Entrepreneurship is certainly a challenge, but the best podcasts about it can help you navigate that journey with more confidence.

Using a mixture of behind-the-scenes conversations and interviews, these podcasts should answer some of your key questions, like how did others get where they are? What pitfalls should you avoid along the way? And many others that people with first-hand experience can shed some light on.

It’s impossible to avoid making mistakes. Making business-destroying mistakes, though, is very avoidable with the right information at your fingertips. Podcasts can deliver that information!

Our list features podcasts about entrepreneurs rising beyond all the trials and tribulations that come with starting a business. Getting inspiration from those entrepreneurs is, in some ways, the most important part of the podcasts. You’ll need plenty of willpower and inspiration to succeed in starting and growing your business!

After months of listening to entrepreneurship podcasts, we’ve narrowed down the list to these 5 best podcasts about entrepreneurs to help you along your way:

Best Overall Podcast About Entrepreneurs: How I Built This

The How I Built This podcast masterfully shows all the ins and outs of taking your idea and turning it into a successful business. For that, it takes the title of the best entrepreneurial podcast.

It trumps other podcasts by showing the grittier side of entrepreneurship. Out of all the hurdles people face when establishing a business, very few of them actually get mentioned once the business has found success. How I Built This dives into how the most successful entrepreneurs found their way to the top, hurdles and all.

How I Built This wins out based on its practicality alone, but that’s not the only thing it has going for it. The podcast is in a guest interview format and features companies from Roblox to Men’s Warehouse to smaller businesses you’ve probably never heard of. The host, Guy Raz, handles them all with a genuine interest in their stories to ultimately answer the question, “How did you build that?”

With such a wide range of interviewee industries and stories, everyone has something to learn from the podcast.

Episodes in How I Built This range from 45 to 90 minutes. The longer episodes enable Guy to take those deeper dives and really establish what the journey was like for the entrepreneur in question. Of course, the longer episodes can also make listening to How I Built This feel a little tedious if you aren’t super into the company being discussed. 

Overall, though, How I Built This is an incredible entrepreneurial podcast with very few downsides. We recommend it to anyone with some time on their hands and the desire to learn.

Listen on Spotify here and on Apple Podcasts here.

Best For Bootstrappers: Startups for the Rest of Us

Funding is the name of the game for most entrepreneurs, but it’s always in short supply. Bootstrappers end up being the majority of entrepreneurs because of that. Startups for the Rest of Us captures the energy, struggles, and wisdom that bootstrappers have in an easy-to-consume format.

Startups for the Rest of Us is at the peak of practicality for entrepreneurs using what they have to do when they can. Because of that, listeners find the interviews to be extremely relatable. It feels real, and that kind of real knowledge is valuable for everyone, not just so-called bootstrappers.

Rob Walling hosts the show with a single concept in mind: highlighting the struggles and successes of startups that made it from the bottom to the top. This formula means viewers will almost always have actionable takeaways after watching each episode. For episodes that are only 25 to 50 minutes, Walling does a great job of asking the right questions and condensing the material to give listeners the best insights.

The thread connecting all of the different interviewees hosted on the shows is that they don’t receive outside funding. You’ll also find that there are other similarities between their journeys. Startups for the Rest of Us shows the inherent vulnerability and difficulty in bootstrapping a business with piercing interview questions.

There is a weak spot in the podcast, and that’s the industries it covers. Startups for the Rest of Us exclusively covers SaaS companies. Many bootstrappers are in SaaS or related industries, but that isn’t always the case.

Still, Startups for the Rest of Us has applicable information for every entrepreneur in every industry. You won’t be disappointed by their insights into what it takes to bootstrap.

Listen to it on Spotify here and Apple Podcasts here.

Best for Indie and Hobbyists: Indie Hackers

Indie Hackers is the best entrepreneurial podcast there is for indie startups. Hobbyists and ‘indie hackers,’ as the podcast calls them, often have a calling to start their own businesses. But, how do you get from a cool idea or a hobby to an online startup that actually brings in a profit?

That question is exactly what Indie Hackers answers. Courtland Allen interviews entrepreneurs who don’t follow the ‘classic’ path toward entrepreneurship. The featured guests won’t be the same as on podcasts like How I Built This. Their philosophies won’t even be reminiscent of those that big-name entrepreneurs like Peter Thiel have.

Courtland Allen promotes the idea that anyone can start a business, with or without following a specific outlined route. The smaller entrepreneurs you’ll listen to have insights on starting online businesses while still working 9-5 jobs, or starting a business from side projects. Businesses don’t have to be full-time, and if that’s what you’re hoping for, Indie Hackers is the podcast for you.

The episodes are between 30 and 60 minutes long. There is a decent variety in length and startup industry, so you can pick and choose when and what you want to listen to. Indie Hackers is all about creativity and compact ideas that are profitable, interesting, and rarely revolutionary. Let’s be real–-most entrepreneurial ideas fall into that category.

For the layman, the hobbyist, and anyone with a side project they want to level up, Indie Hackers will provide sharp commentary and fascinating stories.

You can listen on Spotify here and on Apple Podcasts here.

Best Behind the Scenes: The Pitch

Lots of podcasts advertise themselves as being behind-the-scenes looks into entrepreneurship. Most of them stick to the guest interview format. Josh Muccio’s The Pitch shows entrepreneurs pitching ideas to real investors, making it the best behind-the-scenes look at entrepreneurship.

It’s difficult to find investors that will buy into your vision. With that being the reality, pitches on this podcast rarely get funding. But, with every episode, Josh and the investors help entrepreneurs hone their ideas and level up their businesses.

