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My 5 Favorite Podcasts for Entrepreneurs

If you know me at all, you know I’m obsessed with podcasts. The stereo in my last car broke ages ago and instead of fixing it, I just started listening to podcasts exclusively. Having spent the last three years hosting a show that’s garnered a global audience of thousands and sold out two live events I’ve developed a pretty solid appreciation for what makes a great podcast. Whenever it seems relevant I can’t help but share about my new favorite show.

Here are my five favorite podcasts from the world of business and entrepreneurship, with some guidance to help you pick which ones are best for you.

1. Startup

After making the leap to start my own business, I’ve spent the last month bingeing the entire catalog of Gimlet Media’s Startup “a show about what it’s really like to start a business.” The show kicks off following the journey of host Alex Blumberg’s journey to launch the podcast network that produces the show.

Startup covers so much of what goes into launching a business from developing partnerships and securing funding to evolving from a practitioner into a leader, and they hit these topics so boldly and authentically with recordings from actual meetings, pitches, and tough conversations within the business. Startup is a like a reality show for business – without all the binge drinking and forced sexual tension.

2. Masters of Scale

Reid Hoffman, founder of LinkedIn, investor at Greylock, and host of the podcast Masters of Scale, has truly blown me away with this show. Unlike typical interview style business podcasts, Masters of Scale isn’t just a loosely edited conversation; every episode has a strong point of view and is tightly edited to help make sense of the the theories being presented. Hoffman interviews a wide range of business leaders and uses their unique stories as case studies to share and test his theories for growing a business.

While I really love hearing the journeys of each of these entrepreneurs, the true strength of the show is that it cuts in opposite points of view and counter examples from other guests. Masters of Scale never leaves you with a simple “do this and your business is sure to grow”, rather this listener is challenged in their own assumptions.

3. HBR Ideacast

I don’t listen to every episode of Harvard Business Review’s Ideacast, but I do subscribe. This is a weekly show that interviews C-Suite leaders of the biggest corporations in the world, professors from leading business schools, and researchers sharing their latest findings. Each episode is under half an hour and I mostly listen as a way of staying generally informed about business trends and market sectors I would l likely remain ignorant of.

4. How I Built This

If it’s not obvious by now, I love personal stories. There’s so much to learn from others who are walking a similar path in life. Anytime someone shares their story, I consider it an act of generosity. From NPR, How I Built This with Guy Raz, is a diverse collection of personal stories from “innovators, entrepreneurs and idealists—and the movements they built.”

I’ve learned about the unique challenges of starting a business in the food space, building an e-commerce brand with overseas manufacturing, and starting a business with friends. I listen to every episode of this show.

5. Freakonomics Radio

Freakonomics Radio is actually my most recent subscription, and I’m kind of upset that I haven’t been listening to this show for longer. The whole “Secret Life of a CEO” miniseries was fantastic and the current series on How to Be Creative is relevant to my work with Black Roses.

Like all of the other shows I’ve shared, Freakonomics radio covers a wide range of industries and topics, but what I love most is the statistical and academic insight host Stephen Dubner and his guests share in a way that’s approachable for me.

Honorable Mentions

If you’re an overachiever, here are a few other shows worth checking out.

My Favorite Podcast App

If you’re on an iPhone, do yourself a favor and ditch the built in Podcasts app and switch to Overcast. Here are three reasons why:

  1. Smart Playlists – Create custom playlists that group your shows together by topic (or however you want).
  2. Custom Speeds – I don’t listen to any podcasts at 1x speed, and Overcast lets me set a custom speed for each show if I want. Some hosts talk more quickly than others a so a 1.2x speed is great, but most shows can be cranked up to 1.6x.
  3. Uploads – I pay for Overcast because I want to support it’s development, but I also love having the ability to upload random audio files I want to listen to and have them show up in Overcast.

I hope you’ve found at least one new show that will be helpful to you, and I’m sure you’ve got some that would be helpful to me. What is missing from my list?

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