Jan 2 2021 Trade Portfolio Updates

Didn’t get as much as I wanted done because …Holidays and distractions… enough said 🙂 Despite that, I’ve hit the ground running and I am working on creating some meta portfolio management which I mentioned in my last post. The idea is to really take advantage of diversification across strategies that aren’t correlated to create a combined time series that provides increased geometric returns by way of lower drawdowns and better compounding. What Mark Spitznagel coined as a volatility tax. We reduce that and pay less “tax”. If you have a lower return each month but you have less draw down, you compound it better than a higher more volatile strategy and so on. To me, it’s all you can do, diversify (smartly) and not just for the sake of diversification but true meaningful diversification. I wouldn’t ever just put all my eggs in one single strategy in one single week with a planned capital the size of my portfolio. There’s just too much reliance on how those specific strikes and BSH will react. Plus, it’s sorta fun having previous entries mature and act as mid bear hedges, harvesting and knowing that a single entry with bad timing is only 1/10th (well really 1/30th) the portfolio is a nice thing. It takes time to build up sure but it’s like 2.5 months. Who cares.

There’s a series of OTM (out of the money) type strategies (3 of them that I use) combined with a bearish toned ATM (at the money) trade to pick up the middle bear (non crashy moves ie Aug 2019, Oct 2018, Dec 2018, Jan 2016). Each of the OTM income portion is diversified in mostly its strikes but also the type of BSH it uses to pick up during a crash. A 488 will react differently then a 484+BSH then a HS3EZ (not saying I use those well, maybe idiosyncratic versions of one or more of those) both in it’s income production and income engine as well as its black swan hedge that it utilises. There’s some diversification, it’s not perfect but we work to reduce that imperfection by time diversification across 10 week campaigns (1/10th at a time) along with 3 additional BSH/Vol hedge type campaigns. The 3 BSH vol hedge type campaigns are factory based (ie they build up over time) and they are meant as a triple redundancy insurance towards the 4 other income strategies. But in reality, they should produce lotto like returns in a crash. One of the BSH/Vol type hedges actually generates income and helps compensate the costs of the other two. We then have as much redundancy as we possibly can both in the income strategies by way of time, strike/skew diversification, and BSH diversification built within the income strategy plus we have 3 additional BSH like stand-alone factory type strategies that should provide full assurance during a a crash and most likely a lotto return. Not sure you can do much more than that.

It’s systematic and the fact that you’ve got 10 different things to manage reduce human factors at a cost of management complexity which is my job anyways.

Speaking of which, I feel lucky to have found something that I wake up looking forward to and what will likely occupy the rest of my working life. I doubt in my life that I’ll ever pursue entrepreneurial projects again. I went through my 20s and 30s setting up some successful businesses w/ my wife and two other partners that I still manage (mostly as a board member). I give over-arching direction and make sure things are running in line with the plans set forth but there’s no day-to-day which set me free. We started the business in 2004 and I finally got out of the day-to-day around 2017. I just never liked dealing with humans and human issues in the workplace. It gets complex quickly and is often irrational and I feel just out of control when dealing with human resources. I know that’s super odd to say but maybe I can expand on it. I started a software company and I am not a software developer. Maybe that helps 🙂 I have to rely on my team to correctly advise me while making business decisions and dealing with customers demands while having an expertise that was relevant but outside the central operation of the business. Make decisions, go back to team, they tell you impossible, you know it is possible but can’t be quite sure because your experts are advising you and you fight and they end up getting it done /// rinse repeat. I always wanted my “money making” life to be me and a screen and that’s it. Very few outside “human” variables, very little reliance on anything but myself, my decision and the game environment we call the market. When something went wrong, it was something that was on me. Something that I could perhaps think my way out of. Not something where I had to rely on someone else. That was my goal and though it took like 5 years to really work that out (trading is hard…mostly because you have to meet parts of yourself that you might be unfamiliar with…and protecting yourself from yourself takes practice and time..and really just a system and recognition).

