Entrepreneurship rarely follows a straight line. In this episode of The Journey: In Conversation, I sit down with Steven Werley, founder of Closable.ai, to unpack the winding road that led him from military service to running a marketing agency, to founding a sales agency, and finally into AI-driven sales enablement.
Steven’s story is one of reinvention. After leaving the military, he experimented with coding, web design, and eventually digital marketing. His early years highlight both the opportunities and the insecurity that come with leaving behind a stable career. From local networking in Pennsylvania and Virginia to building funnels and learning from the likes of Neil Patel and Frank Kern, Steven pieced together the knowledge that helped him grow—but also ran headlong into the chaos and uncertainty that so many founders know all too well.
One theme that comes up repeatedly is impostor syndrome—the nagging doubt about whether you really know enough to deliver. Steven shares the tools that helped him cope, including the Alter Ego Effect framework and the practice of stoicism. Together, these gave him the ability to step into different roles with confidence and accept the inevitable ups and downs of entrepreneurship.
We also dive deep into failure. Steven candidly recounts how his sales agency collapsed under the weight of misaligned incentives and client mismanagement, costing him and his partner hundreds of thousands of dollars. Rather than let this end his entrepreneurial journey, he used the experience as fuel to create Closable.ai, a system designed to capture lost revenue, create consistency in sales processes, and act as a force multiplier for sales teams.
Finally, we explore AI’s role in the workplace. Steven makes the case that AI isn’t about replacing humans—it’s about augmenting them. He stresses that people who learn how to use AI effectively will always have opportunities, even as the job market shifts.
This is a conversation filled with practical wisdom: about resilience, failure, adaptation, and the importance of documenting your journey. Steven’s advice to his 2016 self? Create content consistently—it will build authority and open doors.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-steven-werley