By listening to the pitches, you can learn more about how you can sell your next big idea. What makes a business worthy of investment and what makes a business doomed to fail? Josh offers commentary on why businesses end up falling into either of those categories.

The Pitch is also a great podcast for slipping into your lunch break, short commute, or evenings before bed. The episodes are very bite-sized, lasting only 20-30 minutes. It still manages to tell meaningful stories and give genuine feedback within that short timeframe.

In addition to the usual content, The Pitch sometimes cuts between actual pitches and interviews. Usually, the interviews are with founders about hot topics in the current entrepreneurial space. For example, a recent episode debated whether or not you really need a software patent for your invention.

All in all, The Pitch is like a better, podcast version of Shark Tank. New and old entrepreneurs can truly take something out of the feedback given in The Pitch. Since it’s all about early-stage investing, it’s a great listen for entrepreneurs who are still incubating their ideas.

Catch it on Spotify here and Apple Podcasts here.

Business man in suit holding a ball pitch
Regardless of if you have an interest in entrepreneurship or are starting a business yourself, there is much knowledge to be found in these podcasts.

Best for Idea Development: That Will Never Work

It can be hard to hear people tell you that your startup idea just isn’t all the way there, but it’s necessary to hear it when you’re developing your idea. The That Will Never Work podcast sees host, Marc Randolph, telling his guests just that. That tough love is why this podcast wins for idea development.

Marc challenges the entrepreneurs on his podcast to take an unbiased look at their own businesses. The questions he asks (and forces his interviewees to ask) would make most business owners defensive, but Marc does it in a way that encourages more introspection and less ego.

In most cases, That Will Never Work explores how a business or idea is fundamentally flawed and how to fix it. But, sometimes, there will be ideas featured on the podcast that feel unreasonable, only for their issues to be creatively solved. That Will Never Work will help you grasp the difference between successful ideas and failures, either way.

Even if you’re past the initial idea development phase, you can still learn from Marc’s analysis of business ideas. Pivoting will always be a crucial part of business creation. Marc will show you how to stay agile while battling your ego to make businesses that will really work.

Each episode is between 25 to 40 minutes. Occasionally, listeners feel like there needs to be more time. Other episodes feel like they drone on for a little too long. But the majority of the episodes are the perfect length for what needs to be covered.

If critiquing your idea development process and learning how to pivot is your priority (and it’s certainly a good priority), That Will Never Work will supplement your entrepreneurial growth perfectly.

Listen on Spotify here and on Apple Podcasts here.

What to Know Before Listening to An Entrepreneurial Podcast

Listening to an entrepreneurial podcast can be a great way to learn more about how to start a business. It can also be a waste of time and brain space if you don’t approach it correctly.

Before you listen to a podcast about entrepreneurs, you should think about a couple of key considerations. Not every podcast episode will be about an entrepreneur in a similar situation as you. Although you can usually learn something from them regardless, it’s important to keep the differences in mind.

Essentially, you might have a very different experience than the entrepreneurs featured on a podcast. Make sure you have a solid grasp on what your own personal shortcomings, challenges, and strong points are before you set expectations.

You might also want to take a couple of notes while listening to an entrepreneurial podcast. There can be amazing takeaways from each episode, but you won’t be learning anything unless you apply those takeaways. We suggest writing a sentence or two after each episode about things you want to remember and saving that document somewhere you’ll remember.

That way, you can really make the most out of the best podcasts about entrepreneurs.

The 5 Best Podcasts About Entrepreneurs FAQs (Frequently Asked Questions) 

What should an entrepreneur listen to?

There are tons of podcasts for entrepreneurs to listen to and learn from. Some of the best include:

  • How I Built This
  • Indie Hackers
  • Startups for the Rest of Us
  • The Pitch
  • That Will Never Work

What is one business podcast you'd recommend for a business owner?

We recommend business owners listen to the podcast, How I Built This. In the podcast, host, Guy Raz, interviews founders to glean key insights into how they managed to get where they are today. The podcast covers a wide range of industries, with most businesses being mid to large-sized. Still, there are some smaller businesses featured.

No matter the size, How I Built This is a great way to learn how to run your business smoothly and help it grow.

What is the highest paid entrepreneur?

The highest-paid entrepreneur is Bill Gates, who makes $4 billion every year. He founded Microsoft corporation in 1975 alongside Paul Allen, and although it took time, his business eventually became one of the largest in the world. His net worth is approximately $88.8 billion as of today.

Who is the youngest successful entrepreneur?

One of the youngest successful entrepreneurs is Maddie Rae and her craft business. She catapulted to popular success at the age of 13 years with Maddie Rae’s slime glue, a popular product amongst tweens just like her.

Maddie Rae is far from the only successful young entrepreneur. Mikaila Ulmer, for example, founded Me & the Bees lemonade and was also enjoying entrepreneurial success by age 13.

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More from History-Computer

  • Indie Hackers (1970) https://www.indiehackers.com/podcasts
  • The Pitch (1970) https://www.thepitch.show/#show-tab-picker
  • Marc Randolph Available here: https://marcrandolph.com/podcasts/
  • Startups for the Rest of Us (1970) https://www.startupsfortherestofus.com/
  • Apple Podcasts (1970) https://podcasts.apple.com/us/podcast/how-i-built-this-with-guy-raz/id1150510297
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  • Apple Podcasts (1970) https://podcasts.apple.com/us/podcast/that-will-never-work/id1550777106