In my opinion, the attributes (besides the obvious skills) necessary for successfully trading is self reflection/humility, ability to take risks and tenacity. If you lack one of those, it ain’t going to happen. The risk taking portion has to be smart, unemotional and well thought out..with outs and with a system. One thing I’ve learned in life and I’ve seen it time and time again is that you can’t talk many people out of taking risks when they’ve become emotional about it. I can list like 10 situations which made me cringe and are very poignant lessons, some are horrible. It’s a specific type of person too. If someone decides that they are going to gamble, take a business risk, buy a stock, or whatever it is that has a possibility of changing their life trajectory, I found that it’s often very hard to talk someone out of that risk even if you give them good reasons. .Once they make an emotional decision, that’s it. But, if someone is humble and self reflective you can often advise them against and they back off and reflect. If you do take that risk, you need outs and you need to become tenacious (that’s where tenacity comes in). I took loads of risks in my 20s that I should never have, and now I have a process that protects me from making emotional decisions…I did have that tenacity though and the risks weren’t emotional though they were probably way to high a risk of ruin. Unfortunately, for success, you often really need the ability to take risk, you just can’t do it with emotional baggage. When I took those risks, I’d be like fuck ok…I’m in it now, then I’d create outs and I would literally not stop (sacrifice sleep (80 hr weeks) to make these risks work out. Stupid but tenacity got me out of jams and I learned that we often take risks for excitement, for that dopamine rush and to be very mindful of that. This is why you often can’t talk someone out of an emotional risk, they have already decided they need this rush this thing that can change their life (or destroy it) because they need to feel. When you do take a big risk, make sure you have control, several “outs” and be ready to commit your entire being to making sure you don’t fail. Tenacity, Risk-taking and Humility are the key ingredients. Look at the logo on my plane tail. Badger (Tenacious little fucks).

On to personal stuff, I got up in the air twice so far since being back (quarantine affected that). What a wild experience though, we flew to Muskoka (took 24 min from Brampton), then over to Toronto to do a fly over of the city. We asked the tower to do a direct fly over of YYZ (the busiest airspace in Canada) and was approved. This is a once in a lifetime thing to do…it was EERIE cool. Not a single flight (landing or take-off) and completely empty. Here’s some pics. I’d write a whole lot more on the blog re what it’s like to do a PPL in a Cirrus SR22 if anyone had interest. I just don’t want to bore.

Back in the plane. No better place!

Downtown core (CN Tower and Sky Dome) Direct fly over

YYZ EMPTY! Busiest airspace in Canada. Pandemic effects..

My Baby. 3-4-5 Papa Kilo.

Update – Nov 25 2020

Been a long time since I posted which seems typical of my behaviour with this blog. A lots been happening, I just left Cayman enroute to Canada where we’re moving into our newly built house (will post about that separately, it’s pretty damn cool too!) but we made a month long pit-stop in KTYS (Knoxville) to pick up a tool that would help me with one part of this blog, traveling. I bought a plane.

Ashley and I both had nearly completed our PPL back in 2008 but had to leave urgently right (like literally a week) before our Check-out ride to Cayman. We had intended on coming back within a month to get it done but we just never did and then we had kids…andddd that was that. We hadn’t picked it up again until now because it was just impossible in Cayman. Anyway, we ended up purchasing an SR22T Cirrus which is one of the safest prop planes out there, it has its own parachute system (entire plane) and the automation is astounding. It’s fully autopilot and has synthetic vision, live traffic, weather on board etc.

Cirrus has been amazing to deal with, literally one of the best companies I’ve ever dealt with. They came (for free) to pick us up in the Vision Jet because we were sorta stranded in Cayman due to it being Covid free and being locked down to the rest of the world. My rep finagled it by calling it a demo. The normal protocol is that they’ll come pick you up in an SR22 (one person) and bring you to Knoxville to take delivery. In this case, they picked us all up and in the SF50 Vision G2 Jet.

