September 23, 2026

Richard R. Waterfield Speaks at Columbia Business School Richard R. Waterfield, co-chairman and CEO of Waterfield Enterprises, returned to Columbia University for a panel discussion exploring the relationship between faith, finance and human flourishing. A 1994 Columbia economics graduate, Waterfield drew on his Indiana upbringing and career in finance and business leadership to discuss why…

Anthropic just passed OpenAI

By Damian Mathews & The Last Mile Team Ask a stranger to name an AI company and you’ll get one answer. ChatGPT. Over a billion people use it every month. It’s a verb now, the Kleenex of artificial intelligence. Which is what makes last week’s news so strange. Anthropic, the AI company many people outside the…

Stop building AI like it’s 2022

By Kerry Robinson Hi, it’s Kerry here standing in for Damian, who will hopefully return from his travels energized and eager to host The Last Mile next week 😎 Meanwhile I hosted a LinkedIn live this week with my co-conspirators Michael (Fish) Fisher, and Dan Aslet where we revisited the idea of the AI first…

Solving AI’s Last‑Mile Problem

By Kerry Robinson Hi, it’s Kerry here again, standing in for Damian, who’s still road tripping around the US of A 😎 Meanwhile, in the AtCoder World Tour Finals 2025 in Tokyo, Polish superstar Przemysław “Psyho” Dębiak edged out an AI coding agent that OpenAI entered into the competition. He shared on social media platform, X:  “Humanity…

Unlock 127% Better Learning

By Kerry Robinson Hi, it’s Kerry here, back to host The Last Mile for a few weeks while Damian takes a well-earned break after graduating from college. ChatGPT will be nearly three years old when the next college year starts this fall, so Damian is probably one of the last cohort of students to start…

Treat AI like a tool and it’ll act like one

By Kerry Robinson Talk shapes output. Most people treat prompting like a vending machine: press button, get snack. But LLMs aren’t mechanical. They’re behavioral – they pick up on tone, structure, and phrasing. Kerry Robinson put it well in his recent Substack post on why we often say please and thank you to AI, and why that’s…

When Good AI Gives You Bad Numbers

By Kerry Robinson What gets measured gets managed. But what if you’re measuring (and managing) the wrong thing? For the last two decades, customer service has been ruled by metrics like average handle time, tickets closed, and first-call resolution. Those numbers showed up in dashboards. Those dashboards shaped behavior. But now those numbers are starting…

Waterfield AI | Autonomous CX

By Kerry Robinson I used to think the best customer service was fast, friendly, and easy. Now I’m not so sure. In the past year, I’ve seen a different kind of gold standard quietly emerging. No service at all. Your refund gets issued before you ask. Your order re-routes before you notice a delay. Your…

Waterfield AI | Teaching Robots To Talk

By Kerry Robinson Welcome to the first edition of ‘The Last Mile’ 😁 This is the follow up to our Teaching Robots to Talk series, because robots learned to talk, now we need to put them to work! That’s a bigger challenge that cuts cost across AI, CX, and IT, but we’ve got you covered:…