I got an email last week that started with "Hey Dan, I noticed you're interested in marketing automation for businesses in Detroit doing $15-30K monthly..."

Sounds personalized, right? Like someone actually researched me and crafted a thoughtful message?

Except it wasn't. It was an AI-generated email sent to 10,000 people with slightly different variables plugged in. And I could tell immediately.

You know how I knew? Because it was too perfect. Too specific. Too "I definitely didn't spend 30 seconds researching you, but I want you to think I did."

This is the hyper-personalization trap of December 2025. AI has made it possible to personalize everything at scale. So everyone's doing it. And it's backfiring spectacularly.

The AI marketing automation market hit $10.3 billion this year, and a huge chunk of that is being spent on personalization tools. Tools that scrape LinkedIn. Tools that analyze website behavior. Tools that predict what you want before you know you want it.

And most of it feels creepy as hell.

Here's what's happening: businesses are confusing personalization with surveillance. They're confusing relevance with stalking. They're using AI to create the illusion of personal attention while actually treating people like data points.

And customers are getting wise to it.

Today, I'm going to show you why most "personalized" marketing is failing, what actually works in December 2025, and how to use AI to create genuine connections instead of creepy automation.

The Personalization Arms Race

Let's rewind to 2023. Personalization was still kind of special. If you got an email that referenced your company name or your industry, it felt thoughtful. It stood out.

Fast forward to December 2025. Everyone's doing it. Every cold email mentions your company. Every LinkedIn message references your recent post. Every ad seems to know exactly what you were just looking at.

And instead of feeling special, it feels invasive.

This is what happens when a tactic becomes a commodity. When everyone's doing the same thing, it stops working. It becomes noise.

I call this the personalization arms race. Businesses keep adding more data points, more customization, more "personal touches" to try to stand out. But they're all doing the same thing, so nobody stands out.

You get emails that say, "I saw you recently posted about [topic] and I thought you might be interested in [product]." Except you know they didn't actually read your post. An AI scraped it and plugged it into a template.

You get LinkedIn messages that reference your job title, your company size, your industry, and your recent activity. Except it's obvious they're using a tool that does this automatically for thousands of people.

You get retargeting ads that follow you around the internet, showing you the exact product you looked at three days ago. Except instead of being helpful, it's just annoying.

The problem isn't personalization. The problem is fake personalization.

What Actually Feels Personal in 2025

Real personalization isn't about data points. It's about understanding.

Let me show you the difference.

Fake Personalization: "Hey Dan, I noticed you're a marketing consultant in Detroit. I help marketing consultants in Detroit get more clients. Want to chat?"

This is template-based personalization. They plugged in my name, my job, and my location. It took zero thought and zero understanding of what I actually need.

Real Personalization: "Hey Dan, I read your article about no-show prevention and the 40% to 12% reduction you achieved. I'm working with a consulting firm that's struggling with the same issue. Would you be open to a quick call to discuss your approach?"

This shows they actually consumed my content, understood the specific problem I solve, and have a relevant reason to reach out.

See the difference?

One is about me (my demographics, my location, my job title). The other is about my work (my ideas, my results, my expertise).

One feels like spam with my name on it. The other feels like someone actually paid attention.

The Three Levels of Personalization That Work

As we close out 2025, I've identified three levels of personalization that actually create connection instead of creepiness.

Level 1: Behavioral Personalization

This is personalization based on what people do, not who they are.

If someone downloads your lead magnet about email marketing, your follow-up sequence should be about email marketing. Not about your full product suite. Not about unrelated topics. Just email marketing.

If someone abandons their cart, your follow-up should address cart abandonment. Maybe they had a question. Maybe the price was too high. Maybe they got distracted. Your message should acknowledge this specific behavior.

This works because it's relevant and timely. You're responding to an action they took, not making assumptions about who they are.

Example: Someone downloads your "28-Hour Work Week" guide about automation. Your follow-up sequence focuses on automation topics, automation case studies, and automation tools. You're not trying to sell them on social media strategy or SEO services. You're staying in the lane they expressed interest in.

Level 2: Contextual Personalization

This is personalization based on where someone is in their journey.

A first-time visitor needs different information than someone who's been following you for six months. Someone who has just discovered you needs education. Someone who's been engaging with your content for weeks needs a clear path to work with you.

This works because it respects where people are. You're not trying to close someone on day one. You're not still educating someone ready to buy.

Example: New subscriber gets a welcome sequence that introduces your philosophy, your best content, and your free resources. Someone who's opened 10+ emails and clicked multiple links gets an invitation to book a strategy call. Someone who's been on your email list for 90 days but hasn't engaged gets a re-engagement campaign.

Level 3: Relationship Personalization

This is personalization based on actual interaction and relationship history.

If someone replied to your email, your next message should reference that conversation. If someone attended your webinar, your follow-up should mention specific points from the webinar. If someone's been a customer for a year, your communication should reflect that relationship.

This works because it's real. You're not pretending to know them. You actually do know them because you've interacted.

Example: A client who implemented your no-show prevention automation and got great results gets a follow-up asking if they're ready to tackle their next automation challenge. You're not pitching them on the same thing again. You're building on the relationship and the results they've already achieved.

The AI Tools That Enable Real Personalization

Here's the tech stack that's working for genuine personalization in December 2025.

For understanding customer behavior: You need a CRM that actually tracks meaningful interactions. Not just "opened email" or "clicked link." You need to know what content they consumed, what problems they're trying to solve, and where they are in their journey.

