Standard deviation is defined as the square root of the variance. What does this mean? Well, basically, it's a measure of the spread of a set of numbers. So, for instance, if you take an average of your wins and losses, the SD is an estimator of how wide your swings are, in either direction. How is this different from variance? Well, it's because SD is actually used to describe the "spread" in the context of a
normal distribution - which is your famous Bell Curve. Unfortunately, I can't draw a picture of a bell curve on BTP, but I've provided some links below, in case you're not familiar with this concept. If you can picture a bell curve, the mean of the distribution (or the average) is the point that reflects the middle. Another way of thinking of this is that it is a reflection of an event that is most likely to occur. Back to poker - this means that if you are winning, on average, +$5, then it is the mean, or the "center" of a distribution of your wins and losses. It means that you are most likely to end up +$5 in any given session. The standard deviation, on the other hand, tells you how
far away you have to move from the center before you hit a less-likely event. For instance, if your SD is $20, it means that whenever you have a winning session that is $25, you are actually +1 SD out from the mean, which corresponds to (in a perfect normal distribution) an event (in this case, winning an extra $20) that is one-third as likely to happen as an event at the mean. Accordingly, it means you have an equal probability (which is one-third less likely to occur than the "average" case of winning $5) of moving -1 SD away from the mean, which translates to a net loss of $20.
So what does all this mean? It really just goes back to the idea of how volatile your style of play is. I'm not sure if this is entirely an accurate statement, but you might consider it one measure of how loose-aggressive your play is. (If anyone else as a better concept of how it directly relates to poker, feel free to clarify/correct me

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Hopefully this makes some sense to you. Now, let me address your other question about why it's sometimes expressed in $s and sometimes in BB/100 - this is quite simple. Ultimately, it doesn't matter *what* units you use for calculating your SD - it is merely an expression of the "spread" of a set of numbers, right? So if all of your numbers are in terms of BB/100, then it's an expression of your spread in terms of BB/100. If, on the other hand, if your 'numbers' (wins/losses) are measured in $s, then your SD reflects your volatility in actual dollars.
Now since PT calculates means and SDs in terms of straight dollars, BB/100, *and* BB/Hr, I find that looking at SD in terms of pure dollars is what's of most interest to me, since all I am really concerned about is my true win rate in terms of dollars. This is important to me, because I can use the SD (in dollars) as well as my current bankroll (in dollars) to calculate my current risk-of-ruin, to see if my true win-rate justifies the level of play in which I am involved. I've found that since PT is perfectly happy calculating a weighted mean for your win rate and, correspondingly, your SD, these stats in terms of dollars are significantly more useful in determining what my BR *should* be based on the risk-of-ruin I'm willing to accept.
Am I off base here, guys?
Here's some links to articles about SD:
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