Is This Working?!

When the VC Forbes once called “the most powerful woman in startups” says there's a way to make yourself AI-proof, it's worth listening. Ann Miura-Ko spent the last two decades deciding which founders are worth betting on. She wrote the first check into TaskRabbit, got in early on Lyft, and teaches entrepreneurship at Stanford. There are few people closer to what's actually happening in AI, and he...

Kristen Berman is one of the world's foremost experts on getting people to do what they say they want to do. She also routinely has a hard time following her own advice, which is precisely why she got into the field. Berman was on the founding team for behavioral economics at Google — a practice that now spans 26 teams across the company — and she founded Irrational Labs, a behavioral product desi...

Christina Stembel started Farmgirl Flowers in 2010 with $49,000 in her bank account, no college degree, and no VC funding. Sixteen years later, it’s a $35-million-a-year company. "We joke at Farmgirl that we're like cockroaches. You can't get rid of us. You just get stomped on, you just keep going." In this conversation, Christina and Connor talk about: the costs of building a company without the...

Most people in philanthropy wouldn't call themselves a "safety-net capitalist." Most people aren't Missy Narula. Missy’s made a career being comfortable in contradictions like “following your passion is overrated”—and she’s got the resume to prove it.  After Yale, Boston Consulting Group, and TPG, Missy walked away from all of it to start a company making phone holders that kept babies entertained...

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 tha...

Is there a version of you that feels unattainable? For David Gerard, it was becoming a full-time magician. So he did it slowly. Twelve years slowly. VP at Sequoia-backed startups during the day, performing shows at night, catching 3 AM flights from Kansas back to his job. The double life was the bridge. He built the thing he actually wanted one night at a time while keeping the safe life going, un...

84 counts of involuntary manslaughter. A worker dying every 90 days. An empty C-suite. That's what Patti Poppe signed up for when she became CEO of PG&E. In this episode, Patti gives a masterclass in crisis leadership — and pulls back the curtain on how she turned things around. She explains how she rebuilt the leadership team from scratch, why she hung up on every executive candidate who called P...

Matt Abrahams teaches Stanford’s Essentials of Strategic Communication, the university’s most popular communication course. His “Think Fast. Talk Smart” talks and podcast have earned over 80 million views and listens. And the first thing he told us is that the instinct to get it perfect is the exact thing making us worse. Not just at presentations. At everything. Meetings, hard conversations, even...

"Are you breathing?" Jin Ha's acting teacher used to interrupt class with that one question. It became a running joke among the students. It also changed how Jin Ha moves through the world. Jin Ha is a Korean American actor currently playing Aaron Burr in Hamilton on Broadway. He's also starred in Apple TV's Pachinko, worked opposite Steve Martin and Martin Short in Only Murders in the Building, w...

"Am I wasting some of the best years of my life?" Jan Sramek asked himself that question for years while working on one of the most audacious development projects in a generation: California Forever.  His plan: build an entirely new city on 100+ square miles of farmland in Solano County.  Not a housing development. Not a campus. A city, with schools, clinics, transit, and tens of thousands of home...

Ravi Kumar is one of the clearest voices on why AI will create more jobs than it replaces—which is surprising, because he's the CEO of a $35 billion company where machines already write a quarter of the code. He's not guessing. At Cognizant, the bottom 50% of his workers gained 37% productivity from AI. The top 50%? Only 17%. AI isn't replacing the bottom—it's lifting them up faster than anyone el...

How much can people actually change? According to renowned somatic coach Harley Frank, a whole lot more than you might think. Once a startup executive living with chronic anxiety and depression, Frank now works with leaders around the world using somatic body-based practices to help them reclaim choice, vitality, and presence. In this conversation, Harley and Connor explore why many of the traits...

Anthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis. In this conversation, recorded inside ACLU headquarters in New York, Ro...

Sarah Cooper went viral for lip-syncing Donald Trump on TikTok — and suddenly, the world knew her face. From there came a Netflix special, a memoir, acting alongside Jerry Seinfeld, and guest-hosting Jimmy Kimmel Live. But there was also everything people didn’t see: the disorientation of sudden fame, the pressure to keep performing, and the years of self-doubt that followed. In this conversation,...