The role of mentoring in countering entrepreneurial loneliness, a commonplace problem in the business world, is analyzed in this chapter. It discusses how the entrepreneurial resilience of boosting emotional security, practical advice, and networking opportunities is provided by mentoring. The adoption of mentorship into the digital realm via virtual platforms, matching through AI, and peer-to-peer mentorship are discussed in the chapter. While discussing conflicts such as mismatched expectations and constraints in terms of time, the chapter also throws up the transformational effects that mentorship has on entrepreneurs geared towards helping them through various stages. As the entrepreneurship landscape continues to change, then creating a successful business or individual development, positive mentorship remains a crucial enabler that empowers entrepreneurs to cut across all the complexities of their ventures with confidence.