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Wheel strategy IRR vs buy-and-hold performance breakdown

This is from a reddit thread - can you explain - his account summary, and IRR from option selling vs from long? Skip to main content Week 26 $502 in premium : r/thetagang r/thetagang Search in ⁨r/thetagang⁩ Advertise on Reddit Open chat Create Create post Open inbox User Avatar Expand user menu Skip to NavigationSkip to Right Sidebar Back Go to thetagang r/thetagang • 2mo ago Expired_Options Week 26 $502 in premium r/thetagang - Week 26 $502 in premium I will post a separate comment with a link to the detail behind each option sold this week. After week 26, the average premium per week is $759 with an annual projection of $39,464. All things considered, the portfolio is up $9,019 (+2.01%), on the year (S&P 500: +7.43% | Nasdaq: +8.84%). Additionally, the trailing 1-year performance is up $49,046 (+11.97%); for comparison the S&P 500 is +19.75% and the Nasdaq is +25.43% over the same period. This is the overall profit and loss and includes options and all other account activity. Annual results: • 2023 up $65,403 (+41.31%) | S&P 500: +26.3% | Nasdaq: +43.4% • 2024 up $64,610 (+29.71%) | S&P 500: +25.0% | Nasdaq: +28.6% • 2025 up $111,496 (+34.52%) | S&P 500: +17.9% | Nasdaq: +20.4% 3-Year Cumulative (2023–2025): • r/ExpiredOptions: +146.6% ($241,509) • S&P 500: +86.1% (+60.4% behind) • Nasdaq: +122.0% (+24.5% behind) Options: • YTD: $26,205.00 • 1 Month: $7,438.00 • 1 Week: $1,367.00 Realized P&L: • YTD: $24,617.83 • 1 Month: $2,510.00 • 1 Week: $3,208.00 All options sold are backed by cash, shares, or LEAPS. I do not sell on margin, nor do I sell naked options. All options and profits stay in the account with few exceptions. This is not my full time job, although I wish it was. I still grind on a 9-5. My $600 weekly contribution streak is at 18 weeks, but I am pausing new contributions until next month. The portfolio is comprised of 101 unique tickers, unchanged from 101 last week. These 101 tickers have a value of $416k. I also have 191 open option positions, down from 194 last week. The options have a total value of $43k. The total of the shares and options is $459k. The next goal on the "Road to" is Half a Million. I'm currently utilizing $37,050 in cash secured put collateral, down from $39,650 last week. 2025 through 2028 LEAPS In addition to the CSPs and covered calls, I purchase LEAPS. These act as collateral to sell covered calls against. You may have heard of poor man's covered calls (PMCC). See r/ExpiredOptions for a detailed spreadsheet update on all LEAPS positions including P/L for each individual position. LEAPS note 1: the 2025 LEAPS expired 1/17/25. They were up $36,440 overall with a 233.74% increase. The major drivers were AMZN and CRWD. LEAPS note 2: After holding for 2 years, I exercised an AMZN $80 strike from 2023 up +$11,395 (+463.21%) and CRWD $95 strike from 2023, up +$21,830 (+663.53%) LEAPS note 3: Purchased 1/16/26 CRWD LEAPS for $8,230.03 on 1/17/24. I sold this LEAPS on 6/5/25 for $21,659 for a realized profit of $13,428.97 (+163.18%) Total premium by year: • 2023 $23,132 in premium • 2024 $47,640 in premium • 2025 $68,319 in premium • 2026 $19,732 YTD • Average $46,364/year (completed years) Premium by month (2026): • January $3,334 • February $3,625 • March $465 • April $5,593 • May $3,787 • June $2,927 • Average $3,289/month I am over $163k in total options premium, since 2021. I average roughly $35 per option sold. I have sold over 4k options. I have been able to increase the premiums on an annual basis and I will attempt to keep this upward trend going forward. Strategy: The underlying strategy is buy and hold. I also use simple 1-legged options to supplement that strategy. Options have somewhat of a learning curve, but I believe that most