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How's he being an ally here? He's just talking about some people who supposedly pulled themselves up by the bootstraps. Most likely in an attempt to prove that others in similar situations have only themselves to blame for not doing the same.
I misread it as people who graduated Havard Law School who are now homeless.
I probably should have emphasized the "people who are single mothers" part more. I'm sure he would criticize this kind of inclusive language if someone else used it.
Sure is a reach but I got a small inside my head but not actually physical exhalation of air