I started with nothing and am proud to be able to say that I never deposited anything on a poker site
, and while I have a modest bankroll by a lot of people's standards I now have plenty to play in the tournaments and levels I like. And I have taken money out from time to time, it's quite a feeling - even though tiny compared to my paychecks at my job, it's somehow ... sweeter (and as a practical matter very helpful this past Christmas: we have 3 daughters 11 to 17 and they are getting expensive).
However, after saying all that, I'm not sure I would want to go back and do it all over again. I think the first time I placed in the money in a freeroll was something like 60 cents; needless to say it took a LONG time from that first freeroll, a lot of patience and bankroll management. Sunday night I made my largest tournament winning - $560 - modest to many, but a heck of a long way from that first 60 cents. I love poker and would do it if I had to, but I'd rather not start all over. Why not compromise and take some of your money out, but leave enough that you're not fighting it out in those ugly freerolls where you might play for hours and come out with ... 60 cents ?