I Built A Coaching Business That's Helped Over 40K Founders
I’m Jack Delosa: entrepreneur, investor, 2X best-selling author, 5X AFR Young Rich Lister, and Founder of The Entourage, Australia’s largest business coaching and training provider for entrepreneurs. The Entourage has transformed over 3,500 businesses in more than 150 industries and has helped entrepreneurs add over $2 billion in value to their businesses.
At The Entourage, we fundamentally believe that building a business is a skill that can be developed - and we can teach it. We offer business coaching and training completely tailored to our Members and the stage of business they’re at, and where they want to go. The Entourage’s Accelerate Program is for business owners who want to accelerate their growth from 6 to 7 figures, and Elevate is Australia’s only business coaching program exclusively for 7 and 8-figure founders. Alongside some of the country’s best entrepreneurs, we also host Australia’s largest events for business owners, including Unconvention, which has been voted in the top 3 events for entrepreneurs and business owners worldwide, by Entrepreneur.com
What's your backstory and how did you get into entrepreneurship?
My tap on the shoulder came when I was only 5 years old. My parents started a not-for-profit organization called Breaking The Cycle, which took long-term unemployed youth off the streets and put them through a training program that ultimately resulted in meaningful employment. Because only a finite number of kids could be seen each year, Breaking The Cycle chose the most challenged people - but it would go on to place 97% of its kids into employment, with 85% still meaningfully employed after 12 months. It was the most successful job-placement agency for long-term unemployed youth in Australia. Breaking The Cycle was a big part of my family’s life, but in 1995 the federal government shut down the Commonwealth Employment Services department, re-engineering how NFPs would access capital. As a result, Breaking The Cycle was no longer able to access the funding upon which it depended.
I learned 2 major things from Breaking The Cycle. The first was about education, and the second was about money. It showed me that the educational system fails a lot of us, and a conventional career path doesn’t work for everyone. As such, I became dissatisfied with the conventional path that traditional education sets us up for. It drove me to start doing my research at the age of 14; it prompted me to find a new path - one that worked for me. The more I researched individuals and ideas that changed the course of history, the more I observed that those who had truly influenced the world were not politicians; they were inventors and innovators, they were entrepreneurs.
The second lesson that Breaking The Cycle taught me was that money, or the lack of it, starkly limits what you can achieve. My father told me something that struck a chord after Breaking The Cycle ended. He said, “You can’t run off love, trust, and pixie dust.” Even if you are in the business of making a difference, if you want your vision to travel, money is the fuel that will allow it to do so. I understood that to contribute to the field of education, I would need to become somebody who could take ideas and make them real. And for that reason alone, I started my first business.
Take us through your entrepreneurial journey. How did you go from day 1 to today?
My “apprenticeship period,” running my own business with little knowledge of what I was doing, spanned the same amount of time that a university degree would have, and I spent the first 4 years of my business career making 0 visible progress. I was going backward, borrowing money I couldn’t afford, and working completely around the clock. It was an incredibly discouraging introduction to business, yet, while there was zero visible progress, there was progress in the one thing that underpins anyone’s success in life - one’s self.
It was the failure of my first few years in business that ultimately gave me the lessons to later co-found a company called MBE Education. By utilizing experienced advisors, MBE would enable small and medium-sized enterprises to raise money from investors, and acquire and exit businesses. We quickly became one of Australia’s fastest-growing companies, giving me the financial foundation and the credibility to return to my childhood dream of bringing innovation to education and training.
In 2010, I founded The Entourage, a business coaching and training company for entrepreneurs and small business owners. I set out to build a style of training that not only equips business owners and entrepreneurs with the practical skills and tools required to be successful in tomorrow’s world but also focuses on the individual’s personal growth. Today, we are Australia’s largest and most effective business coaching and training provider and community for small business owners, with a community of over 500,000 people, and a list of Members and Alumni who pepper the list of Australia’s fastest-growing companies and most successful entrepreneurs.
