The Sachin and Adam Show

The Unlikely Pair: $2B Cloud Exit, Reshaping AI Ads, Competing with Thiel, Backing Human Creativity

May 20, 2025
Jack White, Co-founder of Cuttable with a rich creative background in advertising, teams up with Sam Krindenberg, who sold A Cloud Guru for $2B. They discuss how their contrasting experiences shape their approach to AI-driven advertising. Jack shares poignant advice from his father, while Sam’s journey from risk-averse beginnings to tech success unfolds. The duo explores why most AI ads fall flat and their mission to elevate creativity, believing human artistry remains crucial even in an AI-saturated market.
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ANECDOTE

Childhood's Lesson in Humility

  • Sam Krindenberg described a volatile childhood with an entrepreneurial father whose businesses often crashed.
  • This experience taught Sam to be humble, risk-tolerant, and not to get too above himself, preparing him for startup ups and downs.
ANECDOTE

Father's Game-Changing Advice

  • Jack White shared his father's advice from childhood: "Life's there for the taking, mate, you got to go and do it."
  • This advice shaped Jack's approach to taking initiative and going after what he wants in life and business.
INSIGHT

Craftsmanship Gains Value

  • As content creation becomes easier, the value of content decreases, but craftsmanship rises in importance.
  • Rare humans who excel in creative craft will become more valuable as digital advertising shifts.
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