A half-day working session for four to six CEOs, built around the problems you can't raise at the office.
Running a company is lonelier than it looks. Your team can't push back without consequences. Your board, if you have one, sees a slide. Your spouse has heard enough. The people best placed to tell you the truth about your business are other owners who have been through their own version of it. I put them in a room together and run the conversation.
What it is
Four to six CEOs and owners, chosen so nobody competes with anybody. One room, about three hours. Each person brings one real problem: the thing that's flat, stuck, or quietly getting worse. The group works it. I ask the questions, keep it honest, and make sure every person leaves with something specific to do next.
What it isn't
It isn't a networking event, a seminar, or a pitch. Nobody presents. Nobody sells. I don't record it and I don't use it for marketing. What's said in the room stays in the room, and everyone agrees to that before they sit down.
How a session runs
- Before. Each participant sends me a short description of their business and the one problem they want to work on. I read everything and come with questions.
- In the room. Each CEO gets the floor for their problem. The group asks, challenges, and offers what has worked for them. I keep it moving and keep it on the actual problem rather than the comfortable one.
- Leaving. Every participant leaves with a clear next step for the next 30 days, in their own words, that the room has heard them commit to.
The first session: Breaking Through
What's keeping your business from the next level? Most owners have a theory. The point of the session is to find out whether the theory is right. The questions we work through:
- What is actually stopping the business from growing, as opposed to what everyone says is stopping it?
- Are you solving the right problem, or the one you know how to solve?
- Which assumption was true five years ago and may not be true now?
- What has worked in another business or another industry that nobody in yours has tried?
- What will you do differently in the next 30 days?
Who it's for
Owners and CEOs of established businesses, most of them between $2 million and $50 million in revenue, who want a candid conversation with peers and will give one in return. If you'd rather listen than be questioned, this isn't the right room.
Who runs it
I'm Casey Smith. I'm a founder, a former tech executive, and an advisor to CEOs since 2010. At Linode I built the commercial teams while annual recurring revenue grew from $18 million to over $100 million; Akamai bought the company in 2022. Before that I held leadership roles at Kroll and HealthStream, and I've co-founded companies of my own, two of which sold and one of which went bankrupt. For the past three years I've facilitated founder groups for Hampton, the private community for founders, where up to nine owners at a time work through their hardest problems every month. The roundtables are that experience, in a shorter form, for people who aren't in Hampton.
Taking part
Roundtables are by invitation, usually through someone who knows both you and me. If you'd like to be considered for a seat, tell me a little about your business and what you'd bring to the room.