Ron Bertino – Travels and Trades

Risk, back-testing and drawdowns

When I first started out in options a decade ago, there were only basic backtesting systems, namely Option Vue (which, actually just recently went out of business due to lack of adapting and other reasons). It was not only cumbersome and slow to test but the datasets were very limited, we didn’t have the option data in a variety of market types to really test out strategies. We basically had EOD data pre 2011 and I believe 30 min data after that. That gave us what? Like 3 years of good testing ability. Further to that we had less expirations.

This is an era where trades like the Modified Iron condor were popular. These sets of strategies were borne from the limited data set I mentioned above. They had produced consistent unchallenged small gains for a handful of years only to be dinosaured when the inevitable bulldozer came while picking up these pennies (ie Aug 24, 2015). With this new data set and many more to come (Bear 2016, Low vol 2017, Feb 2018), many other trade types started to be developed, using a much more varied market data set. It was also when the first inklings of the pre-PMTT group came about when I started a skype group to talk about the Rhino trade. From the ashes of these previous trade systems, our group was born when Ron took the reigns and created PMTT.

There’s been a lot of talk in my group about curvefitting and having OOS periods now that we have access to automated tools where we can essentially backtest loads of iterations in very quick time. It’s true, when I backtested the HS3EZ, 488 and 484+2LP it took 100+ hours to properly do. I had one set of parameters and if I changed them, that’s another 100 hours :). I am certain I’ve spent 2000 hours+ backtesting in the last decade, if not more. We can now test that AND any changes in a few minutes. This creates a problem of fitting data by removing losing trades by filtering w/ new parameters etc etc. I am betwixt between the two camps of thought when speaking about the PMTT type trades only. When I am looking at the algo trading or TAA, I am firmly and obviously very focused on OOS testing and curve fitting. The edges are less and the variables much more variant. You’re searching for small edges that need a LOT of data to confirm because the edges can be or can come from something much more ambigious as is the case in algorithmic trading. It’s a definite concern for PMTT types of trades, but just not as much.

The PMTT type of trades are not the same thing as algo trading or trading futures or utilizing parameters like the TAA guys use which have less pronounced and even ambiguous edge with much more variables and variability in those variables. Our edge comes from the very robust premium inherent in the market of which acts like insurance and the pricing of this insurance is less variant and affected by less variables than other non-option trade types. The pricing of an option is via the corresponding greeks which I view as almost like a device of rubber bands which can only stretch and pull so far. We don’t need 1000 samples of bear markets and 1000 samples of low vol periods. There’s only so much that can happen in our structures. With that said and related to my betwixt comment I believe that any strategy created from a limited data set needs OOS testing before going full hog, especially if you’re only testing from 2020+. Which I am currently seeing a lot of. I firmly believe we should be using all data available to us to create these strategies (that means 2014+ at very minimum). This gives us the 2014 Oct crash and unrelenting V-Rally, the 2015 crash, the 2016 prolonged slower bear, the 2017 low vol run up, the 2018 crash, the Oct-Dec 2018 bear, the 2020 crash and subsequent huge 2021 rally and so on. I think a strategy can show returns in a full test in those markets as well as random sampling within AND it has a solid hypothesis and theory of why it should work, then it is robust enough for me to slowly add in.

In regard to risk and draw down, I also believe you can appropriately reduce overall risk with solid well thought out and well tested diversification and trade development and you can in fact limit max draw down on the portfolio of trades by doing this. By limiting draw down you increase geometric returns.

I don’t think drawdown equals risk.. It is just not that simple. You can diversify, you can mitigate, and you will have better geometric returns because of that. Risk mitigation=return. My life is just focused on this aspect, reduce risk and draw down for better geometric returns. There is volatility tax and it’s much more attractive to limit your draw down to allow for better compounding. I always say this, but its the time series of returns, the pathway we take in our bets, that is the most important.

Meta Portfolio Compositions and back in the grind!

Made my way to our new temporary home for the winter and spring. The place will be our forever home in Canada and act as our main base. We still are trying to figure out if we’re going to make our way to LA for the kids education but we’re getting tired after this last build and move so who knows. That said, I miss how easy things were in Cayman, it was like a free-for-all in terms of pretty much anything/everything re being able to just live life. I am met with blocks on everything here in Canada. Everyone seems to want to create problems. It’s bizarre. They won’t even accept my international license or cayman license and want me to start off with a learners permit, they’re having a fucking laugh. I’ll just continue to use my Cayman license, just means I can’t register my cars until I can find some Canadian insurance company that would insure me without a CAD license. I also find myself talking on the phone to customer support for hours a day for a variety of things as well. Real life sucks apparently lol.

