Startups That Started As Side Hustles: Part 1

Sometimes it just takes one small idea that changes a side-hustle into a major success story.

Here, we explore the stories of how some impressive entrepreneurs took their “just for fun” projects and spun them into full time businesses. Let’s see how these dreamers turned their side gigs into headline-worthy successes!


Lynette Anderson: From Banking To A Booming Travel Business



Lynette Anderson’s journey from city banking to a successful travel entrepreneur shows the power of pursuing a passion. At 38, this mother of two made a bold decision to leave her 15-year banking career and venture into the travel industry with no prior experience.

She started by investing in a travel franchise, The Travel Franchise, after carefully researching and taking a significant risk with a bank loan. Balancing her demanding city job, Lynette worked evenings and weekends, quickly achieving an impressive £30,000 in sales in her first month.

Her dedication and hard work resulted in a huge £1.2 million in sales in 2023, culminating in a total of £2.6 million since the start of her journey. This transition from a secure job to a risky (yet fulfilling) entrepreneurial venture not only demonstrates Lynette’s go-getter attitude, but also highlights the potential of side hustles to evolve into lucrative careers, offering both financial success and personal satisfaction.

Vanessa Sanyauke: Making Change With Girls Talk And The Hill App


Vanessa Sanyauke | General Assembly


Vanessa Sanyauke’s evolution from a Head of Diversity and Inclusion at an international law firm and bank to a full-time entrepreneur shows her strong dedication to empowering women. Vanessa founded Girls Talk in 2013 as a side hustle while leading DEI strategies, creating a platform that connected over 56,000 women across 37 countries. This culminated in hosting the largest global Summit for Black women in tech and finance, with partnerships from giants like Meta and LinkedIn.

By 2021, Girls Talk’s success doubled her salary, leading Vanessa to focus on it full-time. She continued to expand and launched The Hill App in 2023, a tech tool designed to revolutionise job opportunities for women, especially in underrepresented sectors. The app, supported by leading corporations, shows her commitment to creating inclusive cultures.


Harry Reynolds: From Side-Hustle To Collectible Trading Cards Leader


Award-winning London Card Show brings sports cards, collectibles to UK collectors - Sports Collectors Digest


Harry Reynolds’ journey from a bank employee to the founder of the London Card Show is a tale of spotting potential. Starting as a side hustle, Harry used YouTube and social media to auction and upsell trading cards, quickly catching on to the sector’s potential. In 2021, during COVID-19, he took the leap, quitting his banking job to establish the London Card Show.

The show, now in its 11th edition, has grown from 10 to 550 tables, turning Sandown Racecourse, Esher, into a hub for trading card enthusiasts. Using modern technology like social streaming with Whatnot, the show not only connects collectors in real-time but also helps people make direct purchases.

Features like the Vlogger Zone and Virtual Reality Zone that appear at the show also make the experience one to remember, as they seamlessly blend technology with the vibrant, live atmosphere of the show.


Lucy Jeffrey: Turning Passion Into Profit For Conservation


Lucy Jeffrey | f:Entrepreneur


Lucy, a former HSBC employee, changed her career path by launching Bare Kind, a company dedicated to animal conservation through the sale of bamboo socks.

Beginning as a side hustle in 2018, Lucy felt the need to create a venture with a meaningful impact, transitioning from selling reusable straws to focusing on products that contribute to saving endangered animals.

Her commitment to this cause led her to leave her corporate job in 2020 to fully dedicate herself to Bare Kind. The business has grown year on year, with turnovers of £200k in 2021, £540k in 2022, and £520k in 2023. Lucy’s partner, also a former HSBC employee, joined her in this venture. Bare Kind’s success story is not just about financial gains but also about how with the right mindset, you can turn your passion into profit and make a difference!



Gene Caballero: From Corporate Tech To Lawn Care Leader




Gene Caballero’s entrepreneurial journey with GreenPal is a great example of how a side hustle can grow into a major business success.

Co-founding GreenPal while working at a Fortune 50 Tech company, Caballero and his team developed a platform that transformed the lawn care industry, earning it the nickname “Uber for lawn care.”

GreenPal simplifies the connection between homeowners and lawn care professionals, providing an efficient booking experience. Over five years, Gene’s vision, effort, and keen understanding of customer needs grew the business into a thriving company with an annual revenue exceeding $30 million. Today, GreenPal is a shining example of entrepreneurialism and innovation, showing just how a small side project can evolve into a big, successful enterprise.


Sam Pillar: From Coffee Shop Encounter To Tech Success


Sam Pillar - Jobber | LinkedIn


Sam Pillar’s story of founding Jobber is a great example of the power of chance.

Starting as a management consultant, Pillar quickly realised his true calling was in software development, particularly in creating solutions for small business owners.

The pivotal moment came in a coffee shop, where he met developer Forrest Zeisler. Sharing his vision, they co-created Jobber, initially designed to help a friend’s painting business, which soon revealed a broader market need.

Jobber, focusing on operational management software, has since experienced huge growth, raising over $175 million and serving more than 200,000 home service professionals across 60 countries. Pillar’s journey from a disillusioned consultant to the CEO of a company that has changed the home service industry shows the huge impact of innovative technology and the serendipity of entrepreneurship.

Anshika Arora: Bridging Culture And Technology In Wedding Planning


Anshika Arora - Founder - Eternity | LinkedIn


Anshika Arora’s entrepreneurial journey with Eternity shows just how personal experiences can ignite innovative business ideas.

While working in Mayfair at HSBC Private Banking, Anshika found her career lacked fulfilment. This coincided with her sister’s wedding, where she saw the complexities of planning a ‘Big Indian Wedding’. Seeing a gap in the market, Anshika used her finance background to bootstrap a tech platform aimed to simplify the process of South Asian wedding planning, a sector worth £5bn.

Within a year, the success of her side hustle encouraged her to commit full-time, turning Eternity into a 360 CRM software. Anshika’s transition from finance to entrepreneurship is a true blend of cultural understanding and tech innovation, creating a unique niche in the wedding planning industry.


Vanessa Jupe: Empowering New Mothers 


Vanessa Jupe - Leva | LinkedIn


Vanessa Jupe’s creation of Leva, a support app for new mothers, is an amazing journey from a side passion to a full-time business.

As an executive in a multi-billion dollar company, Vanessa saw a gap in support for new mothers dealing with challenges like breastfeeding and balancing motherhood with careers.

Her personal struggles as a new mother, coupled with the lack of resources, fuelled her to create a solution. Leva, born from this need, offers lactation and sleep support, career coaching, and health advice for mothers and babies, all within a supportive community. Transitioning Leva from a side hustle to her main focus has led it to impressive achievements, including thousands of downloads and partnerships with corporations. Leva stands as a testament to Vanessa’s vision of a holistic app that supports expectant and postpartum mothers, blending scientific research with practical guidance, transforming the way society supports motherhood and women in the workforce.