New gen bosses is a new series created to guide and inspire more people to go out there on their own, either as new business founders or freelancers. And what better way to do that than to ask the ones that already succeed at it? We want to know about big fuck-ups and even bigger successes, and the risky decisions they had to make along the way. We want to be the last little push you needed.

Job title: Managing Director 
Industry: Digital Marketing 
Company founder or freelancer: Founder
Company name: The Digital Fairy
How long have you been doing it: 7 years 
Age: 31
Location: East London

What pushed you to start on your own?

Soon after leaving uni, where I was studying communications, I knew I wanted to work in digital. I had an unhealthy addiction to the internet, between my friends, social media was our main communication tool—it was constant. At the time, brands were so boring online and I just had endless energy and ideas to connect them to a fairly untapped digital community. But there wasn’t one creative social media job role in London.

Two of my closest friends were successful business twins, they propelled me to start something, they believed in me and gave me a desk, a small loan, a forecast sheet and my first client, which was Bleach London (a small cult salon in Dalston now a household hair brand). Thanks, Sam and Lou. At the time, a lot of my friends in London were young business owners, creatives, freelancers so it felt scary but exciting and certainly not unattainable.

What was the very first thing you needed to do to set everything up?

Of course, I needed all of the above, but for this to work, I knew that I had to make myself invaluable to clients, so they couldn’t work without me. I was called ‘The Digital Fairy’ so I had a lot to live up to, I needed to graft and up-skill across every area—social media, copywriting, design, development and content creation. I was so basic at most of those things, but I knew when I would eventually recruit for those roles that I would understand the skills I needed.

What was the riskiest decision you had to take?

At the beginning, I was working with a lot of friends as partners, employees, suppliers and clients, and that was risky. There is so much to lose, and while it wasn’t always perfect, I learnt a lot and I gained a lot from starting in a bubble of trust, comfort and support.

What was a skill you didn’t foresee needing that you had to learn?

It sounds obvious but so much resilience. When you own a business it is inherently part of you and your identity, so when something goes a bit wrong it feels personal. It has taken years to begin to train my sensitivity so that I can leave a problem at the office, sleep at night and care less. You also naturally learn strength of character, to keep stable and solutions-focused when absorbing your team and clients’ energies, feelings and problems.

Everywhere around us, new gens are founding businesses and redefining their careers. New gen bosses is here to inspire those who might want to do the same, this time with extra tips, some lols from those who have been there, done that, and £20 in your new ANNA business account if you dare to take the leap.

At what moment did you realise that this was going to work out?

It wasn’t until 12 months—through a relationship and the case studies I’d been working hard on, I got my first big gig doing social media at The X Factor, at the time it was the biggest TV show in the UK and I was just there every weekend, so proud of myself. It led to conversations with other commercial clients such as Maybelline, Miss Vogue, ASOS… brands were beginning to shift into digital. To supply the demand I had to recruit a small team, at that point it just had to work out.

What did you spend your money on?

Like most DIY startups, apart from my essentials, I took a really nominal salary for the first 18 months. I reinvested everything I made back into the company to cushion myself and pay that loan back. I didn’t start spending money until I needed to pay for very junior staff. My next biggest expense would be small gifts and gestures of thanks, it was important that I fostered a culture of appreciation which I still try to keep alive today.

What was your biggest fuck up?

Nothing major to be honest, I feel lucky yet anxious to still be waiting for that big scary thing. But, early on everything was so DIY and scrappy, which made us who we are, but there was no process and I didn’t have the right communication tools. Clients were not contracted, projects were not scoped—everything was based on a vague and friendly understanding—which inevitably led to an abuse of trust and some unpaid invoices.

What was your biggest success?

My first few hires who started as interns have stayed and grown with the company for over 5 years, straight from uni. One is now a senior designer and the other an art director. Above everything and any project, it makes me feel incredibly proud to have created a culture where people can fulfil their long term ambitions, feel safe and develop with us.

What do you know now that you didn’t know then?

That business success to me isn’t about excessive profits and scale, it’s about retaining your personality and integrity, and those things can’t coexist.

What are three tips you would give someone who wants to start on their own?

One: Your business has to work around your personal needs. What are they?

Two: Invest in your staff and company culture—it’s so important.

Three: Don’t allow anyone to be passive in any role, everyone needs a self-starter attitude and everyone’s opinion matters.