We’re here until at least the summer and though we’re 90% going to LA, there’s a small chance we’ll fall in love with this property and stay here. Though, man, I just don’t know if I can “regular” life it here like I said above. It’s probably irrational but there’s a lot of weird feelings about raising the kids here and I mean, its fucking’ cold. Though, having the plane now gives me some pretty cool options to escape and the hangar is literally 12 min from my house. I can fly to Myrtle beach in like 3.2 hours for instance. The property is 100 acres located just 25 min from Toronto international. So the location is perfect and close to the international airport and acts as a great base to our families (we’re both from area originally and our families are here). That was the intent…have a second home near our families but it became much much more than that as the project developed and the budget increased…..

One of my best friends designed and built it same as he did for Cayman so it’s been a fun challenging project and his tenacity for efficiency, his skills and his ability to keep the project a value creation device has allowed for a valuation much higher than what was put in. So I am super happy and both projects have provided me with value. He’s been actively helping me manage investments so it might be his pièce de ré·sis·tance or swan song as he moves more towards trading. Or perhaps he continues on but treats it like a hobby or it’s a bit of both. Who knows. Here’s a few cool pictures of the property (which isn’t 100% complete yet but liveable). It’s got a VR/Sim room which will be decked out with a star wall, RGB lights, and 4 setups (our family are PC gamers…no XBOX whatever or PS whatever allowed in here!). We have a sweet swimmable hot-tub on the second deck, an infra-red sauna, several cool fireplaces, a speak-easy etc. It turned into a true chalet like experience. Our furniture hasn’t yet arrived but I think it’ll be here in 1.5 weeks. We’re making due with what we have, it’s exciting because so much is not done and we’ve got limited furniture so it’ll only get better. Fun and frustrating at the same time I guess.

Probably the only space that’s 95% completed. The entry.

The outdoor ceiling is not complete yet but it’s coming!

We landed in CNC3 a few weeks ago and hangared the plane. I still need some more hours but the weather has been shit and instructor availability as well. Things happened slower then I hoped. I really wanted to come back licensed fully.

The entire break I’ve been concentrating on meta portfolio construction as a means to reduce drawdown and increase geometric returns. I’ve come up with using 3-4 OTM style trades that we talk about in the PMTT Group as a base income producer and with my own spins and each are composed of 4 different types of BSH. These are put on in campaign style with the average being about 10 weeks of campaign. This gives time diversification. So we’re now diversified in entry timing, OTM income production and BSH provision. On top of this, I combine 2 black swan type campaigns that provide additional protection over all. Then I have an aggressive harvesting style that really translates into back ratios at a variety of strikes on older maturing trades. So basically, 10 different time entries, 4 different strategies, 4 different BSH styles, a bonus 2 hedge type factories and harvesting. About as tight as you can get.

4 Types of Out-of-the-money income strategies put on across 10 weeks giving time, strike(skew) diversification
4 Types of BSH protection put on across 10 weeks giving time, strike (skew) diversification
2 bonus types of BSH factories/hedges put on in campaign style across 4-6 weeks giving skew and time diversification and 2 additional fail safe swan protections
Harvesting aggressively all structures that are matured

You’re left with creating less draw down and increasing compounding returns which is equally important to the trade strategy itself. It add complexity sure, but I mean, this is all I really do now and it’s systematic. That’s a preferred method for me.

I’m finalising all the time series for each of the campaigns from 2014+ and I’ve noted that there is adequate response differences to a variety of environments and together they provide a smoothing of return. In my mind and as I mature as a trader and as I have started getting consistent results, I’m convinced that the key to success at trading for a living comes with diversification both in time and in strategy. You take 6 known alpha producers and you do 1/6th each. It helps with human factors, as you’re much more likely to follow the system/rules if it’s just some annoying small part of the portfolio not the entire thing. The options market has a funny way of causing you to draw down from the tops.. You’ll be sitting at 80% profit target and one day you’ll draw down to 50% for no reason (market hasn’t moved) and you’re becoming price fixated and often times it does preclude a vol event and from there you’re just waiting for that old 80% to come back because you think you can rely on time. It’s a fools errand not to follow the systems and rules. You’re much more likely to do what you need to do if it’s just a 1/6-1/8th portion of your portfolio.

