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Writer's pictureBen Steenstra

19 Creative Startup Entrepreneurs Who Proved Their Bosses Wrong and Built Billion-Dollar Empires

Updated: Nov 21

Below are 19 examples of employees who turned into very successful entrepreneurs after being unable to innovate within the company they worked for. By starting their own businesses they demonstrate the challenges that employees can face when they try to challenge the status quo and what opportunities those companies can miss. By pursuing their ideas outside of the company, they were able to bring their innovations to market and achieve great success.


These examples also illustrate the importance of encouraging innovation and creativity within a company. Leaders should strive to create a culture that values playfulness, experimentation, and learning and provides employees with the support and resources they need to pursue new ideas and ways of working. By doing so, companies can unlock new sources of value and growth, and stay ahead of the curve in an increasingly competitive business environment.


Spanx: Sara Blakely’s $5,000 Gamble That Shaped the Shapewear Industry

Sara Blakely was working as a salesperson for a company selling office equipment when she came up with the idea for Spanx, a line of shapewear that became wildly successful. Blakely had initially tried to pitch the idea to the company she was working for, but they rejected it. Undeterred, she started her own business and quickly grew it into a multi-billion-dollar enterprise.


Sara Blakely Founder of Spanx

Sara Blakely’s journey to founding Spanx exemplifies the power of persistence and innovation. While working as a salesperson, Blakely encountered a personal frustration: traditional shapewear was uncomfortable and impractical. Recognizing a gap in the market, she used $5,000 of her savings to create a prototype by cutting the feet off a pair of pantyhose. Despite having no fashion or business background, Blakely taught herself the process of patenting and manufacturing her product.


After countless rejections, she secured a meeting with Neiman Marcus, where her passion and product won her first major retailer. Her relatable branding, bright red packaging, and word-of-mouth buzz turned Spanx into a household name, with a major boost from Oprah Winfrey, who named Spanx one of her "Favorite Things." Blakely’s relentless determination and ability to solve a simple yet universal problem transformed Spanx into a multi-billion-dollar empire.


Starbucks: Howard Schultz’s Global Vision for Coffee Culture

Howard Schultz was working as a marketing executive for Starbucks when he came up with the idea to transform the company from a small chain of coffee shops in Seattle into a global brand. However, the company's founders were resistant to the idea, and Schultz eventually left to start his own coffee company, which became Starbucks as we know it today.


Howard Schultz Founder of Starbucks

Howard Schultz’s vision transformed Starbucks from a small Seattle-based coffee chain into a global powerhouse. While working as a marketing executive for the company, Schultz was inspired by the vibrant coffee culture he experienced during a trip to Italy. He envisioned Starbucks as a place where people could gather, much like the Italian espresso bars, but his idea was met with resistance from the company’s founders.


Undeterred, Schultz left Starbucks to start his own coffee business, Il Giornale, which gained enough success to acquire Starbucks in 1987. Under his leadership, Starbucks grew into a global brand synonymous with premium coffee and community, showcasing how Schultz’s determination and bold vision reshaped an industry.


Dyson: James Dyson’s Five-Year Fight Against Vacuum Bag Giants

James Dyson’s journey to transforming household appliances began with a simple frustration: his vacuum cleaner’s poor performance and frequent clogging. As an engineer, he recognized the potential for improvement and drew inspiration from industrial cyclone technology to design a vacuum that would maintain powerful suction without the need for disposable bags. Over five years, Dyson meticulously worked on over 5,000 prototypes, perfecting his innovative bagless vacuum cleaner.


James Dyson Founder of Dyson

Despite his groundbreaking design, Dyson faced rejection from established manufacturers who were reluctant to disrupt their profitable vacuum bag businesses. Refusing to give up, Dyson launched his own company, Dyson Ltd., and introduced his vacuum directly to consumers. Its superior performance and sleek design quickly won over customers, propelling Dyson Ltd. to global success. Dyson’s story is a powerful example of how determination and the courage to challenge industry norms can lead to revolutionary breakthroughs.


3M Post-It Notes: The Sticky Solution That Almost Never Happened

The story of Post-It Notes is a remarkable example of how accidental discoveries and collaboration can lead to revolutionary products. In 1968, Spencer Silver, a chemist at 3M, invented a unique adhesive with a low tack—strong enough to stick to surfaces but easy to peel off without leaving a residue. Silver envisioned the adhesive being used for temporary applications, but his colleagues and managers at 3M dismissed the idea, as the company was focused on developing stronger adhesives at the time.


