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My Latest Cover Letter (Part 6)

Through a series of blog posts (Part 1, Part 2, Part 3, and Part 4), I feel I have done a pretty good job of describing what I seek, what I have done, and what I offer to a prospective financial firm. Organizing and putting all this into words has been a herculean effort for me. One thing that remains quite understated is the content presented in this blog.

In Part 5, I started to bring my writing to the fore with a sampling of blog posts.

To say this blog is extensive would be a vast understatement:

With the exception of time, this blog really is my job interview. Its entirety makes me the most transparent of candidates you will ever see with regard to motivation and any ulterior motives I could possibly have.

The current mini-series is my best attempt thus far to encapsulate everything I am in the domain of finance: trader, backtester, analyst, commentator, writer, defender, and scientist (in any order you well please).

Trader Networking, Trading Success? (Part 2)

Part 1 discussed frustration over spotty e-mails when trying to network with other traders. Should consistent, prompt e-mail replies be a prerequisite for trading group candidates, and does effective networking bode well for trader success?

I honestly don’t know how often people check e-mail these days so I did a quick internet search. Reliable statistics are hard to find, but here are some potential answers:

How often e-mail should be checked is also unclear. I have seen so-called “experts” recommend:

Any of these would be satisfactory for my purposes. I don’t even need a response the same day. Getting a response within 2-3 days is more than sufficient for the purposes of planning a group meeting a couple weeks out in time.

These cursory findings also confirm my frustration over spotty replies. If most people check e-mail so often then why do my leads seem so disconnected? The caveats listed in Part 1 still apply, of course: accidental oversight could be involved.

Switching gears a bit, I think it safe to say that not too many people have substantial success trading the markets. As discussed in the sixth paragraph here, I have had very little success finding other full-time traders. 90% is the oft-quoted failure rate, which I wrote about in this blog mini-series. I also wrote about it here many years ago, and here I discussed one actual study that suggests the failure rate to be even higher.

I had a challenging time organizing this group, which managed to survive for a couple years. We had decent participation across 7-10 members. 3-4 members presented at least the occasional trade while two of us presented frequently. Only one of us (me) was trading full-time.

I have seen many trading meetups struggle to find consistent attendance and subsequently shut down. The AA District Library once refused to advertise an investing program because historically, they found such content to be in low demand.

I wonder about a possible relationship between consistent group attendance and trader success. Might retail traders benefit by coming together to discuss and develop strategy? Might organized trading teams offer accountability benefits? In my humble opinion, AB-SO-LUTE-LY! For various psychological reasons, getting ahead in trading by working alone is very, very difficult.

I would certainly guess those who work together in groups have more success than those who trade on their own. I have discussed benefits of trading groups in the second-to-last paragraph here, the second paragraph here, and here.

One person who responded to my networking e-mail said:

     > I’ve been trading for years, more purchase of securities. But started
     > with options about 1 year ago, it’s not easy. Everything I seem to select
     > goes the opposite direction 😫… I try to do it every day. lol, well
     > at least look at it to select something.

Do I think she could be taught to approach this in a more disciplined, systematic way? Yes! Does she have the necessary commitment to learn, practice, and develop? I would have to know her better to answer that.

If you believe that trading groups are correlated with greater success and if trader networking can lead to the creation of trading groups, then trader networking can definitely be correlated with trading success.

Trader Networking, Trading Success? (Part 1)

This will be another (e.g. see here, here, and here) post about trader networking. Submitted for your approval is the question of whether effective networking has anything to do with trader success?

To understand where this comes from, I am new to the Sunshine State and trying to network with other traders. My hope is to meet people and possibly further my trading at the very same time. My preference would be to meet as a group.

Our old friend Meetup.com is my primary source for potential leads. I have joined a few trading- and investment-related meetups in the area. Only one has actually had an [online] event thus far. I have messaged a number of people through the site in an effort to reach out.

My opening salvo is rather benign:

      > Hi! I am new to the area and looking to network with other traders.
      > Let me know if you would like to chat. Thanks!

