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Dream Out Loud

352. From School Expulsion to $50M+ Portfolio: Jack Henderson’s No-Excuses Playbook

14 Oct 2025

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In this episode I sit down with Jack Henderson, one of Australia’s youngest and most successful property investors, to unpack the truth about building wealth, dealing with hate, and doing what you love. Jack keeps it raw, breaking down why most people shouldn’t start a business, how to think like the wealthy, and why tall poppy syndrome never stops.⊳Join my Free Skool Community: Connect with entrepreneurs committed to rewiring their identity, building unstoppable confidence, and scaling businesses that create true freedom.https://www.skool.com/dream-out-loud/about?ref=b30af20dcf024f8f9eaf71bd232e6311Episode Timestamp 00:00 - Introduction01:00 - Picking the Right Industry For Money01:45 - Life At School 03:26 - Success is different for everyone06:14 - 2 Beliefs you need for success09:38 - Not wanting to vote 14:32 - Focus on what you can control16:43 - Dealing with Tall Poppy Syndrome21:12 - Buying property at 18 24:25 - Why invest in property28:54 - Australia using outdated metrics31:12 - The rise of Gold Coast Pricing34:10 - How to start in property 36:57 - Biggest Myth Buying Property39:29 - How the rich get richer 39:50 - Why you shouldn’t start a business 41:35 - The exact strategy Jack uses45:07 - What property Jack is buying 49:17 - Property bubble in Australia 53:56 - What Jack would do differently if he was 18 again55:05 - Why use a Buyers Agent 57:25 - Life Advice for his younger self

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