Ever wondered if the success of your startup rests on having to quit your job straight away?

Well, we’re here to show that this was never the case for some of the world’s most recognisable businesses. Delving into their stories can show us how choosing the side hustle route really can result in a success.

So let’s look at what we can learn from these five big name companies.

1. Craigslist

Back in 1995, Craig Newmark was sitting at his desk writing an email. He had this vague idea that he could send one every so often to keep his mates up-to-date with art and technology events in San Francisco. That first time he hit send, he had no idea the journey that moment would take him on. His friends loved it. One of them asked to add an available job, then an apartment. More and more people asked to be cc’d in. Within months, there was so much going into that email that he began a simple website allowing people to post things themselves instead. All the while he kept up his day job.

It would be another 4 years before Craig jumped shipped and concentrated on Craigslist full time. The wait was worth it, though, because Craigslist is now estimated to be worth over USD 3bn.

What can we learn from Craigslist?

Know what matters. Take a look at the Craigslist website. It still has the feel of one made in the 90s. People sometimes use Craigslist as an example of a business that was successful despite never innovating. But Craigslist know their market. They know they don’t need to change. Why spend all the extra money making a fancy website when there’s no need?

2. Udemy

Eren Bali didn’t get much sleep when he first started Udemy, the online learning platform. To fund the project he worked through the night as an engineer for Speedate, then used the money to craft his idea during the day. Yet coming from Turkey, he found that despite grinding away through practically every hour of the day for three years, it wasn’t enough to get the business the funding he felt it deserved. He knew he had to move to where the funding was.

By the time he upped sticks and relocated to Silicon Valley in 2010, he had a working platform and even staff to take with him. Ten years later he has one of the top online learning sites with over 40 million registered users.

What can we learn from Udemy?



Don’t take no for an answer. Be persistent. Not only did Eren make the bold move to relocate to a whole new country, but Udemy was rejected by more than 50 investors before things finally kicked in to gear. They kept searching and innovating, and in 2020, they raised USD 12m in funding on the back of Udemy’s exceptional growth.

3. Spanx

Sara Blakely new early on that she had a great idea when she came up with Spanx footless pantyhose, but she also knew it was going to be an uphill struggle getting the business off the ground. For a start, money was tight, so she had to keep the day job – selling fax machines door-to-door.

At one point, she recalls only having USD 5,000 to her name when she first approached attorneys to patent the idea, the exact amount they wanted to file paperwork. No worries, she thought, I’ll write it myself. And she did – learning how to do it on the fly.

She also found that no one truly understood the idea, mainly because most of the mills were owned by men. During her holidays, she would drive from mill to mill, introduce herself, make a pitch, receive a rejection, then drive on. Luckily one of the men she pitched to ran the design past his daughter, who told him it was a great idea and that he should help.

The daughter was, right. In 2020, Sara was reported to be worth USD 610m.

What can we learn from Spanx?

Do it yourself. Sometimes entrepreneurs find that a lack of capital slows them down and keeps them working the day job longer than they would like. But as Sara (and Eren from Udemy) shows, you can teach yourself. Sometimes we pay for a professional service because we think we have to, when in reality with a bit of research we’re more than capable of doing it ourselves.

4. Innocent drinks

Back in 1998, Richard Reed, Jon Wright and Adam Balon were on a snowboarding holiday. Sometime in between hitting the slopes and apres-ski, they started throwing a business idea around. They thought there was a gap in the market for healthy, good quality smoothies. The trouble was they didn’t know much about actually making them.

Returning home, all three kept up with their jobs in advertising and marketing. In the evenings and weekends they played around with recipes. The results tasted good to them, but how do you know for sure?

They decided to launched their product at a music festival, but also perform market research at the same time. They asked customers if they should turn the idea in to a fully-fledged business by offering two bins: one for yes, one for no.

Yes won comfortably, and they took this as a sure sign that they should resign from their jobs. In 2009 they sold a stake in Innocent drinks to the Coca-Cola Company for USD 40m.

What can we learn from Innocent drinks?

Listen to your customers. If you want to know whether the time is right to make the jump look at what your customers are telling you. Test your product or service with a select group, gather feedback and tweak the offering while still working your full time job. You’ll then have a handful of loyal customers ready for when you do finally take the full plunge.

5. Mailchimp

During the late 90s, Ben Chestnut was co-founder of a digital design agency. The company was doing well, but Ben and his partner realised that they needed to make an email marketing platform for a handful of their clients. They didn’t think that much about it. It was just an add on. One that didn’t even start making money until 2001.

Over the next six years they crafted the idea. A major sticking point was the need to automate it, for example. Then in 2007, they realised that Mailchimp had more potential than their actual agency, so they made the leap. By 2019, Mailchimp was creating USD 700m in revenue a year.

What can we learn from Mailchimp?

You might be reading this unaware that you even have a side hustle. Maybe you never realised that little side project going on in your current startup could grow into something big all by itself. That you really have two companies not one. Maybe it’s time to give it the attention it deserves?

Do what works for you

Ultimately, everyone’s situation is different. You have to weigh up what is right for you, your family and your business idea. As we’ve shown quitting your job isn’t a necessity, in fact you’ll probably know when the time is right.