25 Great Entrepreneurs Who Failed Harder and Won Bigger

A great entrepreneur isn’t just someone who builds a business. It’s someone who builds despite the odds. Great entrepreneurs are the ones who keep going when everyone else says “stop.” They’re the ones who take risks that others are too scared to take.

They don’t follow the rules—they rewrite them.

A great entrepreneur sees failure not as an endpoint but as part of the process. They adapt, they pivot, they find solutions. They build something that stands the test of time, not just because they want to make money but because they see a way to make life better, faster, easier, more meaningful.

I picked these 25 entrepreneurs because their stories do more than show us how to get rich—they show us how to think, act, and innovate. They’re not just American success stories. They’re universal lessons on grit, vision, and persistence.

They built things that changed industries, and the way they did it offers a roadmap for anyone, anywhere.

The 25 Great Entrepreneurs

These 25 entrepreneurs faced massive obstacles—bankruptcies, rejections, failures. They didn’t start out with all the answers, and they definitely didn’t have perfect paths. But that’s the point. They learned as they went.

And now you can learn from them.

If you’re an entrepreneur in the Philippines, these stories are packed with lessons you can use right now. Whether you’re running a small shop in the provinces or scaling up your tech startup, the challenges they faced are universal. They teach us how to handle competition, how to stay resilient when things get tough, and how to turn big dreams into reality.

So, dive in.

Discover how Steve Jobs revolutionized technology, how Oprah built an empire from scratch, and how Elon Musk is pushing humanity toward Mars.

Their stories aren’t just inspiring—they’re blueprints. Blueprints for how you can create, innovate, and overcome, no matter where you start.

1. John D. Rockefeller: The Man Who Turned Oil Into Gold

John D. Rockefeller didn’t start out rich. Born to a modest family in 1839, Rockefeller’s early life was shaped by hardship.

But where others saw struggle, he saw opportunity. By the time he was 31, Rockefeller had founded Standard Oil.

The secret to his success? Efficiency. He didn’t just drill for oil—he controlled every step of the process, from extraction to distribution.

But it wasn’t easy. He faced fierce competition, and people called him ruthless. The government eventually broke up his company because it became too powerful.

So how did Rockefeller handle these challenges? Instead of fighting the breakup, he embraced it. His companies thrived even more when split, turning them into giants like Exxon and Chevron.

Even when faced with roadblocks, you can turn obstacles into opportunities. Don’t be afraid to adapt when things change. Sometimes, breaking things apart can make them stronger.

2. Oprah Winfrey: From Poverty to Power

Oprah’s story is one for the ages. Born into poverty in rural Mississippi, she faced unimaginable hardship—abuse, racism, and a tough family life. But she had something no one could take away: the gift of storytelling.

She worked her way up through local TV stations, eventually landing her own talk show, “The Oprah Winfrey Show.”

Her biggest challenge? Being underestimated as a black woman in a world dominated by men. But Oprah didn’t let it stop her. She used her show to connect with millions, giving people a voice and tackling tough issues. Her ability to be vulnerable made her one of the most influential women in the world.

Your story is your power. Even if the odds are stacked against you, use what you have to create something bigger. Authenticity, empathy, and hard work can take you to places beyond your wildest dreams.

elon musk

3. Elon Musk: The Dreamer Who Refused to Settle

Elon Musk’s childhood wasn’t easy. He was bullied relentlessly in South Africa and later moved to the U.S. to chase his dreams. But Musk wasn’t content with just making money—he wanted to change the world. He started by co-founding PayPal, which he sold for millions, but that was just the beginning.

His next ventures? SpaceX and Tesla. But he faced massive setbacks. Rockets exploded. Tesla almost went bankrupt. Yet Musk persisted. He famously slept on the Tesla factory floor, working 120-hour weeks to keep his vision alive.

Today, Musk’s companies are pioneers in electric cars, space travel, and renewable energy.

Dream big, and don’t let setbacks stop you. Musk shows us that failure is just a stepping stone. If you’re relentless in your pursuit, no challenge is too big to overcome.

4. Sara Blakely: From Selling Fax Machines to Becoming a Billionaire

Sara Blakely didn’t come from wealth or have any special connections. In fact, she was selling fax machines door-to-door in Florida when she came up with the idea that would change her life—Spanx. She wanted a better pair of shapewear, so she made one herself.

