`The X Factor` boss is planning to have his corpse preserved in ice, in the hope future technology allows him to be thawed out and brought back to life.
He told America`s GQ magazine: "It`s an insurance policy. If it doesn`t work, it doesn`t work. But if it does work, I`ll be happy.
"If it`s possible - and I think it will be - why not have a second crack? Does that sound crazy?
"I think it`s a good idea. I have a feeling that if I don`t do it, I could regret it in 300 years."
The cryogenic freezing process costs up to £120,000 and is offered by two companies in the US. So far over 1,000 people have signed up for the scheme.
While he is still alive, however, 51-year-old Simon goes through a rigorous routine to ensure he stays at the pinnacle of health, including an intravenous drip of vitamins, which he takes weekly, and drinking super healthy smoothie cocktails containing spinach and fruits.
He added: "I love to wake up in a good mood and look forward to what`s coming. As soon as that tray is put in front of me, I can`t wait to have it."
Simon - estimated to be worth £300 million - has also ruled out leaving his fortune to individuals after his death, planning to instead give his riches to charity.
He said: "If I was given a ton of money when I was 21, God only knows where I`d be now.
"Leave the whole lot to charity. You enjoy it while you`ve got it, then it`s gone to good causes."