As mentioned before, the last 6 months have been pretty much straight opportunistic ebb-flow ATM style trades taking advantage of the environment. I’ve just started implementing a systematic portfolio based on the above post and from there that’s all I’ll pretty much do.

I am back at my desk for 8 months so I hope to blog more and post interesting things the best I can.

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 15 – Update

Given the events of February/March 2020, I had to re-evaluate risk and its presentation in each of the components of my portfolio. Though it was beneficial to add what I consider a god level data point for backtesting purposes, it was not fun to go through. It was the fastest decline and recovery in history. There is no tougher environment to trade through with complex non-directional options strategies. I ended up positive through the event despite the fact that things were broken in the market structure. Things happened that should not have happened. I saw things that I am sure I’ll never see again. This allows me to reconsider risk through what was one of the most market destabilizing events in history. This breaking of various markets and market components has given me a peek into what was naked when the tide left and allowed me to dig deep into my compositions and fine tune with risk management as the main motive. It motivated me to create a systematic approach to my base trades for entries, exits and adjustments. It took 4 months of hard work, but I’ve designed a system that accomplishes all of the risk management goals while maintaining returns that will compound better than before due to the reduced drawdowns. The key to this is maintaining global convexity despite being locally concave in risk profile. This means that risk where it is defined and quantifiable (local risk) while maintaining/financing the ownership of global convex risk on the tails. Short locally and long globally.

The more variant a portfolio is the more it impacts your geometric return. I have an edge, but if I am in extended drawdown, there’s less capital exposed to that edge. The less you draw down the higher your geometric return. It’s the power of compounding and is what Mark Spitznagel calls the volatility tax. The big losses are all that matters to your rate of compounding. Makes sense right? Manage your risks, maintain an edge and let compounding do its magic.

My primary interest lies in the long volatility tail space and coupling that with localized complex option income production. Globally convex locally concave. The long volatility tail portion of the my portfolio closely corresponds to what Universa, Nasim Taleb and Mark Spitznagel research, it’s a convex payout on extreme market events. When you tie in global convexity (extreme payoffs in extreme events) think of the convex shape (shown below) with local concavity (necessary for regular income production), you end up with the best of both worlds. Absolute protection and income production on the tails (which are rare) coupled with regular income production locally.

The composition of both elements in the options space has benefits that are astounding as it not only gives you capital during turmoil but it protects both a traditional portfolio as well as one composed of options. You prevent event draw downs and have made significant returns that can be actioned at market bottoms. That effect is exceptional. The combination of long vol with a traditional income strategy is what allows for the highest geometric return profiles.

Coupled with the long vol tail hedge, I’ve worked on systematizing the income strategies that are completely mechanical in nature. There is no room for human bias. I worked out a mechanical system that has no decision bias in both the long vol component as well as the income production component. It prevents the human factors issues that can cause mistakes and under performance.

We’ve got so many great data sets now, we’ve got the vol events of Aug 2019, the bear shocks of Oct and Dec 2018, the volmageddon of 2018, the time skew issues of Aug 2017, Aug 2015, Jan 2016 and so on. We’ve got a plethora of data. The period from February to June of 2020 used this data to do a deep dive into restructuring the portfolio and analyzing its risk factors. It was long, arduous and sometimes frustrating when you realize that everything has risk and the only true way to eliminate or minimize is by true diversification.

The lock down forced me to work long hours daily to re-evaluate my systems and to fine tune a new system setup. This was a period of heavy backtesting, reading, daily hour long phone call discussions with a trade buddy, trials, and analytics. I left no stone unturned even exploring things I would normally say was trade style heresy. The main discovery is the need for systematized approach in all base core strategies. The management is systematically rules based. My entire portfolio will follow this tenant. It’s a minimization of human factors. As Jerry Parker puts it :

“We are not really interested in people who are experts at the french stock market or german bond markets due to technical nature of trading…it does not take a huge monster infrastructure: neither Harvard MBAs nor people from Goldman Sachs…I would hate if it the success of Chesapeake was based on my being some great genius. It’s the system that wins., Fundamental economics are nice but useless in trading. True Fundamentals are always unknown. Our system allows for no intellectual capability.” Jerry Parker

