10 Cool Holiday Marketing Ideas for Small Businesses

Patrick McFadden • November 8, 2013

Small businesses and organizations can easily get trapped in the day-to-day operations of their businesses to spend any time brainstorming cool holiday marketing ideas. Some businesses worry that marketing is too expensive, others may find it too time consuming.

Without keeping top-of-mind awareness with your prospects and customers, how will anyone remember you?

Here are  10 Cool Holiday Marketing Ideas for Small Businesses and Organizations . Save these ideas and use them to celebrate any holiday – all year long.

1. Be a Giver!

Give a gift that shows you care with a donation to your prospects and customers favorite charity through  Charity Choice . Or get your employees involved and volunteer for a local or industry charity event. Write a holiday newsletter or blog with pictures and details about your positive impact.

2. Say “Cheese” For The Video Camera.

It’s a digital world, so why not think about creating a video holiday card? Record your office singing or video employees’ individual greetings. Post on YouTube or your website, then send them a link to view their special gift. 

3. Think BIG.

Everyone (including your prospects and customers) loves a chance to win BIG prizes like a Tablet or iPad, and now is the time to give them that chance. Ask people to sign up for your newsletter, etc. and enter them in a random drawing. And while in the spirit of giving, donate one to a local children’s hospital or community center.

4. Dress For The Occasion.

This holiday season have some fun by dressing up your website with festive backgrounds and graphics. Extend your theme to your e-mail signature and social media accounts too! Spread holiday cheer everywhere you can – just keep it appropriate for your entire audience.

5. Pick Up The Pen.

Express your holiday wishes and gratitude in a handwritten letter (mailed in a hand-addressed envelope of course). Enclose quality stationary or note cards personalized with their name or logo and you won’t just have a customer for life – you’ll have a friend too.

6. Options For Those Who Have Photo Block.

So you have a face for radio?  You can still take advantage of the digital “cool factor” (and save a tree) by sending your customers an eCard. Check out sites like  Enteract  f or a variety of designs and fun ways to personalize your greetings.

7. Think small.

Segment your holiday list and purchase gifts aligned with the value each customer, vendor, center of influence, or employee provides. Need something really special? Visit local boutiques or online shops like  Etsy.com  for unique, handmade items they will cherish.

8. Create a Picture to Remember.

Forget the corporate card catalogs and do something different. Hire a caricature artist to draw your department’s crazy characters, or have a professional designer create a cool holiday scene with your office and logo. Use your art for cards, calendars or your website.

9. Bypass Traditional Holidays.

Why not skip the holiday card clutter altogether? Eliminate the competition and stand out by celebrating new beginnings with a New Year’s mailing. Or, show a little love on Valentine’s Day.

10. Resist Temptation.

Sure, you are sending something to a lot of people and spending money on postage anyway. Why not slip in a brochure or business card? Save that for a later time and focus on sharing nothing but good cheer this holiday season. You will be rewarded with respect.

Question: What cool holiday marketing have you done before?

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The Missing Layer in AI: Why Judgment, Not Just Data, Will Define the Next Era of Intelligence

By Patrick McFadden • May 2, 2025
Everyone is scaling outputs. Almost no one is scaling judgment.

Everyone Talks About AI Judgment. We Built It.

