10 Podcasts About Entrepreneurship Smart, Honest, Unfiltered

Entrepreneurship isn’t just about starting a brand and making millions—it’s everything that happens in between. When you’re your own boss, discipline, resilience, and self-awareness are seriously make-or-break throughout the process. That said, this is why podcasts about entrepreneurship are total gold mines.

When you’re looking for proven strategies that truly work in business, who better to get advice from than trailblazers and innovators who have talked the talk and walked the walk? The Bossticks recently touched on this topic in their episode, “From Stable Career to Creator.” To be successful, you have to be willing to turn failures into opportunities—and take advice from the right people. 

Today, we’re rounding up all of the best podcasts about entrepreneurship—featuring real founders, proven strategies, and lessons you can actually apply to your own business. From thought leaders to global empires, these podcasts offer advice that will help you move your own entrepreneurial needle. Let’s learn, grow, and thrive together!

10 Podcasts About Entrepreneurship Every Founder Should Hear

When you think of starting from the ground up, of course, you need entrepreneurial skills and the skills to execute them. That’s the name of the game—but it’s definitely easier said than done. And just like Lili Aghaei said in THIS episode of DITL, you either have to get with it or get lost. (With love, OBVI.)

Needless to say, everyone’s climbing the ladder of success. It’s the ones who invest their time and energy that cut the line and turn ideas into action. Example A: “The Business Playbook: Tools Every Brand Should Be Utilizing, How to Build a Scalable Company, Securing Funding, & More” from The Dream Bigger Podcast. 

SO! This is your sign to stop scrolling, pull out your Promises to Myself Journal, and lock in.

In this post, we’re telling you what entrepreneurship is at its core—the mindset, skills, and real-world lessons that separate ideas from execution. Then, we’re answering the burning question: “Why is it important to listen to podcasts on entrepreneurship?” (We know you thought it.) And finally, we’ll give you all of the best entrepreneurial podcasts full of successful, been-there, done-that trendsetters. 

What Is Entrepreneurship?

Entrepreneurship is the process of building, growing, and sustaining a business by turning ideas into action—often without a guaranteed outcome. It involves identifying opportunities, taking calculated risks, and creating value through products or services. Basically: risk > reward.

It’s not just what happens at the end, though—and that’s where a lot of people mess up. It’s the everyday involvement, dedication, self-motivation, and passion that drive success. At its core, entrepreneurship includes: 

• Spotting a gap in the market and taking initiative
• Taking calculated risks instead of hoping for the best
• Learning through trial and error—because it can’t always be perfect on the first go-around
• Evolving as the business grows
• Understanding that enthusiasm is the backbone behind motivation

No two journeys look the same, which is why learning from successful founders is so important. And that’s why podcasts about entrepreneurship are totally invaluable. You learn, grow, and remember why you started in the first place—from advice you can’t find in a book or business plan.

Why Listen to Podcasts on Entrepreneurship?

Learn From Real-World Experience

When you want to bea successful entrepreneur, are you gonna take advice from just anyone? NO! Of course not! You’re gonna listen to “From $500 to a Lash Empire: Power Moves & Purpose ft. Yris Palmer” from Khloé in Wonder Land. AKA, you’re hearing from people who have truly gone through all the phases.

Remember, podcasts on entrepreneurship aren’t cut-and-dry conversations. They’re authentic stories full of real-world experiences. It’s like picking the brain of someone living your dream—except they tell you HOW to get there.

Get Actionable Advice You Can Apply Immediately

If you’re trying to figure out how to market successfully, hearing someone say “personalize your brand!” feels useless. You’re probably thinking “… Okay? But how?” Podcasts break down these concepts into bite-sized steps that you can actually feel confident applying to YOUR business.

Take “From Idea to Sephora” from She’s So Lucky, for example. Les interviews the founder of Ami Colé, Diarrha N’Diaye-Mbaye, who shares how intentional content creation can meaningfully build brand identity. No guesswork, no “what-ifs,” just real, actionable advice that’s proven to work.

Stay Motivated Without Burnout

Learning how to turn failure into inspiration is a job in itself—especially as an entrepreneur. But this is where podcasts prove totally invaluable. You’re not the first person to start from scratch, which means you’re also not the first person to overcome setbacks.

