Rianna Middleton

The Unlikely Beginnings of Gimlet Media


Last week, Spotify announced it had purchased Gimlet Media, a digital media company and podcasting network, for $230 million. Gimlet was founded only four and a half years ago by Alex Blumberg and Matthew Lieber.

Despite their recent breakthrough, Gimlet Media’s journey to success was not without bumps in the road. They documented their trials and tribulations on their podcast, StartUp, laughing off their embarrassing fumbles and revealing their unexpected triumphs. If you want to learn about what it really takes to start a business, their wisdom is a perfect place to start.

One of my favorite moments on the podcast is when Blumberg pitches Chris Sacca, a venture capitalist known for his smart investments in Twitter and Uber. Blumberg recorded his pitch and comments on how poorly he executed it. He tried to think through the pitch from a business perspective, outlining the problem, solution and scale opportunities, but he got lost in the presentation aspect of the pitch. He stumbled on his words and struggled to convey his brilliant idea, forcing one of the most well-known investors in Silicon Valley to coach him through his pitch and fill in the logical gaps.

While he may look back on his first startup pitch with embarrassment, he admitted that it was an important step in his learning process. He was coached by an expert and given advice on what investors care about. It was a great example of how you have to fail first before you can succeed.

Blumberg continued to learn through failure, pitching dozens of investors only to be told over and over that he wasn’t thinking big enough, or podcasts weren’t a scalable business. At the end of the day, however, he listened to his gut and stuck with his original idea of creating original storytelling audio content.

I think this is an important lesson for all entrepreneurs. People will doubt your ideas and say you’re crazy for trying something, but often, you know a good idea when you think of one. Constructive criticism is always welcome, but if you’re confident in the basic principle of your idea, you should always stick with it. Like Blumberg, you’ll eventually find the right investor for your company who can see your vision.

Another interesting lesson the show addresses are that startups are a team sport. Even if you come up with a brilliant idea on your own, it’s much more difficult to scale it without a team or partner on your side. Some of the most successful startups in history were founded by partners or teams, after all — Apple, Microsoft, Uber, Airbnb and Twitter, to name a few.

It was inspiring to listen to the story of how Gimlet Media began, and how the founders navigated their bumpy beginnings, failures and all. After listening to the first few episodes of StartUp, I was amazed at how quickly Gimlet transformed their business from a mere idea to a multi-million dollar company. I believe it’s a testimony to the founders’ perseverance.

2 thoughts on “The Unlikely Beginnings of Gimlet Media

  1. My favorite part was the pitch to Sacca as well. It was awesome that he retold his pitch to his face. A good learning lesson! I agree that we can all learn from Gimlet a lot about startups – the failures and successes alike. Good article!


  2. I like your ideas about teamwork very much. Everyone’s ability is limited, but when people work together as a team, the team’s ability is infinite. It is impossible for a man who wants to succeed to fight alone. You have to be part of the team, and you have to be able to achieve common goals through the ability of the team.


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