Here at Sydney Social 101 we love to support local talent and are no strangers to the Cleo Bachelor of the Year competition. More than just looks, we’re super impressed by finalists that are able to bring more to the table than rippling abs! At just 28, Jack Delosa has launched several start-ups and has even worked with Sir Richard Branson to develop the curriculum at Branson Centre of Entrepreneurship in South Africa. (Yeah we know, he’s not just a hat rack).

He is Australia’s most awarded entrepreneur under 30. His business career started at 18 when he dropped out of a commerce/law degree against the advice of family and friends, borrowed $20,000 from the bank and bought into his first business – a business to business call centre in Melbourne. Now eight years and four businesses later Delosa is recognised as one of Australia’s most successful entrepreneurs.

We caught up with Jack to find out what he looks for in a woman and his latest venture: The Entourage, The Australia’s biggest community of entrepreneurs with 100,000 members around the world

What are your top dating tips?


Be authentically yourself. People crave real, people want to laugh, have fun, genuinely connect. Drop the mask, be you and see if magic appears.


What qualities do you look for in a woman?


I love a woman who knows herself and is confident in that. Someone that stands for something, is on path and radiates from the inside out.


What is the best thing about your ‘job’ / Tell us a bit about The Entourage?


The absolute best thing about my ‘job’ is my Team. At The Entourage we recruit not based on resumes but based on the essence of the human being – we look for genuinely exceptional and generous people. Spending any moment I get in Sydney with a family of 70 like-hearted people is just magic.


What’s the best advice you’ve been given by Sir Richard Branson? 


One of the best things that Sir Richard Branson has done is built so many businesses that don’t require him day-to-day. Each time I’ve caught up with Branson he always reinforces the need to build businesses and projects that can operate with you needing to be involved. There is much leverage that can be gained by setting things up and employing great people to drive them forward.


What’s your favourite venue to take a date?


I’m such a casual kind of a person. Because I spend so much time in business I love a relaxed environment. A picnic on the beach or a glass of wine with cheese on the roof of my house, I guess anything that doesn’t require shoes is always going to tick the boxes.


What’s your ideal first date?


The date isn’t important, it’s about the conversation and the connection. I don’t do small talk very well so I generally figure out whether I connect with someone or not pretty quickly. Great conversation and a soul connection will get us lost in talking for hours and this is what lights me up.


Vote for Jack here:

About The Author

Lisa Hollinshead
Editor & Director

Boss lady over here at Social 101. Lover of all things that inspire creativity, individuality and happiness! Former party gal, now mama to a beautiful baby boy!

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