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Chew the Fat

How to Get Rich in 2025! $25M Property Portfolio vs $560M Startup - Real Estate or Business? Jack Henderson vs Charlie Gearside Debate!

04 Aug 2025

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This is an emergency debate on the best way to get rich in 2025... real estate or business? $25M+ property portfolio owner vs the $560M co-founder of Eucalyptus went head to head.Jack Henderson built a $25M+ property portfolio by the age of 27 and now runs a 120 employee property buyers agency. Charlie Gearside co-founded Eucalyptus, a healthtech company valued at over $560M. Both have made a lot of money, but they disagree with the method to get rich in 2025.In this episode of Chew the Fat, Jack and Charlie go head-to-head on: - Why most people suck at business (and should stick to houses) - Why property is making Australia dumber - The reason our tax system punishes entrepreneurs - And what actually holds people back: mortgages, culture, or fearThis is the real conversation about wealth, risk, and what Australia needs moving forward.

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