Ep. 4 - Inside a CMO’s Playbook: Scaling DTC Brands from $5M to $50M+

Ep. 7 - The Email Truth No One Wants to Hear: Why Sending Less Makes You More Money

Aaron Schwartz — Co-Founder & Co-CEO of Orita, former President of Loop Returns, and co-founder of Passport Shipping — joins Zak to challenge everything you think you know about email marketing. Most brands are so focused on converting attention that they've completely forgotten how to capture it. The result is over-emailed lists, tanking deliverability, and customers who've quietly tuned you out. Aaron breaks down why rules-based segmentation is failing brands at scale, how Gmail's ML engineers are working against every sender by default, and why Orita's AI-driven approach to stack-ranking your list daily is the thing retention marketers didn't know they needed. They also get into the AI hype — what's real, what's dangerous, and why getting a great first draft fast might actually be limiting your best ideas. Plus: what the best DTC operators have in common, where direct mail and connected TV are headed, and what's next for Orita. A must-listen for e-commerce brands, retention marketers, and anyone building or working in the Klaviyo ecosystem.

Ep. 6: From Mascot to MarTech: Building a Modern DTC Retention Machine

This episode dives deep into retention marketing with Zach Scheimer, Head of MarTech at Criquet Shirts, and one of the sharpest operators in the Klaviyo ecosystem. From advanced segmentation and personalization to omnichannel lifecycle strategy, Zach shares how to drive more revenue while sending less. If you want to turn retention into a true growth engine, this is your playbook.

Ep. 5: AI, Retention & The Future of Ecommerce with Sam Moorhead from Klaviyo

Zak sits down with Sam Moorhead, Director of Customer Growth at Klaviyo, to break down how AI is rapidly transforming ecommerce marketing, retention, and customer experience. From AI-powered flows and customer agents to lifecycle strategy and micro influencers, this episode is packed with actionable insights brands can implement today. If you want to understand where ecommerce is heading — and how winning brands are staying ahead — this is a conversation you don’t want to miss.

Ep. 4 - Inside a CMO’s Playbook: Scaling DTC Brands from $5M to $50M+

This episode is a DTC growth masterclass with Louis Monoudis, CMO of Artware, breaking down the frameworks behind brands that actually scale. From the “3 C’s” (Cash, Customers, Creative) to emotional storytelling, AI, and team building, Louis shares what separates brands stuck at $10M from those that break through. If you’re a founder, operator, or agency, this is your playbook for smarter growth.

Ep. 3: Live from ShopTalk: The AI Playbook for eCommerce Growth

PODCAST DESCRIPTION Recorded live from ShopTalk, this special episode brings together some of the sharpest minds in ecommerce for a real, unfiltered conversation on what’s actually driving growth today. Joining the panel: * Gina Potenza, Klayvio * Sebastian Brown Glad, clearer.io * Dwayne Doshier, Shopify * Michael Epstein, Post-Pilot From shifting consumer expectations to the realities of retention, lifecycle marketing, and brand differentiation, this group dives into what’s working right now—and what’s not. This isn’t theory—it’s execution. The conversation covers: * How top brands are rethinking retention in a post-iOS, high-CAC world * Where AI is actually making an impact across marketing and operations * The disconnect between data, personalization, and real customer experience * What separates brands that scale from those that stall If you're building, scaling, or optimizing a brand in today’s ecommerce landscape, this is one you don’t want to miss.