Ep 331: Should you Sell Property in 2026 or Hold Long Term? - with Steve Ash & Todd Sloan

Feb 14, 2026

Steve Ash, property investor and founder of Property Strats with a background in investment banking and analytics. They contrast short-term trading with long-term property investing. They unpack why trading seems attractive, why most traders lose, and how market cycles and compounding quietly build wealth. A real Western Sydney case study and practical steps for scaling with equity are discussed.

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INSIGHT

Trading Is Sexy, Investing Is Reliable

Trading is exciting but most traders lose money, so it rarely outperforms long-term investing.
Steve Ash warns that only a tiny fraction of day traders consistently profit, making time-in-market powerful.

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ADVICE

Don't Try To Time The Market

Stay fully invested because missing a few top market days drastically cuts long-term returns.
Do not try to time the market; compounding and time in the market drive results.

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ADVICE

Prepare For Black Swan Events

Prepare for black swan events by buying quality assets and keeping cash buffers.
Manage cashflow so you can hold through downturns instead of being forced to sell at lows.

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Defining trading versus investing

01:49 • 4min

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Why trading looks attractive now

05:24 • 1min

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How few traders actually win

06:32 • 9min

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Time in market beats timing

Preparing for black swans

17:40 • 3min

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Managing cashflow and location risk

20:30 • 5min

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Where value appears during downturns

25:59 • 5min

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A long-term Sydney case study

31:19 • 7min

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Sell now vs equity extraction math

37:53 • 4min

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Compounding with equity to scale

41:43 • 3min

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Time and compounding beat higher returns

44:42 • 8min

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Practical action steps

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This book is a classic in the realm of stock market literature, detailing the life and trading experiences of Jesse Livermore, a legendary trader, under the pseudonym 'Larry Livingston'. It explores Livermore's journey from his early days in 'bucket shops' to becoming a prominent figure on Wall Street. The book highlights the importance of understanding market psychology, the dangers of overtrading, and the need for discipline and independent analysis in trading. Despite being written nearly a century ago, its lessons on market dynamics and human nature remain relevant today.

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In 'The Psychology of Money,' Morgan Housel delves into the psychological and emotional aspects of financial decisions. The book consists of 19 short stories that illustrate how personal history, worldview, emotions, and biases influence financial outcomes. Housel emphasizes the importance of behavior over knowledge in managing money, highlighting the power of compounding, the dangers of greed, and the pursuit of happiness beyond mere wealth accumulation. He advocates for a frugal lifestyle, long-term perspective, and a balanced approach to investing, stressing that financial success is more about mindset and discipline than about technical financial knowledge.

Should you Sell Property in 2026 or Hold Long Term?

Is trading really the fast track to wealth, or is long term investing still the smarter play? In this episode, Todd Sloan sits down with Steve Ash, founder of Property Strats, to unpack the fine line between trading and investing and why so many people fall into the trap of confusing the two.

They explore why so many traders lose money, how speculation in crypto and property fuels short term thinking, and why market cycles quietly do the heavy lifting over time. It's a grounded look at what actually builds wealth versus what just feels exciting in the moment.

Using a real property example from Western Sydney, Todd and Steve show the power of staying invested, holding through cycles and using equity the right way. If you're focused on long-term results, this episode will reshape how you think about investing.

🍕🏠 We want to hear your investor story! So if you've experienced something that you know other investors can learn a thing or two from, click the link below and let us know. 🍕🏠 👉 https://pizzaandproperty.com.au/investor-story 👈

Get in touch with our amazing episode contributors & sponsors:

Chat with Steve Ash today: 👉👉https://www.propertystrats.com.au/

Rob Flux: https://developernetwork.com.au/events

InvestorKit: https://www.investorkit.com.au/

If you'd like to be flown into the Pizza & Property Studio, put up for a night's accommodation, have dinner with Todd Sloan, and have a team of carefully chosen property investing experts help you get unstuck, click the link below and tell us why you're stuck, and you could be our next UN-Stuck Yourself winner! 👉 https://pizzaandproperty.com.au/unstuck-yourself 👈

Want more help understanding how to buy property faster and for less? Get your copy of Todd Sloan's book today:

Booktopia: https://www.booktopia.com.au/australia-s-home-buying-guide-todd-sloan/book/9780648980490.html?source=pla&zsrc=go-nz-allstock&gclid=Cj0KCQjwnJaKBhDgARIsAHmvz6f55Kw-l0pKCn0DMNj0TND2qN863sQQR56p98sXAjOUgBQSpwDDQ0waAtLsEALw_wcB

Dymocks: https://www.dymocks.com.au/book/australias-home-buying-guide-by-todd-sloan-9780648980490?gclid=Cj0KCQjwnJaKBhDgARIsAHmvz6etuq25nQ2CSirN8z-UHAIshbp5MxeuD7ECMvs5Oghg2Pab34Fyl0QaAuQhEALw_wcB

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