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Thursday 19 June 2025 6:00 am  |  Updated:  Wednesday 18 June 2025 12:58 pm

Holly Tucker: I was lost after leaving Not On The High Street

By: Anna Moloney

Deputy Comment and Features Editor

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Notonthehighstreet founder Holly Tucker

We dig into the memory bank of the city’s great and good. Today, Holly Tucker, founder of retail behemoth Not On The High Street, tells us about leaving her business and setting up anew in Square Mile and Me

CV

    • Name: Holly Tucker
    • Job title: Founder and CEO of Holly & Co
    • Previous roles: Founder and CEO of Not On The High Street
    • Age: 48
    • Born: London
    • Lives: Richmond
    • Studied: University of life… I got an E in my Business Studies A-level
    • Talents: Reading a room, caring deeply about the small business community (some might say obsessed!) and I recently learned a grade 8 piece of piano after not playing for 40 years (much to Frank’s dismay as it took two and a half years for me to master one piece of music. I’ve been banned from the piano from now on).
    • Motto: “Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has” — Margaret Mead.
    • Biggest perk of the job? Shopping, I mean, it’s an actual business requirement to shop and support your own business! I consider it a talent and have put a lot of hours personally and professionally into small business shopping!
    • Coffee order: Latte but I am really an enormous tea drinker – builders. 
    • Cocktail order: Margarita, half salt, no ice
    • Favourite book: Sapiens by Yuval Noah Harari

    What was your first job? 

    My first ever job was cleaning the local pub at age 14! My dad used to drive me in for a 6.30am start and then (joyfully!) wait two hours for me outside to take me back home.

    What was your first role in the business world?

    My first ‘proper’ job was straight out of school. In fact I collected my A-level results on the day I got the role at Publicis Advertising Agency. I was the junior tea maker and eventually worked my way up to being the youngest account manager in London. I had amazing clients from L’Oréal and Renault, to Prestige & Collections. I had incredibly strong female mentors at this point in my journey. It was at times tough, but some serious skills were learnt for life!

    When did you know you wanted to build a career in retail or e-commerce specifically? 

    It wasn’t ever a conscious choice as such but after a very challenging period in my early 20s, I started a company called Your Local Fair, which brought hand-chosen, local small businesses under one roof at Chiswick Town Hall. I quickly realised that whilst it was electric bringing brilliant independents together in person, when it rained or there was a big football match on, the fairs would struggle. And then it dawned on me… a version of the event where the town hall could effectively be available round the clock, would be the internet. So the idea of Not On The High Street was born. 

    I had no experience in tech or in retail for that matter, yet with my business partner Sophie, we ended up building the third online marketplace in the world, after Amazon and Ebay (Etsy launched three months after us and at the time, Amazon only sold books). I never set out to become an entrepreneur, but I certainly had a very strong vision for shining a spotlight on UK small businesses and uncovering the hidden community of creatives and makers that were out there. I couldn’t wait to share them with others.

    What’s one thing you love about Canada? 

    London’s diversity. From Hampstead Heath and Notting Hill to Brick Lane and Shoreditch, every corner feels like a different world — and yet it’s all part of one extraordinary city.

    And one thing you would change? 

    There are some incredible independent shops online (especially at Holly & Co!) but I’m devastated by the lack of independents on our high streets. We were once a nation of shopkeepers – it’s what gave London its creative edge. Think of the Kings Road in the 60s and 70s! We need to nurture new talent, provide them with physical spaces to experiment and showcase their work, and revive the theatre and excitement of real-world retail. 

    What’s been your most memorable business lunch or meeting? 

    It was a meeting with an investor back in 2007. The tills had started ringing (finally!), and Not On The High Street was working – but we’d run out of money. The credit cards were maxed, both Sophie and I had young children (my son Harry was three months old when we launched) and we’d given it everything, but it felt like we’d come to the end. We got into the lift, and even my dad, who had been our greatest supporter and mentor (and financial director), held up both hands and said, “Well done. You truly gave it everything!” as if we were finished. And then someone came running to the lift with a bottle of fizz, and asked, “Where are you going?” Not On The High Street would live after all.

    And any business faux pas? 

    I once sent an internal memo to the head of UK L’Oreal by fax, and it caused a great deal of trouble! I realised too late, as I scrambled on the floor trying to pull the literal plug, to save my life. There was no recall of a fax! I felt like Marty McFly in Back to the Future with the famous scene of the electricity cable and the clock tower! I managed to keep my job!

    What’s been your proudest moment?

    I think it must be launching my second small business marketplace, Holly & Co. After leaving Not On The High Street, I was lost and never knew how I could – or would – ever do it again. Yet against the odds, I did. It wasn’t necessarily easier the second time around. In fact, I’d go as far as to say it was tougher in many respects, especially with the weight of expectations on my shoulders. But that moment of going live, well, it was just amazing. And I am immensely proud of everything we’re building it to be (watch this space)!

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    And who do you look up to?

    Edwina Dunn OBE (entrepreneur, business strategist and founder of the Female Lead). She is an incredible visionary and powerhouse whom I admire greatly.

    What’s the best business advice you’ve ever been given?

    “You can never unknow what you now know”, which to me, is about not turning a blind eye, and really taking action when you know something to be true. 

    And the worse?

    “It is what it is”, I’ve never liked that phrase. As someone who takes responsibility seriously, I believe we must challenge complacency, not accept it.

    Are you optimistic for the year ahead?

    I am eternally optimistic. I am very much a ‘cup half full’ type of person and I choose to live in gratitude. This attitude is not to be confused with idealism or being happy to turn a blind eye to all that is ‘wrong’. It’s just that as an entrepreneur, I’m solutions-focused. I can’t bear to dwell on the negative. If I can make a positive impact on the issues I see around me, I will seek to do so.

    We’re going for lunch, and you’re picking – where are we going?

    We’re off to The River Cafe. I interviewed Ruth Rogers last year on my podcast, Conversations of Inspiration (in its seventh year), and she has achieved something almost impossible: creating a brand that still maintains its integrity, sophistication and creativity at its heart, even after all these years. The food is exceptional, too!

    And if we’re grabbing a drink after work? 

    We’ll head to The White Cross in Richmond – a cosy and traditional pub if it’s cold, but if it’s a summer’s evening (especially after the office on a Friday night), we can stand outside as the sun sets on the river, and there’s always the added thrill of catching high tide and being flooded in! 

    Where’s home during the week?

    Richmond, or the office on Eel Pie Island in Twickenham. I’m biased, but it’s possibly the most creative and interesting office location in London!

    And where might we find you at the weekend?

    At home. I’m a real homebody and lucky enough to live very close to the river in Richmond so I often get to enjoy lovely, long dog walks. I also frequent Holt as often as I can, as it’s where my grandfather lived, and so I have many happy memories there (plus, the independent shops are fantastic, too). 

    You’ve got a well-deserved two weeks off. Where are you going and who with?  

    I’m going somewhere exciting with my husband Frank and son Harry. We enjoy going on adventures, and we recently returned from Mexico and Egypt. My son is studying archaeology at University, so we bribe him with the promise of ancient ruins to come on holiday with us! Next on the list is Bhutan to really know if GHN (Gross National Happiness) can beat GDP (which I rather think it must). Hope they have ruins!

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