🎤Samuel Wong: The Seller's Edge — A Practical Guide to Selling Cash-Secured Puts

Topic: From Options 101 to Order Execution ∙ Reading the Greeks and Moneyness ∙ Monitoring, Rolling and Surviving Liquidation Risk

Speaker: Samuel Wong

Samuel Wong, Investment Representative at Tiger Brokers (Singapore), walks through the cash-secured put strategy from first principles to live execution — including strike selection, order types, position monitoring, rolling, and the five most common mistakes he sees option sellers make.

Samuel Wong is a trader with over 5 years of experience across market segments including precious metals and cryptocurrency, and 2 years of technical experience in financial derivatives ranging from US options and futures to SGX-listed DLCs. He also serves as an in-house trainer and speaker for Tiger Brokers, and as an Investment Representative for Tiger Brokers Singapore, supporting both new and like-minded investors through their journey with care and guidance.

I. Opening: Options Aren't Just for Speculation

Samuel opened by naming the elephant in the room directly: "I know some people think options are for gambling — you can make a lot of money, or you can lose everything you put into it." His counter: options are used just as much by risk managers and patient investors as they are by speculators. The session's focus — the sell put strategy — was built specifically around that second group.

🎙️ On-site framing: "It's not a zero-sum game. In the end of the day, [buyers and sellers] are actually two [approaches] used by both investors and portfolio managers to manage risk — it's not just a tool used for speculation."

II. Module 1: Reading the Greeks and Moneyness

Before touching a strike price, Samuel walked through the mechanics every option seller needs:

• A put option gives the holder the right to sell 100 shares at a strike price. Buyers use puts to hedge portfolios or speculate on a decline; sellers collect a premium upfront in exchange for the obligation to buy shares if assigned.

• The Greeks — Delta (directional/probability proxy), Gamma (delta's rate of change), Vega (sensitivity to implied volatility), and Theta, which Samuel flagged as the one sellers care about most: "it indicates how fast the price will decay... near its end of lifespan."

• Moneyness — in, at, or out of the money. At-the-money options carry the richest premium but the highest uncertainty; out-of-the-money options are cheaper but decay fastest if the trade goes nowhere.

His rule of thumb for sellers: "Generally, you actually want to look at out-of-the-money options... you want to collect premium and you don't want to get assigned at a price that's too high."

Three structures exist for selling puts — cash-secured, naked (on margin), and the more advanced put vertical spread — with the session's hands-on portion built entirely around the cash-secured version, since "assignment isn't really a bad thing for investors — it allows them to buy the shares at the entry they're looking at."

III. Module 2: The Pre-Trade Checklist — Picking a Strike (Live Nvidia Walkthrough)

Samuel's five-point checklist before selling any put:

1. Only sell puts on stocks you actually want to own — not whatever's trending

2. Have a bullish-to-neutral market outlook, ideally with an identifiable support level

3. Check implied volatility — high IV means richer premium, but a higher chance of assignment

4. Pick a 35–45 day time horizon — "it captures the optimal [theta decay] without tying up your buying power for too long"

5. Choose a conservative strike, roughly 10–15% below market, to buffer against normal price noise

He demonstrated this live on Nvidia: filtering the options chain to puts, zooming into a chart where the stock had bounced twice off $190 with RSI drifting toward oversold, and landing on the $195 strike — a delta of roughly -0.20, implying an estimated 80% win rate. "I don't want to sell options that are further out of the money because they'll carry less premium... $195 here would be a sweet spot to me."

🎙️ On-site Quote: "For put sellers, what should you be selling — in the money or out of the money?" (Audience: "out the money.") "Correct."

IV. Module 3: From Order to Exit — Execution, Monitoring, and Rolling on the App

Placing the trade: select the put on the options chain → tap Sell → choose market or limit order and quantity (remembering 1 lot = 100 shares, so a $2.75 quote means $275) → confirm. The confirmation screen shows a P&L diagram and margin usage before the order goes live.

Market vs. limit: on tightly-spread, liquid contracts, market orders fill fine. On wider spreads — Samuel's example showed an $8.30 ask against a $6.00 bid — a market order can hand away real premium. His fix: place a limit order at the mid-price or last-traded price instead, especially when rolling.

Monitoring: the portfolio page tracks realized and unrealized P&L per position. A short put showing an unrealized loss isn't automatically a problem — "as an investor, remember that you're either looking to collect income or take assignment at the price you're looking for. This unrealized loss should not shake you."

Rolling: closing the existing put and opening a new one, either further out in time (usually a net credit) or down in strike (usually a net debit) to manage risk or buy time. "Rolling does not erase past losses — it only realizes the current gain or loss and shifts risk to a new trade or price level."

V. Module 4: Assignment, Liquidation, and the Five Pitfalls to Avoid

Assignment triggers when a put expires in the money or is exercised early — the seller is obligated to buy 100 shares at the strike, whether that means holding, selling to free up capital, or eventually writing a covered call against the position.

Liquidation is protective, not punitive, in most cases. Two triggers:

• Near-expiry liquidation — insufficient cash/margin to support potential assignment

• Margin call — account health dropping below roughly 16% (margin call) or 5% (liquidation risk); a fully cash-secured position stays at 100% and isn't exposed to this at all

🛡️ Samuel's five most common pitfalls:

1. Selling puts on stocks you don't actually want to own (chasing "meme stock" premium)

2. Holding through earnings, where gap risk spikes

3. Entering without a defined exit plan

4. Ignoring cash/margin requirements and overcommitting

5. Using market orders on illiquid contracts, and selling at-the-money purely for the bigger premium

🎙️ On-site Quote: "Selling at-the-money puts with high implied volatility comes with what?" (Audience: "Higher premium, but higher risk of assignment.") "Correct — because it's at the money, there's a high chance the price can move against you... I try to push my strike prices further out of the money. That way I'm able to sleep at night."

💬 Discussion: What's Your Approach to Selling Puts?

We'd love to hear from you:

🔹 Q1: Have you sold a cash-secured put before? What strike/timeframe did you use, and why?

🔹 Q2: Have you ever been assigned shares you didn't actually want? What happened next?

🔹 Q3: Market orders or limit orders — which do you default to, and has a wide spread ever cost you?

👇 Drop your answers in the comments below and earn Tiger Coins in return!