I won the $1000 guarantee on Betonusa.com three years about, won $150ish and never looked back.
Although this was also during the time of casino whoring and other profitable adventures that built my BR. Without the infusion of the casino money I would have had to deposit several times.
The key is to manage your BR when you do deposit. If you deposit $50, $500 or $5000 if you play at limits higher then your ability or BR then you will no doubt go broke trying to learn to play at that level.
I would suggest a couple of things:
1. When you do decide to deposit, try to get the maximum from the deposit bonus. This is pretty much free cash, this helps if you are a break even or below even player. It keeps you making some money while you are learning the game.
2. Start at low limits and then work your way up. You will find that each level requires a slightly different ability/skill to succeed. In this way it is similar to an adventure video game, where the first level is a tutorial (play money/freerolls) teaching you how to play the game, the next level is a tutorial but without the help guide ($1 tourneys and micro-limits), the next level teaches you how to die, but the next time you spawn in you kick the level butt because you figured out how to beat the obstacles keeping you from passing the level ($1-$20 touneys, and up to $5/10 limit, $1-2 NL.) The rest of the levels you can only beat if you find the skill and ability (higher stakes).
3. Buy poker tracker/game time plus (or other paid software) and use it. This software taught me where my holes were, but before that the onscreen display showed me what players were tight and which ones were week allowing me to control my play against them.
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