To The Moon

Speaker: Samuel Wong, Investment Representative at Tiger Brokers, as he breaks down options fundamentals for first-timers and walks through why selling puts — not just buying calls — is one of the most underrated tools in a retail investor's kit.

[About the Speaker]
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.

[The Hook] "Most people think options are for gambling. You can make a lot of money, or lose everything you put in." Samuel opened with the line everyone expects to hear about options — then spent the next hour dismantling it. Options aren't just speculation vehicles; they're used by risk managers and patient investors alike. His focus for the session: the sell put strategy, and specifically the cash-secured put.

[What Actually Is an Option?]

An option is a financial contract, not a stock — it has to be based on an underlying company. One option typically represents 100 shares, and unlike stocks, options carry an expiration date. Expire out of the money, and the option can be a full loss.

A put option gives the holder the right (not obligation) to sell 100 shares at an agreed strike price, any time before expiry. Two reasons people buy puts:

• Hedging — portfolio managers protecting existing holdings from downside

• Directional speculation — betting a stock falls in price

[The Flip Side: Why Sell a Put?]

This is where Samuel's talk really started. When you write and sell a put instead of buying one, you collect a premium upfront from the buyer — but take on the obligation to buy shares at the strike price if the buyer decides to exercise. Unlike the buyer, the seller doesn't get a choice once assigned.

Two reasons investors sell puts:

• Bullish or neutral income play — profit from a stock without owning it, just by collecting premium

• Discounted entry — get paid while waiting to buy shares at a price you already wanted

Samuel illustrated this with a two-sided story: a portfolio manager buys a put to hedge shares he doesn't want to sell but fears a near-term drop. On the other side, an investor who thinks a stock is too expensive right now sells a put at a lower strike — collecting income while waiting for a discount. "It's not a zero-sum game. In the end of the day, they're actually two [tools] used by both investors and portfolio managers to manage risk."

If the stock stays flat or rises, the put seller keeps the full premium. If it falls enough to get assigned, the premium collected lowers the effective cost basis of the shares bought.

[The Greeks and Moneyness, Simplified]

Option prices move on the underlying share price plus the Greeks:

• Delta — price sensitivity, and a rough proxy for probability of expiring in the money

• Gamma — the rate of change of delta (more relevant to active traders)

• Vega — how implied volatility affects price

• Theta — time decay, "important for [option] sellers because [theta] indicates how fast the price will decay... near its end of lifespan"

And every option sits in one of three "moneyness" zones:

• In the money (ITM) — holds intrinsic value, behaves more like equity

• At the money (ATM) — highest volume and most uncertainty, priciest relative to strike proximity

• Out of the money (OTM) — cheapest, but decays fast if it stays OTM

"For option sellers, especially for the sell-put strategy, you actually want to look at out-of-the-money options" — collect premium without accepting an unfavorable assignment price.

[Three Flavors of Selling Puts]

Samuel named three approaches, focusing the session on the first:

1. Cash-secured put — set aside enough cash to buy 100 shares if assigned. "Assignment isn't really a bad thing for investors because it allows them to buy the shares at the entry that they're looking at."

2. Naked put (on margin) — more for traders chasing income without full cash backing

3. Put vertical spread — a more advanced, defined-risk structure covered in a separate seminar

[Key Takeaways]

• Selling isn't the same risk as buying. The put seller trades unlimited-ish downside exposure for upfront income — know which side of the trade you're on.

• Moneyness drives strategy. OTM strikes are the sweet spot for most put sellers who want premium without inviting assignment.

• Theta is your friend when you're short. Time decay works in the seller's favor.

[Call to Action 🎯]

1. Pull up the options chain on a stock you already want to own, and find its current delta at a few strikes below market.

2. Write down: would you be happy owning this stock at that strike price? If not, it's not a candidate for a cash-secured put.

3. Drop a comment: what's one stock you'd genuinely be happy to buy at a 10–15% discount to today's price?

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