The Scaling CEO

In this episode, I talk with Damon Lembi about imposter syndrome and why every CEO feels it at some point. Damon walks through his four-step process for beating it, built from his years as an athlete and CEO. We also discuss delegation, building a learning culture, developing leaders at every level, and how AI is reshaping what it means to lead today.

In this episode, I talk with Jim Schleckser about one hard truth: most CEOs are the bottleneck in their own companies. Jim breaks down how to find the real constraint, why great CEOs delegate early, and how to shrink your to-do list so you can focus on what actually drives growth. We also talk about hiring, replacing yourself in key roles, and how AI is changing the work of every leader.

In this episode, I talk with Simon Goodall about why your team sees problems long before you do. Simon shares how frontline insight can transform a company, how leaders create clarity during change, and why every person in an organization is a leader. We also discuss scaling yourself as a CEO and how AI is reshaping operations and customer experience.

In this episode, I talk with Sam Hodges about what founders get wrong as they try to scale. Sam shares why many CEOs fail to grow with the company, how to shift from doing the work to building a machine that can scale, and why honest feedback is so critical. We also talk about the real impact investors have on a business and how AI is reshaping insurance and startup risk.

In this episode, I sit down with Karl Hughes to talk about what it really takes to scale a business when the playbook stops working. Karl shares why Draft.dev grew fast, why it slowed down, and the lessons he learned by going back to the basics. We talk about niching down, staying close to your customers, removing yourself from day-to-day work, and the new pressure AI is putting on every service company.

In this episode, I talk with James Hotson about why most CEOs are stuck at “automation” instead of fixing the real issue—their process. We break down the difference between logic and reasoning in AI, how agentic workflows are changing operations, why customer insight matters more than ever, and what it really takes to scale with speed, clarity, and smarter systems.

In this episode, I sit down with Davide Viola to unpack why CEOs are only as good as the information and insight they get. We dig into value stream mapping, how leaders misunderstand value creation, why discipline and calendar control matter, and how AI is changing what CEOs must see, measure, and fix to scale with clarity.

In this episode, I sit down with Omar Sahyoun, a proven operator who has scaled companies in e-commerce, retail, and technology. Omar explains why short-term thinking kills scale, and why CEOs must treat their business like real operators — focused on revenue, fundamentals, and long-term stability. We also talk about white space opportunities, building teams that follow you for years, and how to grow without burning cash.

In this episode, I sit down with Adam Lieb, a CEO who has been building companies since he was 11 years old. Adam talks about one of the hardest parts of scaling — letting people go sooner. He explains why waiting too long hurts the company, why roles that work at 15 employees don’t work at 50, and how CEOs must keep evolving as the business grows.

In this episode, I sit down with Christophe Zoghbi, the founder and CEO of ZAKA. Chris explains why scaling too fast can destroy a company, and why building the right foundation matters more than speed. We also talk about sustainable growth, the power of community, and how CEOs can use AI to stop being the bottleneck.