Spencer Silver inventor of 3m post-it

For years, Silver continued to promote his invention within 3M without much success. The breakthrough came in 1974 when Art Fry, another 3M employee, was frustrated with the bookmarks in his church hymnal constantly falling out. He remembered Silver’s adhesive and realized it could be the perfect solution. By applying the adhesive to small pieces of paper, Fry created a prototype for what would eventually become Post-It Notes.


Despite the innovative concept, the product faced initial resistance even within 3M, as executives doubted its market potential. However, a trial run in select markets showed that once people used Post-It Notes, they couldn’t imagine life without them. Launched nationwide in 1980, Post-It Notes quickly became a global phenomenon, revolutionizing the way people organize and communicate.


Dropbox: Drew Houston’s USB Problem Turned into a Cloud Solution

Drew Houston’s journey to founding Dropbox began with a personal frustration that many could relate to. While working as a programmer, he often forgot to carry his USB drive, leaving him without access to critical files. This inconvenience inspired him to create Dropbox, a cloud-based file-sharing and storage service that allowed users to access their files from anywhere. Houston initially pitched the concept to his employer, but they were uninterested in pursuing the idea.


Drew Houston co-founder Dropbox

Undeterred, Houston began working on Dropbox in 2007 with co-founder Arash Ferdowsi. They created a simple, user-friendly solution that quickly resonated with consumers. The breakthrough came when they launched a demo video showcasing Dropbox’s functionality, which went viral among early adopters and garnered widespread attention in the tech community. This buzz helped secure funding from prominent investors, including Y Combinator and Sequoia Capital.


Dropbox officially launched in 2008 and quickly gained millions of users, revolutionizing how people store and share files. Its seamless integration across devices and platforms, along with its freemium model, made it a go-to tool for individuals and businesses alike. Today, Dropbox stands as a pioneer in the cloud storage space, illustrating how identifying a widespread problem and offering a practical, scalable solution can lead to extraordinary success. Houston’s determination to pursue his idea independently highlights the importance of believing in your vision, even when others don’t.

company and grew Dropbox into one of the most successful tech startups of all time.


Under Armour: Kevin Plank’s Sweaty T-Shirt Frustration Transformed Athletic Gear

Kevin Plank’s journey to founding Under Armour began on the football field at the University of Maryland. As a player, he grew frustrated with the way cotton t-shirts absorbed sweat during games, becoming heavy, uncomfortable, and often chafing. Determined to find a better solution, Plank envisioned a new type of performance fabric that would wick away moisture and keep athletes dry and comfortable. After researching fabrics and experimenting with prototypes, he developed a compression shirt made from synthetic materials that addressed the issue.


Kevin Plank founder of Under Armour

Plank initially tried to pitch his idea to major sports apparel brands, but they dismissed it, believing there wasn’t enough demand for such a product. Undeterred, Plank started his own company in 1996 from his grandmother’s basement. Using $500 from selling t-shirts and a $40,000 loan, he began producing and selling his performance gear. His big break came when he convinced football teams to try his product, and word spread quickly among athletes about its effectiveness.


Under Armour soon expanded its product line and grew rapidly, thanks to aggressive marketing and strategic endorsements. Its 1999 ad in ESPN The Magazine drew significant attention, and Plank’s decision to outfit movies like Any Given Sunday with Under Armour gear helped elevate the brand’s visibility. Today, Under Armour is a global leader in athletic wear, competing with giants like Nike and Adidas.

GoPro: Nick Woodman’s Surfing Struggles That Redefined Action Cameras

Nick Woodman’s inspiration for GoPro came during a surfing trip to Australia, where he struggled to capture high-quality footage of himself riding the waves. Existing cameras were too bulky or impractical for action sports, so Woodman envisioned a compact, durable camera that could be worn or mounted to capture immersive footage. Initially, he tried pitching the idea to established camera companies, but they dismissed it, doubting the market potential for such a product.


