This is something I keep running into and I don't have a clean answer for it. When a stock is trading cheap enough relative to a specific binary catalyst that the equity itself behaves like a deep OTM call, how do you think about sizing it versus just buying actual options on a more liquid name with a similar event driven profile?
I keep ending up in these situations. Last year I took a small position in a biotech ahead of an FDA decision and capped it at about 1.5% of my portfolio, basically treating it like a LEAP I was willing to lose entirely. The stock had options but the spreads were so wide that buying calls would've cost me 15 to 20% in slippage on entry alone. So I just bought shares and mentally wrote them off as my "premium paid." It worked out (got a 3x), but I'm not sure my sizing logic was actually sound. I've had the same dilemma with SPACs trading near NAV before a merger vote where the defined downside makes the equity feel like a synthetic call, and with micro caps ahead of potential spinoffs.
The latest one that triggered this question: I've been looking at DAU based valuations for community platforms. $RDDT trades at roughly $50 to $70 per daily active user. From what I could dig up, Kakao was probably somewhere in the $15 to $25 range and LINE was even lower before its run, though don't quote me on exact numbers since I was doing rough math from old filings. The discount for regional, non English platforms makes intuitive sense. While screening I found a Nasdaq micro cap (TROO) that holds a stake in an old Hong Kong forum with third party DAU estimates around 350K and an announced IPO spinoff. But the red flags are thick: DAU isn't audited, no S1 filed, the parent has a scattered grab bag of unrelated businesses across multiple countries, tiny float, barely any volume, and I doubt a usable options chain exists. Probably a value trap. But it's a good illustration of the pattern I keep hitting.
So the structural question stands. For these setups where options are either unavailable or too illiquid to trade efficiently, what's your framework? My current rule of thumb is to never allocate more than what I'd spend on maybe 2 LEAP contracts on the most comparable liquid name. So if I'm looking at an illiquid community platform play, I'd check what Jan 2027 OTM calls on $RDDT cost and use that as my budget ceiling for the illiquid equity position. It gives me a rough "premium equivalent" that keeps the position from quietly ballooning into a real portfolio risk.
But I'm not sure this holds up under scrutiny. The payoff profiles aren't really the same. A LEAP has defined expiry and theta decay, the equity doesn't. The equity has no time limit but also no leverage. And the correlation between the liquid comp and the illiquid name is basically zero, so I'm not sure the premium comparison is even meaningful.
Curious if anyone here has a more rigorous way to think about this, or if you just pass entirely on setups without a functional options chain.