That was a blast. Maybe or maybe not – am I trying to build up experience and hours to get into one of those lol. A bit of a dream.

The other thing, Cirrus just started a PPL program and we’re the first students to partake. We’re here in Knoxville for a month training every day in our plane which is pretty cool. We’re less than a week away from Solo. In our off time, we’ve been mostly hiking and enjoying the outdoors since in Cayman, we were quite limited to just the beach.

We started off flying the club plane (because our delivery was Nov 18th). I have some slight PTSD from the training. So the call sign 8-6 Mike Juliette brings me some pits in my stomach. The instructor was extremely tough on us.

During training one day, we landed and saw our plane had made it to KTYS (Knoxville) for prepping before delivery. Got a snapshot before they put it away.

Here’s some delivery day photos. What a day. It really was like 10 years in the making. The original plans we had in our 20s was to become pilots and live that freedom. Just life and kids got in the way. Now with the kids in distance/home school there was no better time to dedicate a month to training and eventually instrument rating in the winter to finally be able to cross country. The thing is damn fast and has a great range. 1000nm (~2000 km) and boots at 187-200 kts. It can go to 25k feet too and is equipped with oxygen and FIKI systems.

Here’s our first Cross country (Ash flew there and I flew back)

As for trades,

I pretty much de-risked into the elections and was mostly ATM trades. I’ve added 10-20% sizing in the last week or two but am looking towards eventually setting up a 488 campaign now that we’re out of high vol. I did put on some Feb ATM SPX trades and I am playing with similar BWB setups in TSLA (given the recent momentum move up and iv spiking again). So I’ll be looking for opportunities in 488 and BSH factory build up as well as dabbling in ATM. That’s about it.

I am >30% for the year and happy that I’ll probably hit 40% for 2020 and move on to a more stabilised systematic approach in 2021.

Jul 30 2020 BWB+Fly Aug Trade Update

A nice pop in the p/l given the US is contemplating giving up on those pesky elections. Who needs them 🙂 Delta sitting comfortably at -800 and given the DTE, any moves towards -200 delta and I’ll just start peeling off the trade piece by piece removing risk as I go.

Sep BWBs are currently going for about 95c credit and Oct BWBs are going for about 2.25c. I’ve got loads of flies up in Sep so I can purchase BWBs against those but I didn’t get any in Oct yet so I’d have some exposure to downside if I get some of the Octs on. Not terrible given the deltas I’ve got built up in Sep so I’ll probably put some on today. Usually I like to start with the flies. It’s no different than just entering a rhino/bwb though which loads of people do without the fly hedge/combo.

It’d be a huge milestone to close the Aug at 500k P/L. It’ll call for some real nice champagne. But I won’t fixate on it, I’ll just manage that risk. Huge month so far and I think July is sitting at just over 7% P/L and Aug will likely be similar. Cannot complain and thankful the market keeps on giving.

Had a 30% year last year and I gather I’ll get towards 50-60% this year solely from the opportunities. The last few months, I’ve just been concentrating solely on building that long vol BSH up and trading these Rhino/BWB combos but it rarely takes much more than 30min a day, things are boring when they are producing. Many traders say you’ve made it and are barking up the right tree when you’re trading a system thus eliminating human factors and bias and subsequently the actual act of trading becomes boring. The latter part is true right now, the former isn’t based on a system per say but it will be once this environment ends.

Jul 27, 2020 – August BWB/FLY Trade Update

We ended Friday at a delta of -900 after adjustments and now sit around -1700. That shows you just how quickly negative delta you get with time even just the weekend. The position is hovering around 285k P/L so it’s seen an increase of 35k over the weekend. I’ll have to adjust the upside today and by Thursday this will be done with removals from the structure rather than additions to it. There is 25 days to expiration and I’ll aim to remove risks as we go from here until it’s a benign structure that can be expired.

