The Private Equity Wager: Heads We Win, Tails You Lose

Once, when I was fresh out of college, I worked at a mortgage company, a really rotten place. All day I looked at loans, applied some rules, issued a thumbs up or thumbs down. Some couple in Honululu Hawaii with x income trying to get an n amount mortgage. Denied. Approve. Denied … all day every day, people reduced to just a set of facts, and I, a faceless “underwriter” in some far off corner of the country have final say over whether or not they get the house they want, that they might dream of. It’s dehumanizing.

Before I jumped to tech, I took one more shot at credit underwriting, and interviewed at a company in New York City that did something called “factoring”. On paper, it seemed like an ethical, maybe even highly beneficial application of finance. You buy a company’s invoices so they get money today instead of 30-90 days from now. Decent enough, this is probably useful I thought. I go to the company’s office in New York, in financial district for the interview. Goes fine, I ask what kind of customers they have, what interest they charge and it quickly becomes apparent that this company is basically a roundabout-welldressed shylock.

I guess the interview went well enough and it’s a smallish company so the CEO wants to personally vet potential new hires, I meet him in his office. An ex wallstreet banker that started his own company, imagine al Pacino from that movie where he plays the devil. It was a really odd conversation, and it was obvious to both of us that we didn’t see eye to eye. The one thing I remember saying, and the context begets me, I said “we really do build our own personal hell in this world don’t we?” And I remember it being kind of a Freudian slip of a realization, as I sat across from this man who was obviously quite proud of his own self-built cage. He just looked at me funny and asked what the hell I meant by that, and I couldn’t really articulate it, however they still they gave me a job offer (it was terrible, I didn’t take it, the interviewer was practically abusive towards me on the phone for not graciously accepting it or even negotiating).

I just think to myself, these people in their endless drive for personal material wealth, their complete inability to grasp the value of anything worldly and good, how did they stray so far from the path? Who/what led them away and blinded them from seeing natural goodness?

A more critical review of the same book, albeit from a former private equity veteran: https://www.bloomberg.com/news/articles/2025-06-06/private-e...