Related to the above statement, I’ve had a realization to systematically use quantitative analysis and trend indicators to manage trades with respect to risk, entries and exits. QA gives me a way to manage the trade risks systematically while keeping me on the right side of the market trend, it’s what the university endowments use and it’s what Jerry Parker helped systematize in the 80s and 90s. I am using it to err the trades in the direction where the sum of the quantitative analysis points us. The delta adjustment range is -3 to +3 per unit. If it’s a bearish trend, we’ll keep it in the -3 range and if it’s a bullish trend we’ll keep it in the +3 range. Lastly, it lets us know when to exit trades. If we use Vix/Vix3M ratios, force index, OBV, ATR expansion etc we can avoid every major event in the last 10 years. I have now incorporated mandatory exit signals. If the signals do not show and we have a black swan, that is protected as well because of our long vol component.

It’s important to have a system that removes emotions and biased decisions. It removes human factors and that gives you something that’s concrete and sustainable. Decisions cause fatigue especially when tied to large money. Through the lock down, I tried investigating several things with an open mind, including taking advantage of zero day premium trades (PR hedgies) and cycle indications trades. This led me to making polarized decisions on an hourly basis. That’s not sustainable, it’ll exhaust and it’ll burn out. It solidified my requirement for a systematic rules based core portfolio. You can adjust/fine tune the rules but you cannot disobey them once they are live.

Aug 23 – Less Talk more Rock

Less nuanced talk…

After reading my previous posts, I realised just how nuanced the language is and how it’d be only relevant to a few people which got me thinking that it’d be interesting to try to explain all of this in terms non-complex options traders could understand. I mostly write this blog for myself as a record of my thoughts, plans and actions as well as for entertainment and perspective differences for all the crew in the mastermind group.

I guess I’ll start with where these ideas came from and what the style of trading is.

We’re a group of people that came together with vastly different backgrounds and strengths. It all sorta started when Emeric and I formed a Rhino trading Skype group back in 2015 that ended up attracting hundreds of people, including Ron Bertino (the founder of PMTT). That ran for a few years and Ron ended up taking over the admin portion of the Skype group (I can barely keep up with a travel/trading blog let alone managing and admin’ing a large Skype group) and eventually we all moved over to slack via the newly established PMTT group. Most of us have been working together for the last 4 years trying to explore and tackle the dart arts of “out of the money” complex options trading. We are a vastly diversified experienced group that includes quants, some professors, some fund managers, some managing 10s of millions of their own money and others are straight up small retail traders and even others that barely trade (Delayvis) and are mostly in it for the intellectual challenges. The area that we are dabbling in was quite unexplored and very nuanced. We’ve had our ups and downs and certainly had our egos kept in check with a lot of explorative strategies that went sideways after much research. Why? I explain below.

Many of our models fail or ideas failed and the current modelling software available still hasn’t done a great job of predicting risk curves and market responses. We try to remove or mitigate most of those risks (Out of the money options risks) as well as modelling differences in an effort to capitalise on this alpha (the additional return). The alpha mainly comes from the premium in the markets (the need for insurance from big portfolios etc) as well as being one of very few groups likely exploring the areas we are exploring. When we started in 2015/2016, we only had end of day data for options from 2008/2009 and on and really the only testable data was 2011+ with incremental hourly data. This means that things we’d test really had very limited data sets and when you got into super complex positions though they’d test well and the modelling software would show reasonable profiles, they’d eventually get busted up in live trading. This constant evolution coupled with the fact there are very bright minds in the group has bolstered the testing, strategies and executions to where we are now. It’s eliminated a lot of types of trading and eliminated a lot of the unknowns that we experienced previously. Out of the money options trading really is a dark art like I mentioned at the beginning. We do have a lot more data now in tumultuous periods like (Feb 2018, Oct 2018, Dec 2018, May 2019 and Aug 2019).

So what are we really doing at the very basic level?

We’re insurance salesmen who also insure ourselves. That’s it.

