How I Stopped Working ‘In’ My Business and Started Working ‘On’ It with a 5-Person AI Board of Directors.
If you’re a founder or small business owner, you know the feeling.
You’re stuck.
You’re the chief strategist, lead salesperson, head of marketing, and customer service rep, all at once. The dream of “working on your business” feels like a cruel joke. You’re too busy working in it, just keeping the lights on.
I was there. I consistently felt that as a small business, I was missing that high-level, external view. Hiring a board of A-list consultants was out of the question.
So, I built one for (almost) free using AI.
I created a virtual “board of directors” populated by five experts: Steve Jobs (for vision), Alex Hormozi (for monetization), Seth Godin (for branding), Brené Brown (for leadership), and Simon Sinek (for purpose).
My goal was to create a “panel” that would challenge my assumptions, pressure-test my ideas, and give me the raw, unfiltered feedback I couldn’t get anywhere else.
I wrote a detailed script that instructed the AI to not just act as these personas, but to debate each other and work through a strict, multi-step process.
The results were, frankly, staggering.
👇Which led to the next phase: The Great AI Experiment — ChatGPT vs. Gemini.
Same script. Same instructions. Two very different outcomes.
I took the same script and ran it through both leading models to see how each would respond. Here’s what I found:
ChatGPT was methodical. It understood the task and immediately returned a list of structured, fact-finding questions about my business. It was like a diligent (but slightly cold) consultant gathering data.
Gemini was personal. Instead of one generic list, it returned individual, in-character questions from each board member.
- “Seth Godin” asked about my audience and “the smallest viable market.”
- “Alex Hormozi” drilled into my monetization and customer acquisition.
- “Steve Jobs” challenged my product’s core differentiation.
This was the “Aha!” moment. Gemini didn’t just execute the prompt; it embodied it. Both models provided high-value, specific insights with no misinterpretations, but Gemini’s approach felt like a real board discussion from the very first interaction.Straight away, this AI board “got” my business at a depth I had not expected. The experts were applying their knowledge properly to my specific challenges.
🎬The “Gems & Projects” Framework: From AI Insight to Team Action
The AI board was firing on all cylinders, giving me incredible feedback on strategy, branding, website terminology, and new areas of focus.
This created a new, high-quality problem: How do I, as a single owner, organize this flood of A-grade advice and make it actionable for my team?
The solution was a simple framework I call “Gems & Projects.”
- Gems: These are the core strategic insights, the “nuggets of wisdom,” that come directly from my AI board. A “Gem” might be a new way to position our brand from “Seth Godin” or a new monetization idea from “Alex Hormozi.”
- Projects: These are the specific, actionable tasks my team and I create to bring that “Gem” to life. A “Gem” is the “why” and the “what”; the “Project” is the “how” and the “when.”
This framework has become the bridge between high-level AI strategy and real-world business execution. It allows me to take the board’s advice, translate it, and start enabling my team to test their own ideas against the strategy.
⭐The Result: An On-Demand Board of Directors
As a business owner, I now have the ability to ask, drive topics, and build ideas with a world-class board whenever I want, wherever I want.
We are already looking into and acting upon the feedback we received. This process has given me clarity, focus, and—most importantly—a scalable way to finally start working on my business, not just in it.
This isn’t just a fun “AI trick.” It’s a real-world system for getting expensive, high-level strategic advice and, crucially, a framework for putting it into practice.
Are you a business owner who feels stuck? This method can give you the clarity you’re missing. I’m sharing this process because I believe it can help.
If you’re interested in getting the full script I used to create my AI board, get in touch!
Matt Wilkinson | matt.wilkinson@livelearningco.com
