10 Most Entertaining Business Podcasts

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10 Most Entertaining Business Podcasts

In this article, I list down 10 best business podcasts that are just as entertaining as they are informative.

I know what you’re thinking: Entertainment and business don’t blend well together.

The general consensus is that business podcasts are “boring” and “uninteresting.” In other words, in terms of podcast categories, they’d probably be at the very end of the spectrum of entertainment.

But this list of best business podcasts is here to prove otherwise. The podcasts featured here can easily give mainstream podcasts like This American Life and Armchair Expert a run for their money.

So without further ado, here are the 10 most entertaining business podcasts you should listen to. If you need more recommendations, you can check the “Honorable Mentions” section to see 10 more entertaining and binge-worthy business podcasts.

10 Most Binge-Worthy Business Podcasts

1. Business Wars

Business Wars Podcast: List of Best Business Podcasts

Hosted by: David Brown (a podcast by the Wondery Podcast Network)

The Wondery podcast network has some of the best business podcasts and Business Wars, hosted by veteran radio journalist David Brown, is the best and most entertaining business podcast of the whole lot.

Business Wars gives you the unauthorized, real story of what drives competing companies and their leaders, investors, and executives to new heights or ruin. The podcast covers some of the most intense corporate (and brand) rivalries — from Coke vs Pepsi to Netflix vs Blockbuster to XBox vs Playstation.

Business Wars Episode List

Each episode is around 30 minutes long and each brand rivalry is given a multi-episode treatment. Since the subject of the podcast is so interesting, it will keep you on the edge of your seat and before long, you’ll find yourself binge-listening to multiple episodes in the series.

My personal favorite is Netflix vs Blockbuster – an eight-part series that dives deep into the rivalry between Netflix and now-defunct Blockbuster.

Launched in 2018, Business Wars quickly grew to be one of the most popular podcasts on Apple Podcasts. Fast forward to today, the podcast has had over 60 seasons and continues to have a large fanbase.

But it’s not just the brilliant storytelling ability of David Brown that keeps you hooked to this podcast. It’s also the fact that there are so many lessons to be learned from each business rivalry. If I could recommend just one business podcast from this list that’s equal parts entertaining and informative, it would be Business Wars.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

The below episodes have multiple parts.

2. Bad Blood: The Final Chapter

Bad Blood: The Final Chapter

Hosted by: John Carreyrou

Elizabeth Holmes had everything going for her. Her blood-testing startup Theranos was valued at over $9 billion and she was being hailed as the world’s youngest self-made female billionaire. And then it all came crashing down when it was revealed that her blood-testing technology didn’t really work.

To make it worse, Holmes had been lying to investors, doctors, and patients about the capabilities of her technology. Worse still, she had been using a wide range of intimidation tactics to silence critics, both from inside and outside her company.

Hosted by John Carreyrou, the WSJ reporter who first broke the Theranos scandal and the author of the brilliant book Bad Blood, this podcast delves into the court case against Elizabeth Holmes and the different scenarios that led to Holmes’ downfall.

Carreyrou breaks down every little detail concerning the Theranos scandal, from Holmes’ relationship with mainstream media to Silicon Valley’s fake it-till-you-make it culture that enabled Holmes to defraud investors and get away with her outrageous lies.

If you liked Carreyrou’s book Bad Blood, then this podcast is a must-listen. Even if you haven’t read the book yet, this podcast will reveal everything you need to know about the Theranos scandal and her subsequent trial that finally held Holmes accountable for her crimes.

Side note: This podcast pairs well with The Dropout, another podcast that covers the rise and fall of Theranos and Elizabeth Holmes. You can find more details about this podcast in the “Honorable Mentions” section.

Listen on: Apple Podcasts | Spotify

My 3 Favorite Episodes

3. WeCrashed: The Rise and Fall of WeWork

WeCrashed Podcast

Hosted by: David Brown (a podcast by the Wondery Podcast Network)

WeCrashed is a six-part podcast series about the rise and fall of WeWork, a company that was once valued at $47 billion dollars. WeWork’s eccentric founder Adam Neumann was able to attract billions of dollars from top-notch investors around the world. He was on the verge of creating a global real estate empire.

All that changed when WeWork decided to go public. WeWork’s disastrous IPO in 2019 unravelled a web of controversies and deceit that the company was embroiled in. As Prof Galloway, host of the Pivot podcast, puts it, “WeWork tried to turn chicken shit into chicken salad.”

For a comprehensive understanding of the WeWork scandal, you must tune in to the WeCrashed podcast. The podcast is hosted by David Brown, who also hosts the super popular business podcast Business Wars (see #1 in this list). In fact, this podcast became so popular that it’s now being adapted into a limited TV series of the same name, starring Jared Leto as Adam Neumann and Anne Hathaway as Rebecca Neumann.

WeWork’s rise and fall is a cautionary tale for ambitious entrepreneurs. It reveals the amount of damage a narcissistic leader can do to an organization.