But this certainly hasn’t come without a unique set of challenges. In 2016, at the height of The Entourage’s success, government changes were introduced to the education space in Australia. The result was that we were 3 months away from a monthly loss of $800,000 and we had no business model or product suite that would exist beyond that period. This was the most challenging period of my life and career, and certainly the most challenging time in the history of The Entourage. Overnight, we had to take our team of 90 and turn it into a team of 40, which was incredibly heartbreaking, and work on developing a new product suite that was both commercially viable and something our community wanted.
But from that experience, we emerged stronger than ever. 18 months after the Government changes, our community had grown larger than ever, our Members were getting better results, we were more profitable and growing faster than we ever had. Ultimately, like all times of great challenge, we came out of it wiser than ever, with the hard-won lessons to help guide our community through the challenges they would ultimately face in their business journeys - because there is no shortage of challenges that business owners face. Whether it’s a global financial crisis or pandemic, a change in government regulation, a big competitor entering the market, or a large mistake we make as we grow, working through challenges is part of the game.
How are you doing today and what does the future look like?
Today, The Entourage is in its most commanding position ever. We are Australia’s leading business coaching and training provider and community for ambitious entrepreneurs. Since 2010, The Entourage has helped transform more than 3,500 businesses in over 150 unique industries and generated more than $2 billion in revenue for our Members. We are delivering world-class support to our Members in this uncertain period, starting to develop some of the world’s best online courses alongside some of Australia’s leading entrepreneurs, and scaling our marketing engine to drive measured international growth.
Over the next 5 years, business owners around the world will go on the same journey we have been on since 2016 - rebuilding and refocusing after incredible adversities that have threatened the viability of their businesses, and we will be there to help them. We’ve worked the past 5 years to do what’s about to happen, and I’m incredibly excited to show more of Australia and the world what The Entourage has to offer.
In June 2020, I exited the CEO seat and the day-to-day operations of the business. It has always been in my DNA to build businesses that can operate and scale without me being operationally involved. The best entrepreneurs invest in and build businesses that do not rely on them. That is what we teach our Members and community to do.
As the Founder, Chairman, and Executive Director (and the figurehead of The Entourage brand), I am still heavily involved in developing the annual curriculum for our Members, our business coaching and training methodology, and sharing our vision with the market by participating in a range of speaking engagements. I’m actively and regularly exploring new market opportunities, investing in other businesses that share similar visions (to empower small business owners), and am writing my third book (set to be released in 2022) which will go into more detail on how The Entourage came through the challenges of 2016 and the business lessons we learn to elevate back to the 8-figure mark.
Through starting the business, have you learned anything particularly helpful or advantageous?
Having built businesses that have reached 8 figures, and invested in businesses that have reached 8, 9, and even 10 figures too, there are some core strategies, mindsets, and lessons I’ve learned that can help anyone scale a company to 8-figures and beyond.
Decide on what capabilities you need to start building in yourself and your team and know that you absolutely can. You can do whatever you choose.
One of the biggest ones is that each stage of business requires different management, leadership, and even focus. What does that mean? That means that at $0-$100K in revenue, we need to be improvising, interacting with our consumers, making it up as we go along, and not having so much of a set plan in place because things will be changing so frequently. From $100K to $1M, we need to focus on sales and marketing, getting those processes right, but often to the detriment of operational perfection and excellence. However, when we get to $1M+, that’s when we can start putting in those systems, processes, strategies, and operational planning. This means that in the beginning, don’t worry too much about being perfect. Test things, see what works, and keep pivoting where the market is telling you to go. Then as the business evolves and matures, your management and leadership style can evolve with it too.
Another major lesson for business owners who are starting to grow is understanding that all business owners can wear several four ‘hats’ in terms of their responsibilities and where they sit in the organization. You start in business wearing the hat of a technician - you have your hands on the tools. Then as your team starts growing, you wear the hat of a manager - the person managing the people with their hands on the tools and often contributing to it too. This next step is hard for many to step up to as it means trusting in your team to do what’s needed - the hat of the leader where you focus more on the overall culture of the business, focusing on motivation, communication, care within your team, and less about the doing.
