Personal Development

10 of the All-Time Best Business Books for Entrepreneurs

Expertise: Mortgages & Creative Financing, Business Management, Landlording & Rental Properties, Commercial Real Estate, Real Estate Deal Analysis & Advice, Real Estate Investing Basics, Personal Development, Real Estate News & Commentary
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A while back I wrote a list of the first 10 books I would read and the order in which I would read them when starting out to become a real estate investor. While knowing how to be a real estate investor is rather important to becoming one, real estate investment is also a business. And to have great success in real estate, you need to run your investments like they are a business and not some hobby.

Thus, here is the list of the first 10 books I would recommend to an aspiring entrepreneur, and I would recommend reading them in tandem with the first 10 real estate books mentioned in the previous article. (Reading is good, people. After all, they say the average CEO reads 60 books a year, although admittedly, I suspect that number is an exaggeration.)

1. The E-Myth by Michael E. Gerber

Michael Gerber’s classic The E-Myth has my favorite anecdote about what can go wrong in even a successful small business,

“‘It’s seven o’clock,’ she said, wiping her eyes with her apron, as though reading my mind. ‘Do you realize I’ve been here since three o’clock this morning? And that I was up at two to get ready? And that by the time I get the pies ready, open for business, take care of my customers, clean up, close up, do the shopping, reconcile the cash register, go to the bank, have dinner and get the pies ready for tomorrow’s bake, it’ll be nine thirty or ten o’clock tonight, and by the time I do all that, by the time any normal person, for God’s sake, would say that the day was done, I will then also need to sit down and begin to figure out how I’m going to pay the rent next month?” 

The work can just go on forever and ever. It's for this reason that systems are so important. Build your business as if you were going to franchise it. Build it so someone can step into your place and take over the systems you have put in place right away. Putting such systems in place won't happen overnight, but it's what you should intend to create, step-by-step, from the outset.

2. Traction by Gino Wickman

I see Traction as starting up where The E-Myth leaves off. It offers the next step to systematize your business, with more concrete examples and methods. Wickman even notes the exact time you should start to systematize something,

There was probably a time when your business demanded that you fly by the seat of your pants. This involved reacting to every customer request, thinking on your toes, and being creative on the fly. At some point, though, certain actions have revealed themselves as redundant. That’s when you should systematize them.”

The book outlines how to go from a free-wheeling entrepreneur who shoots from the hip to building your Entrepreneurial Operating System (EOS) that provides the framework with which to scale and is definitely recommended.

Related: Unpopular Opinion: Self-Help Books Do More Harm Than Good

3. Who by Geoff Smart & Randy Street

As Geoff Smart and Randy Street put it in Who, “Your success as a manager is simply the result of how good you are at hiring the people around you.”

Like it or not, if growth is what you want, then sooner or later, you will need to hire someone (and likely several someones). Hiring is not something to be taken lightly. The quality of your company, almost by definition, will reflect the quality of the people in it.

Smart and Street lay out a three-interview method (the final interview being the prospect’s references) for bringing on a new employee. The first is to sort the wheat from the chaff. The second is the “topgrading interview” that goes through their resume job by job. This gives you a fuller, chronological version of the prospect’s work history and makes it much harder for them to leave out information they would prefer you didn’t know.

It also gives you a much better view of their overall career and abilities rather than some disconnected highlights and a few memorized interview cliches. A must-read for anyone hiring, in my humble opinion.

4. First, Break All the Rules by Marcus Buckingham & Gallup Organization

Per First, Break All the Rules, a lot of what we think we know about productivity and how to manage teams is simply wrong. Gallup did an enormous amount of research analyzing the strengths of hundreds of thousands of people and found, for example, that you should focus on improving your strengths, not fixing your weaknesses,

“In stark contrast, our studies indicate that people who do have the opportunity to focus on their strengths every day are six times as likely to be engaged in their jobs and more than three times as likely to report having an excellent quality of life in general.”

First, Break All the Rules is the culmination of that research and how it relates to management. First, you need to, well, “break all the rules.” One of those supposed rules is to “treat everyone the same.”

