Twitter (with Dick Costolo)

Twitter’s evolution from an SMS-based service to a global public company turned on critical strategic decisions regarding monetization and platform control. By pioneering the native, feed-based advertising model, the company successfully shifted from data-licensing deals to a scalable business, though it faced persistent challenges in user growth and site stability. A pivotal moment occurred when the company failed to acquire Instagram, a missed opportunity that allowed Facebook to consolidate its dominance in mobile and visual content. Beyond business strategy, the platform struggled to balance its role as a global town square with the complexities of content moderation and political polarization. Ultimately, the company’s trajectory highlights the difficulty of competing against entrenched network effects and the ongoing tension between maintaining an open platform and managing the societal impact of viral, real-time communication.