There are few British women we admire as much as Holly Tucker MBE (other than our co-founders Anna Jones and Debbie Wosskow OBE, of course). So, when Debbie got together with Holly (also know as “Hurricane Holly”, a nickname given to her for how quickly she gets things done) for an AllBright event on passion and purpose, we blocked out our diaries instantly. And, unsurprisingly, it was one of our favourite events to date...

Exploring how to create a career with passion and purpose, Debbie looked at Holly’s extraordinary path – going straight from school to what Holly calls the “university of life”. She started working in advertising, until at the age of 23, everything changed. Holly went through a divorce and was diagnosed with a brain tumour. It was through adversity that she came up with the idea for Not On The High Street, a unique marketplace which she co-founded in 2006 with Sophie Cornish where small businesses could sell their wares. At the time, nothing like it existed. 

Holly had never created a spreadsheet before she started Not On The High Street; and the pair ran out of money within six months (they raised investment quickly). Yet they’re case in point that a little naivety, as Holly says, can be a “tremendous” thing. Four years ago, Holly stepped down as CEO from the company, and went on to launch a small business consultancy called Holly & Co and in March 2020 launched SME:SOS, a free resource to support small businesses through the pandemic. 

She has also published a book, entitled, ‘Do What You Love, Love What You Do’ where she explores how for so long, “business” has been run by men who have tried to make it look like a dark art. Every year in the UK, men are starting 150,000 more businesses than women are. Over the course of four years, that amounts to a staggering £250 billion in revenue for the UK. Holly’s mission with Holly & Co is to change the narrative to make it inclusive. And as you’ll read here, she’s the woman to do just that.  

Here, we share some of the highlights from our event with Holly and Debbie. Make sure you sign up for AllBright+ to unlock our full event archive and watch the event here: allbrightcollective.com

We always like to start at the beginning at AllBright. Tell me about Holly Tucker at school. Were you always driven by passion and purpose from a young age?

I think I was quite a nightmare of a child. I wanted to get to the next level of everything three years in advance. I wanted to work at the age of 14, because I wanted my own money. I wanted to push boundaries and buttons. I found school relatively hard. I'm dyslexic, and academia did not come naturally to me, but I worked hard. I wanted to achieve, so I gave it my all. I did those classic entrepreneurial things such as starting the school top shop. I ended up being quite good at creative design and technology. I won the engineer of the year award when I was 16 for my recycling bin. I did try to do things differently, and I think that that's potentially what I've done all my life. 

You went straight from school to a job in advertising with clients including giants such as L’Oréal. By the time you were 25, you had experienced a successful career, serious illness, and a divorce after marrying your childhood sweetheart at the age of 22. One year later, at 23, you discovered you had an inoperable brain tumour. This led to you having to quit your job and at the same time, your marriage fell apart – looking back, how did you pull through this dark time?

It was really, really dark times. The other dark time in my life was stepping away from being the Not On The High Street CEO. These were the two moments I found myself flawed by life. I didn't know who I was. I really wanted to be married, I needed that stability in order to pursue what I wanted to do, and I think that that's what we all need. Don't we? We need that scaffolding and foundations. And so, my world shattered. Luckily, the brain tumor was something I could live with. It caused a lot of side effects, which meant that I had to leave permanent work and go freelance. When I look back, I was a baby. I do think though it all gave me a good wake up call to life. 

Let's talk about Not On The High Street - obviously,​ it has been a huge success story, and looking at it from the outside, it all looks peachy easy and straightforward. But I know it wasn't always a walk in the park. Tell me about launching this company?

We have this beautiful thing called naivety, and it’s tremendous. It gets a bad rap, but I think it's awesome, because if we had ever known what we know now, there was no way that our imposter syndrome would have been able to cope with what we were launching in the tech world. We were just solving a consumer problem, which was, we all want gorgeous, amazing, lovely things. And guess what? Small businesses create them. When we launched, we were teaching an entire community of small businesses how to sell online. At that point in time, people weren't confident to put their credit card details in the computer, you didn't have social media… I was always educating people. They’d ask me if they needed computer and printer to join notonthehighstreet.com, which sounds crazy now, but that is what we were doing. When I look back, we educated an entire community, but the rollercoaster started from the second we opened our mouth with this idea. 

