What do you learn about yourself when you're alone in the mountains for a month with no plan and no one to impress? John Starkweather is the VP of Advertising at AT&T, but this conversation isn't really about advertising. It's about what happens when you get quiet enough to actually hear yourself, and what changes when you stop being so rigid about everything. This week, host Lauren Douglass sits down with John to talk about the breakthroughs that only come from long stretches in nature, why being flexible might be the hardest thing to learn, and what he realized about himself when his plan went completely off the rails. They get into the tension between AI and humanity, why real connections still matter, and how John's thinking about leadership shifted after he stopped trying to make everyone conform to him. John opens up about being his own worst enemy, what it means to actually listen, and why he introduces himself as a dad first, not by his job title. This is a conversation about slowing down, letting go of control, and figuring out what you actually want to leave behind.

Rachel Goldflam is building something from scratch, and she's doing it in a category that doesn't quite exist yet. As CMO of Sneex, a hybrid sneaker-heel brand, Rachel is figuring out how to normalize a product people have never seen before, get it on enough feet to reach a tipping point, and do it all with a scrappy team of four.

This week, host Lauren Douglass sits down with Rachel to talk about what it's really like to work at a founder-led startup after years at established fashion brands like Veronica Beard and Spanx. They dig into why fashion isn't vapid, how Rachel unlearned the rigid career rules she grew up with, and the feedback that changed everything when she was 22 and thought she had all the answers.

Rachel opens up about balancing motherhood with building a brand, why enthusiasm beats credentials every time, and what she learned from taking a risk she thought she wasn't "allowed" to take.

This is a conversation about scrappy ambition, learning what you don't want, and why sometimes the best move is the one that doesn't follow the rules.

Not all pivots are about moving up, some are about moving on. Dave Kersey is the Global Head of Media at SharkNinja, and his journey here includes a wrong phone number that changed everything, switching from architecture to media on a hunch, and learning the hard way when to walk away.

This week, host Lauren Douglass sits down with Dave to talk about career pivots, unexpected turns, and why he didn't leave a toxic work environment sooner.

Dave opens up about staying curious, building trust by being authentic all the time, and why no one cares about your career more than you do. This is a conversation about resilience, self-awareness, and learning when to protect your own worth.