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What D2C Brands Can Learn About Strategy from Chess

By Nick Pietropinto

What D2C Brands Can Learn About Strategy from Chess

I’ve been playing chess since I was five years old. While the game of chess has given me countless hours of enjoyment, it has also taught me valuable lessons that I continue to apply both to my own business as well as the work I do with direct-to-consumer (D2C) clients.

At its core, chess is about strategy. It requires being able to understand the big picture, plan ahead, visualize next steps, anticipate and prepare for your opponents’ moves, and weigh risk versus gain. In other words: to be successful at chess, you need to apply strategic thinking.

The same can be said for business success. To advance your position and goals in business, you must be able to think strategically. The research backs this up. A McKinsey study revealed that the most important trait for high-performing business leaders is the ability to provide insights. The same report found that only 35 percent of executives feel that their strategies were built on effective insights, and only 25 percent think that their companies are good at both strategy and innovation.

Just how important is strategic thinking to business success? Very. Data shows that during a 10-year period, companies with clearly defined strategies showed a 304-percent improvement in profits and a 332-percent increase in sales over their competitors. A lack of strategy, on the other hand, can have a detrimental impact. Research conducted on companies that declared bankruptcy during the past 25 years indicates that the No. 1 contributor for these failures was bad strategy.

So what, then, constitutes “good” strategy? Studies conducted by the Wharton School revealed six skills essential to thinking strategically: the ability to anticipate, challenge, interpret, decide, align, and learn. These same skills needed for strategic thinking in the boardroom can be honed on the chessboard.

In the ever-evolving world of D2C marketing, strategic thinking is particularly critical. To cut through the competitive clutter and reach their target audiences, D2C brands must think strategically about the message they’re conveying, the platforms and media channels they’re using, and the customer experience they’re providing. Your direct response copywriting has to be on the point. You have to constantly look and plan ahead accordingly, anticipating their competitors’ moves and their audience’s shifting preferences.

Let’s take a closer look at specific skills chess teaches us — ones we can apply directly to D2C marketing programs to maximize their success.

  • Leveraging Strengths: D2C brands must identify the strengths and vulnerabilities of their own position — as well as their competitors’ positions — to make the best decisions and come out on top. Capitalize on the strengths of your brand, as well as on the weaknesses of your competition.

  • Planning and Execution: In chess, you shouldn’t make a move without thinking about the consequences and having a long-term plan of action. “Winging it” simply isn’t a winning strategy. Proactive strategic thinking is essential in D2C marketing as well — both having a long-term plan and following through with it.

  • Positioning for Success: In chess, every game piece has an important role to achieve the end game: checkmate. The same goes with every element of your D2C marketing campaign: all the moving pieces must work together to reach the desired result.

  • Risk vs. Reward: Chess requires a willingness to take risks that take your opponent by surprise. Playing it safe is the surest way to lose the game. Likewise, D2C brands that stick to the status quo are more likely to fail. Understanding which risks will generate greater rewards requires a carefully considered strategic approach.

  • Learning and Refining: It takes years — and many defeats— to become a competitive chess player. In D2C marketing, not every campaign will be a success. The key, as in chess, is to learn from mistakes and losses and continually refine your marketing strategy based on what you’ve learned. That’s where tracking and analyzing data collected from your campaigns really comes into play.

Great chess players have something else in common: a mentor who taught and guided them as they developed, tested, and refined their strategies. D2C brands also stand to benefit from guidance and mentorship provided by an expert who understands the importance of strategic thinking.

At Double Diamond VIP, we’ve been helping clients think and act strategically with their D2C marketing programs for decades. In my own professional journey, as well as with my clients, I continually call back to the years I’ve spent over a chessboard, strategizing my next move. It’s been a pleasure and privilege to share what I’ve learned with peers and clients.

Nick Pietropinto is the founder and CEO of Double Diamond VIP. He can be reached via email at For more, visit


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