SteadyOptions is an options trading forum where you can find solutions from top options traders. Join Us!

We’ve all been there… researching options strategies and unable to find the answers we’re looking for. SteadyOptions has your solution.

Is Your Risk Worth the Reward?


One of our members posted a link to an excellent post from Mark Wolfinger. Mark responded to a question from one of his readers: "For the past 2 years, I've been selling naked options (mainly puts, a few calls) to generate monthly income. My position returns just over 1% per month on average on the total account value".

After 7 years of bull market, many traders forgot the meaning of risk. They think they can just buy call options and/or sell puts and make outrageous digits returns every year. I suggest that everyone reads Mark's post, it's an excellent read with a lot of wisdom.

 

Is selling naked puts a good strategy?

 

Mark's response is fairly long - here are the most important points:

 

"This is not a conservative strategy. Not even close. It is a high probability play, with many profitable months. I cannot imagine a strategy in which I earn a profit month after month for several years. Yet this strategy could provide those results. The question is: how much is at risk?

 

No matter what anyone tells you about risk, you just know that either nothing terrible is going to happen, or if it does happen that you will react in plenty of time. Let me assure you that in Oct 1987, puts were not buyable at any price that you would have been willing to pay.

 

You did live through the winter of 2008, but if you have truly been doing this for 24 months, you began at the right time. You missed out on the excitement of Sep and Oct of that year.

 

Have you considered what would have happened had you begun in August 2008, instead of 3 or 4 months later? If you have access to TradeStation (or if your broker offers back-testing – I believe thinkorswim does), go back to August expiration, choose options to sell for the Sep and Oct expirations and then follow the trades." 

 

I am NOT telling you what to do, but you have not been through what I have.  You have not seen how quickly money can vanish from your account.

 

What is your risk/reward?

 

We are familiar with some services that advocate selling naked puts on 25-50% of their portfolio. In our opinion, this is a financial suicide. This strategy obviously performed very well in the last few years. Interestingly enough, the track record of those services usually doesn't go beyond August 2011, not to mention October 2008. One of them has data going back to 2009 (again, not 2008 ), but August 2011 is missing. Coincidence?

 

To give a fair margin of safety, the strikes are usually far enough from the money to give you around 2-3% potential return on margin. Well, 2-3% per month sounds very good, but what about the risks? In a month like August 2011 (not to mention October 2008) the loss could easily reach 30-50%. In October 2008, it could wipe out your account. Is 2-3% per month worth the risk?

 

The latest case of Karen the Supertrader who implemented similar strategy of selling naked options provides a good example of the risks.

 

How our strategies handle risk?

 

Let's take a look at our strategies and see how they handle risk.

 

SteadyOptions

 

At SteadyOptions, we trade a mix of non-directional strategies. They might include Iron Condors, Calendars, bufferflies, earnings straddles etc.. The idea behind earnings straddles is buying a straddle 5-10 days before earnings and hold it till earnings. The strategy is based on my Seeking Alpha articles Exploiting Earnings Associated Rising Volatility and How To Rent Your Options For Free. We expect the IV increase to offset the negative theta and/or book some gamma gains in case the stock moves.

 

In periods of low IV, the earnings trades are expected to produce 3-5% average return, and theta positive trades like ICs and calendars are expected to provide us most of the gains. However, the earnings trades serve as a nice hedge to the theta positive trades in case of a quick and sudden move. To see how they performed when the markets become volatile, take a look at August 2011 returns here or July 2012 returns here. Those trades are basically our black swan event insurance, and we get it for free - in fact, most of the time we even make some money on it.

 

Anchor Trades

 

An Anchor trade's goal is to prevent loss of capital while still generating a positive net return in all market conditions. This strategy began with the premise that it must be possible to virtually fully hedge against market losses, without sacrificing all upside potential. It is expected to lag the S&P 500 in a strong bull market like 2013. In 2013 the lag was larger than expected due to poor selection of stocks. Going with ETFs instead of stocks would lag the S&P only by few percentage points, which means that the hedge almost paid for itself.

 

The impact of not experiencing losses in down market years, while only slightly lagging (if lagging at all) in positive and neutral years, is astronomical over any extended period of time. Again, it is very easy to become complacent in the current bull market - but the market will correct at some point. It's not a matter of if but when. And when it does, you will be thankful that you are hedged. As an example, the Anchor return in May 2012 was +4.6% while S&P plunged -6.2%. In 2008 when S&P was down 38.4%, the Anchor was up 27.9%.

 

Steady Condors

 

Steady Condors is a market neutral, income generating, manage by the Greeks strategy. The trades are primarily risk managed variations of iron condors. The big difference (in addition to how the adjustments are made)between the Steady Condor main trade (MIC) and the "traditional" Iron Condor trades is the fact that MIC uses a put debit spread plus some far OTM puts for black swan event protection. This protection is placed when the trade is initiated - in other words, we buy protection when we want to, not when we need to. The result is that in case of market crash or black swan event, the trade actually becomes vega positive and those hedges provide an excellent protection.

 

We conducted a case study for the August 2011 trade (available on members forums). It's a fascinating read. During the life of the trade, RUT was down over 11% - yet the trade was closed at profit target of 5% on Aug. 4. Interestingly enough, on Aug. 8 RUT closed down 64 points at 650. If you wouldn't have taken the trade off on the 4th the trade would actually have been up 67% at the end of the day on the 8th. This is the power of protection, combined with exploding Implied Volatility.

