In this episode of The Journey: In Conversation, Paul Austin-Menear sits down with Jeff Cecil, Founder and CEO of Pull the Shoot, for a wide-ranging discussion on leadership, entrepreneurship, and what it really takes to build organizations that last.
Jeff’s story begins in the early days of enterprise technology. After leaving college early and teaching himself to program, he helped automate banking operations in Chicago before launching one of the internet’s earliest large-scale cloud storage platforms—years before the term “cloud” existed. That venture, FreeDrive, reached tens of millions of users worldwide in the late 1990s, pushing the limits of bandwidth, storage costs, and infrastructure long before hyperscalers or autoscaling were even concepts.
But the heart of this conversation isn’t nostalgia—it’s reflection. Jeff shares what it means to be early, sometimes too early, and why first-mover advantage often comes with hidden costs. He and Paul explore the realities of scaling technology in uncharted territory, the brutal economics of infrastructure in the dot-com era, and the humility that comes from realizing timing matters just as much as vision.
From there, the conversation shifts into Jeff’s second act: leadership development. After decades of consulting, Jeff recognized that operational efficiency alone doesn’t grow companies—people do. Pull the Shoot was born from that realization, inspired by Jeff’s experience skydiving: when everything is moving too fast, leaders need to “pull the chute,” slow down, regain perspective, and work on the business instead of being trapped in it.
Together, Paul and Jeff dig into modern leadership challenges: managing across four generations, the myth that great individual contributors automatically make great managers, and why so many new leaders fail due to lack of training and support. They discuss why appreciation matters more than compensation for retention, how over-control suffocates teams, and why real leadership is about helping others surpass you.
The episode closes with practical stories from Jeff’s coaching work—real examples of emotional reactions derailing leaders, and how clarity, calm communication, and self-awareness can unlock growth. It’s a grounded, experience-driven look at leadership as a human discipline, not a title.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-jeff-sesol