Options can be thought of as insurance. A person can buy insurance at any level in the market (known as the strike). Someone might say I only wanna lose 2% max in their portfolio and they can purchase insurance 2% below the money. Another might be comfortable with a strike 10% below the market and they can purchase insurance 10% below the market and so on. If the market is at 2900, you can buy insurance at 2895, 2890, 2875 and so on. The prices of insurance vary at each strike. Now as we all know, insurance prices in any industry has some fixed things in the pricing and a pricing related to risk (is it likely a hurricane is coming, pricing goes up!) this is the same as “fear” when related to market insurance. As you can imagine, each price of each level of the market can vary in how it responds to an event in the market. The 10% below market has a “fear” portion as does the 2% strike and this amount can vary for each strike based on market pressures not only at the time you put it on but how it reacts to any event. This is kinda known as skew. It’s pretty much unpredictable in any real sense except when it gets stretched or abnormal you can expect a reversion to mean eventually. Also, every insurance contract has an expiration date. The closer it gets to that, the less value an insurance contract has until the risk portion of the premium gets to zero at expiration. That’s our theta (or the average amount the contract will lose every day (we gain) with all other things remaining the same). So we sell insurance for a premium but we also buy insurance in this complex setup of contracts that creates a risk profile graph. All of the positions we enter will generally have a positive theta (a time based deterioration of value that benefits us). For instance, my current portfolio has a theta of 11.5k a day. Which is on the high side but that’s because we just came out of a high volatility period where the premiums got jacked up and now we get the benefit of it having to come out before the contracts expiration date. I can expect to gain that over time and on average every day but if we have a super negative tweet from Trump about the trade deal, I can expect to take a hit on my account because my trade also has what’s called negative vega. Which is it responds negatively to volatility. Generally, a positive theta trade has negative vega. My negative vega is currently 100k! If the volatility in my options go up 1 point, I can expect to take a temporary draw down of 100k. This is the price we pay as risk brokers. But! as you can imagine, as time goes forward, there’s less and less days in the contract and less and less vega can affect it. Vega acts on the time portion of the insurance contract. That’s not considering weighted vega effects re OTM but that’s for another day. Just speaking in generalities.

Options can be thought of as insurance. A person can buy insurance at any level in the market (known as the strike). Someone might say I only wanna lose 2% max in their portfolio and they can purchase insurance 2% below the money. Another might be comfortable with a strike 10% below the market and they can purchase insurance 10% below the market and so on. The prices of insurance vary. Now as we all know, insurance prices in any industry has some fixed things in the pricing and a pricing related to risk (is it likely a hurricane is coming, pricing goes up!) this is the same as “fear” when related to market insurance. As you can imagine, each price of each level of the market can vary in how it responds to an event in the market. The 10% below market has a “fear” portion as does the 2% strike and this amount can vary for each strike based on market pressures not only at the time you put it on but how it reacts to any event. This is kinda known as skew. It’s pretty much unpredictable in any real sense except when it gets stretched or abnormal you can expect a reversion to mean eventually. Also, every insurance contract has an expiration date. The closer it gets to that, the less value an insurance contract has until the risk portion of the premium gets to zero at expiration. That’s our theta (or the average amount the contract will lose every day (we gain) with all other things remaining the same). So we sell insurance for a premium but we also buy insurance in this complex setup of contracts that creates a risk profile graph. All of the positions we enter will generally have a positive theta (a time based deterioration of value that benefits us). For instance, my current portfolio has a theta of 11.5k a day. Which is on the high side but that’s because we just came out of a high volatility period where the premiums got jacked up and now we get the benefit of it having to come out before the contracts expiration date. I can expect to gain that over time and on average every day but if we have a super negative tweet from Trump about the trade deal, I can expect to take a hit on my account because my trade also has what’s called negative vega. Which is it responds negatively to volatility. Generally, a positive theta trade has negative vega. My negative vega is currently 100k! If the volatility in my options go up 1 point, I can expect to take a temporary draw down of 100k. This is the price we pay as risk brokers. But! as you can imagine, as time goes forward, there’s less and less days in the contract and less and less vega can affect it. Vega acts on the time portion of the insurance contract.

