Entrepreneurship is often seen as a glamorous journey, but behind every success story lies a series of failures, setbacks, and lessons learned the hard way. For many successful businesspeople, failure is not just a stepping stone but the very foundation of their eventual triumph. In this article, we’ll focus on five entrepreneurs you might not hear about as often—yet their stories of overcoming massive failures are just as inspiring as the mainstream names we all know.
Milton Hershey: Failure to Sweet Success
Before Milton Hershey became synonymous with chocolate, he experienced multiple business failures. His first two ventures, a candy shop in Philadelphia and a caramel company in New York, both went bankrupt. By the age of 30, Hershey had lost nearly everything and returned home to Pennsylvania to live with his family.
Rather than give up, Hershey founded the Lancaster Caramel Company, where he developed a new caramel recipe that became wildly popular. With the success of this business, he was able to experiment with chocolate making, leading to the creation of Hershey’s Milk Chocolate—a product that would revolutionize the candy industry. The Hershey Company became one of the most iconic chocolate brands in the world.
Hershey’s story shows the power of persistence. Despite multiple bankruptcies, his belief in his product and willingness to adapt led to one of the most successful brands in history.
Reid Hoffman: From Social Networking Failure to LinkedIn Giant
Before co-founding LinkedIn, Reid Hoffman’s first attempt at building a social network, SocialNet, was a failure. Launched in the late 1990s, SocialNet was ahead of its time—it focused on online dating and social networking before either became mainstream. However, the platform failed to gain traction, and Hoffman eventually shut it down.
Learning from his experience with SocialNet, Hoffman shifted his focus to professional networking. In 2002, he co-founded LinkedIn, a business-oriented social network designed to help professionals connect and build their careers. LinkedIn grew rapidly and became the go-to platform for professional networking, eventually being acquired by Microsoft for $26.2 billion in 2016.
Hoffman’s story highlights the importance of adapting your vision. His failure with SocialNet taught him valuable lessons about timing and user needs, which he applied to LinkedIn’s success.
Sara Blakely: From Failed Saleswoman to Spanx Empire
Before founding Spanx, Sara Blakely worked as a door-to-door fax machine saleswoman and struggled to advance in her career. She faced constant rejection and even failed the LSAT twice, dashing her hopes of becoming a lawyer.
While working in sales, Blakely came up with the idea for Spanx after cutting the feet off her pantyhose to wear them under white pants. With her life savings of $5,000, she created the first prototype and relentlessly pursued manufacturers, all of whom initially rejected her idea. Eventually, Blakely convinced one to give her product a try, and Spanx became an overnight sensation, revolutionizing women’s shapewear and making her a self-made billionaire.
Blakely’s persistence, belief in her idea, and resilience in the face of rejection propelled her from struggling saleswoman to the creator of a global brand.
Nick Woodman: From Failed Gaming Venture to GoPro Success
Before founding GoPro, Nick Woodman’s first business venture, Funbug, a gaming and marketing platform, was a complete failure. Woodman had raised $3.9 million in funding for Funbug, but the business never gained traction, and Woodman lost almost all of the money.
After the failure of Funbug, Woodman took a surfing trip to clear his mind, where he realized there was no good way to capture action photos while surfing. This sparked the idea for GoPro. Starting with a wrist-mounted camera that allowed athletes to film themselves, GoPro became a major success in the action camera market, revolutionizing how people capture sports and adventure footage.
Woodman’s ability to turn failure into inspiration shows how crucial it is to remain open to new ideas, even in the face of major setbacks. His persistence turned a personal frustration into a billion-dollar company.
Jan Koum: From Welfare to WhatsApp Billionaire
Jan Koum, co-founder of WhatsApp, grew up in Ukraine under difficult conditions before moving to the U.S. as a teenager. His family struggled financially, relying on welfare for basic needs. Koum’s early career at Yahoo didn’t go as planned—he grew frustrated with the work and eventually quit without a clear path forward.
After leaving Yahoo, Koum and his friend Brian Acton developed WhatsApp, an encrypted messaging service focused on privacy. Despite facing rejection from investors early on, the app gained massive traction due to its simplicity and privacy features. WhatsApp eventually sold to Facebook for $19 billion, making Koum one of the wealthiest entrepreneurs in the world.
Koum’s journey shows how perseverance and a deep understanding of user needs (in his case, privacy and simplicity) can lead to massive success, even when the odds seem stacked against you.
Breakdown
For these entrepreneurs, failure was not the end—it was a catalyst for growth, learning, and ultimate success. Whether it was financial struggles, rejection from investors, or losing their first companies, each of these businesspeople used their setbacks to refine their vision and build something better. The key takeaway? Failure is often a stepping stone to greatness if you use it as an opportunity to learn, adapt, and persist.