5 Early Truths on the Founder’s Journey: The Startup Podcast

November 30, 2014

10:30 am

Everywhere you turn today, you are hearing about Serial Podcast. This journalistic audio narrative, from the creators of This American Life, is convincing an increasing number of NPR fans that podcasts are the latest thing. But it’s been almost two years since the Adam Carolla podcast became a target of a patent troll claim, and it’s been ten years since the term ‘podcast’ was acknowledged in print media. (It was also nearly six years ago that I myself co-hosted a podcast that was crafted in GarageBand and broadcast on iTunes, but don’t bother Googling it.)

However it is that the public is coming to enjoy and consume podcasts, it expands the acknowledgement and awareness that consumers want to have more choice in, and control over, the content that they consume. Alex Blumberg, best known for also having produced This American Life, has recently launched his own podcast network. But what’s more than that, he documented its launch in the form of Startup Podcast.

1. That Someone is Me

“I decided to take what I’d learned from reporting on other people’s businesses, and start my own business,” Blumberg announces in Episode 1 of Startup Podcast. He felt that podcasts focused on storytelling and journalism were missing from the current podcast lineup, and “it seemed like someone should come up with money to invest in making new shows like these, and come up with a theory about how those shows could be profitable.”

Not only did Blumberg have to come to the realization that he needed to be the one to start such a business, but he also decided that the very story of doing so was one that needed to be shared. “I’m calling this miniseries ‘Startup’,” he shares with the audience. He began recording the awkward and difficult conversations that happen as a startup is created. Startup Podcast, of course, covers the type of information there is to learn about creating a podcast network, but fellow founders can certainly relate to the discovery process in developing any product to fit a particular vertical or market.

2. Tighten Up Your Story

“You’re a 29-year old tech-savvy professional and you’re still listening to terrestrial radio?” Blumberg’s enthusiasm for revolutionizing podcasts with better content nearly comes to a crashing halt when he meets someone he thinks is exactly his customer demographic. But he has larger issues to address. This business will need a lot of money. He’s not sure how much, but Twitter legend and famous investor Chris Sacca has agreed to allow Blumberg to pitch him.

After Sacca suggests a walking meeting, the aspiring entrepreneur has to stammer through his presentation without the use of PowerPoint. “I sound like a douche bag,” he narrates, referring to the jargon-heavy string of garbled Problem – Solution – Money rhetoric that falls out of his mouth. “Tighten up your story,” Sacca coaches.

3. What’s the Exit?

After coming to the realization that Sacca isn’t simply looking for a revenue-building business, Blumberg has learned one of the first lessons of startup: will you make your investors rich? Revenue is not the vehicle to get there. Becoming acquired is the only way to really get an investor excited. “What’s your exit? Who will acquire you?” is the question you need to answer when you want someone else’s venture capital. He gets a second opportunity to pitch when Sacca sends him to partner at lowercase ventures, Matt Mazzeo.

“Investors want to be part of something large,” Blumberg’s friends advise him as he prepares for this meeting. The collaborative practice session is painful to listen to, as the crew focuses on what shitty words will be packed into his horrible business tagline pitch. Company name: providing grandiose adverb adjective solutions for grandiose adverb adjective consumers is about to put the next investor to sleep as well.

4. I Love It, But Change It

“There are questions here that you need to assess,” Mazzeo advises him. “In my mind, I think you can build a larger audience.” Mazzeo also thinks that this idea is not considering all tech avenues available to him, and that he should consider the breakthrough opportunities available to become truly innovative. “Podcasts are still the same old mp3s that they’ve always been,” Blumberg admits. “Podcasting hasn’t broken out into the broader mainstream,” Mazzeo adds.

Blumberg has to identify and discern among the ideas that he collects from investors. Should he look into creating a tech differentiator, rather than simply the journalistic offering he is hoping to provide? He wouldn’t be the first founder to change his great idea and move on to be an enormously successful business.

5. Startups Are a Team Sport

The stresses of family life and starting a business, in addition to the advice that many more investors give him, brings Blumberg to realize that he needs a business partner. As he presents this awkwardly-worded and emotionally-laden proposal to future cofounder Matt Lieber, Lieber acknowledges that, “it is a marriage of sorts.”

But it’s a marriage with very difficult, and somewhat hurtful, conversations and realities that must be acknowledged. In early equity negotiations, everyone has an opinion, and no one is right. Lieber shares his reaction to Blumberg’s initial offering: “There is a subtext to ‘I am key to the success of this company’, which is, ‘and you are not.'”


This is an ongoing journey, one that will resonate with every startup founder and early team member. Gimlet Media has added a second podcast to the network, and recently completed their fundraising round which included a crowdfunding portion from listeners.


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Previously the Managing Editor at Tech.Co, Ann Diab has a background of launching and nurturing of startups and tech companies. Empowering and educating entrepreneurs and startups to better productivity and culture is her passion. Growth Manager at WorkingOn to enable folks all over the world to enjoy work and improve communication. Follow me on Twitter.

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