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    Risky business unveiled through ‘StartUp’ podcast

    Courtesy+of+Startup

    Courtesy of Startup

    If you want to know what it is like to pitch an idea to a billionaire investor or leave your safe, comfortable job to pursue your passion, Alex Blumberg of the podcast “StartUp” is documenting his journey doing just that — by founding his company, Gimlet Media.

    “StartUp” is a lot like the Oscar-winning movie “The Social Network” sans all of the sociopaths. Blumberg was a producer at “This American Life” and one of the cofounders of NPR’s “Planet Money” before quitting in the summer of 2014 to start his own company. Public radio does not pay very well, so Blumberg’s first challenge was to raise money for his business, which he documents in the first episode “How Not to Pitch a Billionaire.” You would think that this is a tongue-in-cheek title, but Blumberg’s first pitch was to billionaire investor Chris Sacca. Sacca was one of the first investors in Twitter and is a current investor in companies such as Uber, Kickstarter and Medium.

    As you can guess from the first episode’s title, the pitch did not go well. This is not the only blunder Blumberg will make as he documents his entrepreneurial experience. In episodes two and three, Blumberg develops a more concrete plan for his business and has more confidence.

    During his pitches, investors often ask him what his unfair advantage is. They want to know why he is better than anyone else at starting his business. The pretentious sounding answer he gives is that he is simply the best at what he does. All doubt that Blumberg oversells himself disappears in episode four, titled, “Startups Are a Risky Business.” Blumberg wakes up at 5:30 a.m. and immediately starts recording himself. The prior morning, he read Shel Silverstein’s “The Giving Tree” to his kids and talks about how the entire story is a metaphor for the sacrifices made as a parent. You can hear the pain in his voice as talks about the struggles he’s already facing being both a father and an entrepreneur, and his worry that he cannot be successful at either is haunting.

    That is not to say the entire podcast is a downer. Blumberg eventually finds a business partner and some funding. With the help of a specialized firm, they go with the name Gimlet Media for their new media empire. In one of the later episodes, Blumberg even allowed listeners to invest into his company, but due to SEC rules, only very wealthy listeners were eligible to participate. Gimlet successfully finds an office, hires new employees and launches a new show. The latest episode gives listeners insight into the culture inside Gimlet Media.

    Maybe the biggest complaint with “StartUp” is that, eventually, it will have to come to an end. The last few episodes have hinted at a new direction for the show, and Blumberg has brought on a new host to ease the transition. The plan seems to be that “StartUp” will document and report on the founding of other companies, but I doubt they will be able to find someone as transparent as Blumberg to center on.

    To listen to the first 12 episodes, “StartUp” can be downloaded or streamed for free from Gimlet Media’s website.

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    Follow Partick O’Connor on Twitter.

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