VOO had a great February. Me? I collected $356 and got assigned a crypto miner. So that’s fun.
Welcome back to another installment of the challenge where I pit my options-selling strategy against the boring, reliable S&P 500 — and then report back on exactly how many ways I found to make it complicated. If you’re new here, the short version: I deposited $6,000 into a Roth IRA back in June 2023, and every month I sell cash-secured puts and covered calls (a strategy known as the Wheel) to try to generate income. At the same time, I track what that same $6,000 would be worth if I’d just bought shares of VOO — the Vanguard S&P 500 ETF — and done absolutely nothing.
Also, before we get too far: 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 you to copy these trades. 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 quick recap of how this challenge works. I started with $6,000 and I’m selling cash-secured puts or covered calls to collect the premiums and measure that against the performance of shares of VOO. I post all the trades I made each week along with my thoughts along the way. Each month I compare it to the performance of the shares in VOO and keep a running cumulative score of both accounts. So here we go again.
You can catch up on previous months here:
- Month 1, June 2023
- Month 2, July 2023
- Month 3, August 2023
- Month 4, September 2023
- Month 5, October 2023
- Month 6, November 2023
- Month 7, December 2023
- Month 8, January 2024
To start the month I am beginning from an account value of $6,009.56. After a rough January that clawed back most of December’s gains, we’re basically back to where we started the whole challenge nine months ago. That stings a little, but the premium machine never stops — let’s see what February had in store.
Week 1, February 1–3
February started quietly. The only things happening in Week 1 were two options from January expiring worthless — which is actually the good outcome when you’re the seller. The AFRM (Affirm Holdings) covered call at $48.00 that expired on February 2nd went out worthless, meaning Affirm’s stock price stayed below $48 and I kept the full premium I collected when I sold it. Same story for a put I’d sold on RIOT Platforms (a crypto-focused stock) at an $11 strike — it expired on February 2nd with RIOT trading above $11, so that one dissolved cleanly too.
No new trades this week. Sometimes the best thing you can do is sit on your hands and let the clock run out in your favor.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/2/2024 | CALL AFFIRM HLDGS INC $48 EXP 02/02/24 — Expired | 1 | — | — | — |
| 2/2/2024 | PUT RIOT PLATFORMS INC $11 EXP 02/02/24 — Expired | 1 | — | — | — |
Week 2, February 4–10
With both positions cleared off the board, it was time to put the AFRM shares back to work. Affirm had been on a wild ride — the buy-now-pay-later fintech had seen its stock price collapse from highs above $90 in mid-2023 all the way down toward the $20s by late summer, before recovering somewhat. At this point I was still holding 100 shares after being assigned back in January, so the playbook was to keep selling covered calls above my cost basis and collect premiums while I waited.
On February 5th, with AFRM trading in the upper $40s, I sold a covered call with a strike price of $48.50 expiring February 9th and collected $106.34 in premium after fees. A covered call, for anyone new to this, is when you own 100 shares of a stock and sell someone else the right to buy those shares from you at a specific price (the strike price) by a specific date (the expiration). You collect the premium upfront. If the stock stays below the strike, you keep the premium and your shares. If it goes above, your shares get “called away” and sold at the strike price — which isn’t the end of the world, it just means you’ve capped your upside.
$106 in a week on AFRM was a solid haul. Affirm’s earnings were coming up and there was still elevated implied volatility in the options market — meaning traders were expecting big price swings, and that uncertainty gets priced into the premiums you can collect as a seller. I was happy to take the other side of that bet.
Sure enough, AFRM stayed below $48.50 through Friday the 9th and the call expired worthless. Another clean expiration.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/5/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/09/24 — Sell to Open | 1 | $1.07 | $0.66 | $106.34 |
| 2/9/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/09/24 — Expired | 1 | — | — | — |
Week 3, February 11–17
Week 3 was the busiest of the month — four trades across three different tickers, and one of them took an unexpected turn by the end of the week.
On February 12th I opened two new positions. First, another AFRM covered call — this time also at $48.50 but expiring February 16th — collecting $87.34. The premium was a bit lower than the week before, which makes sense because I had a shorter window (4 days vs. 4 days, roughly), and the implied volatility was starting to cool off a little. Still, $87 for four days of waiting is hard to argue with.
The second trade was a cash-secured put on Robinhood Markets (HOOD) at an $11 strike, also expiring February 16th, for $34.34. A cash-secured put means I’m agreeing to buy 100 shares of HOOD at $11 if it drops to that level by expiration. In exchange I collect the premium now. Robinhood had been bouncing around in the $10–$13 range and with crypto sentiment picking up — more on that in a second — I thought HOOD had some support. The $11 strike gave me a little cushion below where it was trading.