people can supplement their investments using simple options with careful risk management. I sell options on a weekly basis. I prefer cash secured puts and covered calls. I rarely close early, prefer rolling when needed, and let time decay do the heavy lifting while I stay focused on quality companies, patience, and consistency over hype. My goal is consistency in option premium revenue. I am building an income stream that will continue long into retirement. Spreadsheets: Unfortunately, I no longer provide spreadsheets. I received too many follow ups about formatting, pivot tables, compatibility etc. I think tracking is very important, but I post to discuss investing and options, not to provide tech support for Excel. I do appreciate the interest in my tracking methods. Software: I captured the screen shots from a proprietary software platform I built to track, analyze, and manage my options strategies. Commissions: I use Robinhood as a broker and they do not charge explicit commissions, though there is no free lunch — they earn revenue through Payment for Order Flow (PFOF), which can mean slightly less optimal fills. For my style of selling options and not chasing prices, the tradeoff is acceptable. There is also a small regulatory fee of approximately $0.03–$0.04 per contract (FINRA TAF, OCC clearing, and exchange fees combined). The premiums have increased significantly as my experience has expanded over the last three years. Make sure to post your wins. I look forward to reading about them! Disclaimer: I am not a financial advisor. This information is for educational and entertainment purposes only. Trading options involves significant risk. Upvote 32 Downvote 44 Go to comments Repost Share Join the conversation Sort by: Best Search Comments Expand comment search Comments Section Cri317 • 2mo ago Curious if OP you’ve considered wheeling or selling prem on ETF like SPY? Or QQQ? with your size even wheeling ETF would yield more and less risky than picking stocks. I’m sure you’ve been asked before so trying to understand your logic Upvote 3 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Wheeling SPY or QQQ is a great grind, but the implied volatility (IV) is low. The premium is thin, meaning you have to tie up a decent amount of capital to move the needle. I’d rather chase alpha by selectively selling premium on high-conviction individual stocks where the IV is a bit higher and a bit better capital efficiency. Plus, if the macro environment dumps, the broad indexes take a hit anyway. I'd rather manage risk through sizing on single names I know fairly well. There is nothing wrong with wheeling on ETFs and I have thought about it, it just does not fit my personal preferences. Upvote 3 Downvote Reply Award Share MaximBrutii • 2mo ago When you say you’re selling options on a weekly basis, are you selling monthlies every week? Or are you selling weekly options every week? Upvote 3 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago I prefer same or subsequent week options, but do mix in monthlies. Upvote 3 Downvote Reply Award Share u/Tmdngs avatar Tmdngs • 2mo ago OP, ignore the haters. You are doing great and I envy your consistency! 💯 Upvote 5 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Appreciate the comments. I've been posting since 2023 and have no plans to stop. This whole experience has been interesting. People coming to hate on me for no apparent reason. I do my own thing and just don't interact with things I don't like. Seems like a waste of time to interact with things you don't like, but here they are wasting their time... Upvote 3 Downvote Reply Award Share FAMUgolfer • 2mo ago Are you working with 460k total? So if you sold everything you would have 460k cash? If this is true you can do way more in premiums in CSPs. Upvote 6 