Friends With Money #279: The art of selling shares

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Investors spend plenty of time agonising over buying shares, but knowing when to sell can be just as crucial.

On this episode of the Friends With Money podcast, Money's Tom Watson is joined by Dale Gillham, chief investment analyst at Wealth Within.

They discuss the art of selling shares and the factors investors should consider before hitting the sell button.

friends with money podcast the art of selling shares featuring tom watson and dale gillham

Episode timestamps

00:00 Introduction

02:00 Why selling shares is harder than buying

08:00 The importance of having an exit strategy before you buy

13:00 Signs that it's time to sell up

16:00 Should you sell after big gains?

20:00 How tax should affect your selling decisions

22:40 Conclusion

Friends With Money podcast FAQ

What is the Friends With Money podcast?

Friends With Money is a weekly personal finance podcast by Money magazine, offering expert insights on investing, budgeting, superannuation, property, and other money strategies for everyday Australians.

Where can I listen to the podcast?

You can listen on Apple Podcasts, Spotify, or YouTube (with closed captions available).

Who hosts Friends With Money?

Episodes are hosted by Vanessa Walker and Tom Watson from Money magazine, featuring expert guests and real conversations about money.

Is the podcast suitable for beginners?

Yes! It's designed to be accessible for beginners while still offering valuable insights for seasoned investors.

What topics does the podcast cover?

The Friends With Money podcast covers topics including banking, property, budgeting, superannuation, investing, saving, insurance, employment, travel and more.

How often are new episodes released?

New episodes are released weekly, so you can stay up to date with the latest financial tips and trends.

Can I watch episodes with captions?

Yes, full episodes with closed captions are available on YouTube.

Why subscribe to the Friends With Money podcast?

Boost your financial literacy anytime, anywhere with the Friends With Money podcast from Money magazine. Whether you're commuting, working out, or relaxing at home, this weekly podcast makes it easy to grow your money knowledge on the go.

Each episode dives into real conversations about money - how it's earned, shared, saved, and grown - with tips and insights that make finance simple and relatable. Perfect for beginners and seasoned investors alike, it's your go-to guide for building better financial habits.

Subscribe to the Friends With Money podcast today and start learning when it suits you.

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Tom Watson is a senior journalist at Money magazine, which won three awards at the 2026 Mumbrella Publish Awards, and one of the hosts of the Friends With Money podcast. He's previously worked as a journalist covering everything from property and consumer banking to financial technology. Tom has a Bachelor of Communication (Journalism) from the University of Technology, Sydney. Connect with Tom Watson on LinkedIn.

Dale Gillham is chief investment analyst at Wealth Within Limited (AFSL 226347). He also serves as the head trainer at Wealth Within (RTO 21917). He has more than three decades of experience in the investment industry and is the author of How to Beat the Managed Funds by 20%. Dale's qualifications include an Advanced Diploma and a Diploma of Share Trading and Investment. He co-hosts the Talking Wealth Podcast, and his work has appeared in The Australian Financial Review, New York Business Journal, Wall Street Select and more. Connect with Dale Gillham on LinkedIn.