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The 5 Best Podcasts Every Digital Entrepreneur Must Listen To

As a digital technology expert and passionate entrepreneur, I know firsthand the value of continuous learning and seeking out wisdom from those who have paved the way. In today‘s rapidly evolving digital landscape, one of the best ways to stay sharp and inspired is by tuning into podcasts hosted by successful founders and innovators.

But with over 2 million podcasts available and thousands targeting entrepreneurs, it can be overwhelming to know where to start. That‘s why I‘ve curated this list of the 5 best podcasts that every digital entrepreneur must add to their playlist.

Whether you‘re a software developer with a SaaS idea, an e-commerce founder looking to scale, or a content creator building a personal brand, these podcasts offer invaluable insights and inspiration to help you navigate your entrepreneurial journey. Each one brings a unique perspective and area of focus, from high-level mindset shifts to nitty-gritty growth tactics.

I‘ve carefully selected these podcasts based on the depth and actionability of the content, the diversity of voices and business models represented, and the engaging storytelling and production quality. I‘ve also prioritized podcasts that cater to digital entrepreneurs at various stages, from aspiring founders to seasoned operators.

1. Masters of Scale with Reid Hoffman

Masters of Scale Podcast Cover Art

Hosted by Reid Hoffman, co-founder of LinkedIn and partner at Greylock, Masters of Scale is a must-listen for any founder with ambitions of building a world-changing tech company. In each episode, Hoffman illuminates a key principle or strategy for scaling a business through a blend of engaging storytelling, expert interviews, and actionable insights.

What sets Masters of Scale apart is Hoffman‘s unparalleled access to the biggest names in tech and beyond. You‘ll hear in-depth conversations with visionaries like Mark Zuckerberg, Reed Hastings, Marissa Mayer, and Brian Chesky, as well as unexpected guests like General Stanley McChrystal and Ariana Huffington.

But this isn‘t just a show about big names and unicorn valuations. Hoffman and his guests dive deep into the human challenges and practical realities of scaling a business, from establishing culture to hiring to pivoting in the face of failure. You‘ll come away with frameworks and mindset shifts that are relevant whether you‘re a bootstrapped SaaS founder or an aspiring tech mogul.

Some of my favorite episodes include:

  • "Rapid Response: How to Master Disaster" with Airbnb‘s Brian Chesky
  • "Why Customer Love is All You Need" with Y Combinator‘s Sam Altman
  • "How to Build a Team That Ships" with Facebook‘s Sheryl Sandberg

Whether you‘re scaling your startup or just dreaming of your first hire, Masters of Scale offers a rare window into how the most iconic founders approach the journey of company-building. It‘s a beautifully produced, binge-worthy show that feels more like an HBO drama than a business podcast.

2. Indie Hackers

Indie Hackers Podcast Cover Art

Indie Hackers is the go-to podcast for the solopreneur, the bootstrapper, the maker who wants to build a sustainable tech business on their own terms. Hosted by Courtland Allen, Indie Hackers showcases the stories of founders who have succeeded without following the typical Silicon Valley playbook.

What I love about Indie Hackers is the sheer variety of niches, business models, and approaches represented. In one episode, you might hear from a developer who reached $10k in MRR for a hyper-specific software tool. In another, you‘ll learn how a marketer built a thriving e-commerce brand off the back of TikTok.

Some standout episodes include:

  • "Growing ConvertKit to $2 Million in MRR" with Nathan Barry
  • "$1M+ in Sales in One Year as a Solo Founder" with Sabba Keynejad of VEED
  • "Building a $30k/Month Business Around Obsidian" with Liam Cain

Through in-depth interviews, Allen extracts actionable insights and hard-won lessons from these indie hackers. But what really sets the show apart is the focus on the mental and emotional side of bootstrapping. Allen creates a safe space for guests to share their struggles with impostor syndrome, burnout, and isolation, and to celebrate the freedom and fulfillment that comes with building something of your own.

With over 500 episodes available, Indie Hackers is an inexhaustible resource of inspiration and tactical advice for the digital entrepreneur who wants to make a living doing something they love. And the episode format, which ranges from 60 to 90 minutes, allows for the perfect blend of storytelling and practical how-to.

3. Mixergy

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Mixergy is a powerhouse of entrepreneurial wisdom, with over 1,500 interviews recorded since its founding in 2008. Hosted by Andrew Warner, who sold his own $30 million per year business, Mixergy is known for its in-depth, no-holds-barred conversations with founders across industries and company sizes.

One of the defining features of Mixergy is Warner‘s singular interviewing style. He‘s direct, persistent, and unafraid to push guests to unpack their success (and failures) in granular detail. This can lead to some tense moments, but it also makes for refreshingly substantive conversations that go beyond the surface-level insights found in many business podcasts.

Some of the most impactful Mixergy episodes for digital entrepreneurs include:

  • "#1931 Case Study: Building a $3M ARR SaaS Using Reddit" with Lenny Rachitsky of Lenny‘s Newsletter
  • "#1902 How a Burned Out Developer Built a $228M SaaS" with Amir Salihefendic of Doist
  • "#1820 How to Make Your First Dollar Online" with Noah Kagan of AppSumo

But Mixergy isn‘t just a treasure trove of tactical advice. Warner also has a knack for surfacing the human stories and psychological insights behind his guests‘ entrepreneurial journeys. You‘ll hear vulnerable conversations about crippling self-doubt, disastrous launches, and personal sacrifices made in the pursuit of business success.

