I sold the stock before it doubled. Then I made money off it anyway.

Here we go, month 7 of trying to beat the S&P 500 with cash secured puts and covered calls. If this happens to be the first post you’ve seen on this, here’s what’s going on: I started a personal challenge to see if I could beat the results of investing in the S&P 500 using Vanguard’s S&P 500 ETF, ticker VOO, by selling cash secured puts and covered calls. For some it’s called a wheel strategy. You can read how I set everything up in my post: Cash Secured Puts and Covered Calls Sales, Can it Beat the S&P 500 and then see each month’s results at the following links:

Also, before we get started, I should give a disclaimer — you know, the one you always hear when people are talking about investments. I need to let you know I’m not a financial advisor and these posts are not meant as investment advice. You’d be a month behind schedule anyway and it wouldn’t help to copy the trades. Especially since they’ve mostly all expired. These are for educational and entertainment purposes only. By the way, if you are one of the ones who considers this entertaining you’re kind of a money nerd, like me. Sorry!

Here’s a really quick recap of how this personal challenge got going. I kicked off the challenge back at the beginning of June with a $6,000 deposit into a Roth IRA account and I’m selling cash secured puts or covered calls to collect the premiums and measure that against the performance of what I could have purchased in shares of VOO. I’ll post all of the trades I made each week along with an image of the account value at the end of the month. Each month I’ll compare it to the performance of the shares in VOO and keep track of the cumulative value of both accounts. So here we go again.

To start the month I am beginning from an account value of $5,652.56. After the nightmare of September and October and the slow but steady recovery in November, I can report that things are starting to feel a little less bleak. Still below the original $6,000 — but headed in the right direction. December turned out to be a month where the stars aligned in a very specific way. That’s putting it mildly.

Week 1, Dec 1 – 8

The first week of December was all about wrapping up positions that had been set up at the end of November. Two of the three open trades from last month landed exactly as hoped — and one created a new headache to manage.

First, the good news: the RIVN December 1st $16.50 put I’d sold back on November 27th expired worthless on December 1st. Rivian had stayed above $16.50, so the full $38.34 premium went straight into the pocket. Good. That’s the way the wheel is supposed to work.

The other November trade was the CVNA December 1st $32.00 covered call. I had been assigned 100 shares of Carvana at $31.50 the week before Thanksgiving and immediately sold that call at $32 collecting $101.34. On December 1st, CVNA was trading above $32 at expiration, so I was assigned — meaning the shares were called away at exactly $32. The full stock sale brought in $3,199.96.

That might not sound like much of a profit on the stock itself — I paid $31.50, sold at $32 — but add in the $66.34 I collected on the original put, the $90.34 from the first put a couple weeks before that, the $59.34 covered call before the final one, and the $101.34 from this last call, and the total wheel cycle on CVNA was actually quite respectable. The wheel worked. First clean exit in a while.

With fresh cash to deploy, I sold two new puts on December 4th:

BYND December 8 $8.00 put — collected $48.34
AFRM December 8 $38.00 put — collected $161.34

Now, that AFRM trade deserves some explanation. If you’ve been following along, you know that Affirm had been my main problem child since I got assigned 100 shares at $20 back in October, eventually getting called away in November at $19.50 — a painful exit. But something remarkable had happened in late November: Amazon announced Affirm as a buy-now-pay-later option across Amazon.com. That announcement sent AFRM stock soaring from around $26 to well above $38 almost overnight.

So when I sold that $38 put on December 4th, AFRM was already trading well above my strike. I was essentially betting it would stay above $38. With the stock at nearly $40 and climbing, that felt like a reasonable bet. The premium of $161.34 for a single week was hard to pass up.

Both puts expired worthless on December 8th. AFRM was comfortably above $38. BYND, unsurprisingly, was still below $8 — but just barely above it, letting the put expire worthless. Total week: $209.68 in net premium.

Date	Description	Qty	Price	Fees & Comm	Amount
12/1/2023	RIVN 12/01/2023 $16.50 P — expired worthless	1	—	—	—
12/1/2023	CVNA 12/01/2023 $32.00 C — assigned, sold 100 shares	100	$32.00	$0.04	$3,199.96
12/4/2023	Sold to Open BYND 12/08/2023 $8.00 P	1	$0.49	$0.66	$48.34
12/4/2023	Sold to Open AFRM 12/08/2023 $38.00 P	1	$1.62	$0.66	$161.34
12/8/2023	AFRM 12/08/2023 $38.00 P — expired worthless	1	—	—	—
12/8/2023	BYND 12/08/2023 $8.00 P — expired worthless	1	—	—	—

Week 2, Dec 11 – 17

AFRM kept going. On December 11th, with the stock now trading in the low-to-mid $40s, I sold a new put at a higher strike:

AFRM December 15 $41.50 put — collected $179.34

That’s right. AFRM had risen far enough that I moved the strike up from $38 to $41.50 — and the premium was even bigger. The stock had completely reversed its position from the lows. Months of heartbreak, and now this.

