Best Advanced Investing Books

Below you’ll find some of my favorite advanced investing books on a wide variety of investment strategies and approaches.

I refer to them as more advanced investing books because they are beyond a typical and somewhat over simplified buy and hold investing strategy following an allocation model in stocks and bonds.

All these books are among the three hundred plus financial books I’ve actually read over the years with the exception of the one new tax book as indicated. This allows me to share with you my own experiences and opinions in relation to the book, why I like the book, and the type of investor that might find it interesting.

Note that most of the books are older classics with timeless information.

This list is ideal if you’re looking for alternatives to buy and hold investing. 

Be sure to check out the last section with wealth management books. It relates to all investors since the best investment strategies are meaningless without the skills to manage and sustain the wealth generated from investing.

Advanced Investing Books for Stock Investors

The books in this section range from how to evaluate investments to investing around economic cycles.

One Up on Wall Street

My dad brought this book to me in 1990 when I lived in Bermuda. While a lot has changed in the stock market since then, I still love the dividend adjusted PEG formula Peter Lynch explained in this investing classic.

Fidelity Investment’s Lynch is often considered the best mutual fund manager of all times so much of his advice is timeless.

How to Make Money in Stocks

Investor’s Business Daily Founder William O’Neill shares the CAN SLIM investing strategy for stocks. It combines fundamental analysis with technical analysis to give investors an edge.

I studied this book religiously years ago when I was a stock picker. I even sold covered calls on my IBD selections. CAN SLIM stocks tend to have higher option premiums, and hence, higher covered call income since the companies are usually newer growth stocks and more thus volatile.

There are investment firms that use the CAN SLIM strategy to invest in stocks for a hefty financial advisor fee but individual investors can implement the CAN SLIM method themselves if they choose. 

IBD’s “Big Picture” guides investors to reduce stock holdings during higher risk periods and increase stock percentages when factors suggest it’s time to do so. I love this about IBD because it helps manage portfolio risk. 

This classic is still one of my favorite resources for individual stock investors.

Check out How to Make Money in Stocks book here.

The Intelligent Investor

No list of advanced investing books would be complete without The Intelligent Investor by Benjamin Graham. This classic teaches a value investing approach.

Graham was, in fact, Warren Buffett’s employer and mentor.

I have my dad’s copy of this book, with his markings in it. Lest you think this book is only about a bottom up approach to stock investing, the content below caught my eye, perhaps because Dad had underlined it.

“On the whole, it may be better for the investor to do his stock buying except when the general market level is much higher than can be justified by well established standards of value.”

Another favorite line from The Intelligent Investor: “Nothing important in Wall Street can be counted on to occur exactly in the same way as it happened before.”

This clearly indicates there’s more to investing than buy and hold using a fixed asset allocation model no matter what. It even encourages tactical vs strategic investing. 

I love that Graham considers bond yields, market fluctuations and even inflation vs many other stock selection books that focus only on company fundamentals.

Check out The Intelligent Investor here.

The All Season Investor

Martin Pring covers basic risk management by owning a variety of asset classes in different forms, including individual securities and fund types.

Pring takes managing portfolio risk a step further where many investing books stop, however; Pring explains the various economic cycles, and how to identify where we are in the economic cycle at any given time.

This is pretty much priceless information (for less than the cost of even a Super Cuts haircut) less than the lost of since economic cycles a the primary driver of investment returns contrary to what many investors have been led to believe. 

Martin also explains how the various asset classes perform during different phases of the economic cycle making this book required reading for all investors.

Even though this book was published it 1992 most of the information is timeless and the content is unique.

Mastering the Market Cycle

This is an ideal book if you have some concern that a fixed asset allocation model may not be the best way for you to invest.

Howard Marks, Oaktree Capital Management cofounder, explains market cycles in an easy to understand way. Mark’s guide to market assessment on page 212 is worth the price of the book.

The Ivy Portfolio

Meb Faber explains how renowned endowment funds have gotten the results they have with a simple, diversified ETF portfolio.

More advanced investment strategies that are tactical in nature and other options are explained as well for investors who choose to go beyond the asset allocation model that Meb presents in his popularized Ivy Portfolio. Extensive past performance data is available to Allocate Smartly members for both Meb’s fixed Ivy Portfolio as well as his other tactical strategies.

This book influenced my investing years ago when I discovered the logic of investing in defensive assets besides bonds, particularly during periods of high stock valuations and low interest rates. The Ivy Portfolio was also one of the three strategies I combined when I developed my own ETF covered call strategy.

The Ivy Portfolio book is a good read for both beginning investors as well as those looking to become more advanced investors.  I no longer use a fixed asset allocation model myself, however, as described in the first section of this book. 

Unexpected Returns

If you want a better understanding of why and how economic factors drive investment returns, you’ll enjoy Ed Easterling’s book.

This is one of the most powerful investing books you’ll ever read. If you’re a “set it and forget it” asset allocation investor looking to become a more advanced investor, read this book.

