I Built a Virtual Board of Advisors With AI — Here's What I Learned

I fired three advisors last month.

Not real ones - virtual ones. Steve Jobs was getting too aggressive. Peter Drucker kept overthinking simple decisions. And my virtual CFO? Turns out I'd trained him on outdated financial models.

Here's the thing: Running LaderaAI, we don't just build AI analysts for hospitality and retail. We use AI as our own board of advisors, customer proxies, product managers, even legal counsel.

We've created entire "team members" in Claude Projects, ChatGPT, and Gemini. Each one has a job description. Each one has context - our business plans, financial forecasts, customer insights, competitive intel. We maintain and update this context religiously, like you'd onboard real employees.

And here's what nobody tells you about this: It's both incredibly powerful and kind of absurd.

Powerful because I can test messaging against a virtual VP of a hotel group before I send it to a real one. I can pressure-test product decisions against someone who thinks like our CTO. I can get brutally honest feedback without the politics.

Absurd because I'm literally having arguments with AI about whether our pricing is too aggressive.

But here's what I've learned: The quality of your AI team member is directly proportional to how much you maintain their context. Garbage in, garbage out. Stale context? Stale advice. This isn't "set and forget." This is real work.

Which brings me to something I find darkly funny:

We built LaderaAI to be the AI Analyst that doesn't require all this maintenance. It connects to your systems, understands hospitality and retail natively, and stays current automatically. We built what I wish existed for running strategy - but focused on operations.

My challenge to you for 2026: Build yourself one virtual advisor. Give them a real job description. Feed them real context. See what happens.

You'll either think I'm crazy, or you'll build five more.

Either way, tell me what you learn.