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I never told my son about my $120,000 monthly income; when his wealthy girlfriend’s family invited me to their exclusive country club, I pretended to be poor—just to test their character; they looked down on me and had no idea I was the investor who controlled their future.

I stood in my small one-bedroom apartment in South Boston, looking at the worn leather jacket hanging in my closet. Next to it, pushed to the far corner, was a…