Administrator & CEO of a regional transit authority and statewide NEMT brokerage. Builder of an AI second brain, a business, and a homestead.https://stephenoldfield.com/https://stephenoldfield.com/writing/how-i-built-an-ai-second-brain/https://stephenoldfield.com/writing/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.Tue, 11 Aug 2026 00:00:00 GMThttps://stephenoldfield.com/writing/systems-not-silos/https://stephenoldfield.com/writing/systems-not-silos/The operating thesis I brought from a research firm's production floor to a transit authority's corner office.Tue, 11 Aug 2026 00:00:00 GMThttps://stephenoldfield.com/writing/teaching-self-reliance/https://stephenoldfield.com/writing/teaching-self-reliance/What I actually want my sons to inherit — and why it isn't money.Tue, 11 Aug 2026 00:00:00 GMT