‘I’m gonna have to make my own money’: the rise of the side hustle | Entrepreneurs


In 2010, not long into my first job on a magazine now in the great magazine graveyard in the sky, a fellow junior and I were appraising the performance of a new intern. Fresh out of university, this person had arrived late and then suggested they conduct the celebrity interview for the next issue. “That’s the thing with these young ones coming through now,” my colleague said with a solemn shake of their head, “they just don’t want to put the graft in.”

Twelve years later and society is in a moment of transformation when it comes to work and our attitudes towards it. The Great Resignation – or at least the Great Thinking About Resignation – is upon us. The Covid pandemic smashed through many of the grand narratives we have passed down for generations about having a job: the need to be present in an office, the idea we are somehow indispensable to the wider machine we are operating in.

For older people already in charge, this meant scrambling to adjust the modern workplace to be more flexible and inclusive in the hope this would keep the young people in their organisations happy. But Generation Z already had other ideas. It’s not just that many of them entered the workplace in the era of Covid. It’s that they had already watched my generation – the pitiful Millennials – get sucked into a broken social contract, the one that promised if you found a good job and worked hard, you’d get ahead. They saw us stifled and infantilised by two recessions, mired in existential despair about the housing crisis and now vulnerable again as the cost of living crisis asserts its grip.

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Gen Z stand up to their employers in a way no previous generation has, something usually dismissed as a spoiled sense of entitlement. But in record numbers, they are also mobilising to establish incomes that don’t rely on their elders. They’re drop shipping, Amazon reselling, flipping designer sneakers, spread betting, investing in crypto and NFTs. They’re inventing their own cosmetic lines for TikTok, or selling homemade teeth grills on Instagram. They want to be famous on social media not just because it feels good but because they can monetise it in shrewd ways.

Some people call it a new golden age of entrepreneurialism, others the rise of the side hustle. But at the core of Gen Z’s attitude to work is a desire as old as capitalism itself – to be financially independent, to opt out of old-fashioned ideas, like having a boss, altogether. All of which begs the question: is the problem that they have unrealistic expectations and don’t want to put the graft in? Or do they – gulp – know something we don’t?

In 2014, when Adwoa Owusu-Darko was 15 and working in a greetings card shop, she’d buy new outfits rather than waste her wages on alcohol. “I wanted to look cool on non-uniform days,” she says, “but it wasn’t very practical. I was buying things I’d wear once, or that were ill-fitting and not really me.”

Then, in 2016, a friend mentioned she’d sold a pair of dungarees on an app called Depop, a social e-commerce platform where people were offloading unwanted clothes. Inspired to clear some space, Adwoa got out a camera.

“I decided to model, but I was uncomfortable showing my face,” she says. The solution she came up with – taking shots with the camera held in front of her face – became her signature aesthetic, different from the crumpled flatlays or limp coat-hanger shots elsewhere on the app. Soon Adwoa was being featured on Depop’s hallowed Explore page and, at 18, her store, Mini’s World, was born.

Depop is a proudly young space, with 90% of its active users under 26. It taps into many of the values cherished by Gen Z: sustainability, authenticity and the chance to buy from influencers rather than faceless corporations. Adwoa was able to support herself through university without needing a conventional job. An appearance on Channel 4’s Supershoppers saw Mini’s World take off and now she has a second business as a consultant helping other Depop sellers get started.

In May this year, Elite Business magazine published a report claiming that Gen Z entrepreneurs are leading the post-Covid recovery in the UK. It found that among the country’s sole traders, those from Gen Z are the only age group to have experienced annual increases in revenue during the pandemic. Despite this, one crucial distinction between Gen Z and previous generations may be how they measure success. After growing her business over lockdown, Adwoa – now 24 – took the decision to press pause.

“Towards the end of 2021, my mental health really suffered,” she says. “Even though I was doing well financially, I decided to downscale. I think Gen Z put a lot of emphasis on wellbeing and mental health, and being in an environment that really serves them. It is important to be mentally and financially stable, and one should not cost the other.