But no one believed in her. Manufacturers told her it would never work. Banks wouldn’t lend her money. So she used $5,000 of her own savings and got to work. Sara even wrote her own patent! She faced rejection after rejection, but finally, a department store took a chance on her product.

Today, Spanx is a billion-dollar brand.

Don’t wait for others to validate your ideas. Take action, even if no one believes in you. Your grit and persistence can turn a simple idea into a life-changing success.

5. Sam Walton: The Man Behind Walmart’s Success

Sam Walton didn’t start with much. He bought a small store in a rural town and faced stiff competition from bigger retailers. But Sam had something others didn’t: a vision. He focused on selling at low prices and making shopping convenient for regular people.

He didn’t follow the trends of opening stores in big cities. Instead, he set up Walmart in small towns and cut costs by improving logistics. It wasn’t glamorous, but it worked.

Walmart became the biggest retailer in the world, known for offering low prices on everything from groceries to electronics.

You don’t need to follow what everyone else is doing. Sometimes, the best opportunities are in the places no one is looking. Focus on the needs of your customers, and don’t be afraid to break the mold.

These entrepreneurs faced adversity head-on. Whether it was growing up poor, dealing with rejection, or facing failure, they all found ways to push forward. Their stories prove that success isn’t just about talent or luck—it’s about persistence, hard work, and believing in your vision. Each one of them offers a lesson that every Filipino entrepreneur can apply in their own journey.

6. Bill Gates: The Boy Who Wanted to Change the World

Bill Gates wasn’t your average kid. He was a tech genius, spending hours coding in his school’s computer lab. Along with his friend Paul Allen, Gates saw that computers were the future. In 1975, they founded Microsoft with one goal: to put a computer on every desk in every home.

But success didn’t come without its hurdles. Microsoft faced fierce competition from giants like IBM, and Gates had to fight to get his software pre-installed on their machines. He worked tirelessly, often pushing his employees to their limits. Despite these challenges, Microsoft dominated the personal computer market, making Gates one of the richest men in the world.

Later, he shifted his focus to philanthropy, giving billions to global health and education initiatives.

Never stop believing in your vision, even when others don’t see it. Gates shows us that persistence, innovation, and hard work can turn a small idea into something that changes the world.

7. Mark Cuban: Turning Hustle Into Billions

Mark Cuban wasn’t born with a silver spoon. In fact, his first job was selling garbage bags door-to-door when he was just 12 years old. He didn’t just sell for money—he sold to learn how business works.

After several small ventures, Cuban eventually started a tech company called Broadcast.com during the early days of the internet. He saw the potential for streaming audio online—something no one else was really focusing on.

But his road wasn’t easy. Cuban faced plenty of rejection, and in the early days, many people didn’t believe in the idea of internet streaming. Still, he hustled, learned, and grew the company.

When Yahoo bought Broadcast.com for $5.7 billion in 1999, Cuban became a billionaire almost overnight. But instead of resting on his laurels, Cuban kept pushing. He became the owner of the NBA’s Dallas Mavericks, where he transformed a struggling franchise into an NBA champion.

Today, Cuban is known as one of the sharpest investors in the world, thanks to his role as a “Shark” on Shark Tank. His investment philosophy is simple: know your business inside and out, and never stop learning. Cuban constantly reminds people that success isn’t just about ideas—it’s about execution, hard work, and being willing to out-hustle everyone around you.

Cuban’s story shows that you don’t need to come from wealth to make it big. It’s all about hustle, learning every day, and staying ahead of the curve. Whether you’re starting a small business or dreaming of making a big splash, remember that hard work and street smarts can take you further than you ever imagined.

8. Mark Zuckerberg: Connecting the World One Like at a Time

Mark Zuckerberg didn’t set out to create one of the biggest companies in the world—he just wanted a way for Harvard students to connect. But what started as a dorm-room project in 2004 quickly grew into something much larger.

Facebook spread from campus to campus, then to the world. In just a few short years, Zuckerberg had built a platform that changed how people communicate, share, and stay connected.

Zuckerberg’s journey wasn’t without its challenges. He faced lawsuits from his co-founders, backlash over privacy issues, and competition from other social media platforms.