I'm using GoHighLevel for this because it integrates everything (email, SMS, calls, meetings, purchases) into one view. You can see the full customer journey, not just fragments. (Link: https://www.gohighlevel.com/?fp_ref=your-friend-frank72)

For AI-powered insights: You need tools that help you understand patterns, not just collect data. Galaxy.ai is perfect for this because you can feed it customer data and ask questions like "What are the common themes in my most engaged subscribers?" or "What objections keep coming up in sales calls?" (Link: https://galaxy.ai/?ref=danr2)

For meeting intelligence: Fathom.video records and transcribes every customer call, then uses AI to identify key moments, action items, and insights. This is relationship personalization at scale. You can reference specific things discussed in previous calls without having to remember everything manually. (Link: https://fathom.video/invite/c-kq_A)

For content personalization, You need a system that delivers different content based on behavior and interests. Beehiiv does this well with segments and conditional content. You can show different CTAs, different case studies, different offers based on what someone's interested in. (Link: https://www.beehiiv.com?via=Dan-Kaufman)

But here's the key: these tools enable personalization. They don't create it. You still need strategy, understanding, and genuine interest in helping people.

The Creepy Line: How to Know If You've Crossed It

Here's a simple test: if you wouldn't say it in person, don't say it in an automated message.

Would you walk up to someone at a networking event and say, "I noticed you recently visited my website three times and looked at my pricing page for 4 minutes and 37 seconds"? No. That's creepy.

Would you say, "I saw you posted about struggling with no-shows and I've helped other businesses solve that exact problem"? Yes. That's helpful.

The creepy line is crossed when you use information that people didn't explicitly share with you in a way that makes them uncomfortable.

Creepy:

Not Creepy:

The difference is consent and context. If someone downloaded your guide about automation, they've consented to receive information about automation. If someone visited your pricing page, they haven't consented to be reminded about it in a creepy way.

The Framework: Personalization That Builds Trust

Here's the framework I use for all personalization in December 2025.

Step 1: Segment by Interest, Not Demographics

Stop segmenting by job title, company size, or industry. Start segmenting by what people care about.

Someone who downloaded your automation guide cares about automation. Someone who attended your webinar about no-shows cares about no-shows. Someone who clicked your case study about revenue recovery cares about revenue recovery.

Send them more of what they've shown interest in. It's that simple.

Step 2: Personalize the Problem, Not the Person

Your message should address the specific problem someone's trying to solve, not make assumptions about who they are.

Instead of "As a marketing consultant in Detroit..." try "If you're struggling with no-shows eating into your revenue..."

One is about demographics. The other is about problems. Problems are universal. Demographics are assumptions.

Step 3: Use AI to Scale Understanding, Not Fake Intimacy

AI should help you understand patterns and deliver relevant content. It shouldn't try to fake personal relationships.

Use AI to analyze which content resonates with which segments. Use AI to identify common questions and objections. Use AI to deliver the right message at the right time.

Don't use AI to pretend you personally researched someone when you didn't. Don't use AI to create the illusion of individual attention when you're sending the same message to thousands of people.

Step 4: Make It Easy to Opt Out or Adjust

Real personalization respects preferences. Every email should have clear options to adjust frequency, change topics, or unsubscribe.

If someone's not interested in automation content anymore, let them switch to a different topic. If someone wants weekly emails instead of daily, let them choose.

This builds trust because it shows you care more about being helpful than being persistent.

The Results: What Happens When You Get This Right

Let me show you what happens when you do personalization right in December 2025.

Client A: SaaS company with 50,000 email subscribers. They segmented by interest instead of demographics and personalized content based on behavior. Open rates went from 18% to 34%. Click rates went from 2.1% to 7.8%. Revenue from email increased by $127K annually.

Client B: Consulting firm with 5,000 subscribers. They stopped using AI to fake personal research and started using it to deliver genuinely relevant content based on what people downloaded and engaged with. Reply rates on outreach went from 3% to 19%. Booked calls increased by 340%.

Client C: E-commerce brand with 100,000 customers. They implemented behavioral personalization in their abandoned cart and post-purchase sequences. Recovery rate on abandoned carts went from 8% to 23%. Repeat purchase rate increased by 41%.

The pattern? When you stop trying to fake intimacy and start delivering genuine relevance, people respond.

What's Next

If you want to build personalization that actually works, start with understanding, not data collection.

First, grab "The 28-Hour Work Week" guide. It includes a section on behavioral personalization and the exact segments that work best for different business types. [Link to lead magnet]

Second, if you want help implementing this in your business, the Dead Simple Growth Automation Pack includes pre-built behavioral personalization sequences for lead nurturing, abandoned cart recovery, and customer onboarding. It's $97 and includes both Make.com and Zapier templates. [Link to automation pack]

And if you're doing over $15K/month and you want a personalization strategy built specifically for your business, let's talk. I offer done-for-you personalization audits where we analyze your current approach, identify opportunities, and implement behavioral personalization that actually builds trust. It's $1,997 and includes strategy, implementation, and 30 days of optimization. [Link to services page]

The Bottom Line

Hyper-personalization is everywhere in December 2025. Most of it is creepy, fake, and ineffective.

The businesses winning are the ones using AI to scale understanding and relevance, not to fake intimacy.

Stop trying to prove you researched someone. Start proving you understand their problem.

Stop collecting more data points. Start using the data you have to be genuinely helpful.

Stop automating fake personal touches. Start automating real value delivery.

Personalization isn't about knowing everything about someone. It's about understanding what they need and delivering it at the right time.

Let's build that.

Dan

P.S. If this resonated with you, forward it to someone who's getting creepy marketing messages and wondering why their own personalization isn't working. And if someone forwarded this to you, subscribe here for more no-BS marketing strategies every Tuesday, Thursday, and Saturday.