* Being wrong-footed in market view (and basically net short throughout most of the period) I had to find a way to deliver positive investment returns…
I wanted to revisit and expand on my comments yesterday on why I actively trade the indices… on almost a daily basis (sometimes multiple times a day!).
Most of my observations below are self explanatory. I am transparent in these trades because we have a body of subscribers that trade actively, many trade in non-taxable accounts (foundations, IRAs, pension plans, offshore, etc.), some employ tax-deferral strategies (to offset short-term trading gains) and for other reasons.
To me, I want to capture investment returns always. As I mentioned, to state the obvious, the best positioning would have been to be bullish over the last 2 1/2 years and to buy and hold a portfolio of large-cap tech.
But I held to a view, take ownership — as we can’t rewrite history.
Unlike many, I admit to being wrong (often) and I am always in doubt.
When I have been predominantly wrong (except when I went long briefly — for a few weeks — in three selloffs), as I have been since early 2024, and I am positioned modestly short, I need a strategy to return profits to my investors.
I do so by trading the indices, in particular, actively.
There has ben almost 29 months since January 2024. Despite being positioned wrong-footed, some excellent individual long-term investment shorts and my short-term trading (in the indices) resulted in profitable returns in 28/29 monthly reporting periods — with the only drawdown of -0.22% in the down month.
If you like, put that in ChatGPT and figure out the odds of returning profitable investment returns (being positioned net short throughout most of the period). It leads to an interesting outcome.
More Comments About Short-Term Trading
From the Comments Section:
Dougie Kass
On the issue of short term trading…
The other point I want to share is that our subs come in all stripes, temperments and objectives. No individual sub is alike as timeframes and risk profiles and appetites are all different.
Contributors, like myself, serve all of our subs.
To state the obvious, it is preferable to call the market right. I have not over the last three years – in which a buy and hold strategy was ideal (in hindsight) and preferable, incurring no tax liability.
That is elementary and tautological.
So being wrong I have tried (and succeeded) in taking a trading approach to engineer profits while being wrong on market direction.
We do have many subs that are buy and hold oriented- but based on my interaction, that is likely for only a portion of their portfolios. It seems they nearly all trade outside of their long term investments.
Among the things they miss is that there are a large amount of subs who have non taxable accounts (IRA, pension plans,etc.) and there are foundations, etc. that are not directed by tax consequences. Many of us manage other people’s money. In my hedge fund, the majority of my investors are not taxable. Those subs who are critical fail to understand this. Additionally there are tax avoidance strategies that can offset short term gains.
As I stated in today’s comments (and all week), there are a number of subs who are griping and growing impatient with cannabis stocks’ underperformance. They are unwilling to hold (and accumulate) weak sectors, yet seem to have long term horizons.
So, everyone is different.
We also have a large portion of our sub base that are trading oriented. And if we look at the proliferation of leveraged ETFs and ODTE options that have an investment timeframe of less than 24 hours – that is a large and rapidly growing population of general interest by parties in short term trading.
Finally, as I have stated repeatedly in the past I created a Best Ideas List that has had longs (and shorts) on for many years. I have said repeatedly that if you dont agree with my negative views onthe market it is a good menu to select longer term investments.
Position: None
BY Doug Kass · Jun 17, 2026, 2:10 PM EDT