"If you wanna have a bestseller, you gotta be a bestseller" with Lou Shipley, author of Unlikely Entrepreneurs
Wed Dec 24 2025
In this episode of The Account Experience Podcast, Adam Dorrell sits down with Lou Shipley — former three-time software CEO, Senior Lecturer at Harvard Business School, board member at CustomerGauge, and author of the new book Unlikely Entrepreneurs, already a top-three Amazon bestseller ahead of launch.
Adam and Lou reflect on more than twenty years of working together, using that shared history to explore what really separates successful B2B companies from the rest. Lou shares key lessons from his book, including why entrepreneurship doesn’t follow a single path — and why experience, judgment, and empathy often matter more than youthful bravado.
A central theme of the conversation is customer and account experience as a leadership signal. Drawing on Lou’s time at Black Duck, they discuss how listening to customers cuts through operational noise, reveals hidden risk, and exposes growth opportunities long before they appear in dashboards or forecasts.
The episode also explores what it’s like to build and lead companies later in life, the advantages of pattern recognition and perspective, and why founders and CEOs should treat customer insight as a strategic asset — not a “soft” metric.
A thoughtful, practical conversation for founders, CEOs, and B2B leaders focused on building trust, resilience, and long-term value.
Find Lou on loushipley.com
More
In this episode of The Account Experience Podcast, Adam Dorrell sits down with Lou Shipley — former three-time software CEO, Senior Lecturer at Harvard Business School, board member at CustomerGauge, and author of the new book Unlikely Entrepreneurs, already a top-three Amazon bestseller ahead of launch. Adam and Lou reflect on more than twenty years of working together, using that shared history to explore what really separates successful B2B companies from the rest. Lou shares key lessons from his book, including why entrepreneurship doesn’t follow a single path — and why experience, judgment, and empathy often matter more than youthful bravado. A central theme of the conversation is customer and account experience as a leadership signal. Drawing on Lou’s time at Black Duck, they discuss how listening to customers cuts through operational noise, reveals hidden risk, and exposes growth opportunities long before they appear in dashboards or forecasts. The episode also explores what it’s like to build and lead companies later in life, the advantages of pattern recognition and perspective, and why founders and CEOs should treat customer insight as a strategic asset — not a “soft” metric. A thoughtful, practical conversation for founders, CEOs, and B2B leaders focused on building trust, resilience, and long-term value. Find Lou on loushipley.com