This episode goes somewhere we didn't plan, and we think that makes it one of our best yet.

We sat down with Jarah Euston, co-founder and CEO of WorkWhile, a fast-growing app-based staffing platform connecting 80 million frontline workers with flexible shift opportunities. Jarah grew up in Fresno working retail, got burnt out building software for tech people, and decided to build technology for workers instead. It's a compelling vision and a genuinely interesting conversation about flexibility, AI, and what the future of work could look like for hourly employees.

But after that conversation wrapped, we learned that WorkWhile had recently settled a second major lawsuit with the San Francisco City Attorney's office for misclassifying workers as independent contractors. So we spoke with David Chu, the San Francisco City Attorney, and asked for his side of the story.

What you'll hear in this episode is both interviews back to back. First, Jarah's perspective on building worker-centered technology, and then David's perspective on what happens when "flexibility" becomes a cover for avoiding worker protections.

Together, these two conversations raise a question that feels urgent right now: Is it possible to build a genuinely worker-centered future of work, one with flexibility, innovation, and fair treatment? Or are we just repackaging old inequities in new apps?

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