Interviews

Why the serial entrepreneur behind Secret Escapes and Dealchecker hates that particular tag

5 min read

30 March 2015

More than 15,000 people on LinkedIn currently describe themselves as "serial entrepreneurs", an indication that starting more than one business is seen by most of us as a good trait and something worth shouting about.

Very often those who are thought to have achieved overnight success in the world of business are in fact on their third or fourth attempt. In the US for instance, tech entrepreneur Omar Hamoui hit the headlines with the sale of his mobile advertising network, Admob, to Google for $750m in 2009 – but he had already started four companies before finally achieving this spectacular success.

So what makes a successful serial entrepreneur and what can those working on their first and perhaps only business learn from them?

Troy Collins, 35, has just launched his third business. Fashion advice site Endource.com searches through magazine websites and influential fashion blogs to produce for shoppers what it describes as “the ultimate fashion directory with unparalleled access to editor-approved style”. The site claims to “take the doubt and the fear out of shopping”.

Other algorithmic programming and image recognition technologies have failed to accurately match fashion product images to the actual products themselves, according to Collins, and so Endource.com solves the problem of identifying the subtle difference between, for example, a pair of Christian Louboutin Pigalle heels and a generic pair of high heel courts, he said.

Collins was previously involved in the start up of the successful luxury holiday flash sale site Secret Escapes and Dealchecker, a flight, accommodation, holiday and car hire price comparison service. “I hate the term ‘serial entrepreneur’,” he said. “I’m just someone who’s lucky enough to have been involved in three exciting, successful businesses.”

He enjoys making what he calls the “critical decisions”, those that dictate the success or otherwise of a business during its startup phase – rather than the day to running of an organisation. “It’s coming up against problems and then solving them that excites me,” he said.

Collins, who came to the UK from Australia in 2000 and regards himself an “Australian Londoner”, points to strong synergies between all three businesses, even though his latest is in fashion rather than travel. Part of the thinking behind Endource is that fashion is currently undergoing the transition into online “advocacy” that travel went through years ago with Trip Advisor and other sites. Having contacts among angel investors from his previous two businesses has also helped with the setting up of Endource.

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According to Deborah Webster, a specialist in understanding cultures and human dynamics, and a thought leader and trusted adviser in the field of talent and responsible business, the key to being a successful serial entrepreneur involves taking an idea or principle that has worked in one sector and applying it to another. 

“It’s about looking at sector and working out where, using your experience, you can add value,” she said. More broadly, she believes that entrepreneurs often fall into one of two categories. “You often find that there are ‘set up people’, and ‘management’ people. Some like to run a business successfully in the longer term and others enjoy the challenge of starting something new.”

She added: “Part of the skill of being a serial entrepreneur is to be able to set up teams that will be able to work together after you’ve moved on to your next project. These teams have to be committed to the purpose of the business not just to you as the founder, otherwise they’ll fail after you’ve left. That involves successful delegation and proper succession planning.”

Steve Jobs, the founder of Apple, has the skill set that made him well suited to setting up a business but he managed, like many people, to run a business. Part of his success and his ability to innovate, though, believes Webster, was due to the fact that even when Apple was well established he constantly thought along the lines of a ‘set up’ person. Combining both of these skills would work well for any SME owner.