He created the website Planeapidea, which he dubbed the "Wikipedia of Planes", after watching his mum become stressed while going through the airport on a family holiday.
The website became so popular that, at the age of 15, he partnered with Qantas and Singapore Airlines.
He was also invited to attend a five-day Magic Moments youth leadership and business summit in Sydney, which is where he got the idea to start the Youth Leadership Academy Australia.
"I was like, I want to bring that event to Perth in a one-day forum and that is when I started Youth Leadership Academy in Australia, not with the intention to start a business but with the intention to just have a legal or legal foundation to accept money," the 20-year-old told news.com.au.
"We started selling tickets to a one-day event in Perth in 2018 and we had 65 students and five schools."
Fast-forward four years and Massara is now a sought-after consultant and speaker, providing his services to about 500 schools this year and impacting more than 10,000 students.
Starting his business at such a young age, Massara found himself pulling back from his education in order to focus on his new venture.
"I quiet quit before it was a trend. Because I didn't drop out of school, I failed school.
"In Year 12, I had 51 per cent attendance and any time I was at school I was working on my business."
The "quiet quitting" trend has recently gained traction, particularly among young workers.
It is essentially a rejection of the idea that work has to take over your life and that you, as an employee, should be going above and beyond in your role.
Instead, people are now reverting to only performing the duties outlined in their job description and politely declining to take on any more responsibilities outside of that or work longer hours than necessary.
Despite his frustration with the education system, Massara still highly values education and is currently completing his Masters in Business Administration.
Massara said Australia's work culture has drastically changed in the past few years, with workers now moving away from the "hustle" culture into something a lot more balanced.
"I believe it's a realisation that they don't need to be exploited anymore for overworking and having the confidence to be able to actually stand up and say, 'What are our other options?'" he said.
Wil Massara went from speaking to 50 schools to servicing 750 in just 18 months. Photo / Wil Massara
"Five years ago, people were bragging about how little sleep they had had and that being a measure of success.
"Now the new vibe is, 'How healthy are you?' and 'How much are you working?' I think that sort of shift is something that's really healthy."
The business owner said this challenges the expectation that you are "meant to work until you are dead".
"I think our generation has a real awareness that life is short and things happen and, especially off the back of Covid there's a real awareness of, let's not let the time that we have now be wasted."
Massara also placed importance on collaboration between older and younger generations, to ensure the conversation around different approaches to work and pathways to success are met with empathy and understanding from all sides.
"That intergenerational collaboration is going to be the thing that allows us all to actually build a future that we can look forward to and develop and strengthen those relationships, rather than trying to tear each other down," he said.
Company to hit $1 million revenue
Next year, Youth Leadership Academy Australia will hit the $1 million revenue mark, a goal Mr Massara never anticipated he would reach, especially not so quickly.
When he first came up with the idea, it was purely to allow him to put on an event in Perth that would hopefully help and inspire some local students.
"Never did we think we'd be running events in every state and being some of the market leaders in leadership development for young people," he said.
Massara is so committed to making a real change in the lives of young people, that he is working to change Youth Leadership Academy Australia into a social enterprise.
This means 100 per cent of profits will be put back into youth suicide prevention programmes.
"That decision was made off the back of a series of events this year. We had such epic results, but we also had heartbreaking results," he said.
The responses to his events made him realise just how much of a positive impact he could have, but also that there was more that could be done.
Massara then asked the question of how can his company double its impact.
"Which now looks like us looking for corporate sponsorship, corporate partnerships and moving to a model that has that double impact of delivering early intervention and then funding prevention," he said.
Massara said he wouldn't be where he was without all the support he has received along the way.
He enlisted the help of The Entourage, which is Australia's leading business coaching and training provider for six, seven and eight-figure business owners.
The 20-year-old said the coaching provider helped him increase the number of schools he was working with from 50 to 750 in the space of 18 months.
"I think, now more than ever, schools and organisations and communities are realising the power of young people when we work together and when we collaborate," he said.
"There's no more important time than now post-Covid that young people need to come together and be empowered and inspired to create change within their communities."