It will take your knowledge to the next level.

Check out Unexpected Returns here.

Hot Commodities

While Jim Rogers hadn’t had the best investment returns last time I checked, he is still a leading commodity expert, motorcycle and all. And who knows, Rogers may have the last laugh yet.

If you want to learn more about oil, gold, coffee, and more, you’ll enjoy this story based book.

The Perfect Portfolio

After the bear markets in the 2000s decade, I hungrily consumed this book from former college professor Leland Hevner.

My thinking was that I could avoid the common problem with a financial advisor potentially being slightly biased when providing investment education since a college professor doesn’t sell wealth management services.

The Perfect Portfolio explains how you can construct a much more diverse ETF portfolio that holds gold, commodities and other defensive assets when needed.

Then it steps more active investors through creating an automated trading plan that lets limits losses while letting capital gains run.

I had evaluated and invested in a couple of hedge funds in the 2000s decade, and this book confirmed that I could create my own little investing method somewhere between a hedge fund and a more traditional portfolio while side stepping the worst of bear markets. This was something my financial advisors hadn’t accomplished on my behalf that decade.

Meb Faber’s book, The Ivy Portfolio which I read about the same time suggested the same thing so I was seeing a pattern that was leading me away from a fixed asset allocation model and toward a more advanced investing strategy.

The Perfect Portfolio advanced my knowledge about including defensive investments in a systematic portfolio.

It provided the education for becoming a more active investor albeit it was a little more complicated than I wanted.

Fortunately, now I use a much simpler method from Allocate Smartly that takes me an hour a month, has historically beaten a stock bond index portfolio with about half the risk shown by over 50 years of back testing data.

But reading The Perfect Portfolio was very educational and a steppingstone to my current investing strategy so I keep it on my list of favorite advanced investing books.

Advanced Investing Books for Traders

Many investors like to allocate a portion of their investment savings for trading vs long term investing so I’ve included some trading books for more advaned investors.

The books in this section are about how to trade as well as entertaining stories of traders who always seem mysteriously alluring.

In my second job after college I was an accountant for the firm’s energy products and options. (Note: Years later I married one of the traders, Larry Gaines, and we co-founded Power Cycle Trading over a decade ago based on his career trading options for over 30 years.)

Come into My Trading Room

Dr. Alexander Elder, M.D. explains various chart patterns and strategies to get started trading using the 3 M’s, Mind, Method, and Money.

It may seem odd that a trained physician is a trader. In our option trading education business, however, many customers are doctors and engineers. There seems to be a commonality in the way a trader thinks and the way engineers and doctors think.

Millionaire Traders

Authors Kathy Lien and Boris Schlossberg interview 12 people who reportedly turned as little as $1,000 into fortunes.

I read this book when I tested out trading before deciding I’m an investor, not a trader, at heart. Trading just wasn’t how I wanted to spend my time but if you have an interest in trading, you’ll enjoy this entertaining book.

Market Wizards

 

Jack Schwager shares the real stories behind top traders, including Paul Tudor Jones, Ed Seykota, Austinite Michael Marcus, Richard Dennis, William O’Neil, Jim Rogers, and more.

Market Wizards is both educational and entertaining at the same time.

Way of the Turtle

Richard Dennis and Bill Eckhardt did an experiment to see if they could teach inexperienced investors, dubbed “turtles”, to successfully trade using a system based model.

One of the turtles, Curtis Faith, shares the fascinating story where he made more than $30 million in four years. It might be worth $23.75 to gain the insights that accomplished this level of wealth in such a short time even if you don’t want to trade.

Surely it goes beyond following a trading model; there are always investing emotions at play as well, and Curtis tells it all.

Alternative Investing Books

This section lists advanced investing books that are geared toward usually overlooked alternative income producing assets vs just stocks and bonds, the mainstay of most portfolios.

Killing Sacred Cows

Garrett Gunderson began as a traditional financial advisor before a lightbulb (or several) went off luring him to focus on alternative wealth building.

Like me, Garrett points out that wealth is built from real estate or business more often than investing in stocks.

Managing risk with insurance, minimizing taxes and investment fees, and being happy in life are primary focuses of this easy but informative advanced investing book.

Multiple Streams of Income

Robert Allen brought alternative income streams to mainstream investors decades before the popular “Retire Early” movement known as FIRE.

It baffles me that more investors don’t apply Robert’s alternative wealth strategies, especially soon to be retirees short on retirement savings sufficient to sustain a lifetime of retirement withdrawals.

Instead of using only using retirement account withdrawals which deplete investment savings, investors can create one or mor income streams to reduce the amount of retirement savings needed. Robert’s book provides an overview of the various methods. While this is an older book, Robert’s methods are still relevant today.

Various editions of Multiple Streams of Income delve into selling covered calls, real estate and even online business.

Robert’s strategies are now found in many other books, but this is the book that’s still on my bookshelf because it opened my eyes to the many ways to build wealth besides stocks, so I share it here.