While you should be fair to everyone, everyone is different and people respond to different things. So you need to tailor your approach to each individual person. There is much more great advice on how to manage and motivate people throughout this book.

male hand writing in notebook with pen

5. Scaling Up by Verne Harnish

Verne Harnish is considered by many to be the ultimate guru on scaling businesses. In my judgment, Scaling Up picks up where Traction leaves off and goes into more detail about how to create a streamlined-business that can scale quickly.

“…Along the journey, there is a set of habits—routines—that will make the climb easier. ‘Routine sets you free’ is a key driving principle behind our methodologies and tools. you may set a goal to lose weight, but unless you change some daily and weekly routines, it will never be accomplished. Goals without routines are wishes; routines without goals are aimless. The most successful business leaders have a clear vision and the disciplines (routines) to make it a reality.” 

Harnish dives deep into more complex topics like accounting, key performance indicators, and other methods by which to measure performance and fine-tune each and every part of your business.

6. Never Split the Difference by Chris Voss

Negotiating is a fact of life and business. One way or another, you’re going to have to do it. And as far as negotiating goes, there’s no better book to turn to than Never Split the Difference by Chris Voss (unless you’re doing real-estate-specific negotiating, for which you should also turn to J. Scott’s The Book on Negotiating Real Estate).

Voss’s highly engaging book turns over all sorts of conventional wisdom and offers a wide range of helpful tips. Mirroring, for example, is one of my favorites.

“Repeat the last three words, or the critical words, of what someone has just said. We fear what’s different and are drawn to what’s similar. Mirroring is the art of insinuating similarity, which facilitates bonding. Use mirrors to encourage the other side to empathize and bond with you, to keep people talking, to buy your side time to regroup, and encourage your counterparts to reveal their strategy.”

There is much more, including why you should ask “how” or “what” questions instead of “why” questions. But you’ll have to pick up the book to find out why.

Related: 7 Top Business Books to Help You Put Vital Systems in Place

7. Good to Great by Jim Collins

Jim Collins is, more or less, the ultimate business expert. In Good to Great, he analyzed 15 companies that went from very mediocre performances to outperforming the Dow Jones by a factor of three for 15 consecutive years. He then compared those companies to competitors who made no such jump. Collins and his team analyzed those successful companies carefully to find what they shared in common.

Like Street and Smart, Collins and his team found that the who was more important than the what. They also found how critical leadership was, particularly what they call “Level 5 leadership.” In short, a mix of extreme humility and extreme will.

But the concept I thought was the most helpful was the “Hedgehog Concept.”

“The fox knows many things, but the hedgehog knows one big thing… Berlin extrapolated from this little parable to divide people into two basic groups: foxes and hedgehogs. Foxes pursue many ends at the same time and see the world in all its complexity. They are ‘scattered or diffuse, moving on many levels’… never integrating their thinking into one overall concept or unifying vision. Hedgehogs, on the other hand, simplify a complex world into a single organizing idea, a basic principle or concept that unifies and guides everything.” 

Businesses that do one (or just a few) things well will dominate those who are “scattered or diffuse” every single time.

8. Built to Last by Jim Collins

In Built to Last, Collins looks at what makes companies stand the test of time. What are the key factors for long-term greatness?

Interestingly enough, one of them is what Collins calls a BHAG (Big, Hairy, Audacious Goal). For example, in 1950, Boeing made the BHAG to “become the dominant player in commercial aircraft and bring the world into the jet age” and Giro to “become the Nike of the cycling industry” in 1986.

Great, long-lasting companies shoot for the stars, they don’t settle for just being there.

Casual man or hipster drinking coffee and looking at digital tablet screen near the window at home with morning light. Man checking internet application on digital tablet computer, modern lifestyle concept, flare light

9. Great by Choice by Jim Collins & Morten Hansen

Collins makes his third entry on this list with Great by Choice, a book about how to survive in a volatile economy. It was written with the 2008 financial crisis in mind but applies just the same to today's coronavirus-induced recession.

Of the many insights Collins offers, the most important is the concept of 20-mile marching, a reference to the philosophy of famed explorer Roald Amundsen. As he puts it:

“The 20 Mile March is more than a philosophy. It’s about having concrete, clear, intelligent and rigorously pursued performance mechanisms that keep you on track. The 20 Mile March creates two types of self-imposed discomfort: (1) the discomfort of unwavering commitment to high performance in difficult conditions, and (2) the discomfort of holding back in good conditions.”

