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.

On this episode of The Cheers Pod, Drew sits down with Ross Adrian Yip, Co-Founder and COO of KICKS CREW—a global sneaker marketplace redefining how emerging brands and retailers connect with the modern consumer.

Ross shares how KICKS CREW has built a platform with over 400,000 unique styles and a business model that works directly with brands and retailers—setting them apart from peer-to-peer giants like GOAT and StockX. He dives into their strategic expansion into key international markets, what it takes to localize for regions like the Middle East, and how athlete partnerships with investors like Damian Lillard, Kyrie Irving, and Austin Reaves are helping drive both culture and commerce.

From his early days building the marketplace to helping launch entire product lines for NBA stars, Ross breaks down what makes KICKS CREW different—and why he believes the future of sneaker commerce is athlete-led, content-driven, and community-first.

If you're building in eCommerce, sports, or content, this one's packed with insight on brand partnerships, go-to-market strategy, and what it means to create a sticky, global marketplace.

In Episode 12, we chat with Aliett Buttelman (Co-Founder of Fazit). Fazit is a beauty brand known for its glitter freckles, which are faux-freckle patches that apply like temporary tattoos. The brand went viral in October 2024 when Taylor Swift wore their glitter freckles to a Kansas City Chiefs game, leading to a 2,500% increase in sales and massive demand. Since then, Fazit has expanded into 1,000 Target stores and 400 CVS locations, projecting $40 million in retail sales.

Aliett shares:

🎤 How Taylor Swift discovered Fazit and how the brand leveraged that buzz to expand its retail presence
💄 The beauty market gap for female sports fans
📈 Tapping into hidden influencers to drive awareness
🏈 Customer-driven product strategy
💸 Using gamification to connect commerce and fandom (and what that actually means)

And more! 

On this episode of The Cheers Pod, Drew sits down with Joe (CEO) and Brett (Co-Founder) of 500 Level, a sports apparel company that has built a merchandise collection licensed by every major sports league or players' association. They dive into how 500 Level grew its impressive licensing portfolio—including the NFLPA, MLBPA, NHLPA, NBA, WNBA, and UFC—and how they’ve mastered the art of capturing sports’ biggest moments on t-shirts, often within 24 hours.

Joe and Brett share their journey from selling shirts outside stadiums to securing nationwide partnerships with the biggest sports retailers and teams in the country. They also offer valuable insights for entrepreneurs on building businesses around passionate fan bases, emphasizing the power of consistency and quality in scaling a trusted platform.

Tune in for a behind-the-scenes look at the sports merch game and why fandom is stronger than ever!

In Episode 10, we chat with Tameka Rish, Senior Vice President of Fan and Associate Experience at Arthur M. Blank Sports and Entertainment (AMB Sports and Entertainment), the parent company of properties including the Atlanta Falcons, Atlanta United, and Mercedes-Benz Stadium. 

Tameka shares her strategies for optimizing fan experience 'driveway to driveway' across multiple properties. She reveals how AMBSE uses data to continuously improve fan experience—from analyzing NFL surveys to using non-sports events, like Taylor Swift concerts, as testing grounds for refining operations.

Tameka also dives into the creative side of fan engagement, discussing integrated themed games such as last year's hip-hop 50th-anniversary celebration featuring 130 artists and never-before-seen performances. 

Celebrating 50 Years of Hip-Hop | Atlanta Falcons:
https://youtu.be/F00xWGia7FI?feature=shared

In Episode 9, we chat with Brian Fagan, a sports and influencer marketing expert. Brian shares his journey founding Oncoor, a sports marketing agency he built and sold, which pivoted to capitalize on the NIL (Name, Image, Likeness) opportunity in college sports. We explore the evolution of NIL, including the rise of collectives and the potential shift towards a revenue share model for college athletes.

Brian discusses his current role at Playbook, a software company for fitness influencers and online coaches in the health and wellness space. He explains how Playbook's technology enables creators to monetize their audience through custom-branded apps and subscription models. We delve into the power of micro-influencers and the importance of volume in influencer marketing campaigns. 

Brian shares insights on identifying successful creators, the benefits of Playbook's unique position in facilitating brand deals, and his predictions for the future of influencer marketing. 

In Episode 8, we chat with Kelly Singh, VP of Marketing at TrophySmack, an e-commerce brands selling customized trophies for fantasy sports leagues and other life events. 

Kelly shares how Trophy Smack is disrupting the trophy industry with high-quality products and by encouraging their audience to celebrate wins (and losses). We explore Trophy Smack's marketing strategies, including leveraging user-generated content and tapping into the fantasy sports calendar. Kelly shares how playing in 30+ fantasy sports leagues help her speak the language of competitors and inform product development. 

Kelly also discusses her involvement with Women of Fantasy Football, an organization providing community and opportunities in fantasy sports and sports media. 

In Episode 7 we chat with Alex Sheinman, Co-Founder of Snapback Agency and Partner at Snapback Sports. We explore both Snapback Sports ascent from a Snapchat account to a full-fledged media company and Snapback Agency's emergence as a force in the industry. 

Alex discusses Snapback Sport's unique relationship with it's audience, driven by content centered around showcasing the fan experience at top sporting events in-person and beyond. Alex also shares how Snapback Agency is helping partners, like the Mall of America, reach the coveted Gen Z demographic by leveraging their roster of sports creators. 

In Episode 6,  we chat with Shane Neman, a serial entrepreneur and investor. Shane shares his journey founding JoonBug a first-of-its kind nightlife events, media, and technology company that he scaled from 0 to $25 million in revenues. We explore how Shane leveraged technology to scale JoonBug and how a commitment to reaching customers with mediums natural to them led to the launch of EZText, an SMS platform that Shane scaled to a customer base of over 50,000 customers including Uber and Home Depot. 

Shane discusses his current focus as an investor and and his barbell thesis focused on investing in leaders in AI as well as physical venues like the Santa Monica pier that bring people closer together. Shane shares his advice to marketers and entrepreneurs on how to find the “lowest common denominator” to connect deeper with their fans. 

Learn more about Shane's lessons learned as an entrepreneur from his book: https://www.nightlifelessons.com/