I love these kind of books, some recommendations:

Tech-specific (more like Careless People):

- Empire of AI: tells the story of how the massive AI labs started and became as big as they are with a focus on OpenAI, provides new insight into the coup that outed Altman a couple years ago

- Number Go Up: digs into the crypto culture and scams with novel insight into Tether

- Bad Blood: a classic about Theranos and Elizabeth Holmes and how far a technologically impossible startup can go

- Super Pumped: about Uber and the dirty tactics they employed to stay ahead, also touches on the toxic culture that was propagated there

- Money Men: about the criminal enterprise around Wirecard, hard to keep up with at times due to the focus on the FT investigation rather than the fraud but interesting anyway

Finance-focused:

- Barbarians at the Gate: a classic about the attempted takeover of RJR Nabisco (oreos and tobacco) by management and early PE firms, told from first hand accounts

- Too Big Too Fail: similar in form to Barbarians but instead focused on the 08 collapse and the attempts by the government to save all the irresponsible banks, told in too much of a sympathetic way for me but interesting to see how things happened behind the scenes

- All the Devils Are Here: on the other hand a very unsympathetic look into the 08 crisis, by the same authors as Smartest Guys in the Room

Other:

- The Smartest Guys in the Room: my favourite of them all, tells the story of Enron and their rise and incredible fall, basically a foundational text on how to do a financial crime (and not get away with it)

- Chip War: very relevant look into the production of computer chips, highlights the reliance on only a few companies and the incredible costs involved

- Empire of Pain: also a favourite, goes into the Sackler family and how they built Perdue Pharma and then proceeded to cause the devastating opioid epidemic

- The Power Broker: a classic about Robert Moses who basically built half of New York at the expense of marginalised residents, it's very long so I'd recommend reading/listening along with the 99% invisible breakdown

I've not read Character Limit so have added that to my "To Read" pile!