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- The Paradox (Why Your AI Strategy Is Probably Doomed)
The Paradox (Why Your AI Strategy Is Probably Doomed)
95% of AI projects fail. Here's how to join the 5% that don't.

Coach Will here…Welcome!
I'm truly passionate about creating profitable businesses and developing effective strategies to make that happen.
But here's a statistic that might make everyone pause and think:
According to a landmark MIT Media Lab study published in August 2025, 95% of all AI initiatives deliver zero return on investment.
Not "disappointing returns." Not "slower than expected." Zero.
And here's the kicker: The study found that the problem isn't the technology. It's not that the AI doesn't work or that the tools are bad.
The problem is that most businesses approach AI completely backwards.
They start by asking "What AI tool should we buy?" instead of "What decision are we trying to make?"
They invest in solutions before they understand the problems.
They build dashboards nobody looks at, chatbots nobody uses, and automation that automates the wrong things.
Meanwhile, the 5% who succeed with AI do something radically different. They start with a single, highly specific question.
That's the AI Strategy Paradox. And once you understand it, you'll never waste money on AI hype again.
❌ The Approach That's Quietly Killing Businesses
Does this sound familiar or maybe it’s you?
You're running a growing company. Maybe you just crossed $1M in revenue. You have a small team, and things are moving fast.
Then you see your competitors launching "AI-powered" this and "intelligent" that. The pressure is on.
So you call a meeting. "We need an AI strategy," you declare.
Two weeks later, you're staring at a whiteboard full of buzzwords: AI chatbots, predictive analytics, automated content, sales forecasting.
You pick one, allocate $10,000, and hire a sharp freelancer. (Been there done that!)
Three months go by. The $10K is gone. And what exactly has changed?
The chatbot annoys customers. The analytics tool sits unused. You're right back where you started, only with a lighter wallet.
Of course your don’t want to hear the cold, hard truth: You started with AI and then went looking for a problem.
That's backasswards.
💬 Coach Will: "If you're shopping for AI tools before you know what problem you're solving, you're not building a strategy. You're collecting expensive hobbies."

It's not an "AI strategy." It's a business strategy that might, or might not, involve AI.
💡 One Question Changes Everything
Every business is just a series of decisions.
Where do we spend the marketing budget? Which customers are the most profitable? What product should we build next?
Good decisions compound into growth. Bad ones cascade into chaos and take you over the cliff.
AI is only useful if it helps you make a better decision. But you can't know if it will until you've defined the decision you're trying to make.
💬 Coach Will: "AI doesn't make bad decisions better. It makes good decisions faster. Know the right decision first, then ask if AI can help."
Here's how this plays out in the real world:
Most businesses track revenue. They know which marketing channels drive sales. But they don't know which channels drive profitable customers.
That's not an AI problem. That's a decision problem:
"Where should I allocate my ad budget to maximize profit, not just traffic?"
When you think about it like that, the answer is clear.
What you really need is a framework that links your ad spend directly to your actual profit, rather than just focusing on revenue.
AI-powered tools are great helpers!
They keep an eye on customer behavior across different channels, calculate how much customers are worth over their lifetime, and show you which channels truly bring in profitable customers.
It's like having a friendly assistant that helps you understand your business better.
But here's the key: The AI only works if you start with the right question.

🎯 The Decision-First Framework
My years of coaching and building businesses have taught me a valuable lesson: successful individuals all follow the same playbook.
Step 1: Identify your single most critical strategic decision. Not "where can we use AI?" but "what's the one decision that, if we got it right, would change everything in the next 90 days?"
Step 2: Determine what information would make that decision easy. If you had a magic wand, what number would you want to know?
Step 3: Ask if AI can help. Can an AI tool get you that information better, faster, or cheaper than a human can?
Step 4: Start small and measure everything. Run controlled experiments with clear budgets and success metrics.
🚀 AltLevel™ AI Power Prompt:
Copy this prompt into ChatGPT or you favorite tool to identify your most critical business decision in 5 minutes:
You are an AI strategy consultant and business advisor who helps founders leverage artificial intelligence for smarter, faster decision-making.
Background - My business currently has:
Annual revenue: [INSERT REVENUE]
Industry: [INSERT INDUSTRY]
Team size: [INSERT TEAM SIZE]
Biggest challenge: [INSERT CHALLENGE]
Your task:
Ask me 3–5 clarifying questions to better understand my goals, data environment, and decision-making process. Then help me identify:
The single most critical strategic decision I must make in the next 90 days.
The data, analytics, or insights required to make that decision with confidence.
Specific ways AI could support that process — such as forecasting, customer analysis, automation, or decision support.
Provide a clear, actionable decision statement and a brief summary of how AI could accelerate or improve the decision outcome.
Ask me any questions you have.What this does: It forces you to think strategically about your business, not tactically about AI tools.
You'll walk away with a clear decision statement like:
"Should I expand into the B2B market or double down on B2C?"
"Which customer segment should I focus my marketing budget on?"
Once you have that decision, you'll know exactly what information you need. And then—and only then—you'll know if AI can help.
This is how the 5% think.
💬 Coach Will: "The 95% who fail with AI start by asking 'What tool should we buy?' The 5% who succeed start by asking 'What decision are we trying to make?'"
⚡️ Your Next Step
Run that prompt. Write down and ponder your one critical decision.
Get obsessed with it.
That's your starting point. Not a demo. Not a sales call. That question.
Enjoy the process, be discipline and highly focused! But note, be flexible and pivot when you need to pivot.
Clarity, adaptibility and exection gets the deal done!
📊 Quick Poll:
Where Are You In Your AI Journey?(Your feedback helps us deliver the insights that matter most.) |
🎬 That's A Wrap
Here's what we covered this week:
The Problem: 95% of AI projects fail because founders begin with the technology and then look for a problem to solve. That's backwards.
The Solution: The Decision-First Framework. Begin with your most important business decision, determine what information you require to make it confidently, then consider if AI can assist you in obtaining that information.
Your Action: Use the AltLevel™ AI Power Prompt to identify your critical decision. Don't invest in AI until you clearly understand the problem you're solving.
The Bottom Line: The 5% who succeed with AI aren't smarter or better funded. They just ask better questions first.
See you next week when we unpack why the world's top CEOs are terrified and investing billions at the same time.
—Coach Will, Your Strategic Architect
P.S. That 95% failure rate isn't a technology problem; it's a strategy problem. The 5% who succeed aren't smarter or better funded. They ask better questions.
P.S.S.Reply to this email with one strategic decision you're struggling with right now. I'll use the most common challenges to shape upcoming newsletters. Your questions drive our content.
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