There is a lot of bad press around AI. Many firms are reducing headcount because of AI. What I see is amazing things people around me are doing as a result of AI. Not long ago, building a software application meant hiring developers, writing requirements documents, managing timelines, and spending money you may or may not have had. If you had a great idea but weren’t technical, you either found someone technical to help with the idea or you shelved it.
You built a great business. You’re ready to sell, and you know how businesses are valued:
Valuation = EBITDA x Multiple
A Snake Oil Salesman is someone who sells something they claim works but doesn’t. They do it with a lot of confident, flashy persuasion to distract from the lack of substance.
Why “grow without hiring” is the most important sentence a boutique founder will write in 2026.
Most boutique professional services founders think they have one AI strategy to pick.
They are wrong. There are two. They look similar. They produce wildly different firms.
For many founders and owners of professional services firms, the hardest strategic question isn’t how to grow—it’s how to transition without undoing what took decades to build.What happens to the company when you step back? What happens to the people who helped build it? And what happens to the culture, independence, and values you care deeply about?
There’s a list of roles in every boutique firm that exist on paper but rarely get done well. Account management. Service design. Marketing. Sales management. Every founder has the list.
It wasn’t because founders didn’t care. It was because the math never worked. And the math just changed.
Two years into the AI era, many boutique professional services founders I talk to are stuck. The initiative isn’t dead, but it isn’t really moving either. There’s activity. Meetings, demos, vendor calls, but very little has actually shipped. No new economics on the P&L. No real change in how the firm operates. No buyer would look at the business and call it AI-native.
Like many Founders, I’ve spent hundreds of hours researching, using, testing, and talking to my peers about AI the last 12-18 months.
In those hundreds of hours, I’ve come to notice one fork in the road that’s quickly become critical in whether AI is creating value or destroying it: AI is either being used to cut costs, or it’s being used to compound expertise.
For founders of growing firms, retreats like these may feel familiar. For most COOs and certainly for me, they do not. I have an unusual seat at your table and sit in your conversations as a bit of an outsider.
After three retreats, I have something to tell you.
I have attended three Collective 54 retreats in the last 7 months. I am not a founder – I am the COO of a boutique professional services firm.
For founders of growing firms, retreats like these may feel familiar. For most COOs and certainly for me, they do not. I have an unusual seat at your table and sit in your conversations as a bit of an outsider.
After three retreats, I have something to tell you.
My partners and I have built Rootstrap over fifteen years. In that time, the firm has passed through many distinct inflection points.
These are the moments when what has been working stops working — sometimes loudly, more often quietly. Revenue plateaus. The leadership team that ran a $5M firm breaks under a $10M load. The meeting cadence designed for thirty employees suffocates a team of a hundred.