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Thanks for the comments. I am working with $460k. If I sold everything, I would have an enormous tax bill. Not sure where I would end up after that overhaul of my current strategy, but it is not just about premiums. Those are secondary to the buy and hold process that I am running. Upvote 2 Downvote Reply Award Share FAMUgolfer • 2mo ago • Edited 2mo ago Except CSPs is all about the premiums though which you are playing. And you’ve had most of these stocks for over a year which would lower your tax burden. So your tax burden is the same regardless. Not a hater, but this is so much movement for only $500 in weekly premiums. Upvote 6 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Did not think you were hating, I'm just more about the buy and hold. I don't stress about the options, I don't need stocks to go a certain direction, they go up and they go down and I try to capitalize on that movement. I am trying to pick long term winners. I agree that $500 is not that much for a week, but there will be plenty of $1,000+ weeks. Also, the premiums are down a bit this year, again, not too worried about it. I have been a bit more conservative with them. Upvote 1 Downvote Reply Award Share FAMUgolfer • 2mo ago Even $1000 with your portfolio is pretty weak. For instance I see you sold puts on QBTS. I love quantum stocks too because their premiums have been juicy for over a year. 7/2 $20p are $0.20. You could use half your portfolio for 100 contracts and collect $2k. Upvote -1 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago True, I could do that. Just playing devils advocate, what if quantum takes a dive and half my portfolio is now a falling knife? Upvote 7 Downvote Reply Award Share FAMUgolfer • 2mo ago u/Paddle_Billing avatar u/Paddle_Billing • Promoted Originally, Kaleido users could only pay in US dollars. When it started to support the payment norms and preferences of users in different locations, it saw a 51% increase in conversions. Localization works. Learn More paddle.com Thumbnail image: Originally, Kaleido users could only pay in US dollars. When it started to support the payment norms and preferences of users in different locations, it saw a 51% increase in conversions. Localization works. Scannerguy3000 • 2mo ago I’ve never seen anyone work so hard to make less than 1% a month. Upvote 9 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago 2.53% over three years > 1% per month. I get it, you don't like work. So, I'm going to do the work for you. You are obviously focussed on the short term, but if you are honest with yourself, I have been outperforming since I started posting in 2023. Unlike any percentage you could tell me you produce, I have posted every Friday (with a couple exceptions) for roughly 156 weeks. Annual results: • 2023 up $65,403 (+41.31%) | S&P 500: +26.3% | Nasdaq: +43.4% • 2024 up $64,610 (+29.71%) | S&P 500: +25.0% | Nasdaq: +28.6% • 2025 up $111,496 (+34.52%) | S&P 500: +17.9% | Nasdaq: +20.4% 3-Year Cumulative (2023–2025): • r/ExpiredOptions: +146.6% ($241,509) • S&P 500: +86.1% (+60.4% behind) • Nasdaq: +122.0% (+24.5% behind) r/ExpiredOptions**:** ~2.53% per month (Avg. to reach +146.6%) Nasdaq: ~2.25% per month (Avg. to reach +122.0%) S&P 500: ~1.74% per month (Avg. to reach +86.1%) Upvote 5 Downvote Reply Award Share Scannerguy3000 • 1mo ago Your words burried in all that garbage. “After week 26, the average premium per week is $759”. And you say you have $460k. $759 / $460k = 0.165% Zero percent a month. Point one, of one percent. And you’re putting in $600 a week. I’ve never seen a worse portfolio. If there’s errors here, it’s because you just vomit dozens of numbers that don’t mean anything. If someone makes a yield, or a daily take, they just post that. If you don’t have anything worth posting, machine gun ‘em with bullshit. Upvote 1 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 1mo ago It is not my problem that you don't take the time to read the write-up and dismiss it as garbage/vomit. For someone who does not like to read or do any work, you sure do waste a lot of your time admiring my work. Keep hating and best of luck to whatever it is that you do. Upvote 1 Downvote Reply Award Share Scannerguy3000 • 1mo ago Thanks. What I do is make $800 a day. Upvote 1 Downvote Reply Award Share u/Outside-Cup-1622 avatar Outside-Cup-1622 • 2mo ago GOOD GOING EXPIRED OPTIONS !!! Based on your portfolio balance, your weekly contributions and adding in the average 40 year return of the S&P I project your portfolio will hit $1,000,000 in Oct of 2031 I added $500 cash to my accounts this week and have added $13,705 so far in 2026. This continues my weekly deposit streak to 2 years and 51 weeks. I am DOWN $14,450 (-1.03%) across all accounts this week and have moved a little further away from my 1.5M goal. May all your holdings be green (or red enough to buy more) Enjoy your weekend and good luck to all traders next week Upvote 4 Downvote Reply Award Share Mug_of_coffee • 2mo ago We need a table showing how the projected $1,000,000 goal is fluctuating across time. Upvote 3 Downvote Reply Award Share u/Outside-Cup-1622 avatar Outside-Cup-1622 • 2mo ago fair enough, I have been posting this stat for quite a while, maybe I will go back and look at previous ones and put a table/graph together Upvote 3 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Hey Mr. Cup. Thanks for the update. You are not the only one down this week, I am pretty sure the indexes were down 4 out of 5 days this week, definitely down overall on the week. Hoping for a better week to close out June and begin July. Best of luck. Keep grinding on your road to $1.5 Million. Upvote 2 Downvote Reply Award Share u/BeuJay9880 avatar BeuJay9880 • 2mo ago what's the delta-adjusted P&L on the underlying positions? the $502 in premium is the gross income number. the question is how much was given back in losses on the underlying when assignments happened. a lot of weekly premium sellers find the net after underlying delta losses is much closer to zero than the premium captured, especially in weeks where the trade went wrong. Upvote 2 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 1mo ago Hey BeuJay9880. That is a fair question, but I don't get assigned very often. Almost never for covered calls and only if I am actively trying to get assigned on CSPs. The actual P&L depends on the stock’s value relative to that adjusted cost basis, not simply the price movement during the option trade. The $502 is gross premium income for one particular week. To calculate the complete trade result, you would also include realized losses from shares sold below the adjusted basis, or unrealized losses if I still hold them. For this reason, I also provide the unrealized and realized gains in my write-up. I track those separately because premium income and share-price appreciation are different components of portfolio performance. Upvote 2 Downvote Reply Award Share u/MostlyH2O avatar MostlyH2O • 2mo ago Level 300 Karen Profile Badge for the Achievement Top 1% Commenter Top 1% Commenter お前はもう貧乏だ Upvote 2 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Google says that translates to "You're already poor." Neat. Upvote 1 Downvote Reply Award Share MostlyH2O • 2mo ago Level 300 Karen Profile Badge for the Achievement Top 1% Commenter Top 1% Commenter u/CuriousDetective0 avatar CuriousDetective0 • 2mo ago TLDR seems to be the work and effort is not worth it vs passive index holding Upvote 1 Downvote Reply Award Share u/paq12x avatar paq12x • 2mo ago • 2023 up $65,403 (+41.31%) | S&P 500: +26.3% | Nasdaq: +43.4% • 2024 up $64,610 (+29.71%) | S&P 