5 Famous Businesses That Started As Side Hustles

From side hustles to success: Unveiling the unexpected journeys of five famous businesses

The journey from a modest side project to a multimillion-dollar enterprise is a testament to the power of passion, determination, and innovation. Through the stories of renowned companies like Airbnb, Etsy, WhatsApp, Spanx, and GitHub, we uncover how ordinary individuals transformed their passion projects into thriving businesses. 

Here, we have worked with James Dooley from Searcharoo to uncover the inspiring stories of how determined entrepreneurs took these five famous businesses from side hustle to success.


Airbnb began in 2007 when roommates Brian Chesky and Joe Gebbia, struggling to afford their San Francisco apartment, decided to rent out air mattresses on their floor to attendees of a design conference. With the help of Nathan Blecharczyk, they launched a rudimentary website to advertise their “Air Bed and Breakfast” concept. Despite initial setbacks and rejections from investors, they persisted, eventually attracting funding and growing the platform into a global phenomenon. Today, Airbnb boasts millions of listings worldwide and has revolutionised the travel and hospitality industry.

As James explains, ‘Airbnb’s story emphasises the importance of solving a personal pain point and persisting through challenges. Start small, focus on providing value, and iterate based on feedback.’


Etsy’s success highlights the value of catering to niche markets and fostering a community around a shared passion. Etsy was founded in 2005 by Rob Kalin, Chris Maguire, and Haim Schoppik as a platform to sell handmade goods and crafts online. An amateur woodworker, Kalin wanted to create a marketplace to connect artisans with buyers. 

Starting as a side project while Kalin pursued other ventures, Etsy gained traction within the crafting community, eventually leading him to focus on it full-time. Etsy grew exponentially through grassroots marketing and word-of-mouth, attracting millions of sellers and buyers globally.


WhatsApp was founded in 2009 by former Yahoo employees Brian Acton and Jan Koum, and the app’s journey underscores the importance of addressing a common pain point with a simple, user-friendly solution. James tells YCB, ‘Originally, Koum developed the app as a tool to provide status updates to his contacts while he was on a break from work. As the app gained popularity, Acton persuaded Koum to turn it into a messaging platform.’ 

Initially, WhatsApp faced rejection from major tech companies and struggled to monetize. However, its simple interface and focus on user privacy resonated with users, leading to rapid adoption worldwide. In 2014, Facebook acquired WhatsApp for $19 billion, solidifying its status as one of the most successful messaging apps. 


Spanx was founded in 2000 by Sara Blakely, who sold fax machines door-to-door before pursuing her idea of creating comfortable and slimming undergarments. Blakely started Spanx with $5,000 in savings and worked on the concept in her spare time while still employed. 

Her breakthrough came when she secured shelf space in Neiman Marcus stores, leading to widespread acclaim and demand for her products. Despite facing scepticism from industry experts and encountering manufacturing challenges, Blakely persisted and built Spanx into a billion-dollar empire, expanding beyond undergarments to include apparel and accessories.

‘Blakely’s story demonstrates the power of determination and resourcefulness in overcoming obstacles,’ James says. ‘What you should take from her experience is a willingness to embrace failure as part of the journey and the courage to leverage your unique perspective to disrupt traditional industries.’


Initially developed as a side project while Tom Preston-Werner was working as a software developer, GitHub was founded in 2008 as a platform for hosting and collaborating on code by Preston-Werner and his colleagues Chris Wanstrath and PJ Hyett. GitHub gained popularity within the open-source community for its intuitive interface and robust version control features. 

As demand grew, the founders transitioned to working on GitHub full-time, securing funding and partnerships with major tech companies. In 2018, Microsoft acquired GitHub for $7.5 billion, cementing its status as a leading platform for software development collaboration. GitHub’s success highlights the importance of fostering a culture of transparency and collaboration to attract users and drive adoption.

The stories of Airbnb, Etsy, WhatsApp, Spanx, and GitHub are potent reminders of the transformative potential inherent in side hustles. These companies, born from the ingenuity and determination of their founders, have not only revolutionised industries but also serve as inspiration to countless aspiring entrepreneurs worldwide. 

James Dooley notes, ‘Behind every multimillion-dollar enterprise lies the untold story of ordinary individuals who dared to dream, persisted through adversity, and turned their passion projects into reality. Their journey reminds us that with dedication and perseverance, no dream is too big to achieve.’

Charlotte Giver

Charlotte is the founder and editor-in-chief at Your Coffee Break magazine. She studied English Literature at Fairfield University in Connecticut whilst taking evening classes in journalism at MediaBistro in NYC. She then pursued a BA degree in Public Relations at Bournemouth University in the UK. With a background working in the PR industry in Los Angeles, Barcelona and London, Charlotte then moved on to launching Your Coffee Break from the YCB HQ in London’s Covent Garden and has been running the online magazine for the past 10 years. She is a mother, an avid reader, runner and puts a bit too much effort into perfecting her morning brew.