David Smith estimates he has flown in small planes piloted by Max Quartermain at least 300 times, right across the country in all sorts of conditions.
In late February, the agricultural real estate agent wanted to fly with Mr Quartermain again. He needed to get to the small town of Tumut, east of Wagga Wagga, where he was selling an apple orchid business.
Mr Smith contacted the pilot to ask him if he was available on the morning of February 21. Flying alongside him would be four of his employees, including his son and niece.
"We pushed him really hard to try and fly us on that Tuesday, Max said 'I'd love to take you but I've got this golf trip booked to Tassie'," David said.
When he realised the booking couldn't be broken, Mr Smith begrudgingly agreed to fly with another pilot the next day.
It was the last time they spoke before the plane Mr Quartermain was flying smashed into a DFO shopping centre shortly after taking off from Essendon Airport.
The February 21 crash, which killed all five on board including Mr Quartermain, has been described as Victoria's worst civil aviation disaster in 30 years.
It's the classic sliding doors moment, where fate could have just as easily led tragedy to befall you instead of someone else.
"It would have wiped out our business in one fell swoop and devastated our family as well," said Mr Smith. "I've never really had the time to be able to reflect that we dodged a bullet."
Mr Smith still can't understand how the Beechcraft King Air B200 ploughed into the shopping centre nine seconds into its flight.
Conditions were perfect for flying on that Tuesday morning just before 9am, much better than they often were when Mr Smith flew with Mr Quartermain.
"I've done that take off at least three hundred times with him, we've taken off in atrocious weather. Things that anyone would have been scared of," he said.
"I wouldn't fly in a small plane with anyone else, Max is so meticulous in his detail and checks."
The Australian Transport Safety Bureau is currently investigating the circumstances around the crash. A preliminary report ruled out engine failure and found that the black box was not working when the plane went down.
Mr Quartermain made seven mayday calls before the crash, according to air traffic control records.
The investigation will continue, with part of it to focus on Mr Quartermain's flying record, including a near miss with another plane on Mount Hotham in September 2015.
Mr Smith said he believed Mr Quartermain was trying to turn back to Essendon Airport after realising something had gone horribly wrong with the plane.
"He would have known that if it crashed they had no chance of survival because it was loaded with fuel," he said.
While he is thankful to have missed being on that fateful flight, Mr Smith said he and many others were still mourning Mr Quartermain's loss months after the crash.
"It's bittersweet, people say 'you should buy a Tattslotto ticket' but it's really difficult because you've lost such a good friend."