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.

This Month in Social Good

February may be the shortest month of the year, but this February was packed with news in the world of social innovation. In particular, we saw new data, stories and perspectives brought forward in the world of Inclusive Entrepreneurship that we’d like to reflect on and use to power the movement. I spent some time rereading our weekly Case Foundation Breaking Good newsletter to gauge some of the conversation around supporting diverse entrepreneurs this month. Here are some of the articles and trends that stood out to me: 

Black History Month is a reminder to uplift Black entrepreneurs—past and present

Every day is a great day to celebrate the achievements of groundbreaking innovators in history and the people who are carrying on their legacies and building their own. But as Black History Month comes to a close, we’re given a renewed commitment to uplift the stories of Black entrepreneurs—sharing both the contributions they bring and the unique challenges they face. 

With that in mind, we were inspired by reflections from successful Black entrepreneurs on how they succeeded in a world filled with barriers designed to stifle their progress. One of the Be Fearless quotes that stood out came from Urban One founder, Cathy Hughes: 

“[Don’t] let anyone convince you that your dream, your vision to be an entrepreneur, is something that you shouldn’t do. What often happens is that people who are well meaning, who really care for us, are afraid for us and talk us out of it.” 

There’s a glaring gap for women entrepreneurs

As reports highlighting data on entrepreneurship from 2017 begin to come out, the statistics on women entrepreneurs are disheartening, to say the least. According to Pitchbook, businesses with all-women founding teams received just 2.2 percent of all venture capital in 2017. Teams with a mix of genders received just 12 percent, and a whopping 79 percent of venture capital went to all-male teams (the remaining 7 percent was unreported). 

To change these numbers, there isn’t an easy fix. We know where we can start—more women launching businesses, more women in venture capital, fewer cases of bias at the hands of investors—but none of these alone will solve the problem. Partners are stepping up across industries to build solutions together that will collectively challenge the systemic biases that affect how opportunity is distributed in our culture. Data and storytelling can play major role in that, which brings us to our next trend. 

We need to support data and storytelling on underrepresented innovators

Sherrell Dorsey is doing just that. Dorsey founded a daily newsletter called ThePLUG to report on founders, investors and innovators of color. This month, she talked to Vice about the need for more data on Black entrepreneurs. This is one of the many great points she made: 

“A lot of times, especially in the black community, when you look at entrepreneurship, there’s been very little data collection—like, the kind of businesses we’re creating, the kind of problems that we’re solving. (…) A lot of times investors are looking for patterns in data, so when that information is not shared in public, you get a knowledge gap.” 

To extrapolate out from what Sherrell is saying, if investors don’t have the data they are used to having when making investment decisions, they are less likely to fund initiatives. Therefore, having a more robust dataset on Black entrepreneurship could help spark solutions across the board. That’s something we’re working towards as we champion inspiration capital as a core part of our Inclusive Entrepreneurship work. By uplifting the stories of underrepresented entrepreneurs—stories that share both their challenges and their unique insights—we’re hoping to change widespread assumptions about who is and can be a talented entrepreneur. 

Entrepreneurship can flourish across in all communities across the U.S.

Another widespread assumption about entrepreneurship we’re working to challenge is the notion that Silicon Valley is the only great place to launch a company. Fortunately, that idea is being challenged by entrepreneurs, investors and ecosystem builders across the country. We loved hearing about how Kela Ivonye, founder of connected delivery storage service, MailHaven found Louisville Kentucky, not Silicon Valley to be the best place to build the company.  

On the ecosystem side, we’ve been inspired by news about places like Raleigh, where a program is helping formerly incarcerated individuals pursue entrepreneurship. In the Midwest, a variety of organizations are working to support the region’s female entrepreneurs. And in New York, three of the city’s major banks announced plans to give a combined $40 million to programs supporting women and entrepreneurs of color there.  

This month, Engine also interviewed an ecosystem builder in Colorado as part of an ongoing series we love, #StartupsEverywhere, where the outlet talks to the people building entrepreneurial ecosystems across the country. And this week’s Kauffman Foundation newsletter poses important questions on how we can build inclusive ecosystems, including a powerful video by Melissa Bradley on her experiences as an entrepreneur, investor and ecosystem builder. 

