The Best Business/Investing Books I've Read over the Past 10 years.

I've been an avid reader for as long as I can remember. I believe in the power of knowledge and that the act of continuous deep learning can sharpen your mind and stimulate new organic ideas, even if those ideas aren't directly found in the text. A good business book will leave me with at least a few valuable nuggets, possibly a new perspective, and a better understanding of how the world works. I also appreciate a great story, and I often become more motivated in my own business when I'm immersed in a good book.

In recent years, I've noticed more online real estate and business gurus pushing their latest book launches. I even know a few local guys launching books. While not always true, these tend to be "fluffy" and motivational in nature, embellished, and too rudimentary or oversimplified to keep my attention. I don't need any more help "manifesting" or with mindset modification. I like nuts and bolts. I want to actually learn. Below are my thoughts on each book.

Main Street Money shined a light on how financial advisors often do more harm than good for the small to medium investor by way of leeching fees and spending more time attracting new clients' money than actually doing research and seeking alpha (outperforming the market).

I don't think blind index fund investing is the best strategy personally, but paying someone who isn't successful themselves to decide what buckets to invest your money into is even worse. There are some financial advisory teams who are managing larger investment portfolios in the tens and hundreds of millions who do provide value by way of tax loss harvesting, bond laddering, municipal bonds, CRTs and other strategies that would be difficult for the average person to track and execute themselves. Their fees are more justified by their tax strategy execution than their market outperformance. While I mainly invest in real estate, I've had periods where I invested in marketable securities like stocks and bonds and likely will again by way of dollar cost averaging or some similar strategy.

Shoe Dog is a captivating memoir of Nike founder Phil Knight. This guy took so many risks, built a business combining elements from multiple countries before google or smartphones or any of the tools that would have made this brand-building mission much more doable in today's world. Autobiographies and memoirs tend to be embellished but you got the sense from Phil Knight that there was a lot more truth than fiction in this story.

I loved hearing about how he went to Japan to secure the distribution rights for a Japanese running shoe and had the forethought to pitch importing them to the US as a winning business idea, raise the required capital, and execute. I'm not sure this could be replicated today, but what a great story about a household brand.

For this book we need to separate the artist from the art. Grant Cardone is currently involved in litigation, I've included a link to the actual lawsuit Here. I've also attached an excerpt from the Lawsuit's summary."The plaintiff alleged that, on social media, defendant Grant Cardone made opinion statements that he subjectively disbelieved and omitted material facts about the internal rate of return and distribution projections for real estate investment funds. The plaintiff also alleged that Cardone misstated material facts regarding the funds’ debt obligations." You'll have to make up your own mind about Grant and his company's conduct, that's outside the scope of this blog post.

The 10X Rule is a book that illustrates the idea that massive chaotic action beats slow careful planning much of the time. I can personally attest to this being true at least for certain periods in my real estate investing career. This book was extremely motivating to me at the time I read it near the beginning of my career, and it was exactly what I needed at the time to give me the kick in the butt I needed to just go for it. I would say that I am more in the careful planning phase of things now, but only because I took massive action early on to see what worked, and more importantly, what didn't. I also grew as a person from all that stress and learned a lot about myself. You won't find too many guru-written books in my collection, but this one is an exception.

I've never seen a more comprehensive how-to book on how to locate bargain properties than this one. Some of the ideas are fresh, some are rudimentary, but I do appreciate how deeply he considered every possible way to obtain leads and get deals. If your goal is to master your specific geographical market, a lot of these strategies would probably work out well for you.

For me, these strategies are very localized and geography-dependent. I fund flippers and developers nationwide, so driving around with a light-up pizza sign on my car that says "I fund flippers" probably isn't going to help much outside my local market. He has some other books that I actually plan to read soon when I get through my current list.

Okay there are 2 main biographies on Elon, but this one is from 2015 by Ashlee Vance and in my opinion is much better than the newer one by Walter Isaacson that attempts to cover the entire Musk saga plus bridge the gap from this older book through near present day. I did enjoy both but this one was miles ahead. I distinctly remember where I was when I read/listened to this book. I was driving from Iowa to Michigan 7.5 hours north to visit my Dad in fall of 2017. This actually inspired me to make my first big expansion moves, professionalize my company, and lead me to hire a childhood friend which ended up being one of the best business decisions I ever made for me and for him. It may seem silly that words on a paper can help to re-wire your brain, but this story was just so compelling, and even more-so because it lacked the embellishment of an autobiography or memoir. Biographies with input from the subject are my absolute favorite because they blend detail with accuracy.

When a story is this good, the book can't be bad. I am guilty of watching both the docuseries and separate documentary about the rise and fall of WeWork, which is an epic tale of Adam Neumann's seduction of everyone from Gwyneth Paltrow's first cousin, to titans like SoftBank's Masayoshi Son and Chase Bank's Jamie Dimon. I'm not sure I'm as bothered by his overoptimism and questionable tactics, as I am by the failures of the investment bankers to dig into what they were putting their investors' money into.

Elizabeth Holmes and Theranos took Adam Neumann's tactics a step further. With Adam, he at least provided a viable product (shared workspaces), and while he allegedly overhyped his projections and overstated financial health to investors to raise more money than he should have been able to, he probably did quite a bit of good to offset the bad. In the Elizabeth Holmes case, she was messing with people's lives by way of faking medical lab test results that resulted in false positives/negatives for real people, using machines from other companies and passing them off as her own. Another compelling story. I also watched the docuseries and documentary and absolutely loved all of them.

If you have the time to sit and read this 928 page behemoth that is The Prize, you will be rewarded by knowing more than you ever thought you would about the entire history of the oil industry from hundreds of years ago to almost present day. I have not been able to find this on audiobook (there's a 2 hour abridged version that isnt anything close to the gem this paperback book is). I have a confession... this book took me multiple years to read. I would get a little tired of oil and read other books in-between. I remember the day I finished it, and it's not the number of pages, it's the level of detail and keeping track of which company and who that can be daunting. I took my time with it and it was truly rewarding.

The Founders was a deep dive into the story of PayPal's struggle to navigate rapid growth while facing challenges from burn rate to Ebay to fraudsters. These people had very strong stomachs and I take inspiration from those who will their visions into existence. I was especially impressed to learn they invented Captcha as a mere side quest to deal with fraud issues. It takes special brains to build a revolutionary security product unintentionally.

What set PayPal apart from other online payment services of their time was ingenuity, creativity, and execution. It's not easy to build an amazing product. Getting it to scale is even more of a challenge. These founders went on to build a lot of product we all use today, like Youtube, Yelp, Linkedin, Tesla, etc.

This is a short book by one of the Paypal founders. I found the first 2/3 absolutely worthwhile and the last 1/3 fell completely off for me. The idea of horizontal progression vs vertical or building something that's 10x better than the next competition requires one to think outside the box and dream much bigger than we're used to. This book made me take a deeper look at my own business and really differentiate my offerings as a private money partner from my competition. Thinking big can be helpful, but not always.

Honorable Mentions

Some honorable mentions include "Crushing It in Apartments and Commercial Real Estate" by Brian H Murray, which is an interesting story about one guy's investment journey. I enjoyed "The Everything Store" by Brad Stone, which chronicles the rise of Amazon and Bezos. "The Richest Man In Babylon" by George S. Clason was memorable and a lot of investors like it.