Let’s give an example, lets say I sold insurance for hurricanes pre hurricane season for 5k and it expires in 4 months. I take on all the risk of hurricanes and I get 5k to do so. If I wanted to offload my insurance contract to a re-insurance group. What would I sell it for? Well if I had 3 months left, I’d probably say hey I’ll sell it for 4k (pocketing 1k) because there’s 1 month less risk. What if there was 2 weeks left? Well, shit, I took most of the risk and there’s like only 2 weeks left, I’d sell it for say 500 pocketing the 4500. That’s theta in a nut shell. BUT we gotta figure out what Vega is! Let’s say there’s 2 weeks left but news just came out, there’s a hurricane barreling down towards us. its a 15% that it’ll hit, what do I sell it for there? Well there’s 2 weeks, we got a 15% chance, so it’s definitely higher than the 500. That’s vega. What if it was 50/50? Vega would act on the 2 weeks even more. But as time ticks, every day the vega effect is less and less. What if we had 3 months left and we got a report that it’ll be a very active hurricane season? Well, that would probably put me in a loss position for the insurance I sold 1 month earlier.. but only temporarily. Vega and Theta are interlinked.

It’s kinda a fun game. For instance, lemme go through what just happened to my portfolio in August..

I was pretty much entering in low vol which really wasn’t what I wanted to do but I wanted to keep the theta coming in, and I wasn’t yet convinced about exploitative STT trade entries. I understood any transition to higher volatility would bring on draw downs (though usually temporary). I sold insurance when no hurricane was on the horizon, just trying to get the basic premium present in a non fear market. However, I was only like 40% invested. I saved the other 60% for higher vol entries (opportunistic). Then came the first move from 3020 down to the mid 2900s. I slammed on some since it was the biggest down move we had since like May. Then I fist pumped slammed even more on when we touched 2920/2930 area (the forecast was suggesting hurricanes were kinda possible). VIX was still relatively low, but off the lowest of the lows. That means that the insurance premiums I got were meh but OK. Probably VIX (vol index) 16. Then came the down move of the first weeks in Aug. Skew/VIX acted a bit weird (An expectation of that a hurricane was coming). The insurance I sold went up a lot in value (a draw down) but my black swan insurance barely activated (the hurricane didn’t arrive to activate the swan insurance but the fear was maxed out) thus I had a temporary draw down of about 7-8%. Now, usually on moves like this, the BS insurance activates a bit more. My expectation is that any further large down move it’d kick in and we’d start going towards even…but I am concerned (as mentioned in my last post) about how the volatility regime has changed and wondered if there is a path where the STT can continue down in PL and BS doesn’t activate. In either case, it’d be fine just a bit stressful. If it continued down and BS didn’t activate, I’d roll the structures, I’d probably have a max draw down of about 10%. The new STT would be extremely juicy and extremely resilient being very very very far below the market which is a great thing but we wouldn’t b feeling so great here being down 10% on the roll. As vol subsided and time moved on, I’d eventually get profit out of it and of course correct the draw down. No-one likes a draw down and it feels like crap so it’s not like its ideal. The more ideal situation is that of the older vol regimen where we’d have spikes down and large VIX reactions that put as at break even and we just roll and work the market. If the market continued down even after the roll, we’d have not that much trouble even towards 25% from peak (very rare), I’d likely have to roll again and surely at this point the BS would have activated at some point. It’d take a few months but we’d recover but mark-to-market would have some swings.

So anyways, OK, not the nicest feeling but I was up about 30% for the year so it’s not terrible and this is the fun part since we can make most of our profits from rebounds on these types of falls as the majority of our premium and potential is closer to the insurance tent in the risk profile. Then I can convert it into a hedge and wait for more vol spikes

So now at this point, I realise that any pause or stoppage in the fear will bring a quick rebound in P/L and every week of market indecision (and no further crash) is closer and closer to expiration and less and the less Vega can affect (and the more theta converts to my profit). But I also realise that I have to start looking at heavy rolling and risk management because the vega and negative delta is getting steep. So on the first rebound, I add bearish STT (a mid way hedge) and I roll my closest STT as well as short ES. All of this is a cost but on some down moves, I start selling PCS to convert part of the bearish STT. All of this is a cost…but its largely offset by the fact that we’re in a juicy area of the original trade if we get some vol relief.
One week later I was down about 4% from a draw down in the fear spikes of 7-8% and then just days after that I was profitable on the Wednesday( fed meeting). IE my entire portfolio trade was up about 65k from Aug 1 which is great given the events that transpired. I’ve got a load of hedges still on that compliment the risk profile. The risk profile I posted includes all hedges (Except the Black swan hedge). Now yesterday was a slightly different story. We had a change in skew (the volatility portions of each strike changed) and I had a draw down to about -7k on the trade but does it worry me? NOT AT ALL. It’s a reaction to the fact that we have an important event on Friday (one being Powell speaking at 10am) and the fact that we didn’t have continuation in the up move. Skew and vol reactions w/ out market moves are generally temporary in relation to the specific structures I trade. So an area where I sold the insurance either went up or the area I bought went down. Pretty much it. But its all temporary. If we move up today, we get weekend theta and moving into next week is 4-5 more days of theta and less ability for vega and skew to affect. I predict I am back at the highs pending no big move by end of day today, I’ll post my graph either way to see.

