72 Books Like What I Learned Losing a Million Dollars

I didn’t read Liar’s Poker until fairly recently.

I started working for Dow Jones Newswires during the dot-com boom and saw how greed could drive markets. I worked through the housing boom in the Aughts and the financial crisis, and then started covering bitcoin around 2013. So by the time I got to Lewis’s book, I had a good understanding of how people can become obsessed with money.

But Lewis is just such a good writer, and has such insights into how markets work, that a book about bond buyers in the 1980s still feels like it’s about people trading so many other things today. 

As everyone knows at this point, anything Michael Lewis writes will be enormous fun to read, while being about something really important—something he’ll make you care about even if you didn’t when you started the book.

In this case, the subject is people who bet on the direction of mortgages (and thus, house prices), and how those who bet on a huge plunge were right. This book has an amazing cast of characters, all richly drawn: some are smart, some are not so smart; some are excellent schmoozers, some can barely tolerate human interaction; some care a lot about money, some care more about being right, especially if everyone else is wrong.

Each book I've recommended cries out to be made into a movie. This one actually was.

This fascinating read tells the story of the rise and then spectacular fall of the once celebrated hedge fund Long-Term Capital Management.

What made LTCM so attractive to Wall Street investors was its stable of "dream team" quants and financial minds, led by the laconic John Merriweather. Merriweather (featured in the opening Chapter of Liar's Poker) was a former Solomon Brothers bond-trading guru, who after leaving the firm amid a scandal managed to assemble a team of financial powerhouses that included two Nobel Laureates as well as a cadre of respected traders.

From 1993 to 1997 LTCM's returns were first-rate; the sky seemed the limit for this small band of supertraders, professors, and modelers who arrogantly considered themselves a cut above the rest of The Street.

But in 1998, it all came crashing down...and right quick. Having believed their financial models could accurately predict price action not just in… show more.

A history of hedge funds might seem like a weird recommendation by someone who has written a paean to passive investing.

But my favourite books use a subject to tell a much broader story, and Mallaby’s definitive book on the hedge industry manages to show how even the most illustrious investing careers can fizzle out as market regimes ebb and flow.  

There are quite a few titles in the Market Wizards book collection, but my personal favorite is still the first of the series. In the book, Jack interviews different successful traders and investors. You’ll get to learn the basics of what they did (I personally know of one reader who started a successful hedge fund after reading one chapter of this book), but more importantly, you will be able to understand and explore the mindset of winning traders. Reading this book will help you mimic the behavior of some of the great traders of our time.

Of all the books about trading written over the decades, perhaps none is still so beloved, revered, and followed as this 1923 classic by journalist Edwin Lefèvre. Although technically a work of fiction, the book really is about the life and trading style of one of the greatest speculators of all time, Jesse Livermore (told under the guise of “Larry Livingston”).

What makes this book such a treasure is not just its fun prose, and interesting glimpse into what the process of investing in old exchanges and “bucket shops” was over a century ago, when ticker-tape and board boys with chalk and ladders were one’s only information about market prices, but also how the mind of one of the world’s greatest traders worked.

This book offers many gems of knowledge about trading—based upon the general principle that, although methods and technologies change, human nature does not and therefore “there is… show more.

Good trading does not always involve just buying and selling decisions. If it was, trading would be much easier! To be a successful trader, you must have your psychological “house” in order. And that is what this book is superb for. Trade Your Way To Financial Freedom assists you in navigating the turbulent mental, emotional and psychological waters all traders face.

This book explains every candlestick pattern you can think of, and more. The best part is that Bulkowski has tested each pattern and summarized the results. He puts the best patterns at the front of the book, so you do not need to read everything to find what you are really looking for. I use it as a reference quite often.

Trading is a mental sport.

I have been teaching and mentoring traders since 1999. In that time I have seen over and over again that success comes from the ability to maintain discipline and withstand emotional discomfort.

Everybody wants to buy a system or strategy “that just works”. Well, as somebody who has developed many great strategies I can tell you this harsh truth… The best system in the world is worthless if you can’t follow its rules.

This is the core reason why over 90% of traders fail, lose money, and quit in disgust.

This book is one of the best I have found on the subject of trading discipline and mindset. If you are at all serious about your success in the market…start here!

Capitalism is a saga of booms and busts, and few tell the story with as much vim and rigor as the historian Edward Chancellor. Across centuries of hype cycles, Chancellor shows why entire cultures get sucked into brazen schemes promising riches and utopia.

Some of those schemes help facilitate the rise of genuinely revolutionary technologies, like the steam engine. And others go absolutely nowhere and end up destroying the lives of their many investors.