What We're Into: StartUp Podcast

Startup stories tend to be inspirational tales that gloss over the truth, often focusing on the big money when a business is sold instead of the details of getting to that point. We've been fans of the podcast StartUp since its first season, which broke down the process of getting a new venture off the ground into relatable, sometimes entertainingly painful anecdotes. The very first episode is called "How Not to Pitch a Billionaire." It features audio of host Alex Blumberg shakily delivering his business pitch — for Gimlet Media, the podcasting platform that hosts the show — to a high-profile Silicon Valley investor while walking by a noisy highway overpass.

Blumberg's willingness to share his awkward experience cuts through the business-y seriousness of approaching a venture capitalist, and illustrates how the path to starting something new isn't neat, linear, or without uncomfortable detours.

Gimlet Media is now up and running with six shows and a growing staff, and StartUp has followed the company's progress while also examining other angles of the world of new businesses. Now in its third season, the show has shifted to a new piece of the process that most outsiders don't see: what happens when businesses get stuck. In the opening of season 3, Lisa Chow (who takes over from Blumberg as the season's main host) describes the companies covered as "caught in the moment when something needs to change, and it's not clear what will happen next."

Bad things happen to the startups profiled here: They get taken to court, are sent cease and desist letters, or are simply dismissed as having terrible ideas. The subject of one episode gets banned from Trader Joe's; another gets yelled at by Kanye West.

But like "How Not to Pitch a Billionaire," these stories are not just cautionary tales, but an entertaining view of how businesses work that goes beyond dry, corporate-speak success stories and best practices. They offer an intimate look at the human element of startups: the relationships, the personalities, and the painful emotions that come with trying (and sometimes failing) to build a company.

Most entrepreneurs probably don't have much in common with Mike, the subject of episode 3, who wears disguises and drives a beat-up van so he can smuggle groceries from Trader Joe's into Canada, where the grocery chain doesn't operate. But they might find something compelling and identifiable in his drive to keep going in the face of opposition and a chaotic lifestyle. Near the end of the episode, reporter Kaitlin Roberts says, "Mike finally has the option to shut down and he’s plunging himself back into the chaos. There’s something about being in this situation that drives him ... Living in chaos is something Mike is very good at. And it’s hard to quit something you’re good at."

You can listen to the season's first four episodes now at Gimlet Media.