Jack Delosa: “A Loveable Rogue”

- January 11, 2013 6 MIN READ

He was described throughout his school life as a “loveable rogue” on his report cards, someone who upon application of themselves produced results, but just generally didn’t like the school system. He now runs an education company with a vision of reaching 500 million dollars in valuation by 2023. In this interview with Jack Delosa, we go beyond the fluff and media hype of mainstream media, steer away from the “startup advice” type rhetoric often found in interviews with business builders, and we look at the reasons he is where he is today, the challenges he went through to get there and why only two years ago he flirted with the idea of packing in The Entourage and starting a real business. 

I have met Jack Delosa many times before, I have interviewed him, brainstormed with him and have started to see a close business friendship develop between our companies. I have never before though, gone beyond the pleasantries, really dug deep and asked the questions that I have asked in this interview however. There was a point around 6 minutes into the conversation when the Jack that I see on the likes of Sunrise went away and I was taken on a journey back to those early teenage years, the period of time that tested him the most and shaped who he is today.

Jack’s parents founded and ran a very successful not for profit business Breaking the Cycle, when he was younger. A business that focused on taking youth off the streets, rehabilitating them, training them and acting as a job placement agency finding them work and setting them up for a better life. The business was successful with around 3 million dollars annually in revenue, it was also heavily funded by the government. As a young boy Jack saw first hand the impact of what his parents did and how it helped individuals change their lives, even having two youth, that had overcome their drug addictions living with the family, becoming like siblings to Jack and his brother Tom.

After a change of government, who consequently pulled the funding from the company, the business crumbled, a lesson that he now says taught him a lot about corporate structure and the way things needed to work to have a successful business. Over his time at school he says there were two particular teachers that taught him very valuable lessons, he also says he wouldn’t be where he is today if it was not for them. His grade 3 teacher that taught him about honesty, responsibility and consequence in a way that she was always on his side, but was extremely tough. The other was his year 11 teacher, that, even though he was probably the biggest rat bag out of his whole year level, saw something in him, that admittedly he never yet saw in himself – she put him up for the role of prefect. The other teachers however put a stop to this, and it wasn’t to be.

It is easy to see why Jack developed a dislike for traditional education, the rules of conformity at schools [especially private schools] is a recipe designed specifically to denounce individuality and out of the box thinking, I remember myself on a school excursion once I got in trouble for wearing a bright yellow tie [it was casual dress] because it sent out the wrong message and was highly inappropriate, in other words I looked like a big homo. That’s the problem with traditional schooling, it is only ever fun for the status quo and those who have boring dreams.

Jack did go on however to achieve a pretty good score in his VCE and went to university, to study Law and Commerce. This lasted three months, a life changing sequence of events then occurred. On the Thursday Jack quit his university degree, his brother Tom passed away on the Friday and the new venture he partnered with two other young entrepreneurs to build started on the Monday. I paused for a second at this point of the interview, as I needed to make sure I heard him correctly. Which then lead me to ask how he was able to mentally do that.

Jack told me that Tom was the closest person to him in the entire world, they both were borderline identical, sharing the same addictive, rebellious, don’t give a fuck attitude. He tells me that when it happened he went completely numb, that physically, spiritually and mentally he shut down, almost not acknowledging it and continued to build the business he had bought into. It was a couple of weeks later that he told his parents that he had left university.

The next 6 months were stressful, he had borrowed $20,000 from a bank and there were four different business units, all of the business units were losing money, and there were times where certain relationships were strained. At points everything looked terrible and very scary, however after one of the partners in the business had moved on due to ongoing issues, the business began to make money and slowly got itself out of trouble. He recalls this as being a very stressful introduction to business, but one of the periods of time where he learnt the most lessons.

Like many of us, Jack went into business with a very romantic notion of what it was to be an entrepreneur, driving around in BMW’s and Lexus’ / partying and living the wild lifestyle, he thought life was great and no idea about the importance of the bottom line. As he says though, that mistake catches up with you very quickly and when you are in a dire situation, that is when your focus is forcibly pulled towards it.

Grieving for Tom’s death came around the same time things started to turn around for the business, I want to quote this part word for word as it was quite a touching moment that Jack has not really spoken about often before:

“I have never really spoken about this, [the moment of that emotional release] it was fucking weird, I was driving home, in my Lexus – at the age of 19 and was stopped at a red light, and just started … burst out crying and I didn’t know why. I was so young and I didn’t know how to grieve yet. i think what that gives you, is personal strength, I believe that character is built through adversity – pressure is how diamonds are formed. So although you never want to go through something like that, or wish that other people go through that, it is often the hardest events in your life that will end up being the most rewarding, if you choose to look at it that way.”

There are words of wisdom in that beyond someone that is still in their early twenties. It is very clear to me that his philosophy is that life is precious and you need to make it count, out of which an obsession with business and education was formed – where many others in the same situation could make a very different choice and head down an equally obsessive, yet more destructive path.

I ask Jack if entrepreneurship is his vice, is this his addiction in life. He reflects for a moment and then answers yes. He says that he is addicted to the fight, that it’s the constant ongoing challenge that feeds him and fulfils him. We then come to – Why The Entourage? How did it all begin?

For Jack, The Entourage was 23 years in the making, 12 months prior to starting he was having an argument with himself and had two different mentors both representing the head and heart, giving him two conflicting pieces of advice. The head told him that the market for educating young entrepreneurs had no money in it, that he was good at doing commercial deals and he could make a lot of money from that. The heart mentor said he should follow his passion, that he was not going into the business to make money, but that money would follow. In the end the heart got the better of him, and he started it driven by the same dissatisfaction he felt when he was 9 years old and his parents had to shut down Breaking the Cycle. He wanted to make a real difference in the education space for Gen Y.

The first 6 months were quite good, it was new, people partnered with them and it was an exciting time. Then from the 6 month to 18 month mark, things stagnated and hit a plateau, there were moments during this period of time when Jack would flirt with the idea of going and starting a real business. I ask if at the time he thought The Entourage was a real business, he answers no and describes it as a passion business at that point. Those twelve months were testing, and everyday felt like challenges were being thrown at him.

At this point I reflect on the last 12 months in our business, interestingly enough this was also our 6-18 month period of Shoe String Media. In talking about these moments, I talk about the fact I had too many ideas, and was trying to do too many things which was the biggest cost to me.

Jack agrees that lack of focus is the number one killer to any startup business, in his business this year he is focusing on one thing only – education. Interestingly enough this precise focus is geared to generate them more revenue than previous years, as they head towards the goal of becoming a 500 million dollar education company by 2023. The revenue stream in the business that brings about the most revenue for The Entourage / MBE is the education part of the business, teamed and helped along with corporate partners, that allow the Gen Y community to access these courses. In a move that will undoubtedly put them ahead of the pack they will be working with major stakeholders in developing nationally recognised courses and begin to slowly change the way education is perceived.

Jack Delosa is addicted to furthering himself through education and mentorship, we often hear that wealth changes people, however as he eloquently puts it, wealth acts as a magnifier of what is already there, for example a rich arsehole was probably an arsehole before they came into money. I see when I look at Jack someone driven, a change maker and a humble, yet loveable rogue.