From celebrating past and present Black entrepreneurs and leaders, to building solutions for female founders, to tackling the data gap, to highlighting innovation everywhere—leaders in the world of Inclusive Entrepreneurship are getting to work. The stories we’ve seen this month inspire us and we can’t wait to read and share even more of these informative and inspirational stories. To learn more, sign up for our newsletter, Breaking Good. 

Is there anything we missed this month? Tell us about your favorite social good story you saw in February! 

A Month of Entrepreneurial Stories

Our Inclusive Entrepreneurship work at the Case Foundation is built upon the core value that we must change the way we all talk about entrepreneurship, expanding who we lift up as success stories and busting myths that hold entrepreneurs back. National Entrepreneurship Month gave us a great opportunity to dive into the subject again and to celebrate entrepreneurs from a wide variety of backgrounds. It also gave us a chance to provide an honest look at some of the challenges of entrepreneurship.

We focus our work in Inclusive Entrepreneurship on challenges across race, place and gender, driven by the stark statistics that show the disparities faced by diverse entrepreneurs. Just looking at venture capital distribution reveals that only 10 percent of venture-backed companies have a female founder and only one percent have an African American founder. And just 75 percent of all venture capital is being distributed to just three states; California, New York and Massachusetts. Talent is everywhere; opportunity is not. And many of these elements are central to the stories that were at the core of our National Entrepreneurship Month blogs.

November 1st was both the first day of National Entrepreneurship Month and National Stress Awareness Day, so we kicked off our series with an examination of the role stamina and support plays in becoming an entrepreneur. We asked our #FacesofFounders entrepreneurs how they manage the stress of launching and running a business. See what they said in Confronting the Dark Side of Entrepreneurship.

On Veteran’s Day, we shined a spotlight on veterans in entrepreneurship and ways to support them. Our friends at Bunker Labs took to #FacesofFounders to share how the organization is working to build an ecosystem to support veteran entrepreneurs. Read what CEO Todd Connor had to say in How Bunker Labs Is Building an Inclusive Ecosystem for Veteran Entrepreneurs.

Then we looked back at the Essence Festival panel our senior vice president, Sheila Herrling, moderated with a group of entrepreneurial changemakers. Herrling shares some of the top takeaways from the informative and action-inspiring conversation in Changing the Face of Entrepreneurship.

Finally, to celebrate Small Business Saturday and #Giving Tuesday we focused on some of the many ways individuals can support entrepreneurs running businesses of all sizes. Not every entrepreneur has the same financial and social resources, and in Keeping Entrepreneurship at the Heart of the American Experience, we highlighted the many ways that individuals can support entrepreneurs in their daily lives and with the purchasing decisions they make.

We hope these stories has given you a chance to learn more about entrepreneurs, their valuable contributions and how you can support them. To learn more and to access a list of resources on these subjects, visit our website, follow our Medium publication #FacesofFounders and subscribe to Breaking Good, the Case Foundation’s weekly newsletter, to see more from us on entrepreneurship, race, place and gender.

There is much more work to be done and while Entrepreneurship Month may be over, we will continue to champion building onramps to entrepreneurship for all with the goal of everyone having an equal chance at unlocking the American Dream. We hope you will join us.

Keeping Entrepreneurship at the Heart of the American Experience

Entrepreneurs are vital members of our communities. The products and services they provide, innovation they spur and jobs they create are critical to the economic wellbeing of a community and a core part of the American Experience. As we have seen in the growth of the Impact Investing movement over the past ten years, entrepreneurs are also increasingly focusing part, if not all, of their efforts on addressing social and environmental problems that other stakeholders have been somewhat ineffective at solving.

While we know that the idea of entrepreneurs toiling away by themselves alone in a garage is a myth, while bringing forward these innovative new ideas, many entrepreneurs do spend a significant amount of time working by themselves or in small teams before their business gets to scale. It takes a village to get a startup off the ground, but building the community needed to succeed can be challenging. For example, 48 percent of women founders cite a lack of available mentors as a barrier to success and the average cost to launch a startup is around $30,000 with reports claiming that 80 percent of funding for new businesses comes from personal savings, friends and family. This creates additional roadblocks for entrepreneurs without wealthy friends and families.

We believe that entrepreneurs are only as strong as the community around them — investors, ecosystem builders, their team, supportive policy and you! As we approach Small Business Saturday and #GivingTuesday, we have rounded up some of the ways that anyone, anywhere can help entrepreneurs succeed.

Head to #FacesofFounders to read more about how you can support the entrepreneurship ecosystem…