The latest episode of Success and More Interesting Stuff introduces one of the most enterprising and successful people on the corporate landscape. Robert Kelly had a chequered career in the 1970s and 80s that included a failed business, driving taxis and dealing with some of Sydney’s more colourful identities.

In 1996, aged 48 and running his own insurance broking firm, Kelly decided it was time to put the foot to the floor. He, along with some other like minded insurance brokers, thought forming a buying group to help deliver cheaper insurance rates for its members was a good idea. They called it Steadfast.

Most good idea only come to fruition due to tireless endeavour. Kelly criss-crossed the country convincing Insurance brokers they should become a Steadfast member. He was obviously a sharp salesman. From humble beginnings, Steadfast now has over $11 billion of gross written premium from its members and accounts for more than a third of Australia’s intermediated insurance market. The company’s market capitalisation is approximately $6 billion.

Kelly is hardly calling it quits though. At the age of 76, the Steadfast board recently extended his tenure as CEO of the group until 2026. That should give him time to take Steadfast into the US market, a stated objective of the organisation. One can only guess how big that arm of the business will become.

Nick Stageberg

The AI-powered Podcast Player