Here we go, month 6 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:
Cash Secured Puts vs S&P 500 Challenge. Month 1, June 2023.
Cash Secured Puts vs S&P 500 Challenge. Month 2, July 2023
Cash Secured Puts vs S&P 500 Challenge. Month 3, August 2023
Cash Secured Puts vs S&P 500 Challenge. Month 4, September 2023
Cash Secured Puts vs S&P 500 Challenge. Month 5, October 2023
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 $4,751.35 — still well below where we started in June, and honestly the October results left a bit of a bruise. But rather than wallow, let’s get into it.
A New Chapter: The Great Migration
Before we even get to the trades, there’s some housekeeping to cover. Early in November, the account transferred from TD Ameritrade over to Charles Schwab as part of TDA’s ongoing integration into Schwab. Functionally not much changed for me — same positions, same general approach — but the transaction log for the month has some noise in it. You’ll see a bunch of “Internal Transfer” and “TDA TO CS&CO TRANSFER” entries scattered throughout. Don’t let those confuse you; the underlying positions and cash moved over intact. Just plumbing.
Week 1, Nov 1 – 5: The Market Finally Shows Me the Door
After months of selling covered calls on BYND, MARA, and AFRM at whatever depressed strike price I could find, collecting tiny premiums and watching them expire worthless week after week, something unexpected happened at the very end of October: all three stocks actually moved up. Not enough to recover my losses — but just enough to get called away.
On October 31st, I had sold covered calls on all three heading into the November 3rd expiration:
- MARA Nov 3 $9.50 call
- BYND Nov 3 $6.50 call (2 contracts)
- AFRM Nov 3 $19.50 call
On November 3rd, all three closed above their strike prices and were assigned. The stocks were delivered out at exactly those prices:
- MARA called away at $9.50/share → $949.98
- BYND called away at $6.50/share → $1,299.96
- AFRM called away at $19.50/share → $1,949.97
It’s a little bittersweet, honestly. I didn’t decide to cut my losses and move on — the market made that decision for me. After all those months underwater, the stocks finally moved in the right direction… just enough to trigger assignment, not enough to actually recover anything meaningful. BYND was originally purchased around $18/share and left at $6.50. That stings. But at this point, getting out at all felt like parole.
Why did these stocks drop so far in the first place? Beyond Meat ($BYND) had been in freefall for months as plant-based meat demand collapsed and the company burned through cash — it had fallen from its pandemic-era highs of over $100 all the way into the single digits. Marathon Digital ($MARA), a Bitcoin mining company, was essentially tethered to crypto prices, which had been choppy all fall. And Affirm ($AFRM), the buy-now-pay-later lender, got crushed by rising interest rates making their lending model less attractive. In hindsight, it wasn’t a great lineup. Lesson: when you sell puts on high-volatility, speculative stocks, sometimes the market’s way of saying “high premium = high risk” is… entirely correct.
The silver lining: the cash is freed up, the albatrosses are off the neck, and it’s time to find better stocks to work with.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/3/2023 | MARA called away at $9.50 (Nov 3 $9.50 call assigned) | 100 | $9.50 | $0.02 | $949.98 |
| 11/3/2023 | BYND called away at $6.50 (Nov 3 $6.50 call assigned) | 200 | $6.50 | $0.04 | $1,299.96 |
| 11/3/2023 | AFRM called away at $19.50 (Nov 3 $19.50 call assigned) | 100 | $19.50 | $0.03 | $1,949.97 |
Week 2, Nov 6 – 12: Hello CVNA, Goodbye Comfort Zone
With fresh cash from the assignments, I decided to put it to work. I introduced two new names this week.
On November 6th, I sold two puts:
- CVNA (Carvana) Nov 10 $30.50 put — collected a premium of $90.34 after fees
- AFRM Nov 10 $20.00 put — collected a premium of $98.34 after fees
Why Carvana? Well, CVNA had been one of the more interesting comeback stories of 2023. The online used car dealer had nearly gone bankrupt in 2022 when interest rates spiked and used car prices fell off a cliff. But in 2023 it started recovering as the company restructured its debt. It had already run from the low $4s in January all the way up into the $30s by November — a massive move. At $30.50, I was selling a put right at the current price (more or less), collecting a fat premium because implied volatility was still elevated from all that drama.
