7 Fearless Founder Podcasts to Listen To

Everyone loves a good success story, and entrepreneurs tend to have especially fascinating ones. The road to success rarely goes in a straight line; rather, most successful people have encountered quite a few failures and obstacles along the way.  

Learning from these challenges and failing forward is what often leads to breakthroughs. As our Be Fearless principles state, making big bets, failing forward, trying brave experiments, working with unlikely partners and letting urgency conquer fear can be the keys to success for entrepreneurs.

Being fearless isn’t always easy. But seeing stories of fearless entrepreneurs who have braved the path before can be the inspiration capital needed for aspiring entrepreneurs to begin to build their businesses. That’s why telling the stories of entrepreneurs from all backgrounds, and lifting up role models whose stories are not told as frequently in mainstream entrepreneurship coverage, is so important. Our #FacesofFounders campaign has brought together stories of entrepreneurs across race, place and gender, what they struggle with, what they’re building and why inclusivity makes entrepreneurship even stronger. We also regularly share stories of those changing the narrative of who is and can be entrepreneurs in our weekly newsletter, Breaking Good.

But sometimes hearing—not just reading—stories can be uniquely powerful. So, we asked the Case Foundation team to share some of their favorite stories of entrepreneurship, as told by podcasts. While there are many great stories out there, we compiled a list of nine podcast episodes of entrepreneurs who each stand out in a different way. Read on to learn about some of the founders who inspire us and remind us to Be Fearless.


Spanx—Sara Blakely on NPR’s “How I Built This”

Sara Blakely’s story starts with selling fax machines and ends with her becoming the youngest self-made female billionaire in the US. But her journey to get there may be less well-known. She launched Spanx with the money in her savings after seeing a need for an undergarment that incorporates the control top feature of pantyhose without the legs of pantyhose.

Blakely’s journey gathering support from manufacturers, patent attorneys, buyers and even Oprah is an inspiring one for women founders pitching unique and disruptive products. The story of how she convinced a Neiman Marcus buyer to work with her is also a funny reminder that unconventional methods can sometimes be the most effective ones.  

Be Visible—Andrea Guendelman, on Backstage Capital’s “Mission and Values”

As fans of Inclusive Entrepreneurship, we loved hearing about the journey of Andrea Guendelman, who co-founded Be Visible. Recognizing a lack of available professional mentoring and networking resources for Latinx professionals, she built Be Visible as a professional social network for the group.

Throughout the podcast, Andrea breaks down the underlying barriers that separate Latinx professionals from many opportunities available to the wider population. She talks about the group’s unique needs and how Latinx Millennials specifically can be supported and encouraged to be engaged and connected citizens. She also has an interesting backstory that crosses countries and industries before launching Be Visible. Listen through the end to hear about where the platform is going and which big client Be Visible just landed.


Hamdi Ulukaya—Chobani, on Fast Company’s “Innovators Uncensored”

For a lesson in humble beginnings, hard work and compassionate leadership, listen to Fast Company editor, Robert Safian’s interview with Hamdi Ulukaya, Founder and CEO of Chobani. Ulukaya’s path to success was untraditional, to say the least. He started in a closed down factory in a small town in upstate New York, working with a team of just five people and had no prior formal business, marketing or managing experience.

What was the first thing his team did after opening the factory? It’s not what you’d expect, but Ulukaya’s story bucks tradition from the beginning and you have to tune into to hear it straight from Ulukaya. After Chobani’s massive success, Ulukaya shares how he didn’t let success go to his head, how he has sought to stay accountable to his employees and how he doesn’t shy away from wider issues, like the refugee crisis. Listen to the interview to hear him tell the story of two refugees (of the 600 he’s hired) who found success working for Chobani. Ulukaya’s story is the story of a leader rebelling against assumptions about how businesses are run and putting purpose at the center of his business.  

Capway—Sheena Allen, on “VC Cheat Sheet”

Sheena Allen took a non-traditional route to entrepreneurship, launching Capway, a Financial Tech company, from rural Mississippi. Allen talks about her journey to launching the FinTech company, which serves different groups of financially underserved consumers and talks about the unconscious bias that she had to overcome to succeed.  

The ‘aha’ moment that led to her launching Capway came in a grocery store, where she saw a long line of people waiting to cash their checks. Through more research, Allen identified the massive gap in financial services for unbanked and underbanked populations—which leads to people cashing checks at nontraditional financial institutions, like grocery and convenience stores. Despite there being a huge market to serve this community, gaining support from investors was a challenge. Allen shares how she’s been able to find success and find the right investors to work with. And she holds nothing back, giving very direct advice to women and other underrepresented entrepreneurs looking to build support and sharing her advice on how to ask for help the right way. Listen to her story for insight into the experience of an entrepreneur building support for a service for underrepresented consumers.


Radio One—Cathy Hughes, on NPR’s “How I Built This”

For some serious entrepreneurial inspiration, you’ll want to listen to Cathy Hughes’ journey to radio success, which involves a fair share of bumps in the road along the way. As a young, single mom, Hughes moved from Omaha, Nebraska to Washington, DC to help launch the radio station at Howard University. She found success there by creating shows that catered to underrepresented communities in DC, but her journey didn’t stop there.

Hughes’s path to becoming a media mogul takes unexpected twists and turns, including a stint of living with her son in the young, struggling radio station she bought. Her story of navigating entrepreneurship, motherhood, success and expansion as a female founder of color is interesting for so many reasons; from the creative to the financial to the personal.

Coss Marte—ConBody, on Gimlet Media’s “Start Up”

Part 1 and Part 2
This is a story about second chances. Coss Marte is an ex-convict who spent four years in prison for selling drugs. Fast forward to today and he’s running a successful fitness business, ConBody.  

The inspiration for the company came while Marte was still in prison. Dealing with health problems and the confinement of prison, Marte developed his own workout routines that could be done in small spaces and without weights, and he helped other inmates do the same. In the podcast, Marte shares his story building up a customer base, battling negative perceptions and making sure to hire fellow ex-convicts, who struggle to get jobs after leaving incarceration. The podcast begins and ends with Marte and his cofounder, Jenn Shaw going to a pitch competition where they’re starkly reminded how much they stand out; he being Latino and Shaw being a woman among a crowd of mostly white, Ivy league grads. The story of his journey there, and the results of the pitch competition, will inspire and surprise you.


Mariam Naficy—Minted, on “Masters of Scale with Reid Hoffman”

Mariam Naficy is a two-time founder who launched both her companies in uncertain times. She started with Eve.com, the first major online cosmetics seller, which she launched in the late 90’s, a time when the future of the internet was unclear. In fact, to obtain the domain name, she actually had to make a deal with a very powerful five-year-old by the same name. From there, Eve.com raised $26 million in its first year and continued to scale rapidly until she sold the company in 2000.

After moving on from Eve, Naficy moved on to her next venture, Minted, an online stationary store. In this episode, she shares her challenges raising venture capital as a mom entrepreneur, and launching a company in 2008, at the height of a financial crisis. Minted would go on to raise $89 million in Venture Capital and ship to 70 million households, but along the way, Naficy faced a lot of teachable failures, which she shares with listeners.

We hope these podcasts inspire you as much as they have our team. For some more #BeFearless inspiration, check out our Be Fearless hub, and to learn more about how we’re championing entrepreneurship for all through inspiration capital and more, check out our Inclusive Entrepreneurship page and #FacesofFounders series.