 2025 runs December 1-12.

• Turn holiday "thank you’s" into 2026 leads by having AI spot your top opportunities.

• Automate your most personal outreach, from video scripts to client-centric market reports.

• Build a custom AI trained on your market, your voice, and your past success.

📖 Keep reading

Issue #12 | Is Your AI Leaking Client Data?

Issue #11 | Meta Just Turned Every Video Into a Multi-lingual Reel.

Issue #10 | Apps In ChatGPT: Your One‐Window Agent Workflow.