While not a lot of fun for a young kid, the 31-year-old admits his father's tough love helped shape him into the business man he is today.
"I have jumped into building a start-up, employing my own staff and holding the fate of my own future - a very risky, low paying career with the opportunity to build a multimillion-dollar business and a lot of craziness along the way," he said.
"Without this guidance, I do not think my perseverance would have lasted the ups and downs in getting our high growth crowd-funding business to where it is today."
Gilbert doesn't think the key to success can be found entirely through tough love, with a balance needed between nature and nurture.
"I think entrepreneurs are wired differently and have a great desire to change something for the better or introduce a new way of thinking - quite often against unrealistic odds," he said.
"I do believe that an aspect of entrepreneurship is a crazy gene passed down in the family and is most certainly not for everyone.
"I also believe that it is enhanced through the way people are brought up and the values that parents instil in their children."
Gilbert isn't the only Aussie tech entrepreneur to have developed skills during childhood, with Brosa co-founder Ivan Lim remembering business focused chats at the dinner table when he was just 10.
By the time he hit high school, he was never asked about drama class, rather the focus was on what business idea did he have that could get him AU$100K (NZ$108K) in revenue.
Entrepreneurs are wired differently and have a great desire to change something for the better or introduce a new way of thinking - quite often against unrealistic odds.
Lim far exceeded these expectations, with his practical design-led furniture company raising AU$2m (NZ$2.1m) in funding to date.
While he still advocates for a strong work ethic and tenacious attitude as a path to success, the Melbourne resident thinks his parents' teachings were vital in helping him be where he is today.
"You can be born with a natural predisposition to the qualities that make an entrepreneur, but I also think you can be taught these over time," he said.
"It's never too late to grow and take up entrepreneurial instincts. Good entrepreneurs are naturally ferocious learners."
Co-founder of Weploy Tony Wu attributes his childhood spent with two entrepreneurial parents as the core to his success.
"I believe entrepreneurs are made through life experiences. For me, I was born just like any other kid, but watching what my parents went through, I was made into an entrepreneur," he said.
"As far back as I can remember, I would spend my weekends with my parents, watching them and helping them grow their business."
Wu also believes his family's immigration to Australia helped inspire the idea behind his AU$1m (NZ$1.09m) company that connects businesses looking for short term support staff with employees searching for work.
"Having migrated from China, my grandparents arrived in Australia with almost nothing. So for them, they had a different view on what business could do for their lives. For them, being able to create a business signified freedom, shelter and food."