Nick Woodman founder of GoPro

Determined to bring his vision to life, Woodman founded GoPro in 2002. Using $200,000 raised from his family and friends, he developed an affordable wrist-mounted camera with a 35mm film format. The breakthrough came with the launch of GoPro’s first digital camera in 2004, which resonated with adventure seekers, athletes, and content creators who wanted a reliable way to document their experiences. GoPro’s innovative design and functionality made it a hit, particularly in the extreme sports community.


Woodman’s marketing strategy was equally revolutionary. By encouraging users to share their GoPro footage, he created a powerful grassroots movement, leveraging user-generated content to promote the brand. Over time, GoPro evolved into a global leader in action cameras, expanding its product line to include drones, accessories, and editing software.


Zara: Amancio Ortega’s Vision of Affordable Fashion That Disrupted Retail

Amancio Ortega’s vision for Zara began while working in a small clothing store in Spain, where he observed inefficiencies in traditional retail models. He realized that affordable, fashionable clothing could be produced and sold more effectively by streamlining production and responding quickly to market trends. Ortega pitched his idea to his employer, but it was rejected, prompting him to start his own company in 1975.


Amancio Ortega founder of Zara

With limited resources, Ortega opened the first Zara store in A Coruña, Spain. He pioneered a revolutionary approach known as "fast fashion," where designs were quickly created, manufactured, and distributed based on real-time consumer demand. This model minimized excess inventory and allowed Zara to refresh its collections frequently, making it possible to offer trendy clothing at affordable prices.


Zara’s unique strategy included vertical integration, controlling every step of the production and supply chain. Ortega also prioritized customer feedback, using it to adjust designs and inventory rapidly. This adaptability, combined with minimal advertising and strategic store locations, helped Zara grow rapidly. Today, Zara is part of Inditex, the world’s largest fashion retailer, with a presence in over 90 countries. Amancio Ortega’s innovative approach to retail not only reshaped the fashion industry but also turned Zara into a global phenomenon, demonstrating how bold ideas and efficient execution can disrupt an entire market.


Slack: Stewart Butterfield’s Messaging Pivot That Revolutionized Teamwork

Stewart Butterfield’s path to founding Slack began with an unexpected pivot during the development of an online video game called Glitch. While working on the game, Butterfield and his team created an internal messaging system to streamline their communication. They soon realized that this tool, which was simple, efficient, and highly collaborative, had broader potential than the game itself. Excited by the idea, they pitched it to their employer, but it was rejected as it didn’t align with the company’s core focus.


Stewart Butterfield co-founder of Slack

Rather than abandoning the concept, Butterfield and his team decided to pursue it independently. In 2013, they founded Slack, turning their internal communication tool into a product aimed at businesses. With its user-friendly interface and integrations with other productivity tools, Slack quickly became an essential platform for teams looking to improve collaboration and reduce reliance on email. Its freemium model helped it gain widespread adoption, particularly among startups and tech companies.


Slack’s success can be attributed to its ability to address a universal workplace need for better communication while fostering a fun and engaging user experience. By 2019, the company went public, solidifying its status as a major player in the business communication space.


Groupon: Andrew Mason’s Rejected Pitch That Revolutionized Local Deals

Andrew Mason’s journey to founding Groupon began while working as a software developer in Chicago. He noticed that businesses often struggled to attract customers while consumers wanted better deals on local products and services. This inspired him to create a platform that would connect both groups through collective purchasing power, offering significant discounts if enough people participated in a deal. Mason pitched the idea to his employer, but it was rejected, prompting him to pursue the concept on his own.


Andrew Mason founder of Groupon

In 2008, Mason launched Groupon, short for "group coupon." The platform’s innovative model quickly gained traction, with its first deal—a pizza restaurant voucher—selling hundreds of coupons. Groupon’s appeal lay in its ability to offer win-win solutions: businesses gained exposure and new customers, while consumers enjoyed discounted prices. The company grew explosively, expanding to dozens of cities and countries in just a few years.


At its peak, Groupon became a cultural phenomenon, redefining how people discovered and interacted with local businesses. It went public in 2011, achieving one of the largest IPOs of the time. Although Groupon’s success faced challenges in maintaining its initial growth, Andrew Mason’s vision of leveraging collective buying power remains a testament to how innovative thinking and determination can create entirely new markets.


Nintendo Wii: Gunpei Yokoi and the "Fun over Power" Philosophy.

