StephenOldfield

The Oldfield Broadsheet — Est. 2026

Systems — public, digital, personal

I build systems

A transit authority · an AI second brain · a business · a homestead

Administrator & CEO of a regional transit authority and statewide NEMT brokerage. Builder of an AI second brain, a business, and a homestead.

Get in touch
Portrait · Stephen OldfieldPhotograph forthcoming — the monogram stands in
01

At a glance

  • Role

    Administrator & CEO

    Regional transit authority · statewide NEMT brokerage

  • Ventures

    Common Ground Grow Co.

    Founder — plus an AI second brain and a working homestead

  • Latest post

    How I built an AI second brain

    Aug 11, 2026

  • Current focus

    Technology modernization at the authority · the fall garden

03

Latest writing

All writing →
  • Aug 11, 2026

    How I built an AI second brain

    What a decade of operations taught me about paperwork, and why I finally made the paperwork run itself.

    Continued on the writing page

  • Aug 11, 2026

    Systems, not silos

    The operating thesis I brought from a research firm's production floor to a transit authority's corner office.

    Continued on the writing page

  • Aug 11, 2026

    Teaching self-reliance

    What I actually want my sons to inherit — and why it isn't money.

    Continued on the writing page