$90 for a single week’s put? Not bad. The AFRM put at $98 was also juicy — I still believed in the stock enough to own it again at $20 if it came to that.
But here’s the thing about juicy premiums: sometimes the market gives you that premium for a reason.
On November 9th, I bought back the AFRM put for just $1.01 — locking in almost the entire $98.34 as profit. AFRM was trading comfortably above $20. That one worked perfectly.
The CVNA put? That one had other plans. On November 10th, CVNA closed below $30.50 and I got assigned — buying 100 shares of Carvana at $30.50/share for $3,050. Carvana had pulled back a bit after earnings (the company beat expectations but gave some cautious guidance that spooked investors a bit). Getting assigned wasn’t the end of the world — I had the cash and I’d already collected that $90 premium — but now I was a Carvana shareholder, which felt more exciting than it probably should have.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/6/2023 | Sold to Open CVNA Nov 10 $30.50 Put | 1 | $0.91 | $0.66 | $90.34 |
| 11/6/2023 | Sold to Open AFRM Nov 10 $20.00 Put | 1 | $0.99 | $0.66 | $98.34 |
| 11/9/2023 | Bought to Close AFRM Nov 10 $20.00 Put | 1 | $0.01 | $0.01 | -$1.01 |
| 11/10/2023 | Assigned CVNA Nov 10 $30.50 Put → Bought 100 CVNA | 100 | $30.50 | — | -$3,050.00 |
Week 3, Nov 13 – 19: Spinning the Wheel on CVNA
Now that I owned CVNA, it was time to put the “wheel strategy” into action. The whole idea of the wheel is: sell a put → get assigned → sell a covered call → get called away → start over. With Carvana, I was right in the middle of the spin.
On November 13th, I sold two more options:
- CVNA Nov 17 $30.50 covered call — collected $59.34 after fees
- AFRM Nov 17 $21.50 put — collected $71.34 after fees
The covered call on CVNA at $30.50 was essentially offering to sell the shares right back at my cost basis. I’d make nothing on the stock itself, but I’d keep the premium. Considering the stock had just gotten choppy around earnings, locking in the premium and getting out flat seemed like a reasonable move.
Now, what happened in the broader market this week is important context. November 2023 was turning into a monster month for stocks. The S&P 500 was rallying hard on growing hopes that the Federal Reserve was done hiking interest rates — inflation data was cooling, and the market started pricing in rate cuts for 2024. Carvana, being a highly speculative, rate-sensitive stock, was catching a strong tailwind. By November 17th, the stock was trading above $30.50… which meant I was about to get called away.
Sure enough, on November 17th:
- The CVNA covered call was assigned — I sold 100 shares at $30.50, collecting $3,049.97
- The AFRM Nov 17 $21.50 put expired worthless — full $71.34 premium kept ✓
I bought the stock at $30.50, sold it at $30.50. Net on the stock: basically zero. But between the initial put premium ($90.34) and the covered call ($59.34), I collected about $150 in premiums on the CVNA wheel in two weeks. That’s the strategy working as designed. I’ll take it.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/13/2023 | Sold to Open CVNA Nov 17 $30.50 Call | 1 | $0.60 | $0.66 | $59.34 |
| 11/13/2023 | Sold to Open AFRM Nov 17 $21.50 Put | 1 | $0.72 | $0.66 | $71.34 |
| 11/17/2023 | Expired AFRM Nov 17 $21.50 Put | 1 | — | — | — |
| 11/17/2023 | Assigned CVNA Nov 17 $30.50 Call → Sold 100 CVNA | 100 | $30.50 | $0.03 | $3,049.97 |
Week 4, Nov 20 – 26: Back on the Horse. The Same Horse.
You’d think after a week of successfully spinning the CVNA wheel I might try something different. Instead, I just… got right back on.
On November 20th:
- MARA Nov 24 $10.00 puts (2 contracts) — collected $46.68 after fees
- CVNA Nov 24 $31.50 put — collected $66.34 after fees
Why CVNA again? Because Carvana was continuing its rally — the broader market was surging with the rate-cut narrative, and CVNA was flying. The $31.50 strike was slightly above where I’d been trading it, so I’d pocket a little extra if it stayed there. MARA was back in the mix too — Bitcoin had been gaining momentum through November (BTC crossed $37,000 for the first time since early 2022), which was lifting MARA’s stock price. The puts seemed reasonable.