For me, the most infuriating part of the WeWork story was Adam Neumann’s settlement. He walked away with $1.7 billion after he lost the company millions of dollars every week and the company fired 8,000 employees across locations.

Side note: If you end up liking this podcast, please check out the book Billion Dollar Loser by Reeves Wiedeman. This business thriller offers an in-depth look at all the insanity that transpired at WeWork until its disastrous IPO. It was one of the best business books I read in 2021.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

4. Bad Bets

Bad Bets Podcast - List of Best Business Podcasts

Hosted by: John Emshwiller and Rebecca Smith (a podcast by the Wall Street Journal)

The Wall Street Journal’s Bad Bets is a podcast series that explores big-business dramas that have had a big impact on the world. It’s a relatively new series and the first season deals with the Enron scandal which many consider to be the mother of all corporate frauds.

Hosted by Wall Street Journal reporters John Emshwiller and Rebecca Smith, the show features interviews from key players who had a front row seat to the big egos and unchecked power within Enron.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

5. Legal Wars

Legal Wars Podcast - List of Best Business Podcasts

Hosted by: Hill Harper (a podcast by the Wondery Podcast Network)

This critically acclaimed podcast by the Wondery Podcast Network deep dives into some of the most famous court cases in American history, from Hulk Hogan’s lawsuit against Gawker that put the company out of business, to ‘Pharma Bro’ Martin Shkreli’s sentencing for securities fraud. In addition to all the legal drama, you’ll also hear about the real-world implications these cases had on the modern society.

Hosted by actor and Harvard Law School graduate Hill Harper, each court case is given a multi-episode series just like Wondery’s other podcast Business Wars (see #1).

Legal Wars Episode List

I’d highly recommend you start with the Hogan v Gawker series as it’s the best and most entertaining of the lot.

Side note: To learn more about the Hogan vs Gawker case, I’d also recommend you read the book Conspiracy by Ryan Holiday which covers this case in greater detail. It’s one of the best business thriller books I’ve ever read and it’s hard to put down once you start reading it.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

6. Where It Happens

Where It Happens Podcast - Best Business Podcasts

Hosted by: Sahil Bloom and Greg Isenberg

How do you determine whether NFTs are just short-term fads or here to stay? Is Web3 the internet of the future? Which of today’s trends will shape the opportunities of tomorrow? If you’ve pondered over these questions, then this podcast is for you.

Hosted by Sahil Bloom and Greg Isenberg, Where It Happens puts you in the middle of the conversation of innovations and opportunities and gives you access to a community that helps you take advantage of what’s next.

For an introduction to this podcast, check out episode 8 which features an interview with Alexis Ohanian, founder of Reddit, where he shares his early lessons from Reddit and why he’s betting big on Web3.

Listen on: Apple Podcasts | Spotify

My 3 Favorite Episodes

7. We Study Billionaires

We Study Billionaires Podcast - List of Best Business Podcasts

Hosted by: Stig Brodersen and Trey Lockerbie

As the name suggests, this podcast interviews and studies famous financial billionaires. From Warren Buffet to Jeff Bezos to Howard Marks, We Study Billionaires will teach you how to apply the billionaires’ investment strategies in the stock market.

The podcast has been around since 2014, so there are a lot of episodes to go through. I’d recommend starting with the first episode of this podcast, which delves into Warren Buffet’s investment approaches.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

8. Business Movers

Business Movers Podcast: List of Most Entertaining Business Podcasts

Hosted by: Lindsay Graham (a podcast by the Wondery Podcast Network)

Business Movers is a weekly podcast that covers the true stories of the brilliant but all-too-human businesspeople who risked it all to reach new heights. It’s hosted by Lindsay Graham, the Webby Award-winning host of the podcasts American History Tellers and American Scandal.

In the podcast, Graham explores the triumphs, failures, and ideas that transformed our lives, ranging from how Howard Schultz saved Starbucks from the brink of disaster to the collapse of Lehman Brothers.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

The below episodes have multiple parts.

9. Founder’s Journal

Founder's Journal Podcast: List of Best Business Podcasts

Hosted by: Alex Lieberman (a podcast by Morning Brew)

This is a podcast hosted by Morning Brew. If you’re not in the know, Morning Brew is a free daily newsletter that covers business and tech news. It’s one of the most popular business newsletters out there with over 3 million subscribers around the world.

Morning Brew’s motto has always been “stay informed and entertained.” The same principle applies to their podcast Founder’s Journal, which is hosted by Morning Brew’s co-founder Alex Lieberman.

Lieberman treats the podcast like his personal audio diary where he shares the tools you need to think better and build a better business and product. Lieberman’s favorite productivity method, which he explains in episode 298, really resonated with me and I was able to take some pointers from it.