February 15th brought a tiny $0.43 in bank interest. Every penny counts, right?
By February 16th — expiration Friday — a couple of things happened. The HOOD put had essentially gone to zero in value since HOOD was trading comfortably above $11, so rather than let it expire I bought it back for a penny ($1.01 including fees) just to clean it off the books. The net on that HOOD trade: $34.34 collected, $1.01 paid to close = $33.33 profit. Not life-changing, but clean.
The AFRM $48.50 call also expired worthless on the 16th — another good outcome. Affirm had actually reported earnings on February 7th and the stock popped hard initially, running up close to $50, but then faded back below the strike by expiration. Affirm beat analysts’ expectations on revenue and raised guidance, but the market’s initial enthusiasm cooled as investors processed the details. That fade saved me from having my shares called away — sometimes you get lucky with the timing.
Also on the 16th, I sold a new put on HUT 8 Corp (ticker HUT) — a Canadian Bitcoin mining company — at a $9.50 strike expiring February 23rd, collecting $59.34. This is where the story gets interesting for next week. February 2024 was a remarkable month for crypto. Bitcoin was running hard toward what would eventually be a new all-time high in March, and crypto-adjacent stocks like HUT, MARA, and RIOT were all catching a massive bid. HUT had been trading around $10–$12 and I thought a $9.50 put was safely out of the money. I was about to find out what “safely” means in crypto stocks.
There was also a VOD (Vodafone) covered call expiration on the 16th — the $9 strike call I’d sold in January expired worthless, which is what I wanted. VOD had been drifting lower all year and I was just trying to squeeze premiums out of it while it figured itself out.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/12/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/16/24 — Sell to Open | 1 | $0.88 | $0.66 | $87.34 |
| 2/12/2024 | PUT ROBINHOOD MKTS INC $11 EXP 02/16/24 — Sell to Open | 1 | $0.35 | $0.66 | $34.34 |
| 2/15/2024 | Bank Interest | — | — | — | $0.43 |
| 2/16/2024 | PUT ROBINHOOD MKTS INC $11 EXP 02/16/24 — Buy to Close | 1 | $0.01 | $0.01 | ($1.01) |
| 2/16/2024 | PUT HUT 8 CORP $9.5 EXP 02/23/24 — Sell to Open | 1 | $0.60 | $0.66 | $59.34 |
| 2/16/2024 | CALL VODAFONE GROUP $9 EXP 02/16/24 — Expired | 1 | — | — | — |
| 2/16/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/16/24 — Expired | 1 | — | — | — |
Week 4, February 18–24
Remember that HUT put I sold, the one with the “safely out of the money” $9.50 strike? Yeah. About that.
The week started with Presidents’ Day on Monday the 19th — markets closed, nothing to do. On Tuesday the 20th I rolled out a new VOD covered call, selling the March 15th $9.00 call for $29.34. Vodafone has been the slow, quiet corner of this account — I keep selling calls on it, they keep expiring worthless, and the stock keeps drifting lower. It’s like renting out a house that’s slowly losing value. Not great, but not nothing.
Then came February 23rd. HUT 8 had been flying high when Bitcoin was ripping higher, but crypto is a two-way street. During the week, Bitcoin pulled back from its recent highs and HUT got caught in the downdraft, dropping below $9.50. When a cash-secured put expires in-the-money — meaning the stock is below your strike price — you get assigned. That’s the technical term for what happens: the put is assigned to you, and you are obligated to buy 100 shares at the strike price, regardless of where the stock is currently trading.
So on February 23rd, I was assigned on the HUT put and bought 100 shares of HUT 8 Corp at $9.50 per share — a total outlay of $950.00. The good news? I’d already collected $59.34 in premium when I sold the put, which brings my effective cost basis down to roughly $8.91 per share. The bad news? I now owned 100 shares of a Bitcoin mining company right as crypto was getting choppy. Welcome to the portfolio, HUT.
This is exactly how the Wheel strategy is supposed to work — you sell puts on stocks you wouldn’t mind owning, and if you get assigned, you pivot to selling covered calls to generate income while you wait for the stock to recover. The key question is always: do you still like the stock at this price? At $9.50 for a Bitcoin miner heading into what looked like a strong crypto cycle, I decided I was okay with it. Time to spin the wheel to the other side.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/20/2024 | CALL VODAFONE GROUP $9 EXP 03/15/24 — Sell to Open | 1 | $0.30 | $0.66 | $29.34 |
| 2/23/2024 | PUT HUT 8 CORP $9.5 EXP 02/23/24 — Assigned | 1 | — | — | — |
| 2/23/2024 | HUT 8 CORP — Buy (Assignment) | 100 | $9.50 | — | ($950.00) |
Week 5, February 25–29
With 100 shares of HUT now sitting in the account, the immediate next step was to sell a covered call and start generating income from the new position. On February 26th I sold the March 1st $9.50 call on HUT, collecting $40.34 in premium. The strike is right at my cost basis, which means if HUT gets called away on March 1st I’ll essentially break even on the shares — but I’ll have banked both the original $59.34 put premium and this $40.34 call premium along the way. That’s $99.68 in total premium from one full wheel cycle on HUT, which feels decent given the assignment.
