Balancing the Grind with Jack Delosa, Founder of The Entourage

Jack Delosa builds businesses. He is an entrepreneur, investor, media personality and the founder of Australia’s largest business coaching provider, The Entourage, with a global community of nearly 1,000,000 business owners.

Let’s start with your background! Can you share with us your career journey and what you’re currently up to? 

I’m someone that’s always been interested in human potential and my way of expressing that has been through building and investing in businesses that make an impact. I made a brief attempt at following a more traditional path by pursuing 

a commerce and law degree at university, but after three short months my eagerness to develop real-world skills overwhelmed my desire to have some letters after my name, and I dropped out to build my own projects. 

Instead of higher education, my apprenticeship came through starting businesses and learning from their success and failure. Some of them I loved, some of them I didn’t, but each one taught me something. Every success unlocked a new insight into how businesses are built, and every mistake etched into my mind the mistakes to avoid. 

In 2007 I co-founded a company called MBE Group, which laid the foundations that would later prepare me to start The Entourage. At MBE, helped business owners to raise money from investors and to build value to one day sell their business. We enabled our clients to execute over $300 million in transactions, and we became one of Australia’s fastest growing companies. 

Along the way, I invested in companies spanning the diverse worlds of biotechnology, finance, e-commerce, recruitment, and even aviation, including one that grew into what’s known as a “unicorn”; a business that goes from founding $0 to $1 billion within ten years. 

In 2010 I founded The Entourage to help business owners scale. Today, The Entourage is Australia’s leading growth agency and business coaching provider for 6, 7 and 8-figure business owners. We have a highly engaged community of nearly 1,000,000 entrepreneurs. Along the way we’ve generated over $6 billion in value for our clients who feature prominently on the lists of Australia’s fastest growing companies and most successful entrepreneurs. 

The work we do through The Entourage is what really lights me up. 

We’d love to know what a typical day is like for you. Could you describe a recent workday? 

No one working day at The Entourage is the same for me. Some days I might be presenting on stage to hundreds (or sometimes even thousands) of high-growth business owners, jetting off to a tropical destination for a retreat with our Members, interviewing an outstanding guest for my podcast, or knuckling down with an empty document ready to power through some deep strategy work. 

That’s why the journey of an entrepreneur is so rewarding – for the freedom it generates. I spend my days working on my “highest and best use,” and get involved in the business because I want to, not because I have to. The unfortunate reality though is that so many business owners never get to experience that freedom they set out for in the first place. 

That is the number one misconception about being an entrepreneur: people think it involves working in your business, but that couldn’t be further from the truth. Becoming an effective business owner means working on your business, and that’s the transformation we help our clients to go through. 

I’ve also recently become a new father to a beautiful baby girl, Ariella. Anyone who’s a parent knows how much this throws out a daily routine. Previously I would usually wake up and dive straight into deep work – my brain is definitely best in the early hours of the morning before the world is awake. 

Now I’m usually waking up with Ariella and letting her mum sleep in as much as possible. The rest of the day is a juggle as I try to be a present parent, a supportive partner, an entrepreneur, while trying to make time for the stuff that keeps me grounded like exercise and meditation. 

Can you define work-life balance for yourself and share with us your approach in maintaining it? 

The term “work-life balance” often sees work come off as the enemy. However, when what you do for work is fuelled by who you are, work doesn’t seem like work anymore. You find something greater than work-life balance: you achieve work-life harmony

Building something great – a business, a career, a family – is always going to require a huge amount of effort (and not just “hustle” or blind labour, these things are far too one-dimensional to enable somebody to do something truly special). It requires deep reflection, strategic thinking, intelligent actions and dependable leadership. Hard work is a very real part of building something great. That’s why it’s important you do what you love. 

Over the years, I’ve adopted and implemented what I like to call my “happiness strategies” – small, simple things that I do to help me reconnect with self. For me, it’s journaling, walking, being at the gym, being by the water, reading a great book, writing, meditating, and spending quality time with my family.

We all have them – it may be time with your kids, time away from your kids, cooking, eating, surfing, painting, gardening. Whatever they are, these are activities that make time stand still as we lose ourselves in the moment. This is joy. This is reconnecting. This is remembering what it means to be alive, and what it means just to “be.” 

Change is constant, and it’s essential for growth. Have you made any lifestyle changes in the past year to improve your work-life balance? 

A belief I subscribe to is that growth and comfort rarely coexist – if you’re comfortable, then you’re not growing. And, for many, change causes the greatest discomfort. But every single day, we get to consciously choose who we want to be and the life we want to create for ourselves. So once you accept that being challenged to a healthy degree can enable you to grow, you will find comfort in the discomfort you once wrestled with. 

Over the years, I’ve experimented with many different ways to optimise my personal performance and achieve work-life harmony, but I’ve often found that adopting the most basic habits have had the biggest impact. The biggest change I have made in the past year is that I don’t schedule my happiness strategies anymore (this includes journaling, meditating and training). I’ve ritualised them.

For instance, you won’t find journalising in my calendar. Generally speaking, I do them often and automatically when I feel the urge, because they are the very simple things that give me joy, and keep me connected. It’s these things that keep me showing up the best for others in my life. 

We’re always on the lookout for new resources! Can you recommend any books, podcasts, or newsletters that have helped you in your journey towards balance? 

Some of my favourite books that have influenced me on my journey include Think and Grow Rich by Napoleon Hill, What I Know For Sure by Oprah Winfrey, Principles by Ray Dalio, and A New Earth by Eckhart Tolle. I’ve also written 3 best-selling books including Unprofessional Unwritten, and most recently Elevate: How To Accelerate Growth And Scale Your Business Beyond You. I’d recommend these to anyone who wants to achieve extraordinary things, and do it in a balanced and meaningful way. 

I’ve also spoken with many incredible human being across the world including Steve Wozniak (Apple), Gary Vaynerchuk, and Marie Forleo on my podcast Elevate With Jack Delosa. This is for anyone who wants to learn from some of the most successful people in the world about everything from business, to life, and finding true harmony between the both. 

Before we wrap up, do you have any final words of wisdom or insights on work, life, or balance that you’d like to share with our readers? 

I’ll leave you with this: when you are engaged in the work, be fully engaged. When you are not, do your best to fully disengage. 

I learnt this lesson the hard way when I reached a point of being absolutely burnt out in September 2015. I woke up one day, but I physically could not get out of bed. I had just come off an international tour for one of our signature events at The Entourage, and I found myself incapable of simply standing up. And for the next year and a half, I changed very little.

I continued to get little sleep, eat poorly, exercise rarely and grind through. Because the business side of things had become even more demanding, if anything my habits had become more unhealthy which meant that for 18 months I was running on 20%. 

With the high demands of the culture we live in, it’s easy to think that living in an unhealthy and unbalanced state is normal. One could be forgiven for thinking that not sleeping well, waking up tired, pushing through stress, energy dips, craving sugar, food, coffee, wine or whatever it might be, is normal. But it isn’t. These are all symptoms of a lack of wellbeing – and they can be fixed. 

On reflection, it’s clear to me that this chapter of my life and career was fuelled, like so many of us are, off pure will-power. But I’ve learnt that in order to continually climb the next mountain, I wasn’t going to do it by repeatedly getting more out of myself. I had to learn to invest more wisely in myself

So I’ve learnt that we’re better when we’re rested. Chances are, if you’re reading the interviews on this website, a lot of people rely on you for your leadership. And so much of being a great leader is about creating work-life harmony so that you can not only do your life’s best work, but be an example to others who want to do the same. 

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.