This conversation, with transit guru Stephanie Pollack, is one of my favorite conversations we’ve recorded on here. For one, I had a blast recording — Stephanie’s funny, and she’s got a killer Boston accent. For another, she explains some of the ideas I care about incredibly well — how well-intentioned regulations turn bad, how political pressures make simple things hard to pull off, why building in the real world is so hard. She taught me a huge amount about building transit. And she’s a great storyteller.

For context, Pollack was the deputy administrator of the Federal Highway Administration for the first half of the Biden admin. Before that, she served as the secretary of the Massachusetts Department of Transportation (DOT). And a while before that, before she was in the business of building stuff, she was an environmental activist who sued the the Massachusetts DOT for building stuff. We get into that evolution in her career here.

This conversation is one of a series of conversations over the coming months about transit: why it’s gotten so hard to build, who fights over it, and what it takes to build something people love.

We discuss:

(00:00) Introduction (00:54) Federal vs. State Transit Funding Structure (02:58) Transit vs. Highway Agency Operational Differences (04:58) Stephanie’s Career and Perspective Changes(10:39) The Massachusetts Big Dig Project (11:34) Cost Overruns and Project Estimates (17:04) Inflation in Infrastructure Projects(18:28) The Four Ps of Project Delays (23:50) NEPA and Environmental Review(34:19) The Green Line Extension Project (43:39) Project Redesign and Procurement Innovation(58:20) Advice for Secretary Duffy

Thanks to Sofia Scarlat and Emma Hilbert for their audio and transcript edits.

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