best small business podcast

The 10 Best Entrepreneur Podcasts

Anne Shaw

Whether you consider yourself a small business owner or an entrepreneur (what is an entrepreneur, anyway?), you wear a lot of hats. And because of that, you should always be learning. What better way than listening to the best podcasts for business owners? After all, podcasts are infinitely portable. You can listen to them anywhere—on the plane, in bed, while running, etc.—as long as you have a mobile device and headphones.

The best entrepreneur podcasts present a convenient way for business owners to learn lessons from other entrepreneurs who’ve already walked similar paths and arrived where they want to go. To hear from the best business experts, get your favorite entrepreneur podcast queued up and ready to play every time you commute or go on a supply run. You’ll be amazed at how much you learn and the exciting ideas they’ll inspire. With so many options out there, locating good content can feel overwhelming. Don’t stress—we’ve narrowed it down for you. Below are some of our top recommendations.

1. The Small Biz Ahead Podcast

Among the best entrepreneur podcasts is The Hartford’s very own, Small Biz Ahead Podcast. We offer practical and timely advice to small business owners. Give it a listen to learn everything from digital marketing tips and cyber security best practices to selling during the pandemic and learning what The American Jobs Plan means for small businesses and more.

2. The Tim Ferriss Show

Author of The 4-Hour Workweek, entrepreneur Tim Ferriss hosts The Tim Ferriss Show podcast. His guests come from various industries, so Ferriss covers a wide range of topics that have garnered him 10,000+ 5-star reviews and 700 million downloads. While not all his guests are business owners (hi, Jane Goodall and Arnold Schwarzenegger), Ferriss makes a point to highlight relatable takeaways that anyone can apply in life and business.

3. Eventual Millionaire

Host Jaime Masters is a speaker, business coach and online entrepreneur. She also wrote a book by the same name that walks readers through validating and acting on ideas to then build a business. In her weekly podcast, Eventual Millionaire, Masters interviews hundreds of successful CEOs and entrepreneurs about their lessons learned while making their first million dollars. Her goal: to help listeners live a better life and make sound financial decisions, leading them to become eventual millionaires.

4. This Week in Startups

Want to stay in the know? Billed as “the most interesting, outrageous and illuminating stories from the world of entrepreneurship,” This Week in Startups is one of the best startup podcasts. The dynamic weekly entrepreneur podcast covers timely stories of exciting startups. It will be your best friend—one who always dishes up the latest news. Host Jason Calacanis welcomes an engaging rotation of co-hosts, so listen regularly to stay current on your startup news and gain valuable insights about how other entrepreneurs operate their businesses.

5. How I Built This

Looking for an inspiring entrepreneur podcast? Guy Raz of National Public Radio (NPR) tells the stories behind highly successful entrepreneurs, innovators and idealists (and the companies or movements they built) in How I Built This. Thanks to its narrative format, many find How I Built This to be an engaging way to learn valuable lessons about what works and what doesn’t while building a business.

6. Startup

Hosted by Alex Blumberg and Lisa Chow, the first season of Startup offers a behind-the-scenes scoop on the founding and growth of Gimlet Media, the podcast’s own publisher. It even inspired its own sitcom, NBC’s Alex Inc., starring Zac Braff. With its engaging documentary-style format, the podcast continues to explore entrepreneurial life and offers valuable insights to small business owners.

7. Entrepreneurs on Fire

John Dumas hosts Entrepreneurs on Fire, a daily entrepreneur interview podcast. In each episode, his goal is to get to the heart of what makes each entrepreneur tick. By motivating current and aspiring entrepreneurs to pursue their own goals, he hopes to help them achieve their desired lifestyle and financial freedom.

8. The School of Greatness

Serial entrepreneur Lewis Howes hosts The School of Greatness, one of the most popular podcasts of all time. With more than 150 million downloads, this podcast consistently ranks among the top business and self-development podcasts. Howes’ guests range from successful entrepreneurs to athletes to vocalists. In every episode, he delves into what makes extraordinary people great and how listeners can implement these lessons in their own lives.

9. The GaryVee Audio Experience

An incredibly successful entrepreneur, Gary Vaynerchuk comes from humble beginnings. Part of an immigrant family, “GaryVee” joined his family business as a 14-year-old and later transitioned it to one of the first eCommerce platforms for alcohol — before eCommerce was cool. Thanks in part to this move, GaryVee grew the business from $3 million to $60 million during his tenure. Since then, he’s been a prolific entrepreneur and angel investor. Listen to The GaryVee Audio Experience, one of the most popular entrepreneur podcasts, for his insights.

10. Smart Passive Income (SPI)

Host Pat Flynn lost his architecture job during the Great Recession. In his words, he then “learned about online business because [he] had to.” These days, he runs SPI, which publishes several podcasts. Its flagship Smart Passive Income podcast features interviews with marketing experts, entrepreneurs and eCommerce specialists. Each episode explores an expert guest’s strategies for developing sustainable incomes in a compelling, listening-friendly format.

Top Podcast Wrap up

Becoming a successful small business owner requires continuous development and learning. Podcasts offer a handy way to learn from the best. Listening to the best entrepreneur podcasts can help you discover new ideas around how to grow a business. You can also learn ways to inspire and lead your people and feel encouraged when things get tough. For many, nothing is more satisfying than being your own boss. So, we hope one (or a few!) of these entrepreneur podcasts helps you navigate growing and scaling your own business. As you do, make sure you’re covered with the proper small business insurance.

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7 Responses to "The 10 Best Entrepreneur Podcasts"
    • Don Davies | February 20, 2022 at 6:11 am

      Smart Passive income, and the one by Keion Henderson, https://www.keionhenderson.com/church-podcast surprisingly not on this list are my top best business podcasts of all time! It has really helped me in navigating my entrepreneurial journey!

      • Small Biz Ahead | February 21, 2022 at 12:43 pm

        Thank you for sharing, Don! We appreciate the comment.

    • Zenobia | January 26, 2022 at 6:29 am

      I started the 10KB Goldman Sacs for Small Businesses . These podcast are like an extra bonus while learning more about growing my business. Thank you!!

      • Small Biz Ahead | January 26, 2022 at 9:31 am

        That’s great! You’re welcome!

    • Michele Kennedy | January 19, 2022 at 4:45 pm

      Another great podcast is Mind Your Business by James Wedmore.

    • Elsa G Garcia | January 19, 2022 at 11:00 am

      Thank you

      • Small Biz Ahead | January 19, 2022 at 3:37 pm

        You’re welcome, Elsa!

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