In this episode of Crossing the Alameda, hosts A.J. Riebli and Charles Michelet reconnect with fellow Santa Clara University alum Holly Rollo. They discuss Holly's journey from her time at Santa Clara to her current adventures sailing around the world. Holly shares insights on personal growth, the importance of seizing opportunities, and the lessons learned from her career in tech and cybersecurity. The conversation also touches on memorable college experiences, the value of community, and the challenges and triumphs of navigating life changes. In this engaging conversation, Holly Rollo shares her journey through the B2B tech industry, the inspiration behind her business book, and the importance of developing a cohesive go-to-market strategy. She discusses the merging functions of sales, marketing, and customer success, and emphasizes the need for self-discovery and breaking free from self-limiting thoughts. Holly reflects on her sabbatical, the lessons learned from parenting, and her passion for sailing, which she documents on her YouTube channel. The conversation concludes with a fun Fast Five segment, where Holly shares her aspirations and insights on life.