“Mistakes are the portals of discovery.” — James Joyce

If you’re an aspiring founder, no matter what phase you’re in, chances are you’re experiencing a lot of growing pains. Entrepreneurship is hard, and you might be sick of everyone telling you that failure makes you stronger.

And the startup world is brutal, creating a business is not for the faint of heart. So it’s natural to seek out wisdom from those who came before you. Whether you’re looking for startup success stories to inspire you, or startup fails to help you make sense of your own challenges — intimate podcast interviews with founders are an incredible resource. 

Since you may not know where to start, we’ve made a list of some of the best founder stories out there. Here are our favorites and why you should listen to them.

Why You Should Listen to Another Startup Story

What if you could minimize your failures by learning from others who have already done it? 

What if you could find comfort, hearing how pioneering entrepreneurs made it through their toughest times? 

There are a million reasons to listen to startup founder stories, here are just a few.

Learn Valuable Lessons and Gain New Perspective

Candid conversations are a goldmine of valuable information, so we should all be thanking the bear-all standard in podcasting.

You should always keep in mind that there’s some element of marketing involved in these conversations (the founder is likely trying to promote their business). But even so, they’re certainly going to be candid — because podcast listeners expect authenticity.

Create Active Time When You Listen to Startup Podcasts

If you’re working on launching your own startup, you probably don’t have a lot of time.

But when you listen to startup stories on podcasts, you’re turning passive time into value, active time. You can give yourself an edge and acquire new knowledge while you’re waiting in line for your lunch, walking to work, or getting a pedicure.

Get Inspired by Founder Energy

The truth is that sometimes entrepreneurship can be a major bummer. So there might also be days when you’re not looking to learn another success equation.

When you’re down in the dumps, you don’t want to hear about everyone else’s happy endings — you want startup failure stories. Or depending on your personality, you may need to feed off the positive energy of a successful startup founder. Either way, there’s a podcast for that.

10 Podcast Episodes That Tell Great Startup Stories

Here are the top podcast episodes featuring startup stories that you won’t want to miss.

The Empathy Flywheel with Sarah Friar

(Episode #74 of Masters of Scale)

Guest, Sarah Friar is an inspiring leader in the startup world. She’s the CEO of Nextdoor, former CFO of Square,and recent co-founder of Ladies Who Launch.

In this episode she talks with host Reid Hoffman (co-founder of LinkedIn), about customer experience, empathy, and scaling a business. You’re sure to be left in awe of Friar’s success in Silicon Valley. 

Nonetheless, you’ll probably be more impressed by her courage, grit, and work ethic. She grew up in Northern Ireland during one of it’s most dangerous eras, studied metals at Oxford, and even spent time working in a mine. Friar is a founder we can learn from.

The Philosopher CEO with Justin Kan 

(Episode #1 of Below The Line Podcast)

This podcast is hosted by James Beshara, who likes to get what he calls, the “below the line” version of his guests’ stories — the real version of the person behind the success story.

And Beshar does just that, in an interview with one of the most prosperous young founders in Silicon Valley, Justin Kan. He co-founded impressive companies like Twitch, SocialCam, and Atrium. 

In this conversation, Kan talks about growth, leadership, and his favorite things about being a founder. But you might find yourself more interested in his reflections about his near death experience and his personal pursuit of happiness.

And the best part — this is only the first of many incredible conversations you can hear on this popular startup podcast.

The Family and Friends Gap

(Episode #99 of The Pitch from Gimlet)

Entrepreneurs Farah Allen (CEO and co-founder of The Labz), and Demetrius Gray (founder of Weather Check), talk with The Pitch about “the family and friends gap.”

They dive into how this is “the real seed funding,” and how it’s crucial for startups in the early stages. So it can be a huge obstacle for aspiring founders who don’t have family or friends with access to generational wealth.

Founders who do, can usually expect between 50k – 100k in funds. But what happens if you get nothing in this round? Unfortunately, lots of these founders are haunted by the friends and family round, and get trapped in a negative feedback loop. The VC system is broken, and it’s not a meritocracy.

Both of these entrepreneurs had to get creative. Through accelerators, competitions, and some big sacrifices, they ultimately created successful, million dollar companies. If you are like so many who don’t have access to generational wealth, you need to hear this.

Seth Godin on the Future of Marketing

(From 7-Figure Small with Brian Clark)

Seth Godin is the best-selling author of 19 books. He’s also a former Yahoo executive and he coined the term “permission marketing.”

In this episode Godin discusses the importance of consistency, human connection, the pitfalls of automation, and so much more. He’s one of the most respected voices in marketing out there, so if your startup creates content, you’re sure to be drooling over his every word.

