Ian Isherwood on the Business of Love

Profile photo cropped.jpg

Article by: Damaris Agweyu

Publication date:

We go through life not wanting to hurt people’s expectations of us because we think they are not strong enough to handle the truth

Be clear about who you are from the very beginning. If you want something from a relationship, don’t wait for 2 years and then start complaining about how you never get what you want.

Ian Isherwood founded DateMe Kenya with a clear goal of offering a private, secure and safe platform for relationship-minded singles. Today, his company has grown to become the largest premium online dating platform in Kenya with close to 75,000 registered users since its launch in 2013.

The 32-year-old entrepreneur who describes himself as a ‘work in progress’ shares some of the wisdom he has picked up along the way with Damaris Agweyu.


After 5 years of running Date Me Kenya, what have you learnt about love?

The philosopher Alain De Botton talks about love being a skill, and I fully agree. We all love to think that we will meet someone and there will be an instant connection. Where they know what’s on your mind and you know what’s on their mind- the assumption is, ‘if you really love me you should know my needs’ but that’s not true. You can’t meet someone and instantly know what they want. You constantly need to help each other understand each other, to compromise, to take and to give feedback constructively. It’s continuous learning. Not many people are willing to put the required effort into love.  It’s important that you are frank and truthful and to do it from the beginning in order to open that safe space for growth.

But everyone pretends or rather, shows their best selves in the beginning, are you saying they shouldn’t?

It’s inevitable to show the best version of yourself when you first meet someone. However, after a certain amount of time the real you will come out. What I am saying is, be clear about who you are from the very beginning. If you want something from a relationship, don’t wait for 2 years and then start complaining about how you never get what you want.

On DateMe Kenya, there are people who put in a lot of effort to upload their best photos and then there are others who are so true, they will put a photo without makeup as if to say, this is who I really am, this is the face you will wake up to every morning; they may add another glamorous photo to show they are able to make an effort when required but they are not ashamed to put a real photo and show their true selves, I admire that.

And if, eventually, you find that you are just not compatible with someone, is there a right way to break up?

I think so. It’s about being brave. If it doesn’t work out, it doesn’t work out. I wasted many years of my life in a wrong relationship but it’s because I was comfortable. You owe it to yourself, to be honest about the situation: who you are and what you want.

Working on yourself is the most important thing you can do in life, and this means auditing your life regularly - who are your friends? what are your beliefs? what are your plans? Then you take control of your life and if someone comes in with different ideas, you will be so solid that you can immediately give an answer as to where you stand, instead of wasting a year, 2 years or a lifetime.

What motivated you to start a dating website?

Having lost my father when I was 2 years old and being raised by a single mum, who by the way did a great job raising 4 boys on her own, I realized how important it is for children to have a father figure. I also saw how to this day, 30 years later, my mum is still in love with my late dad and understood and believed in the idea of finding and having true love in one’s life.

And so when I was older, after having travelled around the world, I had seen the success of online dating so I thought to introduce the concept to the Kenyan market. I was naïve enough to think, OK great, I’m going to bring a European concept, tweak it to the Kenyan culture and it will be a huge success. But I didn’t know anything. It hadn’t been done here before and I hadn’t studied or learned from anyone else.

Yours was the first in Kenya?

There were a few small sites that were attracting a totally different audience. They were focusing a lot on sex and casual relationships and I didn’t want to go down that road.

When I launched, I became very private and niche market. I was going for the top 5% in Kenya which is great because I wanted to build a strong brand. I believe I have done that but it’s also divided because not many people can afford 4,000 shillings a month. I honestly thought Kenya might have been a bigger market, but when it comes to business, Kenya as a whole is hard. Unless you’re mass market and selling sugar, everyone needs sugar.

Everyone needs love as well...

But with my concept, Kenya is still very far behind when it comes to accepting that you can meet someone online. There is only a handful of people who are willing to admit that they found a life partner online. People will be like, "oh you needed an online dating service to meet someone". There’s still that negativity but it's changing slowly thanks to sites like Tinder.

Is Tinder giving you a run for your money?

Not really. It has actually helped us because it’s brought a mainstream acceptance to online dating and some people use it and don’t want a hookup site.

So your business model is working?

Slowly yes. Only recently I’ve seen reviews on DateMe Kenya where people are saying they met their spouse there and that’s encouraging, but I want to have thousands. I’d love to help everybody and that’s the difficult part.

In Kenya, we have this prevalent sugar daddy and sugar mummy culture which makes it hard. Of course, there are sugar daddies and mummies all over the world but in Kenya, it’s like part of the culture. On a daily basis, I get people calling and asking for them but now I can be a bit cheeky.  What I do is I have a bit of fun with it. I’ve got the number for the Kenya Sugar Board and I’ve got a template which I use to tell them they can find all the sugar mummies and daddies there (laughs).

The problem is that big?

When I set up Date Me Kenya, I was ignorant of just how big it is but yes, it’s a huge problem. Although now I understand why some people need sugar mummies and sugar daddies.  When you have nothing and you know sex can buy you something, I understand why you might do that; no one wants to sell their body but if you find a rich man who can give you a nice apartment in exchange… it’s nice to have those things. We all crave them so it would be wrong of me to judge when I’ve not been in that situation. I still believe it’s wrong and I don’t accept it so sometimes I try to give the people who are looking for this some coaching and advice. I ask them what else they have tried to do, whether its work or studying and then I hear the stories and realise some people just can’t get the opportunities. Some of us are born into a life of privilege and for some people, it’s very hard.

So members are thoroughly vetted?

