No podcast better captures the thrills and struggles of launching a company. Created as a remarkably candid docuseries on the birth of podcasting business Gimlet Media, it now traces the surprising stories of other enterprises.
Sample episode: The inventor of the slap bracelet on why he made no money from the '90s fad.
This show--launched in 2008 to help explain the financial crisis--offers fascinating explorations of the intersection between economics and culture.
Sample episode: A look at why many Irish pubs are so similar. The answer? In the 1970s, one man defined the elements of a Dublin bar, created a kit, and sold thousands around the globe.
Each installment starts with the same question: "What is your name and what do you do?" Guests then reveal details of their jobs, whether they're a neurosurgeon, a novelist, a pollster, or a clown.
Sample episode: A professional Santa spills trade secrets: Don't work shopping malls, wear a real fur suit, and never say, "Ho ho ho."
A giant bite of Apple. Hosted by analyst and technology writer Neil Cybart, this show goes deep into all things Cupertino, with some of the most informed analysis you're likely to find.
Sample episode: Apple is famous for its design. So why are products like Apple Music and Apple Watch so weirdly hard to use?
Journalist Mandi Woodruff and personal-finance expert Tiffany Aliche chat about news, relationships, and other topics, but they're especially incisive when discussing their successes and failures in the business world.
Sample episode: Aliche on overcoming $300,000 in debt to build a financial-advice company.
How I Built This
This series explores backstories of various big businesses, from AOL to 1-800-GOT-JUNK. The storytelling is simple and linear, leaving space for gripping personal tales to emerge.
Sample episode: The creator of the 5-Hour Energy drink goes from Princeton dropout to Hindu monk to beverage billionaire.
Editors from culinary site Eater glean insight from chefs and other industry pros, both famous (Anthony Bourdain) and less so (cookbook photographer Evan Sung).
Sample episode: Wolfgang Puck explains how he built his empire, then rips into Eater's restaurant critic, who'd panned one of Puck's steak houses.
Tech watchers Ben Thompson and James Allworth tackle topics of the moment--fake news on Facebook, Uber's scandals--and offer broader discourse on where the digital world is headed.
Sample episode: Thoughtful debate on what tech companies are getting wrong about self-driving cars.
I Hate My Boss
Former Nike and Oprah Winfrey Network marketing executive Liz Dolan and executive coach Larry Seal offer advice on your stickiest workplace conundrums.
Sample episode: Dealing with liars in the office, plus an interview with Airbnb's head of talent management, Andrea Robb.
Focused on innovation and technology in the fashion industry, this podcast digs into notable developments in manufacturing, design, retail, and other areas.
Sample episode: How online menswear retailer Proper Cloth is tapping data and digital tools to amp up its sales.