Only recently have scholars begun to explore the cross-section connection of entrepreneurship and personal selling and introduced the notion of entrepreneurial selling. This study contributes to the emerging debate by addressing the personal selling role of business owners of small and medium-sized enterprises (SMEs) in the business-to-business (B-to-B) market in the context of failure. It examines how business owners make sense of their entrepreneurial selling activities and how underperformance in this role contributes to failure. Based on a literature review and interviews, the paper concludes that entrepreneurial selling is a crucial activity for preventing business failure and one that business owners recognize. Reasons for underperformance include business owners spending too little time on selling, their lack of personal selling skills, and procrastinating their selling activities. Answering the “bird-in-the-hand sales means” questions can produce either success or failure. Future research avenues are then suggested.