Gunpei Yokoi, a Nintendo employee known for creating the Game Boy, envisioned a new gaming console that emphasized simple, motion-based controls rather than raw graphical power. Yokoi believed this "fun over power" philosophy would make gaming more accessible to casual players. However, when Yokoi and his team pitched this idea to Nintendo's leadership in the late 1990s, it was dismissed. The company was focused on competing with Sony and Microsoft in the high-performance gaming console market.


Gunpei Yokoi - inventor of the game Boy

Determined not to abandon his vision, Yokoi eventually left Nintendo to pursue his ideas independently. His philosophy and early designs laid the groundwork for the Nintendo Wii, which was later adopted by the company after realizing the untapped potential of the casual gaming market. When the Wii launched in 2006, it became a massive success, selling over 100 million units worldwide and redefining gaming for families and non-traditional gamers.


Ford Motor Company: Henry Ford and the Quadricycle Vision

Henry Ford, before founding the Ford Motor Company, worked as an engineer at the Edison Illuminating Company in Detroit. While there, he developed the concept of a gasoline-powered vehicle called the Quadricycle. Excited about the potential of creating affordable automobiles for the masses, Ford pitched his idea to his superiors, hoping for their support. However, they dismissed his vision, as their focus was on expanding the electric grid and saw little value in personal vehicles powered by gasoline.


Henry Ford, founder of Ford

Undeterred by the rejection, Ford pursued his idea independently, building the Quadricycle in 1896. After refining his vision for mass production and affordable cars, Ford established the Ford Motor Company in 1903. His introduction of the Model T in 1908 revolutionized transportation and manufacturing, making automobiles accessible to everyday Americans and creating the assembly line process that shaped modern industry.


Pampers: Victor Mills and the Disposable Diaper

Victor Mills, a chemical engineer at Procter & Gamble (P&G), came up with the idea for a disposable diaper in the 1950s while caring for his grandchildren. Frustrated with the inconvenience of cloth diapers, Mills envisioned a single-use alternative that would save time and effort for parents. However, when Mills pitched the concept to P&G executives, they were skeptical, believing there wouldn’t be sufficient demand to justify the costs of development and production.


Victor Mills inventor of pampers

Undeterred, Mills assembled a small team to develop prototypes on his own time, eventually creating the first disposable diaper. After rigorous testing and refinement, P&G decided to take a chance on the product, launching it under the brand name Pampers in 1961. Pampers quickly became a massive success, revolutionizing childcare and creating an entirely new product category.


Disney: Ub Iwerks and Mickey Mouse

Ub Iwerks, an animator and collaborator with Walt Disney, was instrumental in creating one of the most iconic characters in entertainment history: Mickey Mouse. Before Mickey, Iwerks and Disney worked together at Universal Pictures, where they pitched a series of original character ideas. Their concepts, however, were often rejected or heavily controlled by the studio, leaving them frustrated by the lack of creative freedom.


Ub Iwerks, co-inventor of Mickey Mouse

When Universal took ownership of one of their earlier characters, Oswald the Lucky Rabbit, Disney and Iwerks decided to leave and start their own company. Iwerks drew the first sketches of Mickey Mouse, a character that would eventually redefine animation. Their first short film featuring Mickey, Steamboat Willie (1928), became a massive success, blending innovative animation with synchronized sound.


The story of Iwerks and Disney exemplifies how creative ideas, initially stifled by corporate constraints, can flourish in an environment of independence and collaboration. Their decision to leave Universal paved the way for Disney to become a global entertainment powerhouse, proving that belief in one’s creative vision can lead to groundbreaking success.


Tesla: Martin Eberhard’s Electric Vision Rejected by Big Automakers

Before co-founding Tesla, Martin Eberhard was an entrepreneur deeply interested in sustainable energy and electric vehicles. Frustrated by the inefficiency of traditional gas-powered cars, he envisioned a sleek, high-performance electric vehicle that would change public perception of EVs. Eberhard pitched the idea to several major automakers, including General Motors and Ford, but they dismissed it, believing electric cars lacked mass-market appeal and profitability.


