The $50K Mistake: What Bad AI Strategy Really Costs Your Business
Jul 10, 2025
When AI Is Your Business's Worst Employee: Horror Stories from the Tech Trenches
Read Time - 3 minutes
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Hey there,
Last week, I got a call from a business owner in complete panic mode.
"Alyssa, I think some of our customers have been deleted."
Turns out, he was right. Sort of.
His team had set up two automations that were supposed to work together. Instead, they were playing tug-of-war with his customer database. Every time they tried to update a contact, the system automatically deleted them.
For an entire year.
When we looked at the damage, we could only recover two contacts from the recycling bin. Two. Out of hundreds.
Here's What Nobody Tells You About AI
Everyone's excited about AI being like "an employee that never asks for breaks or holidays."
But here's the thing they don't mention: that employee also never questions your worst decisions.
Tell a human to "delete all contacts" and they might push back. Tell AI the same thing and it responds with "Yes, captain" and starts deleting. No questions asked.
The $50K Question
This got me thinking about all the AI horror stories I've witnessed over the past decade as a tech consultant. Stories that would make you think twice about that "quick AI implementation" you've been considering.
Because here's the uncomfortable truth: bad AI can actually be MORE damaging to your business than doing everything manually.
I'm talking worse than hunting down customers door-to-door.
What's Really at Stake
In today's full article, I'm sharing the three biggest AI disasters I've witnessed (including the "devil flow" that had a life of its own), plus the one principle that separates AI success stories from $50K mistakes.
You'll discover:
- Why the "garbage in, garbage out" principle is exponentially more dangerous with AI
- The furniture company data war that destroyed months of sales information
- How one contact form nearly required 5,000 automations to manage
- The one question that reveals if your current setup is a ticking time bomb
Read the Full Framework Here →
Cheers,
Alyssa Schaefer (aka The Business Cowgirl 🤠)
P.S. Pro tip: Don't let AI become your business's worst employee. Get the strategy right from the start.
Whenever you're ready, there are 3 ways I can help you:
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- Deep Dive Tech Audit (Build Your 90 Day Plan): We go under the hood of your entire tech stack, identify what's really broken (not just what feels broken), and create your personalized 90-day roadmap to reclaim 10+ hours per week through streamlined workflows.
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Howdy, I'm The Business Cowgirl
(aka Alyssa Schaefer 🤠)
Online Business Digital Architect and AI Strategist
- 10+ years building businesses online and developing backend workflows
- Senior-level experience in business process automation and CRM optimization
- AI integration specialist with 2+ years focused on practical business applications
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- One Hour Tech Clarity Call: One focused hour to identify your biggest tech bottleneck and the fastest path to fix it. Think of it as your first coaching session with immediate, actionable results that you can implement this week.
- Deep Dive Tech Audit (Build Your 90 Day Plan): We go under the hood of your entire tech stack, identify what's really broken (not just what feels broken), and create your personalized 90-day roadmap to reclaim 10+ hours per week through streamlined workflows.
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