The 7 best podcasts I’ve found for entrepreneurs (and principles for finding even more)

If you’re like me, you might be enslaved to the idea of productivity; getting the most out of every free moment to improve yourself and your business. Whether it’s in transit or at the gym, I’m always looking for opportunities to take time when my brain is idle and gain some skills or insight passively.

To this end, podcasts and audiobooks have been enormously helpful. Below, I’ve compiled the 7 podcasts that have benefited me as an entrepreneur and leader by allowing me to learn from those who have been there before, and what it took to get them to where they are today.

My Principles for Finding New Podcasts

With a deluge of podcasts out there, how can we separate the wheat from the chaff? Before we jump in to my top 7, here are a few of the principles that guide which podcasts I listen to (and any other media I consume as well):

Does this respect my time?

As an entrepreneur, the one thing you have even less of than money is time. In the internet era there’s no shortage of content, and those who are able to take full advantage will be those that use discernment when deciding what to listen to, and what to cast aside.

Measure the opportunity cost — what are a few other ways you could spend 25–40 minutes every day? Learning a new language, re-evaluating strategy, calling family members who may feel like they’re playing second fiddle to your career?

Podcasts present an incredible opportunity to learn on-the-go, but there’s more bad than good out there. Treat your time like any other precious resource you have, and make sure the podcast you’re listening to does the same.

What is the motivation of the creator?

How do you determine what’s bad content and what’s good content on the internet? The first question I ask is “what is the primary motivation of the creator?”. There are innumerable podcasts and articles on the internet that exist solely to build a reputation or capture leads for the author. For podcasts, this usually looks like a consultant or network marketer promising to teach you how to live your best life/make millions — while interviewing other consultants and network marketers over Skype. Bonus points if the word ‘hustle’ is in the title.

There’s nothing wrong with these, but it doesn’t take long to realize, as the listener, this podcast is not about you. It’s not about teaching you, giving you valuable perspective, or helping you understand the struggle of starting a business from scratch. This podcast is about them, getting their name out there, capturing new leads, etc. I stay far away from these.

Is this the best medium for this content?

This is a lesson I learned the hard way, after purchasing a few audiobooks I was really excited for. They were incredibly helpful, filled with practical, tangible advice, and once it was all said and done, I didn’t remember any of it.

The issue wasn’t the content, it was the medium. Personally, I don’t do well with ‘how-to’s over audio — I need to take notes, highlight, and have processing and acting on that information be my sole focus. I’m usually multi-tasking when listening to audiobooks or podcasts, so content like this is a bad fit. Typically, stories or interviews with one or two principles being taught work best, but everybody is different. The key will be understanding your personal learning style.

Finally, silence is not a bad thing

This is a principle I need to remind myself of daily — there’s incredible value in taking 15–30 minutes to just be silent. Last year, I started journaling twice a week for about 40 minutes in the morning, and it’s been remarkably helpful. I’m able to work through relationship and business issues, and identify blind spots in my character or mannerisms I have that may be adversely affecting those around me.

Podcasts can be incredibly helpful, but they fill up brain space that could be used elsewhere. I set a goal for quiet time daily/weekly, and then let podcasts fill the time around that.

Now that you know the thought-process behind how I choose the podcasts I listen to, here are the 7 best podcasts I’ve found for entrepreneurs like myself.

Masters of Scale — Reid Hoffman

Reid Hoffman is the Co-Founder of LinkedIn, former COO of Paypal, a prominent venture capitalist, and seems to be firmly in the “spend most of my time giving back to others” stage of his career. Masters of Scale shirks the traditional podcast format of interviewing somebody famous/accomplished (there’s more than a few of those on this list too, don’t worry). Instead, Hoffman takes interviews with Mark Zuckerberg, Sheryl Sandberg, AirBnB’s Brian Chesky, and builds them not around people, but concepts. He weaves his own insights with Zuckerberg’s or Sandberg’s to form a cohesive narrative, sharing some of the principles he’s learned over the years.

If you’re an active entrepreneur and only have time for one podcast in your life, this is the one I would recommend. It combines stories from some of the industry’s biggest players with practical, take-home advice that could change the philosophy of your business. There’s been a few times at the Bootkik offices where we’ve given our colleagues the assignment of listening to a Masters of Scale podcast over the weekend, as we’d be enacting changes based off it on Monday.

The Pitch — Gimlet Media

Pitching to investors can be a scary, but exciting experience for entrepreneurs. Shows like Dragon’s Den and Shark Tank have popularized the process, but given time-constraints, there’s a lot that gets left on the cutting room floor (for example, each pitch on Dragon’s Den is an hour long — only 7 minutes make it to air).

