In this episode of Driving Performance, we sit down with Chris Tiffin—better known as Tiffin—founder of Aisle, the retail growth platform trusted by nearly 750 brands to turn real-world marketing into measurable in-store sales.

Tiffin’s journey starts early. From running a high school landscaping business called *Weed Boys* to thinking he was headed for a finance and investment banking career, entrepreneurship was always close to home—his mother founded RunLites, after all. Everything changed when Supercoffee came to speak at his school. Tiffin slid into the founders’ DMs, landed an internship in 2017, dropped out of school, and quite literally lived on their couch.

At Supercoffee, he ran the online business during a period of hypergrowth—helping scale revenue from $700K to $5M in just one year. But as the brand grew in retail, Tiffin noticed a major blind spot: once products hit store shelves, brands lost visibility into who was buying and why.

That insight became the foundation for Aisle.

We unpack how Tiffin raised capital before Aisle even had a product (including a legendary investor cold email involving a grocery receipt), why early attempts as a consumer-only rewards app nearly burned through $400K, and how a pivot—sparked by Nuggs asking to white-label the technology—set Aisle on its current path.

Today, Aisle powers receipt-verified offers like BOGO and 50% off across more than 200,000 retail locations, pays shoppers back in minutes, and gives brands the data they’ve been missing in brick-and-mortar. Along the way, the company has raised over $5M in venture funding and facilitated more than $20M in rewards to shoppers—helping redefine promotions and loyalty in physical retail.

This conversation is a must-listen for anyone building in CPG, retail media, or consumer tech—and for founders navigating pivots, blind spots, and the realities of scaling fast.