Part of the secret to being a good entrepreneur is to be lucky. There is undoubtedly an art in identifying the right opportunity at the right time - even if it stems from little other than a gut feeling - but people still have to be able to take advantage of such moments and, just as importantly, pick the right moment to exit. There's a fine line between success and failure, and in many ways the timing is all-important.


There's no doubting that Simon Nixon, founder of, is a fine entrepreneur, having spotted the potential for various businesses and acted on those impulses over the years. Yet he owes much too to his sense of timing, both in identifying the potential of the internet as an easy means of allowing professionals, and later consumers, to compare financial products and in his decision to sell 47% of his stake in early 2007, just a few months before the credit crunch hit, in biggest pure play internet flotation in Europe. "No one could have seen we were about to have one of the worst credit crunches in the last 100 years so it was just totally luck," he admits. "I can't take credit or for that."


You get the feeling that Nixon, however, was always set to become an entrepreneur. "I always wanted to be successful as a kid," he says. "I had a wealthy uncle, and we'd visit him maybe once or twice a year, and he had a lot of things that we didn't have. Very naively, I would always have a go at my Dad and ask him why he hadn't done better and why we didn't have those things. But it was my uncle who was the inspiration really, as he came from nothing.


"Whenever people asked me when I was very young what I wanted to do, I would say I wanted to be a successful businessperson," he adds. "The other thing is that I was always very independent as a kid and hated being told what to do. I think that's a characteristic of an entrepreneur, in that they want to be in charge of their own destiny."


For a while, though, it appeared the young Nixon might be headed for a more conventional career route working as a doctor or dentist, before a summer placement made him realise it wasn't for him. He ended up going to university through clearing, studying accountancy at Nottingham University. "I just thought would fit in with a career better, so I was sort of strategically planning even at that early age," he says. "Most kids just picked the courses they would enjoy but I picked mine because I thought it would lead to success." He attributes this attitude to insecurity - a theme that crops up sporadically throughout our interview - and a desire to not be reliant on other people.


As it happened, though, he didn't enjoy his degree and dropped out after two years. "There were various catalysts for that but my mum died when I was 19 while I was at university and I think that had a big impact," he says. "It made me more insecure and more determined to actually go out there and make it and be independent."


Returning to his hometown of Chester, his Dad insisted he get a job and he ended up working as a financial consultant in a regional business. "I remember the advert said unlimited earnings, so if you worked really hard you'd earn more money, and I thought that seemed fair," he says. Before long, he'd specialised in mortgages and struck a deal with a leading housebuilder to organise products for people who came into their sales office. "It was a win-win situation because they lost a lot of house sales through people not being able to get mortgages, and for me it just seemed totally logical to go and do a deal like that rather than prospect in the normal way that a mortgage broker would. I became I think the top salesperson at the company within about four months at the age of 20."


It was this business, though, which gave him the idea that would see him start up his first venture and eventually pave the way for Moneysupermarket. "I was becoming increasingly frustrated that it was taking me a long time to research the best mortgages for my clients," he says. "I just felt that there should be some sort of trade magazine that helped mortgage brokers find the best or most suitable mortgages for their clients. So I bought an Apple Mac computer and in the evenings started designing a magazine, and I launched a very rough one about three or four months later. It started to really take off because it was the right thing at the right time, to the extent that within three months of launching I had handed in my notice and set up this magazine full time."


The title was successful for a few years, he says, but after that sales started to dip. "It was because mortgage brokers were starting to buy computers and wanted something that was updated daily, because obviously mortgages change rapidly," says Nixon. "I spoke to my girlfriend's brother, who was two years into a computer science degree and he agreed to write a mortgage sourcing system, which would help brokers find the best mortgage for their clients." Within a year, the duo launched Mortgage 2000, which rapidly became the main tool in the marketplace and still exists today.


Dotcom boom

The real change, though, came in 1999, when Freeserve launched the first free internet access and the potential emerged to offer a similar product to consumers. "I could see that the internet was really going to take off so I had the idea of letting consumers compare every mortgage in the marketplace, which hadn't been done before," he says. "I called the website because I could see that we could move into anything: loans, credit cards, savings or anything that customers want to compare to find the best value and buy online." Today the business offers around 70 or 80 categories, he says, and notable developments along the way included insurance and, which operates as a separate brand.


Nixon attributes much of this success to the use of marketing to drive traffic to the site. "We didn't have £20 million pounds a year to spend on television advertising, and at the time internet penetration was so low it would have been a waste of money anyway," he explains. "So we became very good at PR, and we made sure that whenever the financial press was talking about personal finance that we were quoted. Secondly, there were a lot of big internet sites out there at the time like Freeserve and Yahoo! with lots of customers but they had very poor personal finance sections, so I persuaded most of the big websites to just take Moneysupermarket's personal finance comparison content. Within a year or two we were getting most of our business from third-party sites, sharing any commissions with them."


After a few years, Nixon decided this was an unhealthy situation as partners pulling out could have left the business vulnerable, and at that point it did invest in television advertising campaigns. "We decided to really try and build a brand, and so that's when we started advertising, and that drove a lot of customers direct to our site and really helped from a brand and a trust point of view," he says.  


