The Scaling CEO

In this episode, I sit down with Tom Chavez, founder of super{set}, the startup studio that builds and scales data-driven companies from scratch. Tom has sold companies to Microsoft and Salesforce, generating over 17x returns for investors. We talk about why data isn’t something to process, it’s the main event, how ego can stop CEOs from scaling, and why the best leaders stay curious like kids.

In this episode, I sit down with Avanish Sahai, the executive behind Salesforce’s AppExchange, Google Cloud’s partner ecosystem, and ServiceNow’s explosive growth. We talk about what CEOs often get wrong about scaling, why purpose is the real growth engine, and how AI is changing not just business, but people. He also shares lessons from his work at the Stanford Center on Longevity, exploring the future of work and future of learning.

In this episode, I talk with Jason Baumgarten, Global Head of the CEO and Board Practice at Spencer Stuart, about what it really takes to step into the CEO role. We discuss how to know if it’s the right time, what boards actually look for in top leaders, why self-awareness matters more than ambition, and how technology and AI are redefining what great leadership looks like today.

In this episode, I talk with Joshua Daiter, CEO and co-founder of Inventory, about how he built a lean, product-driven company that uses AI to transform how the wine industry operates. Joshua shares how his team replaced costly manual workflows with AI systems that saved them over a million dollars — while improving accuracy and speed. We also discuss scaling from product to CEO mindset, learning to filter feedback, staying resilient, and keeping your mission strong as you grow.

In this episode, I sit down with Sheldon Fernandez, CEO and AI strategist, to explore how artificial intelligence is transforming leadership and scale. We talk about bias in AI, the ethics behind machine decision-making, explainability, and what happens when technology becomes more powerful than its creators understand. Sheldon also shares his personal journey from technologist to CEO and why the future of scaling may involve billion-dollar companies run by a single person and their AI agents.

In this episode, I talk with Jamie Shanks; a three-time founder who built and scaled Sales for Life and now leads GetLeverage. We discuss how loyalty, poor structure, and doing everything yourself can quietly destroy your business. Jamie shares the lessons behind his biggest failures, why most CEOs overpay for low-value work, and how global talent and AI can rebuild margin and freedom.

In this episode, I sit down with Joshua Fairbairn, CEO of MorphoMFG. We talk about how loyalty can quietly hold back growth and why the people who helped you start your company may not be the ones to help you scale it. Joshua shares lessons from building his business in China, what it takes to maintain quality while growing fast, and the tough decisions every CEO eventually faces.

In this episode, I sit down with Ryan Austin, CEO of Cognota, to talk about why impatience destroys more companies than competition ever could. We discuss the costly mistakes founders make, how to build better leadership alignment, and what it really takes to scale without burning out. Ryan also shares how AI is reshaping the way we run businesses today.

Glenn Gow talks with Sebastien Gendron, CEO and Co-Founder of TransPod, about building a team that can think and act beyond the founder. Sebastien shares how to scale a startup tackling one of the world’s biggest challenges—high-speed transportation—and why true leaders hire people who can solve problems they can’t.

Glenn Gow talks with Julie Szudarek, CEO of Self Financial, about how real leadership means balancing empathy with accountability. Julie shares lessons from scaling companies like Groupon, ATIDA, and Self Financial, leading through chaos, and why hard conversations are the most powerful form of kindness.