Apr 28 2021 – 15.5% Quarter and a 43% year

Been pretty absent from posting which has obviously become a habit. I’ve been all over the place the last 3 months and I think the lack of routine affects my ability to get posting which is contrary to the blogs intent especially with the travel portion. I just get caught up in new experiences and get behind in other aspects and my life becomes a time-balancing act but a well balanced one in regards to life and work balance.

We had flew into the US in October of 2020 to begin flight training and take possession of our plane. Exciting in and of itself, but probably a bit irresponsible given the pandemic was full blown at the time but we were committed with our long term renters in Cayman coming in at the same time. Cayman had no local transmission (and it was totally normal life there) so it was a pretty iffy decision, is what it is. We had expected to finish up the PPL there before Christmas but weather and thanksgiving instructor schedules got in the way and we weren’t able to finish so we left Dec 9th to get the quarantine over with before Christmas holidays.. As fate would have it, that didn’t matter, Canada went into full lockdown during the holidays

It was pretty exciting though because we took possession of our new home which has such an epic design and quality. Karin Bohn helped with the interior design, and subsequently the project got all over her YouTube channel which was pretty cool and my good friend Chris designed and helped build it. He put his heart and soul into it and it shows. I don’t think I could ever sell it. We had started planning the house back in 2016 as we’d planned on staying in Cayman and having a great home base in Caledon, Ontario which was near all our families but plans had changed with respect to where we’d school our children and LA became the choice. We’ve rented our house in Cayman and now will just go back and forth between Canada and LA. Anyways, we stayed there till about March when we went back to LA (with the intent of staying 2 weeks) to start searching for our primary home (we found an awesome house/project in Hidden Hills), but opportunities arose to finish the PPL in Knoxville, Cirrus went and picked up my plane and I flew to Knoxville to train. I ended up staying behind and trying to finish up that pesky PPL while Ash went back with the kids to Canada. I finally solo’d and made a ton of headway towards the license. We’ve done the training pretty unorthodox as we’ve used the plane several times for utility trips (picking up au pairs, family, flying to various places for $100 hamburgers etc). So I’ve gained experience in so many different ways. Here’s some photos of the training and solo.

While in Knoxville, I got the vaccine (Pfizer) and worked hard on the PPL which went really well. Had some incredible experiences. I flew with my instructor to pick up the family in Canada. The original intent was to go back in April but the pandemic in Canada got so bad that it just wasn’t worth staying. So we grabbed them, whisked them away from the never-ending lockdowns and explosion in COVID cases and brought them to Knoxville for a week. Here’s some photos of the Canada pick-up, the dogs were excited to see me (oh that was another new thing this quarter, we got them in January, I was afraid they’d forgotten about me but from Teddy’s reaction here, it was clearly not the case.

We stayed in Pigeonforge and I got to fly back and forth to Knoxville for training and finally solo’d and was about 10 days away from check ride, but we had closed on the house in Hidden Hills so we went there for a few weeks (here now). Another cool experience, I got to fly the dogs and cat to LA from Knoxville. Wild. Here’s some pics from the super long cross country from Knoxville to LA

Teddy in the back, chilling.

We’re in LA now until about June (assuming Canada gets better). Then we’ll be back in September full time. Whirl wind of a life lately. Looking forward to settling down where I am just making my way back and forth between the two houses. But have to say, I’m loving this neighbourhood and the general area. The kids are live in school (finally) and we’re looking forward to the big life change from the Caribbean to western civilisation.

Here’s a few photos of the new neighbourhood plus a cool sketch/art of the project.

Isla rocking her new bike
Putting up a TV. Getting innit.

Despite all this wildness in life, the quarter was great, doing 15.78%. Finally moved towards non-discretionary trades and by March, was fully allocated. Throughout the quarter I furthered some research efforts into ‘meta-portfolio’ construction and the movement toward a more time and skew-diversified approach with respect to my individual trades. The sum of these individual trade types within the total portfolio of trades allows for a smoothing of variance which allows for better compounding of returns over time. I’m thinking long term, and I am approaching my portfolio of trades with wealth conservation and low-risk growth as the primary objectives. The result and implementation of lowered volatility by way of diversification will yield a better compounding of returns over the course of years. I am lowering the volatility tax, and in turn raising the profitability of the portfolio of trades. In my opinion, compounding via the reduction of portfolio variance is the true secret to beating the markets.  A high volatility portfolio that averages 15% per year could underperform a very low volatility portfolio that averages 10% a year over the course of a few years. Taking this concept and applying it to the portfolio of trades is the focus and part of the edge.

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.