The AI conversation you’re not getting anywhere else
Every leader I talk to is getting the same message. AI will change everything. Move fast. Don’t get left behind. The pitches are relentless, the demos are slick, and almost none of them tell you what actually happens when you put this in front of real data, real processes, and real people.
That’s the conversation this group exists to have.
Nobody here is against AI. We’re against the hype, the chaos, and the pressure to move faster than our companies can actually think. As one member put it, the technology isn’t the risk. The absence of a plan for it is. When you’re the person accountable for the number, you can’t afford to guess. You need to hear what’s working, what broke, and what was a waste of money, from people who have no reason to sell you anything.
What the group actually is
The AI Peer Group is a small, invite-only circle of sales and revenue leaders, executives, and owner-operators who meet regularly to talk honestly about AI in practice. Sessions are short and focused, about 45 minutes, virtual, and built around real conversation instead of slides
I host and keep things moving, but the value is in the room, not in me. Everyone arrives with something they’re wrestling with, and everyone leaves with a few things they hadn’t considered.
A few things this group is not. There are no vendors in the room selling tools. There are no decks. Nobody is pitching you, including me. And what’s said in the room stays in the room, which is exactly why the highlights below are anonymized. Discretion is part of the deal.
What we actually talk about
These are real moments from recent sessions, shared with names removed. They’ll give you a feel for the altitude of the conversation.
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AI whiplash is real. An IT services leader described companies spending serious money on AI with no definitions, no rules of engagement, and no way to measure whether it worked. The risk isn’t the technology. It’s the lack of a plan for it.
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The vendor noise is exhausting. An agency owner is getting pitched narrow, single-purpose tools every week. Stitching together a hundred of them that don’t talk to each other isn’t a strategy.
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The “build it yourself” temptation. A software leader had a prospect tell him they’d skip the formal process and just vibe-code their own system. His response stuck with me. If your expense app breaks, who cares. If the system that runs your business stops, your business stops.
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The pricing problem nobody has solved. A services leader named the tension out loud. If AI lets you deliver in a tenth of the time but you still bill by the hour, you just cut your own revenue.
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The unglamorous truth. This one’s mine. AI on top of bad data just helps you make bad decisions faster. The cleanup work everyone wants to skip is the work that makes everything else pay off.
The through-line across every session is the same. The fear phase is fading, and what’s replacing it is messier and far more useful. Honest questions about data, governance, pricing, and what’s actually worth doing.
Who it’s for
This group is a fit if you carry the number or own the outcome. Sales and revenue leaders. Executives. Owner-operators running services, software, or agency businesses. People who are past the hype and want a straight answer.
It’s not a fit if you’re here to sell something, or if you’re looking for a webinar to watch passively. This is a working conversation among peers, and we keep it small on purpose.
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Request to join
Membership is by request, and we vet new members to protect the quality of the room. If that sounds like the kind of conversation you’ve been missing, ask to join below. I read every request personally.
Not sure yet? Reading the blog is a good place to get a feel for how we think.