From Dropout to Billionaire: Lucy Guo’s Success

Retired four-star general Stanley McChrystal joins the show to celebrate the launch of his new Masterclass and share his approach to empowering teams and cultivating leadership at every level of an organization. He walks us through strategies for encouraging teams to take risks, even when failure carries serious consequences. But he admits that, despite a lifetime in the military, burpees are still the worst. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dan revisits his chat with dermatologist-turned-global-sensation Dr. Sandra Lee, better known as Dr. Pimple Popper. She shares how a simple blackhead video blew up the internet, and what it’s really like to build a business on pus and pimples (while still protecting her patients). Plus, she bursts some skin myth bubbles. Learn more about your ad choices. Visit megaphone.fm/adchoices

Cassandra Peterson (aka Elvira, Mistress of the Dark) joins Dan to pull back the coffin lid on her 45-year reign as the queen of Halloween. She shares how The Groundlings and a one-off local TV gig turned into her pop culture empire, why embracing her alter ego became her greatest business decision, and how she spends Halloween. Elvira also talks about her new cookbook Elvira's Cookbook from Hell (spoiler: it includes Cheese Whiz and crushed potato chips), her autumnal gin, and her friendship with Pee-wee Herman. From reframing Hollywood typecasting to becoming a brand that defines a holiday, Elvira proves that success sometimes means leaning all the way into what makes you different—even if it’s spooky. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this snack-sized episode, Dan revisits his conversation with comedy legend Dan Aykroyd. From managing teams on movie sets to co-founding Crystal Head Vodka, Aykroyd shares what he’s learned about leadership, product design, and sales. Plus, as a lifelong risk-taker, he explains the proper way to eject from a fighter jet. A tip you definitely don’t want to miss. Learn more about your ad choices. Visit megaphone.fm/adchoices

Lucy Guo, the tech founder who unseated Taylor Swift as the youngest self-made female billionaire in the world, joins the show with practical advice and some controversial takes. She breaks down her winning strategy for raising funding, explains why we overestimate risk, and shares her biggest red flag when investing. Plus, she talks numbers on why buying a private jet might be the worst financial move you’ll ever make. Learn more about your ad choices. Visit megaphone.fm/adchoices

Just in time for the new season of the Real Housewives franchise, Dan reruns his chat with OG Housewife Bethany Frankel. She shares how she juggles a million things without losing her mind, the secret to keeping her energy sky-high, and why now is prime time for bold new ideas. This episode is sure to have you ready to hit the ground running. Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when the world’s best-selling author teams up with a leadership expert? You get a playbook for thriving in a changing world. James Patterson, drawing on his experience as a former CEO, master marketer, and publishing icon, teamed up with Dr. Patrick Leddin, PhD to write Disrupt Everything—and Win. The book and this discussion is an awesome mashup of Patterson’s real-world lessons and Leddin’s three-year Vanderbilt study on disruption. They share how to stop fearing change, flip obstacles into opportunities, and why becoming a “positive disruptor” might just be the key to success. Learn more about your ad choices. Visit megaphone.fm/adchoices

How does Michael Strahan juggle it all? From Good Morning America to hosting game shows, running clothing lines, and producing TV, he somehow makes it look easy. In this throwback chat, he talks about the power of compartmentalizing, why trusting your team matters, and how lessons from the NFL still guide him today. Plus, hear his take on Tom Brady, what it really feels like to sack a quarterback, and why nothing can quite replace the game. Learn more about your ad choices. Visit megaphone.fm/adchoices

WWE Superstar Chelsea Green, recently featured in Netflix’s WWE: Unreal, joins the show to talk about her journey through different wrestling personas, how she made it to the biggest squared circle in the world, and why success is about more than just money. Dan does his best not to cringe as Chelsea shares the injuries that come with life in the ring. Having played both hero and villain, she opens up about keeping the noise of online hate from spilling into her real life. After all, she says, her job is to spend ten minutes play-fighting her best friends in her underwear; it’s not that serious. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this Snack Break, Dan dusts off his convo with comedy powerhouse Sebastian Maniscalco. You know him from sold-out stand-up tours and roles in The Irishman and Green Book. Maniscalco is about to hit the road again, starting September 12. He talks about how to find your voice, why the “downs” are just as important as the “ups,” and what it feels like to stand on a set with Joe Pesci, Robert De Niro, and Martin Scorsese staring back at you. Oh, and as a bonus, Dan confronts his addiction to the “A” word. Learn more about your ad choices. Visit megaphone.fm/adchoices