As boutique professional services owners, most of us are trying multiple ways to profitably grow our business. For organic growth, this includes investing in AI, improving sales effectiveness, or cutting unnecessary costs.
If your outcome-based pricing proposal hit my inbox, it would likely get rejected. Not because the concept is wrong, but because the attribution is lazy. Here’s the good news: I’m going to tell you what folks like me need to see to accept these proposals. I’m having these conversations right now with clients.
As professional services founders, we all understand that in the course of founding and scaling a business, there are times when an infusion of cash becomes helpful, if not crucial: funding a hiring surge, acquiring a competitor or bridging a gap before a large retainer kicks in, just to name a few examples.
I’m getting whiplash from my professional services network right now.
Every conversation is about AI. Every conference session is about AI. Every LinkedIn post is about “revolutionizing your firm with artificial intelligence.”
Greg Alexander is right. The founder bottleneck is real, it kills firms, and if you’re still the one doing everything three years after you should have delegated it — that’s on you. I’ve read the book. I believe the thesis. I’ve spent years pulling myself out of day-to-day client work, building a team, and trusting the people I hired to do the job I hired them for. And yet. Here I am, personally involved in three active engagements right now. Before you close the tab — hear me out.
As pilots and FAA professionals we have friends that fly the Pitts S-1, one of the most legendary aerobatic biplanes ever built. When asked what it’s like to fly the Pitts, those pilots don’t start the thrill of inverted flight or the rush of a perfect aerobatic maneuver. they often say something I related to: “It’s not a fun airplane to fly. It’s always trying to kill you.”
AI is reshaping professional services faster than anyone expected. The biggest consulting firms are using it to rethink how they develop strategy for clients. They’re changing their business models, restructuring how they deliver work, and planning for a very different future.
If you hand AI strategy to a manager, you’ll get automation. Not transformation.
Most founders are approaching AI the same way they approached their CRM rollout, their marketing automation platform, and their new reporting dashboard. They find a smart manager, hand them the tools, and say: “Go find some efficiency.” Wrong move.
Last month at our Sundance retreat, I watched a room full of founders have the same realization at the same time. We had been talking about lead generation. Specifically, why outbound feels so broken for boutique professional services firms. The room was nodding. Everyone had tried some version of the same playbook: buy a list, write a template, blast it out, hope for replies.
When Collective 54 launched, we couldn’t host in-person events. The pandemic made sure of that.
So we built everything virtually. And it worked. But something was missing.
In 2023, we hosted our first in-person gathering for the full membership. We called it the Founders Summit. It’s now in its fourth year, renamed the Member Reunion, and it draws 200 members.