By Kimberley Taylor
There was a pivotal moment in my entrepreneurial journey when the tables turned, and I found myself transitioning from the person seeking guidance to the one being sought out for advice, insights, and expertise. Suddenly, people were reaching out to me for guidance on building their own businesses, eager to hear my pitch, or seeking introductions to valuable connections.
It’s a surreal experience, to say the least. And while I’m humbled by the recognition, I’m also acutely aware that I’m far from having all the answers. In fact, I don’t think anyone can truly know it all, nor do I want to. The beauty of entrepreneurship lies in its complexity, its ever-changing landscape, and the constant need for innovation and adaptation. With that in mind, I’d like to share eight key lessons I’ve learned throughout my journey building Loop – lessons that have shaped me, challenged me, and helped me grow both personally and professionally.
Assumption error
Too often we assume rather than ask. We assume somebody else is going to solve the problem, or that the solution already exists. But everybody else is assuming the same, leaving plenty of room for solutions and opportunities. This phenomenon is often referred to as “pluralistic ignorance,” where everyone assumes others know something they don’t, resulting in collective inaction.
Curiosity is key to breaking this cycle. Be curious about the problem, the process, the people, and the possibilities. Ask questions, seek feedback, and challenge your own assumptions. Test your assumptions constantly, both about how the world could look and what you believe it should look like. By doing so, you’ll uncover new insights, identify potential blind spots, and create opportunities for innovation and growth.
In my experience, assumptions can be particularly damaging when they’re based on limited information or biases. For instance, assuming a particular market trend will continue without verifying the data can lead to misguided decisions. By staying curious and testing assumptions, you can avoid these pitfalls and make more informed decisions.
Try on new things
As an entrepreneur, I’ve learned to give myself permission to try on new things – almost like stepping into a character. When I’m inspired by someone’s confidence, leadership style, or approach to problem-solving, I allow myself to “try it on” for myself. It’s about experimenting with different personas, styles, and approaches to see what works best for me and my business. By doing so, I’m able to tap into new strengths, build confidence, and develop a more adaptable mindset.
This process of trying on new things is essential for entrepreneurs, who must be willing to evolve and adapt constantly. It’s not about being a chameleon or pretending to be someone you’re not; it’s about being open to new experiences, learning from others, and finding what works best for you and your business. Whether it’s trying a new communication style, taking on a new role, or exploring a new market, the ability to try on new things can help you stay agile, innovative, and ahead of the curve.
By embracing this mindset, I’ve been able to:
- Develop new skills and expertise
- Build stronger relationships with colleagues, partners, and customers
- Stay adaptable in a rapidly changing business environment
- Discover new opportunities and approaches that I may not have considered otherwise
Build in boiler rooms, not boardrooms
In business you need to get your hands dirty. We can’t only theoretically conceptualise solutions to business problems in boardrooms. We need to get into the boiler room to understand what the actual problem is we’re trying to solve.
When I first started the business, I took every opportunity to learn from the person whose problem I was trying to solve. This looked like getting into the delivery vehicle with the driver, going on their route, asking questions about how they approach their day, why they do it a certain way, what they find challenging, and it was immensely useful in understanding the actual problem we’re looking to solve, rather than a theoretical assumption.
I also believe we need to feel the problem. When we have empathy with the person whose business challenge we’re trying to solve, we’re better able to understand the nuances and complexity and thus more likely to solve in an effective and relevant way.
So, what?
In my experience, entrepreneurs are innately curious. We’ve only got to look at children to know that’s true for all of us – they’re naturally inquisitive, always asking questions, and seeking to learn. As entrepreneurs, we need to tap into that same curiosity and ask questions that challenge our assumptions and push us beyond our comfort zones. One of the most powerful questions we can ask is “so what?”
“So what?” is a question that prompts us to think further, to think beyond the obvious, and to explore the implications of our ideas and actions. It’s a question that encourages us to dig deeper, to seek connections, and to consider the potential consequences of our decisions. By asking “so what?” repeatedly, we can uncover new insights, identify potential opportunities, and develop a more nuanced understanding of our business and the world around us.