February 29th was the last trading day of the month — 2024 being a leap year and all. A small silver lining in an otherwise modest month.
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/26/2024 | CALL HUT 8 CORP $9.5 EXP 03/01/24 — Sell to Open | 1 | $0.41 | $0.66 | $40.34 |
S&P 500 (VOO) Summary Activity and Results
February 2024 was a great month to own the S&P 500 and do nothing. VOO opened the month at $443.82 (January 31st close) and closed February 29th at $466.93 — a gain of 5.21% in a single month. The market had a lot to feel good about: the economy was proving more resilient than the bears expected, corporate earnings were coming in strong, and the excitement around artificial intelligence continued to push the big tech names that dominate the S&P 500 to new heights. Nvidia in particular had an absolutely staggering earnings report in late February that sent the stock up over 16% in a single day and lifted the whole index. When your benchmark has Nvidia in it, February was a very good time to be passive.
There were no VOO dividends in February — VOO pays quarterly, with distributions typically falling in March, June, September, and December — so the share count stays at 15.804 shares.
| Date | Activity | Cash In/Out | Share Price | Shares | Total Shares | Total Value |
|---|---|---|---|---|---|---|
| 5/31/23 | Initial Purchase | $6,000.00 | $383.89 | 15.628 | 15.628 | $6,000.00 |
| 6/22/23 | Dividend Reinvest | $23.88 | $407.93 | 0.059 | 15.687 | — |
| 6/30/23 | End of Month | — | $407.28 | — | 15.687 | $6,364.94 |
| 7/31/23 | End of Month | — | $420.68 | — | 15.687 | $6,599.11 |
| 8/31/23 | End of Month | — | $413.83 | — | 15.687 | $6,491.80 |
| 9/27/23 | Dividend Reinvest | $24.08 | $390.91 | 0.062 | 15.749 | — |
| 9/29/23 | End of Month | — | $392.70 | — | 15.749 | $6,160.09 |
| 10/31/23 | End of Month | — | $384.17 | — | 15.749 | $6,051.43 |
| 11/30/23 | End of Month | — | $419.40 | — | 15.749 | $6,605.11 |
| 12/21/23 | Dividend Reinvest | $25.22 | $455.38 | 0.055 | 15.804 | — |
| 12/29/23 | End of Month | — | $436.80 | — | 15.804 | $6,903.19 |
| 1/31/24 | End of Month | — | $443.82 | — | 15.804 | $7,014.13 |
| 2/29/24 | End of Month | — | $466.93 | — | 15.804 | $7,379.36 |
Month End Results on Live Account
The live account opened February at $6,009.56 and closed at $6,019.08 — a gain of $9.52, or 0.16%. That’s not a typo. Nine dollars and fifty-two cents on the month.
To be fair, the $9.52 gain at the account level doesn’t tell the whole story of what happened. I collected $356.46 in net premium during the month ($357.47 in gross premium income, minus $1.01 to buy back the HOOD put). That’s actually a pretty solid month of income generation from options. The problem is that the account also absorbed the $950 purchase of HUT 8 shares via assignment — cash that went from sitting as buying power to sitting as shares. The shares are still in the account, they’re just sitting at roughly their purchase price, so the account value didn’t move much on net. The month’s story is really: I generated good premium income, got assigned a new position, and now have HUT going into March.
Heading into March, the open positions are: 100 shares of AFRM with no call currently open on them, 100 shares of HUT with a $9.50 covered call expiring March 1st, and 100 shares of VOD with a $9.00 covered call expiring March 15th. Lots of irons in the fire.