Martin Eberhard co-founder of Tesla

Determined to bring his vision to life, Eberhard co-founded Tesla Motors in 2003 with Marc Tarpenning. They focused on developing the Tesla Roadster, a luxury electric car that combined cutting-edge technology with striking design. While Tesla faced many challenges, including funding and production issues, its debut in 2008 changed the automotive industry forever. The Roadster proved that electric cars could be both desirable and commercially viable, setting the stage for Tesla’s dominance under Elon Musk’s leadership.


Martin Eberhard’s story underscores how perseverance and a commitment to innovation can disrupt even the most entrenched industries, proving skeptics wrong and shaping the future of transportation.


Nike: Bill Bowerman’s Rejected Waffle-Sole Idea That Revolutionized Running Shoes

Bill Bowerman, a track and field coach at the University of Oregon, was obsessed with improving the performance of his athletes. He envisioned a lightweight running shoe with superior traction, inspired by the grooves of a waffle iron. Bowerman pitched the idea to major shoe manufacturers, but they dismissed it as impractical and unnecessary.


Bill Bowerman founder of Nike

Undeterred, Bowerman partnered with his former athlete, Phil Knight, to bring his idea to life. Together, they founded Blue Ribbon Sports, which later became Nike. Bowerman’s homemade prototype, created using his wife’s waffle iron, laid the foundation for the iconic "Waffle Trainer." This innovative design became a sensation in the 1970s, helping Nike establish itself as a leader in athletic footwear.


Bowerman’s story illustrates how a simple, innovative idea, initially dismissed by established companies, can revolutionize an industry when paired with determination and entrepreneurial spirit. Today, Nike’s legacy is built on the same pursuit of innovation that began with Bowerman’s waffle sole.


Adobe: John Warnock’s Rejected Idea That Became the Foundation of Desktop Publishing

John Warnock, a software engineer at Xerox, developed a revolutionary idea for a page description language (PDL) called "Interpress." This technology allowed text and graphics to be printed exactly as they appeared on screen, a game-changer for publishing and design. Warnock pitched the concept to Xerox executives, but they dismissed it, failing to see its potential beyond their existing hardware focus.


John Warnock founder of Adobe

Frustrated, Warnock left Xerox in 1982 and co-founded Adobe Systems with Charles Geschke. They refined Interpress into PostScript, the technology that became the foundation of desktop publishing. Adobe’s first major success came when Apple adopted PostScript for its LaserWriter printer, revolutionizing the printing and design industries.


Warnock’s story highlights how a rejected idea can flourish when paired with entrepreneurial vision and the willingness to take risks. Adobe’s success not only transformed publishing but also set the stage for innovations like PDF and Photoshop, cementing its role as a creative industry giant.


Twitter: Jack Dorsey’s Rejected Status Update Idea That Changed Social Media

Jack Dorsey, while working at Odeo, a podcasting platform, proposed an idea for a microblogging service that would allow users to share short status updates in real time. The concept was initially dismissed by Odeo’s leadership, who were focused on podcasting and didn’t see the potential for a service based on 140-character messages.


Jack Dorsey, co-founder Twitter

Undeterred, Dorsey collaborated with co-founders Biz Stone, Evan Williams, and Noah Glass to develop the idea outside of Odeo. In 2006, they launched Twitter as an independent project. The platform gained traction quickly, particularly during events where real-time updates became invaluable. By 2007, Twitter had taken on a life of its own, becoming a global social media phenomenon.


WhatsApp: Jan Koum’s Rejected Messaging Idea That Became a Global Phenomenon

Jan Koum, while working as an engineer at Yahoo, grew frustrated with the inefficiency of traditional SMS and email communication. He envisioned a simple, ad-free messaging app that would allow people to communicate instantly across borders. Koum pitched the idea to Yahoo’s leadership, but they dismissed it, focusing instead on their core advertising business.


Jan Koum co-founder WhatsApp

In 2009, Koum partnered with Brian Acton to create WhatsApp. The app emphasized simplicity, privacy, and reliability, quickly gaining traction among users who valued its ad-free model and ability to work seamlessly across devices. WhatsApp’s growth was exponential, particularly in international markets where expensive SMS charges were common.


By 2014, WhatsApp had over 400 million active users, leading to its acquisition by Facebook for $19 billion—the largest tech acquisition at the time. Koum’s story illustrates how staying true to a vision, even after rejection, can lead to creating one of the most widely used communication tools in the world.

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