Meet Your New Business Advisory Board: The 5 Best Podcasts for Entrepreneurs

As an aspiring founder, you likely have more questions than answers about the perilous journey ahead. Am I overlooking red flags in my business concept? How do I convince investors to take a chance on me? What key hiring mistakes doom startups? And many more.

Fortunately, while the path of entrepreneurship can feel lonely and unclear, you don‘t have to figure everything out through costly trial and error. Not when there are brilliant minds out there who have been in your shoes and lived to tell the tale.

Skip Decades of Hard-Knocks Lessons By Letting Podcasts Guide You

By regularly tapping into the candid conversations happening on some of today‘s best entrepreneurship podcasts, it‘s possible to fast-track your learning. You gain access to an advisory board of proven founders across all industries and company stages willing to share their hardest-earned lessons and secrets to success.

Just some of the invaluable insights you stand to learn include:

  • Validating your business idea – Find out early if your concept actually solves customer pain points or is intriguing enough to attract an initial audience.
  • Avoiding disastrous hiring – Because building a team with the wrong people early on sinks countless startups.
  • Mastering tricky conversations – Like pitching wary investors, retaining frustrated employees, or disputing with co-founders.
  • Strategic decision-making – Understand how top founders determine which features to build first, when to seek funding, if acquisitions are smart, and more.
  • Scaling hurdles – Managing cash flow issues, keeping company culture intact, or balancing rapid growth with minimal hires can make or break you.
  • Founder psychology – Being self-aware, guarding against burnout, powering through imposter syndrome, and building mental resilience saves your sanity.

And much more.

By walking a mile in successful founders‘ shoes vicariously through these podcast episodes, you emerge ready to expect the unexpected, lead with vision and values, and avoid at least some of the speedbumps along the startup highway.

Now let’s explore which entrepreneur podcasts are most worth carving out time for in the rest of your busy calendar:

1. How I Built This (NPR)

If you enjoy losing hours listening to founders of iconic brands tell their origin stories, then NPR’s acidic How I Built This needs to top your playlist. After nearly 500 episodes produced, Guy Raz has proven himself a master at extracting the most interesting threads of his guests’ journeys.

The main draws of How I Built This include:

  • An incredibly diverse set of innovators – everyone from Spanx founder Sara Blakely to Instagram’s Kevin Systrom and beyond.
  • Early startup days retrospectives – with warts-and-all looks at the ugly behind-the-scenes obstacles faced before success.
  • Key character moments highlighted – decisions or realizations that shaped the destiny of now famous companies.
Show DetailsStats
  • 487 episodes and counting
  • Episodes range from 45-90 minutes
  • Clean, professionally produced
  • Hosted by Guy Raz
  • 13M downloads/month
  • 100K ratings on Apple Podcasts
  • 60-minute average episode length
  • 5 years running

🎧 Find on Spotify ➝

🎧 Find on Apple Podcasts ➝


2. The Pitch (Gimlet Media)

When your big idea finally feels solid enough to put in front of investors, few moments are more nerve-wracking. That‘s why Josh Muccio’s aptly named podcast, The Pitch, is such a valuable simulation.

What makes The Pitch stand out is:

  • Authentic pitch simulations – founders lay their business concepts on the line before real VCs and angel investors episode after episode.
  • Critical pitch feedback – blunt, honest criticism on ideas and delivery that guests (and listeners) can learn from.
  • Founder psychology insights – in post-pitch interviews, Josh extracts reflections on what parts founders struggled with.
Show DetailsStats
  • Pitch episodes + “inside” episodes
  • Episodes range 20-30 minutes
  • Hosted by Josh Muccio
  • 140+ episodes to date
  • 2M downloads/month
  • 5 years running
  • 97% rating on Apple
  • 25-minute average length

🎧 Find on Spotify ➝

🎧 Find on Apple Podcasts ➝


3. Indie Hackers

Not every aspiring founder dreams of raising VC millions or building the next unicorn startup. Many would rather craft sustainable small businesses around personal passions with less pressure and risk. If that sounds like you, the Indie Hackers podcast shares valuable guides from those forging such paths.

Why Indie Hackers stands out:

  • Profitable side hustle examples – Founders generating $5K, $50K even $500K per year businesses outside of traditional tech.
  • Transparent look at finances – Guests break down rev numbers, margins, tools that boost profitability and more.
  • The indie lifestyle – What fulfillment looks like when work wraps around passion projects rather than maximum valuations.
Show DetailsStats
  • 300+ episodes
  • Episodes 30-60 min
  • Hosted by Courtland Allen
  • Airs 2x per week
  • 1M downloads/month
  • 1K+ ratings on Apple
  • 45 min average length
  • Launched in 2017

🎧 Find on Spotify ➝

🎧 Find on Apple Podcasts ➝

Listen to Learn…Then Apply What You Learn

While we‘ve only scratched the surface, it‘s clear each of these shows offers immense value to soon-to-be founders like you in different ways. Make it a habit to catch a new episode from whichever podcast resonates most every week. Treat the sage advice and cautionary tales as fuel injecting straight into your entrepreneurial veins.

Just remember—passive listening will only get you so far. Be purposeful about applying what you learn each episode into tangible actions that inch you closer to launching. Treat podcasts as advisory board members guiding your next steps forward, not merely nice-to-haves talking in your ears.

Beyond applying lessons, it‘s wise to track key takeaways that feel particularly relevant to the stage you‘re at. Doing so gives you an easy reference to remind you of growth opportunities and pitfalls to avoid when big decisions arise down the road.

Armed with practical lessons learned from those succeeding before you, you‘ll bypass many needless mistakes and years of painful trial-and-error…even if sceptics try convincing you that will never work.

So which show will you start tuning into first — and what‘s one lesson you hope to apply to your startup right away?

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