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Jack Dorsey on Learning from Mistakes and the Importance of Data

Jack Dorsey, co-founder of Twitter and Square, shared a valuable lesson from his early days at Twitter. When asked about his biggest mistake, Dorsey highlighted a critical oversight:

"It was a lack of focus on the data, on the numbers, on what the system was doing, on what the users were doing."

Jack Dorsey
Jack Dorsey

Photo: TED


In the early stages of Twitter, the team didn’t have strong internal dashboards to monitor system performance and user behavior. This absence of data-driven insights led to a lot of speculation. "Speculation creates all this contention and conflict and all these debates," Dorsey explained. Without concrete data, the team was often guessing, which resulted in significant downtime and inefficiencies.


Learning from this, Dorsey took a different approach with Square. "The first thing that I wrote was an admin dashboard that we could see everything that's happening in the business." By prioritizing data and creating comprehensive dashboards, Dorsey ensured that Square could make informed decisions based on real-time insights. This focus on data helped streamline operations and avoid the conflicts and inefficiencies that plagued Twitter in its early days.


Dorsey's emphasis on the importance of data is echoed by other successful entrepreneurs. For instance, Bill Gates, co-founder of Microsoft, once said,

"How you gather, manage, and use information will determine whether you win or lose."

Gates recognized early on that data is a powerful tool for decision-making and strategic planning. His approach helped Microsoft stay ahead of the curve and become a dominant force in the tech industry.


Another compelling example comes from Howard Schultz, the former CEO of Starbucks. Schultz transformed Starbucks from a small coffee bean retailer into a global coffeehouse chain by leveraging data. The company used data analytics to understand customer preferences, optimize store locations, and tailor marketing strategies. Schultz's data-driven approach enabled Starbucks to deliver a personalized customer experience and maintain its competitive edge.


Jack Dorsey's reflections on his early mistake with Twitter underscore a valuable lesson: data is crucial for informed decision-making and business success. By neglecting data, companies risk making misguided choices based on speculation, leading to conflicts and inefficiencies. Embracing data, on the other hand, provides clarity and direction, enabling businesses to navigate challenges effectively.


As Bill Gates and Howard Schultz have demonstrated, leveraging data is a key ingredient in achieving long-term success. Entrepreneurs and business leaders should prioritize data collection and analysis to gain insights into their operations and make strategic decisions. Whether you're running a startup or a well-established company, focusing on data can help you avoid pitfalls and drive growth.


In conclusion, Jack Dorsey's experience highlights the transformative power of data. His shift from speculation to data-driven decision-making at Square serves as a powerful reminder for all entrepreneurs: let data guide your journey. Listen to Dorsey:


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