But through it all, Zuckerberg remained laser-focused on one thing: connecting people. He constantly pushed the boundaries of what Facebook could do, expanding it from a simple social network into a global platform that includes Instagram, WhatsApp, and more.

The key to Zuckerberg’s success? He understood that people crave connection, and he built tools that made it easier for them to share their lives with each other.

Today, Facebook (now Meta) is one of the most influential companies in the world, shaping the future of digital communication and social interaction.

Sometimes, the simplest ideas—like connecting people—can turn into the biggest businesses. Think about how you can solve a universal problem, and don’t be afraid to scale your solution beyond borders. Your small idea could end up changing the way the world works.

9. Charles Schwab: The Man Who Empowered Everyday Investors

Charles Schwab’s journey began with a simple but revolutionary idea: make investing affordable for the average person. In the 1970s, stockbrokers charged hefty fees, making investing accessible only to the wealthy. Schwab saw an opportunity to democratize investing by offering a discount brokerage service.

He faced heavy resistance from traditional brokers, who saw his low-cost model as a threat. But Schwab believed that if he could empower individuals to take control of their financial futures, his business would succeed.

His no-frills approach, combined with excellent customer service, made Schwab one of the largest brokerage firms in the world.

Schwab teaches us that businesses can thrive by focusing on serving the underserved. If you can offer people something valuable at a lower cost, success will follow.

10. Blake Mycoskie: Changing the World, One Pair of Shoes at a Time

Blake Mycoskie was traveling in Argentina when he noticed that many children didn’t have shoes. He wanted to help, but not through charity alone. Instead, he founded TOMS, a shoe company with a simple yet powerful model: for every pair of shoes sold, one pair would be donated to a child in need.

His “One for One” model was revolutionary, combining business with social good.

But it wasn’t easy—Blake had no experience in the shoe industry and faced skepticism from investors. Yet, he believed deeply in his mission and worked tirelessly to bring his vision to life.

Today, TOMS has given millions of shoes to children around the world, inspiring other companies to adopt similar business models.

Mycoskie shows us that business can be a force for good. Profit and purpose don’t have to be separate—find a way to give back through your business, and you’ll not only succeed but make a difference.

These entrepreneurs each faced their own unique set of challenges, but they all share common traits: resilience, vision, and a desire to make the world better in some way. Whether it’s empowering everyday people, changing an industry, or combining profit with purpose, their stories offer valuable lessons that Filipino entrepreneurs can apply to their own journeys.

11. Steve Jobs: The Visionary Who Revolutionized Technology

Steve Jobs wasn’t just an entrepreneur—he was a visionary. His journey wasn’t smooth, though. After co-founding Apple, Jobs was fired from the very company he helped build. But instead of giving up, he started new ventures like NeXT and Pixar. When Apple was struggling, they brought Jobs back, and it was here that he truly changed the world.

Under his leadership, Apple introduced the iPod, iPhone, and iPad—products that didn’t just meet market demands but created entirely new ones.

Jobs was obsessed with design, simplicity, and the user experience. He believed that people didn’t always know what they wanted until they saw it.

His perfectionism and passion made Apple one of the most valuable companies in history.

Jobs teaches us the power of resilience and reinvention. Even when life knocks you down, it’s your comeback that can define your success. Always think about how to make things better and simpler for your customers.

12. Joe Gebbia: Turning a Simple Idea Into a Global Hospitality Revolution

Joe Gebbia’s journey to co-founding Airbnb started with something most people can relate to—struggling to pay rent.

In 2007, Gebbia and his roommate, Brian Chesky, couldn’t afford their San Francisco apartment. With a design conference coming to town and hotels fully booked, they saw an opportunity: why not rent out air mattresses in their living room to attendees? That simple idea sparked what would become a multi-billion-dollar global company.

But the path wasn’t easy. Gebbia and Chesky faced constant rejection from investors. People couldn’t see how renting out spaces in strangers’ homes could ever become a legitimate business.

They had trust issues to solve, logistical hurdles, and an uphill battle to gain credibility in the hospitality industry.

But Gebbia believed deeply in the potential of the idea.

Airbnb tackled the trust issue head-on by creating a review system for both hosts and guests, ensuring transparency and safety. With persistence and innovative thinking, Airbnb quickly grew, transforming how people travel and stay around the world.

