Fortune Favors the Bold podcast inspires listeners to question everything

Season three unpacks big financial questions from listeners and taps experts to help find answers

It’s a new decade, and that means new beginnings and inevitably, new outlooks on how we approach money.  And while many people ponder big, bold financial questions, few dare to challenge how we all think about money and how it shapes their financial identity.  This season, Mastercard and returning season one host Ashley C. Ford go bigger and bolder by taking listener questions and tapping into expert advice to help listeners find their own answers.

Fortune Favors the Bold season three, created in collaboration with Pineapple Street Studios co-founders Jenna Weiss-Berman and Max Linsky, launches season three today and will drop new episodes weekly through March, culminating in a live episode event during On Air Fest, the seminal podcast creator conference in Brooklyn, NY.

This season Ford brings her unique sense of empathy and humor to the mic to unpack how money is tangled up in everything from ​education and work, to travel and identity, and to seek answers that will help everyone feel empowered to navigate an ever-changing financial landscape in a way that makes sense to them. Expert panelists—including Anna Sale (WNYC “Death, Sex and Money” podcast host), Jada Yuan (New York Times 52 Places traveler) and Daniel M. Lavery (Slate’s “Dear Prudence” podcast host)—debate, discuss and help guide listeners through one difficult financial question each episode.

“At their best, podcasts feel personal and intimate. At their worst, they feel like a one-sided conversation. Getting people to really talk about money meant pushing the boundaries of how people are used to engaging with a podcast,” said Jenna Weiss-Berman, founder of Pineapple Street Studios, a division of Radio.com. “Getting people to call in, asking them to take the journey with Ashley and then calling them back for their own insights and reactions – that’s an exciting new format to play with and I think people really respond well to it.”

The evolution of Fortune Favors the Bold, which saw a 50% increase in listenership in between seasons, began by helping to redefine our relationship with money. Season two went a step further, revealing the unwritten rules that govern our perceptions around money. And season three asks bold questions as a means to unpack and understand our own financial identities and help listeners navigate a changing financial landscape.

“Even when people aren’t talking about money, they talking about money. In my own life, I’ve been working hard to get these conversations out in the open. Hosting this podcast has helped me do that by talking to all kinds of different people with different perspectives,” said Ashley C. Ford.  “It’s given me a chance to explore my own financial identity -- how it defines me, my relationships and outlook on life.”

Midroll ads connect each episode’s theme to work Mastercard is doing, bringing in employee experts who share short anecdotes and examples to explain how the financial technology company is tackling the big issues raised by the podcast.

Fortune Favors the Bold is available on Apple Podcasts, Google Music Play and all other listening platforms.