Thanksgiving week, the market was quiet. And when November 24th arrived:
- The MARA puts expired worthless — full $46.68 premium collected. MARA was well above $10. ✓
- The CVNA put was assigned again — I bought another 100 shares at $31.50 for $3,150. Carvana just couldn’t stay above the strike.
So I’m back to being a Carvana shareholder. Again. It’s like a bad ex you keep texting.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/20/2023 | Sold to Open MARA Nov 24 $10.00 Puts (x2) | 2 | $0.24 | $1.32 | $46.68 |
| 11/20/2023 | Sold to Open CVNA Nov 24 $31.50 Put | 1 | $0.67 | $0.66 | $66.34 |
| 11/24/2023 | Expired MARA Nov 24 $10.00 Puts | 2 | — | — | — |
| 11/24/2023 | Assigned CVNA Nov 24 $31.50 Put → Bought 100 CVNA | 100 | $31.50 | — | -$3,150.00 |
Week 5, Nov 27 – 30: Setting Up for December
With CVNA shares in hand heading into the final days of November, I set up a few trades to carry into December. On November 27th I sold three options:
- CVNA Dec 1 $32.00 covered call — collected $101.34 after fees. A full dollar above my cost basis — if this gets called away, I actually make a little money on the stock for once!
- RIVN Dec 1 $16.50 put — collected $38.34 after fees. Rivian had been bouncing around in the mid-teens, and a short-dated put seemed reasonable.
- VOD (Vodafone) Dec 15 $9.00 put — collected $16.34 after fees. A longer-dated, conservative play on the British telecom giant. Not exciting, but Vodafone’s stock had been sluggish and the $9 strike was well below where it was trading.
These three trades carry into December so we’ll pick up the results there.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/27/2023 | Sold to Open CVNA Dec 1 $32.00 Call | 1 | $1.02 | $0.66 | $101.34 |
| 11/27/2023 | Sold to Open RIVN Dec 1 $16.50 Put | 1 | $0.39 | $0.66 | $38.34 |
| 11/27/2023 | Sold to Open VOD Dec 15 $9.00 Put | 1 | $0.17 | $0.66 | $16.34 |
November 2023 Trades Summary
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 11/3/2023 | MARA called away at $9.50 (Nov 3 call assigned) | 100 | $9.50 | $0.02 | $949.98 |
| 11/3/2023 | BYND called away at $6.50 (Nov 3 call assigned) | 200 | $6.50 | $0.04 | $1,299.96 |
| 11/3/2023 | AFRM called away at $19.50 (Nov 3 call assigned) | 100 | $19.50 | $0.03 | $1,949.97 |
| 11/6/2023 | Sold to Open CVNA Nov 10 $30.50 Put | 1 | $0.91 | $0.66 | $90.34 |
| 11/6/2023 | Sold to Open AFRM Nov 10 $20.00 Put | 1 | $0.99 | $0.66 | $98.34 |
| 11/9/2023 | Bought to Close AFRM Nov 10 $20.00 Put | 1 | $0.01 | $0.01 | -$1.01 |
| 11/13/2023 | Sold to Open CVNA Nov 17 $30.50 Call | 1 | $0.60 | $0.66 | $59.34 |
| 11/13/2023 | Sold to Open AFRM Nov 17 $21.50 Put | 1 | $0.72 | $0.66 | $71.34 |
| 11/17/2023 | Assigned CVNA Nov 17 $30.50 Call → Sold 100 CVNA | 100 | $30.50 | $0.03 | $3,049.97 |
| 11/20/2023 | Sold to Open MARA Nov 24 $10.00 Puts (x2) | 2 | $0.24 | $1.32 | $46.68 |
| 11/20/2023 | Sold to Open CVNA Nov 24 $31.50 Put | 1 | $0.67 | $0.66 | $66.34 |
| 11/24/2023 | Assigned CVNA Nov 24 $31.50 Put → Bought 100 CVNA | 100 | $31.50 | — | -$3,150.00 |
| 11/27/2023 | Sold to Open CVNA Dec 1 $32.00 Call | 1 | $1.02 | $0.66 | $101.34 |
| 11/27/2023 | Sold to Open RIVN Dec 1 $16.50 Put | 1 | $0.39 | $0.66 | $38.34 |
| 11/27/2023 | Sold to Open VOD Dec 15 $9.00 Put | 1 | $0.17 | $0.66 | $16.34 |
| Totals (premiums only) | $587.03 |
The total option premium collected of $587.03 was honestly the best premium month of the challenge so far. On the $4,751.35 starting balance that represents about 12.35% in premiums for the month — which sounds great until you remember that a large chunk of that cash got redeployed into CVNA stock via assignment. That’s not a loss, just tied up capital. Either way, the premium machine was humming in November even if the overall picture is still a work in progress.
