He's an affluent former non-league football club chairman more familiarly seen wearing horn-rimmed spectacles and sober suits.
But at 66, Oxford-educated Leon Shepperdson has decided to age gracefully is not his idea of fun so he is embarking on a career as a rock star.
The respectable suits have been replaced with trendy designer labels. The white hair has been bleached blond. He even has two tattoos, designed by former St Leonards club captain Keith Miles.
It is all part of Mr Shepperdson's vision of becoming a grey icon by cutting a 14-track album entitled Cruisin' For A Bruisin' with co-performer and writer Stephen Cullis, who he teamed up with 16 years ago.
It is an album born out of emotional crisis and a distaste for current musical fashions, which Mr Shepperdson hopes will prove there is more to life after 60 than bowls, toupees and daytime TV.
He and Mr Cullis, 36, have decided to bypass record companies by putting their tracks on the internet, where people can download them free.
Mr Shepperdson said: "We hope someone will take it and do something wonderful with it.
"People may say things about me or how I look but they cannot criticise the music because it stands in its own right.
"I may be maturing in age but I'm just like a 17-year-old when it comes to rock music.
"We take this very seriously. A lot of money has been spent setting this all up, especially on booking studios, so it's not something we are taking lightly."
His role as rock star marks another chapter in a colourful life which has led him to build on the success of the family business, Stamco Timber, in Bexhill Road, St Leonards, of which he is now chairman.
When chairman of Dr Martens football side St Leonards, Mr Shepperdson famously burnt Sasha Illic's goalkeeper jersey when he moved to Charlton, having paid thousands of pounds to bring him to Sussex.
Mr Cullis said: "He has got all the qualities of a rock star. He's got a great personality and is so enthusiastic about his music. And to top all of that, he's a truly lovely man."
Now Mr Shepperdson, who lives on The Ridge in St Leonards, has set his sights on stardom, whatever that may bring.
He said: "Who knows what's going to happen. Even if I've only got six weeks or six years left, I'm going to take everything I can out of it.
"And I'm going to be famous, really famous."
BBC Southern Eye follows Mr Shepperdson as he takes singing lessons and records his first songs.
It is being screened on BBC2 tonight from 7.30pm.
To access songs from Cruisin' for a Bruisin' log on to www.fux.org.uk
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