Entrepreneurship in the digital era has undergone significant transformation, offering unprecedented opportunities and posing unique challenges. This paper explores the critical challenges faced by digital entrepreneurs, supported by real-world case studies. It examines issues related to managing digital infrastructure, ensuring cybersecurity, navigating fast-evolving technologies, achieving user acquisition and retention, complying with data privacy regulations, and handling market volatility. By analyzing the experiences of companies such as Slack, Zoom, Netflix, Spotify, Facebook, and cryptocurrency exchanges, this paper provides insights into the complexities of digital entrepreneurship. It emphasizes the importance of strategic management, continuous innovation, and adaptability in overcoming these challenges. The findings highlight that while digital technologies offer vast potential, they also require entrepreneurs to address critical operational, regulatory, and market-related challenges to achieve sustainable success.