5 Podcasts That Will Jump-Start Your 2020 Entrepreneurial Efforts


I love podcasts and I know I’m not alone. More than half of all Americans have listened to a podcast – an astounding number considering five years ago I had trouble even figuring out how to find and listen to podcasts. 

Before I started Listenwise, a listening-skills-building company that turns podcasts and public radio into lessons for teachers, I was an award-winning public radio reporter. I listen to podcasts with both an ear for the content and what I can learn as an entrepreneur, but also for the quality of the storytelling and audio. I thought I’d share what I’m listening to this year to for motivation, education and entertainment as the leader of a small ed-tech startup. Here’s my list:

1. How I Built This

Host Guy Raz is a veteran NPR reporter and his interviews with the most famous company founders are always compelling. The How I Built This format is simple: go deep with entrepreneurs who built well-known companies such as JetBlue, Spanx and Airbnb. But it’s deceptive to think that just interviewing someone creates good audio, Raz knows how to craft a narrative arc. He takes these entrepreneurial leaders back to their founding stories and early struggles. Raz has the ability to get them to open up and be real. The music is always perfect and well-timed. My partner and I have shared and talked about our favorite episodes. When things are going wrong with our company, we’ll say “at least we aren’t up all night making yogurt!” (listen to episode Stonyfield Yogurt). Or I’ll said we need to find our Obama O’s (listen to the Airbnb episode). Listening to these successful founders, I’m often encouraged to find that that they have been in the pit of despair at times. just like me, and rebounded. 

 2. Startup Therapy

This podcast sounds like you are listening in on a couch session with a psychologist and two founders. Wil Schroter and Ryan Rutan give you an unvarnished version of life as an entrepreneur in Startup Therapy. As the founders of startups.com and many other companies, they have been through it all and seen it all. And they don’t shy away from the questions that many are afraid to ask. That’s what I love about it. Episodes like “I’ve Lost Interest in My Startup – Now What?” and “Why Am I So Lonely” or “My Company Is Worth Millions – Why Am I So Broke?” are honest accounts of topics no one talks about in startup land. The style is a music-free conversation between the two hosts and they are really talking to each other, not telling you what they’ve learned. Studies show listening in to someone else’s conversation is very compelling. It’s unscripted, real-life advice that would be hard to get anywhere else.

3. The Pitch

If you are a fan of Shark Tank, then you’ll like The Pitch. It’s always compelling to hear someone else’s ideas and pitches for funding. Each episode has a panel of investors who listen to part of a pitch, ask questions and make a decision about investing on the spot. I know access to capital in between the coasts is hard to come by, so this podcast gives people from all over the country a chance to pitch their ideas and get funding. And it gives you the chance to hear about some exciting companies from a wide range of people. It’s hosted by Josh Muccio, but I find his style canned and he doesn’t seem to add much expertise to the episodes even though he was a startup founder. On TV it’s easy to follow who is who on the panel of five investors, but on a podcast it’s confusing.  I do like that they make an effort to have women almost equally represented as investors and entrepreneurs, but I wish that lineup was also reflected in the real world. Even when episodes of The Pitch are about businesses outside of education (like When Less is Not More, about mens’ clothing boxes, or How Niche is Too Niche, about a travel box of beauty products for black women), make me think about my own pitch. I have had to raise money for my own company for the past seven years, so I am always interested in continuous learning on how to do it better.

 4. Masters of Scale

This podcast is hosted by Reid Hoffman, co-founder of LinkedIn and now a well-known billionaire investor. Masters of Scale is regularly listed as a top podcast for entrepreneurs. I like that each episode gets into business principles or insights behind what helps a company scale. Even though I heard Jenn Hyman and how she started Rent the Runway on How I Built This, I learned about her business behind the business (spoiler: dry cleaning) in the Masters of Scale episode. The format is heavily scripted with Hoffman setting the stage, using clips with the founders, Hoffman providing analysis and making connections with other companies, sprinkled in with music and sound effects. If that sounds like it’s a mish-mash, it is. The music and sound design don’t always make sense and I find Hoffman’s delivery to be stilted. Still, I learn something from every episode.  

 5. StartUp

I could not end this list without giving a nod to the original, the first, the trend setter of all podcasts for start-up entrepreneurs – the StartUp podcast from Gimlet. You have to go back to Season 1 for the magic. In 2014, at the same time I left my public radio reporting job to launch Listenwise, Alex Blumberg left Planet Money and This American Life to start a business, which he chronicles in the first season on Startup. Maybe I love this one so much because he and I were going through the stages of starting a business at the same time. You hear him iterating on an idea, finding a co-founder, naming the company, and getting funding. The difference between his journey and mine was that I didn’t record my embarrassing pitches to investors or tense conversations with my husband. OK,  there are a few other differences. But it’s also excellent because Alex is an amazing radio producer/host. He knows how to use audio clips to tell a narrative with story arcs that have cliffhangers and crying moments. His story of success (Gimlet was sold to Spotify for somewhere around $230 million) might be “old” but it doesn’t disappoint.  

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3 thoughts on “5 Podcasts That Will Jump-Start Your 2020 Entrepreneurial Efforts

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