Builder's Jam
What started as a one-off is becoming a regular practice.
Last summer I pulled together a group of leaders who had something in common: they wanted to build something that mattered. Not another roadmap for someone else's vision. Something of their own. A few had side projects already in motion. Others had ideas they couldn't shake. The conversation was energizing, and the question came up right away: should we keep doing this?
I didn't have a good answer yet. So I sat with it.
Here's what I've landed on. Most of us aren't going to quit our jobs and start a company. That's not the move. But the itch to build something meaningful doesn't go away just because the timing isn't right for a startup. What's changed is that AI has made it possible to scratch that itch in ways that weren't available even a year ago. The tools are extraordinary now, and getting better fast. The leaders who learn to use them well won't just build better side projects. They'll transform how they lead, how their teams work, and how they think about what's possible.
I'm turning the Builder's Jam into a regular practice built around that idea. A small, committed group that meets twice a month to work real problems and hold each other accountable for actually building with these tools, not just talking about them.
If that sounds like your kind of room, read on for the details.
Todd Webb
How It Works
Each session runs two tracks:
The Leadership Challenge. One member brings a real, live problem they're navigating. An AI strategy presentation due to the board. A team restructure driven by new capabilities. A build-vs-buy decision that didn't exist six months ago. The group works it together. I facilitate and connect patterns across what I'm seeing in my coaching work and my own experimentation.
The Practice Readout. Two or three members share what they experimented with since last session. Maybe you prototyped an AI workflow for your engineering team. Maybe you spent Saturday morning building a side project that's been rattling around in your head for months. The project isn't the point. The learning is. What did you discover about working with these tools? What surprised you? The group reacts, asks questions, suggests next experiments.
Between sessions, the expectation is simple: build something with AI. Bring back what you learned.
Who This Is For
Two criteria. Both matter.
You're navigating AI at the organizational level. Your team, your product, or your strategy is being reshaped by what's possible now. The decisions are real and the stakes are real.
You're personally experimenting. You're not delegating AI to someone else and waiting for a report. You're using the tools yourself, building with them, forming your own judgment.
If both are true, you belong in this room.
If only the first is true, start with the second. Then come talk to me.
The Details
Format: Video sessions, twice monthly. 90 minutes each.
Group size: 8 to 12 people. Small enough for real conversation. Large enough for diverse perspective.
Commitment: One quarter. Six sessions over three months, plus the expectation that you're experimenting between them.
My role: Facilitator, pattern-matcher, practitioner. Thirty years of building and leading in tech. Active daily work with AI. The cross-cutting view from my coaching practice. I set the conditions and hold the standard.
Investment
$400/month, billed monthly. Three-month commitment to start.
Timeline
The first Builder's Jam kicks off in April 2026. I'm forming the group now.
12 spots. Once they're filled, enrollment closes.
If this is on your radar, don't wait too long to reach out. I'd rather have a conversation early than turn away the right person late.
Interested?
If this sounds like the right room for you, reach out. DM me on LinkedIn or email todd@toddwebb.co.
I'm looking for the right people, not the most people.