Should an entrepreneur risk it all?

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?