In this episode of Weeks Ahead AI, we sit down with entrepreneur Jake Gannon to talk about how AI is changing what it means to start and scale a small business. From building companies with 60+ employees to launching a profitable venture solo using AI tools, Jake breaks down how founders can move faster, operate leaner, and eliminate unnecessary friction.

If you're a small business owner wondering where to start with AI or how to scale without bloating your payroll, this conversation is for you.

🔑 In This Episode

• Why founders must start with objectives and key results before using AI
• How AI replaces gaps traditionally filled by business partners
• The power of operational AI over marketing AI
• How Jake launched Polarity Parking in 6 months using ChatGPT
• Why discernment matters more than tool loyalty
• The biggest risk of ignoring AI in your industry

⏱️ Timestamps

00:00 – Welcome to Weeks Ahead AI
AI for business owners who want to save time, cut costs, and stay weeks ahead.

02:00 – Meet Jake Gannon
Founder of Polarity Parking and 1116. Previously scaled and exited an edtech startup.

04:00 – Where Business Owners Should Start with AI
Start with goals, objectives, and key results before jumping into tools.

06:30 – AI as a Replacement for Business Gaps
How AI accelerates learning curves and fills skill gaps traditionally handled by partners.

09:00 – Why ChatGPT Is Enough for Most Businesses
Why general AI tools are sufficient for 90% of small business use cases.

11:00 – Operations First, Revenue Second
Why improving operational consistency creates bigger long term gains than flashy marketing automation.

14:30 – From 62 Employees to Solo Founder
How Jake scaled his first company with a full team and built his next one lean using AI.

17:30 – The Fear Factor and AI Adoption
Why waiting for certainty is the biggest risk to your business.

20:00 – How Fast Can You Get Caught Up?
The AI learning curve is shorter than most people think.

23:00 – AI Is Not a Fad
Why AI adoption is like early cell phone adoption. Ignore it and get left behind.

26:00 – Inside Relay Hub
How centralized AI collaboration creates consistency across teams.

29:00 – The Story Behind Polarity Parking
From a cold walk in Chicago to a revenue generating AI built business in six months.

32:00 – Launch Faster with AI
How AI compresses product development timelines dramatically.

34:00 – Final Advice for Founders
If you’re afraid to try AI, that’s exactly why you should.

🔗 Links & Resources Mentioned

• 1116 Consulting
• Polarity Parking – Parking monetization platform
• Relay Hub – AI collaboration and workflow platform

🚀 Call to Action

If you want to build leaner, move faster, and make smarter decisions using AI, visit weeksahead.ai to learn more about Relay Hub and how to stay weeks ahead.

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 business
• The "context window" problem explained: how your AI forgets critical information mid-conversation
• Why one contractor nearly made costly financial decisions based on AI-generated "facts" that were completely fabricated
• How to test if your current AI tool is giving you biased or outdated answers
• The simple "show your work" hack that catches AI mistakes before they cost you money
• Which 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 models
• Claude AI
• Google Gemini
• Grok – Available through X/Twitter
• Relay 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!

Many businesses avoid budgeting because it feels complex, time-consuming, or intimidating.

In this episode of Weeks Ahead AI, the team walks through how business owners can use AI to build a complete annual budget using historical financials, without starting from a blank spreadsheet.

Throughout the episode, the team highlights why Claude performed best for this specific task, particularly when it comes to financial analysis, spreadsheet structure, and handling assumptions, while still acknowledging that different AI models excel at different jobs.

In This Episode

• Why many businesses still avoid annual budgeting
• Using Claude AI to turn past P&Ls into a working budget
• Why some AI models perform better at financial analysis
• Applying growth assumptions and seasonality
• Reviewing and correcting AI-generated budgets
• Running hiring and growth scenarios in real time

Episode Timeline

00:00 – Why budgeting gets delayed or skipped
Common reasons business owners avoid the process.

03:00 – Why January is not too late
Using last year’s numbers to move forward.

06:30 – Uploading historical financials into AI
How much data you actually need.

09:00 – Choosing the right AI for the job
Why Claude stood out for financial modeling.

12:30 – Building a full annual budget
Revenue, expenses, and staffing generated automatically.

15:00 – Monthly views, seasonality, and assumptions
How AI applies real-world business patterns.

18:00 – Reviewing assumptions and fixing errors
Why human oversight still matters.

21:00 – Scenario planning
Testing hires, marketing spend, and growth decisions.

25:30 – Why AI budgeting works now
How recent improvements changed what is possible.

29:00 – Managing multiple AI tools
The downside of subscription sprawl.

32:00 – Final takeaways
How to apply this approach in your business.

Tools and Resources Mentioned

• Claude for financial modeling and spreadsheet work
• Wispr Flow for voice-to-text prompting
• Excel for reviewing and adjusting budgets

If you have been putting off building a budget, this episode shows how AI can help you get it done faster and with more clarity. Subscribe to Weeks Ahead AI for practical, real-world AI use cases.