But the week wasn’t all champagne and AFRM profits. The VOD position I’d sold back in November also came due. On December 13th, Vodafone was assigned — I bought 100 shares of VOD at $9.00 per share for -$900. Vodafone, the British telecom giant, had been slowly sliding all year. The company was dealing with heavy debt, a slowing European telecom market, and ongoing regulatory review of its proposed merger with Three UK. It’s a very different kind of stock from AFRM — less exciting, less volatile, and unfortunately still drifting the wrong direction. The $16.34 premium I’d collected when I sold the put felt less impressive now.

On December 14th, I immediately sold a covered call on the new VOD position:

VOD January 19, 2024 $9.00 call — collected $11.34

Not a huge premium, but on a $900 stock position that’s about 1.3% in five weeks. I’ll take it. The plan is to let the wheel work, collect the small premiums, and get out when I can.

The big headline of the week: on December 13th, the Federal Reserve held its final meeting of 2023. Chair Powell and the FOMC signaled that rate hikes were likely over and that three rate cuts could be coming in 2024. Markets erupted. The S&P 500 ripped higher, growth stocks surged, and BNPL companies like Affirm — which are particularly sensitive to interest rate expectations — absolutely flew. AFRM had already been strong from the Amazon announcement; the Fed pivot added rocket fuel on top.

When the December 15th expiration arrived, the AFRM $41.50 put expired completely worthless. AFRM was trading well above $41.50. That’s $179.34 collected with nothing given back.

Also collected this week: $1.66 in bank interest on the cash balance.

Date	Description	Qty	Price	Fees & Comm	Amount
12/11/2023	Sold to Open AFRM 12/15/2023 $41.50 P	1	$1.80	$0.66	$179.34
12/13/2023	VOD 12/15/2023 $9.00 P — assigned, bought 100 shares	100	$9.00	—	-$900.00
12/14/2023	Sold to Open VOD 01/19/2024 $9.00 C	1	$0.12	$0.66	$11.34
12/15/2023	AFRM 12/15/2023 $41.50 P — expired worthless	1	—	—	—
12/15/2023	Bank interest	—	—	—	$1.66

Week 3, Dec 18 – 22

Okay. At this point I need to stop and acknowledge what was happening. AFRM had gone from a stock I was assigned at $20, called away at $19.50 in November at a loss, to a stock that was now trading in the mid-$40s. And I was benefiting from it not by holding shares, but by selling put after put after put and watching every single one expire worthless.

On December 18th I sold yet another put, this time at an even higher strike:

AFRM December 22 $43.00 put — collected $146.34

By December 22nd, AFRM had climbed further still — well past $43. Rather than let the put expire (which it would have, worthless), I bought it back early for a single penny:

Bought to Close AFRM $43.00 put — cost -$1.01

Why close it for a penny rather than let it expire? A few reasons: closing it frees up the cash collateral immediately, eliminates any last-minute assignment risk on the final day, and is essentially costless. This is a common practice when an option has only a cent of value left. Net on the $43 put: +$145.33.

The same day I closed the $43 put, I opened a new one at a higher strike again:

AFRM December 29 $48.00 put — collected $173.34

$48 strike. That is a number that would have seemed like science fiction just six weeks earlier when I was getting called away at $19.50. The premium for a single weekly put on AFRM was now over $170. The stock had more than doubled since I exited my position in early November. The irony is obvious: had I held through the pain rather than letting the covered calls call me out, I’d have made a fortune on the stock appreciation. But that’s not how the wheel works, and at least I’m collecting real premium as it runs.