Feel like unpaid invoices will never happen under your watch? There’s only one way to find out. Take the leap, open an ANNA business card completely free of charge for the first 3 months and get £20 in it, too.

Want to discuss taking the leap with other new gens? You’re in luck! We’ve created New Gen Bosses, a Facebook group to continue and expand the conversation started through this new series.

New gen bosses is a new series created to guide and inspire more people to go out there on their own, either as new business founders or freelancers. And what better way to do that than to ask the ones that already succeed at it? We want to know about big fuck-ups and even bigger successes, and the risky decisions they had to make along the way. We want to be the last little push you needed.

Job title: Co-founder & creative director
Industry: Advertising
Company founder or freelancer: Founder
How long have you been doing it: 5 years
Age: 35
Location: London

What pushed you to start on your own?

Three years prior to the birth of Superimpose I was fortunate to establish myself as a well rounded creative but the opportunity to step into the role of creative director wasn’t a clear path I can see. I remember just feeling like I’d hit a glass ceiling, I had big ideas but not the right team or clients to test them on.

What was the very first thing you needed to do to set everything up?

A client. It’s the advice I give to people now…be sure to know that initial phase of stability is guaranteed right from when you start. Too many people think the ‘build it and they will come’ theory is the way to go but it wasn’t an option I entertained. Lock in a small client that will cover your small overheads and build from there. It probably won’t be your dream client but it’s a great opportunity to test and learn and make your mistakes small when there isn’t everything at stake.

What was the riskiest decision you had to take?

Everything was about risk. Early on we had to present ourselves bigger than we actually were to convince clients to take chances with us. All those meetings we had with clients felt like we were suddenly going to get found out at that very moment. Five years on and only now do I realise that every single person in the room is as nervous as I was. Clients similarly feel like they need to pretend in their roles—so don’t be afraid.

What was a skill you didn’t foresee needing that you had to learn?

People management is by far the hardest thing you will deal with when running your own business. Nothing prepares you for it and it will take up most of your brainpower. Management courses are definitely advised.

Everywhere around us, new gens are founding businesses and redefining their careers. New gen bosses is here to inspire those who might want to do the same, this time with extra tips, some lols from those who have been there, done that, and £20 in your new ANNA business account if you dare to take the leap.

At what moment did you realise that this was going to work out?

I’ve always believed this was working for me from the very start but this year has been a real turning point through being recognised and awarded by those across the creative and advertising industries. You can have as much self-belief as you want but there is some safety and a level of gained confidence in knowing your peers and clients respect the work you’ve done.

What did you spend your money on?

For the first three years, we didn’t take any money out of the business because we were too scared. We did invest cost-effectively in our non-commercial platform SERVICES UNKNOWN projects to trial out new ideas and thinking.

What was your biggest fuck up?

The biggest mistake came early on which turned out to be a blessing in disguise. It was a situation that helped me understand the importance of ‘knowing your role’. We had just completed our first global campaign for adidas (relaunching the Stan Smith) and the campaign required minimal production so this led us to believe we could handle self-producing the next one. The following campaign came along and we tried to oversee all elements including the production and our lack of experience became very apparent. The shoot was an absolute fail and if it wasn’t for the relationship we had with our client then I’m not sure we’d be here today. That client supported us through thick and thin in the early days and I thank them for the opportunities given that has led us to flourish today.

What was your biggest success?

We’ve seen many successes this year with awards—2019 Studio of the Year’ by Creative Review and ‘Adweek100: Fastest Growing Agencies’ ranking Top 10 global, the biggest success for me is our partnerships with UAL and D&AD. My main aim when we began was to challenge how the ‘creative industry’ worked and I feel we’ve done that through opening doors for the next generation of creatives from non-traditional backgrounds.

What do you know now that you didn’t know then?

Advertising needs us more than we need it.

What are three tips you would give someone who wants to start on their own?

Invest in the right team—they say you’re only as good as your team and I firmly believe that.

Stay ambitious—treat every brief like it’s your last and think big.

Keep the public central in every decision you make—don’t get into this to win awards, make sure it comes from a good place.

Feel like you would have never made the same fuck up as Ollie? There’s only one way to find out. Take the leap, open an ANNA business card completely free of charge for the first 3 months and get £20 in it, too.

Want to discuss taking the leap with other new gens? You’re in luck! We’ve created New Gen Bosses, a Facebook group to continue and expand the conversation started through this new series.