Aussie entrepreneur worth $100m reveals key habits to business success

From skydiving to journaling, one of Australia’s richest young entrepreneurs has revealed his secrets to growing a multimillion-dollar business.

The entrepreneur behind a $100m fortune has revealed how he has kept his sanity and work-life balance while building his company.

Jack Delosa, the founder, chairman and executive director of business coaching provider The Entourage, urged business owners to find their own version of self-care and to invest time in staying healthy.

For him, that used to be skydiving.

“Going back 10 years, I was jumping out of planes; often we’d skydive with 100 clients in Melbourne on a Saturday and fly back to Sydney and jump out of a plane with 100 clients on Sunday,” he said.

Though he’s skydived ‘plenty of times’, Jack Delosa says a 10-year gap between jumps meant he was terrified during his return plunge and that it felt like he was doing it for the first time.

“I‘d go whitewater rafting and I’d look for all of these kinds of adrenaline things because that’s what juiced me at the time.”

However, after years of adrenaline seeking, he found that the risky activities “just didn’t do it” for him anymore.

“So I went from [skydiving] to sitting down with a cup of tea and journaling and spending time with my partner, my daughter, so happiness strategies evolve as they do.”

The sharp turn away from thrillseeking and toward self-care began when the entrepreneur woke up one day after 10 years in business and found he couldn’t get out of bed despite being young and healthy.

“I didn’t have the language for it then, but I was completely burnt out. And so I had to find ways to engage in self-care and kind of look out for myself, not just my businesses, or else.”

“Being an entrepreneur is very similar to being an athlete; though there’s often sprinting involved, it’s an endurance race – you need to be fit, you need to be focused.”

He had built a member base of close to one million for The Entourage.

Mr Delosa suits up to jump out of a plane, something he hadn’t done in 10 years.

He leapt from a plane 14,000 feet in the air, roughly 4.2km above the ground.

Mr Delosa says some of the simplest things benefit him the most, with journaling and meditation a part of his daily life for the past seven years.

“Journaling is really therapeutic for me. I started to integrate meditation into my days in 2016,” he said

“I was going through a horrendously painful period in business in 2016; I had to do that to maintain my sanity. And it works; I kept doing it,” he said.

That difficult period was caused by the government’s decision to cut back on funding for students, a move which could have ended the business.

There were periods when it faced the possibility of losing $900,000 a month and when it had to cut over 50 per cent of its staff in a short time period.

He said these “happiness strategies” were what “kept him sane” amid a turbulent period, and urges other business owners to find their own.

“It’s different for everybody but my advice is find out what fills you up and then try to habitualise that into your weeks and days as much as possible,” he said.

“Whether that’s journaling, whether that’s exercising … for some people it’s playing the guitar, for some people it’s painting, for some people it’s time with the kids … it’s such a boring answer because it’s so basic, but this is the thing with humans.”

Mr Delosa jumped out of the plane alongside entrepreneur Jess Davis, who co-founded the health brand Mr Potato with her partner Tyson Hoffman and is a member of The Entourage.

Despite his lifestyle change, Mr Delosa returned to the sky to promote his new book Elevate, jumping out of a plane at 5000km above Sydney.

“We have just jumped out of a plane because it represents the risks that business owners take every day, coming out of Covid and into a recession and forms of a recession,” he said while parachuting down from thousands of feet in the air.

“Because business owners everywhere are doing more, they’re working harder with a lot less.”

Mr Delosa urged business owners to stick through the current economic climate, saying “hard times can be really good”.

“In business, it’s a little bit counter-cyclical. What I mean by that is when times are hard, business owners improve and therefore often performance turns around.

“Elevate clients developed more improvements and better businesses throughout Covid in those two years than we had in a five-year period preceding that.”

Though the rich-lister is only required to spend “90 minutes a fortnight” on his business, he said he chooses to dedicate “pretty much every waking minute on business of some sort”.

Jack Delosa has urged businesses to see the current economic climate as an opportunity to grow.

‘Everything covered in Elevate has been tried, tested, proven and optimised with thousands of our clients at The Entourage, spanning over 150 industries, since 2010, and has generated over $2 billion for them,’ Mr Delosa said about his book.

“But it’s projects that I love to do, and it’s projects that are of the best use and contribute the most business.

“I just spent two years writing a book, not because I had to, but because I was really inspired coming out of Covid, seeing the challenges business owners are facing. I was able to do that without the operational distraction of needing to be in the office every day.”

He says more business owners need to adopt this model, both for their personal and professional lives.

“What makes business owners go insane is when you don’t understand how to structurally build a successful company.

“What we tend to do is just work more, work more, work more, work more, work more, and that leads to 60, 70 80, 90-hour weeks, and it’s just unsustainable.

“So counterintuitively, the better you become at building a business, often the less you will actually work in it and the more successful it will become.”