Failure Is The Price Of Innovation, with Mike Grossman

Your business can be brilliant and still get wiped out by timing, regulation, or a technology shift you saw coming but didn’t act on. Gary Pageau of The Dead PIxels Society sits down with six-time Silicon Valley CEO and author Mike Grossman to talk about the unglamorous reality of entrepreneurship: the wins that arrive late, the pivots that need full commitment, and the failures that happen even when the team does a lot right.

Grossman walks us through early experiences in the tech world, including consulting for Apple in the mid-1980s, then into fintech startups that ran into two classic hazards: adverse selection and legislation that changed the economics overnight. From there, we get tactical about startup survival, including how to read leading indicators like lead quality, pipeline shifts, and revenue direction, plus the mindset shift that saves companies: the business model is not the business. If you cannot adapt, you are not stubborn, you are exposed.

We also zoom out to Silicon Valley culture and today’s AI wave. Grossman explains why failure can be a useful teacher without turning it into a personal brand performance, and we pressure-test AI adoption with a memorable example of hallucinated outputs that look perfect but are totally wrong. The thread running through everything is leadership and people: strong teams, clear focus, and steady decision-making still matter, even in an AI-driven economy where jobs and workflows keep changing.