474 | From Childhood Stocks to City Shocks: How He Escaped Bad Investing Advice! – Chat with Bailey


It’s our final episode for the year and folks, we’ve saved one absolutely inspirational tale to finish 2023.   

As a hint of what’s to come, Bailey – today’s articulate Summer Series guest – invested $500 into Westpac shares at the age of 10.  

While this one action already sets him aside, Bailey isn’t special just because of his remarkable approach to investing but because of one skill that, as described by Ben, is “one of the greatest skills to learn in life”.  

If that isn’t a cliffhanger folks, then we don’t know what is. 😉  

Tune into this fascinating episode to find out what sets this 24-year-old apart from the rest, how he bought his first property at the young age of 21 and to hear the heart-warming reason why he decided to speak out and come onto the couch.  

This guest has Ben and Bryce completely rapt. Seriously, give it a listen now folks 😊🌌✨ 


Free Stuff Mentioned



  • 0:00 – From Childhood Stocks to City Shocks: How He Escaped Bad Investing Advice! 
  • 1:38 – Welcome Bailey!  
  • 2:21 – Growing up with a money-savvy mum  
  • 6:47 – How he started on his financial future from 10 years old!  
  • 10:39 – What sparked his love for investing?  
  • 12:16 – Bailey’s lifehack while his friends were at university  
  • 15:12 – What he did with all his savings 😲 
  • 17:41 – THIS is one of the biggest lessons in life…  
  • 21:03 – How did it feel when he bought his first property (You’d be surprised by his answer😉) 
  • 25:38 – He’s now stopping and smelling the roses – here’s how!  
  • 27:35 – Bailey’s paradigm shift  
  • 31:05 – Beware the enthusiastic amateur!  
  • 35:15 – These were the biggest lessons he learnt…  
  • 37:26 – Why it was actually good that he had a bad experience!
  • 41:14 – His pathway to becoming borderless!  
  • 43:19 – Why is rent-vesting right for him?  
  • 46:28 – Bailey’s North Star ⭐  
  • 50:32 – What drove him to speak on the couch?  
  • 51:39 – The secret to goal setting  
  • 55:11 – How he’s navigating two extreme interest rate environments 
  • 58:21 – Thank you Bailey! What an articulate and inspirational person 😊  
  • 1:01:25 – Here’s a challenge to Bailey’s mates 



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