Diary of a Very Bad Year

An anonymous hedge fund manager's real-time interviews during the 2008 financial crisis, capturing Wall Street's fear, confusion, and eventual return to business as usual.

Diary of a Very Bad Year is a collection of nine interviews conducted between September 2007 and the summer of 2009, as the global financial system nearly collapsed. The anonymous hedge fund manager (HFM) talked with Keith Gessen of n+1 magazine, explaining in plain language what was happening on Wall Street while it was happening. No hindsight, no spin, just real-time analysis from inside the machine.

The book covers the full arc of the crisis. It starts with the first rumblings in the subprime mortgage market, moves through the collapse of Bear Stearns and Lehman Brothers, the AIG bailout, the TARP controversy, and the slow, uneven recovery. Along the way, HFM explains how mortgage-backed securities worked, why bank runs still happen in the modern age, what zombie banks are, and why the financial system went right back to risky behavior as soon as the worst had passed.

What makes this book stand out is the honesty. HFM gets things wrong, changes his mind, and by the final interviews starts questioning whether his career in finance was worth it. He eventually leaves his hedge fund and buys a house in Texas. For anyone who wants to understand the 2008 crisis from the inside, without the jargon and without the sugar coating, this is one of the best books available.

Diary of a Very Bad Year - How a Literary Magazine Ended Up Interviewing a Hedge Fund Manager

This is part of my series retelling Diary of a Very Bad Year. Today we’re covering Keith Gessen’s introduction.

A friend of a friend

Keith Gessen got introduced to the anonymous hedge fund manager (HFM) in late 2006. Someone called HFM a “financial genius” who ran the emerging markets desk at a midtown hedge fund. Gessen was skeptical. He knew plenty of people from college who went into finance, but mostly for the lifestyle. Working hard, drinking beer, watching football.