"He was ridiculously annoyed at me — to the point he was actually swearing at me — because I wasn't at home to receive the parcel.
"I had to ring the courier back and reschedule a time for it to be delivered and it frustrated me so much."
Mr Orenstein soon realised he probably wasn't alone in his frustration, and the idea for his delivery business Zoom2u was born.
The platform, which allows people to track where their parcel is in real time via GPS technology and provides them with the driver's contact details, launched in late August 2014 with just five drivers.
But after one month, 250 deliveries had been made.
Since then, the company has raised more than $4.5 million in funding and has been growing 100 per cent year-on-year.
It has grown its network to more than 1300 drivers located across the country, who drop off everything from small parcels to large machinery.
So far, more than 600,000 deliveries have been made via the company's "under three hour", "same day" and "interstate" delivery options.
The 38-year-old said he knew he was onto a winner almost immediately.
"I thought the opportunity was there but I wasn't naive; I knew it would take a lot of hard work to build and that it would be a challenge," he said.
"But customers liked communicating with the drivers and knowing when the driver would turn up so they didn't have to sit around for an entire day."
He said the "pick up and deliver" market was worth a whopping $4.5 billion per year in Australia and that the growing popularity of online shopping meant that demand would likely continue to increase.
However, Mr Orenstein's success with Zoom2u is only part of his story.
The software start-up expert dropped out of his IT course at uni and at just 19 years of age he launched a company that fixed computers for small businesses, before establishing job management and scheduling application Connect2Field which was acquired by Fleetmatics Group in 2013.
It has been widely reported that Mr Orenstein sold his last company for $7 million, although he was unable to confirm that figure due to contractual agreements.
Zoom2u will exhibiting at the upcoming Online Retailer Expo and Conference, which will be held on July 25 and 26 at Sydney's International Convention Centre.
Speakers at the 2018 event will include Showpo's Jane Lu, Deliveroo's Levi Aron and Myer's Mark Cripsey as well as representatives from Ikea, Big W, Netflix and Google.