Casey Woo

Scaling is not about working harder — it’s about thinking differently.

In this episode, Keith sat down with Casey Woo, former operator at WeWork, OpenAI, Flexport, and Zappos, founder of Operators Guild, and Managing Partner at FOG Ventures, to break down what it really takes to scale a company.

Casey introduces the concept of the “Scaler” — the operator who thrives in complexity, builds systems that evolve, and helps companies move from chaos to clarity. He shares how the world’s fastest-growing startups fail not because of bad ideas, but because they lack the operating structure needed for sustainable growth.

They dive into:

• Why scaling is a discipline, not a phase
• How great operators think across product, people, and process
• What founders misunderstand about growth- Why systems—not heroics—create durable companies
• How AI is changing the way companies scale

Whether you’re a founder, operator, or investor, this episode is a masterclass in building companies that don’t just grow — they scale.