In 2019, At the age of 45, Andrew Yang decided to enter the race for President of the United States. He’d never run for any elective office before. Yang hoped his signature proposal of giving every American adult a universal basic income of $1,000 a month would help get him into the White House. Though he wound up with a dedicated group of tech-savvy followers known as the Yang gang, the candidate dropped out after losing the New Hampshire primary. Still, he’d developed a taste for politics and in 2022, Yang announced he was joining the race for New York City Mayor. He was the front runner until his campaign lost ground and he wound up losing to Eric Adams. Now, he’s written the memoir Hey Yang, Where’s My Thousand Bucks? We talk about politics, Zohran Mamdani and how Andrew Yang would like to fix the world.

He was editor of Vanity Fair for 25 years during a time that big glossy magazines ruled. Graydon knows everyone and has juicy stories to tell. Even Graydon’s hair became famous for the way it took off on the sides like a winged creature. The magazine was famous for its stories about Hollywood royalty, Brangelina, fashion icons like Calvin, Giorgio and Donatella. All this at a time when people turned real pages and long black limos plus lavish expense accounts reigned. The Vanity Fair Oscar party became the hottest ticket in town. People would do anything for an invitation. One year someone brought a pig as their guest. We talk about excess and celebrity on the new episode of “Now What?”

Singer Ani DiFranco’s career took off in the 90s when she became a big hit with people from the millennial generation, like my son Jon who spent his teenage years listening to DiFranco’s song Untouchable Face over and over again. Her lyrics are intimate, intense. They speak to the raw emotions of adulthood, especially when it comes to relationships and identity. And all these years later DiFranco’s career is alive and well. She’s about to embark on her Spirit of Love tour heading for cities across the country. I attended one of her concerts recently. Her fans are passionate. The energy is electric. I talk to Ani DiFranco about the glories and the downsides of a long career.

Jeanette Winterson is a writer who grew up in a Pentecostal evangelical family in a little town in the north of England. She was adopted. Her parents were poor. There was no indoor bathroom. Winterson dreamed of escaping that life. When she was 16, she fell in love with a woman. Her parents were scandalized. Winterson left home, slept in her car and managed to get into Oxford. She’s fascinated by the ancient fairy tales in The One Thousand and One Nights.” In those tales, Queen Scheherazade tells her husband the king a story every night, stopping at an exciting moment in order to delay her execution. Winterson uses these stories as a framework in her new book One Aladdin Two Lamps. We talk about good relationships, ghosts, elves and AI.

Caroline Paul is an adventure seeker. She’s been a white-water rafting guide and pioneered first descents on unexplored rivers in Borneo. To experience wing walking, she strapped herself to the top of a biplane while it performed maneuvers like loops and rolls. She’s also racked up credits as a luge athlete, that crazy sport where you race down steep, icy tracks on small sleds, lying on your back. Now, Paul pilots a gyrocopter, a machine that might remind you of a praying mantis with wings. Paul says she likes to fly experimental aircraft because they connect her to nature and the possibility of change. We talk about how the thrill of flight relates to themes of love and why Paul says it’s easier to learn a landing than a human heart.   

When Jimmy Wales was 3, growing up in Huntsville, Alabama, a door-to-door salesman sold his mother a copy pf the World Book Encyclopedia. Jimmy fell in love with it. As an adult he had this idea. ”Imagine a world in which every single person on the planet is given free access to the sum of all human knowledge.” The result is Wikipedia, which Wales co-founded 25 years ago. Though not without controversy, Wikipedia is a runaway success. It’s the world’s largest, most comprehensive encyclopedia with more than 1 and a half billion unique visitors a month. That should only happen to “Now What?” I talk to Jimmy Wales about his new book The Seven Rules of Trust, reining in social media and how we can make a difference in a bitterly divided society.  

Until she was 10, Emi Nietfeld led a pretty normal life. It was when her parents divorced that her world fell apart. The parent she knew to be her father transitioned to a woman named Michelle. Her mother was a police photographer with serious psychological problems. In her book, Acceptance, Emi who is now 32, talks about the price she paid for working so hard to overcome circumstances that no child should have to endure. They include stints in a psychiatric ward, living in foster care, stays in a homeless shelter and a suicide attempt at the age of 13. So how did she wind up graduating from Harvard and what lessons can be learned from a childhood where welfare systems fail you? We talk about the notion of self-worth and how hard it is to outrun your past.

It hasn’t been a great year when it comes to treating our fellow human beings with dignity and respect. But it's been a great year for talking to extraordinary people on “Now What?” Larry Charles is a true character who wore his pajamas to work and directed Sacha Baron Cohen in the movie Borat. Along with Gilda Radner and Jane Curtin, Laraine Newman was a hilarious member of the original cast of Saturday Night Live which just celebrated its 50th season. Alison Bechdel, the gifted graphic novelist of Fun Home, has a lot to say about living the life of a gay boomer radical in Vermont. “Now What?” has turned out to be a podcast with a very special community.

Gabrielle Hamilton’s father always told his five kids they had to do something practical with their lives and whatever they did, they had to be excellent at it. Mediocrity was a family sin. Hamilton had a job washing dishes when she was a teenager. She eventually opened Prune, a 30-seat restaurant in the East Village that to her surprise racked up rave reviews. She was honored with a James Beard award for Best Chef in New York City in 2011, followed by Outstanding Chef in 2018. Hamilton was also featured on the PBS series The Mind of a Chef. She realized her dream of becoming a writer with her best-selling memoir Blood, Bones and Butter. Now, Hamilton has a new book called Next of Kin. We talk about dysfunctional families and the pressures of life both inside and outside the kitchen.