You are the put-selling king on SDN. I don't have as much put-selling experience compared to you and I learned a lot from your posts. These days, I don't give much feedback here but I want to give back some value to you instead of just taking.
I'm not married to a particular investing strategy. I just want something that works the best. I believe we graduated residency around the same time and I have grown my taxable account from 0 to a high amount that I can retire now if I wanted to. Maybe my insight may provide a new perspective.
I'm surprised you're no longer indexing to the stock market. I guess you're deploying the bulk of available capital into options. I thought about your strategy and although you outperformed S&P 500, there are several headwinds imbedded in put-selling that impair growth of net worth:
Taxes: This is the biggest headwind. Assuming you're in the max tax bracket making physician salary with a max state income tax of 5%, taxes would be 37% (federal rate) + 3.8% (NIIT) + 5% (state rate) = 45.8%. Let's around it down to 45%. Your after-tax return is 2% * 12 months * (1 - 45%) = 13.2%. It isn't much better than buying S&P 500 as the indexer is letting compounding work without paying taxes (excluding taxes from dividends).
Commissions: These small expenses add up the more you trade. Wasn't there an option trader on this forum that accumulated 6-figures in fees? What a drag to net worth.
Time: It seems you gravitate towards companies and emerging markets. Researching about companies and countries take time. Even though you can roll down losing options, you still want the underlying asset to be good. If you keep rolling down Enron, you'll lose a lot of money due to leverage. After taking positions in various companies and countries, you will spend time rolling over contracts. You will also have to figure how to position size to reduce risk of ruin. You will have to check on your various positions to make sure they're not going to blow up. You will have to figure how to enter and exit positions especially if liquidity is subpar. Preparing taxes would also eat up a lot of time due to the trading. Maybe this is your pastime and you enjoy it but it is still substantial cost.
Liquidity: Options on some companies are less liquid and thus less scalable compared to buy and hold.
At the end of the day, you're employing leverage to juice returns. There are multiple ways to apply leverage. Your method is inefficient through the headwinds I listed above.
If you are married to the put-selling strategy, get into futures. Section 1256 tax treatment is much better than paying 45% taxes per year. It also makes filing taxes much easier, saving time. You don't have to do as much research as you don't have to research individual companies. Liquidity is also better. Here is a very good site about put-selling regarding futures:
The strategy in a nutshell I’ve written about this strategy in previous posts, most recently in Part 10 and Part 11. But briefly, here is what I’m doing: Why does this work? Implied Volatility (normally) exceeds Realized Volatility. Of course, the central limit theorem is useful only if the...
earlyretirementnow.com
With the way the financial system is set up, the optimal solution is to buy and hold. Put selling and buy & hold are directionally similar anyways. The richest people in the US are not traders but holders of companies. Steve Ballmer is richer than Bill Gates because the former diamond handed a great company while the latter is more concerned about population reduction. You can easily beat index by employing leverage in buy and hold method as well.
From 07/01/06 - 07/18/24, $10k initial investment with $2.5k added each quarter in SPY would have resulted in $726k. The same amount in SSO would have resulted in $1,568k. Buy and hold. Minimal taxes. Minimal commission. Minimal time. Decent liquidity.
I personally am not invested in any of the investment strategies I talked about here. And I'm not saying you should change. But keep an open mind.
Thank you for your thoughts.
Believe it or not, these are the exact same things I've thought long and hard about. And every now and then I revisit these topics again and again.
I'm going to try to explain how I've come to the conclusion to do what I'm currently doing after contemplating over the topics you mentioned. I'm going to tackle each topic one by one.
TAXES:
Yes. I agree. Short term capital gains is painful. But you're actually not doing a apples to apples comparison. The long term buy and hold investor also EVENTUALLY pays taxes. A person like me whose worth 2 million at age 35, likely will have a considerably large net worth when I'm in my 60s. So my assumption is I'll likely remain a high income tax bracket person - hence likely a 20% capital gains tax rate. NIIT tax, state income tax you regardless pay on long term capital gains. But, I'd still pay 20% capital gains tax as a buy and hold investor (based on current laws and brackets - may change in the future who knows). So the difference between my short term capital gains tax and long term capital gains tax rate in fact is only 17%. Lets say increased risk and leverage lets me get ~ 20% annual return vs SPY 11% average annual return. The 20% return after accounting for an extra 17% tax (37% short term capital gains rate vs 20% long term capital gains rate) is essentially 16.6 vs 11. The remaining taxes paid are the same for each. So you can't compare a post tax return in one scenario vs a pre-tax return in the other scenario. While taxes definitely eat up a traders returns, but even long term capital gains taxes are substantial. In fact several congressmen are attempting to change the long term capital gains tax rate to the income tax rate for wealthy individuals as well - So I don't feel super confident about the future rate being 20% 35-40 years later.
If you actually do the math, if something is taxed every year vs something that is taxed 20 years later - as long as the tax rate is the same, both investments end up the same. So, $100 invested every month growing at 8% for 20 years (with 20% paid to the tax man) is the same as $100 invested every month growing at 10% for 20 years and then paying 20% on the eventual capital. Both are identical. So - the only difference is an extra 17% and as long as I have a 117% return of the total return of my benchmark (which is actually not SPY - my personal benchmark is a target date fund), then my return is superior despite added taxes. Unfortunately Etrade only shows the last 3 years which is now excluding my first year of options trading (which was actually a block buster year), but even then I'm far exceeding the 117% goal of beating my benchmark (2055 target date fund by vanguard). My benchmark is a target date fund because I'd be invested in a 3 fund portfolio if I wasn't doing options. I will not be 100% VTI/SPY. I believe anyone who is 100% VTI/SPY is ignoring current US valuations and has recency bias. My return has been 4x my personal benchmark in 3 years even after accounting for the extra 17%. So the extra 17% doesn't bother me.
