In this episode of The Orita Podcast, Aaron Schwartz sits down with two operators who’ve seen inside dozens of Shopify brands: Dov Quint (OpenStore, ran storefronts for ~50 brands) and Caleb Madsen (Fractional CMO). Together they cut through AI hype, agency roulette, and bloated tech stacks to show what really moves the needle.

They discuss:

• Founder obsession is better than shiny tools — why focus beats feature creep every time

• Fractional done right — when to bring in help, when you just need a great media buyer

• “Chaperoning” your stack — how to vet vendors, negotiate, and stop paying for apps you don’t use

• Managed service vs. self-serve — why software still needs humans to unlock value • Practical AI wins — using fewer tools to 1.3x output without 10 new platforms

Plus: Dov explains why you shouldn’t try to learn every AI tool at once, and Caleb makes the surprisingly profitable case for being “boringly excellent” at the basics.

👥 Meet the guests

• Dov Quint — E-commerce operator; Storefronts at OpenStore

• Caleb Madsen — Fractional CMO, Madhouse Consulting

• Host: Aaron Schwartz — Co-founder & CEO, Orita.ai

🎧 Chapters [00:00] Meet the Operators: From Polaroid to 50 Shopify Brands [06:15] From Support Tickets to Ad Spend: Caleb’s Leap to Marketing [09:57] Founder Obsession: The One Moat You Can’t Outsource [15:45] Fractional CMO, Real Talk: When You Need One (and When You Don’t) [21:13] E-commerce Reality Check: What Actually Moves the Needle [26:44] Relationships are greater than Tactics: How “Chaperones” Save Your P&L [27:53] Tech Stack Triage: Cut the Bloat, Keep the Winners [29:22] Tool Picking 101: Vendor Vetting Without the Hype [31:47] Stack Optimization: Turn Subscriptions Into ROI [33:32] Stop the Agency Roulette: Finding Fits That Actually Perform [36:17] AI Without the Buzzwords: One Tool, 30% More Output [44:28] Dear Founders: Simple, Profitable, Boring (Why That Wins) [49:15] The Wrap: Where to Find Dov & Caleb

🌐 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