I think my bio (introduction) is relatively benign as well:

      > Full-time, independent option trader looking to network with other
      > like-minded individuals. I’m always interested in the possibility
      > for collaborative projects.

I’m a friendly guy. I’m pretty easy going. I’m a good listener. I’m interested in your story and what you have to say. Hopefully I check any ego at the door. Let’s talk, shall we? Sure, why not!*

I approach this in an organized fashion so as not to offend anyone or inadvertently cross boundaries. This means keeping track with a networking spreadsheet (at the risk of becoming a “uses-a-spreadsheet-for-everything” person). If anyone tells me “no,” then I certainly do not want to bother them again. If anyone doesn’t answer then it could be a fake account, a spammer, or someone not real. The notification message could have gone to their spam box, though, or it could just be an oversight in which case a follow-up might be advised. It could also be someone not very consistent with e-mails.

E-mail inconsistency is what really makes me wonder. I used to hear people say things like “I’m not very good with e-mail.” Is that still a thing? As the years go by, smartphone technology has progressed where more and more apps have been created for this, that, and everything else. How many people are away from their phones for lengthy periods of time? I have often considered myself lagging behind on technology but even I am connected most of the time now. I rarely go more than several hours between e-mail checks.

Spotty e-mail response is my biggest problem in these initial networking stages and I debate whether this should be a deal-breaker. I’ve said traders are a fickle lot (e.g. see here, here, and here). I will lose interest if I schedule some small group meetings only to see them canceled because a few people call out sick or [even worse] pull a “no call, no show.”

It’s probably a case of “no risk, no reward,” though, and “you don’t know if you never try.” I’m trying!

I will continue next time.

*—This is the image I’m trying to convey along with the desired outcome.

My Latest Cover Letter (Part 5)

I maintain this blog to hold me accountable for work and related projects. It shows good insight into my activities, my trading, and my related thoughts/education over the years. If presented effectively, I think this blog could be my entire job interview.

At the risk of being repetitive, I am going to include an e-mail sent to the CFA institute in March 2021. Earlier this year, I contemplated taking CFA Level 1. I looked at the CFAI website and scrutinized the criteria to earn the charter. One thing I questioned was my work experience since I technically have not worked in the financial industry proper:

—————————————————————

…the reason for my contact is because I know enrolling to prepare and sit for the CFA exams will take a great deal of time, effort, and money. I hope I can pass them all and should that be the case, I would be heartbroken to be denied a charter because the Institute wouldn’t approve my self-employed work experience.

My résumé outlines much of what I have done as a full-time trader since 2008. I have spent many hours watching trading videos online, attending investment and trading Meetups, attending seminars and webinars, participating in online trader forums, and communicating/collaborating with other retail traders. I have also spent many hours backtesting trading strategies and analyzing performance. I have read and taken copious notes on tens of books related to trading and quantitative finance. I log time in a spreadsheet, which totals over 21,000 hours to date. Although I trade only for myself, I have treated this as a full-time job from the very beginning. This is my passion and my business.

In 2009, I created a trading entity (LLC). My tax returns have listed me as “Trader in Securities” for at least the last 10 years.

I led an options trading group from 2013-2016. We had a handful of regular members. It’s very hard to find other full-time retail traders like myself, which is one reason I have given thought to pursuing formal employment in the industry.

I blog about my work and finance-related topics regularly at http://www.optionfanatic.com. What follows is a sampling of over 1,000 total posts I have written since May 2010:

The blog is not monetized and from what I can tell, it garners little traffic. I maintain the blog to keep me on track with trading and with related thoughts and projects. It’s a way of holding myself accountable for the work that I do.

Thank you for looking into this! Let me know if I can provide anything else.

—————————————————————

I will conclude next time.

Naked Call Backtest (Part 5)

As mentioned previously, increasing position size makes this profitable: not anything about the naked call strategy itself.

Do any research on Martingale betting systems and you will see they are not recommended. I wrote about this here. The smaller I start as a percentage of the total bankroll, the lower probability I will run into a string of consecutive trades long enough to go bust. Make no mistake, though: it most definitely can happen [and since Mr. Market “can remain irrational longer than you can remain solvent,” it probably will].