Listen on: Apple Podcasts | Spotify | Website

My 3 Favorite Episodes

10. Web3 Breakdowns

Web3 Breakdowns Podcast: List of Best Business Podcasts

Hosted by: Eric Golden

Consider yourself a crypto enthusiast? Then this is the podcast for you. Web3 Breakdowns offers a good primer on complex Web3 topics, including popular NFT projects, crypto assets, blockchain-based protocols, and businesses being built with Web3 architecture.

The podcast features a series of conversations with innovators, founders, investors, and influencers in the world of decentralized internet. It’s the best business podcast to tune into if you’d like to expand your knowledge and understanding of Web3’s emerging ecosystem.

Listen on: Apple Podcasts | Spotify

My 3 Favorite Episodes

Related: 22 Best Cryptocurrency Podcasts

Honorable Mentions: 10 More Entertaining and Binge-Worthy Business Podcasts

If the above listed business podcasts aren’t enough to quench your thirst for entertainment, here are 10 more binge-worthy business podcasts.

  • The Wall Street Journal Podcast – This news podcast by WSJ covers the most important stories, explained through the lens of business. Short episodes (usually under 20 minutes) come out every day on weekdays and hosts Kate Linebaugh and Ryan Knutson always add their unique perspective while covering a wide range of interesting news topics.
  • The Dropout – If Bad Blood:The Final Chapter (see #2) isn’t enough to unpack the Theranos saga, then I’d highly recommend The Dropout, which covers Elizabeth Holmes’ trial in detail. It features exclusive interviews with former Theranos employees, investors, and patients, and the never-before-aired deposition testimony of Elizabeth Holmes, and those at the center of the Theranos story.
  • Pivot – Hosted by popular tech journalist Kara Swisher and NYU Professor Scott Galloway, Pivot covers the biggest news stories in tech, business, and politics. It’s easily one of the best business podcasts around. But what makes it entertaining is the enjoyable banter between Swisher and Galloway.
  • Secret Sauce – Co-hosts Samuel Donner and John Frye take you behind the scenes of the most innovative leaders, trailblazing companies, and thriving cultures to learn what they have done to become a success. The episodes range from from how Jony Ive and Steve Jobs worked together to create some of Apple’s most iconic products, to how two design students overcame the odds to create Airbnb.
  • American Innovations – Hosted by bestselling author Steven Johnson, American Innovations uses immersive scenes to tell the stories of the scientists, engineers, and ordinary people behind the greatest discoveries of the past century.
  • Considering the Scam – As you can guess from the podcast title, this is a podcast that covers scams, scandals, heists, and swindles. This 12-episode podcast series is now over, but you can check it out to learn more about fascinating subjects like the origin of Ponzi schemes and the infamous Lufthansa heist.
  • The Next Big Idea – Hosted by Rufus Griscom, and featuring special guests like Malcolm Gladwell, Susan Cain, Adam Grant, and Daniel Pink, The Next Big Idea brings you groundbreaking ideas with the power to change the way you see the world.
  • Noah Kagan Presents – This podcast by the founder of AppSumo is insightful and entertaining. Noah’s passion for his craft and entrepreneurship is infectious. Highlights include the episodes “9 Best Side Hustles You Can Start From Home,” “How I Made My First Million Dollars,” and “How Ali Abdaal Grew a 700K Subscriber YouTube Channel While in Med School.”
  • This Old Marketing – Hosts Joe Pulizzi and Robert Rose, two well-known content marketing experts, talk about the latest content marketing trends, and discuss how businesses can use content to attract and retain customers. Like Pivot, the banter between these two podcast veterans makes this podcast an enjoyable listen.
  • The GaryVee Audio Experience – GaryVee has an entertaining personality. Which is why I’d feature his podcast on this list because he can even make a boring topic interesting to listen to. Here’s a caveat though: Take everything GaryVee says with a pinch of salt. Some of his recent takes and predictions have been outrageously bad and problematic. And his boisterous, over-the-top personality can be off-putting at times for some listeners.

Final Thoughts

So these are my picks for the most entertaining business podcasts. Did I miss out on any of your favorite business podcasts that are not just informative, but also entertaining? Let me know in the comments section below. I’d love to check out some of your recommendations.

If you’d like more podcast recommendations, check out these lists as well:

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10 Most Entertaining Business Podcasts
Sandeep Mallya is the Founder & CEO of Startup Cafe Digital, an award-winning digital marketing agency in Bangalore, India. He is an active member of the startup community, having worked with several early-stage startups and accelerators. 99signals is Sandeep's online marketing blog. The blog currently features 200+ in-depth articles, how-to guides, and hacks on a wide range of online marketing topics such as SEO, social media marketing, content marketing, blogging, and more.

1 COMMENT

  1. Sharing here my list of the channels I listen to:

    1. The Tim Ferriss Show
    2. How I Built This with Guy Raz
    3. Masters of Scale with Reid Hoffman
    4. TED Talks Business
    5. The Bottom Line with Barry Ritholtz

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