The Scaling CEO

In this episode, I speak with Elias Stahl about why a company can’t outgrow its CEO. We dive into leadership maturity, building elite teams, vulnerability as a leadership tool, and how founders must scale themselves as fast as the business. We also explore AI’s role in creativity, manufacturing, and how leaders introduce new technology without breaking trust or culture.

In this episode, I sit down with Trip Adler to explore the tension between customer feedback and CEO vision. We talk about scaling Scribd over 17 years, when listening too closely can stall innovation, and how leaders make visionary leaps when customers can’t see what’s next. We also cover culture design, delegation vs detail, and how AI is reshaping creativity, copyright, and modern companies.

In this episode, I sit down with Greg Schott, former CEO of MuleSoft, to talk about how culture directly affects results as companies grow. We discuss how I should think about building a strong culture at scale, why talent density matters, and how my role as CEO changes as the organization becomes more complex. Greg also shares lessons from scaling an enterprise software company with discipline and focus.

In this episode, I speak with Asher Mathew, CEO of Partnership Leaders, about why growth often breaks once companies reach the $50–80M stage. We discuss when I should start thinking seriously about partnerships, how partners create leverage beyond sales, and how to design a scalable go-to-market strategy. Asher also shares how values, operating models, and AI fit into building a company that can grow sustainably.

In this conversation, I sit down with Kim Hansen, CEO of Cake Equity, to explore why the skills that helped me succeed early may now be limiting my growth as a leader. We talk about self-awareness, letting go of control, and how I should evolve my role as the company scales. Kim also shares how equity and incentives shape behavior and how I can use AI to support better thinking without losing focus.

In this episode, I talk with Ben Borodach, CEO of april, about why chasing fast growth can quietly damage long-term outcomes. We discuss how I should think about building a company in a regulated environment, how to handle pressure from investors, and how to decide when patience matters more than speed. Ben also shares how he uses AI to create leverage and how a CEO’s role must change as the business matures.

In this episode, I talk with Matt Blosl about why companies fail to scale even after hiring great executives. We explore the idea of leadership teams operating as one engine, not silos of functional excellence. Matt shares how CEOs should think about focus during scale, building alignment across product and commercial teams, managing remote organizations, and using AI deliberately rather than chasing hype. This is a deep discussion on execution, leadership design, and sustainable growth.

In this episode, I sit down with Adam Spector to unpack why impatience quietly destroys good strategy. We talk about why founders change direction too early, how many decisions require more time and data than CEOs expect, and why execution compounds when leaders stay focused. Adam also shares hard truths about delegation, outsourcing non-core work, valuing CEO time correctly, and how AI should be used to move faster without distracting from what truly drives growth.

In this conversation, I talk with Brett Sharenow about why most CEOs struggle to clearly explain their business and why that failure blocks both growth and capital. We break down what a compelling case for customers actually is, why investors don’t fund technical explanations, and how clarity drives revenue, valuation, and exits. Brett also shares common CEO blind spots around focus, financial models, scaling discipline, and how AI is reshaping fundraising, competitive moats, and exit planning.

In this episode, I sit down with Ross Wainwright to talk about why AI is no longer optional for CEOs. We unpack what it really means to have an AI agenda, why moving too slowly now creates existential risk, and how leaders should think about AI beyond hype, cost cutting, or automation. Ross also explains the difference between employee experience and customer experience, why leadership vulnerability builds trust at scale, and how speed, experimentation, and breaking silos are critical advantages for CEOs navigating rapid change.