Dale Dupree: Rebellion, Reflection, and the AI Debate

In this special debrief episode of Make It Happen Mondays, John Barrows sits down with Dale Dupree—founder of The Sales Rebellion and one of the standout voices from the recent Sales Play event in NYC. What starts as a post-event reflection quickly turns into a deep, unfiltered conversation on modern sales, personal transformation, and cultural shifts in the industry.Dale and John unpack the bold themes and subtle symbolism behind Glengarry Glen Ross, from gender and race dynamics to toxic sales archetypes. They also explore why Dale believes we’ve lost the “benefit of the doubt” in society—and why it’s time to bring empathy back into business. They also dive into a spicy moment where Dale called AI a “trend”… and the room nearly exploded.This one is raw, thoughtful, and 100% Rebellion. Buckle up.

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Connect with Dale on LinkedIn: https://www.linkedin.com/in/copierwarrior/

Check out Dale's Websites: crumpledletter.com, thesalesrebellion.com, and copierwarrior.com