Podcast · Season One

Before You Bet.

A field record of AI transformation in law. How the leading law firms are actually doing AI transformation — hosted by Helen Fan.

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Before You Bet, Season One — hosted by Helen Fan, with guests from Pillsbury, Dentons, Cooley, Gibson Dunn, K&L Gates, Weil, Bird & Bird and General Legal
Why this podcast

Today I'm starting my podcast Before You Bet, a field record of AI transformation in law. Season 1 is 10 AI leaders at leading law firms.

There is a lot of noise right now: legal tech companies, firms, press releases. Meanwhile the real moves happen every day: large firms are building AI teams at a pace nobody predicted two years ago, and the money behind it has gone from a line item to a strategic bet, some of it down to buying their own hardware to run models in house.

What we don't have is any systematic account of what is actually going on behind those announcements. What the reasoning was. What got tried and walked back. What it took.

The demand is real on both sides. In-house leaders want to know how the firms they hire are investing in AI. Mid-size and small firms want to know what the leading law firms are doing before they commit their own money.

This is also how I learn. My hope is that by the end of the 10 episodes, the series adds up to a Playbook for Law Firm AI Transformation, built on my Legal AI Value Stack.

I asked a few friends whether this was worth doing. The response was far warmer than I expected. 8 guests are confirmed, 2 more in process, episodes running October through January.

Confirmed so far

  • Oz BenamramChief AI Officer, Pillsbury Winthrop Shaw Pittman
  • Elliott PortnoyGlobal CEO Emeritus, Dentons
  • David WangChief Innovation Officer, Cooley
  • Meredith Williams-RangeChief Legal Operations Officer, Gibson Dunn
  • Brendan Gutierrez McDonnellM&A Partner and Founder of the AI Solutions Group, K&L Gates
  • Andrew SimonChief AI & Innovation Officer, Weil, Gotshal & Manges
  • Shahin BaghaeiPartner, Bird & Bird
  • Liz PaisnerManaging Partner, General Legal (YC26)

Episode 1 is with my old friend Oz, out this week.