What began with air mattresses on the floor is now a company valued in the billions, connecting millions of people to unique travel experiences.

Gebbia’s story shows that the best business ideas often come from solving your own problems. He turned a personal struggle into a business model that disrupted an entire industry. Filipino entrepreneurs can learn that you don’t need a huge budget to start—sometimes all you need is a simple idea and the determination to see it through. Keep pushing forward, even when others can’t see the potential in your vision.

13. Walt Disney: Creating Magic From Nothing

Walt Disney didn’t just build a company—he built a world. But before Mickey Mouse, Disneyland, and billion-dollar franchises, Disney was just a young animator with a big dream and a string of failures. He was fired from a newspaper job for “lacking creativity.”

His first animation studio went bankrupt. But none of that stopped him.

In 1928, after losing the rights to one of his characters, Disney came up with Mickey Mouse. The world didn’t know it yet, but this little mouse was about to change entertainment forever.

But Disney didn’t stop there. He dreamed of creating a place where families could escape the real world—a theme park where imagination came to life. People called him crazy. They said it would never work. But in 1955, Disneyland opened, and it became an instant success.

Walt Disney’s biggest challenge was getting people to believe in his vision. But he pushed forward, fueled by his passion for creating magic.

Today, Disney’s legacy isn’t just a company—it’s a feeling. He turned dreams into reality, and in doing so, showed the world that anything is possible if you believe in it enough.

Don’t just build a product—build an experience. Whether you’re selling food, clothes, or services, think about how you can bring joy, excitement, or wonder to your customers. Dream big, and don’t let anyone tell you that your vision is too far-fetched.

14. Ben Cohen and Jerry Greenfield: Scooping Ice Cream, Stirring Up Change

Ben Cohen and Jerry Greenfield weren’t business moguls. They were childhood friends who decided to turn their passion for food into a business.

In 1978, after taking a $5 correspondence course on ice cream making, they converted a gas station in Burlington, Vermont, into their first scoop shop. The challenges? They had no real business experience and were competing with big ice cream brands. But what they had was heart—and a vision for doing business differently.

From the start, Ben and Jerry were about more than just ice cream.

They believed that business should be a force for good. They stood up for social causes, fought for environmental sustainability, and built their brand on values that resonated with people. Their quirky flavors and playful brand identity helped them stand out, but it was their commitment to social responsibility that made Ben & Jerry’s a beloved brand.

Their biggest challenge came when they faced pressure from corporate America to sell out or compromise their values. But instead of folding, they used their platform to raise awareness about important issues like climate change, racial justice, and fair trade.

Even after selling Ben & Jerry’s to Unilever in 2000, the founders ensured that the company stayed true to its social mission.

Ben and Jerry show us that business can be a tool for change. You don’t have to choose between profits and principles—you can build something that makes money while making the world better. For Filipino entrepreneurs, their story is a reminder that when you stick to your values, customers will support you, and your brand will thrive.

15. James Dyson: The Inventor Who Refused to Quit

James Dyson is the epitome of persistence.

He spent five years and built over 5,000 prototypes before perfecting his famous bagless vacuum cleaner. Most people would have given up after the first hundred failures, but not Dyson. His belief in his product was so strong that he kept going, even as banks and manufacturers turned him down repeatedly.

Eventually, Dyson launched his vacuum on his own, and it became a huge success.

Today, the Dyson brand is known for its innovative household products, from vacuums to hair dryers, all designed with the same commitment to quality and performance.

Dyson teaches us that failure is part of the process. Don’t be afraid of setbacks—embrace them. If you believe in what you’re doing, keep pushing forward, no matter how many times you’re told “no.”

These entrepreneurs didn’t just build businesses—they built movements and transformed industries. Their stories teach Filipino entrepreneurs that challenges are inevitable, but it’s how you face them that makes the difference. Whether it’s bouncing back from failure, finding a niche, or flipping the script on an industry, these leaders show that success comes from persistence, passion, and a willingness to innovate.

16. Jeff Bezos: Obsess Over the Customer

Jeff Bezos started Amazon in 1994 from his garage, selling books online. At a time when the internet was still new and few believed in e-commerce, Bezos saw the future.

