Outliers Project

Episode 16: Anurag Gupta – The Difference Engine, more than Redefining Mens Underwear with MyPakage


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Anurag Gupta, CEO of MyPackage and founder of The Difference Engine, lays out a simple idea with big consequences: give people permission to play, then build a company that actually helps them do it. We dig into how MyPackage turned technical design into life-changing men’s underwear, and how the larger mission is to create the best company on earth by serving humans first. Anurag shares the “Hall Pass” ethos, the culture rituals that keep it alive, and why they’re rolling out empowerment programs for employees, retailers, and customers alike. We talk turnarounds, anti-brand thinking, and the discipline of aligning a business to what makes your heart sing. It’s part product story, part manifesto, and a challenge to build companies that leave people more alive.

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Outliers ProjectBy Molly Hawkins

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