On this episode of The Cheers Pod, Drew Cousin and Kyle Whittingham sit down with Charlie Shin, Vice President of Analytics and Digital Innovation for the Indianapolis Colts, to unpack how the team built one of the most advanced membership and rewards programs in sports.

Charlie spent 15 years as Vice President of Strategy and Analytics at Major League Soccer before joining the Colts, where he now leads fan data, digital innovation, and commercial analytics.

In this episode, Charlie breaks down the evolution of Colts Connect: why the organization intentionally abandoned the traditional points-based loyalty program model, how they reframed it as a true membership platform, and why dollar denominated currency became the cornerstone of their ecosystem. He explains how shifting from a limited in-stadium rewards system to a 365 day engagement model unlocked participation across every type of fan.

Charlie also shares how the groundbreaking Colts Cash and Fanatics FanCash integration works, what fans experience when converting between currencies, and why the early results show meaningful incremental revenue and deeper data capture. He outlines what comes next, including expanded partner affiliations, more ways for fans to earn and redeem, and a long term vision where Colts Cash becomes useful across everyday life in Indiana.

This episode is a concise masterclass for anyone building in sports, loyalty, or fan commerce.

On this episode of The Cheers Pod, Drew sits down with Shripal Shah, Chief Digital Officer at Next League, to explore the future of fandom, loyalty, and the massive revenue upside hiding in plain sight.

Shripal’s career spans retail, tech, and sports. He’s led strategy and marketing for the Washington Commanders, served as Chief Digital Officer at Shop Your Way—the Sears and Kmart rewards platform—and now advises leagues and teams on how to transform fan engagement with modern digital tools.

He unpacks why so many loyalty programs have failed, how industries like airlines and hotels turned points into billion-dollar assets, and why sports teams are uniquely positioned to unlock similar value. From behavioral rewards that deepen everyday fan engagement to cutting-edge examples like the Cavaliers’ card-linked program with Plaid, Shripal explains how loyalty can drive 8–9 figure revenue lifts while creating stronger sponsor relationships and more personalized fan experiences.

If you’re in sports, eCommerce, or loyalty marketing, this episode offers a masterclass on turning emotion into measurable revenue and why now is the moment to modernize fan engagement.

On this episode of The Cheers Pod, Drew sits down with Justin Anderson, Head of eCommerce and Marketing at FrostBuddy—the fast-growing drinkware brand redefining a category long dominated by industry giants.

Justin shares how FrostBuddy has doubled revenue year-over-year by pairing a best-in-class product lineup with a relentless content engine that produces dozens of TikTok, Meta, and Snapchat posts each week. He reveals how the brand seizes cultural moments—from Shark Week to viral design drops—and why licensing deals with the MLB, NHL, and top college programs have become a major growth driver.

From launching a gamified college basketball campaign that boosted AOV by nearly 35% to rolling out a season-long “Game of the Week” program with Cheers Cash for college football, Justin breaks down how FrostBuddy combines sports marketing, gamified loyalty, and rapid product development to keep fans engaged and sales climbing.

If you’re building in eCommerce or selling licensed products, this episode is packed with insight on content strategy, product innovation, and how to win big as a challenger brand.