Re: How does it feel...
Yes, If you're not willing to put up more money into your bankroll you stand a very good chance to lose it all. Just use the 300BB rule and you won't go wrong. However, if you find that you're learning and beating the game after a lot of hands (at a minimum of 10k) and you have extra money I would think you could move up quicker but always make sure you have that 300BB in your bankroll. Also, if the players are not really serious they should be easy to beat.
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