Jul 24 2020 – The Big ATM trade update

Here’s an update on my big August trade that has about two weeks left in it. It’s starting to actually look like an old school ATM trade given the reduction in VIX and the lack of credits in 30 DTE or earlier trades. From March till June, credits were huge and upside risk NIL. Now as opposed to then, I actually have to use some upside adjustments aggressively.

I started adjusting for upside exposure during this little fall towards 3200. My overall deltas are sitting at -900 and I’ll close out the day at that.

Delta: -939

Theta: 21,956

Vega: -10,567

The position represents 5MM in planned capital and is sitting at 251k profit. I’ll dance this thing into Aug 7/8th and continuously remove risk and adjust. There’s a small chance for an extremely large payoff (the biggest I’ve ever seen) @ 1MM in 1 month. Reminds me of that show 2months 2million. Ridiculous but it is the environment and the opportunities. These types of trades won’t last. For now, I’ll happily let it beef up the account. I’ve got BS protection in case we have some sort of massive gap down.

Here’s the trade looking forward 7 days

Here it is where I expect to close it. It won’t look like this later as I’ll be constantly adjusting back and forth between now and then and the negative deltas will continue to build up as time passes

For a bit there, the VIX hit around 24 and it looked like the ebb and flow trade was about to get a lot harder but today we can now get a Sep BWB for $1.00 credit. So we’re still going for now 🙂 I got some on to offset the Sep position which I started with symmetric flies back at 3260-3270. I’ll be very happy if we can keep getting these conditions for the next 6 months.

In a large fall, and if we approach -400 delta, I’ll start to adjust for the downside and I’ll offset with some way OTM calendars in case of a bounce. I have two trading weeks left for Aug position which will get more and more negative delta and have more and more protection to the downside. If I am forced to adjust for downside next week, it means we went through 3150 area and to offset the nuance of continuously increasing negative deltas, I’ll use some way OTM calendars for upside protection while adjusting for the asymmetric risks on the downside.

I gotta say, I feel kinda lucky that I was also able to start the September position, I wasn’t sure I’d be getting the same opportunities with BWB pricing. Perhaps this continues on for the rest of the year re elections in Nov. Eventually I will move on to a 488 campaign, BSH factory, TAA and ATM at lower PC.

Jul 16 – ATM Trade Update

I’m hitting (well above) negative delta limits on my current Aug ATM trade and am looking at ways to reduce it now that July expiration is over and that was providing me some positive deltas. It’ll get more and more negative delta as it progresses into the month so I’ll deal with it daily and continuously raise up that Upper expiration line. This trade represents a planned capital of 5,000,000.

I had the deltas in line a week ago but the reduction in vol and time passing has brought them quickly out of line. The BWBs in August are no longer giving a credit but would give some positive deltas and theta/risk. I think I’ll save those for a larger down day. We’re down about 0.75% today so I’ll have to start looking at PCS maybe even some call structures (call calendars or call BWB). I haven’t had to do that yet post crash as the bwb credits were sufficient in raising that UEL and eliminating upside risks.

I am looking at 3325 calendars, 3250 calendars (mixed) along with a 11 delta 75 wide PCS and I’ve already got some long ES to temp hedge.

So yeah, let’s go over the Aug position:

It is at -1450 or so delta and has pretty significant upside risk to the already existing profit of $125k. So we have to do something. We do benefit from vol release on up moves but it’s not enough. I’d like to get it down to about -700.

Here’s the trade looking forward 14 days

We’ve got massive theta, great risk reward if we get our deltas in-line and decent non-black swan downside risk profile. The previous expirations (from May till now) were a lot easier on the upside so this one will be a bit trickier.

Post Covid Crash update – May 5

Been a while, I should have kept posting through the whole event. I am up about 20% on the year which is decent given the events and given several mistakes I made. I’ve since revised how and what I do in my process and can only be thankful I ended up positive through-out.