But selling books was just the beginning. Bezos had a bigger vision—to create an “everything store” where customers could buy anything they wanted, with a few clicks.

Amazon’s early days were tough. Bezos took huge risks, investing heavily in infrastructure and logistics before the company turned a profit.

His obsession with customer experience, offering fast delivery and low prices, made Amazon stand out. He wasn’t afraid to fail either—he famously said, “If you’re not failing, you’re not innovating.”

Today, Amazon is one of the most valuable companies in the world, dominating retail, cloud computing, and entertainment.

Bezos teaches us to focus on the customer above all else. When you put the customer’s needs first and keep innovating, success will follow. Don’t be afraid to take big risks, even when the rewards seem far off.


17. Jack Ma: The Teacher Who Built Alibaba

Jack Ma wasn’t born into wealth. In fact, he failed the university entrance exam three times, was rejected from dozens of jobs (including KFC), and struggled to make ends meet.

But Jack didn’t let failure stop him. In 1999, he founded Alibaba, an e-commerce platform, with a group of friends in his small apartment in China.

Jack Ma saw the potential of the internet at a time when very few in China did.

His biggest challenge was convincing people to trust online transactions. Many thought he was crazy. But Ma was relentless, and his passion for connecting small businesses with the global market eventually paid off.

Today, Alibaba is a giant in e-commerce, fintech, and cloud computing, and Jack Ma is one of the most successful entrepreneurs in the world.

Jack Ma’s story is about resilience and believing in your vision, even when no one else does. Failure is just a stepping stone. For Filipino entrepreneurs, Ma shows that success often comes after multiple setbacks, and it’s your persistence that matters most.

18. Emily Weiss: Building a Beauty Empire with the Power of Social Media

Emily Weiss started Glossier in 2014, but her path to success began years earlier with her beauty blog, Into the Gloss. She listened to what her readers wanted—beauty products that were simple, effective, and accessible.

Using the insights from her blog, Weiss launched Glossier, a direct-to-consumer beauty brand that quickly became a hit.

Weiss didn’t have the backing of a big corporation. She relied on building a community through social media, letting her customers shape the brand.

She was transparent, asked for feedback, and gave her audience a sense of ownership in Glossier’s growth. Her approach disrupted the traditional beauty industry, turning customers into brand advocates and ambassadors.

Weiss teaches us the power of community. Filipino entrepreneurs can learn that engaging with your audience, listening to them, and making them feel like part of your journey can lead to incredible growth.

19. Reed Hastings: Streaming Success After Failure

Reed Hastings wasn’t always successful. Before Netflix, he co-founded a software company that struggled and eventually failed.

But Hastings didn’t quit. Instead, he started Netflix as a DVD rental service that sent movies by mail. His big challenge? Competing with established video rental stores like Blockbuster.

But Hastings saw where the future was heading—online streaming. In 2007, Netflix began offering movies on demand, allowing customers to stream content directly to their devices.

While many doubted the move, Hastings was right. Netflix transformed how people consume media, turning from a DVD rental service into a global streaming giant that produces award-winning original content.

Hastings teaches us to pivot and embrace change. Sometimes, the key to success is seeing where the market is going and being brave enough to lead the way, even when others doubt you. Don’t be afraid to disrupt the status quo.

20. Pat Brown: Changing the Food Industry, One Burger at a Time

Pat Brown wasn’t a businessperson—he was a scientist. But his vision was to make a huge impact on the environment by reducing meat consumption.

In 2011, he founded Impossible Foods with a goal: to create plant-based meat that tastes just like the real thing. His biggest challenge? Convincing meat-eaters to try it.

It took years of research, and many told him it couldn’t be done. But Brown persisted. Impossible Foods finally launched its plant-based burger, and it became a sensation.

Restaurants like Burger King added it to their menus, and today, it’s part of a growing movement toward sustainable eating.

Brown’s story is about using innovation to solve a global problem. Filipino entrepreneurs can learn that combining passion with purpose can create a business that not only thrives but also makes a difference. Don’t be afraid to take on big challenges and think about how your business can help the world.

These entrepreneurs show that success often comes after repeated failures, pivots, and leaps of faith. Their journeys highlight the importance of resilience, customer focus, innovation, and adapting to change. Filipino entrepreneurs can draw valuable lessons from each of them: don’t fear failure, listen to your audience, and always be ready to see where the future is headed.

