We just got back from our first workshop style retreat in Sundance, Utah.
We brought ~30 members together for two days of deep work.
The focus: lead generation and deal management using AI native tools.
After two packed days, one insight kept coming back up.
AI handles the lower value tasks so humans can focus on the higher value work.
Last year, I had 539 one-on-one calls with founders and executives of boutique professional services firms. From QBRs to onboardings to sales conversations and diagnostic readouts. After that many conversations, one lesson stands out above the rest: the firms that thrived in 2025 were bold, and the firms that struggled played it safe.
At the start of 2025, I made a simple New Year’s resolution: complete a marathon.
Up until then, most of my training had been for baseball or CrossFit. Strength mattered more than endurance. Running had never been my thing. But, I wanted to see what would happen if I set a big goal and followed through.
Dear Collective 54 Subscribers, In the dynamic world of small service firms, where scaling is the ultimate goal, it’s essential to know what business you’re truly in. Are you the “Sage on the Stage,” orchestrating a multitude of employees to provide assistance, or are you the “Guide on the Side,” offering unique wisdom and advice to your clients? Understanding your place in the wisdom industry can be the key to unlocking your firm’s true potential.
In professional services, it’s not uncommon to hear founders proudly declare, “We are the only firm that does (insert blank).” While this statement may seem like a badge of honor, it could actually be a red flag. In this edition of Collective 54 Insights, we’ll dive into why having lots of competition is a good thing for boutique professional service firms, and why being the only firm that does what it does is a risky proposition.
Embarking on the journey to sell your business is a monumental decision, especially for small to lower-middle market business owners. It’s not just a transaction; it’s a pivotal moment that can shape the future of what you’ve built. However, amidst the excitement and potential for growth, there lurks a critical challenge that could derail your plans: counterparty risk, particularly the risk stemming from financing contingencies.