Season 2, Ep. 14 | Stretch(ing) Grocery Spend in an AI Era
In this conversation with Andy Ellwood, founder of Stretch, we explore what happens when childhood frugality, serial entrepreneurship, and AI-powered innovation collide around one persistent problem: how to know you are paying the best price for groceries.
Stretch is building the first true shopping intelligence platform, empowering everyday families to compare full basket prices across nearby stores before they shop—saving families over $1,000 a year amid relentless inflation in early results.
Andy takes us from a Texas homeschool experience where grocery runs taught math and ingenuity, through startups acquired by Facebook, Google, and private equity, to the tragedy of losing a key investor days before funding and COVID shuttering his prior venture Basket.com.
Now a new Dad, he reveals how AI supercharges data from 1 million products, personalizes lists for gluten-free needs, and envisions agentic commerce where AI agents negotiate deals for your family while balancing growth with the demands of nurturing a newborn.
We unpack shocking shopper surveys—17% skipping meals, middle-class families adapting hardest—and Andy's "rule of three": automate any task done three times weekly with AI.
This is a story of curiosity asking "what else is possible?", resilience through loss, and tech flipping grocers' info advantage to families. If you battle weekly grocery math, care about AI's practical edge in business and life, or wonder how founders rebound stronger, this is a must-listen on the More Elephant podcast.
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Show Notes
Andy Ellwood is the founder and CEO of Stretch, an AI-powered grocery platform reimagining how families navigate the rising cost and complexity of feeding their households. With a career spanning consumer tech, mobility, coaching, and community-building, Andy has a track record of turning everyday problems into empowering solutions.
A serial entrepreneur behind companies acquired by Facebook and Google, Andy has helped build products used by millions, launched global learning communities, and led teams dedicated to unlocking human potential. His core philosophy—Make Room For Many—shapes how he builds and leads, using technology as a bridge to expand access, clarity, and opportunity.
With Stretch, Andy is tackling one of the most universal challenges Americans face: groceries. By giving families real-time visibility into prices, savings, and smarter choices, he’s building a platform designed to reduce financial stress and return power to everyday consumers.
Andy is a passionate home chef, storyteller, and community catalyst. He lives in New York City with his wife, daughter, and rescue dog.
Key More Elephant Takeaways in this Episode:
Stretch uses AI to deliver real-time basket pricing across thousands of stores, turning mental price comparisons into actionable savings without store-hopping.
Grocery inflation exposes inequities: low-income families already maxed out trade-offs, while 24% of Americans used buy-now-pay-later for food last year.
From crowdsourcing prices at Basket.com to AI querying millions of sku’s, Andy's 12-year obsession solves what Expedia did for travel—now for the unchanged grocery world.
Fatherhood and coaching honed efficiency; AI acts as "smarter interns" for tasks like webpage builds or list tweaks, accelerating Stretch's nationwide rollout.
Agentic AI promises "agentic commerce": your digital rep shops your profile, unlocking demand-based deals from chains competing for baskets.
and more…
More About Stretch: LinkedIn | stretchformore.com | Stretch
App on IOS | Stretch App for Android
Transcript
More Elephant Intro
[00:00:38] Jason Rudman: On this conversation of the More Elephant podcast, I'm excited to talk with Andy Elwood.
Andy is building the first true shopping intelligence platform, as he describes it, a way for everyday families to shop smarter and save real money in an industry that's remained unchanged for far too long. This conversation is going to be a journey from Texas through a number of startups, some tragedy that I think Andy will share redefined, reenergized, and puts him on a path to what he's trying to do now with his company called Stretch.
So Andy, welcome to the More Elephant podcast.
[00:01:18] Andy Ellwood: Thanks so much for having me. I'm excited to be here.
