Underdog Advantages: Win Even When You’re Small

This article is an excerpt from the Shortform book guide to "The 33 Strategies of War" by Robert Greene. Shortform has the world's best summaries and analyses of books you should be reading.

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Are you the underdog? Do you feel out-gunned by the competition, whether in business or in life?

When you first start out on any conquest, chances are that your enemies will have more resources than you. However, this isn’t necessarily a problem. Robert Greene points out that smaller armies are more mobile and easier to conceal. And, if you don’t seem large enough to pose a significant threat, your opponents might simply ignore you.

Read more to learn about underdog advantages.

Don’t Let Small Size Hold You Back 

Greene suggests that there are certain underdog advantages. You can leverage your smaller size by building up your empire from many small conquests. You suddenly take possession of something that, by itself, is not worth your opponents’ time or energy to fight over. Then bide your time, building up your strength and waiting for others to forget about your recent conquest. Once they’ve forgotten about it, you can repeat the process. Greene asserts that over time you can quietly take over a large territory without anyone realizing what you’re up to until it’s too late for them to stop you.

If you want to learn how to be competitive in business or life even when you’re small, understand two strategies: avoiding pitched battles and fighting a guerrilla war.

Conquer Niche Markets

In Crossing the Chasm, Geoffrey Moore presents a business application of Greene’s strategy of building up an empire from pieces that, individually, your opponents don’t consider worth fighting for.

Moore’s strategy begins with identifying a niche market for your product. He emphasizes that the first market you target must be small enough for your company to dominate. This is important for two reasons: First, it makes it feasible for you to become the market leader in that niche, which helps you make sales. Second, and more to Greene’s point, if the market is small enough for a startup company to dominate, then it’s not worth enough for larger, established companies to bother fighting over. 

Moore advises that, once you’ve established yourself as the market leader in your target niche, you select another niche to expand into. Thus, you build up your market share one niche at a time until you dominate the whole market. In light of Greene’s discussion, part of the reason Moore’s strategy works is that by the time the old market leaders that you’ve displaced realize what’s happening, you’re already too well entrenched in too many market sectors for them to take back much of your market share.

Avoid Pitched Battles 

Greene points out that head-to-head battles are costly and often indecisive. Thus, it’s better to avoid them, especially when you’re small and don’t have resources to spare. To gain victory efficiently, Greene advises you to work your way into a situation where your strengths are pitted against your opponent’s weaknesses, and where their strengths and your weaknesses are less relevant. 

Greene says that when a large, powerful opponent moves to engage you head-on, your best bet may be a strategic retreat. Not only does this avoid the massive losses of a pitched battle and buy you more time to prepare, but it typically provokes your opponent to chase you, allowing you to lead them to a place where you can fight them on your terms. For this reason, Greene says that the defender in any conflict is statistically more likely to win than the aggressor.

Use Blue Ocean Strategy to Avoid Pitched Battles in the Business World

Blue Ocean Strategy might be interpreted as a business application of Greene’s strategic retreat. As we’ve discussed, with a blue ocean strategy you provide a unique product to create a new, uncontested market. W. Chan Kim and Renée Mauborgne argue that this is more profitable than direct competition because the new market gives your business more room to grow. In Greene’s terms, choosing to market a unique product is like retreating out of your competitors’ territory instead of fighting them head-to-head. 

Eventually, your competitors will realize that your product has reshaped the market, but by the time they give chase (in the form of introducing new products to compete directly with yours), they’ll have to fight on your terms because you already have experience in the new market. You’ve developed procedures for producing and marketing the product efficiently, as well as supply networks from which you source your materials. Meanwhile, to adapt to the changing market, your competitors will have to retool, which is slow and costly. In terms of Greene’s strategy, you’ve drawn your competitors away from their familiar territory into terrain where you have the advantage.

Although Kim and Mauborgne don’t refer to their strategy as a retreat, per se, they do emphasize the non-combative nature of their approach. At the time they first published Blue Ocean Strategy, this differentiated it sharply from most other business strategy books, which emphasized combative business competition. Viewed as a strategic retreat, it’s actually both combative and non-combative: You avoid combat up-front, but you gain an advantage over your enemies in the long run.

Fight a Guerrilla War

Greene explains that guerilla tactics are ideal for fighting a large, powerful enemy with a small force. Stage small attacks on your opponent’s weak spots and plunder their supplies to supplement your resources. Even though a single guerilla raid won’t hurt your enemy much, the effect of numerous small raids accumulates over time. This wears your enemy down without ever giving them the chance to defeat you in a pitched battle. It also shows them that they can’t push you around with impunity, even if they’ve put you into retreat.

Use Guerrilla Tactics to Conquer Your Habits

As Greene points out, guerilla tactics work because you can stage small raids relatively easily, even with limited resources. However, these tactics aren’t only useful in battle—other authors suggest applying these same principles to kick bad habits and cultivate good habits.

In Tiny Habits, behavioral scientist BJ Fogg argues that the key to cultivating productive or positive habits is to find the “tiny” version of the habit you want to create, something so easy that it doesn’t take much motivation to do it. He bases this on the Fogg behavioral model, which predicts that, given the opportunity to do something, you’ll do it whenever the combination of your motivation and ability (basically how easy it is) exceeds a certain threshold. Fogg observes that since your level of motivation naturally fluctuates and is difficult to control or predict, manipulating your ability to do something changes your behavior more than trying to manipulate your motivation.

Similarly, in Atomic Habits, James Clear argues that if you focus on making small positive changes to your habits, these small changes get compounded over time, and add up to massive improvements.

Combining these two ideas gives you a battle plan for optimizing your habits through a kind of internal guerilla warfare: Even if your arsenal of mental energy is small, you can use it to make small changes to your behavior, and over time these changes will add up to defeat bad habits and replace them with good ones. 
Underdog Advantages: Win Even When You’re Small

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  • How to win the war between you and those that seek to control you
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  • Why the little guy may actually have the biggest advantage

Elizabeth Whitworth

Elizabeth has a lifelong love of books. She devours nonfiction, especially in the areas of history, theology, science, and philosophy. A switch to audio books has kindled her enjoyment of well-narrated fiction, particularly Victorian and early 20th-century works. She appreciates idea-driven books—and a classic murder mystery now and then. Elizabeth has a blog and is writing a creative nonfiction book about the beginning and the end of suffering.

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