For example, when analysing customer feedback, asking “so what?” can help us identify patterns and areas for improvement that might not be immediately apparent. When evaluating market trends, asking “so what?” can help us understand the potential implications for our business and identify opportunities for growth.
Be the HGB
HGB is for “hot girl or guy at the bar”. Hear me out on this one. It’s about attracting, not hard selling. In business, that means ensuring your product can sell itself (attracting) because the features and functionality are appealing to the potential customer as it solves a specific business problem. When your product is the hot girl or guy at the bar, it doesn’t shout “look at me, buy me a drink” but rather it carries itself in a way that others find interesting and appealing.
Think of it like this: when you’re at a bar and you see someone who catches your eye, you don’t need to be sold on them. You’re drawn to them because of their confidence, charisma, and authenticity. That’s what we want our products to be – the kind of thing that people are naturally drawn to because of its value, quality, and relevance.
To achieve this, we need to focus on building products that are not just visually appealing but also substantively valuable. Everything that looks good must be supported by the substance on the inside. This means investing in user experience, customer support, and continuous improvement to ensure that our products meet the needs and expectations of our customers.
Make yourself the villain
When things don’t work out the way we’d like, it’s easy to play the blame game. We point fingers at others, circumstances, or fate, hoping to shift the responsibility away from ourselves. But this approach rarely leads to growth or resolution. Instead, I’ve found it helpful to imagine the situation as a story where I’m the villain. By taking ownership of my part in the situation, I can regain control and find the lesson in it.
This mindset shift allows me to focus on what I can control – my own actions and reactions. Rather than getting bogged down in anger or resentment towards others, I can channel my energy into learning and improvement. By acknowledging my role in the situation, I can identify areas for growth and develop strategies to avoid similar challenges in the future.
The sooner we recognise and accept our role in an undesirable situation, the faster we can learn from it and move on. Blame limits our potential, while bravery creates an opportunity to learn and grow.
One small step
The difference between having an idea and a business is action. Action is what sets us apart – you are either the person that talks about being fit, or you’re the person who gets up consistently to go for a run. You’re either the person who talks about the big idea, or the one that builds the deck or makes the call.
At the beginning of my business journey, when everything was about selling the product, I had a big piece of paper, and I drew 100 blocks on it. Each block represented somebody I would approach with my product – through connections or cold calling – and I would colour every block either red or green. Red if I was unsuccessful and green if the person at least listened to my story (or pretended to). There came a point where the green blocks outnumbered the red blocks, but only because I persisted, and then some.
Big things are overwhelming so start small. I believe that courage builds confidence and the way to be courageous is simply to find the next small thing to do – make a list of potential clients, write a script of what to say to these clients, whatever small thing you can manage but keep moving forward because that’s what momentum is.
The struggle is real
Not only is the struggle real, it is also very important. People will make assumptions about you or try to put you in a box. One I hear often is “your dad must be rich” (that is not the case). I am the product of my past – this is true for all of us – and because of a chaotic home life in my early years, I learned that life is not fair, but we must find purpose in it anyway.
As a child I loved the story of Matilda by Roald Dahl. The young character’s ability to think herself out of an undesirable situation is something that I recognised as a superpower at age eight. Today, my version of Matilda’s abilities is to write down what I want the end story to be. I ask myself what, when I eventually look back on a particular period or project or challenge, what is it that I want it to look like, ideally. Call it reverse-engineering but I have found it to be a powerful way of taking ownership of a situation. And recognise the struggle in that and do it anyway.
There is purpose on the other side of the hard things we go through. This belief has really helped me build resilience through the many challenges I’ve faced in life and business
As countless entrepreneurs have said before me, and will no doubt continue to say, business is a combination of luck and timing. But you still need to work hard, and smart, and do all the things.
Together with the working and the doing, lean into what inspires you and the eventual outcome is certain to be beyond what you could imagine.
Kimberley Taylor is the Founder & CEO of Loop