 

Conclusion

 

When comparing different strategies, don’t forget to consider both historical performance AND historical drawdowns in both up and down markets. Mark asks the following question: "How much will you lose if the market opens 20% lower one day, RUT IV (RVX) moves to 90 or 100, and the option markets get very wide?This is your stress test - does your portfolio pass it? 

 

Want to see how we handle risk?

 

Start your free trial

Edited by SteadyOptions

What Is SteadyOptions?

12 Years CAGR of 114.5%

Full Trading Plan

Complete Portfolio Approach

Real-time trade sharing: entry, exit, and adjustments

Diversified Options Strategies

Exclusive Community Forum

Steady And Consistent Gains

High Quality Education

Risk Management, Portfolio Size

Performance based on real fills

Subscribe to SteadyOptions now and experience the full power of options trading!
Subscribe

Non-directional Options Strategies

10-15 trade Ideas Per Month

Targets 5-7% Monthly Net Return

Visit our Education Center

Recent Articles

Articles

  • Optimizing Portfolio Growth: Managing Capital and Liabilities in Modern Tax Planning

    Growing your investment portfolio involves more than just picking winners. While strong returns are the goal, many investors overlook a critical factor that significantly impacts their net worth: tax planning. Managing your capital and liabilities with taxes in mind isn't just about saving money in April. It's a year-round strategy that can accelerate your portfolio's growth and help you keep more of what you earn.

    By Kim,

    • 0 comments
    • 472 views
  • Expanded Trading Hours for Select Equity Options

    The Cboe Options Exchange will start offering expanded trading hours for select high-liquidity single-stock equity options. The schedule features a morning Global Trading Hours (GTH) session from 7:30 a.m. to 9:25 a.m. ET and an afternoon Curb session from 4:00 p.m. to 4:15 p.m.

    By Kim,

    • 0 comments
    • 611 views
  • How LEAPS Differ From Short-Term Options

    LEAPS stands for Long-Term Equity Anticipation Security. Which is just a long-dated option, typically referring to those with expirations more than a year out. There’s no technical difference between LEAPS and shorter-term options other than the expiration date. They’re traded on the same exchanges and have the same rules surrounding margin and whatnot.

    By Pat Crawley,

    • 0 comments
    • 31186 views
  • Why Not to Hold Strangles Through Earnings

    In my previous article, I described a strategy of buying a long strangle a few days before earnings and selling them just before earnings. In this article, I will show why it might be not a good idea to keep those strangles through earnings.

    By Kim,

    • 0 comments
    • 6089 views
  • Pre-Earnings Entry Price: What 31,000 Cycles Say

    Every card in the scanner carries a block called How expensive is this entry? It compares what you would pay today against what the same setup cost on the same ticker at the same point in past cycles. I built that block in August. It reads well. But a reading that looks sensible and a reading that predicts something are different things, and until last week I had only the first.

     

    By Romuald,

    • 3 comments
    • 652 views
  • Expensive Compared to What?

    A trader looks at a pre-earnings straddle and asks whether it is expensive. It is the right instinct and the wrong question, because the word carries no meaning on its own. Expensive against what? A $12 straddle on a $200 stock is not expensive or cheap. It is $12.

    By Romuald,

    • 0 comments
    • 540 views
  • Beyond Strategies: What Options Traders Should Know

    Options education almost always begins with structures. Traders learn vertical spreads, calendars, butterflies, condors, covered calls and straddles, study the expiration diagrams, work out maximum profit and loss, and build a sense of the conditions each structure is supposed to suit. That foundation is necessary and there is no way around it.

    By Kim,

    • 0 comments
    • 1071 views
  • SPX vs SPY Options: Which One Should You Trade? (2026 Guide)

    Both SPX and SPY options give you exposure to the S&P 500. They track the same 500 stocks, move nearly tick-for-tick, and offer the same core strategies — credit spreads, iron condors, butterflies, and 0DTE trades. Yet the two products settle differently, are taxed differently, and carry very different assignment risks.

    By krisbee,

    • 0 comments
    • 5157 views
  • Strike Price Effects Or Pinning Revisted

    Loyal readers of this blog will recall my post from 2019 “Pinning Down the ‘Option Pinning’”. If you have not heard of pinning have a look at that article as – spoiler – everything in it as well as Jeff Augen’s observations in his books which are referenced is still valid.

    By TrustyJules,

    • 0 comments
    • 2332 views
  • Could This Strategy Be The Holy Grail Of Investing?

    This is a reprint of my Seeking Alpha article from 2013. If you have SA subscription, you can read the full article including hundreds of comments here. For the record, the strategy implementation has changed since then, but the principle remains the same. You can read more here

    By Kim,

    • 6 comments
    • 5747 views

  • Upvote 1
  Report Article


We want to hear from you!


There are no comments to display.



Join the conversation

You can post now and register later. If you have an account, sign in now to post with your account.
Note: Your post will require moderator approval before it will be visible.

Guest
Add a comment...

×   Pasted as rich text.   Paste as plain text instead

  Only 75 emoji are allowed.

×   Your link has been automatically embedded.   Display as a link instead

×   Your previous content has been restored.   Clear editor

×   You cannot paste images directly. Upload or insert images from URL.

Loading...