30 May 2017 Last updated at 03:25 GMT

Should an entrepreneur risk it all?

should an entrepreneur risk it allThe Rich 200 list is littered with entrepeneurs who have sold their businesses.

Someone once said to me that they never wanted to be on that list because there are only two outcomes that derive from being placed on this list: 1. Telemarketers will harrass you for the rest of your life. 2. You will go broke.

Jan Cameron, the founder of successful retail chain Kathmandu knows this only too well. She built her business over 20 years to be the most successful retail business in the outdoor adventure space, selling for a reported $247 million and being placed on the Rich 200 list only to be in BRW today with the journalist reporting that she almost certainly won't be there this year. Why?

She sold her business and then after a break decided to get back into the game and invested $80 million into Retail Adventures discount group. Not long after, she had to double her investment to keep the chain alive. Plagued with poor management and a bad company culture, the chain was put in Voluntary Administration in October.

It's not all doom and gloom though for those on the Rich 200 List - of course.

Take entrepreneurs Adrian Giles and Andrew Barlow, two young men who built the business HITWISE and sold for $256 million and now are doing it all over again with WEBFIRM. Rather than sit on a beach (permanently), they re-invested some of their money into WEBFIRM and from all accounts, the business seems to be tracking well and innovating more than most web companies in the Australian market. It will be interesting to see if they can do it all again, but I am sure if anyone can - they can.

A good friend Jo Patterson, who now owns a new concept company in hair, beauty and well-being, sold her high pressured ad agency into BWM - Belgiovani, Williams, Mackay, a few years back. Rather than get back into the fast pace and the high stresses of the ad world, Jo sought to enjoy life and build a company that is all about well-being. She probably won't be dripping in the same type of cash she did from her previous business, but she will be happier ultimately.

Another great entrepreneurial success story is Bevan Clark and Guy King who sold their business Retailmenot.com for $90 million, only to start a new company Stateless Systems (Fundry.com, crushycms.com, trendsmaps.com). Can they duplicate the success of their first business? Something to watch for sure.

To risk your big pay day on the next big thing or showing the world and yourself that you can do it again takes alot of guts. It is something that very few people can do, but many admire. For every success, there are a lot more failures. Is it worth it?

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