S&P 500 (VOO) Summary Activity and Results
Oh boy. This is the part where I have to report that the S&P 500 had an absolutely ripping month while I was busy doing broker transfers and getting assigned on Carvana puts.
VOO started November at roughly $384.17 (October 31 close) and closed the month at $419.40. That’s a gain of $35.23 per share, or +9.18% in a single month. To put that in perspective, the S&P 500 had one of its best Novembers in years. The catalyst was a one-two punch: a Federal Reserve that seemed to be done hiking rates, and cooling inflation data. Investors piled back into stocks like it was 2021 again.
If nothing else, at least the S&P 500 is finally going back up. For the VOO benchmark account, starting with 15.738 shares (where we left off after the September dividend reinvestment), that November surge brought the total value to approximately $6,597.21.
| Date | Activity | Cash In/Out | Share Price | Shares | Total Shares | Total Value |
|---|---|---|---|---|---|---|
| 10/31/2023 | Month Closing Price | $0.00 | $384.17 | — | 15.738 | $6,046.70 |
| 11/30/2023 | Month Closing Price | $0.00 | $419.40 | — | 15.738 | $6,597.21 |
A 9.18% single-month gain for the benchmark is a tough act to follow. When the market rips like that, a strategy that has a big chunk of cash tied up in assigned stock — and whose premiums are capped — simply can’t keep up on a percentage basis. This is one of the known trade-offs of the wheel strategy: you collect income steadily, but you give up some of the explosive upside when the market surges. That’s fine in theory. It stings a little in practice.
Month End Results on Live Account
It’s now been 6 months and somehow it feels like both forever and not very long at all. The three problem positions — BYND, MARA, and AFRM — are finally off the books, not because I made a brilliant strategic decision, but because the market quietly moved them up just enough to trigger assignment on a November Friday. I didn’t pull the trigger. The strategy did. That’s humbling, in a weirdly good way.
The account now holds 100 shares of CVNA (purchased at $31.50, with a covered call at $32 expiring Dec 1) plus cash. The live account value at month-end came in at $5,652.56. The account is still trailing its $6,000 starting value, but the trajectory is genuinely improving. Think of November as the month the patient got out of the ICU and into a regular room — not healed, but no longer in crisis.
Final Comparison
| 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 | $6,046.70 | -2.16% | +0.78% | $4,751.35 | -13.56% | -20.81% |
| 11/30/23 | $6,597.21 | +9.18% | +9.95% | $5,652.56 | +18.97% | -5.79% |
Ending Thoughts
November 2023 was genuinely encouraging, even if I’m still in the hole overall. The three anchors are gone. New positions are cleaner and generating real premium. And for the first time in a few months, I actually feel like I have some momentum going into the next month rather than just hoping for survival.
That said, the VOO account is now back above $6,600 — meaning it’s up nearly 10% since the start of the challenge — and my live account closed the month at $5,652.56. That’s a gap of about $945 that I’ve got to make up. The market’s best month in a long time came at exactly the moment when my strategy is best positioned to keep up, and yet the gap is still wide.
The CVNA wheel is interesting. It’s a high-volatility name that pays well in premiums but loves to get puts assigned right when you think it won’t. Sound familiar? I’ll keep spinning it into December and see what happens.
The strategy isn’t broken — it’s just slow, humbling, and a constant reminder that the market doesn’t care about your feelings. I’m still here, still trading, still weirdly committed to this whole thing. See you in December.