Talk to me about your co-founder relationship with Sophie Cornish…

From day one, we did a partnership agreement, nothing official, but it went on paper. We asked ourselves all the hardest questions. We really went there - when are you a nightmare? What do you want to earn? What happens when the kids are sick? Do you want to be doing this for 20 years, 10 years, five years? What happens if we fall? 

We spent more time together than we did with our families. I had a three-month old baby when I started Not On The High Street, and I remember, after 52 weeks, we'd worked 50 weekends and weeks. The hours were insane – we’d work until 2am in the morning. The tales were unbelievable, but I learnt all about the power of two women! We were two people, but had the power of eight. 

In the early days, we were paying people off our credit cards and we weren't being paid. We were in the most difficult, darkest time. Our houses were on the line. I'd had a three-month old baby. I always think about the people who are doing this alone. I would imagine it is hard. I've never built a business without co-founders. 

You have to have that ability to shut the door with your co-founder, and say whatever you want to say, however wrong it is, and have someone who says the same back to you. Your imposter syndrome then doesn't get to flare up. You pull each other up again and get more Beyonce, but you still have someone to go to and cry your eyes out with. 

On stepping down as CEO from NOTHS four years ago, you’ve said: ‘I was in back-to-back meetings from 8am to 7pm, five days a week. I was under so much pressure I never felt I could walk to the loo, I had to run – and my PA would run after me. I saw my son for 20 minutes every night – I was turning into a “she-man” and that wasn’t the real me.’ Talk to me about the decision to step down…

My PA would run to the loo with me. So I didn't even get to wee in peace. She would tell me about the next meeting that was in my office already. When I launched Not On The High Street, I was 28 years old – I was young. All I knew was speed. I was known as ‘Hurricane Holly’, people came to expect the speed from me. 

I was what Not On The High Street brought me up to be. I was a CEO; a chairwoman; I had VCs sitting around a board table; I was growing a business very, very quickly. It was an unbelievable journey. I started to questions if I was building the company like an entrepreneur still, or was I actually building as a CEO? Two very different things. I realised that as time went on, I missed feeling connected. I was in a glass box office, back-to-back meetings, the C-suite, the VC world. I was very removed from the small businesses who I used to sit with and literally help them plan what their next jewellery range would be. 

I needed to become reconnected, and it was a very, very difficult time in my life to make the decisions to step down, to let Not On The High Street move on. I also knew I had something else in me. Meanwhile though, I lost all my identity. I had a bit of a breakdown - it was very, very difficult. But my co-founders now of Holly & Co, one is my sister, and the other, I always say I adopted her as a sister, they literally took the ashes that I was sitting in, and slowly but surely lifted me. That took a couple of years, but it happened. And now, I'm the happiest I've ever been. 

You went on to launch your own small business consultancy, Holly & Co and in March launched SME:SOS, a free resource to support small businesses through the pandemic. What do you want to achieve with Holly & Co?

Ultimately, what I felt at Not On The High Street from having this beautiful bird’s eye point of view was I wanted small businesses to be able to listen, touch, watch, read, experience. I wanted Holly & Co to be a fully immersive brand because I believe that that is absolutely the future, and I wanted to help create a home for small businesses, a virtual cheerleader, someone you can dip in and dip out of, to help you continue the journey. What I've done here is spent the last four or five years building a landscape of events, my podcast, conversations of inspiration, my book, my physical space, my blog, the hub, and there's a number of other things in the works.

How do you reframe failure in your mind to help you move towards new challenges and let go of past negative experiences?

I'm not addicted to failure, but I am absolutely super aware that through being shaken down, slightly tossed around in your life, mentally and with your ego, some of the best things happen afterwards. I have become a far better listener, I have become a far better boss, I've become a far better human being. Failure is inevitable, so there's no way you can't fail. If you have a problem with failure, you've got to have a big chat with yourself because you're going to be missing out on the gifts that I think have made entrepreneurs and successes what they are, because they've become friends with failure. It doesn't mean it's not painful, and embarrassing, and everything, but I have definitely become a better human being and businessperson for falling on the floor publicly and privately. 

I tell the team that I fuck up every week and I should fire myself every week. And I ask the team, "You fired yourself this week? Have you been embarrassed about a cock-up?" And if they say no, then you slightly want to go, "Well, I don't want you to be in the safe zone. That's not how we're going to progress."