Date	Description	Qty	Price	Fees & Comm	Amount
12/18/2023	Sold to Open AFRM 12/22/2023 $43.00 P	1	$1.47	$0.66	$146.34
12/22/2023	Bought to Close AFRM 12/22/2023 $43.00 P	1	$0.01	$0.01	-$1.01
12/22/2023	Sold to Open AFRM 12/29/2023 $48.00 P	1	$1.74	$0.66	$173.34

Week 4, Dec 29

Christmas week was short and quiet — one trade on the last trading day of the year. By December 29th, AFRM was still trading at or above $48. The December 29th put had a penny of value left in it, so I closed it out and rolled it forward into January:

Bought to Close AFRM December 29 $48.00 put — cost -$1.01
Sold to Open AFRM January 5, 2024 $48.00 put — collected $117.34

That last trade technically extends into 2024, which we’ll pick up in next month’s post. But the premium is already banked: $117.34 heading into the new year.

Date	Description	Qty	Price	Fees & Comm	Amount
12/29/2023	Bought to Close AFRM 12/29/2023 $48.00 P	1	$0.01	$0.01	-$1.01
12/29/2023	Sold to Open AFRM 01/05/2024 $48.00 P	1	$1.18	$0.66	$117.34

S&P 500 (VOO) Summary Activity and Results

December was a great month for the S&P 500 — one of the best of the year. VOO started the month at $419.40 (November 30 close) and finished December 29th at $436.80, a gain of 4.59% for the month. The big catalyst was the December 13th Fed meeting, where the FOMC’s projections showed three potential rate cuts in 2024. Markets interpreted that as a “mission accomplished” signal on inflation, and stocks ran with it into year end.

There was also a VOO dividend of $1.801 per share on December 20th. With 15.738 shares being tracked in the hypothetical account, that added $28.34 in dividends which were reinvested, bringing the total share count to 15.804 shares. At the December 29th closing price, the VOO account ended at $6,903.19.

On a cumulative basis since the challenge began on June 1, 2023, the VOO account has now grown to $6,903.19, a +15.05% total return. For a passive investment that required zero effort, that’s a solid number — and it’s out in front of the live account on a cumulative basis. We’ll get to that in the final comparison below.

Date	Activity	Cash In/Out	Share Price	Shares	Total Shares	Total Value
6/1/2023	Purchase at opening price	$6,000.00	$384.20	15.617	15.617	$6,000.00
6/29/23	Dividend of $1.576/share	$24.61	$400.60	0.061	15.678	$6,280.73
6/30/23	Month closing price	$0.00	$407.28	0.000	15.678	$6,385.46
7/31/2023	Month closing price	$0.00	$420.68	0.000	15.678	$6,595.55
8/31/2023	Month closing price	$0.00	$413.83	0.000	15.678	$6,488.15
9/28/2023	Dividend of $1.493/share	$23.41	$393.64	0.059	15.738	$6,195.02
9/29/2023	Month closing price	$0.00	$392.70	0.000	15.738	$6,180.22
10/31/2023	Month closing price	$0.00	$384.17	0.000	15.738	$6,046.07
11/30/2023	Month closing price	$0.00	$419.40	0.000	15.738	$6,600.52
12/20/2023	Dividend of $1.801/share	$28.34	$430.09	0.066	15.804	$6,795.14
12/29/2023	Month closing price	$0.00	$436.80	0.000	15.804	$6,903.19

Month End Results on Live Account

Seven months in. Let’s look at what actually happened.

The month started at $5,652.56 and ended at $6,470.21, a gain of $817.65 — a +14.47% return for December. That is, without question, the best single month of the entire challenge. The account broke back above the original $6,000 starting value for the first time since early August, and it did so with some room to spare.

The story of December was almost entirely AFRM. Over the course of four weeks, I sold five different puts on Affirm at steadily increasing strike prices — $38, $41.50, $43, $48, and $48 again — and every single one expired worthless or was closed for a penny. The combined net premium from AFRM puts alone was over $650 in a single month. Throw in the CVNA wheel completing cleanly, the BYND and RIVN puts expiring, and a small kick from bank interest, and the total net premium collected for the month came to approximately $837 (the difference from the account gain reflects the mark-to-market value of the open VOD position and the AFRM January put still on the books at year end).

