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.

What to Look for During the Olympics

Soon, the XXIII Olympic Winter Games will begin in PyeongChang, South Korea. From February 8th through the 25th, we’ll witness athletes come from across the globe to show their skills in 15 different sports. Full of competition and camaraderie, every two years, the Olympics become the culmination of hard work and sport, with eyes from all around the world watching to see which countries’ athletes hoist their home flags and bring home the gold.

But with each event I watch, year after year, I find myself extraordinarily impressed with the personal stories of fearlessness that I see in athletes from all over the world. They come from everywhere, from different backgrounds and stories, overcoming adversity in the hopes to live out their greatest dreams.

Take, for instance, the examples of fearlessness we see every day from Olympians, inside and outside of competition:

Kelly Clark

Veteran snowboarder Kelly Clark has already broken another record before she has even started to compete in PyeongChang. The 34-year-old has hit a milestone of being the first U.S. snowboarder to compete in five Olympic games. But the high of holding the title for the most decorated Olympic snowboarder coincided with the lowest point of her career, crashing at the 2015 X Games in Norway and having to recover from possible career-ending injuries.

It’s not unheard of for athletes to get injured once in a while. But that fall was different from all the others. She had torn her hamstring from the bone and tore the cartilage that kept her femur in her hip joint. That meant going through surgery for repair and then a year of recovery time, a kind of injury difficult for any person, let alone Kelly, the winningest athlete in snowboarding history.

She spent a month in bed with her feet bound together. She had to re-learn how to walk. Months off snow meant that she would have to come back and work harder than ever to make up for all that lost time. But for a determined individual like her—one who refused to let the injury define her career by ending it—the answer was as clear as ever: recover, train and compete not just to win, but to inspire others. As another Olympics loomed, Kelly felt a sense of urgency that helped conquer her fears of being defined by her injury rather than her skill.

By qualifying for the 2018 Olympics, she showed everyone around her what she is made of. Before, Kelly already made big bets and made history, but now in PyeongChang, it’s time to demonstrate how she’s evolved. These games will bring new tests as she goes up against athletes half her age, but Kelly stays motivated by keeping things in perspective and above all else, resolving to boldly keep progressing.

Akwasi Frimpong

The story of Akwasi Frompong begins in Ghana, where he was born. He, and his eight other siblings, were raised by his grandmother. His mother had gone to the Netherlands in order to find a better life for her family. At age eight, he followed her there, but with undocumented immigrant status. That status provided difficulties through the years, as Akwasi found trouble getting into schools as he grew older.

It was the Johan Cruyff Institute that took a chance on the young man. Akwasi was admitted into a program that allowed him to excel in academics and sport all at once. It was there that he began running, earning the name “GoldenSprint” and winning the award for International Student-Athlete of the Year.

But an achilles injury would put his competitive dreams on hold. His immigration status meant that Akwasi wouldn’t be able to find timely medical attention, and, unable to fully recover, the injury would keep him from running for almost three years.

Approached by the Dutch Olympic bobsled coach, Akwasi reached beyond his bubble and decided to take a chance at something brand new. Thirteen years after arriving in the Netherlands, he had become a naturalized citizen and could compete. Believing that the Olympics were a symbol of hope, he joined the team with Sochi 2014 in sight. However, he positioned as second alternate and barely missed the cut.

Unwilling to give up his Olympic aspirations, Akwasi was determined to fail forward, pivoting once again, this time training in skeleton. He founded the first Ghana Bobsled and Skeleton Foundation, and—turning 32 during the games this year—will compete in PyeongChang as the first ever skeleton athlete from Ghana in the Winter Olympics.

By constantly making big bets, Akwasi hopes to make history as the first person to win an Olympic gold medal for the country where he was born.

“What you need for success is already planted deep down inside of you. The root of your success starts in believing in yourself, then it is nurtured with a positive attitude, and then hard work and persistence will bring your success to reality.”
— Akwasi Frimpong

Mikaela Shiffrin

Mikaela Shiffrin has won three straight World Cup titles. The New Yorker called her the best slalom skier in the world. She’s the youngest woman in U.S. history to win a World Championship, and four years ago, she became the youngest person in history to win an Olympic gold in slalom at just 18 years of age.

Her age would tell you that she’s only at the start of her career, but with over 40 World Cup wins under her belt already, anyone can tell that she’s on her way to skyrocketing well beyond that. For context, phenom Lindsey Vonn only had seven career wins at the same age.

But like all of us, Mikaela has her share of challenges. Her achievements don’t come easy, and just weeks before the next Olympic games, she’s coming off of very public falls. As the opening ceremony for PyeongChang quickly approaches, Mikaela is bouncing back from late January failings, where she was unable to finish two World Cup races in a row, falling in one and missing a gate completely in another. For the successful athlete, it was the first time in six years that happened.

But like any fearless actor, Mikaela can make failure matter. With the heavy pressure of the Olympics looming, I’m hoping this bold athlete will fail forward, learning from these mistakes and using them as fuel to propel her Olympic dreams. Mikaela has been favored to win three medals this year, and I hope that she won’t let these recent speedbumps deter her from taking home the gold. And judging by what we see from her in this #BestofUs ad from Comcast NBC Universal, I have a feeling we’ll see big things from her:


These Olympians exemplify the Be Fearless principles the Case Foundation celebrates both in individuals and organizations everywhere. So, as you watch the 2018 Winter Olympic games, think about these athletes, and their fearless stories, as they continue to make big bets and make history, and hopefully provide some inspiration along the way.