By Patrick McFadden • May 2, 2025
Ask anyone in tech where AI is headed, and they’ll tell you: “The next leap is reasoning.” “AI needs judgment.” “We need assistants that think, not just answer.” They’re right. But while everyone’s talking about it, almost no one is actually shipping it. So we did. We built Thinking OS™ —a system that doesn’t just help AI answer questions… It helps AI think like a strategist. It helps AI decide like an operator. It helps teams and platforms scale judgment, n ot just generate output. The Theory Isn’t New. The Implementation Is. The idea of layering strategic thinking and judgment into AI isn’t new in theory. The problem is, no one’s been able to implement it effectively at scale. Let’s look at the current landscape. 1. Big Tech Has the Muscle—But Not the Mind OpenAI / ChatGPT ✅ Strength: Best-in-class language generation ❌ Limitation: No built-in judgment or reasoning. You must provide the structure. Otherwise, it follows instructions, not strategy. Google DeepMind / Gemini ✅ Known for advanced decision-making (e.g., AlphaGo) ❌ But only in structured environments like games—not messy, real-world business scenarios. Anthropic (Claude), Meta (LLaMA), Microsoft Copilot ✅ Great at answering questions and following commands ❌ But they’re assistants, not advisors. They won’t reprioritize. They won’t challenge your assumptions. They don’t ask: “Is this the right move?” These tools are powerful—but they don’t think for outcomes the way a strategist or operator would. 2. Who’s Actually Building the Thinking Layer™? This is where it gets interesting—and thin. Startups and Indie Builders Some small teams are quietly: Creating custom GPTs that mimic how experts reason Layering in business context, priorities, and tradeoffs Embedding decision logic so AI can guide, not just execute But these efforts are: Highly manual Difficult to scale Fragmented and experimental Enterprise Experiments A few companies (Salesforce, HubSpot, and others) are exploring more “judgment-aware” AI copilots. These systems can: Flag inconsistencies Recommend next actions Occasionally surface priorities based on internal logic But most of it is still: In early R&D Custom-coded Unproven beyond narrow use cases That’s Why Thinking OS™ Is Different Instead of waiting for a lab to crack it, we built a modular thinking system that installs like infrastructure. Thinking OS™: Captures how real experts reason Embeds judgment into layers AI can use Deploys into tools like ChatGPT or enterprise systems Helps teams think together, consistently, at scale It’s not another assistant. It’s the missing layer that turns outputs into outcomes. So… Is This a New Innovation? Yes—in practice. Everyone says AI needs judgment. But judgment isn’t an idea. It’s a system. It requires: Persistent memory Contextual awareness Tradeoff evaluation Value-based decisions Strategy that evolves with goals Thinking OS™ delivers that. And unlike the R&D experiments in Big Tech, it’s built for: Operators Consultants Platform founders Growth-stage teams that need to scale decision quality, not just content creation If Someone Told You They’ve Built a Thinking + Judgment Layer™… They’ve built something only a handful of people in the world are even attempting. Because this isn’t just AI that speaks fluently. It’s AI that reasons, reflects , and chooses. And in a world that’s drowning in tools, judgment becomes the differentiator. That’s the OS We Built Thinking OS™ is not a prompt pack. It’s not a dashboard. It’s not a glorified chatbot. It’s a decision architecture you can license, embed, or deploy— To help your team, your platform, or your clients think better at scale. We’ve moved past content. We’re building cognition. Let’s talk.

We Found the Missing Layer AI Has Been Waiting For

By Patrick McFadden • May 2, 2025
In every era of innovation, there’s a silent bottleneck—something obvious in hindsight, but elusive until the moment it clicks. In today’s AI-driven world, that bottleneck is clear: AI has speed. It has scale. But it doesn’t have judgment . It doesn’t really think . What’s Actually Missing From AI? When experts talk about the “thinking and judgment layer” as the next leap for AI, they’re calling out a hard truth: Modern AI systems are powerful pattern machines. But they’re missing the human layer—the one that reasons, weighs tradeoffs, and makes strategic decisions in context. Let’s break that down: 1. The Thinking Layer = Reasoning with Purpose This layer doesn’t just process inputs— it structures logic. It’s the ability to: Ask the right questions before acting Break down complexity into solvable parts Adjust direction mid-course when reality changes Think beyond “what was asked” to uncover “what really matters” Today’s AI responds. But it rarely reflects. Unless told exactly what to do, it won’t work through problems the way a strategist or operator would. 2. The Judgment Layer = Decision-Making in the Gray Judgment is the ability to: Prioritize what matters most Choose between imperfect options Make decisions when there’s no clear answer Apply values, experience, and vision—not just data It’s why a founder might not pursue a lucrative deal. Why a marketer might ignore the click-through rate. Why a strategist knows when the timing isn’t right. AI doesn’t do this well. Not yet. Because judgment requires more than data—it requires discernment . Why This Is the Bottleneck Holding Back AI AI can write. It can summarize. It can automate. But it still can’t: Diagnose the real problem behind the question Evaluate tradeoffs like a founder or operator would Recommend a path based on context, constraints, and conviction AI today is still reactive. It follows instructions. But it doesn’t lead. It doesn’t guide. It doesn’t own the outcome. And for those building serious systems—whether you’re running a company, launching a platform, or leading a team—this is the wall you eventually hit. That’s Why We Built Thinking OS™ We stopped waiting for AI to learn judgment on its own. Instead, we created a system that embeds it—by design. Thinking OS™ is an installable decision layer that captures how top founders, strategists, and operators think… …and makes that thinking repeatable , scalable , and usable inside teams, tools, and platforms. It’s not a framework. It’s not a chatbot. It’s not another playbook. It’s the layer that knows how to: Think through complex decisions Apply judgment when rules don’t help Guide others —human or AI—toward strategic outcomes This Is the Missing Infrastructure Thinking OS™ isn’t just about better answers. It’s about better thinking—made operational. And that’s what’s been missing in AI, consulting, leadership development, and platform design. If you’re trying to scale expertise, install judgment, or move from tactical to strategic… You don’t need a faster AI. You need a thinking layer that knows what to do—and why. We built it. Let’s talk.
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