Guide to the Top Podcasts for Entrepreneurs & Small Business Owners (2020-21)


In some ways, today’s entrepreneurs and small business owners have it easy. A booming market of podcasts has made it possible to access the thoughts of the most successful entrepreneurial minds. Whether you’re thinking of starting your first business, looking for ways to scale up one you’ve already gotten off the ground, or trying to figure out what project to leap to next, there are thousands of hours of quality content out there to provide you the insights you need.

Not all entrepreneurial podcasts are created equal, however. Some are nothing but thinly-veiled marketing schemes for overpaid coaching services, while others contribute little more than feel-good schlock. But sprinkled throughout the massive number of offerings, listeners can find some true unicorns: podcasts that dive deeply into the world’s most successful startups, foster nuanced conversations between the industry’s thought leaders, or give a master class in entrepreneurship that literally meets Ivy League standards.

To get a look at the top podcasts for entrepreneurs and small business owners, check out our guide below.

How I Built This

Hosted by NPR’s Guy Raz, How I Built This is a podcast about innovators, idealists, and entrepreneurs. In each episode, Raz invites his guests to talk about the movements they’ve built, walking the listener through the entire origin story from start to finish.

These stories aren’t dry business cases, either, with the stories often touching on the personal and logistical details that come with starting a disruptive new venture. Previous guests have included the founders of Instagram, Airbnb, VICE, Lyft, Wikipedia, and practically any other successful startup you can think of.


Hosted by Alex Blumberg and Lisa Chow, StartUp is a podcast about starting businesses. But, as with most shows under the Gimlet Media umbrella, the topic is approached in a truly creative fashion. Starting in 2014, the entire first season covered the origins of Gimlet Media itself. The following seasons have either put the spotlight entirely on another company or featured a unique company in every episode.

The stories in StartUp aren’t as flashy as the ones covered in other entrepreneurship podcasts, but they often feel more personal, more relatable, and more real. In 2019, the podcast one again returned to the subject of itself, focusing on the sale of Gimlet Media to Spotify.

Masters of Scale

Hosted by LinkedIn co-founder Reid Hoffman, Masters of Scale is an entrepreneur’s dream come true: the industry’s best and brightest discussing the mechanics behind how an idea grows from zero to hundreds of millions of users. Each episode begins with a soft theory of how to scale and from there, Hoffman’s case studies play out like detective stories, complete with brainstorming “Notes to Self” recorded outside of boardrooms.

Masters of Scale is also the first American podcast to commit to the concept of gender balance for its guests. Previous episodes have featured Sheryl Sandberg of Facebook, Reed Hastings of Netflix, and Arianna Huffington of Thrive.

This Week in Startups

One of the longest-running podcasts on startups and angel investing, This Week in Startups brings entrepreneurs the news they want. Founder Jason Calacanis has been ahead of the entrepreneurship curve for what feels like ages: from being part of the dot-com boom, to acting as an early angel investor, to nabbing the enviably simple Twitter handle of @jason.

Each week, Calacanis and a rotating panel of experts catch up on the best, worst, and most interesting stories in entrepreneurship, relating strategies for starting your own company or managing a team. There are plenty of insights in each episode, and, having been started in 2009, This Week in Startups offers listeners over a decade of archived episodes to choose from.

Planet Money

To be a successful entrepreneur, one has to understand how the complex machinery of the national economy works—and that’s precisely the wisdom that Planet Money, an NPR podcast, seeks to impart.

Initially launched in 2008 to explain the financial crisis that would lead to the Great Recession, the podcast utilizes abridged narratives to explain complicated economic topics to non-expert audiences. In over 1,000 episodes, it’s covered everything from unions to the Federal Reserve to the impacts of a global pandemic on the startup scene. In 2016, Planet Money earned a Peabody Award for its coverage of the Wells Fargo account fraud scandal.

The School of Greatness

Becoming a successful entrepreneur requires healthy doses of motivation and inspiration, and those are the main subjects of The School of Greatness.

Hosted by former football pro Lewis Howes, the podcast has racked up over 100 million downloads from listeners who are interested in the definition of greatness, and how people achieve it. Over 1,000 episodes, Lewis has invited guests to share inspiring stories about entrepreneurship, relationships, health, and mindset. Previous guests have included journalist Guy Raz, self-help guru Tony Robbins, and tennis pro Maria Sharapova.

The Tim Ferriss Show

Love him or hate him, Tim Ferriss reignited a generation’s appetite for entrepreneurism with his best-selling book, The 4-Hour Workweek. Since then, his influence on the world of entrepreneurship and small business has been unignorable to the point that his critics have occasionally maligned and praised him in the same breath.

The Tim Ferriss Show varies widely in its subject matter—entrepreneurship, books, psychedelics, creative writing, and zen—but the moral of the story is often one of self-empowerment and challenges overcome. Previous guests have included Marc Andreessen, Peter Thiel, and Tony Robbins.

HBR IdeaCast

You don’t have to go to Harvard Business School to listen in on the conversations that top business leaders are having. Hosted by senior editors of the Harvard Business Review, IdeaCast brings its listeners weekly insights on what matters to modern business.

Since its launch in 2006, the podcast has covered subjects such as creating more resilient supply chains, future-proofing your business model, transitioning to subscription-based sales models, and how to drive social change with marketing. Previous guests have included Oprah Winfrey, Google’s Eric Schmidt, and Square’s Jim McKelvey.

The a16z Podcast

Listeners of The a16z Podcast get inside the minds of Marc Andreessen and Ben Horowitz, founders of top venture capital firm AH Capital Management (once known as Andreessen Horowitz, and abbreviated as a16z).

Covering everything tech-related—from TikTok, to cryptocurrency, to emojis, to quantum computing—the hosts curate nuanced conversations around where the tech industry is headed. Interviews with startup founders and industry analysts provide insights applicable to every level of entrepreneur. For a firm with $12 billion in assets, the podcast is remarkably generous with its wisdom.

How to Start a Startup

It’s not a podcast per se, but the 20 virtual lessons in How to Start a Startup might as well be required listening for today’s entrepreneurs. Originally presented as a series of lectures at Stanford University, Sam Altman and his colleagues at Y Combinator have recorded what amounts to a one-stop-shop for those seeking to understand the fundamentals of becoming an entrepreneur.

Topics cover each stage of the process, from evaluating ideas, to securing funding, to managing teams, to building for enterprise. For those looking to become successful entrepreneurs, How to Start a Startup is a no-brainer investment.

Matt Zbrog
Matt Zbrog

Matt Zbrog is a writer and freelancer who has been living abroad since 2016. His nonfiction has been published by Euromaidan Press, Cirrus Gallery, and Our Thursday. Both his writing and his experience abroad are shaped by seeking out alternative lifestyles and counterculture movements, especially in developing nations. You can follow his travels through Eastern Europe and Central Asia on Instagram at @weirdviewmirror. He’s recently finished his second novel, and is in no hurry to publish it.

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