This week the hosts sit down with Saikat Chakrabarti, who was Stripe’s second engineer and later worked on the Bernie Sanders campaign and served as Alexandria Ocasio-Cortez’s first Chief of Staff. He is now running for California’s 11th House district, which represents San Francisco, against Nancy Pelosi and Scott Wiener. Pelosi has held this seat for nearly four decades.

They talk about why Saikat left tech and how to encourage more young and ambitious people to get involved in politics. Saikat shares his vision for a Democratic Party that supports candidates that are builders from different backgrounds and do not take donor money.

The conversation dives into key policy issues, including:

• Public power in SF, and why the city has a legal right to replace PG&E.
• The housing crisis, and what meaningful affordability solutions could look like.
• Homelessness, and the potential for models that blend harm reduction, real treatment, and clearer systems of enforcement.

They also discuss AI regulation. Saikat argues that focusing only on catastrophic AGI risk overlooks the more immediate concern: concentrated economic power and widespread job displacement.

The episode ends with a fun speed round where Saikat responds to his haters including YC CEO Garry Tan.

You can learn more about this platform at https://www.saikat.us/en.

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00:00 Intro

00:34 From Stripe’s second engineer to a bid for Congress

05:31 DOGE

09:12 Changing the Democratic Party

18:45 Why PG&E shouldn’t exist31:26 The free market and when it fails

33:28 How Congressional Reps influence city budgets

39:33 Reviewing Daniel Lurie’s first year as mayor

42:33 The homelessness problem in SF

48:18 AI regulation

52:11 Responding to the haters

55:32 AOC running for president in 2028

58:07 How to get involved with Saikat’s campaign