To The Moon

I Paid $8,500 To Stay In The Rally. Here's Why.

Last week I wrote about how the portfolio is built to work regardless of whether 7000 is a bull run or a blow-off top. Three strategies, three different market conditions, same portfolio.

This week the market tested that. And I want to show you exactly what happened — the good, the bad, and the $19,000 loss I took on purpose.

What Actually Happened

MARA ripped past $11.80. SPY kept grinding above $700. Both moves blew straight through my short call strikes.

On MARA I had 80 contracts of $11 covered calls expiring April 17. When the stock pushed through $11 and kept going, those calls went deep in the money. I had a choice — let them get assigned and lose my shares at $11, or roll them up to higher strikes and pay the difference.

I rolled. Cost me about $8,500 across the week in MARA call rolls alone. Closed the $11 calls at a loss, opened new $12 calls further out. Closed $10.50 calls at a loss, rolled them to $11.5 and $12 strikes. Every single one of those closes shows up as a negative number on my realized P/L. On paper it looks like a terrible week.

On SPY it was the same story — my $700 and $685 short calls were underwater. Rolled those up to $725 and $730 strikes. Another $2,300 in roll costs.

So the question is: why would I pay $10,000+ to roll positions that were "losing"?

Because The Alternative Costs More

Here's the math that most retail traders miss about covered calls.

If I'd let those MARA $11 calls get assigned, I'd have sold 8,000 shares at $11. MARA closed the week at $11.80. That's $0.80 x 8,000 = $6,400 of upside I would have given away — plus I'd have lost my cost basis position on shares I bought at $10 through put exercises. I'd have to buy back in at $11.80 to re-enter the wheel, which means paying more for the same shares.

By rolling up to $12 strikes, I kept all 46,546 shares, I'm now selling calls $0.50 higher than before, and if MARA keeps running to $13 or $14 I participate in that move. The $8,500 I paid to roll is the price of staying in the rally. It's not a loss — it's a repositioning cost.

Same logic on SPY. Rolling the short calls up from $700 to $725-$730 cost me money today but keeps my LEAPS running if the market continues higher.

This is the part of options trading that nobody talks about on social media. Rolling at a loss feels wrong. Every instinct says "I'm losing money." But the realized loss on the short call is offset by the unrealized gain on the underlying position. You're not losing — you're paying to keep playing.

The Other Side Of The Book

While the short calls were costing me money, everything else was doing its job.

The puts printed. I closed MARA $8 and $8.50 puts across the week for about $3,300 in profit. These were sold when MARA was lower, and the rally pushed them out of the money fast. Closed them, collected the premium, opened new $9 puts further out. I now have 100 contracts of MARA $9 puts spread across May 15 and May 22 — reloaded and ready.

The SPY LEAPS appreciated. I now have six of them — four December 2026 calls and two March 2027 calls. The December $670 and $675 LEAPS are sitting on +$2,087 and +$2,237 in unrealized gains. I added the newer ones at $705 and $710 this week, scaling up into the rally. Total LEAPS exposure in SPY is now around $42,000 in market value.

The front spreads adjusted higher. I've got put ratio spreads running at $690/$675 and $675/$630 across May and August expiries. If SPY reverses from here, these activate. If it doesn't, the cost is small and the premium from the short legs offsets most of it.

The MSFT PMCC is quietly working — the June 2027 $360 LEAPS is up about $1,500 from where I opened it two weeks ago, net of the short call decay.

Account for the week: $707,000 to roughly $712,000. Up, not down — despite $10,000 in roll costs showing up as realized losses.

The $19,500 I'm Not Sugarcoating

I closed my ETHA position this week. 25 contracts of iShares Ethereum Trust LEAPS, January 2027 expiry, $36 strike. Realized loss: $19,497.

This was a pure directional bet on Ethereum. No premium overlay, no short calls against it, no hedge. Just long LEAPS hoping ETH would rally. It didn't — at least not on my timeline — and every month that passed the time decay ate into the position.

I held it too long. Should have cut it months ago when the thesis started breaking down. That's the honest truth. A LEAPS without a premium engine on top of it is just a leveraged directional bet with a timer on it, and the timer ran out before the move came.

The capital went straight into SPY LEAPS and the MSFT PMCC. Same instrument — long-dated calls — but now with short calls sold against them generating income every cycle. The structure makes the difference. A LEAPS by itself is hope. A LEAPS with a short call is a business.

What The Portfolio Looks Like Now

The core hasn't changed, but the strikes have moved up and the SPY PMCC book got significantly bigger.

MARA: 46,546 shares. Short calls now at $11.5–$12 across May and late May instead of $10–$11 a month ago. 100 short put contracts at $9 strike. The wheel is running at higher levels because MARA is trading at higher levels.

SPY: 6 LEAPS (up from 2 a month ago), rolling short calls at $725–$730, front spreads layered from $630 to $690 across three different expiry dates. The PMCC is the growth engine now.

MSFT: PMCC running. One LEAPS, one short call. Clean and simple.

BMNR and COIN: still winding down. Short calls on both, letting them decay and roll off naturally.

The Takeaway

If you're running a wheel or any covered strategy, you will have weeks where the market rips through your strikes and you have to pay to roll. It feels like losing. It shows up as negative realized P/L. And it is the correct thing to do.

The alternative — letting shares get called away at a low strike while the stock keeps running — is more expensive. You just don't see that cost on your statement because it shows up as opportunity cost, not a realized number.

Track both sides. The roll cost AND the unrealized gain on the position you kept. This week I paid $8,500 to roll MARA calls. The shares I kept gained roughly $12,000 in market value over the same period. Net positive. The math works.

That's the whole game. Stop guessing. Start calculating.

For anyone who wants the detail on how rolling works or how to decide when to roll vs. let it assign — drop a comment below. Also happy to take questions on TikTok or YouTube DMs (Mathematical Money), or through trueknot.sg.

More coming next week. 🤙