- Business
- A commercial HVAC contractor, about $14 million in revenue, 60 people, 22 years old.
- The problem
- Revenue has been flat for two years. The owner still prices and presents every bid over $200,000 himself, and the two senior estimators have stopped trying to.
- Tried so far
- A sales hire that lasted eight months. A bonus plan nobody understood.
Casey Smith ยท Nashville
Founder, former tech executive, and advisor to CEOs since 2010.
I've started companies, run the commercial side of one that grew a lot, and lost one of my own. For the past three years I've facilitated founder groups for Hampton. Today my work comes down to two things: private roundtables where CEOs work on real problems together, and one on one advising for a small number of them.
By invitation. No packages, no pitch, nothing recorded.
What I'm for
Most CEOs don't need more ideas. They need a better question.
Someone outside the business who will ask the one nobody inside it can, and who has sat on the other side of enough of these decisions to know which answers hold up. Sometimes that's a strategy that needs rethinking. Sometimes it's an approach from another industry that nobody in yours has tried. And sometimes it's putting five other owners in the room, because they'll say what I can't.
A session, shown
One real problem in. One clear next step out.
Every roundtable runs the same way. Each CEO sends me the problem beforehand, the room works it, and nobody leaves without a commitment the others have heard.
- Hand the next three bids under $500,000 to the estimators, start to finish, and sit out the presentations.
- Write down what a bid has to show before it leaves the building, in one page, so they can be judged on it.
- Tell the two estimators, this week, that this is the plan and why.
An example of the shape, not a client. What's said in the room stays in the room.
Where this comes from
Built things, fixed things, lost one.
The advice is grounded in having done the work, not having read about it.
Linode
Nine years building the sales, marketing, business development and customer success teams at the cloud infrastructure company, from $18 million in annual recurring revenue to over $100 million. Akamai bought it in 2022.
Kroll
Grew the sales team for the data breach division and ran the relationships with AT&T, Google, Major League Baseball and the Department of Veterans Affairs.
HealthStream
Product manager at the newly public company, building the software, with Adobe, that Cleveland Clinic and HCA adopted.
My own companies
Co-founded two e-commerce startups and a media agency. Raised capital three times, sold twice, and went through one bankruptcy. The bankruptcy taught me more than the exits did.
Hampton
For the past three years I've facilitated founder groups for Hampton, the private community for founders. Up to nine people per group, running companies between $2 million and $50 million, meeting every month on whatever is hardest.
What founders say
In their words.
Casey helped me see the gap between how I thought I was leading and how my team was actually experiencing it. He has a rare ability to tell you the truth in a way that makes you better.
Sam ParrFounder, HamptonCasey has an uncanny ability to meet founders exactly where they are and move them forward. He coaches with clarity and kindness, pushing you without ego and always with genuine care. Having built and operated companies himself, his advice is grounded, practical, and immediately useful.
Blake HudelsonBoomPopWorking with Casey created immediate clarity and momentum. He helped me slow my thinking so the business could move faster, while also improving how I show up personally and mentally. His grounded, no-nonsense coaching consistently led to better decisions and real progress across every area of my life.
Jonathan NewarCaptainExperiences
Two ways to work together
A room of peers, or one on one.
Private CEO Roundtables
A half-day working session for four to six CEOs. Each person brings one real problem and the group works it. No presentations, no pitches, and nothing leaves the room.
How roundtables workAdvising
One on one, for no more than four CEOs at a time. We find what's holding the business flat, decide what to do about it, and if you want the work done rather than described, I stay and run it.
How advising worksIf something in your business has stopped working, I'd like to hear about it.
I read every message myself and reply within two business days.