Either way, now its a fun time of having the clock tick and getting further and further into our trade letting it mature. By sep 9 ish, my trade will have a matured risk profile that doesn’t mind more larger falls and starts to become more and more of a hedge profile as I massage out risk and take profits. My aim is to get it to about 250k before I go away. That’s sick. Yes, these trades mature every day and become not only more and more resilient but they also get massaged into hedges for newer trades that have a lot more time left.

Here’s the thing I realised, I tested just entering these trades on massive fear spikes (IE selling when the hurricane is barreling down). This happens a few times a year (probably 4-6x with Trump) and it eliminates most of the risk and has the same return as if you entered monthly (always on). You can do 15%-20% on capital and if you get a few a year, that’s 30%-40% with much less risk, draw down, stress, management and time in market.

So yeah, It’s a risk game where we syphon out the premiums on insurance.

The most common setup we use is known as a broken wing butterfly. Which is defined +1/-2/+1

Jun 12 – Update

Long ass 6 days of poker. I was able to finish 150th out of 8,809 in the WSOP (World Series of Poker) Millionaire maker. Pretty wild, 5 of 12 of us in the coaching group finished in the top 150 the other 4 were pro (coaches). Pretty wild result and testament to the studying. I am utterly exhausted. It’s been 12-14 hour days and there’s no chance I could play any more tournaments right now. I busted the 1k and marathon pretty quickly and entered a 1k in the Venetian which had a fantastic structure and though there was re-entry I think I made a few mistakes that was telling me I was fatigued.

Hand 1:

I’m CO, I open 56hh to 1600

BB raises 4,100 so I call given size

Flop AA7h

He bets 1/4th pot. I call

Turn 8h

He checks. I think to myself that he’s most likely missed and unlikely to have an ace given the sizings of his flop bet and he insta checks turn so I pot it (stupid) to fold out everything else in case I miss the million outs on the river. He jams…Ugh oh. Now I am forced to call w/ those million outs… I miss (no 9 or 4 or heart). I also thought I had much higher equity in the pot but I didn’t and I should have checked back and folded a missed river. Too high variance in a weaker tournament.

I should have checked behind and c/f on a miss. I forced myself into an all-in pot with a pot sized bet.

Hand 2: AA MP

I raise and BB calls

Flop is 873 rainbow

Check, I bet pot, he min click raises back to me. I jam for the remaining 25bb. My initial gut was that I was beat and I could make an exploitative fold but then thought that was nuts on a 783 board with AA. I’d mandatory call the min-raise and probably a small bet on the turn and fold rivers if he triple barrels. I wouldn’t normally jam here and it was a rec player so a min raise back is probably pretty strong. I call one all day long here against anyone else but def not jamming. Instead, I think that I can get max value out of all pockets lower than mine and any pair of 8s and jam. I am obv wrong and I end up with 30% equity against 78 two pair and missed. Way to borderline a spot to get it in. I doubt rec player min-clicks back like that with anything worse. Maybe a small pair but I block A8. He has all sets and two pairs. Meh.

Not a whole lot going on with the trades. The run-up makes things boring (though tonight it seems like we’ve had a bit of a market fall). Might make for some STT opportunities tomorrow.

I am stuck right at about 24% and I don’t have a whole lot of opportunity for big increases until I can get on more trades.

