Insights

Operator notes for middle-market AI.

Patterns, decisions, and judgment calls from three technology waves. Written for the CEOs and execs actually making AI decisions at $20M to $200M companies.

Middle-market strategy

Why middle-market AI strategies fail, five patterns I keep seeing

Most mid-market companies have more AI activity than they realize and less progress than they need. Here are the five patterns behind that gap.

May 11, 2026

min read

Middle-market strategy

The AI question for Long Island mid-market CEOs

Where LI mid-market AI decisions actually land, what they look like for a $40M logistics firm versus a $100M distributor, and what to do this quarter.

April 23, 2026

min read

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