Humble beginnings: The story behind Not on The High Street

Holly Tucker’s journey as an entrepreneur wasn’t mapped out by a structured plan or a robust strategy. Instead, it was fuelled by a passion for helping people celebrate with unique gifts, supporting creative entrepreneurs, and building a business that mattered.
In 2006, at the age of 28 and with a three-month-old baby, Holly co-founded Not on The High Street. This online marketplace would give independent makers, artisans and small businesses a platform to sell their unique products. The marketplace concept was almost unheard of at the time, except for giants like Amazon and eBay. Holly and her team were essentially building something from scratch without a schema to follow.

This naivety, rather than being a hindrance, became one of her greatest strengths. In a podcast with The High Performance Podcast, she recalls how if she had fully understood the challenge of what she was taking on, she may never have started. But her optimism and unwavering determination kept her moving forward.

Let’s take a look at Holly Tucker’s story and what she revealed in her conversation on The High Performance Podcast.

Juggling entrepreneurship and financial struggles

Building a business while balancing family responsibilities and financial pressures was challenging. Holly had a newborn baby and a household to support, yet she poured everything into making Not on The High Street work.

Financial safety net? Investors funding the vision? Holly didn’t have any of that. She worked a day job while setting up the business as a side hustle, gradually developing the company until it required her undivided attention.

In her appearance on the The High Performance Podcast, Holly advises “if you can bootstrap it and side hustle, build up some cushion so that you can actually feel… not that fear because there’s nothing like money fears to paralyse you”.

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Once Not on The High Street took off, it consumed nearly every waking hour and demanded constant problem-solving, not to mention relentless drive.

For many aspiring entrepreneurs, the fear of financial instability stops them from starting. Holly’s experience proves that there are ways to balance risk, whether that’s keeping a stable job initially or building the business gradually.

Imposter syndrome and self-doubt

Despite her success, Holly has battled imposter syndrome throughout her career – something she believes many women in business experience.

The imposter syndrome stops you getting carried away with your ego. If I didn’t have imposter syndrome, it would mean that I would not double, triple, quadruple check everything that I write. You know, everything that I go and do, I research and prepare. And so I actually call it a blessing.

Instead of seeing imposter syndrome as a barrier to confidence, she reframed it as a superpower. It has made her work harder, prepare more thoroughly, and never take success for granted.
This perspective is a powerful lesson for any entrepreneur struggling with self-doubt: doubt doesn’t mean you aren’t capable, it means you care.

The pressure of being the sole breadwinner

As Not on The High Street grew, so did the pressure on Holly’s shoulders. Within a few years, she had become the sole breadwinner for her family, a weight that many entrepreneurs, particularly women, can relate to.
Her husband, who worked in the public sector, was more risk-averse and concerned about the uncertainty of running a business.

The risk I would take is not the same level of risk he would take. And it can bring out massive fear in those around you. For a very long time, when I was younger, I didn’t realise it was fear. I believed that it was someone stopping me in my tracks. You know, trying to put a road block in there… Over 18 years we’ve learned how to communicate about business, and what I would do.

Rather than seeing loved ones’ concerns as obstacles, she learned to communicate with them in a way that helped them understand the journey. For any entrepreneur with a sceptical family or partners, her advice is to involve them in the process, help them see the vision, and be mindful of their perspective.

Bootstrapping vs. raising investment

Holly has always championed bootstrapping – the process of starting a company with little capital. In fact, most entrepreneurs start with a small budget to fund their very first venture.

I actually think bootstrapping is possibly the best place an entrepreneur can be in. Because I think an entrepreneur’s most happiest place is when they’re creatively having to think outside of money. You know, money can really dent an entrepreneur’s… capabilities and skill.

However, there were moments when investment was necessary. When Not on The High Street faced financial struggles, Holly had to raise four rounds of venture capital funding, often sitting across the table from rooms full of investors from prestigious backgrounds.

I’m a dyslexic girl with just a few ‘A’ levels, with an ‘E’ in Business Studies, and I was around a table with 15 Harvard men.

This moment speaks to one of the biggest lessons in entrepreneurship: business owners don’t need degrees from top universities to thrive. Instead, they need a vision, ‘bounce-back’ mindset, and the drive to make things happen.

Why business isn’t just about money

Despite building a business worth millions, Holly remains convinced that money alone doesn’t bring happiness. She recalls how she once found herself living the executive lifestyle, staying in luxury hotels and flying business class. But something felt off.

I realised that I was living this sort of executive life and I was not being the true Holly hurricane. I wasn’t my creative self.

Over time, she shifted her focus towards experiences over wealth, choosing family adventures over luxury holidays and prioritising purpose over profit.
This raises an essential question for aspiring entrepreneurs: What kind of success do you want? Is it financial freedom? An adventurous lifestyle? More time with your family? Your end goal will help dictate the path you take.

Key lessons for entrepreneurs from Holly Tucker’s story

Not on The High Street is now home to 5,000 small businesses, each hand-selected by a team of in-house curators. The business has become a go-to online marketplace for inspiring gifts, but it wouldn’t be what it is now without the journey Holly has been on. Her story unveils some invaluable lessons for budding entrepreneurs:

1. Fear is normal, and taking risks is a must: If you’re afraid of taking the leap, start small. Side hustle, bootstrap and build gradually.

2. You don’t need perfect credentials to succeed: Holly built a business worth millions while battling imposter syndrome and trying to convince male investors to fund her idea.

3. Money doesn’t define success: Many entrepreneurs chase financial success only to find it unfulfilling. Define what success truly means for you and build a business that aligns with that vision.

4. Bring your loved ones along for the ride: Entrepreneurship can be lonely, and not everyone will understand your goal. Instead of seeing doubt as a roadblock, communicate your goals clearly and involve friends and family in your journey.

5. Build from the ground up: Limited resources force you to think outside the box. Money certainly makes things easier, but many successful UK businesses started out with little capital.

Ready to start your own small business?

If you have a great business idea and are starting small, there are many startup finance options to explore. Read our guide on how to fund a startup in the UK to learn more about options such as small business loans, government startup finance, invoice financing, and crowdfunding. Ready to start your venture? Contact the experts here at 1st Formations for advice on choosing a company registration package and more.