Many dream of financial success, but think it’s impossible without a big investment or inheritance to start. The truth is, that some of today’s wealthiest entrepreneurs began with almost nothing. These self-made millionaires turned tiny investments—less than $1,000—into impressive business empires through creativity, hard work, and smart decision-making.
In this blog, I share the inspiring stories of 15 incredibly successful people who started with minimal capital but achieved remarkable wealth. Their journeys reveal valuable lessons about spotting opportunities, solving problems, and growing wealth from humble beginnings.
Brian Chesky – Airbnb Co-Founder
Brian and his roommate Joe Gebbia started Airbnb with an air mattress in their apartment and less than $1000 to build a basic website. During a design conference when all hotels were booked, they offered their floor space and breakfast, giving birth to “Air Bed and Breakfast.” Their early struggle was so severe that they sold specially designed cereal boxes called “Obama O’s” and “Cap’n McCain’s” during the 2008 election to fund their startup. Chesky built Airbnb into a company that disrupted the entire hotel industry, now valued at over $75 billion.
John Paul DeJoria – John Paul Mitchell Systems
Once homeless and collecting bottles for money, John Paul DeJoria started John Paul Mitchell Systems with just $700. He and his business partner made high-quality hair products and kept going despite many salons rejecting them, selling their products from his car trunk. Their strong belief in their products finally won over professional hair stylists who became loyal customers and helped promote the brand. DeJoria later co-founded Patrón Spirits, growing his fortune to several billion dollars by creating premium brands people loved.
Daymond John – FUBU
Using his mother’s sewing machine in Queens, Daymond John created FUBU (For Us, By Us) with only $40 worth of fabric. He worked multiple jobs while he and his friends made urban-style hats and clothes, selling them on street corners throughout New York City. John convinced his neighborhood friend LL Cool J to wear a FUBU shirt in a photo, which instantly made people trust the brand. His street-smart fashion company eventually made over $6 billion in worldwide sales, showing that clever marketing can work better than expensive advertising.
Jan Koum – WhatsApp
After moving from Ukraine as a teenager, Jan Koum taught himself programming through used books while depending on food stamps. He saved about $400,000 from his Yahoo engineering job and launched WhatsApp in 2009, focusing on creating a simple messaging app without ads that protected user privacy. Koum’s straightforward approach and focus on user experience helped WhatsApp gain hundreds of millions of users worldwide without traditional advertising. Facebook bought WhatsApp for $19 billion in 2014, turning this immigrant’s simple startup into one of technology’s greatest success stories.
Barbara Corcoran – The Corcoran Group
With a $1,000 loan, Barbara Corcoran started what would become a real estate empire in 1973. She rented a small Manhattan office and began matching people looking for apartments with available rentals, focusing on building relationships in New York’s competitive market. Corcoran made her business stand out by publishing the Corcoran Report, which analyzed the market in new ways and established her as a trusted expert. After selling her company for $66 million in 2001, she used her business skills as an investor on “Shark Tank,” further increasing her influence and wealth.
Pete Cashmore – Mashable
In 2005, at just 19 years old, Pete Cashmore launched Mashable from his bedroom in Scotland, without any investment money. He wrote every article himself at first, becoming an expert on new digital trends when regular news still ignored tech news. Cashmore’s regular publishing schedule and talent for explaining complex technologies in simple language quickly attracted millions of monthly readers. His passion project grew from a one-person blog into a global media company worth over $250 million, showing how expertise and good timing can create amazing value.
Sophia Amoruso – Nasty Gal
Searching for unique clothes in thrift stores and estate sales, Sophia Amoruso began selling vintage clothes on eBay with very little startup money. She carefully styled, photographed, and marketed each piece herself, creating a distinct style that appealed to young women looking for alternative fashion. Amoruso cleverly used MySpace to build her customer base when most stores hadn’t yet started using social media marketing. Her company grew from a solo eBay store to a fashion brand making millions in revenue, helping her become a self-made millionaire by age 30 despite starting with almost nothing.
Gary Vaynerchuk – Wine Library
Through innovative internet marketing with virtually no initial budget, Gary Vaynerchuk revolutionized his family’s modest liquor store. He pioneered wine video content in 2006 with Wine Library TV, shooting unpolished but authentic wine reviews that connected with viewers seeking honest expertise rather than pretentious commentary. Vaynerchuk’s energetic personality and genuine passion for democratizing wine knowledge helped increase store revenue from $3 million to $60 million in just a few years. His early recognition of digital content’s power led him to build a marketing empire worth hundreds of millions by applying the same authentic communication principles across multiple businesses.
