From Twitter to Slack, lots of the businesses we know and love started out as a totally different product
From Twitter to Slack, lots of the businesses we know and love started out as a totally different product

Six hugely successful businesses that started out as side hustles

You don't need to quit your day job to create a profitable business

Sirena Bergman
Wednesday 24 April 2019 11:31

Where once a job was a 9-to-5 you'd keep for a few decades until retiring, we are now living in a precarious job market with ever increasing automation and innovation. As a result, more and more people are diversifying their income, looking to their passions, hobbies and talents and finding a way to turn them into a lucrative side hustle.

According to figures released this week by the Association of Independent Professionals and the Self-Employed (IPSE), more than 320,000 self-employed people in Britain are working more than one job.

The number of people working for themselves has increased dramatically over the past two decades, jumping from 3.3 million in 2001 to 4.8 million in 2017. Today, an estimated 15 per cent of the population is self-employed, of which 7 per cent have launched additional businesses.

But the concept of the “side hustle” is not reserved for those eschewing traditional salaried jobs, as 40 per cent of people in full-time work are also increasingly using their free time to try and develop additional revenue streams.

It can feel like a hard slog, dedicating evenings and weekends to something with no guarantee it’ll take off, but when it does it can be life changing. Here are a few surprising examples:

1. Innocent Drinks


If you think side hustles are a recent millennial trend, think again. The founders of Innocent were university graduates in 1998 when they decided to try and make healthy smoothies on the side while in full-time work.

The founders only quit the day jobs after setting up a stall at a festival to sell their product. They asked their customers to drop their empty bottles into one of two bins labelled "yes" and "no" under a sign that said: "Do you think we should give up our jobs to make these smoothies?" The answer was a resounding yes.

The gamble paid off. In 2009, not long after a disastrous economic crash and in the middle of a recession, they managed to secure a $30m investment from Coca-Cola, which would go on to buy the rest of the company in 2013 for an estimated $320m.

2. Cards against humanity

A white card and a black card from Cards Against Humanity

Everyone’s favourite dinner party game started out as a side hustle its founders didn’t even know was a side hustle. In 2008, eight high school friends were hosting over 30 people, but realised there were few games that would work for that many people. That was when they unwittingly created the first prototype for what would soon become a cultural phenomenon.

Even when they closed a Kickstarter campaign in January 2011 having raised almost four times their original funding target, the founders continued to work on the company in their spare time. By 2013, the company had made reportedly made $12m.

The founders’ continued laid back attitude and quirky marketing stunts has seen the game remain popular, with new versions released on a regular basis to keep the product fresh and exciting.

It’s unclear whether all the founders still work in their day jobs, but it’s fair to say that their side hustle has likely made them all millionnaires.

3. Slack

What is Slack?

In 2009, Stewart Butterfield created Tiny Speck, a company intended to build a web-based, multiplayer game. But three years later it became apparent it wasn’t going to take off, but in the meantime the team of developers working on the project had created an instant messaging platform for the US and Canadian team to be able to communicate efficiently.

The company decided to try and make something of the product, and by the end of 2014 the company had raised $140m, making it the fastest growing start-up at that time. Earlier this year Slack announced it was getting ready to go public with a $10bn valuation.

And this isn’t the first time Butterfield has turned a side hustle into a hugely successful business. His first attempt at creating a computer game was in 2002. It was also unsuccessful, but the photo-sharing tool it included seemed incredibly popular – Butterfield saw the potential in the side project and pivoted his attention there. This would become Flickr, which sold to Yahoo in 2005 for over $20m.

4. Twitter

(Getty Images)

In the mid-2000s, Jack Dorsey was working as a web designer for a podcasting company called Odeo, but in his spare time he was trying to find a way to communicate with multiple friends who may not have SMS-enabled phones. He wanted to create a platform which allowed him to text in his messages and have them broadcast on a site which could be accessible on a desktop computer.

But it was only when iTunes announced it would include a podcasting platform in 2005, that Odeo employees were encouraged to come up with alternative projects. Dorsey took the idea to his bosses, former Googlers Ev Williams and Biz Stone, and their partner Noah Glass, who reportedly came up with the name “twittr”.

Now, 13 years after launch, Twitter continues to grow and thanks to his side hustle Dorsey is worth £5bn.

5. WeWork


While WeWork itself wasn’t exactly a side hustle, it did stem from one. Just over 10 years ago, Adam Neumann founded Krawlers, a baby clothes company based in Brooklyn, where he shared an office space with architect Miguel McKelvey.

With the business struggling, Neumann decided to rent out some of the spare office space, and McKelvey was on board. It quickly became apparent that their eco-friendly, trendy co-working space was worth more of their focus that their original business.

But by 2010 they realised they could do more with the concept. They sold their company Green Desk and used the money to fund WeWork, which is now one of the most recognisable co-working brands, with over 560 locations across the world and was recently valued at $20bn.

6. Airbnb

Airbnb is a classic example of how creative thinking allows entrepreneurs to make huge successes out of their setbacks. In 2007, two housemates in San Francisco were struggling to pay rent. They knew there was a big conference coming up, so decided to put some airbeds in the loft and market it as a bed and breakfast.

Before long, they realised their side hustle could actually become a business, but investors disagreed and more than a year later they were still broke, but they saw an opportunity in the upcoming Democratic National Convention. But to stay afloat they had to find a more immediately lucrative side hustle to fund their side hustle.

That’s when Joe Gebbia and Brian Chesky decided to make election-related cereal boxes which they would sell as a novelty – Obama O's and Cap'n McCains – at $40 each. Not only did this allow them to keep going with Airbnb, but it also showed grit and creativity which impressed investors and eventually landed them the funding they needed.

Their side hustle has since become a household name, and is valued at $38bn.

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