Troubled: A Conversation with Rob Henderson & Dr. Drew Pinsky

You can now watch my recent conversation with Dr. Drew. This was a live event we did with the Manhattan Institute to celebrate the launch of the paperback edition of Troubled: A Memoir of Foster Care, Family, and Social Class.

Enjoy:

Some topics we covered:

• I opened up about the surreal experience of sharing a stage with Dr. Drew—someone I grew up listening to on Loveline

• The divide between kids growing up in stable, affluent homes and kids like me who were latchkey by necessity—and how that plays out generationally and across class lines

• Dr. Drew brought his addiction and trauma expertise to explain why cycles of dysfunction repeat, and why it's so hard to break them

• The strange cultural gap between elite universities and working-class communities, and why higher ed often fails the very people it claims to help

• Dr. Drew and I discussed how giving people money doesn't magically fix chaos; without stability, guidance, or skills, windfalls just accelerate collapse

• The surreal transition from foster homes to the military to the Ivy League—and how bizarre it was to hear students from wealthy families call me "privileged" because I didn’t share their worldview

• The psychology behind luxury beliefs—and how affluent people adopt trendy, often harmful ideas to gain social status while insulating themselves from the fallout

• I asked Dr. Drew what he’s noticed after decades of speaking with young people, and he described a generational shift: less curiosity, more fragility, and increased hostility toward authority figures

• The irony of American elites embracing European postmodern philosophy while French academics have moved on from it and now think it’s nonsense

• I answer a question about whether I’d send my future kid to an elite college