As someone who spent the past year in school searching for a way into the social entrepreneurship space, I agree that there are many challenges to breaking into the field. As a summer associate at the Acumen Fund, I know that it is a priority for us to develop avenues for young talent to enter the space. One way we are exploring that is through our Young Leaders Workshop (http://blog.acumenfund.org/2009/06/03/acumen-hosts-first-student-leaders-workshop-for-undergraduates/) and we are hoping to build upon this very successful experience.
Also, as a white American male currently pursuing an MBA, I find myself in the minority at Acumen even though I think everyone here could say the same given the gender, geographic, educational and ethnic diversity.
I believe that one big problem is the amount of opportunities currently available within organizations like Acumen and Kiva (main offices with under 40 people). One way to solve this is to build pipelines for talent directly into social ventures themselves who are desperately looking for talent and skills out in the field. Usually, this will mean people who already have skills and experience in the working world and are willing to take pay cuts. Developing a system that facilitates this and supports this transition is key. However, the need for experienced talent in this area only adds to the chicken/egg dilemma.
As an organization, we are always listening to hear what people have to say about this. Please feel free to write me at bmurray@acumenfund.org if you have any suggestions about how we can improve.