10. Antifragile by Nassim Nicholas Taleb

Nassim Nicholas Taleb is one of the most unique thinkers today and his book Antifragile is essential for how to view your business in the fragile world economy. As I described his ideas in a previous article:

"Antifragility doesn't describe something that can survive disorder or even a downturn. For that, he uses the term ‘robust.'" Instead, antifragility is something that gains from disorder…

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“…When it comes to investing, Taleb recommends trying to find investments with small costs, but potentially, even if unlikely, big payoffs (i.e. nonlinearity). One example he gives is when he reviewed Fannie Mae’s balance sheet in the early- to mid-2000s. He saw that when Fannie Mae’s portfolio was stress tested, it failed miserably when defaults went up ever so slightly.

“He had no idea what would be the cause of this disturbance. That would require predictive power we don’t have. But he did see that Fannie Mae was particularly fragile and worth shorting.”

Keeping strong cash reserves, maintaining good credit, and finding a stable of private lenders to survive and then take advantage of the (usually) low asset prices during recessions are key steps to becoming antifragile.

Honorable Mentions

And how about a few honorable mentions for the book worms out there.

How the Mighty Fall by Jim Collins

Collins spent a lot of time telling you how companies succeed. In How the Mighty Fall, he tells you how they fail and thereby, what to avoid. Hint: Doing too many different things and getting overleveraged are bad ideas.

Overcoming the Five Dysfunctions of a Team by Patrick Lencioni

Teamwork is essential in business and unfortunately, many teams are quite dysfunctional. Luckily, Patrick Lencioni is here to help you fix that problem with Overcoming the Five Dysfunctions of a Team.

Tribal Leadership by Dave Logan, John King & Halee Fischer- Wright

By nature, humans think tribally. We like to be part of a group, generally speaking. Wise leaders understand this and how to work within the dynamics of that “tribe.” Learn all about it in Tribal Leadership.

Scale by Jeff Hoffman & David Finkel

Scale covers much of the same ground as Scaling Up but still makes for a great companion. Scaling is a complex and critical task for any intermediate-sized business. It’s essential to get it right, and Hoffman and Finkel provide another helpful framework for how to do so.

The 4-Hour Workweek by Timothy Ferriss

The 4-Hour Workweek is easily the best and worst book ever written. Timothy Ferriss offers a cornucopia of ways to delegate, automate, and save time. But he has also found a way to convince a lot of people they should put off their work on others and be as lazy as possible. Use the good stuff in it, but please drop the bad.

Zero to One by Peter Thiel

According to Zero to One, “The biggest secret in venture capital is that the best investment in a successful fund equals or outperforms the entire rest of the fund combined.”

While fund management and venture capital are unlikely to be in many of your futures, this book really highlights the importance of focus. The best things you do will be the biggest winners by far. Don’t overextend yourself into too many things.

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What are you reading and how is it helping you?

Share your own recommendations—or thoughts on our picks—in the comments.

Andrew Syrios has been investing in real estate for over a decade and is a partner with Stewardship Investments, LLC along with his brother Phillip ...
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    Jerry W. Investor from Thermopolis, Wyoming
    Replied 29 days ago
    Andrew, While we have fairly different philosophies, I greatly admire your knowledge in the field. This article is no exception. Very good books and quick points as to why they are so good. Of course half of being a good book is the timing on when you read it and how it applies to your current situation. Two books that I highly recommend is The Morning Miracle, and The One Thing.
    Andrew Syrios Residential Real Estate Investor from Kansas City, MO
    Replied 27 days ago
    Thank you Jerry! And I agree, those are both very good books (with one reservation about The Miracle Morning; don't shortchange the amount of sleep you get, which he doesn't necessarily recommend, but he doesn't stress the importance of getting enough sleep). In fact, I have a final article in this three-part series of top 10 books coming out soon. The last one will be on self-development books, and both of those are on it.
    Trevor Covington Investor from Syracuse, Utah
    Replied 15 days ago
    Thanks for the recommendations. You might also like Atomic Habits by James Clear and The Ultimate Sales Machine by Chet Holmes. They are both full of very actionable and helpful insights.