500: +25.0% | Nasdaq: +28.6% • 2025 up $111,496 (+34.52%) | S&P 500: +17.9% | Nasdaq: +20.4% Upvote 2 Downvote Reply Award Share u/CuriousDetective0 avatar CuriousDetective0 • 2mo ago Pre-tax, he beat Nasdaq by about $40.5k over 3 years. But after taxes: Under moderate tax assumptions, maybe only ~$12.7k ahead after tax. Under high-income short-term/options tax treatment, he may actually be ~$8k–$10k behind passive Nasdaq. If he spent real time actively trading, the hourly rate is probably mediocre. Example: Time spent Pre-tax alpha/hr Moderate after-tax alpha/hr 2 hrs/week ~$130/hr ~$41/hr 5 hrs/week ~$52/hr ~$16/hr 10 hrs/week ~$26/hr ~$8/hr Against an equal-weight basket of the actual underlyings, his options strategy looks terrible. The screenshot tickers are: HOOD, QBTS, AMZN, CLSK, UBER, FIG, TDOC, SNAP, RKT, PDD. Using annual total-return data for the other 9 names: Period Equal-weight underlying basket His strategy 2023 +106.1% +41.31% 2024 +102.6% +29.71% 2025 +57.4% +34.52% 2023–2025 cumulative +556.9% +146.6% His stated 3-year P&L was +$241,509, equal to +146.6%, which implies starting capital of about: $241,509 / 1.466 = ~$164,740 On that same starting capital: Strategy 2023–2025 profit His options/account strategy +$241,509 Equal-weight underlying basket ~+$917,441 Difference ~+$675,932 less earned So before tax, he appears to have left roughly $676k on the table versus simply buying the underlyings equally weighted. Upvote 0 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago So many assumptions in this AI generated write up and lot of them are far fetched and/or not true. Leaving $676k on the table is laughable. Upvote 1 Downvote Reply Award Share u/CuriousDetective0 avatar CuriousDetective0 • 2mo ago if he is writing options against those, why couldn't he just buy and hold them? Upvote 0 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Why can’t I do both? Upvote 1 Downvote Reply Award Share u/CuriousDetective0 avatar CuriousDetective0 • 2mo ago You can or just options or just sit in cash, no law against any of those. The question is if your trying to maximize the growth of your wealth overtime, or maximize risk adjusted returns or some other objective? Upvote 0 Downvote Reply Award Share u/Expired_Options avatar Expired_Options OP • 2mo ago Link to the detail behind all options sold this week Upvote 1 Downvote Reply Award Share u/clobbersaurus avatar clobbersaurus • 2mo ago If you’re holding close to 200 positions, why not just get an etf and wheel that? It seems like you are essentially doing qqq but with more steps. Upvote 1 Downvote Reply Award Share [deleted] • 2mo ago Comment removed by moderator Upvote 7 Downvote Reply Share u/Expired_Options avatar Expired_Options OP • 2mo ago Thanks for the comments. Risk mitigation is not sexy, but it works. Upvote 2 Downvote Reply Award Share Community Info Section r/thetagang Joined selling options We are selling options to WSB degenerates using thetagang strategies! 🐌 🐌 🐌 Created Nov 1, 2019 Public 47K Weekly visitors 2.6K Weekly contributions r/thetagang Rules 1 No sales or referrals, advertisment 2 Be civil 3 No social media spam 4 No screenshots without context 5 No self-promotion, subvert advertisement and blog spam 6 No crypto 7 Memes can be deleted if they are not funny 8 Ban bet Sidebar We are selling options to WSB degenerates using thetagang strategies! 🐌 🐌 🐌 Please be civil in your discussions, no WSB language or swearing allowed (automod watches your language on this sub). No spamming of discord links, patreon links, referral codes or paid services allowed. Please don't post direct links to YouTube, no self promotion/shilling. Visit r/thetagang/wiki/index for an introduction to thetagang strategies. 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about 9 hours ago
5 replies Ask a follow up

