Dump or Double Down? Knowing When to Sell Your Underperforming Investment | Stuart Wemyss

In today’s podcast, Stuart Wemyss and I discuss the complexities of managing underperforming property investments, and how to decide when and if you should sell your property . 

We explore everything from the emotional traps that can cloud our judgment to strategic considerations like tax implications and portfolio rebalancing. 

Takeaways 

• Investing is a long-term journey, often taking decades to develop financial independence. 
• The quality of your asset is crucial for long-term returns. 
• Benchmarking performance relative to market conditions is essential. 
• Market cycles can significantly affect property values. 
• Recognising a poor investment is a brave but necessary step  
• Emotional decisions can cloud your judgment 
• Patience is key; sometimes waiting is the best strategy. 
• Tax implications should be considered when selling assets. 
• Holistic financial advice can optimise investment strategies. 
• Replacement assets can provide a strategic way to manage underperforming investments. 
• If you find yourself digging a hole, stop. 
• Sometimes the right thing to do is nothing. 

Chapters 

01:06 Understanding Underperforming Investments 

10:42 The Importance of Patience in Investing 

20:19 Evaluating Investment Decisions and Timing 

28:09 Holistic Investment Strategies and Seeking Advice 

28:14 Introduction to Wealth Retreat 2025 

29:44 The Importance of Quick Decision Making in Property Investment 

31:26 The Long Journey to Wealth 

32:51 Building a Legacy of Wealth 

33:38 Understanding Market Trends and Analysis 

 

Links and Resources:  

   

Michael Yardney 

Stuart Wemyss – Prosolution Private Clients 

  

Stuart’s Book – Rules of the Lending Game & Investopoly 

  

Get the team at Metropole to help build your personal Strategic Property Plan Click here and have a chat with us 

  

Join us at Wealth Retreat - Australia’s Premier Wealth Retreat for Elite Investors and Business People www.WealthRetreat.com.au  

  

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Also, please subscribe to my other podcast Demographics Decoded with Simon Kuestenmacher – just look for Demographics Decoded wherever you are listening to this podcast and subscribe so each week we can unveil the trends shaping your future.