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Gimlet’s Alex Blumberg and Matt Lieber started with a podcast about the trials of entrepreneurship. They’re still learning how hard that life can be.

When you run a startup, “it feels like everything is about to break,” co-founder Lieber says.

Gimlet founders Matt Lieber, left, and Alex Blumberg
Courtesy Gimlet

Alex Blumberg and Matt Lieber are seeing a therapist and they don’t care who knows it.

More specifically, the Gimlet founders are seeing a business therapist — executive coach Jerry Colonna, who they first met when he appeared on Gimlet’s first podcast, StartUp. That show, hosted by Blumberg, exposed the “myth of the entrepreneur” and how fraught founding a business can be.

“If you ask any entrepreneur how it’s going — ‘Oh, we’re crushing it, Peter!’” Lieber said on the latest episode of Recode Media with Peter Kafka. “‘We just made a great hire! We just closed our most recent round of funding! We got Mastercard as a client! Everything’s going great!’ The truth is, the way it feels is 180 degrees the opposite. It feels like everything is about to break.”

Now, Gimlet has more than 110 employees on the payroll and, last year, it raised $20 million, bringing the company’s valuation to $55 million. Blumberg said the stakes have been raised such that when he and Lieber make mistakes, they have the potential to do more damage. He praised Colonna as “instrumental” in helping them identify their own limitations before those mistakes happen.

“A thing that brings down lots and lots of leaders is their own blind spots about their own triggers, or their own things where they’re acting not out of rational interest but because they’re acting out of emotion that they don’t understand,” he said. “And I think that’s very real. If you haven’t fully come to grips with what your baggage is, it just spreads throughout your organization.”

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On the new podcast, Lieber and Blumberg also talked about how Gimlet is expanding beyond original audio shows like StartUp, Crimetown and Reply All and into two newer businesses: Film and TV adaptations of their podcasts, such as a TV series reworking of the show Homecoming, now starring Julia Roberts, that will hit Amazon this fall; and branded podcasts, which are completely underwritten by a single sponsor.

No one is going to listen to a 20-minute advertisement for Gatorade or Tinder or anyone else,” Lieber said. “So our starting assumption is, put the listener first. Let’s actually make a show that we feel like fills a need in the market.”

So for a show like The Secret to Victory, a sports podcast sponsored by Gatorade, Gimlet has educated its sponsors about the importance of “emotional honesty” in audio, Blumberg said. If people hear other people talking in an authentic way, they won’t turn it off or tune it out.

And from a business perspective, that sound also ripples out to how a podcast goes viral.

“Podcasts are an intent-driven medium,” Lieber said. “Podcasts are not like Facebook, where someone goes and just sees what’s in the Feed, and if the Feed serves you branded content or it serves you your cousin’s photos or it serves you news, you’ll take a look at it. Podcasts, people actually have to seek them out, or a friend has to tell them, ‘Hey, this is a really interesting show.’ That’s the final argument for why you have to make the programming good and it can’t feel like an ad.”

If you like this show, you should also sample our other podcasts:

  • Recode Decode, hosted by Kara Swisher, is a weekly show featuring in-depth interviews with the movers and shakers in tech and media every Monday. You can subscribe on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.
  • Too Embarrassed to Ask, also hosted by Kara Swisher, answers all of the tech questions sent in by our readers and listeners. You can hear new episodes every Friday on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

If you like what we’re doing, please write a review on Apple Podcasts — and if you don’t, just tweet-strafe Peter. Tune in next Thursday for another episode of Recode Media!

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