In this episode of The Orita Podcast, Aaron Schwartz sits down with Gina Perrelli. Gina learned retention marketing driving a Mini Cooper for Red Bull, where the cans had to be chilled for two hours and could never be dented. That obsession with every touchpoint now runs Stay AI.

• From Red Bull wings team to a Chapter 11 ski resort turnaround, and the consultant from that project who became her co-founder

• Why the Shopify subscription API changed everything: subscription apps stopped being payment processors and became marketing tools

• The breakup analogy for cancellation flows, and why a pre-survey screen is the leg up most brands are skipping

• Why Stay refuses to build loyalty and stays laser focused on being the best at subscription, including the widget-based portal that lets every partner app plug in

• The nine-month data warehouse bet that became Stalien, and the churn question it answered in 30 seconds that would have taken a human hours

• Her hot takes: set up the pre-survey screen, add at least one upsell, and start using Claude before it blows past you

👥 Meet the guest

Gina Perrelli, Co-Founder and CEO at Stay AI

🎙 Hosted by

Aaron Schwartz, Co-Founder and Co-CEO at Orita.ai

🎧 Chapters

[00:00] Gina Perrelli: Aaron's Favorite Thinkfluencer Joins the Pod

[00:45] Red Bull Wings Team: Retention Marketing 101 in a Mini Cooper

[03:42] Chilled Cans and No Ripped Jeans: What Premium Actually Means

[08:19] Turning Down Red Bull, Burning the Suits, Finding the Ski Resort

[09:31] Trial by Fire: Running Retention Through a Chapter 11

[10:23] Meeting Pearson: The Consultant Who Became Her Co-Founder

[12:47] Conned Into Lunar Solar: It's Gonna Be Super Chill

[14:49] NoCommerce: Everything You Shouldn't Do When Spinning Out an App

[17:05] The Shopify Subscription API Moment That Sparked Stay

[18:10] Denied at 3AM: What Gina Got Wrong About Building

[20:28] Why Shopify Plus Is the Only Market That Makes Sense

[22:00] The Series A Deck vs Reality: Saying No to Everything

[25:41] Why Stay Will Never Build Loyalty

[28:19] The Customer Portal Rebuild: Widgets From Every Partner

[29:48] Subscription as a Performance Channel: Two Hours vs 20K on Meta

[31:52] The Breakup Analogy: Pre-Survey Screens and Cancellation Flows

[34:38] The Nine-Month Bet That Became Stalien

[36:45] The Price Increase Question Stalien Answered in 30 Seconds

[40:25] Universal Segments and the Personalized Portal Future

[44:00] Gina's Hot Takes: Pre-Survey Screens, Upsells, and Claude

🌐 Check out Orita.ai for more episodes of The Orita Podcast, where we sit down with the most interesting operators, marketers, and founders in e-commerce to talk about what’s working right now. Hosted by the Orita team. Orita uses machine learning to help brands send smarter, more profitable marketing, by figuring out who actually wants to hear from you and when.

🚀 Get your free email audit from Orita, turn segments into superpowers: https://orita.ai

🎧 Listen on Spotify & Apple

📩 Subscribe for more founder‑grade retention intel