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.

Risk taking and pulling the trigger

    Risk taking and Pulling the trigger

Let me preface this with a funny but true story:

In my twenties, I took a big risk, I invested all my net worth and even my future income into a software business idea. So essentially, more than I had. It was a huge risk. It took 16 months to get the software idea from scratch to launch-able. We of course blew past deadlines as is typical, and went over-budget. I had no money left though I had some on its way. I was at a pop machine with a friend and business partner (he’s probably reading this and laughing) but I had one single looney left and I told him, this is my last looney and I’m buying a diet coke with it. I went to put into a pop machine. Guess what? The pop machine stole my very last looney to my name. Sounds super cliche but it’s an actual true but hilarious story. The pop machine ate my last looney. The end of the story is positive, the business worked out fantastically and all is well. But I took a leap and risked it all except one looney which a pop machine stole.

I am part of a chat group (Index Trading Group) which I started back many months ago and has now well out grown me. It is now some 250 people. 250 very smart and ambitious people. It’s grown to a point I never believed possible, I rarely contribute on there though my intentions were good but life, busyness and trading gets in the way as it often does. It’s no excuse. I should contribute more. Anyways, this options community is, in my opinion, immensely changing and shaping the future of retail complex option trading with new brilliant research and ideas. It’s got to be at the forefront of market neutral options trading. I often am even somewhat intimidated and in awe of some of the members abilities to focus and create great back-tested ideas and videos (I think most of those reading this will know who they are). Perhaps, it’s why I rarely contribute, it would take a lot of resource to match the quality they put out. I trade huge accounts which takes up time, I have a business to run and I have a family to take care of. Again, no excuse, so do they. But those become excuses I use to put off doing or coming up with ways to contribute (human nature). Anyways…

Today a topic came up about risk taking and trading for a living. A member asked what it would take to quite your job and trade for a living (the dream eh?). I say that almost facetiously, I trade as if it was for a living probably, and it’s got its perks but it’s also very hard money. I think business can be much easier 🙂 The breakdown from one member was very succinct he had listed out exactly what was required to adequately trade for a living and it was in the ball-park of 5MM which assumed you’d only trade 20% of your net worth and that you had several years put away for reserve. I’d pretty much agree with that except there-in lies the rub. If you used that equation to assess risk taking, you’d probably never make it to 5MM. Whatever gets you to 5MM in net, is likely to have broken that equation. Sometimes, you have to break the usual conservative views on risk taking and make that leap. Now, I don’t know if you should do that with trading per say. If you do do that with trading, you better have done your damn homework and have had a long stretch of success!

In life, and if you want to become successful and rich, you just have to jump and pull that trigger. BUT. You have to give it your all and you have to make sure you have back-ups and fail safes built in. Take the risk but if your fucking taking that risk, if something happens, you don’t sleep if it requires attention, you work your ass off making sure the risk you take works or that you have back-ups and ways to mitigate failure. When I started my business, I put every single cent into it, very irresponsible and would have seemed crazy. It worked out well but I think it was more because of insane persistence, fail-safes and tenacity. Once I made the decision to pursue an idea re software, I did everything I could to make it succeed. It took 7 years before it was profitable, and I worked 14 hrs a day 7 days a week to make it work (in my twenties). I pulled the trigger and being smarter now, I doubt I could ever make the same jump again, it’s just so crazy! But back then, once I had pulled the trigger, it was game on, I had back-ups to make it work and I worked 14 hr days 7 days a week making it work. I gave it my all.

The thing is, trading is so psychological and it’s essentially built on irrationality and the medium/arena (market) is largely unpredictable (some TA’s are screaming right now). I don’t think I’d pull a trigger in trading for a living if I were back in my twenties and about to take a risk.

For instance, on the macro level, trading for a living can largely be successful with all of the points I mentioned above (tenacity, hard work, dedication and backups). So Sure, I agree with that, hard work, tenacity and dedication will eventually lead to success as a trader on a macro level. But it’s not the same as a business..it’s a different beast. It’s a psychological Beast. You make decisions that directly and quickly cost or make you money. Dealing with the repercussions of those decisions whilst in a challenging time (down turn in P/L, stressed about $, needing to make more) etc will wear on you. I’ve made borderline adjustments that have cost me a car. Those adjustments bother me and used to affect my life. If you start second guessing yourself…it will start to affect your well-being. I lost many days of my early trading career life dealing with these frustrations and stress. I wasn’t even trading for a living, it was more of a hobby and the amounts weren’t touching my net worth. I can’t even imagine what it’d be like to trade while requiring it for living. I don’t know if I would wish it on my worst enemy. It can’t be easy. I commend the pro full time retail traders. They are a strong breed. Unfortunately, all of these little unexpected psychological issues of trading are human nature and WILL occur. It’s like running bad in poker, some players never recover, it’s a high speed venture with instant requirements for decisions that can cost you dearly. That will wear you out. This is why the best traders have very strict plans that they adhere to religiously. You cannot have on the fly decisions affecting your well-being or your trading psychology. This leads me to the micro level..

If you get into trading for a living and you run bad, this negativity will seep into your trades and it’s not something you can hit the pavement and make work with tenacity since its so much more complex of a battle (I am mostly talking about the internal battle within yourself at challenging times in trading and with the whole basis of the market being irrational and unpredictable). If a trade doesn’t go your way, and it’s getting desperate, there’s not much you can do and it’ll lead to more risk taking. So the whole internal battle you have psychologically, will tend to burn out or cause failure within someone. You can’t just get motivated late at night as a trader, and make something work instantly. So many times, I’ve thought my way through a problem in business, often times that’s not really possible in trading. That in and of itself, will lead to feeling helpless if you experience a bad run. This helplessness will compound. Then comes along second guessing yourself, and generally putting yourself in a compromised mental position.

With a business, usually, you can solve it with smarts, tenacity, dedication and time. You can, not always, but mostly, make it work! You can work hard enough to get lucky. You can do that on a large macro level with trading in general but not on a micro level which can be devastating to the psychology of the trader. I wouldn’t wish trading for a living on my worst enemy if not properly prepared, well bank-rolled and experienced.