From Side Hustle to Main Gig: Stories of Entrepreneurial Triumph


Starting a side hustle is often the first step towards entrepreneurship. It’s a way to test the waters, pursue a passion, or simply generate extra income. However, for some, what begins as a small venture blossoms into a full-fledged main gig. These success stories are not only inspiring but also a testament to the power of dedication and innovation. Let’s dive into the tales of entrepreneurs who turned their side hustles into thriving businesses.

Sarah Kauss – S’well

Sarah Kauss began S’well as a mission to reduce plastic waste with stylish, reusable water bottles. Starting as a side project, S’well’s popularity skyrocketed, and today, it’s a multi-million-dollar business that has made a significant impact on sustainability.

In 2007, Sarah Kauss founded S’well as an extension of her passion for the environment. She had recently returned from living in Bali for two years and was inspired by the amount of plastic waste she saw on beaches and in the water.

To combat this issue, she started Small Steps Wellness (SSW), a company that sold reusable water bottles made with recycled materials. She named the company S’well because she wanted it to be short and memorable — plus, it was easy to pronounce in other languages like Spanish or Italian!

SSW began selling its products at local farmers markets in New York City and quickly grew into a multi-million dollar business with distribution across North America and Europe. Today, S’well has sold over 15 million bottles worldwide and is available in more than 500 retailers across 50 states — including Target and Nordstrom — as well as online at

Brian Chesky, Joe Gebbia, and Nathan Blecharczyk – Airbnb

Airbnb was founded by Brian Chesky and Joe Gebbia, two recent graduates from the Rhode Island School of Design who were on their way to a design conference in 2007 when they had an idea for how to make some extra cash. The pair decided that instead of paying for hotel rooms during the conference, they would rent out airbeds in their apartment. They called their creation AirBed & Breakfast (A&B). Within just two months they were making $20,000 per month from this side hustle.

Over time, the idea grew into something bigger than just an alternative to hotels — it became a platform for connecting travelers with local hosts who could provide unique experiences in their own neighborhoods. This idea resonated with millions of people around the world and enabled Airbnb to expand beyond its original roots as an A&B business model into one that connects travelers with accommodations offered by local hosts all over the world.

Ben Silbermann – Pinterest

Ben Silbermann’s vision of a platform for discovering and sharing creative ideas led to the creation of Pinterest. What began as a side hustle has grown into a major social media platform, inspiring millions to curate their interests and passions.

The idea for Pinterest came about when Silbermann’s wife was looking at home decor ideas online and couldn’t find what she was looking for in one place. This inspired him to create an online pinboard that would allow users to save images they liked from around the web so they could easily find them again later — a solution that wasn’t available at the time. Today, pinterest has grown into one of the most popular social media platforms today with more than 150 million monthly active users worldwide.

Jennifer Hyman and Jennifer Fleiss – Rent the Runway

Jennifer Hyman and Jennifer Fleiss are the co-founders of Rent the Runway, a platform that allows millions to rent designer clothing and accessories. Rent the Runway was launched in 2009 while the two were studying at Harvard Business School. Today, Rent the Runway has become one of the fastest growing startups in history and is valued at $1 billion dollars.

Prior to starting their own company, Jennifer Hyman and Jennifer Fleiss worked for Google and Microsoft respectively. The two came up with an idea for Rent the Runway while brainstorming ways to improve their lives as young professionals in New York City. They realized that they were spending more money on clothes than they would like because they were buying outfits they would only wear once or twice. This led them to create a business model that allowed people to rent high-end fashion instead of buying it outright.

The idea took off quickly and within months had thousands of customers who were eager to rent designer dresses from brands like Tory Burch and Diane von Furstenberg (both now investors). The founders also attracted plenty of attention from investors who saw potential in their business model.

Julia Hartz – Eventbrite

Julia Hartz and her co-founders launched Eventbrite to simplify event planning and ticketing. Starting as a side project, Eventbrite is now a leading online ticketing platform, used by millions around the world to attend and host events of all sizes.

From the beginning, Julia’s vision was to create a company that could make life easier for busy people everywhere. She continues to be inspired by the fact that Eventbrite helps people connect with each other in meaningful ways, whether it’s sharing their passions or learning something new.

Julia has been recognized for her leadership at every stage for Eventbrite. She recently received the 2019 Forbes 30 Under 30 Rising Stars award in Enterprise Technology for her contributions to tech entrepreneurship and innovation.

These stories of entrepreneurial triumphs serve as a reminder that with dedication, innovation, and a keen understanding of market needs, a side hustle can evolve into a thriving main gig. They show that the path to success may be unconventional, but with perseverance, it’s possible to turn a passion project into a thriving business. So, if you’re nurturing a side hustle, keep going. Who knows? You might be the next success story we read about!

Remember, every entrepreneurial journey is unique, and while these success stories are inspiring, they also highlight the importance of individuality and innovation in the business world. Keep nurturing your side hustle, and who knows? It might just be the next big thing!

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