Rich Dad Poor Dad

Reading this Robert Kiyosaki book years ago gave me an insight that has yielded positive results for me. Aligning with Robert Allen’s philosophy, Robert reminds us the seriously wealthy get that way from business or real estate more often than a lifetime of frugal living and stock market investing.

Robert’s simple quadrant helps investors easily see that the US tax system has provisions that help small business and real estate investors. These income producing assets can, therefore, be an excellent alternative wealth building strategy for more advanced investors.

Related Books for Advanced Investors

These books aren’t about advanced investing, per se.

Instead, they present information helpful for advanced investing implementation, or information that successful advanced investors have mastered.

And we can learn from them for sure.

The Black Swan

Nassim Nicholas Table writes of the highly improbable and its impact on investors. Completely unexpected events happen, and they can wreak havoc on your investment plan.

Wise investors are aware of this phenomenon and protect their assets for the occasional black swan.

Check out The Black Swan here.

The Changing World Order

This is one of my favorite books, period. Boring it is not; it kept me entertained during a long road trip tp Taos recently for an impromptu ski trip.

You’ll never again think 5 year annualized investment returns are remotely adequate for evaluating an investment or assessing a financial advisor after reading this highly educational book from Ray Dalio. 

The information in this book certainly influenced my investment course.

I liked it so much I bought the paper version as well as the audio format so I could easily reference the charts and data.

You may recognize Ray Dalio as the creator of the popular All Weather Portfolio. 

This book is a game changer that will appeal to more advanced investors and anyone looking to understand the role global economics play in influencing investment returns.

Check out The Changing World Order.

Strengths Finder

This is a weird find on an advanced investing book list but here’s why it’s included.

Every investor benefits from knowing their skills. For example, when I took the Strength’s Finder tests years ago, I was surprised to discover my highest skills were analysis and strategy.

Then I understood why I enjoyed investing after wondering for years why I was such a nerd about investing (and a woman, at that).

It makes sense for me to analyze investment strategies and implement them myself based on my strength findings. This book helped me see why I’m driven to be a financial coach because I get to teach others to evaluate investments.

On the other hand, an investor whose top skills are harmony, woo, or empathy might be happier hiring a financial advisor, or being a passive investor.

You may think you already know what you like, but you might be surprised. Confirm your strengths and create a wealth plan around what aligns with your personality. This is the way to be happy, the real factor behind being wealthy.

The Richest Man in Babylon

In 1926, George Samuel Clason probably had no idea the wealth building principles in his little book would stick around for over a century.

While this isn’t truly an advanced investing book, the practices in this book can help all investors sustain and manage wealth. This book is also an ideal graduation gift.

Lower Your Taxes – BIG TIME! 2023-2024: Small Business Wealth Building and Tax Reduction Secrets

What U.S. citizen doesn’t need this book? This is the one book on this post of advanced investing books which I haven’t read yet but I’m replacing the 2020 edition of How to Pay Zero Taxes (which I didn’t successfully do, trust me on this?) with this new book from Sandy Botkin, CPA.

I have enjoyed Sandy’s tax saving books for well over a decade. Check out Sandy’s latest tax book here.

Money: Master the Game: 7 Simple Steps to Financial Freedom

When President Clinton, Nelson Mandela, Paul Tutor Jones (yeah), Michael Jordan, and Mother Teresa have brought in Tony to help them deal with their s%$t, we know the guy has some powerful information that’s worth a $10 investment.

While I don’t agree with Tony Robbins’ buy and hold investing methods for more advanced investors, and the financial data is now a bit dated, the timeless money mindset content in this book is worth it’s weight in gold.

The best investment strategy in the world won’t be implemented if you’re investing emotionally due to your grandma’s depression era scarcity issues, the burden that you lost money in a previous bear market, or don’t believe deep in your soul that you can invest successfully.

The Fourth Turning

This 1997 book by William Strauss and Neil Howe explains how generations go through approximately twenty year periods and every fourth generation change causes disruptive changes that affect everything from politics to, of course, finances.

If you want to better understand the current, crazy, social and political divisions, and even your family members better, I highly recommend this book which was spot in in predicting our current economic situation decades ago.

If, like me, you understand that economic happenings drive investment returns, you’ll see the importance of this book in relation to your investments. It’s a must read.

Check out The Fourth Turning.

How to Be a Billionaire

Even though I’m not a billionaire and it looks doubtful I ever will be, I loved this book by Milton Fridson.

One of my favorite lines is “Buy low, sell high”. In fact, there’s an entire chapter entitled Buy Low.

This is a core financial principle we all apply to buying everything from groceries to clothes, but it’s completely overlooked in popular buy and hold asset allocation models.

This book addresses this core financial principle and many more.

Advanced Investing Books Summary

Peruse this list of books and find the one or two that meet you where you are now.

Becoming a more advanced investor is a journey, not a sprint, as you can see from my own journey outlined through the more advanced investing books books shared here.

 

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You can also watch my video on the best books for advanced investors.