How a Lunch in Cleveland Turned Into a Vegas Keynote

A few weeks ago I drove over to DigiMarCon Great Lakes in Cleveland. I wasn’t there to speak — my badge said attendee, and I mostly wanted to soak up two days of conversations about where AI and marketing are actually heading.

What I didn’t expect was how much of my own time I’d spend showing people the thing I’m a little obsessed with right now: the Obsidian “second brain” I’ve built to run my work. A few folks asked what was on my screen, one question turned into another, and before long I was walking people through how I wire Obsidian together with AI agents to capture, connect, and actually use everything I read and do.

One of those conversations happened over lunch — with Dennis Yu. (And I’ll say it plainly: DigiMarCon has the best conference food I’ve come across, which made it very easy to keep talking.) We got deep into how I use Claude day to day — not the demo version of AI, but the unglamorous, real workflow: agents doing the busywork, me staying the one who decides.

By the end of lunch, Dennis asked if I’d bring it to a bigger stage.

That stage is DigiMarCon World in Las Vegas this November, where I’ll be sharing how I actually use Claude — the system, the habits, and the parts that translate to anyone trying to do more with a small team and a lot of AI.

So that’s the plan. Funny how the best opportunities tend to show up sideways — over lunch, mid-sentence, when you’re just being honest about the thing you can’t stop building.

What’s next

Between now and Vegas I’ll be writing more about AI, marketing, and the future of healthcare — and starting a few conversations I’m genuinely excited about. If any of that is your world too, come say hi.