Staying on top: The three big challenges I’ve encountered as a young entrepreneur

Stuart Maitland
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Jack Ma is renowned for singing karaoke with employees and holding company retreats for 15,000 co-workers (Source: Getty)

Life as a young entrepreneur is a thrilling ride. You have the opportunity to rub shoulders with older, inspirational entrepreneurs and learn from their experiences. Interesting projects land on your doorstep. And when done correctly, it can financially set you and your family up for life.

Yet as with everything, there are problem areas. Many entrepreneurs, for example, worry that access to finance poses the biggest threat to success. Others struggle to keep up with the latest innovations. As fellow young entrepreneur Tristan Harris, founder of Apture, once said: “the landscape no longer changes every two, three, four years like it did in 2002. If you’re not quick on your toes, you will miss opportunities”. But I worry more about three different issues: obtaining respect from older peers; time management; and cashflow. Here’s how I overcome them.


Recent research has found a significant shift in Generations Y and X moving into management roles in the past few years. While this brings with it many perks, older generations can find it extremely difficult to take instruction from younger managers. Set in their ways, with a fixed mindset and sometimes unwilling to cooperate, older members of staff can make the life of a young entrepreneur even tougher – but there are ways to combat it.
First, adopt a different leadership style. No one likes being patronised, so be sympathetic, listen and stay firm. Take the time to talk to problematic team members. Your employees know you’re in charge: they don’t need constant reminding. In fact, some of the best managers that I’ve encountered are comfortable with who they are – they don’t feel the need to assert their authority at every opportunity.
A good example is Alibaba founder Jack Ma. The inspirational leader is renowned for singing karaoke with employees, holding company retreats for 15,000 co-workers (focused on fun rather than work) and dressing in whimsical outfits when addressing his senior team. You can win your employees’ respect without being bossy. And showing respect in return will also increase their productivity.


Business owners of all ages are constantly working against the clock. My daily to-do list is inexhaustible, and it can sometimes feel overwhelming. It’s why many high-flyers feel burnt out: they’re failing to manage their time effectively.
The solution? Give yourself a break. A 2014 Hiscox poll may have found that the average UK entrepreneur takes 21 holiday days per year, but for many of us, time off feels like an alien concept. But your business is not going to crumble if you have a breather.
Moreover, one of the most important skills every entrepreneur needs is the ability to delegate. Decide what is important, make key decisions, and cut out the fluff. You don’t need to respond to every email, and you’re not risking mutiny if you don’t attend every meeting. Ask someone on your team to feed back to you on key issues, try to switch of in the evenings, and learn to relax at the weekends.


We entrepreneurs have the opportunity to earn a lot. But we need to forget about fast cars and the finer things in life: our wallet is our company’s lifeblood. Stringent financial controls are important both in business and your personal life. If you have an accountant, make sure that they manage your business and personal finances – otherwise, you risk finding “little reasons” to put your hand in the company pot for personal pleasures.
Be strong, be disciplined, and ensure that your pension and future investments are being looked after. I’m still only 21, but I have worked hard in the years I’ve had so far, investing a chunk of my earnings in property.
Over time, I have seen budding young entrepreneurs – who started on the same path as me – fall by the wayside. The stress and lack of discipline became too much to handle. These simple steps could ensure you avoid the same key pitfalls.
Stuart Maitland is the founder of Stuart Maitland Holdings, which includes a property company, a travel accessories company and a chauffeur company. He is also chairman for Young Enterprise, Central North London.

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