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January 27th, 2026
In the latest episode of our podcast, Demia’s founder and CEO Mat Yarger spoke with Andy Ellwood, founder and CEO of Stretch. Andy is an entrepreneur, father, and technologist whose career has moved through sales, startups, and large-scale data platforms. Now, it centers on one of the most influential yet least transparent systems families interact with every week: grocery pricing.
Groceries shape decisions that feel routine but accumulate quickly. What to buy. Where to shop. What something actually costs. These choices affect household budgets, nutrition, and long-term resilience, yet most families move through the grocery system with very little visibility. Andy’s work explores what changes when that system becomes legible and when people can see the forces shaping their everyday decisions.
Andy’s relationship with money and systems began long before technology. He grew up in a single-income household with four kids, where grocery shopping was never casual. Meals were planned far in advance, waste wasn’t tolerated, and trade-offs were part of daily conversation.
“I didn’t realize it at the time,” Andy recalls, “but my parents were fighting every month to make it work.”
The grocery store became a place where choices had consequences. That experience shaped Andy’s belief that trust starts with clarity – knowing what you’re committing to before you reach the checkout line.
A defining moment came early in Andy’s life when he wanted to rebuild the carburetor on his truck. His father didn’t pretend to know how. Instead, he found someone who did.
“That moment taught me that not knowing isn’t a weakness,” Andy says. “It’s an invitation to learn.”
That mindset became foundational. Andy approaches systems and relationships assuming there’s always more to understand. Rather than projecting certainty, he focuses on asking better questions – a habit that builds trust more reliably than confidence alone.
Before startups, Andy learned resilience in sales. Selling life insurance right out of college meant facing rejection constantly. Rather than treating it as personal failure, he learned to see it as feedback.
“If nobody’s saying no, you’re probably not in the right place,” he explains.
By breaking success into controllable inputs – outreach, conversations, follow-ups – Andy learned to separate identity from outcome. That mental model carried directly into entrepreneurship, where rejection shows up in different forms: customers don’t convert, investors pass, markets shift. Progress, he learned, comes from persistence.
Andy’s time at Gowalla and Waze gave him a firsthand view of how trust compounds in large networks. Waze worked because it made a simple exchange: users contributed small pieces of information and received something more valuable in return.
“If you give one data point,” Andy says, “the system gives you back better guidance than you could get alone.”
Crucially, the feedback loop closed quickly. The benefit was immediate, reinforcing participation. That lesson – that trust requires fast, visible payoff – would later shape Andy’s approach to consumer-facing systems beyond navigation.
Despite all the ways people compare prices – flights, fuel, housing, prescriptions – groceries remained a blind spot.
“We comparison-shop everything except the thing we buy most often,” Andy notes.
That realization led to Basket, a startup designed to show families what their weekly grocery list would cost at different nearby stores. Demand wasn’t the challenge. Data was. Grocery pricing wasn’t built to be transparent, so Basket crowdsourced it, turning everyday shoppers into a distributed data layer.
At its peak, Basket helped hundreds of thousands of families and mapped pricing across tens of thousands of stores. It revealed something important: people wanted visibility. The system simply wasn’t designed to offer it.
Basket didn’t falter because families stopped caring. A series of external shocks – including the sudden loss of a key investor – left the company vulnerable heading into the pandemic. Years later, some of the same investors chose to back Andy again.
“You were honest the whole way through,” one told him.
For Andy, the lesson was clear: outcomes matter, but integrity determines whether trust survives failure.
Stretch is Andy’s return to the same core problem under different conditions. The pandemic forced grocery infrastructure to modernize, making pricing and inventory data accessible in ways it hadn’t been before.
Stretch takes a grocery list – handwritten, typed, or photographed – and shows families what that list will cost at nearby stores before they shop.
“My competition is pen and paper,” Andy says. “If people have clarity before they leave the house, that changes everything.”
Sometimes the priority is saving money. Sometimes it’s saving time. Sometimes it’s simply knowing what’s in stock. Stretch is designed to restore agency, not push people toward a single retailer or outcome.
Andy’s work highlights a broader truth: trust isn’t formed only in policy debates or corporate strategy. It’s built where systems meet real life – in kitchens, shopping lists, and weekly budgets.
When incentives are hidden, individuals absorb the risk. When systems become visible, trust shifts from assumption to informed choice. That principle sits at the heart of Andy’s approach and mirrors a larger movement toward building infrastructures where truth can be observed, verified, and acted upon.
Because trust doesn’t scale through promises. It scales through clarity.
And when everyday systems become understandable, people don’t just save money. They regain agency – the foundation of resilient families, functional markets, and sustainable economies.
🎧 Listen to the full episode of The Future of Trust
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