This is literally what “Getting Dressed Is a Power Move: Ramy Brook on Confidence, Risk, and Reinvention” from With Whit talks about. Fashion CEO Ramy went from selling tops to scaling brands, realizing how consuming it actually was. But it wasn’t luck that got her through it; it was strategy. And, fortunately, successful people aren’t afraid to tell other entrepreneurs what those strategies are—and how to push through the burnout.

Hear Diverse Perspectives and Business Paths

People think there’s a secret formula to success, and honestly? Not true. Every business venture is unique to the brand, person, and experience. That said, hearing from a diverse group of entrepreneurs reminds you there’s more than one way to build something meaningful. 

In “Essential Moments, Cell Phone Rules, and No Outside Clothes” from DITL, Nicole Walters shares what it’s like being a NYT Best-Selling Author, Emmy-nominated producer, and host of Tell Me More. But then you have episodes like “Agent Nateur’s Jena Covello on the Secrets Behind Clean Beauty” from The Bossticks that explore a totally different avenue of success.

Sure, they’re both totally different stories about the road to achievement. But that’s the thing—both episodes are about prosperity and triumph. And there’s nothing we love more than a badass, successful businesswoman!

Learn on Your Own Schedule

Look, we think that books about business are great—seriously… If you have the time for them. We’re all already booked and busy. And then you add entrepreneurship on top of it? You barely have time for self-care, let alone reading a stack of books about starting a business.

Podcasts let you learn on your time, at your own pace, when you want to. In the car running errands? No problem. Cooking dinner and suddenly feel the pull of toxic productivity? Done. Podcasts about entrepreneurship are the BEST resources because they work for you—on your schedule.

What Are the Best Entrepreneurship Podcasts?

The Bossticks

Lauryn Evarts Bosstick and Michael Bosstick, the brains behind The Bossticks, are the BEST for budding innovators. As successful entrepreneurs themselves, this podcast features interviews with world-class leaders, doctors, celebrities, athletes, executives, and more. 

The goal behind each episode? To offer tangible takeaways and actionable advice. Every conversation is as dynamic as the guests are, making it the perfect listen for every type of entrepreneur. Plus, every conversation is equally entertaining, which is an added bonus.

Start with “Tina Chen Craig on Personal Resilience, Discovering Your Passion, & How to Adapt to Thrive in Life!” It’s candid, inspirational, and designed to spark desire.

How I Built This

Hosted by Guy Raz, How I Built This interviews founders and entrepreneurs to unpack every stage of their success stories. From early setbacks to intense moments of doubt, each episode dives into what it’s actuallylike building a brand.

And here’s why it’s so good: it doesn’t just focus on the end result. The minds behind the world’s biggest brands offer a behind-the-scenes look at the pivotal moments that made them so successful. It’s a candid take on risk, resilience, leadership, and learning as you go. 

Tune into “Advice Line with Neil Blumenthal of Warby Parker” first! Not only is it educational, but it’s also super engaging.

Masters of Scale

Masters of Scale is hosted by Reid Hoffman, co-founder of LinkedIn and a venture capitalist. (TBH, that should tell you everything you need to know—but we’ll continue.) Reid interviews business leaders as they share the strategies and advice that made them what they are today. Think: founders, CEOs, and ambitious forward-thinkers.

Masters of Scale is SO popular among entrepreneurs because its content spans every stage of growth. From Brian Chesky, co-founder of Airbnb, to Mark Cuban discussing the future of AI, this podcast doesn’t shy away from honest conversations about building and scaling a successful business.

Smart Passive Income

In the entrepreneurship world, Pat Flynn from Smart Passive Income is basically royalty. For decades, Pat has been completely transparent about how he’s created multiple passive income streams. The wins, the losses, and every lesson learned in between are for every listener’s taking.

More specifically, though, this weekly podcast is designed to keep creators ahead of the curve through business strategies, income sources, and top marketing tips. From building authority online to productivity tips, Pat shows us you can absolutely build something meaningful without burning out.

Before you start note-taking (because trust us, you will!), tune into “This Is How You Know If You’ll Win or Quit in 2026.”

HBR IdeaCast

Alison Beard, host of HBR IdeaCast and executive editor at Harvard Business Review, is a must-listen for entrepreneurs. This show dives deep into how to think smarter (not harder) about how you run your business. AKA, it’s a total time-saver in the long run. 

