Startup Podcast: Season 3, Episode 1 — Almost Famous


Startup is by far my FAVORITE podcast from Gimlet Media. But it wasn’t until the end of this episode I finally realized why.

The theme of this season is ENDINGS. Happy endings, sad endings, and everything in between. We’re told they’ll be “telling stories of all different kinds of endings and people who go to extreme lengths to hold their business together.” It almost sounds like a relationship show.

Their first story is a classic Silicon Valley rags-to-riches tale, though at the end of episode 1 the startup in question is still very much in its “rags” phase. The four co-founders have $50,000 in the bank, a cramped apartment in San Francisco, a hope, and a dream. Co-founder Justin seems to be headed toward chronic back pain as he’s lugging around a 30 pound computer on his back. (If you’re an entrepreneur, can you sue yourself for worker’s comp?)

As they’ll likely reveal next week, this company will Mad Max it through the “trough of sorrow” to become a billion dollar company. (If you haven’t guessed which famous startup this is, and care to be spoiled, click this link here.)

Justin’s is the kind of story that gets the most media attention. We LIKE stories about winners, and are naturally attracted to successful underdogs. This IS the United States of America after all.

But for my money, where this season of Startup provides the GREATEST value-add will be on its focus of stories that AREN’T often told. Stories about the entrepreneurs that never make it big. If Justin’s company is a great white unicorn, what happens to the other 99.99%? To those people who are working and fighting as hard as Justin and Emmett, but have no pot of gold at the end of their rainbows? How these people pick up the pieces and move on with their lives is what I’m personally most interested in.


The big change for Startup Season 3 is their decision to cover an assortment of companies rather hyper-focusing on just one. I can understand why they made this decision. First and foremost, it prevents The Dating Ring problem of season 2, which provided a priceless amount of free media for that one lucky startup. I had never heard of The Dating Ring before, and I’m sure that but for Startup I still never would have. That’s a little weird, and a little unsettling — as Alex and Lisa themselves admit in this episode, where they also shatter whatever’s left of the fourth wall.

So this IS the right move for them. AND YET, it’s also very clear that something will be lost as the podcast shifts from depth to breadth. Gone is much of the serial effect of the show. Each episode, or few episodes, we the listeners will be asked to start from scratch, with a new set of entrepreneurs and their stories. It’s like going from a TV show like Lost to Quantum Leap.

Having said that, there IS one entrepreneur that unites all the disparate stories together. This person is the true protagonist of this podcast, and the one I’m rooting for the most.

There IS one entrepreneur that unites all the disparate stories together. This person is the true protagonist of this podcast, and the one I’m rooting for the most.

I’m talking of course about Startup’s host herself, Lisa Chow.

Lisa has been an economics reporter for several years. She worked previously at Planet Money and at FiveThirtyEight.com. She also mentioned in this episode she has a three year old son. Journalists naturally DON’T want to become the story itself. But as I was listening to this episode, I couldn’t help but realize that ever since last season’s episode “Profiled” — an episode where Alex Blumberg put Lisa ON THE SPOT by “outing her” if you will, for being an Asian American female married to a white male — I’ve felt an affinity toward Lisa. Like I said above, I’m rooting for her to succeed.

Lisa is the narrator that unites the stories together. And more than any particular featured startup or entrepreneur, the suspense of the show is tied to whether or not she will succeed in creating compelling, insightful, and touching narratives. The work she does in stitching these stories together is a major reason I keep coming back to the show.


One final coda — this episode was supposed to drop on April 14th. But Gimlet sent out a mysterious tweet early that morning stating that the release would be delayed:

The episode then finally became available many hours later — by my count it was released on or about 1:35 am in the wee hours of April 15th. (Hopefully the Gimlet crew already filed their taxes.)

Of course, the big hairy question is — What happened during those 15 or so hours? I can only speculate that whatever changes were being made weren’t simply minor tweaks or edits. My guess is that it was an all hands on deck sprint to fix whatever was broken with the launch. These hours must have surely been extremely stressful and exhausting.

I can’t help but wonder if anyone had a microphone handy to document those harrowing fifteen hours. If so, that day alone could be fodder for an entire future episode. Either way, the bottom line is I’m AMPED that season 3 has begun! 🙂

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The Podcast Enthusiast is not sponsored by or associated with Gimlet Media or the Startup Podcast. However, as fans of the show, we encourage you to subscribe to and support their work.

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