What are some ways a strategy like this may be viably implemented?

One way is to position size as a fraction of the entire account. I did calculations in Part 4 based on $240K risk. If this is 10% (for example) of my total account, then I can rest easy because at absolute, never-before-seen worst, I lose 10%.

Another way to trade this responsibly might be to overlay on top of a long strategy that offsets naked call (or vertical spread) losses when the market rallies. Keep in mind that calls are NTM compared to equal-delta puts due to vertical skew, which means portfolio margin requirements can grow faster. Trading fewer call than put contracts as net short premium is one way this can make sense; just remember the number of call contracts may increase at least 16-fold.

Implementation of stop-losses is another avenue for the naked call (or vertical spread) strategy. By improving the avg win:avg loss ratio, I can mitigate position size increases. Stops increase number of losses, though, because a trade cannot recover once it has been closed. Backtesting is needed to better understand whether one factor is clearly more likely to prevail.

Finally, intraday backtesting (discussed in this blog mini-series) remains undiscovered country. Mine is a once-daily backtest,* which allows up to 24 hours for things to go from bad to worse. The worst backtesting loss is on 4/6/20 when a call sold for $1.35 is closed for $45.30. As mentioned in the second-to-last paragraph here, I think ITM short puts are best rolled before they go OTM. The mirror image dictates rolling short calls before they go ITM. Win percentage would decrease, but magnitude of loss would be lower. Again, backtesting is needed to better understand whether one factor is clearly more likely to prevail.

As discussed in the last paragraph here, by rolling rather than taking on some unknown legging risk and leaving short options to expire worthless, the current backtest errs on the side of conservatism. Rolling involves buying out remaining premium and realizing excessive slippage upon exit, which would both be expected to dampen performance slightly.

* — I used market prices at 3:50 PM until Dec 2020 and at 3:45 PM daily thereafter.
       This was due only to inadvertent oversight. The catch-22 is to use data as
       close to expiration (4:15 PM ET) while not suffering widened, distorted bid/ask
       spreads often seen after normal market close (discussed in fifth paragraph here).

Naked Call Backtest (Part 4)

Do you take it or leave it? I say the latter. With a couple changes, though, this trading strategy becomes a bit more enticing.

All of this exempts previously-addressed caveats having to do with dynamic strategy guidelines:

  1. Use OptionNet Explorer (ONE) between 3/23/2020 – 7/1/2021.
  2. Sell 10 naked calls in nearest weekly expiration (1 – 4 DTE) for just over $1.00/contract.
  3. Assess transaction fee of $16/contract for slippage and commission.
  4. Monitor market and/or trade once daily at 3:50 PM ET (3:45 PM ET starting Dec 2020).
  5. If ITM, roll to following weekly expiration as far OTM as possible for credit; increase size with discretion.
  6. Otherwise, rinse and repeat on expiration day with 10 new contracts.

With regard to (2), the target premium is $1.00 but I aim for ~$1.30 – $1.40 to offset transaction fees. If I have to pay material premium to close (e.g. more than $0.05) then I add to target premium in order to net target premium. For example, if I BTC for $0.75, then I will look to sell the next call for ~$2.00.

With regard to (5), I aim to increase size and leave sufficient cushion in case the market continues upward. What constitutes “sufficient” is what makes this discretionary.

Here are the results:

Naked put (ROD2) results (11-2-21)

Shocking improvement from Part 1! This equity curve climbs consistently with eight large, brief pullbacks. The average loss is about seven times the average win. While not so great, the strategy wins 93% of the time.

The maximum drawdown (MDD) occurs here:

Naked put (ROD2) 4-3-21 to 4-13-21 results (11-2-21)

Albeit confusing, SPX price increases 10% from April 3 – 14, 2020. I could have rolled the initial 10 to 40 instead of 20, but I would still have lost a second time and had to roll to 80 contracts. A market pullback allows for a profitable exit.

Is this a viable strategy for live-trading? Follow the logic:

Given this may supplement a long portfolio, I am somewhat encouraged especially in comparison to the monthly approach.

