10 Underrated Podcasts Every Entrepreneur Should Be Listening To These 10 podcasts cut through the noise with unfiltered lessons, unconventional strategies and stories that actually prepare you for the entrepreneurial grind.
By Roy Dekel Edited by Chelsea Brown
Key Takeaways
- Forget the same recycled recommendations. The smartest entrepreneurs gain an edge by tuning into voices that fly under the radar.
- These 10 podcasts are raw, unpolished and packed with insights you won't find in the mainstream.
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As entrepreneurs, we're constantly bombarded with recommendations for the same big-name podcasts (How I Built This, The Tim Ferriss Show or Masters of Scale). They're good, but they've become the mainstream playlists of the entrepreneurial world. The real edge comes from discovering voices that are flying under the radar — podcasts that don't just regurgitate clichés but dig into gritty lessons, unconventional strategies and the realities most entrepreneurs are too busy or too cautious to discuss openly.
As a venture investor and CEO, I've seen firsthand that the entrepreneurs who win are the ones who think differently, seek perspectives outside the obvious, and leverage wisdom from unexpected places. These podcasts won't necessarily appear in your LinkedIn feed, but they'll challenge your thinking and, more importantly, give you the kind of insights your competition probably hasn't heard yet.
Here are 10 underrated podcasts that deserve a permanent spot in your queue.
Related: The 10 Best Podcasts Every Entrepreneur Should Listen to for Growth, Strategy and Success
1. The Indie Biz Podcast
This show focuses on small, independent businesses — the kind that bootstrap from scratch without Silicon Valley backing. The episodes highlight founders who navigate obstacles with resourcefulness rather than venture capital. For entrepreneurs, it's a refreshing reminder that success isn't about billion-dollar valuations but about building sustainable, real businesses.
Takeaway: Learn how scrappiness and creativity often matter more than scale.
2. Bootstrap Stories
This podcast dives into entrepreneurs who took the long road — growing without outside investment. It's raw, honest and humbling. Founders share what it's like to sacrifice personal comfort for business growth and how they resisted the temptation to chase capital too early.
Takeaway: Discipline in growth and ownership has its advantages. You control your destiny.
3. Creative Elements
Host Jay Clouse interviews creators and solopreneurs making a living on their own terms. It's not just about business mechanics; it's about the psychology of creativity, discipline and building personal brands. If your work involves content, media or personal branding, this podcast is pure gold.
Takeaway: Entrepreneurs are creators too, and learning from the creative economy can sharpen your edge.
4. The Unmistakable Creative
Unlike formulaic business shows, this podcast dives deep into the unusual and unexpected. It's less about business tactics and more about perspective — bringing in artists, scientists, and thinkers whose insights cross-pollinate with entrepreneurship in surprising ways.
Takeaway: Great business breakthroughs often come from outside the business world.
5. StartUp Therapy
Two founders (Wil Schroter and Ryan Rutan) talk candidly about the mental and emotional battles entrepreneurs face. From burnout to imposter syndrome to co-founder conflicts, it's a brutally honest discussion that feels more like a therapy session than a business seminar.
Takeaway: Entrepreneurship isn't just about strategy; it's about managing your mind and emotions.
Related: 25 Top Podcasts That Will Spark Your Entrepreneurial Vision
6. The Sweaty Startup
Nick Huber focuses on "uncool" businesses — self-storage, property management, cleaning services — that generate massive wealth. It's a counterbalance to the obsession with tech startups, reminding us that riches are often made in industries no one brags about at cocktail parties.
Takeaway: Don't overlook "boring" businesses — they're often the most profitable.
7. The Exit
This show spotlights founders who've sold their companies, breaking down the process of negotiations, valuation and exit strategy. It's tactical and strategic, and it teaches entrepreneurs to think with the end in mind, even when they're just starting.
Takeaway: Building with an exit in mind shapes smarter decisions from day one.
8. Business Wars
More of a storytelling show than a tactical one, Business Wars dramatizes rivalries between iconic companies — Nike vs. Adidas, Netflix vs. Blockbuster, Uber vs. Lyft. For entrepreneurs, these stories reveal how strategy, timing and ego shape industries.
Takeaway: Learn from history. Understanding how giants fought their wars can prepare you for your own battles.
9. The Twenty Minute VC
Harry Stebbings interviews top investors and founders, but it's not a polished PR tour. The conversations are direct and filled with behind-the-scenes insights about what investors actually look for and what separates good pitches from bad ones.
Takeaway: If raising money is on your roadmap, this show gives you a rare peek inside the investor's head.
10. My First Million
While not completely "underrated," it still flies under the mainstream radar compared to the giants. The hosts brainstorm business ideas, dissect companies and share unconventional strategies for building wealth. It's fast, funny and refreshingly irreverent.
Takeaway: Business ideation is a skill — you get sharper at spotting opportunities by listening to others riff.
Related: 30 Top Podcasts for Influential Entrepreneurs
Why these podcasts matter
What sets these podcasts apart isn't just that they're less well-known; it's that they expose you to perspectives and strategies outside the typical entrepreneur echo chamber. Mainstream shows often polish their stories for mass appeal, but these conversations are raw, unfiltered and unapologetically real.
They remind us that entrepreneurship isn't a highlight reel — it's the grind, the doubt, the breakthroughs and the failures that lead to transformation.
If you're serious about growth, carve out time to listen. Put one of these podcasts into your rotation each week. Don't just listen passively. Take notes, share with your team, and apply the insights to your business.
Because in a world where everyone is consuming the same mainstream content, the real advantage comes from tuning into voices your competitors aren't even aware of yet.
