In the systematic world, pyramiding can come from multiple systems firing on the same market. E.g. you may have an old Trend position that pulled back (keep stops wide), then you get a reversion entry.. then maybe something else eg Term Structure, Seasonality, Skew, COT, Fundamentals etc.
The position gets bigger, looks riskier, but it has a higher expectancy for all of those trades to win even individually because of all the other signals agreeing. That makes it worth the risk of being concentrated.
On a Sharpe ratio basis I haven't been able to make pyramiding with a single trend system look better (i.e. stronger signal + more time = add to position). But adding due to different uncorrelated signals does increase Sharpe and other metrics too. Some metrics can be improved (eg total profit per trade), especially pyramiding into stuff like mean reversion.. but have to be careful not to become a martingale trader.
E.g. my Rubber position is nowhere near my best trend, but it did enough different things in the lifecycle of the full trade to allow heavy sizing (I'm on the hook for a silly number of metric tonnes of rubber). So it's now in the top 5 profitable markets purely because it became a concentrated bet.
I think a real point people are missing with pyramiding is the fact that the best trades usually go without offering much of an entry, either you are in or often missing.
Furthermore the best trades don’t have one leg but often 3-5, they don’t just pop and die.
Pyramiding builds upon that understanding to exponentially size into an idea that presents those top odds.
It maximizes the overall expectancy of the trade and the linked low variance/volatility along the path of those best opportunities. Measured as total expected return vs volatility to achieve the target.
It maximizes the certainty about winrate at the cost of the buffer by using tight structural builds along the path and by maintaining a strong average set by the original anchor.
A balance between win rate off of the average, using the buffer, RR along the path both on the overall trade and the singular adds along the path that combine into one bigger trade.
The overall cost is win rate in the end, but one that lowers it marginally vs the gains it generates on the winners.
All in all the idea being being big on the best ideas with the most anticipated alpha rather than missing, too small and having little chance to pay for mistakes.
Trading is a game of breakeven for 80% of trades with 15% paying bills and perhaps 1-5% actually creating the Wizards… Make sure to find a way to create the hockey stick chart.