As entrepreneurs, we’re often exposed to the same popular podcasts like How I Built This, The Tim Ferriss Show, or Masters of Scale. While these shows are worthwhile, they have become the standard fare in entrepreneurship circles. The true advantage lies in unearthing podcasts that haven’t hit the mainstream yet—those that venture beyond conventional advice and delve into hard-won insights, innovative strategies, and the raw truths that many entrepreneurs are either too busy or hesitant to address openly.

In my experience as a venture investor and CEO, I’ve observed that successful entrepreneurs are those who challenge conventional thinking, explore less obvious viewpoints, and tap into wisdom from unexpected sources. These podcasts might not pop up in your LinkedIn suggestions, but they’ll expand your mindset and offer insights that your competitors are unlikely to have encountered.

Here are 10 underrated podcasts that deserve a permanent spot in your queue.

1. The Indie Biz Podcast

This particular show spotlights small, independent businesses—those that bootstrap their way up without the help of Silicon Valley funding. Through its episodes, it showcases founders who tackle challenges with creativity rather than relying on venture capital. For entrepreneurs, it serves as a vital reminder that achievement lies not in reaching billion-dollar valuations, but in creating lasting, meaningful businesses.

Takeaway: Learn how scrappiness and creativity often matter more than scale.

2. Bootstrap Stories

Another podcast profiles entrepreneurs who have steadily built their businesses without external funding. It provides an unvarnished look at what it means to prioritize business growth over personal comfort and how these founders resisted the lure of early-stage investment.

Takeaway: Discipline in growth and ownership has its advantages. You control your destiny.

3. Creative Elements

Jay Clouse, the host, offers interviews with creators and solopreneurs who are thriving on their own terms. His show is not just about business logistics; it dives into the mindsets of creativity, discipline, and personal brand development. For those in content, media, or personal branding, this podcast is invaluable.

Takeaway: Entrepreneurs are creators too, and learning from the creative economy can sharpen your edge.

4. The Unmistakable Creative

Breaking the mold of typical business podcasts, this series explores the unusual and the unexpected. It shifts focus away from business tactics, emphasizing broader perspectives by featuring artists, scientists, and thinkers whose unique insights intersect with entrepreneurship in fascinating 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.

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.

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.