“I can wake up tomorrow and say: ‘You know what, I’m really not feeling great, I can take this day off and chill.’ Then the next day I can scale up and work from midnight to 5am if I want to. That is what gives me quality of life. That’s something to aspire to.”

Even prior to Covid, a 2018 report from Reading Business School had declared this the “age of the side hustle”, claiming it generates £72bn for the UK, or about 3.6% of GDP. And 16 to 24-year-olds are leading the charge.

‘I’ve always been kind of obsessed with money’: Jack Calvert, 20, from Middlesbrough, who posts advice online about affiliate marketing.
‘I’ve always been kind of obsessed with money’: Jack Calvert, 20, from Middlesbrough, who posts advice online about affiliate marketing. Photograph: Alex Telfer/The Observer

Scrolling through the TikTok hashtags of #hustle and #sidehustle, where countless creators – mostly young men – post updates about their quest for financial freedom, I came across Jack Calvert from Middlesbrough. He was discussing something called the Hustler’s University, an online course currently at the centre of controversy and feverish debate: does it truly unlock the secrets to getting rich from your laptop, or is it best avoided?

“I’ve always been kind of obsessed with money,” Jack, 20, tells me. “When I was a kid I used to sell raffle tickets to my family and pick a random toy from my bedroom as the prize.” He also tried – unsuccessfully – to make money online from streaming his Fifa sessions on Twitch and YouTube

Then, over lockdown, Jack – a year into an accountancy degree – got interested in the murky world of affiliate marketing. He says the method he used involved building a mailing list of email addresses via social media, then spamming them with other offers for various deals around the internet which, in turn, gave him a small referral fee should they make a purchase. Basically, the next time you get an email from an unfamiliar account promising “AMAZING IPAD DEALS”, it may well be a teenager in Teesside trying to launch their business empire.

Jack’s TikTok posts about passive income and affiliate marketing and various other digital buzzwords were averaging 400-500 views. In that time, he says, he made a total of £700 profit. But when he started posting about Hustler’s University, his views shot up, with some reaching hundreds of thousands. Since then he has started regularly going on TikTok live streams fielding questions from other would-be hustlers curious to know whether they should pay £39 a month to unlock Hustler’s University secrets.

So what are these secrets? Hustler’s University is an online academy that offers a series of lessons on things such as crypto investing, drop shipping and copywriting. Information on these topics is not hard to track down for free online, but what you get with Hustler’s University is an incentive to convince others to follow you: Jack, like all members, gets a 48% cut.

“The referrals were never the original goal, they’re kind of a happy bonus,” Jack insists, and so far he says he is sticking to his word by giving people an honest account of the programme’s merits. “I try to give a fair reflection. I always say: ‘It’s working fine for me, but it may not be worth it for you.’ Obviously you do get a lot of people falsely promoting it and claiming it’s going to be better than it is, which is quite scummy,” says Jack. “Though the course itself tells you not to do that.”

It may well, but one of the reasons Hustler’s University is so popular is that it is owned by Andrew Tate, a 35-year-old former British-American kickboxer, subject of an Observer investigation recently. Tate was ejected from Big Brother in 2016 after a video of him beating a woman came to light, although they both denied any abuse occurred and claimed it was harmless consensual roleplay. He now uses his Instagram feed to post pictures of himself with supercars and piles of money while promising followers they can achieve the same lifestyle. Tate is currently TikTok catnip where he posts a seemingly endless line of controversial soundbites ranging from why depression doesn’t exist to the various reasons women should be subservient to men. Whether he is truly the epitome of toxic masculinity or just putting it on for views is a subject for debate, but for many of the people giving him £39 a month in the hope it’ll make their wildest dreams come true, it’s beside the point.

When we spoke, after two months of spending an hour or two a day following the secrets of Hustler’s University, Jack says he has made only £2,000. But he insists he is learning useful skills and will focus on video game design and fashion next.

