Do you remember ..
That Whitney Houston song called, 'Step by Step'?
That's how you do it, step by step.
I, internally, think that my time and my skill is worth $100 an hour.
So, if I play a $100 9 ball match, race to 7, I am in keeping with
myself. Granted, I may not win every set, but I am at least playing
at the level I should play at. If I play for more, that is okay. If I
play for less, then I am low balling, trying to roll up my money.
You have to get comfortable playing for $200-400 sets, then up to $5-600
sets. From $6-700 a set, you can make the jump to $1,000 a set.
But, when I play for larger money, I usually stipulate that each player
(myself included) has to guarantee 3 sets worth of money, and no
winning the first set and running with the money. That way I know
the minimum I can win, and that we will be playing more than 1 set.
When you play for larger money, you are very specific about what is
required from each player, and get it agreed on before you start playing.
Also, any $500 and up a set money is usually held by an agreed upon
3rd party till the set is over , someone you both trust without a doubt.
If you know the guy, and he has shown you money and you trust him,
then go ahead and play. As a rule though, any sets over a $100, the
money should be posted, and kept where it is safe (like on top of the
light, but don't go to the bathroom without a trusted friend keeping an
eye on it for you).
If you are in a strange billiard room for you, take no chances at all
with your money, make sure it is safe at all times. Instead of posting
sometimes, players may elect to show the other player the money for
the upcoming set, and then just keep it in their pocket till the set is
over, but even then an opponent might just try to skip out on you
out the door without paying you (I had that happen to me on a $400 set).