To The Moon

Speaker: Samuel Wong, Investment Representative at Tiger Brokers, closes the seminar with the part most beginners skip — how to monitor a short put once it's live, what assignment and liquidation actually mean, and the five mistakes he sees option sellers make most often.

[About the Speaker]
Samuel Wang is a trader with over 5 years of experience across precious metals and cryptocurrency, and 2 years of technical experience in derivatives spanning US options, futures, and SGX-listed DLCs. He is an in-house trainer and speaker for Tiger Brokers, and an Investment Representative for Tiger Brokers Singapore.

[The Hook] "Please don't trade like an ostrich with your head in the ground — 'okay, I don't see the rate anymore, now it's a brand new one.'" Samuel's closing stretch was the most candid part of the seminar: real screenshots of his own trades, including one showing a 412% unrealized loss on a put — and why that number alone shouldn't trigger panic.

[Two Ways a Short Put Plays Out]

Scenario 1 — the stock holds or rises. The put stays out of the money, decays in value, and the seller books an unrealized (then realized) gain by buying it back cheap or letting it expire. Samuel showed a call he sold for $67 that decayed to $4 — a 94% realized gain if closed early.

Scenario 2 — the stock drops. The put moves in the money, and the position shows an unrealized loss. "Don't panic. As an investor, remember that you're either looking to collect income or take assignment at the price you're actually looking for. This unrealized loss should not shake you." Traders managing risk more actively, however, need a plan to cut losses or adjust.

[Rolling: Buying Time Without Erasing the Trade]

To roll, you close the existing put and simultaneously open a new one — usually further out in time, and sometimes at a different strike. "Rolling does not erase past losses; it only realizes the current gain or loss and shifts risk to a new trade or price level."

Two directions:

• Roll out (later expiration) — typically collects a net credit, since further-dated puts cost more

• Roll down (lower strike) — usually costs a net debit, since lower/further-OTM strikes are cheaper, but reduces assignment risk

[Assignment, Early Exercise, and Liquidation — Demystified]

Assignment happens when a put expires in the money, or the buyer exercises early. As the seller, you're obligated to buy 100 shares at the strike. Options are: hold the shares, sell them to free up buying power, or eventually sell a covered call against them.

Liquidation has a bad reputation, but Samuel stressed it's mostly protective, not punitive. Two triggers:

1. Near-expiry liquidation — if there isn't enough cash/margin to support assignment, the broker may close the position before expiry to prevent an unmanageable outcome.

2. Margin call / insufficient maintenance margin — account equity (visible as an "account health" percentage) drops below a threshold; below roughly 16% triggers a margin call, below roughly 5% triggers liquidation risk. A cash-secured put funded in cash, with no margin used, stays at 100% health and isn't exposed to this risk.

[Five Pitfalls Samuel Sees Most Often]

1. Selling puts on stocks you don't actually want to own — chasing high premium on "meme stock" volatility, then getting stuck holding shares you never wanted

2. Holding through earnings — bigger premium, but much bigger gap risk

3. No exit plan — entering without a target, then panic-closing at a loss

4. Ignoring cash/margin requirements — overcommitting to more puts than the account can actually support

5. Using market orders on illiquid options and selling at-the-money for premium — at-the-money puts pay more, but "there's actually a high chance the price can move against you." Samuel's own preference: push strikes further out of the money and accept less premium for a meaningfully lower assignment risk — "that way I'm able to sleep at night."

[Key Takeaways]

• An unrealized loss isn't automatically a mistake — if assignment was the original goal, the number is just paper until expiration.

• Rolling is a risk-management tool, not a loss-eraser. Track full P&L across the rolled positions, not just the latest leg.

• Liquidation is usually protective, not a blow-up — cash-secured (not margin-funded) positions are the lowest-risk way to avoid it entirely.

[Call to Action 🎯]

1. Before your next put sale, write down your exit rule in advance (e.g., "close at 60–75% of max profit").

2. Check your account's margin health page and understand what triggers a margin call vs. liquidation for your account type.

3. Drop a comment: which of the five pitfalls above have you run into yourself — and what did you change afterward?

Markets are always moving - and sometimes, the best move is knowing what works for you.

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