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Simon was educated at the University of Auckland, and also trained to become a Catholic priest. Though he completed his training, he did not seek ordination. Instead, he sought wider involvement in the community to make a practical, hands-on difference. Raised in Whangarei, Simon came to Auckland in 1994 to begin his university studies. Apart from his two years working on aide development projects in Fiji and a year spent in the United States, Auckland has remained his home ever since. Simon is a director on the board of Monarchy New Zealand, a nationwide constitutional lobby group, and is a frequent media commentator on constitutional and monarchical issues in New Zealand. He has been active within the National Party for many years, holding numerous offices, and was a list candidate in 2008.
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