Bizarrely, I was super in-tune with the whole virus thing back in late January as the first reports were coming out of China. By early Feb, I had got out of my entire standard equities portfolio (TAA –Tactical Asset Portfolio blend) and purchased 400 long puts ~ $1.00-$2.00 in anticipation of some volatility thinking I caught it earlier than the market. The market just kept going up and up and up until Feb 24. I had no real OTM trades on and had built up some long-vol portions but the nuances of en-cashing was where my regret lies.

On Feb 28th, I started cashing out of those 400 long puts which took a beating through the mid part of February. Had I kept them on till March 24th they’d have been worth millions. Just before that, on the 27th, with the VVIX spiking the highest since Feb 2018, I also started opportunistic OTM trades that got annihilated despite being hedged with Black swan hedges. A poorly timed entry, every indicator was flashing off so I should have waited for a bottom signal before entering but at the time I figured that the virus news would cause a more lengthy decline with several bounces in-between so I figured I could get in and out using vol relief on the bounces to capture profits. I was wrong. The mess lasted till Mid March and lost a bundle but was offset by my long-vol and BSHs. Though, I did take a pretty big temporary hit on mark-to-market throughout. Anyways, to go back a bit, on the bounce in early March, I picked up another 450 long puts at 1800 for $3.00 and I was going to convert into a BSH factory but the market collapsed almost immediately after I bought them (lucky). So I followed the trend down converting slowly into fully formed BSH and used them to hedge off the OTM trades. I was keeping that left tail popped up. By the end of it all, the combo was green and all was fine.

In Mid March, I started using OTM calendars on bounces as an income capture. As well, to offset the long vol hedge that was incredibly negative theta positive vega until I got a signal to encash, I started selling 5-7 DTE puts in ES after-hours at ridiculous prices whenever they came up and used that against my long-vol (calenderizing the long vol hedge that was 90 DTE). This all worked out really well and I was able to capture some really ridiculous pricing. I saw 1000 SPX puts going for like $10 I am pretty sure.

By April, I started doing BWB ATM trades on dips for large credit (usually they are $4 debit!) with 40 DTE. On bounces, I’d add symmetric flies. I’d rinse repeat this in a nice ratio to maintain decent profile and am still doing this now.

I’ve become a fan of using trend indicators for risk management and that’s where my interests lie right now. In this environment, I’m setting my portfolio to be mostly locally concave with respect to selling premium (ATM income trades) yet my overall portfolio will be global convexity (long vol). I won’t sell asymmetric risk rather I’ll own it by using some BSH type factories and some usage of OTM strangles and I’ll sell more defined risk upfront with ATM type strategies. It’s the environment we’re in and with the credits (removing upside risks) in the BWBs, it makes management much easier.

Since I am doing my own blend of things I can probably start posting more risk profiles and trades so I’ll start doing that.

May 14 (Update 2) – STT, Long term base portfolio and travel plans

Yesterday at about 2803 I was able to sell puts for my factory and in one single day I am now able to form a BSH for profit (free + some). I got 30 units (90 short puts) on within 8 hours. Epic.

I also started the equities portion of my long term portfolio as my base (I did a combo from allocate smartly that has a historical of 10.4% annual with a max draw down of about 6.1%). Good base portfolio. Today I got the treasuries/bonds portion on 🙂 good timing. I will now let that run itself without messing about. I had it on at 2940 area but didn’t like the timing re the heavy portion in SPY so I closed it at the highs 2949 and now just re-opened. It was more like a mulligan, my plan isn’t to mess about with it and I won’t from here on in.

YTD is now 15% (3.35% a month) and that’s on actual total equity. Nice!

I am going away for my next portion of the summer/spring vacations. I’ll be starting in Montreal for the party millions event and I’ll make my way to Ottawa to meet with my programmers in development office and then take in the Iliza show (for my wife). After that it’s on to Toronto to check out the start of my new house build there and then make my way to Moab for a glamping style wedding and after that…. Vegas for the WSOP!

