Artificial intelligence strategy, implementation, and readiness for lower middle market business owners.
ChatGPT for Business Owners: What It Actually Does and What It Can’t Business owners are using ChatGPT. The ones doing it well are getting real leverage. The ones doing it poorly are generating content that sounds like everyone else’s, wondering why it doesn’t move the needle on anything that actually matters. Here’s the honest breakdown:…
The Operator’s AI Roundup — June 2026 The AI Tools Business Owners Are Actually Using Right Now — and What Changed This Month Every month I publish what I’m seeing on the ground. What’s working in our own firm. What owners I’m talking to are actually using. What changed. What didn’t matter as much as…
AI for Professional Services Firms How Professional Services Firms Use AI to Scale Without Hiring Accounting firms, law practices, consulting groups, marketing agencies, staffing companies — the ceiling in professional services isn’t always market demand. It’s often that scaling requires adding people, and adding people requires the owner to manage more of everything. The professional…
AI for Construction Companies How Construction Companies Are Using AI to Build More and Manage Less Construction is one of the most complex businesses to run. It’s also one of the most resistant to the kind of systemization that makes a business worth more. That gap is the opportunity. Construction companies don’t fail because the…
AI for Trades and HVAC How HVAC and Trade Businesses Can Use AI to Run Without the Owner Most HVAC and trade businesses run the same way they’ve always run: the owner is the system. Here’s how to change that without changing what makes your business good. Talk to any HVAC company owner doing $3M…
Last updated: June 2026 We built the Icon AI Assessment because we needed it ourselves. Before we started offering it to clients, we ran it on our own firm. What we found was uncomfortable enough that we knew we were onto something real. In the months since, we’ve taken the same assessment into businesses ranging…
Last updated: June 2026 Buyers are getting more sophisticated. The ones writing checks above 4x EBITDA on lower middle-market deals aren’t just looking at revenue trends and customer concentration. They’re asking a different question now: can this business explain itself? In the last 24 months, we’ve watched due diligence shift. The financial review hasn’t changed….
ICON AI: OPERATOR’S PLAYBOOK Eighteen months ago, we started building something that had no clear end state. We knew we wanted to run Icon Business Advisors the way a company ten times our size would run, with institutional-quality processes, fast turnaround on complex deliverables, and systematic intelligence that compounds over time. We just didn’t know…
Last updated: June 2026 Most business owners think sellability is about revenue. The more you make, the more you’re worth. And to a point, that’s true. But the owners who get the best multiples, the cleanest closings, and the most competitive buyer processes aren’t just the ones with the highest top lines. They’re the ones…