> toeing the line
I'm not sure that phrase means what you intended to say here. From Wikipedia, [1]: "Toe the line" is an idiomatic expression meaning either to conform to a rule or standard, or to stand in formation along a line.
Guess I learned something new today. I've always thought "toe the line" means something closer to "staying as close as you can to the line without crossing it", if that makes sense.
It's probably common enough to be an accepted meaning nowadays, like what's happened with "beg the question". I think the original meaning also lends itself very well to people believing the phrase is "tow the line" since that makes some sense with conforming to a rule. Who knows, idioms are a moving target.
In certain cases you can use information asymmetry to your advantage. You know something they don't. A good example is any market dependent on public opinion surveys (eg political polling). That data can be hard to find. If you can find it faster than everybody else then you win more often. There is still some chance involved but it's more like poker than blackjack (not a great analogy but you get my drift).
People did this in sports gambling since forever. Professional gamblers would cultivate a source (like a coach) to get inside information to get a leg up. That said - you are still placing a bet based on the best information you have. It's gambling, or else, what other word is for it? Investing?