Bothsides Podcast28 Syys 2025

EP 132 | Jack Delosa: $100M Portfolio, Founder of The Entourage

What if the No.1 reason you’ve never achieved your goals has nothing to do with talent, luck, or resources… but the way your mind retreats when things get hard?

Entrepreneur, investor, and founder Jack Delosa has spent two decades building, scaling, and rescuing companies worth hundreds of millions. He’s been $25M up, $5M down, and rebuilt again. Now, he’s revealing the real reasons most people never succeed - and the simple frameworks you can use to finally break through excuses, fear, and overwhelm.

With brutal honesty and hard-won experience, Jack exposes the uncomfortable truths about why people quit, how to stop self-sabotage, and what it actually takes to achieve big goals in today’s world.

Jack is the founder of The Entourage, Australia’s largest training institution for entrepreneurs, and an active investor with over $100M in portfolio value. He’s been featured in BRW Young Rich List multiple times and is the author of two best-selling business books.

In this conversation, Jack reveals:

◼️ The No.1 reason people never achieve their goals (and how to beat it).

◼️ Why your brain’s natural instinct is to retreat into excuses when things get tough.

◼️ The 2-hour rule that can transform your business and life in weeks.

◼️ How to identify and fix the real constraint that’s holding back your success.

◼️ Why most entrepreneurs are trapped in busywork instead of growth work.

◼️ The hidden danger of operational debt and how to reverse it fast.

◼️ Why leaning into AI now can be your biggest advantage in the next 5–7 years.

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Thank you so much for listening!

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