21. Ray Kroc: The Man Who Made McDonald’s a Global Empire

Ray Kroc was already in his 50s, selling milkshake machines, when he discovered a small burger joint run by the McDonald brothers.

He saw something others didn’t—a business model that could be scaled nationwide. Kroc convinced the brothers to let him franchise their restaurant, and soon after, he bought the company entirely.

But it wasn’t easy. Kroc faced constant financial pressure, aggressive competition, and legal disputes with the McDonald brothers.

Yet, he pushed forward, standardizing the menu, perfecting operations, and creating the fast-food model that is now used worldwide. His focus on consistency, efficiency, and franchising transformed McDonald’s from a single restaurant into a global giant.

Kroc teaches us that it’s never too late to start something new. He didn’t create McDonald’s from scratch but saw an opportunity and ran with it. Sometimes, success comes from recognizing a good idea and making it bigger and better.


22. Tom Love: Turning Gas Stations into Roadside Comforts

Tom Love and his wife Judy started small, leasing an abandoned gas station in Watonga, Oklahoma, with a $5,000 loan.

Love’s Travel Stops didn’t just sell fuel—they offered convenience. Tom expanded his stores to offer 24-hour service, restaurants, and travel items, turning his gas stations into one-stop shops for road travelers.

The challenge? Competing against giant fuel companies. But Love focused on something the big guys overlooked: customer experience. His stores became a haven for travelers, with clean restrooms, quality food, and friendly service.

Today, Love’s Travel Stops operate over 600 locations across the U.S.

Love’s story shows that no matter how small you start, focusing on the needs of your customers can make you stand out. Filipino entrepreneurs can learn to turn simple services into exceptional experiences.

23. Whitney Wolfe Herd: Changing the Rules of Dating

After leaving her role at Tinder, Whitney Wolfe Herd felt sidelined and disillusioned. But she didn’t let that stop her. She took what she learned and created Bumble—a dating app where women make the first move. This small change flipped traditional dating dynamics and empowered women in a way that hadn’t been done before.

Wolfe Herd faced backlash, lawsuits, and skepticism, but she pushed forward with her vision. Today, Bumble is more than just a dating app—it’s a platform for friendships, networking, and empowerment. In 2021, Wolfe Herd became the youngest female CEO to take a company public.

Wolfe Herd’s story teaches us to take control of our own narrative. When you see a problem, create a solution. Don’t wait for someone else to fix it. Innovating small details can lead to big changes in your industry.

24. John Johnson: The Publisher Who Gave a Voice to the Unheard

John Johnson grew up in poverty during a time when African Americans were rarely represented in mainstream media. He decided to change that.

In 1945, Johnson launched Ebony, a magazine that celebrated Black culture and achievements. Later, he founded Jet, which focused on current events affecting the African American community.

The challenges were immense. Johnson struggled to find advertisers and financial backing, but he persisted. He knew his community needed representation, and he made it happen.

Ebony and Jet became cultural cornerstones, amplifying voices that had long been silenced.

Johnson teaches us that business can be a tool for change. If you see an underserved community, find ways to amplify their voices. Filipino entrepreneurs can make a real impact by focusing on representation and inclusion.

25. Howard Schultz: Building Starbucks Into a ‘Third Place’

Howard Schultz didn’t start Starbucks, but he took it to heights no one imagined.

After visiting coffeehouses in Italy, Schultz envisioned Starbucks not just as a place to buy coffee, but as a “third place” between home and work where people could relax, connect, and enjoy their time. He wanted Starbucks to be more than a coffee shop—it had to be an experience.

Schultz faced resistance from Starbucks’ original owners, who didn’t want to expand in that direction. So, he bought the company himself and started his transformation.

By focusing on premium coffee and creating a cozy atmosphere, Schultz built Starbucks into a global brand that is synonymous with the coffee experience.

Schultz’s journey shows that great businesses offer more than just products—they offer experiences. Filipino entrepreneurs can focus on creating spaces where people feel connected and valued, turning customers into loyal patrons.

Curious if you’re really playing at your best? Find out with the A-Game Scorecard. It takes just a few minutes. Every answer shows if you’re pushing your limits—or holding back in the safe zone. Take your A-game Scorecard.

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