#19 - Is it Time to Break Up With ChatGPT?
Wed Feb 04 2026
Are you a business owner frustrated with AI giving you made-up answers? You're not alone. In this episode of Weeks Ahead AI, we dive deep into why ChatGPT and other AI tools sometimes fail small business owners, and what you can do about it. Whether you run a construction company, HVAC business, plumbing operation, or any business, understanding the limitations of AI tools is crucial before you stake important business decisions on their output.
In This Episode:
Why AI models prioritize giving an answer over giving the right answer—and the real-world consequences for your businessThe "context window" problem explained: how your AI forgets critical information mid-conversationWhy one contractor nearly made costly financial decisions based on AI-generated "facts" that were completely fabricatedHow to test if your current AI tool is giving you biased or outdated answersThe simple "show your work" hack that catches AI mistakes before they cost you moneyWhich AI alternatives are outperforming ChatGPT for business analysis and planning
Timestamps:
[00:00] Introduction to Weeks Ahead AI – helping business owners save time and cut costs with AI
[01:04] The "gateway drug" problem: Why most business owners start with ChatGPT and never explore alternatives
[02:34] Terry's breakup story: Canceling ChatGPT after 18 months—and why it felt like a divorce
[03:20] The comfort trap: "It already knows my stuff" and why that's keeping you stuck
[05:00] When AI sounds like BS: Terry's first red flag that something was wrong
[05:48] "Great idea!" syndrome: Why your AI agrees with everything (even your worst ideas)
[07:04] The lawyer's warning: AI citing legal cases that never existed
[08:00] Financial analysis disaster: How bad AI advice could have cost thousands
[09:32] The spreadsheet nightmare: 3 days wasted trying to export 500 contacts
[11:05] Context window explained: Why your AI "forgets" important details mid-conversation
[12:14] The telephone game effect: How long chats corrupt your AI's memory
[14:35] The "show your work" hack: Making AI prove its logic before you trust it
[16:40] Memory bias problem: When AI applies wrong context to your current project
[17:24] Behind the scenes: Why some AI companies throttle performance without telling you
[18:18] Terry's current AI stack: Claude, Gemini, Grok, and Relay Hub
[19:08] Four days without ChatGPT: Did Terry notice any difference?
[20:40] ChatGPT introducing ads: What this means for users
[21:29] Final takeaway: Stay weeks ahead by pressure-testing multiple AI models
Links & Resources Mentioned:
Episode 2 – Deep dive on exporting and transferring your ChatGPT data to other modelsClaude AIGoogle GeminiGrok – Available through X/TwitterRelay Hub – AI workflow automation platform we are building.If you're still relying on just one AI tool for your business decisions, it's time to pressure test your options. Try running the same business question through 2-3 different AI models and compare the answers. You might be surprised at the differences.
Subscribe to Weeks Ahead AI so you never miss practical AI strategies designed specifically for blue collar business owners.
Leave a review if this episode helped you understand why your AI might be giving you bad answers!
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Are you a business owner frustrated with AI giving you made-up answers? You're not alone. In this episode of Weeks Ahead AI, we dive deep into why ChatGPT and other AI tools sometimes fail small business owners, and what you can do about it. Whether you run a construction company, HVAC business, plumbing operation, or any business, understanding the limitations of AI tools is crucial before you stake important business decisions on their output. In This Episode: Why AI models prioritize giving an answer over giving the right answer—and the real-world consequences for your businessThe "context window" problem explained: how your AI forgets critical information mid-conversationWhy one contractor nearly made costly financial decisions based on AI-generated "facts" that were completely fabricatedHow to test if your current AI tool is giving you biased or outdated answersThe simple "show your work" hack that catches AI mistakes before they cost you moneyWhich AI alternatives are outperforming ChatGPT for business analysis and planning Timestamps: [00:00] Introduction to Weeks Ahead AI – helping business owners save time and cut costs with AI [01:04] The "gateway drug" problem: Why most business owners start with ChatGPT and never explore alternatives [02:34] Terry's breakup story: Canceling ChatGPT after 18 months—and why it felt like a divorce [03:20] The comfort trap: "It already knows my stuff" and why that's keeping you stuck [05:00] When AI sounds like BS: Terry's first red flag that something was wrong [05:48] "Great idea!" syndrome: Why your AI agrees with everything (even your worst ideas) [07:04] The lawyer's warning: AI citing legal cases that never existed [08:00] Financial analysis disaster: How bad AI advice could have cost thousands [09:32] The spreadsheet nightmare: 3 days wasted trying to export 500 contacts [11:05] Context window explained: Why your AI "forgets" important details mid-conversation [12:14] The telephone game effect: How long chats corrupt your AI's memory [14:35] The "show your work" hack: Making AI prove its logic before you trust it [16:40] Memory bias problem: When AI applies wrong context to your current project [17:24] Behind the scenes: Why some AI companies throttle performance without telling you [18:18] Terry's current AI stack: Claude, Gemini, Grok, and Relay Hub [19:08] Four days without ChatGPT: Did Terry notice any difference? [20:40] ChatGPT introducing ads: What this means for users [21:29] Final takeaway: Stay weeks ahead by pressure-testing multiple AI models Links & Resources Mentioned: Episode 2 – Deep dive on exporting and transferring your ChatGPT data to other modelsClaude AIGoogle GeminiGrok – Available through X/TwitterRelay Hub – AI workflow automation platform we are building.If you're still relying on just one AI tool for your business decisions, it's time to pressure test your options. Try running the same business question through 2-3 different AI models and compare the answers. You might be surprised at the differences. Subscribe to Weeks Ahead AI so you never miss practical AI strategies designed specifically for blue collar business owners. Leave a review if this episode helped you understand why your AI might be giving you bad answers!