A couple of years ago, I had a dinner conversation that changed my business.
I was talking to a successful Austin investor — the kind of guy who has stakes in 20+ companies, attends board meetings, advises founders. Smart, busy, very little time for anything that isn't high-signal.
He knew about my AI program. But he hadn't gone through it.
“Have you ever considered doing this in person?” he asked.
“No,” I said. “But I've been thinking about it.”
That was the start of my in-person workshop business. But it also set up an insight I didn't fully appreciate until I'd run dozens of workshops: a surprising number of the people in the room weren't founders or operators trying to automate their email. They were investors.
The Unexpected Attendee
Fund managers. Angels with portfolios. People sitting on the boards of 10, 15, 20 companies.
Their goal wasn't to build an AI agent. It wasn't to set up a workflow or learn to use ChatGPT for their own work — though some of that happened too.
Their goal was narrower and more specific: they wanted to be able to have intelligent conversations with their CEOs about AI.
Not just listen and nod. Actually know enough to ask the right questions. “Have you considered doing X with your customer intake data?” “Why haven't you looked at automating that part of the proposal process?” Real, informed questions from someone who understands what's possible.
The AI Literacy Gap
When most people talk about AI literacy, they're talking about employees learning to use AI tools in their daily work. That's real and important.
But there's another literacy gap that gets less attention: the boardroom gap.
An investor who can't evaluate their portfolio companies' AI strategy is flying blind. They can't tell if a CEO is genuinely ahead of the curve or just using the right buzzwords in their Q4 deck. They can't ask follow-up questions that reveal whether an “AI initiative” is actually moving the needle or just a slide.
That gap has consequences. Not just for investors, but for the companies they fund.
The way I think about AI fluency, there are three levels. The first is AI Assisted — using AI to help with individual tasks (drafting emails, summarizing documents, doing research). The second is AI Workflows — building repeatable automations that run without you having to prompt each step. The third is Building Agents — multi-step systems that handle whole chunks of work end-to-end.
Most investors don't need to reach level three. But they absolutely need to understand what each level looks like in practice, what it can and can't do, and how to spot whether their CEOs are actually deploying it — or pretending to.
Level one literacy, paired with a clear view of what the higher levels look like, is enough to make a real difference in a board meeting.
What One Day Does That One Hour a Week Won't
The investor from that first dinner conversation told me directly: he wasn't going to spend an hour a week on an online course. Too many competing priorities. The commitment was easy to de-prioritize.
But a full day? That he'd do.
I hear this consistently from investors and executives who come to my workshops. The one-day format works for them in a way that async courses don't — not because they're lazy, but because their bandwidth for low-urgency learning is basically zero. They need the immersion. They need the live demos. They need to see something built in front of them, ask questions in real time, and walk out of the room with the mental model already loaded.
There's something about watching someone build an AI agent live — from nothing, in front of you, solving a problem you recognize — that a video recording just doesn't replicate. Michael Housman, who's done 50+ enterprise AI talks, put it well: “It blows people's minds in a way that screenshots and videos never can. Even ten years later, that hasn't changed.”
He's right. I've seen it in every single workshop.
Why This Matters Now
AI is moving fast enough that the gap between people who understand it and people who don't is widening every month. The executives and investors who take one day to get up to speed now will be asking much better questions in board meetings by Q3. The ones who keep saying “I'll get to it eventually” are slowly losing the ability to evaluate what their teams are telling them.
This isn't about becoming a technical expert. It's about having enough of a foundation to exercise judgment. To smell when something's off. To know when a CEO is ahead of the market versus behind it.
That's what AI literacy actually looks like for the people running the capital.
If you're an investor, fund manager, or executive who wants to get up to speed on AI without a six-week course — my next workshop is designed exactly for that. Reply to this post or DM me directly.
