The Dylan Mullan Show (previously Life, Money & Love) $100M CEO: Hard Now, Easy Later – The Simple Formula That Separates Successful Entrepreneurs From Everyone Else (Entrepreneur Reality Check)
In this episode, I sat sit down with Jack Delosa - a self-made entrepreneur, bestselling author, and founder of The Entourage, Australia’s largest business coaching and training platform.
Jack built a $100M business by doing everything the system told him not to. He didn’t follow the rules… he rewrote them. And in this raw and powerful conversation, he shares the truth about school, success, and what it really takes to win in today’s world.
From challenging the outdated education system to revealing why he’ll never send his kids to a traditional school, Jack breaks down how the system is setting people up to fail - and what you can do about it. He talks about growing up around teachers, studying education since he was six, and how it all led him to the shocking discovery: school was designed for factory workers… not future leaders.
We go deep into homeschooling, woke culture, capitalism, and why young people feel like they’ve been lied to. Jack opens up about what’s really going on in schools today and how it’s affecting your children’s future. But this isn’t just about the problems - Jack also shares how to take back control, raise free-thinking kids, and build a life of financial freedom through entrepreneurship and personal responsibility.
If you’ve ever felt like the system wasn’t made for you… this episode will change how you see the world.
In this episode:
- Why Jack Delosa will never send his kids to school – and the radical approach he’s taking instead to prepare them for a world school isn’t built for.
- The real reason schools were invented and how they’re still training kids for a world that no longer exists.
- Jack’s harsh take on the education system and why he believes it’s not just outdated — it’s actively harming your child’s future.
- The rise of homeschooling and why more parents from all walks of life are choosing freedom over conformity.
- The scary truth about woke ideology in schools and the moment Jack realised it was time to opt out completely.
- Why capitalism isn’t the villain and how Jack reframes the money conversation for young people who feel left behind.
- How school debt, underemployment, and rising house prices are fuelling distrust in the system — and what to do instead.
- The shocking stats behind graduate underemployment and why Jack believes your degree may be holding you back.
- How Jack built a $100M business by doing the opposite of what school taught him — and how you can too.
- Why personal responsibility is the only way forward and how to create real freedom through entrepreneurship.
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