Unfortunately, increasing position size is what makes this strategy work—not the strategy itself. When I apply constant position size throughout and add the additional cost to spread off risk, I get a profit factor of 1.03: dismal at best.

But, but… I’ll take any bonus return since I’m trading this sufficiently small to support a 16x increase in position size!

Is it conceivable that we could have more than four consecutive big up periods maybe lasting two weeks or more?

Could I go bust as a result?

Yes. Absolutely.

I will continue next time.

* — This is a very conservative estimate; with the option being $0.10, slippage would actually be half that.

Naked Call Backtest (Part 3)

Before proceeding with more backtesting data, I want to clarify some previous points and make a casual observation.

Position sizing based on max drawdown (DD) says “the largest DD I ever saw in backtesting was X. If I never want more than a Y% DD on my account, then minimum account size is X / (Y / 100).” As an additional margin of safety, suppose the largest future DD will exceed max DD by a factor of Z. The minimum account size becomes (X * Z) / (Y / 100).

Given the $407K MDD (one contract initial size), preference not to see my account down more than 20%, and anticipation of future max DD 2x worse than that seen in the past, minimum account size should be ($407K * 2) / (20 / 100) = $4.07M.

Even if I can position size this way based on max DD, portfolio margin requirements (PMR) could still be a limitation. As account equity decreases and margin limits approach, I may not be able to continue holding the position. Recall from Part 1 that depending on index value, PMR is $1.7M – $3.3M when starting with one contract. A $4.09M account suffering a 40% DD becomes $2.45M, which can no longer support a $3.3M PMR.

DD and position size both determine whether an account can support a position. Position size is proportional to PMR. DD affects buying power. A margin call will be issued by the brokerage as buying power approaches [and certainly slips below] PMR forcing clients to deposit additional funds or to close positions (else the brokerage will do so for them).

Vertical spreads cap PMR, which is still proportional to index price. We probably need to determine the larger of max PM or max DD (along with associated fudge factors discussed in second paragraph) and base position sizing off that.

Large variance across IV and index price level demands more dynamic guidelines for normalization. This backtest implements a static premium in the face of wide-ranging underlying price and volatility. Implementing a static delta, instead, would allow for a normalized strategy that proportionally self-adjusts over time.* If I were doing spreads, then width could be better defined [dynamically] in terms of index price since a static 200 points is 10% of 2000 and only 5% of 4000.

This can all be confusing, which is why I wrote an entire mini-series on it.

As a final note, this backtest closes all short options no later than 3:50 PM on expiration Thursday. In live trading, the short option can often be left to expire thereby saving premium and transaction fee. A cursory review of current results reveals a difference up to $15K: sizeable, to be sure, but amounting to little more than a rounding error all things considered.

*—Added to my to-do list.

Naked Call Backtest (Part 2)

I left off analyzing naked calls with respect to portfolio margin (PM) and maximum drawdown (MDD).

The strategy could be implemented based on maximum drawdown (MDD), but margin is another clear limitation. Even one contract could require up to $3.3M in PM for ~$108K profit. This paltry 0.34% total return gets even smaller as the index continues to climb. Not worth it!

One thing I could do to decrease PM would be to sell the vertical spread instead of naked call. Going 200 points wide would risk up to $20K/contract. Ten contracts would be up to $200K in PM, but I certainly could not increase 64-fold from there.

The spread concept brings with it some other interesting revelations. The backtest starts in high IV:

Short call vertical high IV low index value (10-25-21)

Observations:

The backtest ends in low IV:

Short call vertical low IV high index value (10-25-21)

Observations:

High IV is lower risk in terms of delta, but generates less credit because the long option is relatively expensive compared to the short. Low IV collects more credit but does so at a relatively higher delta, which is more risky.*

These examples illustrate two major differences: IV and index price. With regard to the latter, selling a fixed dollar amount is relatively NTM (higher delta) for index at lower value compared to relatively OTM (higher delta) for index at higher value.

To see what SPX around 2300 would look like in low IV, we can go back to 12/23/16:

Short call vertical low IV low index value (10-25-21)

Observations:

The first two examples suggest higher IV may hurt credit, but now we see that lower IV also results in lower credit if sold at a comparable delta value.