With its extensive archives and diverse range of guests, Mixergy has something to offer digital entrepreneurs at any stage and in any industry. And for those looking to dive even deeper, the Mixergy Premium membership unlocks hundreds of exclusive interviews, case studies, and courses.

4. The Pitch

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If you‘ve ever dreamed of pitching your startup to a room full of investors, The Pitch is the next best thing. Hosted by Josh Muccio, The Pitch is like a podcast version of Shark Tank, featuring real entrepreneurs pitching their businesses to a panel of angel investors and VCs.

But The Pitch is more than just entertainment. Each episode is a mini masterclass in the art of the pitch, as Muccio and the investors dissect what works and what doesn‘t in the founders‘ presentations. You‘ll learn how to craft a compelling narrative, anticipate tough questions, and think on your feet when the pressure is on.

The businesses featured on The Pitch span a wide range of industries and models, from a gamified language learning app to a DTC plant-based feminine care brand. And while not every pitch ends in an investment, each one offers valuable lessons for entrepreneurs looking to refine their own messaging and fundraising strategies.

Some of the most educational episodes of The Pitch include:

  • "Copper Cow Coffee: Debbie Wei Mullin"
  • "Paladin: Kristen Sonday"
  • "Goody: Jasmine Shells"

In addition to the pitch itself, each episode of the show features a debrief segment where Muccio and the investors unpack the strengths and weaknesses of the pitch and offer candid feedback and advice to the founder. It‘s a rare window into the minds of investors and a priceless resource for any entrepreneur looking to raise capital.

With its unique format and diverse range of startups featured, The Pitch is a must-listen for any digital founder who wants to hone their storytelling skills and understand what investors are really looking for. And at just 30-40 minutes per episode, it‘s an easy and engaging way to level up your pitching game.

5. How I Built This with Guy Raz

How I Built This Podcast Cover Art

Last but certainly not least is How I Built This, the blockbuster NPR podcast hosted by Guy Raz. With over 300 episodes in its catalog, How I Built This is a treasure trove of entrepreneurial wisdom and inspiration, featuring in-depth interviews with the founders behind some of the world‘s most iconic brands.

What sets How I Built This apart is Raz‘s masterful storytelling and interviewing skills. He has a knack for drawing out the most compelling and relatable moments in his guests‘ entrepreneurial journeys, from the initial spark of inspiration to the pivotal make-or-break decisions. You‘ll hear the stories behind the founding of companies like Airbnb, Slack, Patagonia, and Bumble, straight from the founders themselves.

But How I Built This isn‘t just a highlight reel of entrepreneurial success. Raz also delves into the low points and failures that every founder faces, and the resilience and grit required to persevere through them. You‘ll hear candid conversations about the sacrifices and trade-offs inherent in building something from nothing, and come away with a deeper appreciation for the human beings behind the business titans.

Some of my favorite episodes of How I Built This for digital entrepreneurs include:

  • "Slack: Stewart Butterfield"
  • "Mailchimp: Ben Chestnut"
  • "Shopify: Tobias Lütke"

While How I Built This primarily features later-stage companies, the insights and lessons shared are relevant to founders at any stage. Whether you‘re just starting out or scaling your business, you‘ll find endless inspiration and practical wisdom in these founder stories.

One of the things I love most about How I Built This is the diversity of industries and business models represented. From e-commerce to SaaS to media and beyond, Raz showcases the many different paths to entrepreneurial success and the common threads that unite them all.

If you‘re looking for a podcast that will leave you feeling inspired, energized, and ready to tackle your own entrepreneurial dreams, How I Built This is a must-listen. With its unparalleled access to the most accomplished founders of our time and Raz‘s singular ability to draw out their most powerful stories and lessons, this show is a masterclass in what it takes to build something extraordinary.


As a digital entrepreneur, the journey can often feel isolating and overwhelming. But by tapping into the wisdom and experience of those who have gone before us, we can find the inspiration, guidance, and practical tools we need to persevere and succeed.

These five podcasts offer an incredible wealth of knowledge and insight for entrepreneurs at any stage of the journey. Whether you‘re looking for high-level frameworks for scaling a tech startup, tactical advice for bootstrapping an online business, or powerful stories of resilience and ingenuity, you‘ll find it in these shows.

But the value of these podcasts goes beyond just the information they provide. By listening to the stories and struggles of other entrepreneurs, we can find the motivation and perspective we need to keep going when the going gets tough. We can see that even the most successful founders face doubts, setbacks, and failures, and that the key to success lies in the ability to learn from them and keep moving forward.

So whether you‘re a seasoned entrepreneur or just starting out on your digital business journey, I encourage you to make these podcasts a regular part of your learning and growth routine. Subscribe to the shows that resonate with you, and make a habit of listening to at least one episode per week. Take notes on the insights and action items that stand out to you, and start implementing them in your own business.

And remember, entrepreneurship is a marathon, not a sprint. By consistently investing in your own education and mindset, and by learning from the successes and failures of others, you‘ll be well on your way to building something remarkable of your own.

Happy listening, and here‘s to your entrepreneurial success!