Account Summary

This is the Reddit user u/Expired_Options, who posts weekly thetagang (option-selling) updates on r/thetagang. Key snapshot of the account:

Metric Value
Portfolio value (shares) $416k across 101 tickers
Open option positions 191 (value $43k)
Total account value $459k
Cash-secured put collateral in use $37,050
Margin / naked options None (cash, shares, or LEAPS-backed only)
Weekly contribution $600 (paused for next month)

This week (Week 26): $502 in premium collected (below his average).

Performance vs. benchmarks:

Period His Account S&P 500 Nasdaq
2023 +41.31% (+$65k) +26.3% +43.4%
2024 +29.71% (+$65k) +25.0% +28.6%
2025 +34.52% (+$111k) +17.9% +20.4%
3-Yr Cumulative (2023–25) +146.6% (+$241.5k) +86.1% +122.0%

He beat the S&P 500 by ~60 pts and the Nasdaq by ~24 pts over three years.

The IRR Question: Option Selling vs. the Long Book

The actual returns cannot be attributed to option selling — and that's the crux of the criticism in the thread. Here's the math:

Option premiums are a small, capped income stream. - Total premium: $163k since 2021 (~$35 per option across 4,000+ sold) - 2025 premium: $68,319; 2026 YTD: $19,732 - Current run rate: ~$759/week ≈ $39.5k/year

Against a ~$459k portfolio, the option premium stream yields roughly ~8–9% per year before accounting for the cost of that premium (underlying losses, cap on upside, rolling losses).

The outsized P&L came from the long positions, not the writes. The account's big gains trace to leveraged/aggressive longs, not theta: - 2025 LEAPS: up $36,440 = +233.74% - AMZN $80 call (2023): +$11,395 = +463% - CRWD $95 call (2023): +$21,830 = +664% - CRWD 1/16/26 LEAPS: bought $8,230 → sold $21,659 = +163%

These are directional long-delta bets (LEAPS), not premium-selling income. The +146.6% three-year return is dominated by long equity/LEAPS beta, not the option-selling strategy.

Why long wins here (the IRR breakdown): - Option selling IRR: on the capital actually deployed to CSPs (~$37k collateral) plus premium, you're earning maybe 8–10% annualized, with capped upside and occasional assignment losses. It's a yield strategy, not a compounding growth engine. - Long/LEAPS IRR: the exponential returns (400–600% on individual positions) are what actually generated the $241k in three years. Selling calls against these caps the upside — the single biggest opportunity cost the thread pointed out.

The counterargument the commenter "CuriousDetective0" made: the underlyings he was writing against (HOOD, QBTS, AMZN, CLSK, UBER, etc.) returned far more as pure buy-and-hold than his total account did. An equal-weight basket of just those tickers returned ~+557% over 2023–25 vs. his +146.6% — implying he left roughly $676k on the table by capping his winners with covered calls.

The OP's rebuttal is essentially that he's not trying to maximize raw return — he's running buy-and-hold with income supplementation, accepting lower upside in exchange for consistent premium and reduced drawdown risk ("risk mitigation is not sexy, but it works").

Bottom line: the +146.6% is not an "option-selling IRR." The option book is a single-digit-yield income layer sitting on top of a long portfolio whose LEAPS and high-beta longs did the heavy lifting. Attribution of the headline return to options would overstate the strategy — the premium income and the long P&L are fundamentally different risk/return streams, which is exactly why the OP tracks them separately.

about 9 hours ago
4 replies Ask a follow up

But how has selling options "reduced" his IRR over buy and hold? Both are mutually exclusive, right?

about 8 hours ago
3 replies Ask a follow up

That's exactly right — and it's the correct way to think about it. They're not mutually exclusive at the account level, but they do conflict on any given position, and that's where the IRR drag comes from.

Let me be precise about the mechanics:

Where they don't conflict

At the portfolio level, you can absolutely do both at once — hold shares long AND write options against different parts of the book. The OP runs 101 tickers and 191 option positions simultaneously. So "buy and hold" and "sell options" coexist fine as separate positions.

Where they do conflict — the covered call on the same shares

The drag happens when the option is written against a position you'd otherwise just hold. Specifically a covered call:

  • Buy-and-hold = you keep 100% of the upside if the stock runs.
  • Covered call = you've agreed to sell at the strike. You collect premium, but you've capped your participation above that strike.

If HOOD or CRWD rips +80% and you sold a call 10% out of the money, you keep the premium + 10% but give away the remaining 70%. You didn't "lose" money — you still made some — but your IRR is lower than if you'd just held the shares. That's the classic, well-documented, mechanical cost of covered-call writing, and it's exactly what the commenter "CuriousDetective0" was pointing at.

The CSP side isn't drag — it's a different allocation

Cash-secured puts don't compare cleanly to "buy and hold" because your alternative isn't holding those shares, it's holding cash or T-bills. A CSP earns more than idle cash, so on that sleeve it's not IRR drag — it's just a modest yield enhancement (with occasional assignment risk). Not a drag vs. buy-and-hold; it's a drag vs. deploying that same cash into the stock.

