In the winter of 1929, a trader named Jesse Livermore made the equivalent of $100 million… while nearly every other investor on the planet was being wiped out.
And unlike the other winners of the great crash… he didn't benefit from any insider information…
Because Livermore understood something that most investors spend their entire lives ignoring…
The market is not a flat, even surface where every day offers the same odds.
Some periods are fertile ground… whereas others are a minefield.
And the calendar, he believed, was part of the map.
You see, most people view the market through the lens of Ben Graham’s Mr. Market analogy…
A chaotic collection of buyers and sellers yelling prices that they can never agree upon… and so there’s always a somewhat level playing field.
And on a day-by-day basis that’s true…
But it does ignore one crucial element…
Because when you zoom out far enough (I’m talking across decades of data) you start to notice that certain opportunities don't arrive evenly throughout the year.
Instead they cluster…
Certain sectors come alive in certain months…
And certain stocks have historically been far more likely to rise in specific windows than in others…
I call these moves Money Windows… because they are only open for a certain amount of time before they slam shut
Livermore wasn’t the only person to use these…
Because Stanley Druckenmiller said something similar in a recent interview.
Druckenmiller is arguably the greatest macro investor who ever lived… he ran George Soros's Quantum Fund and reportedly never had a losing year across more than 25 years of managing money.
But when asked about his edge, he didn't talk about stock-picking.
Instead he talked about recognising when conditions had shifted in his favour, and then pressing hard when they had.
His argument was that most investors spread their bets evenly across time as if every week offers the same odds.
But they don't.
The market has stretches where everything fights against you, and stretches where the wind is at your back.
The skill is knowing which is which.
Most investors do the opposite.
They react to headlines and end up sitting paralysed through the noise until something moves so dramatically that it finally feels safe to act… by which point a big portion of the move is already in the rearview mirror.
So while the market has a calendar, most investors never learn to read it.
Which is exactly what we're going to change on June 25th.
I’m hosting a free training on these Money Windows… where we'll walk you through the specific, recurring periods where historical data shows the odds of a good outcome in a given trade.
Some of these last a few weeks, others a few months…
And we’ll focus on the ones that have shown up consistently enough to pay attention to.
So if you've ever felt like you were always one step behind the market, this training was built for you.
Oliver
P.S.
Tomorrow I’ll walk through an example of a repetable Money Window on a stock that you all know