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Interview with Ian Isherwood, CEO of DateME Kenya

Gavin Morrice

Written by Gavin Morrice on April 22nd, 2015 21:45

This is the first in a new series of blog posts in which we pick the brains of proven entrepreneurs and interesting figures in the startup world, find out what makes them tick, how they approach their problems, and what advice they can share.

We’re launching the series with an interview with our client Ian Isherwood, CEO of DateME Kenya — Kenya’s first premium, online dating website.

Ian Isherwood / Founder of DateME Kenya

First of all Ian, can you tell me a bit about yourself and your background?

I have a rather unusual background. I’m 4th generation Kenyan on my father’s side and Scottish on my mother’s, allowing me the luxury of being both a Kenyan and British citizen. This comes in very handy when doing business in Africa and Europe. I’m the youngest of 4 boys, I’ve attended 7 different schools, and I’ve lived in 3 different continents.

I have a huge passion for business and I’ve sold all sorts of things throughout my life. The most unusual thing being used women’s underwear — it’s a long story… This was back in my poor student days in Leicester. It was a crazy idea with a friend to make some extra beer money. Let’s just say that opened up my mind to a whole new world and made me think outside the box! — A few years older and a lot wiser, I’m now running Kenya’s first premium dating site.

Your company is DateME Kenya. Can you summarise, in a sentence or two, what DateME Kenya does?

DMK is a members–only site that helps bing people together in a fun and safe online environment; we make it easier and more convenient for busy professionals and expats to meet.

And what is it that makes DateME Kenya stand out from other online dating services?

Apart from being the first premium, members-only site in Kenya, we also are the safest and most private, ranking us as Kenya’s #1 trusted dating website. I believe in quality over quantity and the members appreciate this approach too.

We have several unique features such as DateMe Ideas that allow members to suggest what they want to do on a date; this helps people get offline, where the real connections happen.

We also have a fun and effective algorithm that helps match members through a series of multiple-choice questions. We are the only dating site to approve all new members, updates, and content uploaded to the site manually before it goes live. This is a lot of work, but it helps us keep the site a fun and safe place for our members.

How long has DateME Kenya been in business?

The site was launched in June 2013. This year we celebrate 2 years in business!

What inspired you to want to start your own business, and a dating website!?

I’ve always done things differently; I love a challenge and I find it extremely exciting to do something that has not been done before. I guess that’s the adventurous side in me. When I was a kid I secretly wished I was born in the 15th century and could explore the world like Columbus. So after spending 10 years away from Kenya studying and working, I returned home to look for new opportunities in an emerging market that has so many possibilities.

I spent 6 months traveling around East Africa, reconnecting with my roots, finding my feet, and looking at all sorts of businesses such as goat farming, dried mango production, property, bee-keeping, farming etc. Then, after speaking with a number of friends in Nairobi who complained about it being hard to meet quality singles in such a busy city, a light–bulb went off and I thought: online dating.

I looked into it and there was nothing in Kenya, apart from a few cheap sites full of prostitutes (a big problem in Kenya). When I looked into online dating across the World I saw that it’s hugely successful industry, and worth about 4 billion a year globally. I decided to play cupid. I got the right people on–board and turned a few crazy ideas into a quality dating site that will change how people meet and date in Kenya, and over time, Africa!

As CEO, what does an average work day look like for you?

It’s hard to have an average day in Kenya! Kenya is very unpredictable; every day is different and filled with unexpected twists and turns. One day you might not have any internet; perhaps the power goes off; people cancel meeting at the last minute or simply turn up hours late; the police might decide to stop you for no reason and hold you for hours hoping you might pay a bribe (I never do!); every day has a little adventure and I love it, it makes me feel alive!

But, like most people living in Nairobi, my main aim to any day is to avoid being stuck in traffic. Nairobi has one of the worst traffic problems in the world. So I make sure all meetings are scheduled close to the office or not during rush hour, when a 3km [1.9 miles] trip can take hours.

I’m an early riser and get up at about 6/6:30am (depending how late I worked the night before). I read for 30 minutes, then look at the goals and targets I had written down the night before to remind myself what I need to achieve that day. Every morning I also try to write down 5 new ideas, this helps me become more and more creative.

I’ll try to squeeze in some yoga or a gym workout, shower, breakfast and then focus on my emails and social media. I don’t have a set plan for how I do my work, but usually I focus on what is most urgent. I handle pretty much everything except the IT/software side of things, so it’s a lot of work.

Luckily, living Kenya gives you a great quality of life and having a full-time chef makes it easy to eat healthy, and gives you more time to stay focused on work.

What are some of the challenges you’ve encountered since you founded DateME Kenya?

I won’t lie! Setting up a business in Kenya is not easy; we have had a lot of challenges and hurdles to cross! People forget that online dating has been around in America and Europe for well over 20 years. But most people in Kenya have never used one, let alone set up a profile of any kind apart from Facebook.

So our biggest challenge was, and still is, changing how people see online dating and convincing them that DateME Kenya is a safe site, full of kind, friendly singles — just like them. Kenya has its own unique dating culture. It’s still very much a man’s world , but that’s changing and DateME Kenya is helping change that.

