Mickleson's lawyer Grant Illingworth QC told Auckland District Court his client realised his convictions will stop him gaining another senior role in the wine industry.
"Over 20 years of experience and expertise - all the knowledge he has gained is effectively down the drain.''
He asked the court to consider home detention and said his client was "utterly ashamed''.
But Crown prosecutor Robin McCoubrey said Mickleson deserved a term of imprisonment. He disputed the amount his victims had lost, which called into question the level of his remorse.
Mickleson, 43, previously worked as a wine consultant at Auckland's premier auction house Webb's while running his own business Fine Wines International.
The court heard he faked vintages by doctoring labels, stole credit cards, took cash for wine he didn't have, and sold historic chateau cases he didn't own for thousands of dollars.
"Some were clients of Webb's, some were clients of yourself and some were your friends. It doesn't get more serious in terms of a breach of trust than that,'' Judge Fraser said.
Webb's managing director Neil Campbell has described Mickleson as "the worst kind of try-hard''.
"Simon had this idea that being perceived as rich and wealthy made you a better person,'' he said after his former employee pleaded guilty in March.
"One day, he came to work in a new car and told us his grandmother had died and left him $3 million.
"But it turned out his grandmother wasn't dead, and he wasn't left any money, but he'd gone out and got a new car on hire purchase.
"He was always seeking acknowledgement of prestige and wealth, which was delusional.''
Havelock North wine merchant John Macpherson, who paid $36,000 for wine that never arrived, said: "He appeared to be a very plausible and well-connected character. But he just ripped everybody off.''
According to the police summary of facts, Mickleson's deceit began in 2007 after he promised Auckland surgeon Jim Shaw $400,000 worth of high-end wines.
Mickleson never delivered and over the next two years he compensated Dr Shaw by taking money from other clients and failing to deliver wine to them too.
In October 2007 Joong Sheng Giauw from Hong Kong paid Mickleson $66,313.08 for 36 bottles of Chateau Lafite Rothschild 2000.
That never turned up and Mickleson gave numerous excuses - on one occasion saying the wine was delayed in Sydney because it had been replaced accidently with a shipment of flowers.
Mickleson also targeted friends. In 2008 he asked schoolmate Julius Fox to help finance a $99,000 order of French wines for Dr Darren Reed who he claimed owned the private Ascot Hospital.
Mr Fox contributed $29,000 but the deal never went through. Police investigations revealed there was no such person as Dr Reed.
On another occasion, Mickleson changed labels from a case of 2001 Chateau Lafite Bordeaux to pass the bottles off as the sought-after 1981 vintage.
He tried to sell 24 fakes for $98,000, but the buyers pulled out after spotting the switch.
After pleading guilty, Mickelon was bullish claiming: "There are some companies who have behaved appallingly. It doesn't detract from the fact that I have done certain things, but there is far more to this.''
But last night he was behind bars and a woman who answer the door of his home in Auckland's Epsom refused to comment.
* Mickleson's company, Fine Wines International, is not connected to the similarly-named Fine Wine Delivery Company.