He also has his own podcast — Akimbo —  about culture and “how we can change it.”

Apple MacBook beside computer mouse on table

Stellar Growth, Platform Risk, Layoffs and Powering Through Roadblocks

(Episode #451 of Startups For the Rest of Us)

In this show, host Rob Walling interviews Laura Roeder, the founder and CEO of the SaaS app, MeetEdgar

Roeder and Walling get into the details of her rapid success at the beginning of her career. They talk about how she made an unprecedented 7-figures in less than a year. But the juicy stuff comes later.

When she opens up about the challenges that followed her extraordinary business triumphs. How she was faced with some unexpected and humbling obstacles. And these roadblocks were followed by even more struggles as she pursued another SaaS venture.

With two raw startup stories in just one episode, you’re sure to be inspired by this formidable founder.

Quibi’s Shortform Life

(Episode #273 of Equity)

Okay so this isn’t your typical founder interview — but it’s by one of the best podcasts for tech entrepreneurs. Equity is a venture capitalist focused podcast show by TechCrunch, and it’s a great news resource if you’re interested in the startup world.

In this episode, they recount the mega fail that was the media startup, Quibi. It was considered one of the “biggest startup deaths” in recent media history. It amassed a huge amount of capital ($1.7 billion), but collapsed almost immediately after launch.

This is the least personal of the episodes on our list, but it is thoughtfully analyzed by three brilliant hosts  — Alex Wilhelm, Natasha Mascarenhas, and Danny Crichton. These three deem the demise of Quibi as one of the most noteworthy startup failure stories of our time.

Why The Best Way to Learn is by Doing with Kai Bond

(Episode #61 of Startup HandMeDowns)

This conversation features accomplished entrepreneur turned investor, Kai Bond. One of his startups was purchased by Samsung and he was a manager for the incubator that developed Tinder.

Now, he’s the lead investor at Catalyst Fund, which aims to support the entrepreneurial efforts of underrepresented groups. You’re sure to be impressed by this guest but not only because of his wild success.

True to the form, Bond gets real in this interview. He reflects on his lowest moments, and shows vulnerability when he remembers being too poor to afford a subway ticket.

Up in Flames

(Season #3, Episode #9 of StartUp from Gimlet)

You won’t want to miss this thrilling story from one of the top startup podcasts out there. In this episode, NPR correspondent Dan Charles chronicles the life and businesses of Edgar Diaz.

The story follows a passionate dairy scientist and yogurt maker from Colombia to Dallas — where he co-founded Three Happy Cows. With this company, he gained national acclaim and thousands of loyal customers. But what stands out about Edgar is his passion for the craft. He talks fondly of yogurt throughout the interview.

While some might view this as a cautionary tale (the title says it all), food entrepreneurs are sure to be inspired by this founder’s passion. And even though things don’t end well — Diaz’ wife leaves listeners with a profound message.

“Do it again, but do it right.”

What 17 yrs of blogging taught her

(Episode #1982 from Mixergy Podcast)

This long-running startup podcast has over 2,000 episodes to choose from. Host, Andrew Warner has interviewed a laundry list of giants in the industry — including entrepreneurs from YCombinator and Wikipedia.

This conversation features the founder and CEO of Small Business Trends — Anita Campbell. She decided to become an entrepreneur after a car accident brought her new perspective. 

We chose this interview because Campbell is an impressive founder, who has demonstrated perseverance and passion over the years. But she also reminds us of something important that lots of people tend to forget — that your business doesn’t need to be huge to be successful. 

Comparing Yourself with Other Founders & Startups

(Episode #432 from The Startup Chat with Steli & Hiten)

We saved this one for last on purpose. Because listening to the stories of other founders is a great way to learn and get inspired — but only when you’re getting a full picture and a real person.

In this episode, co-hosts Steli and Hiten remind us why comparing yourself  to others is a dangerous road you shouldn’t go down. The journey is what’s important — and it’s going to look different for everyone. 

While social media makes it especially easy to compare and get down on yourself, it’s not going to help you or your startup. The takeaway — “stop!” 

The Best Podcasts About Startups Provide Valuable Insight

So remember, no two founder stories are alike. But you should take advantage of these candid, tell-all podcast episodes about startup triumphs and fails. 

These startup stories will inspire you, provide you with valuable lessons, and keep you company while you eat breakfast.


So comment below and let us know. Did we miss your favorite startup stories podcast? What startup podcasts do you listen to when you need some founder inspiration? And most importantly — which founder has taught you the most?

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