My dad was a dyed-in-the-wool leftist as a young man but is now a pretty tepid progressive (voted for Bernie, donates to Dems) who fully believes capitalism is the best system and it just needs some tweaks. His changes in beliefs also corresponded to a change in class—shocking, I know.

He's always recommending me books which I usually don't read because they're not my cup of tea, but I figured this would be a great opportunity to do one of these book swaps I've heard tell of ("I'll read this if you read that"). Problem is, I am a dummy who mostly just listens to podcasts, so I need some help picking a book for me to read first and then have him read. My first thought Anand Giridharadas' Winners Take All (one of the few relevant books I have read) since it squarely takes aim at the idea that the wealthy/corporations can be a force for good while shoring up existing structures (my dad's a big-time Bill Gates believer), but I wonder if there's something even better out there that takes a more systemic approach. That being said, I think one of the strengths of that book for is that it doesn't assume (all) of the philanthropy is purely cynical and instead focuses on the allure of philanthropy and why it doesn't work, which is a lot more palatable for a lib who also believes in those things and doesn't want to feel like a sucker.

Besides the inability of philanthropy/"conscious" capitalism to address the problems of the world, I think urbanism and imperialism (in particular US imperialism) are also topics he might be receptive on. With the former he's bought into tech-will-save-us copium without questioning it much and with the latter I think he's a combination of in denial and just genuinely uninformed, so I think he can be moved on them. I read most of Shock Doctrine but I honestly didn't find it very convincing; I didn't really need to be convinced, but I didn't get the impression it would convince many fence-sitters of its central thesis. I'm sure there are plenty of other great books which give an overview of imperialist crimes and their motivations, though.

TL;DR: looking for accessible (audio)books for an older lapsed leftist to read. Promising topics include the failure of philanthropy and social enterprise, urbanism, and US imperialism, but I'm open to others

EDIT (9/20): Just want to say I appreciate everyone's thoughtful recommendations! I'm listening to The Jakarta Method right now (excellent stuff) and will work my way through your other suggestions soon. If I remember, I'll post an update about how things went!