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Fail Early; Fail Often & Fail Cheap
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DateFriday, May 27, 2011
AuthorFiona Canning

Fail Early, Fail Often & Fail Cheap

Entrepreneur and CEO at Comparison Website, Caelen King, Talks to About His Early Life's Caelen KingCaelen King, entrepreneur and CEO at, a successful comparison website for worldwide medical and cosmetic services, talks to about his early life, what brought him to where he is and his advice to succeed as an entrepreneur in today's' climate.



Are you from Dublin?

No. I was actually born in the UK. My mum is American and my dad is from Leitrim.  My parents moved to the Middle East when I was five years old and I came back to Ireland when I was 13. Fundamentally Dublin is my home.



Were your parents involved in anything entrepreneurial?

Yeah, I suppose so. My father set up dental practices in various different places like in Bermuda, the Middle East and the UK.



So it wasn't from the wind you took it then?

I couldn't tell you if that had an impact or not. I suppose it's crazy to think that it didn't have an impact, but it certainly didn't have an impact consciously. My mum US educated French teacher and she taught French in schools in Ireland, and when we moved to the Middle East it was nothing but desert and my mum was approached by a Pakistani business man who asked her to set up the first English speaking Pakistani school and she grew that from 20 students to over 700 students in seven years.



Can you pin-point anything from the age of 13 that made you think, ‘I want to start something?'

I ran a sweet shop at 13! It was horribly unsuccessful! It was just within the school. I think in school when I look back on it, I didn't have a clue what I wanted to do. I hadn't a notion. To be honest I was lost in this sea and any kind of influence could have moved me left or right. In no way would I say that you're born with entrepreneurialism. I almost hate the word entrepreneur; it has connotations of something noble almost.


From the age of around 22, I definitely knew, I wouldn't say start-up a company, but I definitely knew that I didn't want to swim in the same direction as everyone else. I wanted to rebel and go in a different direction.



Did you kind of want to be your own boss in a way?

Yeah. I'm older now but certainly at that age you swim very differently and now setting up a company and running a business you're just running slightly different to everyone else largely still swimming in the same direction.




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You mentioned being 22, was it around then that you got first big break?

No, in fact, I was involved in Desktop publishing, disastrous affairs and things that went horribly wrong because I didn't have a clue what I was doing. J

It was just failure after failure to tell you the truth! I eventually decided that I needed to learn something and not just attempt something. I started working for Cara Data Processing and then, when I was around 25 or 26 years old, I joined Baltimore Technologies which was fantastic. The company just exploded and the opportunities I got there were quite unlike the opportunities I would have got anywhere else.


When I joined the company it had about 20 employees and then 3 years later it had 1,400 and a 9 billion valuation; it was worth more than all the Irish banks put together, you know! We were listed on Nasdaq. When a company expands like that, your opportunities expand with it.


I was there for around five or six years, almost until the end when I took off to go travelling around the world for a year.



Why did you decide to travel?

Travel has always been in my blood. In fact, I'll do it again. I've kids now so we'll probably do it in six years time when they're older.



Tell us about your education?

I enrolled in university; I didn't really engage, in fact, I'd no interest whatsoever. But don't ask me what I was interested in; I didn't have a clue.


I certainly did not have any interest in structured formal learning. In fact I rebelled against it.


I enrolled in engineering and blagged my way through the first year exams and then discovered I couldn't blag my way through the second year, so I dropped out and went to the States for a while just doing odds and ends and then eventually decided to start doing my own thing. They all failed until I got more of a structured approach.



Were the things you failed in relevant to the entrepreneur?

Yeah, they were the typical types of things that someone with a ‘computer head' would try to do. Like advertising copy and desktop publishing for example. This was all when I was about 22 or 23.



Do you regret that? Do you regret failure?

Not at all.



Would you feel it made you more focused in getting into what you wanted to get in to?

I don't think you can analyse it. It is what it is. I had fun during those years. I think you should only regret the things that you wanted to do but didn't.


Was it a regular interview that got you into Cara?

Yes. They were providing all of the IT services into Allied Irish Bank. All my computer skills had been gathered hap-hazardly. There was no structure; it wasn't formal in any way. I went in at a junior position, literally wiring computers on to desks.


After about six months, I was promoted to Project Manager, creating secure lines for laptops etc. I then had enough security experience to get into Baltimore who were a security based company. This was at a time when there wasn't a wealth of security expertise in the country, so even though I only had six months experience, it was six months more than anyone else! And this was when my career really took off.



What position did you have here?

I started off in professional services which is effectively going out to client sites, and then I went into technical sales, and then into product marketing for the main product line. It had close on 100million in annual revenue, so it was fairly huge.


You also worked for NewBay?

Yes, I worked for NewBay for four years. I got a call from Paddy Houlihan when I was away travelling. He wanted me to get back to Ireland to work for his new start-up. I told him I would when I was ready to come back. I was rolling out to social media applications, the likes of T-Mobile and O2; it was all huge scale stuff. Newbay is doing very well and is a very good company, but I always recognised that I wanted to set up my own business. I always knew that from years and years back.


Very logically I was trying to gather all of the necessary skills that I'd need. I did my best to get exposure to sales, finance, marketing, development. I did this consciously. I was always conscious of what I was doing.



What would you say are the most important attributes for an entrepreneur to have?

A lot of people talk about ideas being important, and having a good idea. In my view they're not important at all; ideas are free and plentiful. There's no shortage of ideas. I've a tough time characterising. I see people all the time who run successful businesses who display such radically different traits. It's tough to say there's anything in particular that makes someone a good entrepreneur. Execution is so important, and people who like to get things done.