Lets talk about Futures. Granted I only have a vague understanding of futures. But my understanding is that futures allows for 100x leverage. Selling naked puts whereas allows for 10x leverage on things like IWM, SPY, RUT, SPX, QQQ etc. I don't even come close to fully utilizing naked puts leverage let alone ever consider going 100x leverage. The other thing I really really don't like is the fact that futures markets are barely ever closed. I can't imagine the anxiety I'd feel if the market was open 18 hours a day. My sleep quality would worsen, I'd be watching the markets a lot more, especially when markets would be going down, I'd have a lot more time to react in a detrimental manner. So I just don't do it. Yes, you get 1256 tax treatment and get 60% of your profits treated as long term capital gains - BUT I dont need futures for that. I can trade RUT, SPX, XSP options and have the EXACT SAME 1256 tax treatment and have 60% of my short term capital gains treated as long term gains. In fact, my first entire year of trading options was ONLY trading RUT. That's it.
But after A LOT of thinking and several times re-visiting the topic, I moved away from RUT to higher volatility things like EWZ, ARKK, TAN, KBE, KRE, JETS, FXI, and some hand picked beaten down single stocks with fortress balance sheets, earnings, and/or assets (MPW, LYFT, PYPL, META, PINS, PAYC, SQ). And here's the math behind this decision - Like I said there's a 17% tax difference between short term capital gains vs long term capital gains. If I did Futures OR SPX/RUT/XSP options, that 17% difference is now 10.2% since 60% of capital gains will get taxed long term while the remaining is still taxed at short term. So, as long as I can get 110.2% or higher return than trading SPX/RUT then I'm still ahead of doing 1256 contracts.
So - I'll show you what I need to get a 2% monthly return for SPX vs something more volatile.
So - I'd have to sell 13 August 19th contracts for a strike of $5100 (7.6% below todays price) to get $14500 of premium in 31 days. The leverage on this position is RIDICULOUS. 10X. Highly highly highly leveraged. 13 contracts on SPX with strike of 5100 has a theoretic maximum loss of 510000 x 13 = 6.6M. The above trade will use 660k of buying power. SPY has had weeks where it has dropped 5+ percent in a week. It has in fact had a few 10% drop days as well - 1 10% down week will completely wipe me out. Margin maintenance call. 6 figure losses. Massive wipe out from the leverage.
Lets compare that to MPW. A stock backed by real estate values that has time and time again showed that the portfolio assets are valuable when sold.
To get a 2% return from MPW, I'd have to sell 1300 contracts for $3.5 strike (todays price $4.74 - so 26% below todays price) with a expiration 28 days from now. This trade gets me 14300 premium, uses very minimal leverage, uses a buying power of $310k (half the buying power of the above trade), and the maximum theoretical loss is 441k. So considerably lower leverage. Plus being 26% below todays price means that if it dropped 10-15% tomorrow, Its still a salvageable trade and I'm maybe losing 20K-30k on a negative 10% day rather than 20% of my networth if SPX lost 10% in a week.
Yes there is single stock risk, but do it with 5-10 companies and a bunch of ETFs and you mitigate that risk. With significantly better return per unit buying power used, i've come to the conclusion of just trading the things I trade and paying the extra tax because I believe I will get a better return, while using less leverage through trading more volatile things. To me less leverage is less risk even if its trading something more volatile.
And I say the above after literally doing 1 full year of RUT only and enjoying the 1256 tax law.
Commissions:
I only pay 15 cents a contract vs 99% of brokerages charging 65 cents a trade. My trading costs aren't actually bad. It's a negotiated rate with etrade.
Also, I signed up for an account with public.com as a backup brokerage. They don't have full naked puts yet, but they will roughly pay me 18 cents per contract instead of me paying them per contract. They will essentially share 50% of their order flow revenue. Right now they just have cash covered positions. But yeah...Not only do they have $0 comissions, but they share 50% of their order flow revenue which is 18 cents a contract on average.
Time:
Yeah it takes time. Not for everyone. I enjoy it though. I like dabbling in things. I've started 3-4 failed businesses, I've set up a couple of ecommerce stores, ive tried drop shipping, ive imported stuff from china in bulk and sold on ebay, i've attempted etsy stores - THIS AND SYNDICATION REAL ESTATE HAS BEEN MY ONLY SIDE GIG/HOBBY THAT HAS ACTUALLY MADE MEANINGFUL MONEY. I've spent so much time on other ventures and failed, this is the only thing that has reliably been successful. If I'm not doing this, I'll probably be looking through bizbuysell.com or flippa.com to buy a business or a website. I enjoy this kind of mental stimulation. Instead of me wasting time on a failing venture, at least my hobby makes money that I genuinely enjoy. But if I'm not doing this, I'll be dabbling in something else which is historically less likely to be successful based on how I've done in the past with business ventures.
Liquidity:
I don't trade things with low liquidity. The bid ask gap of low liquidity positions have been very painful in the past. If I do trade something with low liquidity, its almost always a very small meaningless position. The larger positions (>100+ contracts) are always going to be highly liquid things.
Buy and hold:
Yeah...I know. If I pick a NVDA or AAPL at the right stage and early enough then I would never ever come close to those returns. But I think I will beat the return of a buy and hold investor who is indexed in 60% US stocks and 40% International stocks over a long term. That's what I would be invested in if I wasn't doing options. So...that's the benchmark I compare myself with.
Hopefully that explains what I do and why I do it. The tax question comes up again and again in my head. It's a very valid question. I think once I have 3-4M in assets, a large part of my portfolio will start going back to indexing and some income funds like JEPI/JEPQ even. My appetite for risk is definitely decreasing as I'm worth more.