This Microsoft Marketing Strategy Helped Turn Struggling Startups Into Million-Dollar Businesses

Photo: Valent Lau/Unsplash

Some of the most sage advice that I’ve ever received in life (besides that which came from my parents and other family members) was bestowed upon me not from ancient philosophers like: Aristotle, Plato, and Socrates, but rather from many of the hip-hop artists that I grew up listening to throughout my childhood. 

One particular lesson that I learned from a hip-hop artist (who just happens to be my favorite rapper of all time), didn’t come by way of one of his songs—but rather an interview. Nevertheless, that lesson has gone on to prove extremely valuable for not just me, but also others that listened to the rare interview and utilized the lesson.

Study the greats, until they become great to you no more. For decades, those profound words from the late, great Tupac Shakur have helped myself and others—achieve things that we only imagined were possible. And they could also help your startup do the same. 

What makes Microsoft a great company worth studying?

Throughout the last 23 years,  Forbes’ Global 2000, has ranked the largest public companies in the world based on—sales, profits, assets, and market value. For 2025, Microsoft ranked 9th in the world and 6th in the United States.

Founded in 1975, the now multinational technology conglomerate isn’t just one of the most popular companies on the planet—it is also amongst the most profitable. As of the fiscal year ending June 30, 2025, Microsoft reported record revenues of $281.7 billion. With a net income of over $101.8 billion. 

Who created the strategy? 

Oftentimes some of the most successful marketing strategies are created with just enough audacity—those looking from afar could easily mistake the tactics applied while  executing them as being reckless; due to the risks involved and the unlikelihood of the strategy actually succeeding. 

But truth be told, the vast majority of those marketing strategies only appear to be high-risk. In all actuality, the marketing professionals that devised those crazy strategies—most likely meticulously orchestrated each phase of the strategic process. 

In their book, The Marketing Playbook: Five Battle-Tested Plays for Capturing and Keeping the Lead in Any Market, authors and former leaders of the Microsoft Windows and Office marketing team, John Zagula and Richard Tong, reveal five marketing Microsoft marketing strategies that could help businesses survive and thrive in competitive markets. 

The million-dollar Microsoft marketing strategy 

Although all five marketing strategies detailed in, The Marketing Playbook: Five Battle-Tested Plays for Capturing and Keeping the Lead in Any Market, are great strategies that could help your startup win, if you currently have a small company or a startup, one particular strategy may be of interest to you.

That strategy is called, The Best-of-Both Play.

To successfully execute The Best-of-Both Play, Zagula and Tong instruct marketers to do the following:

•  Identify a key trend that promises to shake up your category.

• Target the current most annoying trade-offs and drive them to the extremes.

• Capture the best of each end while discarding the worst.

• Once you have a real Best-of-Both offering, trumpet it to high heaven. Target one end first and then drive right up the middle. 

Consider trends in your startup’s category that you believe could disrupt the market. Next, identify a pain point consumers are currently experiencing for which other brands in your industry aren’t addressing; and offer a real solution to their problem. Lastly, position your brand as the first and only solution to alleviate your audiences’ issue. 

For a much more comprehensive description of The-Best-of-Both Play, I suggest purchasing a copy of The Marketing Playbook. Not only is the book a great read from a marketer’s standpoint, it also reveals many of the secrets that helped Microsoft become the wildly successful company that it is today. 

By doing so, your startup could study their greatness—until they become great to you no more.

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