From blunders to bliss: A matchmaker’s journey

Ian Isherwood, founder and CEO of Dateme Kenya Ltd.

Ian Isherwood is the CEO and founder of the exclusive dating site, DateMe Kenya.

He spoke to Hustle about the mistakes he’s made in the process of building his business, and lessons that have made him one of the country’s top matchmakers and a better entrepreneur.

What costly mistake did you make while starting out?

In the early stages, I made many mistakes. I was 18 years old when I started my first business, back in Leicester, England.

When you’re that young, you don’t have any real business experience or networks to help you. I would often have to figure things out day by day. It was hard, but I adapted quickly.

Like many early-stage entrepreneurs, the biggest mistake we make is that we don’t dedicate enough time to planning and thinking things through. I fell into this trap, but I learned quickly. As they say, ‘failing to plan is planning to fail!’ But when you’re young, that stuff’s boring; you want the action.

What lessons did you learn from your failures?

All my failures give me a chance to stop, recap and then improve. We’re human, we all make mistakes.

We must think like children. When a child first starts to walk, do they give up after the first time they fall down? No, they keep trying. When a child starts to ride a bike and they fall down, do they give up? No, they keep trying.

So why is it that when we’re supposedly ‘older, wiser, and smarter’ we forget these simple, primary and instinctive rules? Just keep trying. Never give up!

What would you describe as your biggest failure?

In all honesty, I don’t know. I have made many big mistakes that have cost me financially, but I don’t consider them failures. I’m a very positive person, so if anything, I would say my biggest failure is perhaps working too hard and not spending more time with family and friends.

How do you manage your money?

I create daily, weekly or monthly accounts and stick to them. In the early stages, I was a teenager and care-free, and would simply focus on making sure I made more than I spent.

It worked, but it was risky and I had no real control or plan. However, as with most things in life, the older you get the wiser you become. Now, I keep it simple and clear.

What’s your philosophy on money?

Look after your pennies and the pounds will look after themselves. In other words, if you concentrate on saving small amounts of money, you’ll soon amass a large amount.

What’s the most impactful lesson you learned in the first few years of business?

The importance of a strong and influential network.

The bigger, deeper and stronger your network is, the faster you and your business will grow. In my first few years, I was doing everything alone. I worked every minute of every day for years and had to figure out all my problems alone.

But as my network grew, things became easier. I could reach out to friends in the industry I was in for advice, help or anything else, and in return, I could do the same for them.

What book would you recommend every entrepreneur read?

Influence: The Psychology of Persuasion by Robert Cialdini is hands down one of the best books I’ve read – for business anyway. Every entrepreneur should read it. In fact, once you’ve read, I bet you’ll read it again. There are so many treasures hidden in those words that each time you pick it up, you’ll have a new ‘aha’ moment.

What’s the most offbeat advice you’ve ever followed?

In my early teens, I moved from Kenya to the UK, and it felt like a different world. I had never been before; Africa was all I knew. I spent a lot of time just observing how different the people were and how they acted.

They lived in a throwaway culture, whereas in Kenya, we use everything until it’s on its very last legs – and then we find a way to use it some more. We’re amazing people that way.

My grandfather once told me that ‘one man’s rubbish is another man’s treasure’, which stuck with me, and years later, I would quite literally sell rubbish on eBay.

I worked in a cocktail bar while studying in Leicester, and would take home the empty bottles and metal tins the drinks came in. We were throwing them in the bin. I sold these bottles and tins to collectors in the US and across Europe. It felt like free money and good money as well. It opened my mind.

What sectors are trending right now?

Globally, I’ve been keeping a keen eye on key industrial commodities. They’ve been on the rise, and I think they will continue to do well in 2019.

What personality was key to your success?

Success means different things to everyone. To me, my secret is my emotional intelligence.

I’ve spent a lot of time working on the five key traits, which are: self-awareness, self-regulation, motivation, empathy and social skills.