In this episode of AI First with Adam and Andy, Greg Gottesman of Pioneer Square Labs shares hard-earned lessons from nearly three decades as a venture capitalist, founder, and startup studio operator. Greg explains why startups rarely fail due to product or technology challenges, even in today’s AI-driven landscape, and why cost-effective distribution remains the defining constraint for success.

The conversation explores how AI has dramatically lowered the cost and speed of building products, intensifying competition while making customer acquisition harder than ever. Greg also offers a clear framework for understanding AI-native companies, contrasting isolated AI teams with organizations where every function uses AI as a core capability. He outlines a future where companies move from humans augmented by AI to AI systems doing the work with humans in oversight roles.

For executives and founders navigating AI adoption, this episode provides a grounded perspective on how AI is changing startups, established companies, and the future of work, without hype and with a focus on real business impact.