My Secret AI Strategy Weapon

As business owners, we get distracted by shiny objects…a lot!

Whether it's late at night reviewing a new strategy or early morning questioning a potential pivot, we have the tendency to chase ideas that keep us from executing what’s important.

I’ve built a bit of a cheat code with ChatGPT.

What if you could consult with Jeff Bezos, Steve Jobs, Warren Buffett, and other business icons whenever you needed them? That's exactly what I've created with my Board of Titans GPT, and it's transforming how I make decisions.

My Virtual Board of Directors

I've built a specialized GPT that channels the perspectives of six legendary business minds but asks them each to focus on one perspective they are famous for:

• Jeff Bezos examines everything through the lens of customer obsession and his famous "Day One" philosophy

• Steve Jobs focuses on product vision, user experience, and radical simplicity

• Frank Slootman zeros in on execution discipline and operational efficiency

• Warren Buffett analyzes business durability and economic moats

• Elon Musk challenges assumptions using first principles thinking

• John Malone evaluates financial structures and M&A opportunities

AI: The Ultimate Method Actor

Here's what's fascinating about AI - it's actually brilliant at taking on personas. Unlike humans who struggle to think outside their own experiences, AI can slide into different mental models with surprising authenticity.

You just need someone with enough track record on the internet for the model to know what their persona is.

My virtual boardroom doesn't just regurgitate quotes from these business titans - it actually processes problems through their distinct frameworks and worldviews. It's like having six different brains examining the same challenge.

And let's be honest, it's a lot cheaper than trying to get the real Bezos to join your board.

Seeing It In Action

Recently, I was wrestling with how to position OwnerRX. I started the company to transform business coaching and make it more accessible but as I went I saw a big opportunity in integrating AI into the operational layer of companies and not just the strategic.

So should we be more of a strategic coach or a full-blown COO for small business owners? I saw lots of pros and cons but was leaning towards staying true to my original vision. I tossed the question to my virtual board, and the response was illuminating:

Frank Slootman: Smart call. The "AI COO" vision is sexy, but operationally heavy. Coaching is a strategic wedge—it lets you move fast, ship light, and prove value with less integration complexity. Get tight on one thing: Which workflows create the most leverage for small business owners? Don't abstract. Pick 2–3 high-stakes workflows (e.g., pricing, positioning, client conversion) and own them completely.

Jeff Bezos: Exactly. Start with customer obsession, not infrastructure ambition. Coaching has lower technical overhead but still lets you deeply influence behavior. If you prove that users feel smarter, faster, and more in control within weeks, you earn trust—and then the right to automate more. The roadmap can bend toward COO-level depth once the user pulls you there.

Steve Jobs: Great. Now simplify. Coaching is not about content—it's about clarity and momentum. Design this to feel more like an intelligent guide than a dashboard. Kill complexity. Every prompt, every nudge, every insight—make it elegant and deeply felt. Build the experience of transformation, not just the scaffolding for it.

The full response continued with Warren Buffett focusing on recurring value, Elon Musk challenging me to reinvent the coaching model itself, and John Malone highlighting the cash conversion potential.

What struck me wasn't just the advice, but how distinctly each perspective approached the problem. Jobs zeroed in on user experience while Slootman focused on execution - exactly as they would in real life.

The Value of Cognitive Diversity

What makes this approach powerful is the tension between different worldviews. When Musk pushes for bold innovation while Buffett counsels caution, I'm forced to examine my assumptions more deeply.

It's like having six smart friends who never get tired of your business questions (unlike my actual friends who have instituted a strict "no business talk at dinner" policy after one too many product brainstorms).

This cognitive diversity helps me:

1. Identify blind spots in my thinking

2. Consider both short and long-term implications

3. Balance visionary goals with practical execution

4. Test my conviction on key strategic elements

You can try it out for yourself. The GPT is open to anyone with the link. You just need an OpenAI account. I can’t see your chats/results but I’d only ask one thing. If you like it or hate it shoot me a quick email with how it went.

I’m thinking about making more of these available before my full product launch later in the summer.

If you are interested in being part of the initial beta for OwnerRX, you can signup for the waitlist here.

A New Tool in Your Strategic Arsenal

This approach isn't meant to replace human advisors or your own judgment. Rather, it's a tool that helps expand your thinking and challenge your assumptions when you need it most.

And unlike your real board members, this one doesn't require equity, doesn't cancel last minute, and is perfectly happy to review your strategy at 3 AM when inspiration strikes.