5 examples of people who succeeded from a second income

For some people, a side hustle isn’t just a means to earn some extra cash, it’s a lifestyle. Dedicating time to earn a second income can be exhausting, time-consuming and downright tough at times, but if it’s your passion then it can also be rewarding. Really rewarding.

For some side-hustlers, what started out as a second job turned into something so much bigger. From an out-of-work bond trader who turned his love of photography into an internet sensation, to a woman whose mechanism for coping with depression transformed her into a YouTube millionaire; these are the people who saw their side-hustle sky-rocket…

#1: Brandon Stanton: Photographer and philanthropist


Back in 2010, Brandon Stanton was just another bond trader working in Chicago. He also happened to like taking photographs downtown on weekends. When he lost his job, he took a punt on his passion and moved to New York on a mission to photograph and document 10,000 of the city’s residents. The candid shots, accompanied with a brief bio of each subject, took Facebook by storm and the page now has close to 18m followers, so perhaps you’ve seen it: Humans of New York.

Today, Stanton has a fully-fledged media career that includes philanthropic work, public speaking, and of course, photography. As well as releasing several books, he has also turned Humans of New York into a series. You can watch new episodes every Tuesday over on his special Facebook Watch page.

#2: Lilly Singh: Vlogger and comedian


Lilly Singh had always dreamed of performing, but suffered from depression and lacked confidence. During the final year of her psychology degree, she began posting comedy skits on YouTube. They quickly gained traction and went viral.

Now, her Superwoman YouTube channel has over 12.5m subscribers, she’s appeared on the Jimmy Fallon Tonight Show, released a best-selling self-help book and has a lucrative contract with Smashbox cosmetics. Singh recently completed a world tour to support her book, where she visited 27 cities across 11 countries. Global domination beckons. All from a side hustle.

#3: A Girl Called Jack: Thrifty foodie


Jack Monroe was a single mum on benefits who was so cash-strapped that she would skip meals and avoid turning the lights on in her home, with her top priority to keep her toddler Johnny fed and housed. When she launched her thrifty food blog, A Girl Called Jack (now called Cooking on a Bootstrap), she never expected it to take off in the way it did.

Her posts explaining how she managed to feed herself and Johnny delicious food on just £10 per week became a hit, and she now gets close to 1 million hits per week. Monroe’s blog also highlighted issues surrounding modern poverty, as she spoke candidly about how she relied upon food banks and had to sell off her personal possessions.

Not only has she become a symbol of hope for those under financial strain, but her bestselling recipe books have won praise from the likes of The Guardian, for which she also vlogs on its YouTube channel.

#4: Kevin Systrom and Mike Krieger: Picture perfect pioneers


It’s hard to believe now considering it’s a massive money-making behemoth, but Instagram was only born in 2010, and initially created as a photo check-in app. Founders Mike Krieger and Kevin Systrom ran their side-hustle (then called Burbn) from a rented office space, working on it on evenings and weekends alongside their day jobs.

Burbn was a slow burner and only took off when the pair shifted the focus to mobile photography and changed the name to Instagram. The brand was acquired by Facebook in 2012 for a hefty £763m and is one of the most downloaded apps of all time, with over 800m active monthly users. It’s safe to say that Kevin and Mike have earned enough from their side hustle to buy their own office now

#5: J. Cole: Debt collector slash hip-hop superstar


The last side-hustler to feature on our list did things a little differently. Today, J. Cole is a global hip-hop tour de force, who sells out arenas the world over and has four hit albums under her his belt. But, even after he signed to Jay-Z’s Roc-Nation entertainment label Roc-Nation back in 2009, he didn’t rest on his laurels and continued working as a debt collector to pay his own bills.

Now worth a cool £5m, his days of door knocking are probably well and truly over. Which is good news given that he’s been on record stating that he wasn’t very good at it.

So, whether you side-hustle to fund your dreams, or live the dream through side-hustling, there is proof out there that hard work really does pay off. For more inspirational side-hustle cases, look at our blog.

7 common worries of people making money online

Read more

James: “I have never been happier”

Read more