"I Made a $10M Mistake at Microsoft" (Here’s What Happened)
Tim FerrissPublished on May 12, 2025
Summary authored by editor@wellifi.com
TLDR Summary
Brad Chase, a group product manager at Microsoft, mentored a young product manager, encouraging him to take big risks and pursue innovative ideas. Despite a failed bundling project, Chase's supportive approach highlights the importance of fostering a culture of innovation in organizations.
Key Points
- Brad Chase was a group product manager at Microsoft and a significant mentor.
- The young product manager was encouraged to take risks and pursue big ideas.
- A bundling idea combining software upgrades with 'DOS for Dummies' failed due to pricing issues.
- Chase supported the young product manager after the failure, emphasizing the importance of innovation.
- An effective organizational culture fosters creativity and allows for learning from mistakes.
The Mentorship of Brad Chase: Lessons in Taking Big Swings
In the world of technology and innovation, the impact of mentorship can significantly shape careers and ideas. One such mentor, Brad Chase, played a crucial role in the early career of a young product manager at Microsoft in the early 1990s. This post explores the valuable lessons learned from this mentorship and the importance of fostering a culture of innovation.
Who Was Brad Chase?
Brad Chase was a group product manager at Microsoft, a position that placed him among a small, elite group of talented individuals at the company. At the time, Microsoft was a burgeoning company, employing only around 3,000 people. Chase's leadership and insight helped shape not only the products but also the careers of those who worked under him.
The Early Days at Microsoft
Joining Microsoft in 1991, the young product manager found himself working on MS-DOS 5, a pivotal operating system for the company. His responsibilities included creating packaging, managing manufacturing, and distributing the product to retailers like Egghead Software. This role was foundational for his career development, and Chase's influence was instrumental in guiding him through these early experiences.
The Concept of Taking Big Swings
One of the most significant lessons learned from Brad Chase was the importance of taking risks and pursuing big ideas. Despite being early in his career, the product manager was encouraged by Chase to think outside the box and take bold initiatives. This principle was put to the test when he proposed a unique bundling idea that combined the software upgrade with the bestselling book, "DOS for Dummies."
The Bundling Idea and Its Outcome
The ambitious plan involved distributing the software upgrade alongside the popular book through major bookstores like Barnes & Noble. However, the execution did not go as planned. The bundle was priced too high, leading to a significant loss when it failed to attract buyers. Despite this setback, Chase's response was supportive and forward-thinking.
Lessons in Innovation Culture
In the aftermath of the failed project, Chase emphasized the importance of innovation and encouraged his team to continue pursuing big ideas. His philosophy was clear: organizations should foster an environment where innovation is celebrated, and failures are seen as learning opportunities rather than punishable mistakes. This culture of support is what makes companies like Microsoft thrive.
Conclusion
Brad Chase's mentorship exemplifies the vital role that supportive leadership plays in nurturing creativity and innovation. By encouraging his team to take risks and learn from failures, Chase contributed to a culture that values ideas and growth. As we navigate our careers, the lessons learned from mentors like Brad Chase can guide us in our pursuit of innovation and success.