Facebook also threw in a huge challenge when they decided back in December 2013 to ban all dating sites from advertising on their site. I had spent thousands of dollars building up a strong fan–base of over 12,000 on our Facebook page when Facebook suddenly decided to ban all dating sites. This means we cannot boost posts or reach new members! These days when we post something on our Facebook page it only reaches about 50 to 100 people out of 12,500 people.

Some of the smaller everyday challenges are: dealing with power outings, terrible Internet or NO Internet, bad traffic, cancelled meetings, and the general lack of punctuality. I’m rather militant when it comes to time–keeping and punctuality, I guess that’s the British in me.

… and how are you dealing with them?

Changing the way people meet and date is never going to be an easy task. The Kenyan culture is still very male–orientated, but that’s changing. The new generation is better educated, more open to new ideas, and Kenya as a whole has started to embrace the convenience of the internet and all the joys it can bring.

I personally meet up with new members and encourage anyone interested to come to the office for a coffee so that I can talk to them face-to-face and explain to them the benefits of online dating. It’s hard work and time-consuming, but there is nothing better than face-to-face interaction to help establish a trusting relationship.

I’m sure you’ve tried a few different approaches to marketing? What’s been your most successful marketing tool?

We tried a number of advanced marketing techniques that are highly successful in places such as Europe, but they simply did not work for us. The best approached I’ve found is what some might call the “old fashioned way”. Face-to-face talks to clubs and groups such as the Rotary Clubs around Nairobi.

People love to hear and talk about relationships and since this [online dating] is such a new concept for so many people in Kenya, they are fascinated. Putting a face to the company helps establish trust.

What are some of the biggest mistakes you’ve made?

I don’t think we have actually made any big mistakes, but we have made many mistakes. But that’s to be expected when something like this has never been done before in Kenya.

Perhaps the most expensive mistake was hiring a Google Ads expert and paying a lot for pay–per–click ads. We found that although we got a lot of traffic, we were not getting nearly enough conversions to justify the amount of money we were spending.

The fact that we are a member’s only site and target a niche market means we have no reason to go for the mass market and so we cut down on pay-per-click and focused more on other areas.

What has been your most satisfying moment at DateME Kenya so far?

Funny you should ask this… Just the other day I had some amazing news from one of our members. I received a lovely email from a female member explaining that she had met the man of her dreams on DateME Kenya. She explained that she met him last year and after dating for some time, they got married! This was our first marriage (that we know of) and a huge milestone for me and everyone evolved with DateME Kenya.

Knowing that all our hard work has helped bring two people together in marriage is a very special feeling. We know of a lot more members who are happily dating too, and more marriages are definitely on the cards soon.

I know ‘success’ means something different for everyone. How do you, personally, define success?

I measure success with happiness. If a person is genuinely happy with themselves and the life they live, then this is true success! We live in a world that is so focused on chasing “success”. We are told that if you are rich you are successful, or if you are powerful you are successful. When, in reality, everyone really just wants to be happy. So for the lucky few who find true happiness in life, these are the successful people in my eyes.

What motivates you to get out of bed in the morning?

Right now I’m motivated by work, health, and chasing my dreams. I recently read a great book called “Life In Half A Second” by Matthew Michalewicz [link at the bottom]. In it he talks about how we should focus on how much time we have left in this world, and to stop focusing on how long you’ve been alive. This really gets you thinking. He gives you a formula to calculate how many days you have left (on average of course) and this is a slight twist, making you appreciate each day that little bit more.

What is your favourite aspect of running your own startup?

All the women — Haha! Actually that’s a mini nightmare… the site has too many women and we are trying to focus on attracting more men to the site.

The best part of running your own start-up is being your own boss. I know this is what everyone says, but it’s true. You get to make the decisions, but this also means you have to accept all the failures and mistakes too. But knowing I’m in charge of my future and my destination is a great feeling!

What three pieces of advice would you give to anyone planning to launch their own startup like DateME Kenya?

Understand your market, research the competition and be prepared for years of hard work and a rollercoaster of emotions!

Getting involved in a start-up like DMK is a great learning curve for anyone interested in the world of tech and emerging markets. They need to be willing to work hard and for long hours, sometimes with little reward, and be prepared to sacrifice what they would like to do for what they have to do. The competition is always chasing you and you always need to think of staying one step ahead of the rest. No idea is too crazy and writing them all down really down helps.

If you could time-travel back to day one, when you first started DateME Kenya, and have 15 minutes to chat with your former self, what would you tell yourself?

I can get a lot done in 15 minutes… I’d probably start by telling my former self a few football scores, what stocks to invest in, and maybe the lottery jackpot numbers. Then I’d tell myself to make the most of opportunities that comes your way and to take more risks.

Any parting thoughts for readers?

Quotes are always a great way to part, so here is one I recently read and loved! “No matter how educated, talented, rich, or cool you believe you are, how you treat people ultimately tells all. Integrity is everything.”


Thank you, Ian, for taking the time to answer my questions, and best of luck for the future

Here’s the link to Life in half a second. If you’d like to read more about DateME Kenya, click here to visit the site.


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