‘I’m gonna have to make my own money’: Ben Towers, who started his business aged 11, and sold it in 2017 in a merger that made him a millionaire.
‘It’s a fight or flight idea: I’m gonna have to fight’: Ben Towers, who started his business aged 11, and sold it in 2017 in a merger that made him a millionaire. Photograph: Sarah Cresswell/The Observer

If the tools Gen Z are using feel alien, the qualities that make a truly successful entrepreneur perhaps haven’t changed all that much. Ben Towers started his business aged 11 helping one of his mum’s friends make a website.

It was 2010 and Ben was given £50 for his efforts. Thrilled, he took his new skillset and tapped into the-then burgeoning online freelance world, helping more hapless boomers who wanted to keep pace with the digital age. He was so successful that his mother became nervous about the money he was making and insisted he hire a lawyer and an accountant.

“Eventually, I started moving more into marketing, because once these businesses had their website, they then wanted to know how to get people to visit them.” By the time he was 14, he was subcontracting other remote freelancers to help him manage the workload alongside his school work. At 17, he quit school early, employing himself as an apprentice to meet the criteria for doing so. By 18, he had scaled his business, Towers Design, to a team of 26. In 2017 he sold it in a merger that made him a millionaire.

Articulate, modest and polite, Ben, now 24, is often used as a poster boy for Gen Z entrepreneurialism in the UK. Ironically, for someone who never had much interest in joining a traditional workplace, his new venture Tahora, which he co-founded, helps big businesses such as Google, Natwest and the RSPCA make their workplaces more inclusive and appealing for younger workers.

In a sense, Ben is repeating the same trick that got him started at 11 by exploiting a knowledge gap between him and an older generation. In 2010, it was every business owner wanting a Facebook page; today, it’s that they want help satisfying a generation of employees who demand more than a salary and paid holiday. Get your workplace culture wrong – as a New York Times article from 2021 with the chilling title “The 37-Year-Olds Are Afraid of the 23-Year-Olds Who Work for Them” pointed out – and Gen Z will say: “Actually, we can leave and do whatever we want.”

Interestingly, Ben attributes this appetite for independence among his generation not to their aptitude for the internet as much as the sense of panic it has helped instil in them. “My generation has been exposed to a level of information that society has never seen before,” he says. “It used to be that you’d read a paper or sit down and watch the news once in the evening; now we open our phones 60 times a day. I think our experience of fake news has led us to just go: ‘I don’t trust the world, I’m not gonna get any opportunities coming my way.’ It’s a fight or flight idea: I’m gonna have to fight, I’m gonna have to make my own money.”

Adwoa, Jack and Ben all say they have benefited from relatively comfortable and supportive upbringings and that hustle culture can be dangerous for those who are less fortunate, or just naive. “The average entrepreneur earns less than the minimum wage,” Ben warns. “The vast majority do it because they love the challenge. For me, that’s very different to people who are just desperate to have the entrepreneur lifestyle.”

Talking to young people who are finding their own ways through the traditional career path – or just ignoring it altogether – is inspiring, but you also can’t help but feel angry on their behalf. I graduated during the 2007 recession, but spent my childhood cocooned in the 90s; Gen Z grew up witnessing the harsh realities of austerity, the housing crisis and spiralling personal debt – and had to be the first to navigate social media as children.

Rather than be broken by all of this, many have found creative ways to turn their digital nativism to their advantage and have embraced a concept we only pay lip service to – work-life balance – as a true ambition.

The more you see the world from Gen Z’s perspective, the more you realise how ridiculous it is to expect them to tackle the challenges we left behind by working tirelessly and without complaint for one corporation or another, hoping it’ll all be OK. They’re far too shrewd, too determined, too hopeful for that. Maybe we should be taking notes.

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‘I’m gonna have to make my own money’: the rise of the side hustle | Entrepreneurs

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