Jun 6 Trade and Travels update

My account is at 24% as of yesterday. A big increase and I removed all of my August trades throughout this week. I have September expiration which I’ll remove next week grossly above profit target but neutralized. October is also just above profit target so I may have to remove that next week as well. Normally, they’d be removed right away but the downside room is incredible and it’s got a profit tent built and my theta ratio to margin is still good. I am going to remove soon but I’ll give it another 7 days. Not much exposure now and locked in loads of profit. I have significant ability to take advantage of more vol if it does happen. Else, things can slow down again like it did in April. Profit comes in bunches during higher vol times. The majority of my potential profit came in the last 4-7 days so I doubt I’ll have the same trajectory through the remainder of this month. I’ll be happy to end around 25-26% for H1 2019. We had some vol but it came out on this gigantic move up from 2725 and that is the majority of my P/L increase. That 25% is on actual capital I have in total in my account. That’s pretty damn good. The thing that I am noticing is that since I put on STTs in every expiration on higher vol days, is that I end up with 4-5 expirations that the older ones act as medium hedges to the newer ones. In all of the vol we’ve had in the last 6 weeks, I’ve just been going up and up and up in P/L. If we had significant moves, they’d be fine because of the BSHs. All in all, I am loving how multiple expiration and maturity of STTs interact with each other.

I’ve been in a whirlwind of traveling since May 29th. I started off in Montreal which got a bit messy. I had some friends visit me and we brought our nanny so for a few nights things got a bit out of control especially given the fact one of our favourite bands was in town 🙂 Suffice to say it was a bit indulgent. A few days after that, I got to play a few poker tournaments there which went well in terms of applying the recent coaching etc but just didn’t have the luck deeper in. Next up is WSOP Millionaire maker tomorrow.

After MTL, I headed to Ottawa to do a whole slew of meetings for my software licensing business. Those ran long but we hashed out our future pathways. It was very productive and everyone got on the same page after hours of board room meetings. I have the best partners you can ask for and given we’ve been in business since 2004, we’ve never in all that time not ended up on the same page after a face to face nor have we ever had emotional disputes. I guess we’re all lucky, as I have heard other companies can have nightmare situations. I am fortunate to have good partners.

I ended up quite tired after the week of partying and heavy meetings. We stayed at this awesome airbnb house on the Gatineau river where I tried to recoup for the next leg.

After Ottawa, we met with a private educator in Toronto to see if we get along. We’re using next year as a year to get our kids top notch and ready for the real world and ready to apply for competitive private schools. They’re currently in Montessori and its just not cutting it. My daughter doesn’t thrive in a Montessori environment. Long story short. Lemons making lemonade, use the year to travel w/ a private educator and use the year as an opportunity. Soon come, the kids will be older and it won’t be possible to travel.

Then my wife and I departed Toronto sans kids while the kids left w/ her sister to Cayman. We upgraded our flights and flew to Denver and spent two days there. Awesome town but def some sketchy areas. We had to call the police because a guy was dying in the middle of the road (this would be the second death we seen on this trip face to face……) Horrible to see. We had some pre-wedding parties to attend and ended up having a pretty good time. We rented a car and drove 5 hours to Moab for a glamping wedding. Was awesome but again my liver is suffering a bit. We ended up sky diving which was the highlight of the trip.

After that we drove to Las Vegas for a night and unfortunately saw ANOTHER dead person on the side of the road….we checked the news after and they’re still investigating it as a potential homicide. Horrible thing to see, still see it in my head. Was very close to where we were (right on side) saw it clear as day. Death is apparently following us….

We spent a night in LV and had an awesome dinner and got an epic suite. It took about 6 hours to get there from Moab. We left at 8 and arrived around 2pm. We were just stopping through on our way to LA for our final leg together (which ends today).

In LA, the first night we went to the Laugh Factory and were so luck to have stumbled upon one of those surprise unlisted guests (George Wallace) who free styled and actually crushed it. Was one of the best experiences I’ve had re comedy. Super lucky. We were right up front too. The following night we decided to go and spend time in the room where comedy goes to die (The Belly Room) and again had an awesome time. We’re staying near Santa Monica Blvd in the gay district and it’s coming up on the 50th anniversary parade so it’s high action. I get loads of compliments while walking with my wife. Love it lol. The wife leaves tomorrow early for Cayman and I stay for 4 days to play a few WSOP events (I’ll drive to Vegas from LA tomorrow). I miss the kids way to much though now as it’s been 7 days so I’ll be looking to book an earlier flight on any bust out. But I’ll be back with the family Jul 1 for the main event.