Season 4 of StartUp is almost here. Here's a sneak peek of the fourth season, which kicks off with some episodes about the company that makes this podcast: Gimlet Media.

Since we last checked in on Gimlet HQ, the company has grown a ton. And with growth, come the growing pains. Season 4 of StartUp premieres on October 6.

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Something is amiss at 2680 Madison Road. In the thriving Cincinnati neighborhood of Hyde Park, the property is sandwiched between several decades-old Cincinnati staples, and a stone’s throw away from an upscale shopping center. The space is huge, the parking is ample. And yet, the building has been abandoned for five years. Seven different businesses have cycled through the address over the last thirty years. It seems that every business that inhabits its four walls is destined to fail.

Alex Blumberg sends StartUp Senior Producer Kaitlin Roberts to his hometown to investigate this peculiar property. With a microphone in hand, she books a ticket to Cin City.

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Edgar Diaz has dedicated his life to dairy. He sees an incredible beauty in milk and the things that can come from it: soft cheese, rich dulce de leche, and creamy yogurt.

He knows that to produce a really good yogurt, the conditions are just as important as the ingredients. You can use the freshest milk, but if your temperature is off or the timing inexact you risk ruining the whole batch.

Edgar has a lot in common with some of the world’s most successful founders: intense passion, a deep knowledge of his product, and awards and acclaim from peers in his field. He seems to have all the ingredients for success, and the conditions seem right, so why is he so far from it?

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Coss Marte went from running a multi-million dollar drug operation to sitting in solitary confinement. And it’s here, alone in his cell, where he gets the idea for his next business: a fitness company inspired by his time behind bars. But Coss quickly learns that building a legal business comes with its own set of challenges—one being that pitching your company on stage to a bunch of investors requires a slightly different approach to selling an eight-ball outside a busy New York club.

Building a startup is a tough and uncertain endeavor for any founder. But for one with a criminal history, the journey can be far more complicated.

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Coss Marte is getting ready to pitch his company to a panel of prominent entrepreneurs and an audience of hundreds. He’s competing against five other startups for a chance at $100,000. With this money, Coss hopes to grow his small exercise studio in the Lower East Side of Manhattan into an international fitness brand. 

But this isn’t his first experience with scaling up. In his early twenties, Coss ran a business that brought in nearly $4 million in annual revenue, a business that catered to doctors, judges and lawyers. A business that landed him a seven year prison sentence.

This is part one of Coss’s story on his path from felon to founder.

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Two men decide to start a company. Everything is going well... until it’s not. That’s the moment they decide to start recording their conversations—painful, awkward, emotional conversations.

Jason and Vincent launched Bento about a year ago. Their goal was to make Pan-Asian food fresh, tasty, and on-demand. They joined the food tech swell just as it was winding down, just as the funding was drying up, just as the smaller players were being weeded out. With only a year under their belt and a quickly draining bank account, Bento’s odds don’t look good. We listen in on the co-founders as they try to decide whether their setbacks are just bumps on the road to success or a sign to shut things down.

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It’s not uncommon for shoppers to walk out of Mary Going’s store feeling on top of the world. Mary runs Saint Harridan, a company that makes custom suits for the gender non-conforming. With her store, Mary has created a space that caters to the needs of butch women and trans men—something that doesn’t happen very often. Her fans are enthusiastic and dedicated, her products are selling out… and she can barely pay her rent.

Saint Harridan is struggling to raise enough money to cover basic costs. Mary knows the demand for her product is there, but it isn’t translating into dollars. Her runway is getting shorter and shorter, but she’s hoping that by turning to her community, she can buy time and make a comeback.

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When a group of college kids in Florida set out to change the music industry, they did not anticipate quite how disruptive they would be. Their mission was a noble one: bring an end to online piracy by offering cheap, convenient, and legal access to music. Their execution, however, was less than thorough. And when you're dealing with protective music labels, forgetting to dot an "i" or cross a "t" can mean being one lawsuit away from the swift and unceremonious death of your company.

This is the story of Grooveshark, the people who built it and the relationships that were tested during its rocky road to growth—and eventual demise.

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Mike is on a mission to bring his customers something they desperately want. Every week, he embarks on a long and unpredictable journey across international borders and smuggles back some highly sought-after goods. And though what he’s doing is technically legal, Mike goes to unusual lengths to evade authorities who want to shut his whole operation down.

What Mike does is a hassle. He’s tired, he’s ready to move on. Still, he can’t seem to shake it, and finds himself stuck running a business he never imagined would make it this far.

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We pick up where we left off in the last episode, and hear how Justin, Emmett, Michael, and Kyle try to extend the life of their video-streaming company by making some risky but important decisions. In the process, their scrappy startup catches the eye of some very powerful people who challenge everything they’ve built.

The road of a startup is a bumpy one and, as Justin and his team are finding out, they have only just gotten started.   

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