From a North Otago farming background, Mr Simpson (26) achieved that ambition on Monday, officially taking over Bennett Transport, supported by his parents, Michael and Jane.
His dream was always to be a farmer and he did not intend on being a full-time truck driver until he "accidentally" ended up at Bennett Transport.
At 19, he came to help owner Jim Bennett move straw out of Fairlie and he had been at the firm ever since.
"I love farming but transport or trucks are a major part of the way I’m wired," he said.
Coincidentally, Mr Simpson’s great-grandfather established a transport business in Invercargill many years ago.
And while Mr Simpson was now officially the boss, he still wanted to be "one of the guys", something that Mr Bennett had managed to achieve.
"He’s the boss but he understands what you’re talking about."
Prior to selling, Mr Bennett and wife Mel, who has been an integral part, were in their 25th year of the business.
They moved south from Christchurch wanting a business that was aligned to farming and for their three children to attend a country school.
At that stage, the business was just one truck, operated previously by Murray Stackhouse, and Mr Bennett was the sole driver.
Their desire was to be the local carrier and, while the phone would ring at all times of the day and night, that was "what the local carrier is", Mrs Bennett said.
Their home and yard was near Ngapara, in the heart of the North Otago countryside, and they were grateful to have moved to such an "amazing community", she said.
When they first arrived, there was a drought in North Otago and farms had destocked so there was little stock to cart.
Fortunately it rained and then irrigation later came. That meant the type of farming changed and also their business changed.
Initially, there was a lull in the middle of winter because their business was predominantly sheep and lambs but the advent of widespread irrigation meant more dairy conversions and their year being more spread out.
They now had 10 trucks and driver numbers were usually about seven or eight, it varied depending on what part of the season. Mr Simpson was also looking to hire.
Mrs Bennett said the couple had "lived and breathed" the business and it was time for someone with fresh ideas and enthusiasm to take over.
Initially, Mr Simpson had leased the Bennett yard but it would later shift to the Simpson family’s farm Limavady.
The couple were helping him transition into his new role and Mr Simpson was also incredibly grateful to the support of his parents.
As a young boy, Mr Simpson would accompany Mr Bennett sometimes in the truck and, with a passion for trucks and machinery from an early age, he would be constantly chattering.
Mr Simpson described himself as a people person and dealing with people was the part that he enjoyed the most.
His goal was to have happy clients and to provide the same service that Mr and Mrs Bennett did which included supporting community groups.
And that service was a very personal one — even though the jobs were now automated, drivers were rung by Mr Bennett every night.
If the Bennetts were ever away, Mr Simpson had been 2IC so he already knew about how the business ran "and he’s got the right brain for it", Mrs Bennett said.
The couple were looking forward to having more free time and catching up with their children.
Mr Bennett was very grateful to everyone who had supported them and he was pleased to see a young person take the business over.
While there had been all sorts of challenges over the years — "as John will find out" — the business had been everything he wanted.
Mr Bennett loved the driving aspect, saying the administration side was not why he bought a truck, and the couple would "find something else to do" after taking some time out.
He reckoned the biggest thing he would notice was his phone no longer constantly ringing and he would miss the interaction with clients.