Caterina Fake – Flickr
During the final days of her failing previous startup, Caterina Fake co-founded Flickr with almost no capital. She and her small team pivoted quickly to develop the photo-sharing platform as a last-ditch effort, focusing on building community features when competitors treated photos as simply static content to be stored. Flickr pioneered social features like tagging, commenting, and groups that created vibrant user communities around shared interests and photography styles. Yahoo acquired the company for approximately $30 million barely a year after launch, transforming Fake’s nearly zero-dollar investment into a fortune and establishing her as a visionary in social media.
Ingvar Kamprad – IKEA
At age 17, Ingvar Kamprad founded IKEA using a small cash gift from his father as a reward for good grades. The young businessman initially sold pens, wallets, and picture frames by going door-to-door in his small Swedish village before expanding into furniture through a mail-order catalog. Kamprad’s big idea came when an employee removed a table’s legs to fit it into a car, inspiring IKEA’s famous flat-pack furniture concept that greatly reduced shipping costs. His focus on affordable, practical design for everyday people transformed a tiny mail-order business into one of the world’s largest retailers with over 400 stores worldwide.
Andrew Mason – Groupon
While working other jobs, Andrew Mason developed The Point (which became Groupon) as a side project, investing minimal personal money in the initial idea. When his social activism platform struggled, he noticed one successful feature—group buying power—and boldly changed the entire business to focus exclusively on group discount deals. Mason’s timing was perfect, launching during the 2008 recession when both consumers and businesses desperately needed ways to save and make money. Groupon became the fastest company ever to reach a billion-dollar value, creating enormous wealth from what began as a small project despite Mason later being removed as CEO.
Yvon Chouinard – Patagonia
Using $825 he borrowed from his parents, Yvon Chouinard began making climbing spikes in his parents’ backyard. An experienced rock climber himself, he made equipment during climbing off-seasons and sold his hand-made gear directly to fellow climbers from his car at popular climbing spots. Chouinard’s business changed dramatically when he realized his original products were damaging rock faces, leading him to develop more environmentally friendly alternatives despite the financial risk. This early commitment to environmental responsibility became the foundation of Patagonia’s core values, helping build a billion-dollar company that focuses on sustainability alongside profit.
Arianna Huffington – The Huffington Post
With minimal money and working initially from her home, Arianna Huffington launched The Huffington Post with a small team of dedicated collaborators. She strategically used her large network to recruit unpaid bloggers and content contributors, creating a platform that mixed news aggregation with original perspectives not typically found in mainstream media. The site brilliantly took advantage of the growing demand for 24/7 news consumption and interactive commentary during a time when traditional newspapers struggled to adapt to digital realities. AOL bought the company for $315 million in 2011, just six years after launch, turning Huffington’s minimal investment into a media empire and establishing her as a digital publishing pioneer.
Mark Cuban – MicroSolutions
Fired from his job as a computer salesman, Mark Cuban started MicroSolutions with just $500 and slept on friends’ couches while building his business. He taught himself programming by reading manuals and staying up all night experimenting with new software when everyone else had gone home. Cuban differentiated his company by focusing on solving complex networking problems that larger competitors ignored, making him a trusted advisor to his small business clients. His dedication to understanding emerging technologies allowed him to sell MicroSolutions for $6 million in 1990, providing the capital for his later investments in internet radio (Broadcast.com) and the Dallas Mavericks basketball team, ultimately building a fortune worth billions.
Oprah Winfrey – Harpo Productions
Overcoming childhood poverty and abuse, Oprah Winfrey built her media empire after starting as a local news anchor in Baltimore. She transformed a failing Chicago morning talk show into “The Oprah Winfrey Show” through her authentic, conversational approach that connected deeply with viewers seeking genuine human stories. Winfrey made the pivotal decision to own her show rather than simply host it, establishing Harpo Productions with minimal startup capital but complete creative control. Her business acumen turned her personal brand into a multi-billion dollar media enterprise spanning television networks, film production, magazines, and digital platforms, making her one of the most influential self-made billionaires in entertainment history.
Phil Knight – Nike
Without formal business training, Phil Knight started selling Japanese running shoes from the trunk of his car at track meets with just $50 borrowed from his father. He partnered with his former track coach Bill Bowerman, who experimented with shoe designs by pouring rubber into his wife’s waffle iron to create better traction soles. Knight built relationships with runners by attending races across the country, gaining credibility as someone who truly understood athletes’ needs. His company, originally called Blue Ribbon Sports before rebranding as Nike, grew from $8,000 in first-year sales to a global sportswear giant worth billions, revolutionizing both athletic performance and sports marketing through iconic partnerships with athletes like Michael Jordan.
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