Gimlet Media’s The Pitch provides a more unfiltered view of the process. Each episode is 30–40 minutes in length and revolves around a single entrepreneur pitching to investors. Host Josh Muccio walks listeners through what is working/isn’t working about each pitch, concerns investors have, and provides a follow up months later with the entrepreneur(s) who pitched.

The Andy Stanley Leadership Podcast

Andy Stanley is a pastor and leadership expert, who has spent his career helping businesses, people, and churches build organizations that stand the test of time. Every podcast episode, Andy explores a different area of leadership, from visioneering to creating cultures of continual improvement or collaboration. New episodes only come out about once a month, but they always seem timely for those like myself, wanting to grow in their leadership ability.

Under The Influence — Terry O’Reilly

Marketers and non-marketers alike need to subscribe to Under The Influence. Terry O’Reilly has spent over 30 years in the advertising industry, and does a deep dive into the stories behind some of the brands we know and love (and others that never made the cut). Each episode is centered around a theme, such as “when brands go political” or “a history of gendered marketing”. Terry and his team explore five or six case studies in each episode, which is always brilliantly researched and edited.

Before I was an entrepreneur, Under The Influence was a fascinating look into the world of marketing. The podcast has become even more practical since jumping into the arena myself, as I often apply the lens of my own business to whatever topic O’Reilly is tackling that week. Given the quality of the show, new episodes are only free as podcasts for a limited time before they move onto the iTunes store, so make sure you subscribe to Under The Influence, as it’s not as freely binge-able as the others on this list.

“Success! How I Did It“ & “How I Built This“

I’m going to package these two podcasts together, as their formats are nearly identical. Both sit down with accomplished entrepreneurs and media personalities and dive into their back story, the struggles they had along the way, and the lessons they’ve learned getting to where they are today. How I Built This, produced by NPR, has gathered a wide swath of entrepreneurs from a variety of industries, including the founders behind Patagonia, Southwest Airlines, Ben & Jerry’s, and Instagram. Success! How I Did It doesn’t limit itself to entrepreneurs in the same way, featuring interviews with Tony Robbins, John Sculley of Apple & Pepsi, and Megyn Kelly, among others.

Startup — Gimlet Media

4 years ago, I downloaded the podcast Startup by Gimlet Media, and, thanks to it and other factors, decided that the startup world was one I wanted to be a part of. Season One of Startup chronicles the day-to-day journey of former NPR host Alex Blumberg starting up his own podcasting company.

Blumberg does a remarkable job documenting the glamorous and ugly parts of starting your own business, with all the confidence and self-doubt it brings. From arguments over equity with your co-founders to the upheaval it brings to your family life, Alex recorded it all, as it happened.

Newer seasons have focused on the struggles other businesses have faced, and I haven’t listened to enough of those to weigh in one way or another. But Season One of Startup was an incredible concept, executed perfectly, and I highly recommend it to anyone who is currently building a business, or considering doing so.

Bonus Podcasts

There’s a few other podcasts that are a bit too niche in order to include them above, but I wanted to spread the word about them regardless.

Recode Decode

Hosted by Kara Swisher, Recode Decode sits down with some of the top entrepreneurs and influencers in Silicon Valley to get their thoughts on the current state of tech, its myriad problems, and how to resolve them.

Recode Media

Basically the same as Recode Decode, but for the media industry. Hosted by Peter Kafka, this podcast is less “interviews with prominent media figures” and more exploring the massive shift that has occured in media over the last 15 years, and where it’s headed.

Vanity Fair’s Inside the Hive

This podcast, like many, tends to gravitate towards “This Week in Trump” more than I’d like, but explores how the political situation down in the States affects big tech, and how big tech (like Facebook and Twitter) affects the political situation down in the States.

The Tim Ferriss Show

I think it’s unlikely there’s many people reading this unfamiliar with Ferriss, but just in case, he sits down with well-known entrepreneurs, authors, directors, businesspeople, and anyone else ‘interesting’. He podcasts often, and runs the gamut on guests, so my tendency is to not subscribe to his podcast, but instead check in once a month and download the interviews I’m interested in.

The Art of Meaningful Work

This podcast is a friend of mine’s — Ernest Barbaric. Ernest has been exploring side projects, counter-cultural thinking, and how to leave a legacy both professionally, and as a hobby, for years. If you’re trying to connect the work you do to the larger narrative of your life, I’d recommend checking his podcast out.

There you have it — I’m curious: what are your guiding principles when choosing podcasts or media content? Are there some I’m missing? Let me know in the comments; I’m always hunting for better, more practical content.