Is This Working?!

Winning AI *Without* Losing The American Dream — Fmr US Commerce Secretary Gina Raimondo

April 29, 2026·49 min
Episode Description from the Publisher

AI is here. The layoffs have started. Does anyone have a plan? Gina Raimondo does. Two-term Governor of Rhode Island, former U.S. Commerce Secretary, the person who shepherded the CHIPS Act through Congress and personally negotiated chip exports with Chinese leadership. Harvard, Oxford, Yale Law before any of it. Her plan: a new grand bargain between government and business. Workforce training that's continuous, employer-led, and funded by outcomes. Wage insurance for workers retraining mid-career. Tax incentives that make it more expensive to abandon workers than to retrain them. The same urgency we've poured into chips and models, applied to the tens of millions of American jobs about to change. In this episode, Connor and Gina get into the plan, the warning ("do this wrong and we will have automated our decline"), why UBI is a cop-out, and her honest reply to whether she'd like the job of President in 2028. There's also a phrase she banned in her own cabinet that we can't in good conscience print here. Connor gets her to use it on camera. Stay for that. Chapters 00:00:00 Intro — The woman betting on America's AI future 00:01:16 Finding your Andy — Love, partnership, and non-negotiables 00:05:46 Faith, spirituality, and the work arena 00:08:01 The AI crisis nobody's preparing for 00:10:33 Winning AI without losing America 00:14:34 The grand bargain — Changing incentives for companies 00:17:55 More women in charge would help 00:20:16 The girl in the back seat with the racing stripe 00:22:39 Lightning round — Biden, bathrooms, and power perks 00:30:11 Grin-fucking and the yes-man problem 00:37:32 Presidential ambitions and the right moment 00:41:48 Conquering the self and the Msgina Special 00:48:03 Legacy, love, and what really matters IS THIS WORKING?! What if the most interesting thing about work isn't what we do—but what it does to us? Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway. Next episode dropping soon - subscribe to get notified!

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