In preparation, I’ve closed off most of my older STTs, cleaned up the account and prepped ONE. I have on some Aug, Sep and Oct with margin available for another 100 or so units if we get another vol spike/decline. The Aug is acting as a hedge to Sep and Oct but also has the most theta of all three months. October is now profitable (+11k) as predicted it would be by end of week.

May 14, 2019 – Trade Plan (STT BWB + BSH)

I ended up closing out my Jul 18 and Jul 31 STT remnants at a pretty awesome profit. I am left with August, September and October. The Aug and Jul ended up acting as moderate hedges to the Oct/Sept expiration which actually put my balance higher through the modest volatility events last week and put it right positive in the past two days. I am on target for a 20-22% H1 2019 and will end June at around 17%-18%. Exactly as predicted and planned.

That’s the beauty of running these in expiration campaign style. The older ones protect the newer ones and everything just meshes together perfectly. The older ones will hedge the 3-8% drops as you fall right into their built up profit zones and anything greater than 8-10% will be likely covered by the BSH OR you’ll have time to roll (if it was a slow grind) either way you’re good and only dealing with modest drops in P/L. Feels like a beautiful well oiled machine now.

I am not straying or considering much else in terms of trade types for the main portfolio. I want a clean year of just STT+BSH and I want to be a master of just one main trade type. I doubt I’ll deviate much other than finding more efficient ways to adjust.

All in all a good year so far.

May 6 2019 – Trade review (STT+BSH)

Nice little vol pop there. When I saw the tweet yesterday I knew to expect a very rocky futures open and when it got to about -2% I almost thought we could have a repeat of Aug 24 with a -5% open only because of the swiftness of the fall and the potential reaction when Europe opened. Alas, we swiftly found footing and the market rebounded and sits currently at 2920.

Funny enough, I had a portfolio on for my base via AllocateSmartly but didn’t love my entries and sold all of it Friday along with all my other longs. Good timing 🙂 I also harvested all my older STT and BSH last week and removed a ton of risk. I mean I have 600 net long puts in May 31 expiration and my Aug/Sep STTs were harvested. I wasn’t breaking a sweat last night even if we did open 5% down. Even today, I am neutral delta without a single adjustment.

Today, I am using the bounce and increased volatility to add some bearish toned STT. The bounce gives me better delta and the increased vol allows me to have a longer upside runway. Pretty much all I’ll be doing today.

My newest Oct STTs are taking a bit of heat, down about 300 a shot x 40. They were quite positive upper expiration line and roughly +50 delta but I have -delta older ones and I am adding some bearish toned ones now. Within a week or two they’ll be positive if all things remain equal. As time goes on, the trades get more and more -ve delta.

I gather I’ll get the account up to about 20% for end of June for the year. Which is roughly the target. I am hoping for 25% but we’ll see how this plays out. If we have more downside, then I gather I can get even more as we enter the tents of matured trades but if we runaway upwards, it’ll just be the standard lower profit. My goal is to consistently hit a yearly 50% with STT+BSH on total account value w/ compounding and opportunistic over-leveraging on significant down moves up to 1.2x. I won’t be deviating strategies or diverting any funds away to other trades. This is a year long real money test of real market conditions and actual trade results for the STT+BSH combo.

I’ve been researching T5 a lot lately but it’ll be far separated from my main account. There’s a lot of opportunity with that trade and its juicy AF but it’s more fitting of my older previous life as a professional gambler. You have to look at it like a weighted coin flip in your favor but with regular total losses. I have to analyze Kelly criteria and risk of ruin as well as all the trade mechanics and market environment entry type stuff. Big project. Re what I mean : if you have a 55/45 edge in a coin flip, and you have 50k total, how much do you bet per hand to eliminate risk of total ruin so that you can infinitely take advantage of that significant edge? Is it 5k a flip? 2k? etc. You have to analyze this differently then something where you put all your equity in every trade and try to eliminate max draw down. Rather you accept the 100% win or loss and determine the edge and calculate the bet size. Should be interesting.