So the honest framing

Comparison Result
Option income vs. cash/T-bill collateral Slight improvement — CSPs beat idle cash
Covered call vs. holding the same shares IRR drag — upside is capped on winners
The account's total return Driven by longs/LEAPS, not by the options

The reason his +146.6% looks worse than the equal-weight underlying basket (+557%) isn't that he lost money writing options — it's that on his biggest winners, the covered calls capped the exact upside that a pure buy-and-hold would have captured. The premium income he collected was nowhere near enough to offset giving up 400–600% moves on AMZN and CRWD.

So to answer your question directly: they're only mutually exclusive on the specific shares where he sold the call. On those positions, choosing to sell the call literally is choosing to lower the IRR versus holding — the two strategies are competing for the same upside. Across the rest of the portfolio (CSPs on cash, unwritten longs, LEAPS), they coexist without conflict. The "reduction" in his total IRR comes entirely from the covered-call sleeve, because that's the one place the option contract forces him to leave upside on the table.

about 8 hours ago
2 replies Ask a follow up

but he has said his options are almost never assigned

about 8 hours ago
1 reply Ask a follow up

That's a subtle but important distinction — and it actually doesn't change the IRR math at all. "Almost never assigned" is not the same as "I kept my upside."

Assignment isn't where the money is lost

Here's the thing most people miss: assignment isn't required for the covered call to cost you. The investor is not "losing" money when they get assigned — they're losing opportunity the entire time the call is open.

Think about what happens when a covered call is not assigned:

  • The stock stays below the strike → the call expires worthless → the seller keeps premium.
  • But that's a scenario where the stock went nowhere or down. In that world, buy-and-hold gave you nothing either, so there's no IRR gap.

The real cost shows up in the other non-assignment scenario — and this is the crucial one:

The roll

When a stock the OP loves (say CRWD) runs through his strike, he doesn't just sit there and get assigned — he rolls the call up and out. He said it himself: "I rarely close early, prefer rolling when needed."

So the position looks like "I never get assigned," but what actually happens is:

  1. Stock rips +60% through his strike
  2. He rolls the call to a higher strike / later date (often at a debit — paying money to buy back the in-the-money call)
  3. He keeps the shares, never technically "assigned"
  4. But he has now paid real dollars to maintain a position whose upside is still capped at the new (still too low) strike

The money left on the table didn't vanish at assignment — it was extracted during the roll. Rolling a short call that's deep in the money is functionally identical to "being assigned and re-buying the shares," except you pay time value along the way.

So what does "never assigned" actually mean?

It means he's avoiding tax realization and transaction friction — but it does not mean his upside was uncapped. The "almost never assigned" line is true in a bookkeeping sense (shares rarely get called away) while the economic cost of capping winners was paid through rolls and debits, not through assignment events.

The cleanest way to see it

A covered call writer and a buy-and-hold investor both own the same stock. The stock doubles.

Buy-and-hold Covered-call writer
Stock +100% Captures +100% Captures strike to below-strike, keeps premium
"Assigned?" n/a Doesn't matter

Whether the call writer was assigned, rolled, or closed early — in every path, they captured less than +100%. Assignment is just one of several ways the cap gets enforced. Rolling converts "I gave it away at assignment" into "I paid to stay short a losing call," which is the same economic outcome with worse optics.

So the honest summary: his upside was capped on his winners regardless of assignment frequency. "Almost never assigned" tells you how he mechanically manages the in-the-money calls (rolling instead of letting shares go) — it does not tell you that he kept his buy-and-hold returns. He didn't. The +463% AMZN and +664% CRWD returns he quotes are from the LEAPS he held long, not from the shares he was writing calls against. Those are two totally different positions.

about 8 hours ago