In this episode, we sit down with Andy Ellwood, Founder and CEO of Stretch, entrepreneur and technologist building at the intersection of money, data, and everyday decision-making, to explore how trust shows up in one of the most ordinary and consequential parts of life: grocery shopping.
Andy’s perspective on trust was shaped early, growing up in a household where a single grocery trip had to last an entire month. Those checkout lines became lessons in math, tradeoffs, and accountability – lessons that stayed with him as his career moved from selling private jets to helping build early-stage companies like Gowalla and Waze.
The conversation traces Andy’s journey from founding Basket, a crowdsourced grocery pricing app that exposed how dramatically prices can vary within the same city, to his current work at Stretch, where AI and structured data are being used to give families a clearer picture of what their weekly shopping should cost.
Along the way, we explore trust and transparency in everyday systems, how invisible incentives shape consumer behavior, why price opacity persists, and what it means to design technology that genuinely serves families rather than exploits confusion.
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