Issie Lapowsky

Freelancer

Issie Lapowsky is a reporter-in-residence at Omidyar Network.

Latest

Inside the Odd—and Oddly Human—Work of Teaching AI to Talk

Inside the Odd—and Oddly Human—Work of Teaching AI to Talk

They vent, confess and role-play with strangers, all to help machines learn how to sound human.

March 30, 2026

March 30, 2026

Inside the Odd—and Oddly Human—Work of Teaching AI to Talk

They vent, confess and role-play with strangers, all to help machines learn how to sound human.

Inside the Odd—and Oddly Human—Work of Teaching AI to Talk

February 26, 2026

February 26, 2026

Claude Code and the Great Productivity Panic of 2026

AI coding agents promised to make software development easier. Instead they’ve kicked off a high-pressure race to build at any cost.

Claude Code and the Great Productivity Panic of 2026

January 21, 2026

January 21, 2026

AI Becomes the Tone Police for White-Collar Workers

Workers are turning to chatbots to help them get through difficult conversations with their colleagues and business partners.

AI Becomes the Tone Police for White-Collar Workers

December 15, 2025

December 15, 2025

On the Internet, Nobody Knows You’re a Human

Deepfakes and chatbots are now good enough that many web users don’t trust they are interacting with real people.

On the Internet, Nobody Knows You’re a Human

May 8, 2025

May 8, 2025

Maybe AI Slop Is Killing the Internet, After All

The assertion that bots are choking off human life online has never seemed more true.

Maybe AI Slop Is Killing the Internet, After All