Think about what you enjoy doing first; some people enjoy communicating, creating, researching and these are all in media, computers, music, it could be in anything but they exist in everything. You've got to enjoy getting things done, be satisfied about what you do and be motivated. You have to feel chuffed enough with something to be driven on to the next thing and be passionate about it.



Would you say seeking feedback is important?

I wouldn't have sought feedback. You generally know yourself if a job's done well, like a brickie looking at a wall and the self satisfaction that comes with that as well.


There are two sides to most entrepreneurialism in terms of personality traits; the drive for success and the fear of object failure. If ever you are replaced in a role, everyone has two fears; one that they'll mess everything up or else that they'll do a better job than you. This is daily.


There have been terrible days in things in every company, not just in leadership roles. I remember in Baltimore, I messed up on a Microsoft press story which had taken us a year to build and we destroyed in less than 20 minutes! These kinds of set-backs are normal, but they'll drive you on to succeed as well.


Take pleasure out of a job well done and the awareness of not wanting to let people down around you drives you too.



You have Ray Nolan on board with you; can you tell me a little bit about that?

He came onboard from the start, in 2007. I had met him once before, he was giving a talk at a conference and I was chatting to him for five short minutes. It was primarily through a contact, a friend put me in contact with him and Ray was good enough to give me ten minutes over a coffee and I ran the idea by him and it didn't seem stupid which was great!


You can't tell if an idea is great until you set about it, but you can tell immediately if it's stupid. You can't say it's a good idea until you start trying to do it, you know. It was clear at the time that my idea wasn't stupid and I had enough experience at the time that I clearly wasn't going to fritter the money away.


So he backed us financially at this time and subsequently we asked him to chair. He's quite actively involved with us and he's fantastic to have onboard.


Everyone has crazy ideas you know and you have to be passionate about those crazy ideas otherwise you'll never act on anything. To have someone with decades of experience pick up a phone and say this is great or pour cold water on it, was great to have that.



Would being passionate be a trait for an entrepreneur then?

Yeah. Passion is a weird word. You need to be driven; you need to get excited. You need to be enthusiastic. Passion implies blindness. You can't be blind. If your idea isn't working, it isn't working. You don't need passion per say, but you need enthusiasm. You can't be blind to hard facts. If you're not enthusiastic you won't do it, and if you're not enthusiastic you won't get anyone else enthusiastic



How many staff do you have working here at WhatClinic now?

There's ten including myself and the first member of staff was instant. We formed back in 2007, in the middle of boom years. It was different back in 2007. We raised half a million before we even started. It wasn't difficult to raise money then, but also, talent was hard to find because all the engineers had mortgages up to their eyes and didn't want to risk on a start-up.



How would you go about setting up today?

I'd need to be younger! I'd need to be able to live on less money. I've 3 kids; I need to pay myself a salary.


Honestly though, first of all, things can be done cheaper today. Building a product is cheaper and quicker. Everything can be in your cloud now and all you need is a laptop per person. There's no capital expenditure at all. The infrastructures on which you can build can give you such a leg up. You can get an app up there after two months of hard code. I'm not saying that will be your product but you can at least be testing your assumptions. Maybe it's the tech guy who's the right first employee for a project set-up, rather than a business head like me.


The deck is stacked incredibly high against young people to generate capital. If you don't have the experience or have no product to show, no track record or no money yourself, how on earth can they trust you to raise funds for you? They need something to bank on.



Are contacts a necessity?

Incredibly so. They are a necessity I think. You don't have to know them directly but if a potential investor can't ask their social network about you and get some sort of answers, then it becomes very difficult. People generally don't mind taking a risk, but nobody wants to be made a fool of.


You have to trust how someone is going to spend the money. You need to know that they're going to spend it as they say. You need something to reassure you that the person you're going to invest in won't squander it.



At a personal level, what was your biggest challenge?

How long everything takes. Everything takes longer than you think it's going to take, so that's an ongoing, continual challenge. Your enthusiasm gets beaten down by the fact that everything takes longer than you think it should but that's just the way the world is.


You can feel edgy and as if you're not going as fast as you should go and there is a little bit of fear that it mightn't work because you're not getting the answer straight away and it's constant. It's the same thing today. You should be doing this, but you can't even start until X and Y are finished, and as soon as X and Y finish this, B and C have managed to slide in. It can get very frustrating. At the end of the day we all want unlimited resources!



Any closing remarks for readers?

Fail early, fail often and fail cheaply. Recognise failure as quickly as you can. If a product isn't going to work, change it or bin it. Invest the minimal amount of capital, by which I mean both your money and your time, in order to prove the assumptions.


Historically companies would build the application and then push it to the market. Whereas what you should, do is get 500 dollars and put it into GoogleAdWords, drive 1000 visitors to a landing page that says ‘sign up here to receive a pack or whatever' and that tells you if people are interested or not. So for 500 bucks and a week of time, you have an answer to your key criteria. If the answer comes back that no they're not interested, then you change the product or you don't build the product and you will have failed early and cheaply.


Also, and I can say this with full rigour: when you're launching a product or a company, work out what all the assumptions are to success and work out which are the most important so that you have a table, there'll be six or seven assumptions and then work out how expensive it will be to test these. Some of them will be very expensive to test. So for example, retention rate will be expensive, but some of them will be cheap so test them first, because if they fail then you'll have saved both time and money in the long run.



Fail early; fail often and fail cheaply!







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