There were, however, plenty of sacrifices made along the way. "Building the business up to the point where we could float it for that sort of value was really difficult and it became my life," he says. "I'm not married, and I don't have children. I still speak to staff now who were there years ago and at the time they were told that if they ever spoke to me the only thing that I would speak about was Moneysupermarket. I was very one-dimensional but you really have to give it everything until it gets to a certain size and then you can start delegating more. I have a much more rounded life now but I certainly don't regret anything that I've done."


Before long, though, profits were doubling every year and the early 2000s were a period of rapid growth as internet usage in the UK soared. Once again, though, Nixon's insecurity got the better of him and he took the decision to cash in some of his shareholding. "I felt that I needed to sell part of my stake, and I just felt the best way of doing that was to float on the London Stock Exchange," he says. "We got a value of £850 million so I was able to retain 53% of business but still get the money out of the business."


In hindsight, with a downturn looming just a few months away, it proved an extremely prudent move. Nixon continued as a "corporate entrepreneur" for two years in a chief executive capacity; something he initially enjoyed but then came to resent. "I just grew to tire of updating the City and presenting on a quarterly basis and I realised there were other people on the board that would probably be quite a bit better than me at doing that," he says. "I made the decision to step down and I appointed Peter Plumb, who was on the board, as chief executive and I became deputy chairman, so I still work one day a week for moneysupermarket and own over 50% of the business."


Since then, Nixon has embraced life as an entrepreneur again, relishing in starting up ventures and having the freedom to diversify his interests. He's made a number of investments in property and is currently developing a beachfront complex on prime estate in Barbados, as well as Majorca and Cornwall, which will be rented out as luxury holiday destinations through


"All my assets were in a virtual business and when I took money out of that, I just wanted to put it into something that was real and bricks and mortar, and from an asset point of view that is as real as it gets," he says. "But a lot of people have said that when they rent a holiday property with their friends and their family a lot of the time they're not as good as their actual home and they wanted something that was better because it's a treat. Maybe that's a gap that I can fill in the marketplace."


Aside from that, Nixon has a family office in Silicon Valley, San Francisco, where he invests in internet start-ups through venture capitalists. "At the age of 44, it's unlikely that I'm going to come up with the next Moneysupermarket, Facebook or Google," he says. "It's more likely to be some 25-year-old out of Harvard who has been bought up on the internet. We also invest in the stock market and we've got a massive bond portfolio, so we're almost becoming in our own way a hedge fund. So that takes up quite a bit of my time, and obviously I'm still actively involved in Moneysupermarket."


Opportunity knocks

The current economic climate lends itself well to new businesses, says Nixon, partly because competitors are less likely to be able to react. "If you're launching something that's disruptive, then you're potentially going to be a big piece of that market, so there are advantages to launching in a recession because the competition generally isn't expanding," he says.


Potential entrepreneurs, though, will need to be even more thorough in their market research and prepared to put in the kind of legwork Nixon himself did when building up his empire. "You've got to be prepared to work all hours and it's got to be a total focus," he says. "If you're going to give away shares and set up the business with a partner, be absolutely sure that you both have totally different responsibilities because you don't want to overlap, so you make sure your skills complement each other." Using social media to spread the word about a business is a useful way of driving interest and sales in a low-cost manner, he adds.


Once a business gets off the ground, the hardest part is managing people and keeping staff motivated, says Nixon. "You need to have very good people around you at board level," he says. "You might have an HR person who is very good at keeping staff motivated because entrepreneurs generally aren't great people-people. It's about having the right people who complement you, and who can do all the things that you're not very good at. The entrepreneur should be all about the ideas and pushing the business forward and being as constructive as possible, but there's a whole load of other things that need to be done that aren't involved related to ideas and you'll need people to sweep up after you."


As for his own future, Nixon says he has enough on his plate with the family business, SimonEscapes and his ongoing commitment to Moneysupermarket to keep him firmly occupied for now, and says he's unlikely to start up another venture himself. But, like the restless entrepreneur he has always been, he won't rule out getting involved in another project. "A lot of people offer me opportunities to invest in their business directly, and I've resisted that up until now, but that's something that I may do," he says. "I might get involved in some other internet ideas if I really like them. I think that's more likely than me just setting something up totally on my own."


For now, though, he's more than happy to enjoy the fruits of his success, mixing business and pleasure as he does so. "I'm far more diversified as a person now than I ever was before," he says. "I don't work 14 hours a day now - I probably work nine - and I take much more holidays. I always used to feel guilty about going on holiday, even if I only had three or four weeks a year. Now I've hit that utopian situation where I'm on holiday but I'm working. I'm really enjoying it." That old insecurity, you feel, may finally have been laid to rest.


 How Simon Nixon went from wannabe entrepreneur to online millionaire

1968: Born in Stamford, Nottinghamshire


1988: Dropped out of an accountancy degree at Nottingham University and starting working as a financial consultant for a north-west mortgage firm. This gave him the idea of creating a magazine providing information on mortgage products for advisers


1993: Founded Mortgage 2000 with his former business partner Duncan Cameron, offering mortgage brokers up-to-date information on the various products on the market


1999: Launched, after spotting the potential of the internet to share up-to-date information with consumers


2004: Oversaw the launch of


2005: Awarded the title of Cheshire young business director of the year


2007: Sold a 47% stake in the business, which was valued at £850 million in what remains the highest valuation achieved by a European internet-only company. Remained with the company as chief executive


2009: Stood down as chief executive and became deputy chairman, to pursue other business interests


Launches high-end holiday rental business SimonEscapes, offering luxury accommodation in complexes built and owned by the business