Living in New Zealand, Simon sleeps during most US market hours. Therefore, he needed a strategy that could deliver consistent income with one check-in per day. He came up with the Time Flies Spread, a weekly strategy that benefits from both time and volatility. So far the results have been outstanding. This year, he has seen 45% profits in less than four months.
Watch Simon Black explain his Time Flies Spread
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Simon Black, a New Zealand-based options trader since 2007, brings an engineering mindset to his trading. Because of the big time difference to the US markets, he can only trade during the last 1-2 hours the market is open. This has influenced how he trades.
This is the Time Flies Spread
The Time Flies Spread is a delta-neutral, theta-positive weekly options trading strategy designed to profit from time decay while managing volatility.
At its core, the strategy combines a put diagonal and a call broken wing butterfly. Simon trades it on RUT, but the strategy can also be used on other underlying.
How the strategy works
The Time Flies Spread blends two trades to create a robust setup:
- Put Diagonal (below the market): This involves selling a put option with a closer expiration and buying a put with a later expiration at a different strike. It capitalizes on time decay and benefits from volatility spikes during market drops, providing a downside buffer.
- Call Broken Wing Butterfly (above the market): This trade shorts two call options and buys calls at different strikes, with one “wing” extended. It thrives when volatility contracts during market upswings, enhancing profitability.
This is the example of a Time Flies Spread Simon uses in the video.
Simon places these trades weekly, typically on Thursdays. The expiration is set for 8 days later – on Friday the following week. The long put expires on the Monday after. As a starting point, he will center the diagonal about 3% below the market and the broken wing butterfly about 3% above the market.
He designs the trade using OptionStrat and plays with different strikes until he gets a profit/loss curve he likes.
He will exit the trade when it reaches a profit of 10% of the max loss or buying power. Simon says he always tries to be out of the trade 24 hours before expiration to avoid last-minute volatility whipsaws, ensuring disciplined risk management.
Managing risk and adjustments
The Time Flies Spread is a defined-risk strategy. Losses are capped, with Simon comfortable accepting up to a 40–50% loss, though such outcomes are rare.
To manage adverse moves, he may add calendars above the butterfly or below the diagonal as insurance, as demonstrated during a profitable trade amid Trump’s tariff announcement. Traders can also exit early if the market moves significantly, leveraging tools like OptionStrat for real-time adjustments.
Simon’s results
Since adopting the Time Flies Spread, Simon has achieved a 45% return in 2025, trading RUT for its lower volatility compared to the SPX. With 11 wins out of 12 trades this year, he’s on track for his ambitious 100% annual return goal. The results are calculated on the basis of having allocated $3,000 in buying power for each trade.
Curious about learning more about Time Flies Spread? Watch the full interview to understand the mechanics and how Simon trades it.
Learn more about options trading
I always ask my guests if they have a book on options trading they would like to recommend to other traders.
Simon’s recommendation:
- Julia Spina: The Unlucky Investor’s Guide to Options Trading
He also recommends the YouTube channel of Dan Sheridan.
