Hey Startup Podcast, I Miss What We Used to Have Together

Let me start by saying I’m a huge fan of the podcast, Startup, from Gimlet Media. Ever since it premiered three years ago, I’ve been hooked. I’d been through a couple of my own startup experiences prior to the show and it came out right as I was feeling the lure back into the adventurous waters of startup life.

Alex Blumberg and Matt Lieber’s story of founding Gimlet hit on so many of the points I’d been through in the past. There’s the rush of excitement when you’re starting out, the anxiety and discomfort of hashing through equity splits, bonding over a shared vision, brainstorming terrible company names. The list goes on and on.

It also hit on plenty of elements I hadn’t experienced, like meeting with billionaire investors to raise money right out of the gate. That had never been my path but I was fascinated to hear the intimate details of it.

That first season was when podcasts were being cemented into my daily life. My commute back and forth to my last full time job was when I’d listen to their story.

Startup wasn’t the motivating factor for me to pursue entrepreneurship again, but it was an amazing friend to have around while it was happening.

To hear the similarities between my experience and what Alex and Matt went through was extremely comforting. I have a family too, and I was substituting a steady, well-paid, hard-earned position for a life that’s filled with uncertainty. Those kinds of decisions can make you feel crazy at times. Hearing someone else share those ups and downs makes you feel a little less crazy and much less alone.

And on the positive side, it was an incredible reminder of that connection you get to your work when you’re completely invested in it. That’s something everyone should seek out no matter what their situation is.

The show continued to fill that niche for me when the second season came around. Hearing the story of Dating Ring and their path through the incubator Y Combinator, was even more distinct from my experiences. Despite that I still felt a kinship with Emma and Lauren through their crazy journey.

And that was the draw of the show’s experience for me. Even when the exact details of my path diverged from the folks in the show, the personal and emotional side of the story always kept me in.

Next up was a mini-season where we got to check back in with Alex and Matt. Once again, this provided some great lessons from their experiences over that first year of growth.

But after that the show started to change.

What was different?

In the following seasons of Startup, I feel like there was a real shift around what the show focused on.

There have still been some updates with the Gimlet crew that are very compelling. In fact, the episode in season four where Alex meets with executive coach and startup advisor, Jerry Colonna, might be the single most affecting episode of the entire series.

But overall, what I felt like changed from the first half of the show’s life to its second, was the focus on the stories versus the people.

Starting in season three, we saw a new type of “short form” story. Some examples were covering well known companies like Justin.tv’s evolution into Twitch, and the story behind Friendster’s rise and fall.

But there were also plenty of stories around lesser known individuals and companies ranging from a Greek yogurt maker convicted of burning down his own factory, to the journey of the inventor of SlamBall.

Slamball! (via YouTube)

But while the early days of the podcast felt like you were living the challenges of running a startup with entrepreneurs from the inside, these episodes felt like producers telling me an interesting story about a startup from the outside.

There was a light revisiting of the old style in the back half of season 4, where show host Lisa Chow spent multiple episodes covering the comeback of infamous American Apparel founder, Dov Charney.

Lisa did an excellent, even brave job telling the story, but it was centered around the tabloid-esque drama of American Apparel’s rise and fall more so than any relatable drama of what it’s like running a company.

The time that was spent focusing on Dov as a person was less about his entrepreneurial challenges and more about his personal issues.

The summary of the experience for me was once again a documentary-style presentation of what happened from the outside.

That’s not why I started listening to the show.

I didn’t listen to season one because I wanted to hear a crafted tale of a podcast company that makes it big. And I didn’t listen to season two because I cared about dating services.

What I connected with were the individuals behind those companies. Listening to and relating to those very real struggles. Getting to know those people. Empathizing with their challenges. Feeling a sense of affiliation and inspiration with them through the community of entrepreneurship.

That type of connection has nothing to do with being part of an unusual or ground breaking business. The connection is about personal access into the experiences that come from living a life that’s intertwined with a company.

This is what I love about entrepreneurship. This is what made me a fan of the show. This is what I feel has been missing.

What would I like to see?

Look, I’m just a fan. I have no insights into Gimlet’s business model or customer data. I can easily imagine some reasons why they’ve shifted the format of the show, including:

  • They legitimately believe this format is a more compelling form of storytelling
  • It gives them the ability to spread production across multiple stories in parallel
  • They get strong marketing hooks via notable companies and founders
  • There’s a lack of companies willing to commit to multiple months of production and providing an intimate level of exposure into their business (kind of doubt that one, but maybe)
  • They’ve simply proven out that for this show they get more downloads from the one-off episode format vs. longer serialized stories (though we know Gimlet hasn’t abandoned serialized stories in general)
We know Gimlet still believes in long form, serialized content for certain shows…

All of those could be true along with a million other factors that I have no idea about.

As a fan of Startup and Gimlet overall, I want to see them succeed. I would never fault them for doing what’s necessary to run a successful business. They’ve certainly earned my trust and respect from a storytelling product perspective.

All I can offer up is my individual experience as a consumer of the show. I may be in the minority. Maybe even in a small minority.

But from my perspective, as a fellow entrepreneur and founder of a startup, I’m not getting the same connection from the show that originally pulled me in.

I came to the show and stayed with the show because of the emotional connections I built with the founders in the stories. I miss that component now and would be really excited to experience it again.

Maybe there’s room for both. Maybe there could be a deep dive, serialized story that focuses on the journey of a single company, and then a separate show that only does one-off episodes with unusual or historically significant companies.

To me they’re very separate things. Yes, they’re both technically about startups but only in the broadest terms. The experience they provide, the depth of story, and the storytelling perspective are completely different.

I’m definitely not abandoning the show or protesting against Gimlet. I’ll keep listening to Startup and lots of Gimlet’s other shows because they consistently deliver a very high quality entertainment product.

I just selfishly want more of the thing that got me hooked in the first place. I want the product that had a unique and valuable place in my listening life.

Any other Startup fans feel the same?



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Clay Ostrom

Clay Ostrom

I help companies create more profitable brands. http://mapandfire.com