Also note that I can cut risk 50% by purchasing the long leg 100 points NTM for only $0.45 more.

I will continue next time.

* — I have discussed two different kinds of risk here. Spread width defines risk as the maximum
       loss for any given trade. Delta represents risk by approximating probability of expiring OTM
       (full profit) as opposed to ITM (likelihood of loss).

Trader Teacher?

Today I present a hodgepodge on what I might be able to do with regard to teaching retail traders or IARs.

Stepping back to look at the process, I feel I’ve done this the right way. Nothing is ever guaranteed, but in the absence of better ideas people are often interested to emulate those who have had some success. To this end:

I have accomplished my goals to date and I have few complaints (exception: second paragraph here). I can can lose it all going forward, which serves as strong motivation to look for a better alternative or supplemental approach.

I would never hold myself out as a trading service. I don’t have all the answers, but I certainly don’t think any premium service does either. Why can’t I do what they do, then? I wouldn’t feel comfortable representing myself that way.

If I knew when I left pharmacy that I could pay a fee to accomplish what I have, then I would have forked over a hefty sum ($thousands). I made good money as a full-time (plus overtime) pharmacist. That was also shaving years off my life. For the last 13 years, I have been able to replace income and save the wear and tear on my body.

I have long shied away from the idea of getting into trader education because I believe some decent mentors do this well in the face of many fly-by-night charlatans. The good ones already have the infrastructure and experience. I would be more like a makeshift math tutor trying to cobble resources together.

Good* trading mentors and educators are worth the money they get for their efforts, and I’m sure I could do the same if I applied myself. Several years ago, I surveyed a number of trader mentorship/education services. The average rate seemed to be around $300/hour. That is less than $6,000 for 18 sessions. This seems fair. I would be heavy on the disclaimers to start because I want people to have reasonable expectations. Knowledge is never a guarantee, but I could share many things from my journey that I deem critical to the endeavor.

* — Separating the wheat from the chaff is a whole other discussion.

Naked Call Backtest (Part 1)

For the last several years, I have not been a proponent of selling naked calls. However, “necessity is the mother of invention.” Volatility does not explode to the upside; how bad can they actually be?

Here are my backtesting guidelines:

This is the backtesting period:

Naked calls backtest price chart (10-19-21)

To understand how bad naked calls can possibly be, this seems to be a pretty good place to start. SPX 2254 to 4316 is an increase of ~91% in just over 15 months: a staggering [recovery and] ascent! I expect to see losses under these conditions.

Here are the overall results:

Naked put (ROD1) stats and equity curve (10-19-21)

This is a strange looking equity curve. It certainly does not match my ideal, which would be upward sloping at 45 degrees. From inception through Sep 2020, this strategy does a wonderful job losing money. From Nov 2020 on, it looks flat. In between the two periods, it makes a ton of money.

Trade statistics indicate this strategy loses more often than it wins and that the average winner is bigger than the average loser. Overall, this shakes out to a profit factor of 1.3.

Take it or leave it?

Let’s look closer to the individual trade results:

Naked put (ROD1) results (10-19-21)

The first seven trades are all losses and position size doubles each time. No wonder the numbers on the equity curve get huge. A win finally recoups all losses and then some. Position size remains comparatively low for the remainder of the backtest (10-20 contracts compared to the high of 640), which is why the curve is flat on the right side.

One trade out of 16 saves our bacon.

Actually, what saves our bacon is not the particular trade but rather the position size. Any of the winning trades sized at 640 contracts would generate enough profit to overcome the losses.

We must not forget about risk. Portfolio margin (PM) for naked calls is 12%. With SPX at 2254, this amounts to 2254 * 100 * 0.12 = $27,048/contract. With SPX at 4316, this amounts to 4316 * 100 * 0.12 = $51,792/contract. The initial position size carries a PM requirement between ~$270K – $518K. 640 contracts carries a PM requirement between ~$17M – $33M where
M = million. This backtest includes a 64-fold increase in position size!

At this point, I have to say leave it. Even with one contract, PM requirements are too large and the MDD ($406K) is too big.

I will continue next time.