February 2024 Trade Summary:
| Date | Description | Qty | Price | Fees & Comm | Amount |
|---|---|---|---|---|---|
| 2/2/2024 | CALL AFFIRM HLDGS INC $48 EXP 02/02/24 — Expired | 1 | — | — | — |
| 2/2/2024 | PUT RIOT PLATFORMS INC $11 EXP 02/02/24 — Expired | 1 | — | — | — |
| 2/5/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/09/24 — Sell to Open | 1 | $1.07 | $0.66 | $106.34 |
| 2/9/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/09/24 — Expired | 1 | — | — | — |
| 2/12/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/16/24 — Sell to Open | 1 | $0.88 | $0.66 | $87.34 |
| 2/12/2024 | PUT ROBINHOOD MKTS INC $11 EXP 02/16/24 — Sell to Open | 1 | $0.35 | $0.66 | $34.34 |
| 2/15/2024 | Bank Interest | — | — | — | $0.43 |
| 2/16/2024 | PUT ROBINHOOD MKTS INC $11 EXP 02/16/24 — Buy to Close | 1 | $0.01 | $0.01 | ($1.01) |
| 2/16/2024 | PUT HUT 8 CORP $9.5 EXP 02/23/24 — Sell to Open | 1 | $0.60 | $0.66 | $59.34 |
| 2/16/2024 | CALL VODAFONE GROUP $9 EXP 02/16/24 — Expired | 1 | — | — | — |
| 2/16/2024 | CALL AFFIRM HLDGS INC $48.5 EXP 02/16/24 — Expired | 1 | — | — | — |
| 2/20/2024 | CALL VODAFONE GROUP $9 EXP 03/15/24 — Sell to Open | 1 | $0.30 | $0.66 | $29.34 |
| 2/23/2024 | PUT HUT 8 CORP $9.5 EXP 02/23/24 — Assigned | 1 | — | — | — |
| 2/23/2024 | HUT 8 CORP — Buy (Assignment) | 100 | $9.50 | — | ($950.00) |
| 2/26/2024 | CALL HUT 8 CORP $9.5 EXP 03/01/24 — Sell to Open | 1 | $0.41 | $0.66 | $40.34 |
Final Comparison
Let’s just get this out of the way: VOO had a phenomenal February. A 5.21% single-month gain is well above average — even for a year that would go on to be quite strong for the index. My account gained 0.16%. Those two numbers next to each other are a little humbling.
Cumulatively, VOO is now sitting at $7,379.36 — up 22.99% from the original $6,000. The live account is at $6,019.08 — up just 0.32%. VOO is ahead by $1,360.28, and that gap widened significantly this month. The strategy has generated real premium income — $356 in February alone — but when your benchmark rips 5% in a month, premium income from options can’t keep pace. That’s just the math of it.
It’s worth being honest about what’s happening here: the stocks I’ve been running the Wheel on (AFRM, VOD, HUT, BYND) have had a rough time as individual names while the broad index has been carried higher by mega-cap tech. The Wheel works best when your underlying stocks are also appreciating, or at least holding value. When they’re dragging, you’re essentially running on a treadmill — generating income with one hand while watching unrealized losses on the other.
| 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 | $6,364.94 | +6.08% | +6.08% | $6,072.00 | +1.20% | +1.20% |
| 7/31/23 | $6,599.11 | +3.68% | +9.99% | $6,051.67 | -0.33% | +0.86% |
| 8/31/23 | $6,491.80 | -1.63% | +8.20% | $6,153.84 | +1.69% | +2.56% |
| 9/29/23 | $6,160.09 | -5.11% | +2.67% | $6,132.29 | -0.35% | +2.20% |
| 10/31/23 | $6,051.43 | -1.76% | +0.86% | $6,007.87 | -2.03% | +0.13% |
| 11/30/23 | $6,605.11 | +9.15% | +10.08% | $6,263.07 | +4.25% | +4.38% |
| 12/29/23 | $6,903.19 | +4.51% | +15.05% | $6,470.21 | +3.31% | +7.84% |
| 1/31/24 | $7,014.13 | +1.61% | +16.90% | $6,009.56 | -7.12% | +0.16% |
| 2/29/24 | $7,379.36 | +5.21% | +22.99% | $6,019.08 | +0.16% | +0.32% |
Ending Thoughts
February was a tale of two accounts. VOO had one of its best single months of the entire challenge, riding the AI wave and a broad market that just refused to quit. Meanwhile, I collected a respectable $356 in premium, got assigned on a crypto miner, and ended the month up $9.52. There is something almost poetic about grinding through five weeks of trades to net less than a decent lunch.
But here’s the thing I keep reminding myself: the Wheel strategy isn’t a moon-shot. It’s an income strategy. The goal is to grind out consistent premium income month after month and hopefully outperform over a full cycle — including the months when the market pulls back and VOO loses ground. February 2024 was not that month. Not even close.
What I’m watching heading into March: HUT 8 is the most interesting wildcard. Bitcoin has been on a tear and the halving is coming in April, which historically has been a catalyst for crypto prices. If HUT gets called away on March 1st at $9.50 I’ll take the break-even on the shares plus pocket the premiums, and then decide if I want back in. If it drops, I keep the shares and sell another call. Either way, the Wheel keeps spinning.
AFRM and VOD are the ongoing sagas. Affirm is a company I actually believe in long-term, but the stock has been frustrating to hold. VOD is more of a “how long do I babysit this thing” situation at this point. March should be interesting. Stick around.