By 1998, Ryan Howsam, now 45, was in trouble. Throughout the 1990s, he had built up a chain of "18-30" stores selling clothing, holidays and a popular discount card for regular clubbers. But as it began to struggle, he "decided to wind it up and look for something else". That would prove to be a smart move.
A keen golfer (he had considered turning pro as a youngster), he decided to create a new discount card that offered deals for short golfing holidays around Britain. Howsam got the cards placed in a number of sports retailers. As sales increased one of them, JJB Sports, asked if he could provide golf insurance too. "Golf insurance covers the usual stuff like losing your clubs, but it also takes care of extras, for example if you hit someone with a golf ball."
Howsam worked on an online platform that would allow people to buy the insurance and found an underwriter to put together some different golfing insurance options. The success of that product convinced him to try for a much bigger market. "I felt that it could work for travel insurance."
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In 2004, Howsam formed travel insurance firm Staysure. "I wasn't a registered broker so I found one to represent me." He invested in a website and booking engine to handle new business. His plan was to focus on the over-50s market, where margins are higher. "Older travellers are less likely to claim for theft or loss of goods but more likely to claim for medical problems."
By this point, he had moved to Spain and hired British expatriates to work for him. As sales grew, he reinvested everything in the business, especially in marketing. He also managed to get favourable advertising rates from the bigger search engines by registering himself as an advertising agency.
By 2005, sales had hit £500,000 and Howsam felt ready to register himself as a broker and establish a direct relationship with underwriters. "Going through another broker meant that we hadn't been getting the best prices for our products." The new deals helped Staysure win more custom and in 2007, he built a new call centre in Spain.
With business booming, Howsam decided in 2009 to court investors. "I was thinking of selling a 25% chunk of the business." The business was valued at £6m, but would-be buyers didn't like the fact that a British insurer was based in Spain.
Howsam decided he should return to Britain and broaden his services to become more of a general insurer. He began offering motor, home and medical insurance, while retaining his focus on the 50-plus market. He hired "senior staff who were specialist insurers and understood each of the new markets". However, "it is hard to get good deals from underwriters when you don't have large numbers of customers. And of course if you haven't got good deals it's hard to get new customers."
Fortunately the successful travel business rode to his rescue. It funded an extensive marketing campaign, including TV advertisements, and enabled Howsam to cross-sell new products to existing customers.
Last year Staysure sold £20m of insurance cover and made The Sunday Times Fast Track 100 for the second year in a row. It is now valued at £30m, and Howsam believes sales will reach £100m within five years.
James graduated from Keele University with a BA (Hons) in English literature and history, and has a NCTJ certificate in journalism.
After working as a freelance journalist in various Latin American countries, and a spell at ITV, James wrote for Television Business International and covered the European equity markets for the Forbes.com London bureau.
James has travelled extensively in emerging markets, reporting for international energy magazines such as Oil and Gas Investor, and institutional publications such as the Commonwealth Business Environment Report.
He is currently the managing editor of LatAm INVESTOR, the UK's only Latin American finance magazine.
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