And the last hat is one we should all aim to get to - the hat of the entrepreneur. Entrepreneurs build assets that operate without us, guiding the organization from a long-term vision standpoint, strategizing, envisaging, and building it to get there. We cannot stay technicians or managers for our entire business journey although we can dip our toes back in it here and there. We need to become entrepreneurs and set that long-term vision if we truly want our business to get to that next level.
What platform/tools do you use for your business?
At The Entourage, our two main platforms/tools are Hubspot and ClickUp. Hubspot is our Customer Relationship Management (CRM) platform that not only hosts our website but also helps us manage our deals, workflows, marketing campaigns, and so much more. It’s an all-inclusive platform that has helped us have more transparency in our customers’ journey with us and made a lot of systems and processes in our team a lot smoother. They also have a Hubspot Academy that helps our team upskill in their departments too.
ClickUp on the other hand is our favorite productivity platform. We’re able to manage all of our team tasks, goals, and projects all in one place - everything from event management to social media calendars. We’re able to easily see what each team member has assigned and on their plate as well as the progress of our major projects too. With all of these functions in one place, we don’t need to swap between different platforms to view projects.
What have been the most influential books, podcasts, or other resources?
Some of my favorite 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 2 best-selling books including ‘Unprofessional: How a 26-year-old University Dropout Became a Self-made Millionaire’ and ‘Unwritten: Reinvent Tomorrow’ that I would recommend to anyone who doesn’t want to be part of the norm, who wants to stand out, and who wants to live an unconventional life and achieve extraordinary things.
I’ve also spoken with many incredible human beings across the world including Steve Wozniak (Apple), Gary Vaynerchuk, and Marie Forleo on my podcast The Jack Delosa Podcast where you can learn from myself and some of the most successful people in the world about everything from business to life. If you want to hear more business stories, strategies and lessons, check out The Entourage’s The Make It Happen Show podcast which has featured some of Australia’s top entrepreneurs such as Ronni Kahn AO (OzHarvest), Tobi Pearce (Sweat), Samantha Wills (Samantha Wills Jewellery), and Janine Allis (Boost Juice).
Advice for other entrepreneurs who want to get started or are just starting out?
The #1 principle that I teach to all our Members at The Entourage and any business owner or entrepreneur I connect with is this. You can. You can do this. You can build a business to any size that you choose. You just need to be someone who’s always learning, who’s accepting of the fact that you’ll probably need to change tact multiple times, who’s okay with people who are going to come and go, who’s ready to take two steps forward, and one step back, and someone who is ready to not always be linear on their business journey.
If you’re capable, you’ve got grit, and you keep learning and adapting, changes are in 10, 15, or 20 years, you’ll get to that million-dollar, hundred million dollar business. You just need to ensure that you continue building on the characteristics required to get you there. And also just choose to play this game at the level you want to be at. Remember, everything is a skill. Building a business is a skill. Building a 6, 7, 8, 9, or 10-figure business is a skill. And if you haven't done that before, that just means you haven’t yet developed the capabilities to get there yet, but don’t stop learning, ‘cause you will one day get to those capabilities.
Just know that whatever scale you choose to get to, you can grow into the characteristics needed to become the human you want to become. Just decide and know that you may raise the bar, sometimes bring back the bar too, but just decide. Decide on what you need to become to build it. Decide on what capabilities you need to start building in yourself and your team and know that you absolutely can. You can do whatever you choose.
Where can we go to learn more?
If you want to learn more about my journey and what we do at The Entourage to help business owners succeed and make their mark on the world, feel free to visit us on our website and subscribe to our newsletter where I and my team send weekly resources that are made to help businesses grow. You can also message me (@jackdelosa) or my team at The Entourage (@theentourageofficial) on any social media to talk more.
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Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
Download the report and join our email newsletter packed with business ideas and money-making opportunities, backed by real-life case studies.
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