Essays

• IT support is not IT leadership

  August 5, 2026

  Most companies buy IT support and assume leadership comes with it. It doesn't, and the gap costs more every year it stays open.

• Boston, Grand Rapids, Sarasota: the three places I work from

  July 27, 2026

  A job took me to Boston, a pandemic took me to a lake in northern Michigan, and family brought me home. How the year got split three ways, and why it works.

• Nobody owns your IT budget, and your vendors know it

  July 14, 2026

  Vendors price for the buyer in front of them. When no one on your side owns the technology spend, you are the easy account, and the renewals prove it.

• What running a company on AI actually looks like

  June 16, 2026

  My firms run on AI agents I built: ticket triage, research, reporting, onboarding. Here's what that's taught me about what to believe and what to ignore.

• When does a company actually need a CIO?

  May 11, 2026

  Not at a headcount number. The trigger is almost always one of four situations, and most owners recognize them only in hindsight.

← Home