Uber's key milestones include its foundation as UberCab in 2009, the launch of its ridesharing service in New York in May 2011, and its national expansion beginning in Chicago in September 2011. By December 2011, Uber had expanded internationally with its launch in Paris. Another significant milestone was in July 2015, when Uber became the most valuable startup in the world.

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Uber's initial investment rounds in 2011 were pivotal for its expansion. The funds allowed Uber to launch its ridesharing service in New York in May 2011, marking the beginning of its national expansion. By September, the service was available in Chicago. The investment also facilitated Uber's international expansion, with the service launching in Paris in December 2011. These expansions were part of Uber's larger goal to become the world's primary transportation marketplace, a goal that required significant investment.

Uber faced several challenges in its goal to become the world's primary transportation marketplace. One of the main challenges was the need for substantial investment to expand its services globally. Additionally, Uber faced regulatory hurdles in many countries and cities where traditional taxi services were well-established. The company also had to deal with issues related to driver compensation and working conditions, which led to protests and legal challenges. Furthermore, Uber had to invest heavily in technology and infrastructure to support its rapidly growing user base.

Uber's expansion strategy played a significant role in its position as the most valuable startup in 2015. The company started as UberCab in 2009 and after initial investment rounds, it began its expansion in 2011. The ridesharing service first went live in New York in May 2011 before national expansion began in September in Chicago. By December, the company had expanded internationally with its launch in Paris. This aggressive expansion strategy allowed Uber to capture a large market share, making it the most valuable startup in the world by July 2015. However, it's important to note that despite its valuation, Uber was not yet profitable as it was investing heavily to become the world's primary transportation marketplace.

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