December 2023 Trades Summary

Date	Description	Qty	Price	Fees & Comm	Amount
12/1/2023	CVNA 12/01/2023 $32.00 C — assigned, sold 100 CVNA	100	$32.00	$0.04	$3,199.96
12/4/2023	Sold to Open BYND 12/08/2023 $8.00 P	1	$0.49	$0.66	$48.34
12/4/2023	Sold to Open AFRM 12/08/2023 $38.00 P	1	$1.62	$0.66	$161.34
12/8/2023	AFRM 12/08/2023 $38.00 P — expired worthless	1	—	—	—
12/8/2023	BYND 12/08/2023 $8.00 P — expired worthless	1	—	—	—
12/11/2023	Sold to Open AFRM 12/15/2023 $41.50 P	1	$1.80	$0.66	$179.34
12/13/2023	VOD 12/15/2023 $9.00 P — assigned, bought 100 VOD	100	$9.00	—	-$900.00
12/14/2023	Sold to Open VOD 01/19/2024 $9.00 C	1	$0.12	$0.66	$11.34
12/15/2023	AFRM 12/15/2023 $41.50 P — expired worthless	1	—	—	—
12/15/2023	Bank interest	—	—	—	$1.66
12/18/2023	Sold to Open AFRM 12/22/2023 $43.00 P	1	$1.47	$0.66	$146.34
12/22/2023	Bought to Close AFRM 12/22/2023 $43.00 P	1	$0.01	$0.01	-$1.01
12/22/2023	Sold to Open AFRM 12/29/2023 $48.00 P	1	$1.74	$0.66	$173.34
12/29/2023	Bought to Close AFRM 12/29/2023 $48.00 P	1	$0.01	$0.01	-$1.01
12/29/2023	Sold to Open AFRM 01/05/2024 $48.00 P	1	$1.18	$0.66	$117.34

Final Comparison

Here’s where things stand. The VOO account ended December at $6,903.19, which represents a +15.05% total return since the challenge began. That’s a genuinely good number for a passive, do-nothing-but-hold strategy.

The live account ended at $6,470.21, which is +7.84% from the starting $6,000. After sitting below breakeven for the better part of four months, the account is finally back in positive territory on a total return basis. December alone added more than $800, which is a bigger single-month gain than the account had ever seen.

The gap between the two accounts is now about $433, or roughly 7.2 percentage points on total return. That’s meaningful, but it’s no longer the chasm it was. Two months ago VOO was up 10% and the live account was down 21% — a 31-point spread. That spread has closed dramatically in just 60 days.

VOO is still winning. That’s the honest answer. But the direction has clearly turned.

Date	S&P 500 ETF Account (VOO)	Change %	Total Change %	Live Account	Change %	Total Change %
5/31/23	$6,000.00	—	—	$6,000.00	—	—
6/30/23	$6,385.46	6.42%	6.42%	$6,457.71	7.63%	7.63%
7/31/23	$6,595.55	3.29%	9.93%	$7,459.88	15.52%	24.33%
8/31/23	$6,488.15	-1.63%	8.14%	$6,132.29	-17.80%	2.20%
9/30/23	$6,180.22	-4.75%	3.00%	$5,496.47	-10.37%	-8.39%
10/31/23	$6,046.07	-2.17%	0.77%	$4,751.35	-13.56%	-20.81%
11/30/23	$6,600.52	9.17%	10.01%	$5,652.56	18.97%	-5.79%
12/29/23	$6,903.19	4.59%	15.05%	$6,470.21	14.47%	7.84%

Ending Thoughts

Let me be real: December was the month this whole challenge needed. After the October low of $4,751 — where I was sitting down more than 20% while VOO was essentially flat — it looked like this experiment might end with a pretty definitive conclusion: just buy the index. November started to turn things around. December took that turn and floored it.

The AFRM story is genuinely wild. A stock I agonized over for months — buying at $20, watching it sink, grinding out tiny covered call premiums week after week — finally broke my way. But in the most bittersweet way possible: it ran after I had already sold it. The Amazon partnership and the Fed pivot sent AFRM from the $20s to nearly $50 in a matter of weeks, and I was no longer a shareholder. Instead I was a put seller, collecting premium as it climbed past every single strike I threw at it.

Is that better or worse than having held the shares? Worse, probably — on pure dollar terms. But the discipline of the wheel strategy meant I still captured real, meaningful income from the move. Over $650 in AFRM premiums in a single month isn’t nothing.

The VOD situation is the one dark cloud heading into January. I’ve got 100 shares of a slow-moving telecom stock that just keeps creeping lower, and a covered call on it that doesn’t expire until January 19th. It’s not going to sink the account, but it’s a reminder that the wheel works best on stocks you’re genuinely comfortable owning — and Vodafone is one I’m watching nervously.

The bigger picture: for the first time since July, I’m heading into a new month with the account above water on the challenge. There’s still ground to make up on VOO — about $433 worth — but the trend is pointing the right direction. See you in January.

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Cash Secured Puts vs S&P 500 Challenge. Month 7, December 2023