Yes, there are plenty of people who pull themselves out of poverty. Unfortunately, they are the exception, not the rule. Paul Ryan is absolutely right. When people are in prison, recidivism rates are high. When people grow up with poor education standards, the societal gaps will continue. The bootstraps mentality is a farce and more needs to be done. Unfortunately, while Paul Ryan is good at identifying the issues, he is not good at solving them. He is part of a political party that continues broken policies of self determination that don't work.
There are certain types of behaviors, certain types of people, and certain types of exposure to different economic class systems. While there are stories of hard-working entrepreneurs who make it big, the odds are still extremely high against success. If a person can do as well as their parents did, they are a step ahead already.
1) This is capitalism...The opportunity to achieve any desired lifestyle state (or standard of living) exists; your 'poor-ness' is nothing more than a make-up of your lack of efforts, motivation, competitiveness, and education (heck, there are thousands of stupid people swimming in money...Find your niche).
2) See lots of immigrants start off in the U.S. dirt poor, and within a few generations, they become exceedingly rich. Stop whining, start trying. 'Your' life may suck, but your offspring should be better off than you...Key word..."should".
3) What is 'poor' and what defines it? This is a very relative term. The U.S. poor could live like kings in 3rd world countries. In the U.S., your 'poor' status is relative to the average or in comparison to others. Point being, f***ing stop comparing yourself to everyone else and set out to achieve the standard of living you want. If you think your standard of living constitutes 'poor'...Then f***ing go do something about it...Change it.
By stating that, I do not believe Paul Ryan meant that there is no hope for poor people. I think he said that as a criticism to the world system we live in, where the rich is likely to get richer, whereas the poor is likely to remain that way.
Paul Ryan's statement is a generalization as indicated in his use of the word "likely." The population has hope because it is made up of individuals. If individual people aspire to greater wealth that their previous generation, they are likely to break the cycle of poverty and have more wealth than their parents.