In this episode of Talking Trading, Louise Bedford sits down with author and investor Heather Cullen to unpack the biggest lessons from her 25 years in the markets.
Heather has seen it all – the wins, the gut-wrenching losses, and the slow realisation that ‘complicated’ doesn’t mean ‘better’ and working more hours does not equate to more profits. Quite the reverse!
Pls note: Heather meant to say the 10 / 200 EMA cross in the video. Not the 10 / 20 cross.
Her strategy is simple, but goes against many market myths. The first being ‘it’s time in the market, not timing the market’, and ‘buy and hold’ is the best strategy.
She shows how a very simple system beats ‘buy and hold’ by over 50%. Another myth: ‘options are risky’ – she proves her simple ITM options strategy has beaten the market tenfold over the last 30 years.
In trading there are losses – no one can avoid them. The secret is to ensure that your wins are significantly larger than your losses. When the market is going up, ITM more than doubles the market return, and when it is going down, we are safely waiting on the sidelines.
We also explore the rise of AI in trading – where it genuinely helps, where it’s pure hype, and the dangers of outsourcing your decision-making to an algorithm.
If you’ve ever wondered how to trade smarter, avoid costly mistakes, and future-proof your edge, this candid conversation will be your blueprint.
You’ll learn:
- When market timing works – and when it backfires.
- How to look past the myths and focus on what works.
- What AI can (and can’t) do for everyday traders.
Questions we discuss
- Heather, you’ve been trading for 25 years – can you take us back to what first drew you into the markets?
- In your journey, you’ve gone from sleepless nights to creating the ITM strategy. Does that stand for ‘In The Money’? What was the turning point that made you change your entire approach?
- You’ve said the advice ‘you can’t time the market’ is misleading. Why do you think that’s such a persistent myth?
- Can you share a real-world example of when market timing has worked for you – and a time when it didn’t?
- For the trader listening who wants to apply timing without becoming a day trader, what’s a simple principle they can start with?
- You call your losses ‘tuition fees’. What’s the most expensive lesson you’ve ever paid for – and what did it teach you?
- How can traders tell the difference between a ‘normal loss’ that’s part of the system – and a loss that means something’s broken?
- What do you think stops traders from learning from their losses instead of repeating them?
- You’ve been exploring AI in the markets. Where do you see it genuinely helping traders, and where is it just hype?
- If a trader wanted to dip their toe into using AI tools without losing their edge, where should they start – and what should they avoid?
About Heather Cullen
Heather Cullen is an author, investor, and creator of the ‘In The Money’ strategy. It is a simple, proven approach designed to beat the market without sleepless nights or constant screen-watching.
With 25 years of trading experience, Heather has navigated booms, busts, and every mistake in between, turning her costly lessons into a roadmap for consistent profits.
She’s the author of multiple Amazon bestsellers, including Timing the Market and the In The Money series. Heather is passionate about helping traders cut through complexity, avoid unnecessary losses, and use new tools like AI wisely.
Stay in touch with Heather
LinkedIn: linkedin.com/in/heather-cullen-6b7ba76/
Website: heathercullen.com
** Free giveaway from Heather! **
Timing the Market is a very short book (1-2 hour read) that focuses on market timing with an intended readership of stock traders, including newbies.
Go to https://heathercullen.com/book-download/
Use password: TalkingTrading
About Louise Bedford
Louise Bedford has traded, taught, and written extensively about the financial markets for over 30 years, building a reputation as a highly accomplished and experienced trader, educator, and author.
She co-founded The Trading Game and has gained recognition for her unique approach to teaching trading psychology and market analysis.
Louise has authored several successful trading books. In particular, her titles include Trading Secrets, Charting Secrets, The Secret of Candlestick Charting, and Investing Psychology Secrets.
Louise runs her hugely popular, repeat-for-free Mentor Program Pro online course. Through this course, she shows you how to automate your trading so you can retire early and get on with your life.
To get in touch with Louise
Facebook: https://www.facebook.com/TradingGame/
Twitter: https://twitter.com/TheTradingGame
LinkedIn: https://linkedin.com/in/louise-bedford/
Youtube: https://www.youtube.com/tradinggame
TikTok: https://www.tiktok.com/@tradinggame.com.au
Instagram: https://www.instagram.com/tradinggame.com.au/
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Image by AI Google Labs
