Ep. 10 - Loyalty, AI Agents, and the Future of Agencies with Rob Domagala of SMILE

Ep. 10 - Loyalty, AI Agents, and the Future of Agencies with Rob Domagala of SMILE

Zak sits down with Rob Domagala of SMILE — the Shopify ecosystem's largest loyalty platform — to talk loyalty mistakes, AI-powered customer agents, and what the agency of the future actually looks like. Zak shares how he used Claude to build a full SMILE + Klaviyo loyalty setup in under 35 minutes, and Rob explains why your agentic tools are only as smart as the loyalty data you feed them. If you're running a D2C brand or an agency and retention is on your radar, this one's for you.

Ep. 9 - From the Gobi Desert to $100M+: How Matt Scanlan Built Naadam on Radical Fairness

Matt Scanlan didn't plan to start a cashmere company. He planned to take a trip around Asia. Instead, he ended up stranded in Mongolia's Gobi Desert for a month with a herder family — no electricity, no running water, no plan — and came back with $2.5M in cash, 60 tons of raw cashmere, and no idea how to turn any of it into a sweater. On this episode, Naadam co-founder Matt Scanlan joins Zak to tell the full story: how a broken supply chain, a life-changing month off the grid, and a willingness to operate on pure naivety built one of DTC's most quietly compelling brands. They also get into AI skepticism from a founder who's looked at the tools and still isn't sold, the real psychology of surviving a decade in consumer, and why Matt says his best business advice is "shut up and listen." If you're building a brand, scaling a DTC business, or just need a reminder that the best founder stories start with someone who had absolutely no idea what they were doing — this one's for you.

Ep. 8 - The AI Secret Nobody's Talking About: Using Your Own Customers to Sell for You

Kendal McMulen, Director of E-Commerce at Global Healing, joins co-hosts Zak and Sam Moorhead (Klaviyo's Director of Customer Growth) for one of the most tactical and honest episodes yet. Kendal built her entire marketing skillset from scratch on a $50/day budget — and now runs one of the most sophisticated AI-driven marketing engines in supplements. She breaks down exactly how her team uses AI across social, dev, and retention (including a tactic where they indexed 28 years of customer reviews to rewrite their product pages using the actual voice of their customers), how to get resistant leadership to buy into AI adoption, and the leadership philosophy — alignment vs. agreement, collaboration vs. communication — that keeps a small team punching well above its weight. Plus: why Zak thinks execution-only agencies have months, not years, before they need to reinvent themselves — and Kendal's take on why AI is there to make you more human, not replace you. Essential listening for DTC operators, retention marketers, and anyone building or leading a high-performance team.

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.