I tell founders what to rent, what to own, and what to ignore in this era of AI.

The judgment comes from building at both ends. I designed the technical and systems architecture behind what became Oracle Transportation Management and led its datacenter deployments; most of the Fortune 500 runs its logistics on that platform. I founded, grew, and exited an 8-figure global consulting and hosting company serving Fortune 100 and 500 enterprises. And across three and a half recent months, I held 80 recorded conversations with founders working through exactly these decisions.

I work best with founders of 5-to-50-person companies, where every relationship is load-bearing. Be prepared: I'm straightforward and give honest feedback.

For deeper work, start at chrisplough.com/ai.