To The Moon

I haven't posted in four weeks. It wasn't for lack of things happening. The opposite.

Since I last wrote, MSFT went from the $500s to the mid-$380s. Bitcoin dropped roughly 20% in June — its worst month of the year — and printed a fresh 21-month low in the process. The tech-led sell-off broadened. Chipmakers cracked. The Fed pivoted hawkish enough that Bank of America now models three rate hikes this year, not the cuts most of the market was pricing in.

I wanted to wait until the dust settled before writing about any of it honestly. Now it has, at least enough to see the shape of what happened.

The last post ended with this line: "Whether it holds in a real drawdown is a different question, and I don't have an honest answer until I'm in one."

I'm in one. Here's what the book did.

What The System Did Not Do

I didn't close the underwater MSFT LEAPS. Every single one from the June harvest is still open. Every single one is red.

I didn't liquidate MARA shares into the pullback. Not one share sold voluntarily.

I didn't stop selling puts. The wheel kept running through the drop on COIN, MARA, and IBIT. Some of those puts were the ones I sold weeks ago at what turned out to be near-term highs. They came due. They got assigned. That's the design.

I didn't buy portfolio-level tail hedges at panic prices. No SPX puts opened during the tech crack. No VIX calls. The hedges I already had — front spreads on SPY, small position sizes on the newer names — did what they were supposed to do without me needing to buy expensive protection after the fact.

None of that was heroic. It's just what happens when you commit to a framework and then let it run through a bad tape.

What The System Actually Did

Three things worth walking through.

MSFT: I added to a losing position.

The three LEAPS I closed in early June for the harvest — the ones I wrote about in Post 11 — I would still hold if I hadn't sold them. Selling at $43 versus $26 today was correct.

The immediate redeployment at higher strikes — the one I wrote about being down 35% in Post 12 — is now down more. Roughly 40% to 45% on the mark, depending on the position.

What I did this week is buy more. Three additional LEAPS at the June 2027 $450 strike. Two blocks of deep in-the-money puts sold at $415 and $410 for July and August expiry — which is effectively agreeing to own MSFT at those prices if the stock finishes below them.

I want to be direct: this is a discretionary add, not a rule firing. The framework has a "buy the next rung when a rung doubles" rule. It doesn't have a "add to a losing LEAPS position" rule. This one is a judgment call on a name I already had conviction on, at a price I think matters.

Could be wrong. The position is now bigger and more concentrated in MSFT than it was six weeks ago. If MSFT keeps falling, this add makes the pain worse before it gets better. That's the trade I'm choosing to take. Anyone reading this shouldn't copy it without understanding that specific risk.

The wheel took assignments as designed.

COIN dropped hard through June. The short puts I'd been writing at $170 and $175 came due. I got assigned. My COIN share count roughly tripled, and my cost basis on the position dropped from the $240s to the sub-$200 range as those lower-strike shares came in.

IBIT went the same way. The $38 put I'd sold as a small starter position ended up assigned. I now hold IBIT shares directly — my first ever direct Bitcoin-ETF exposure.

These weren't decisions. They were pre-committed weeks ago when I sold the puts. That's what the wheel does. It picks the price at which you're willing to own the stock, collects premium for waiting, and hands you the shares if the price comes to you. I set those strikes. The market delivered on them.

The new wheels — COIN calls at $170 to $185, IBIT calls at $38 — are running as expected. Premium coming in at the new levels. Position operational.

MARA kept doing what MARA does.

The June expiry took another call assignment wave. The share count is now down to about 48% of the peak I held back in April. That's roughly half the position gone via assignments, none of it sold voluntarily.

Effective cost basis has continued to improve — mid $11s now, versus mid $14s at the peak. MARA closed the week around $12.65, so the position is still green. Wheel is now writing calls at the $13 to $15 strikes across July expiries. Nothing surprising. Nothing dramatic. The system is winding the position down naturally as the recovery plays out.

What Else Is New

A few smaller structural changes worth mentioning briefly.

NVDA LEAPS scaled up. The starter position from Post 12 has grown to four contracts at the June 2027 $250 strike, with short calls written against them for August. Same PMCC pattern as MSFT, just at a different name and a smaller size.

Opened short puts on ORCL at $135 for July expiry. Small position, testing framework on a fresh ticker.

Ran a paired long EchoStar / short SPCX position through the pullback — the two are held together, not as separate bets. The short SPCX leg is up about $7,900 and offsetting the drawdown on the EchoStar leg. It's a hedged structure with a specific thesis behind it, not a naked short and not a directional call. I'm not going to explain the full setup in this post — it's a different playbook to the wheel and PMCC stuff I usually write about, and it deserves its own writeup. If enough of you want to see how the pair is structured, the thesis, and the risk sizing, drop a comment below saying so. Get enough interest and I'll do a dedicated post walking through it.

Parked a meaningful chunk of unused cash in the SGD money market fund. That segment is now materially larger than it was a month ago. Not a strategic move — just wanted paying-interest cash sitting somewhere useful while the book runs on margin at the margins.

The Honest Read

I'm not celebrating anything here. The book is bigger, more concentrated in a few losing positions, and using more margin than it was six weeks ago. If MSFT continues down from here, I take real damage. If BTC breaks through the June low and drags the crypto complex further, the newly assigned COIN and IBIT positions hurt more before they help. If the Fed actually hikes three times this year, tech valuations compress further and my LEAPS ladder gets tested harder than it has been so far.

Those are the honest downside scenarios. Anyone who tells you they don't exist in this book right now hasn't looked at the positions.

What the framework did that I can point to positively: it absorbed a 20% drop in Bitcoin, a 20% drop in MSFT, and a broad tech rotation, without me making a single panic decision. Assignments hit at the strikes I picked. Cost basis improved on the names where the wheel is winding down. The structure didn't break.

That's not the same as winning. It's just staying in the game. Which is the whole point of the framework — because you don't get to compound if you exit at the low.

If you want the detail on how to think about adding to a losing LEAPS position, when to accept assignment versus roll, or how to size wheel entries so that the assignments don't break the book — drop a comment below. Faster channels are TikTok and YouTube DMs (Mathematical Money on both) or through trueknot.sg.

Stay disciplined. Size your positions properly. See you next week. 🤙