Every episode breaks down research-backed ideas, leadership strategies, and real-world insights from top experts worldwide. But here’s why it’s such a sustainable listen: it’s not just about chasing trends, it’s about exploring proven frameworks. If you want your strategy to match your intention? You need to tune in ASAP. 

Listen to “How to Manage – and Motivate – Gen Z.” We think it’ll hit home.

The Tim Ferriss Show

With over 1 billion downloads and 800 interviewed guests, Tim Ferriss from The Tim Ferriss Show REALLY knows what he’s doing. As Tim deconstructs world-class performers, this podcast is equal parts insightful and motivating. (He’s not referred to as the “Oprah of the Radio” for nothin’!)

He doesn’t just want to talk to guests about why they’re successful. He wants to know how they got there and what advice they can offer to listeners. He asks questions about the books they’ve read, how they manage their time, the mindsets they follow, and what their morning routine looks like. Seriously, if you’re looking for a proven starting strategy? The Tim Ferriss Show has it. 

Obviously, you have to start with “Arthur Brooks—Finding the Meaning of Your Life, The Poet’s Protocol, the Holy Half-Hour, and Why Your Suffering is Sacred.”

The GaryVee Audio Experience

Gary Vaynerchuk is an entrepreneur, CEO, investor, content creator, public speaker, and host of The GaryVee Audio Experience. This show is a fast-paced mix of mindset shifts, business strategy, and real-time advice pulled from talks, interviews, and Q&As. So no matter your preferred podcasting style, you can find it here.

Gary’s raw, no-filter approach is one of the many things that make this podcast stand out. He doesn’t sugarcoat the realities of building a business, and that level of honesty? It resonates with entrepreneurs dealing with burnout, growth, and big-picture decisions. 

His episode, “1-Hour of Advice about Sales, Self-Belief, and Winning in Business,” needs to be your first listen.

The Goal Digger Podcast

If you’re a woman navigating entrepreneurship, Jenna Kutcher, host of The Goal Digger Podcast, is exactly who you should turn to. When people talk about success, there’s one thing a LOT of them brush over: fulfillment. You can be successful AF and not be fulfilled. 

But Jenna’s desire is that entrepreneurs find joy, ease, and peace in their goals—not stress. Through honest conversations about marketing strategies and proven systems, you can build your dream life the way you were meant to—with success, happiness, and pride. 

Start with “The Price of Entrepreneurship No One Talks About (And Why I’d Pay It Again),” it’s the best.

Acquired

Hosted by Ben Gilbert and David Rosenthal, Acquired thrives on the idea that EVERY company has a story. Of course, they want to talk to world-renowned entrepreneurs and trailblazers and learn more about them. But they also want to know their brand’s strategies and designs, which is what we really care about. 

The content isn’t even the only interesting part of the show, though; each episode is just about 4 hours long. Yes, you read that right—FOUR hours! So when we say that they’re leaving no stone unturned, we mean it. You can learn about everything from Coca-Cola to Trader Joe’s—and what made them empires in the business world.

Founder’s Story

Peter Ashton, host of Founder’s Story, isn’t your typical host—and this isn’t your typical podcast. It’s an immersive look into the lives of undiscovered entrepreneurs who have built and led their brands with purpose. Every episode dives deep into the qualities that define true leadership, from decision-making to values-driven growth. 

Peter makes sure to focus on the human side of entrepreneurship, which is so easy to forget about sometimes. Instead of just spotlighting success stories, he’s focusing on the journey, challenges, and behind-the-scenes moments that shape founders. It’s inspiring for any entrepreneur who wants to know how a brand is built—not just why. 

Tune into “She Made $3M in One Week with 7 Words | Aurora Winter, Founder of Same Page Publishing!” It’s a SUPER interesting listen. 

Podcasts about entrepreneurship walk you through how to build a brand—not just dream about it.

Let’s keep it real here, being an entrepreneur can be intimidating. You have to be willing to be inventive, creative, and determined—even when you don’t reach the end result immediately. Anxiety aside, though, it’s SOOO worthwhile. Knowing you’re a badass self-starter who built something from the ground up? Yeah, it’s worth every single second. And it’s TOTALLY do-able with these podcast recs. 

Don’t stop here, though! Head to the Dear Media blog, where we have plenty of advice on (and examples of) business, entrepreneurship, and success. And, of course, don’t forget to check out our incredible group of Dear Media podcast hosts, who are all total testaments to where creativity and drive can get you.