Yes. We’re committed to quality, not quantity. We don’t allow people who just want to sell themselves to join DateMe Kenya but again this is a constant battle. I’ve asked myself, should I open up the platform? It’s hard to make a judgement as to whether someone is doing it out of necessity or if they’ve just made a lifestyle out of it. It’s opened my eyes to a lot. Yes, I was born in Kenya and grew up here till I was 13. So I always relate to myself as Kenyan but I grew up on a different side of Kenya. Although I grew up in Mombasa where there is lots of prostitution, I never understood the people making these choices. Now as I get older and understand more about life and myself I am beginning to understand where they are coming from.

How many users have you had on your site?

Since launching, we have had over 74,500 users register. But we only approve about 6% of those for membership.

More women than men I presume?

We have more male registrations but more female active members. What I mean is everyone can create an account but we only approve those who become members. Women know what they want but most men are still very casual.

Explain that last sentence.

Men aren’t sure. They may say they are ready to get married but not ready to commit to one woman. They’ll be thinking, all my friends are getting married so I should do it too. The women are detailed in what they want but having said that, thankfully, more and more men are seeing the value so we are starting to get some good quality men who are really strict about what they’re looking for.

Can you know what you are looking for in a relationship if you haven’t been in one?

Everyone is different. Some people are naturally able to adapt to things that are good for them, but others need to go through things to know what they don’t want. Personally, I like to live through the experience- but I also learn to take advice from older people I admire.

You have to be brave enough to go for what you want or to get out of what you don’t want. Take time to contemplate advice from mentors and have that at the back of your mind. So when red flags come up, get out. Don’t be foolish enough to think you have to make a mistake to learn. It’s like starting a company, you may have to start 2 or 3 companies before you find your footing.

DateMe Kenya is not your first business

No. I started my first business when I was 18.

So you’ve never been employed?

I’ve never had a boss but I’ve always looked for positive influencers for my life. 

Influencers did you say?

Not in the sense that we know them to be today. Now there are influencers all over the world and what exactly are they influencing? Well, it's usually what you can’t have in life because they are showing off new cars or a lifestyle you’ll never achieve. If they influenced with hope and changed people’s lives not by showing off big fancy houses, which would be great.

When I talk about influencers in my life, I mean having a good mentor or advisor, someone who’s walked the road I’m walking. Some of my friends were in their 40s and 50s when I was in my teens. I was watching them and seeing them live life rather than take it for granted.

Are you a better partner in your relationship from having run Date Me Kenya?

I have learnt a lot about love and would, of course, say yes, my partner may disagree (laughs). One thing I know is I’m not here to waste time or play games. I have constant conversations with my partner which revolve around our relationship. We are constantly asking each other what we both want in the relationship and we make it a point to work on meeting each other’s’ needs.

When you have a sound plan and structure for your life, then you have stability which equates to self-confidence, from there you can decide where you want to be and who you want to be with.

Ian Isherwood

Can you share some of the knowledge you have gained from running a business?

Wow, I’ve learned so much over the years. Some people start companies thinking they’ll have a lot more time for themselves since they are running their own show, it’s the total opposite! It’s naïve but you have to do it to experience it. I’ve never had a holiday where I’m not working. I’m constantly checking up on things, whereas if I had a 9 to 5 I’d have more free time. The journey may be exciting but chances of becoming a billionaire are very slim- unless you have amazing contacts- contacts are contracts in Kenya.  I started DateMe Kenya because I saw an opportunity. I love business. I was naïve in thinking I was going to make so many happy couples, my motives were right but then I realized how complicated people are.

I also didn’t realize that my passions would change over time. When you are dealing with all these things like people selling themselves for love; there is a constant battle about the direction you are going to take.

So it’s important to do your research, but be very thorough, have a business plan, get people to read it, get some people who will criticize it, be realistic about how much money you can make and it will take time. DateMe Kenya has been running for 5 years now and we are still not sure about what direction we want to take. Reach out to people who know your business model and take their advice. Get as much information as possible, don’t be naïve to think you know everything because it’s very rare- and just start.

Sometimes you may start with a business idea and then realise you might have to change it if you get an investor who might want go down a different avenue. This might jeopardize your own personal beliefs but then in business, you do have to sell yourself one way or another- and that’s OK, as long as it’s safe.

What advice would you give to anyone looking for that special one? Perhaps on DateMe Kenya?

First, take the time to really know who you are. A strong foundation starts with you. When you have a sound plan and structure for your life, then you have stability which equates to self-confidence, from there you can decide where you want to be and who you want to be with. Many people don’t know who they are and what they can offer. Don’t be afraid to be alone and sit with your emotions. Allow time to heal past hurts and don’t just jump on a dating site to get the ego boost. Sometimes you need to be harsh on yourself. I constantly ask the 5 or 10 people closest to me, "what are my strengths? Weaknesses? What do I do that annoys you?" Sometimes we are blind to our own weaknesses.

You’ve talked a lot about self-growth. What else are you currently doing to improve yourself?

I’ve taken up boxing which I now do 3 to 4 times a week. It teaches me discipline and I want a healthier life. I’ve also signed onto a marathon in preparation for a walk I’m planning to do from Nairobi to Mombasa. I’ve also semi-committed to an iron man challenge. I’ve made a deal with a friend of mine that if he joins me for the walk, I’ll do the iron man with him. The reason I have set these crazy goals is to show myself that I can overcome them. Yes, it’s painful but it’s a personal battle and if I can overcome these battles then what can’t I do?

You’re really going to walk from Mombasa to Nairobi?

Yes. I have vocalized it and have committed to do it with someone and this is a very important part of setting goals for me because then I have to follow through. Being true to my word is very important for me.

For more wisdom and insights from Ian Isherwood, get your copy of Different Paths, One Journey HERE.


* indicates required