Emigration had become the subject of political and public debate in Britain in the 1800s. and New Zealand had attracted much attention in England and Scotland as being one of the finest places to form a British colony. The first five ships chartered by the New Zealand Company carried some 800 people of which twenty percent were from Scotland. Aboard the Oriental, was Dudley Sinclair, eldest son of Sir George Sinclair, 2nd Bart, Ulbster. He was joined by neighbouring Scots from Sutherland led by Richard Barton. The Edinburgh Observer had described New Zealand as a perfect paradise on earth. However, those naive first settlers would soon find the reality was the complete opposite. On his arrival in Port Nicholson, Sinclair became a landowner and entrepreneur. He started the first brick making business in Wellington with Archibald Millar, a wealthy Scottish farmer. Sinclair set up the first Auckland newspaper, owned a steam mill, was a shipowner and merchant, with copper mines on Kawau and Waiheke Islands and was the first New Zealander to sail to China and Manila. When they set out from the old country, Sinclair and his friends were full of optimism, enthusiasm and expectations of success. Each one began with a promising start, though none would live happily ever after. Their lives were full of disappointments, setbacks and broken dreams and for some, an untimely or tragic death. Dudley Sinclair’s life told in full for the first time.