100 Books Like Unconventional Success

When I was growing up, I saw family members and friends, who were otherwise smart people who could master other aspects of their lives, have difficulty with personal finance decisions and investing. When my dad was laid off during a recession, he had some retirement money distributed to him, and I got interested in investing as he researched and tried with difficulty to handle this money himself. In my young adult years, I was a sponge to learn as much as I could about personal finance. 

I’ve spent my career studying the paradox that low-risk investing can lead to high returns. As an author and a multi-billion-dollar fund manager, I’ve seen firsthand how markets reward patience, discipline, and avoiding unnecessary risks. These books shaped my thinking—challenging conventional wisdom, deepening my understanding of risk, and reinforcing why defensive investing works. I love uncovering ideas that go against the grain, especially when they’re backed by data. Whether you’re an investor or just fascinated by how we make decisions under uncertainty, these books will change the way you see markets—and maybe even the way you invest.

I first started studying traders while working at London Business School in the early 1990s. This was the start of a lifelong fascination with traders and the psychology of financial behavior. Why do traders talk so much about their emotions? Why does so much of what they do fit so poorly with how economists think markets work? How do financial firms fail to notice rogue traders and other massive risks? And recently, why do investment banks and police forces both seem so good at avoiding uncomfortable knowledge? These are all questions that have fascinated me and which I have been lucky to be paid to research and advise on. 

I have been a stock market investor for over 50 years and made every mistake possible, including some original ones. For over 30 years now I have invested confidently and successfully and I share my experience with members and subscribers to my Monday Morning program. The accolades pour in on a daily basis.

I’ve been interested in investing for over four decades since I started as a finance PhD student at Wharton. Since then my research has focused on understanding the stock market. Early on, I tried applying my research to my investing. For example, I was convinced that a recently listed stock called Google was way overvalued—was I ever wrong! That got me to reflect on my investment philosophy—what did I truly believe about how markets really behaved? That brought me back to understanding and appreciating the contributors to Modern Portfolio Theory, which led to a fun decade-long book project. Currently I enjoy writing about investing through my blog.

I’m a money manager for high-net-worth individuals. During my Wall Street years, I was ranked number one in my category in the Institutional Investor All America Research Survey for nine consecutive years. The CFA Society New York presented me its Ben Graham Award in 2017. I’ve served as a governor of the CFA Institute and consultant to the Federal Reserve Board of Governors. My writings have appeared in the Wall Street Journal, Barron’s, the Financial Times, and various scholarly journals. I live in New York City with my wife, musicologist Elaine Sisman. We have two children and five grandchildren.

I’m a money manager for high-net-worth individuals. During my Wall Street years, I was ranked number one in my category in the Institutional Investor All America Research Survey for nine consecutive years. The CFA Society New York presented me its Ben Graham Award in 2017. I’ve served as a governor of the CFA Institute and consultant to the Federal Reserve Board of Governors. My writings have appeared in the Wall Street Journal, Barron’s, the Financial Times, and various scholarly journals. I live in New York City with my wife, musicologist Elaine Sisman. We have two children and five grandchildren.

I’m a money manager for high-net-worth individuals. During my Wall Street years, I was ranked number one in my category in the Institutional Investor All America Research Survey for nine consecutive years. The CFA Society New York presented me its Ben Graham Award in 2017. I’ve served as a governor of the CFA Institute and consultant to the Federal Reserve Board of Governors. My writings have appeared in the Wall Street Journal, Barron’s, the Financial Times, and various scholarly journals. I live in New York City with my wife, musicologist Elaine Sisman. We have two children and five grandchildren.

I collected coins a kid. I went to college and studied econ. I worked in a bank. I later became a financial journalist. And later, a professional money manager. I’ve always been fascinated by money…the way it moves around the world, the enormous role it plays in peoples’ lives, the power it gives a select few, the good it can do, and the way it grows. As a fee-only financial planner running my own shop, I'm only peripherally involved with Wall Street. That frees me to step back and look at the key players, the shenanigans, the sometimes awful greed. The books I’ve selected were instrumental in helping others make their money work for them.

Investing in the share market appears to be a bewildering, constantly shifting, extremely noisy, and busy world – one best left to the experts. Fortunes can be made but, equally, fortunes can be lost – with devastating results for those on the receiving end. And yet there are a few, simple, timeless principles to investing in the market successfully – and, ironically, those principles – known collectively as index or passive investing – will be more successful than all the noisy, busy stuff put out by the industry. In writing our book, this is what we would like as many people as possible to know. It’s not about being smart.