March 23, 2021


Business decisions don’t come naturally to everyone.

If you’re thinking of starting your own business in today’s wildly competitive age, a bit of foreknowledge can save you a lot of time, pain and money. But getting this knowledge can be harder than you think.

“Business self-help” is, ironically, a big business. Amazon has thousands of e-books all promising to make you a millionaire. Social media “wealth mindset” gurus are only too happy to sell you the mystical secrets of real estate while quoting The Wolf of Wall Street. Much of this cottage industry is about selling the dream of wealth while avoiding the difficult reality of starting a business. After all, nine in ten startups never turn a profit.

So, how does one actually succeed in business?

You could start by gathering all the knowledge you can, first with some books on business.

The following books are quite popular and well-known to experts, but if you’re dipping your toes in the water, you can’t go wrong starting here for some basic strategy and inspiration.

DEEP WORK BY CAL NEWPORT (2016)Person writing in planner

Deep Work is about rethinking your approach to work itself. Author Cal Newport is a professor of Computer Science at Georgetown University and his approach is pragmatic. His main point is that your daily intellectual capacity and attention are limited resources.

An hour of “deep work” is worth more than a whole day being distracted.

In a way, he’s describing what others call “flow state” and ways to achieve it.

Newport avoids vague advice and jargon. His methodology includes note-taking to create awareness, timers and internet blockers. Without using the word, what he’s doing is advocating mindfulness around your work habits. And just so, he doesn’t want you to turn yourself into a maniacal productivity machine. He actually encourages boredom and downtime as a way to let the subconscious chew on problems and your motivation recharge.

That said, Newport’s book is at times a little polemical about the evils of social media. Now, he probably has a point — I don’t even want to know how many times we’ve checked Twitter since starting this article — but social media is simply unavoidable for many modern businesses. That said, the rest of his advice is quite salient.

THE E-MYTH REVISITED BY MICHAEL E. GERBER (2004)Man working at laptop

This book aims to deconstruct the big myths around starting a business. Namely, that most people who start a business understand what an entrepreneur’s role actually is. To paraphrase author Michael Gerber, just because you understand the technical work of your business doesn’t mean you can successfully run it.

To Gerber, there are three kinds of people in any business.

  1. Entrepreneurs look to the business’ future and create the systems.
  2. Managers train people to follow the systems.
  3. Technicians follow the system. They live in the present and do the work.

People get into trouble when they have to wear all these hats at once. When a Technician runs a business they forget to act like a manager or entrepreneur. They are only thinking about the work, not running or planning the system.

To Gerber, an entrepreneur’s goal is to create a business that will eventually run itself:

“If your business depends on you, you don’t own a business — you have a job.”

Gerber’s book is about the virtues of always holding onto the big picture and practical ways to structure your business and your relationship to it. Otherwise, being your own boss won’t be as cushy as you think.


Eric Ries adapts the scientific method to running a startup. The first thing to understand, he argues, is that a business plan is just a hypothesis until it’s been validated.

Therefore, a startup’s first goal is to prove their hypothesis. Focus on building a minimum viable product and measure its performance against your assumptions.

Don’t worry about building the perfect, most expensive product right out of the gate.

Basically, you should run an experiment, measure how customers respond with real-world data, adapt, and respond. With a variety of methodology and research, Ries shows you not only how to do this, but how to examine your data and determine if it is actually useful.

Remember: never fall in love with your vanity data. Entrepreneurs love to drink their own Kool-Aid, so to speak.


This is one of the Holy Texts of Silicon Valley, recommended by everyone from Michael Bloomberg to Steve Jobs. Here, Harvard Business School professor Clayton Christensen delves deep into what innovation and disruption actually mean. Where today, these terms have become exciting marketing doublespeak for unlimited wealth generation, what they truly are is destructive.

Disruption can lead to change and crisis. But how can you see it coming?

Where other business books talk about how to make it big, Christensen examines why companies fail. Christensen noticed that even big, market-leading companies tend to slide into obscurity and dissolution, and not for the reasons most MBAs learn. Why?

Well, one reason is that they are actually run well. They’re comfortable. They’re turning a profit, and so they keep doing what has been working. But then they don’t see the big change coming. Think Netflix vs. Blockbuster.

In some ways, this book is more academic and less directly pragmatic than some of the others. But it will help build your strategic view on where you should be thinking as an entrepreneur.


Dale Carnegie’s book was published in 1936 and it’s never gone out of print. Why? Because we’re just as awkward and as bad at listening to each other as we ever were. Most of us just aren’t naturally charismatic.

Dale Carnegie doesn’t advocate any kind of mind games here. He offers clear advice like remembering a person’s name and using it often.

People want to feel important, and want to feel heard. It’s not rocket science and we all know this sort of thing works.

Let’s be honest, this advice applies to all parts of your life, too. We’ve found dating tends to go much better when you remember their name. And that’s just one technique of dozens.

Even in the age of the internet, business relies on people. As an entrepreneur, these little tricks might make a difference to an investor. And as a manager, learning how to critique people without making them want to bonk you over the head with a laptop might help you stick around on this earth a while longer.


From here, you can always check out the famous biographies of businessmen like Bob Iger, Richard Branson or Bill Gates. Their advice here might not always be actionable however, as these business leaders were without fail in the right place at the right time. But it can be instructive to see where even the wealthy and powerful made mistakes.

For example, Super Pumped by Mike Isaac is all about the rise and fall of Travis Kalanick, and how his unorthodox tactics led not only to Uber’s rise, but his own personal downfall. It is useful to see how business really operates behind the scenes, and how battles over massive corporations can mirror struggles within smaller ones. And for more practical advice, check out Zero to One by Peter Thiel and the High Growth Handbook by Elad Gil.

I hope this list is helpful in building a strategy and appropriate expectations. So often we think all we need is work ethic and willpower when what we need is to change our focus and rethink our approach, both within ourselves and the nature of our work.