Crossing Borders, Cracking Logistics: Inside the Shipping Wars
Fri Feb 06 2026
In this episode of The Orita Podcast, Aaron Schwartz sits down with Alex Yancher, Co-Founder & CEO of Passport, to go deep on the part of ecommerce most people underestimate until it breaks: international expansion.
Alex has seen it all...investment banking during the financial crisis, early Facebook, building and selling companies, and then spending the last decade living in the messy reality of cross-border logistics. He shares what it really takes to help brands unlock global growth, why Passport leaned into M&A as a strategic weapon, and how the next wave of commerce will be defined by who can move fast across operations, regulation, and customer experience.
Together, they dive into:
• Alex’s path from Morgan Stanley to Facebook to entrepreneurship
• The early “warehouse in Delaware” era that taught him cross-border the hard way
• Why Passport made two key acquisitions and how to integrate without breaking the org
• When brands should stay cross-border vs. go in-country with local inventory
• The hidden complexity: importer of record, compliance, taxes, labeling, and marketplaces
• Why TikTok Shop and marketplace rules are forcing new global playbooks
• How Passport reduces “Where’s my package?” pain by owning the tracking and support layer
• What AI is changing inside Passport from call recording culture to semantic search and analytics
• Why international is a growth lever and a risk hedge for brands too dependent on the US
👥 Meet the guestAlex Yancher, Co-Founder & CEO at Passport
🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai
🎧 Chapters
[00:00] Meet Alex Yancher: The “Build + Buy” Playbook Behind Passport[05:40] From Wall Street to Startups: The Skills That Still Pay Off[09:54] Why Most Founders Ignore M&A (And Why Alex Didn’t)[15:32] How to Buy Companies Without Breaking Yours: Lessons From the Trenches[20:11] Going In-Country: The Hidden Mess Behind “Local Fulfillment”[25:33] When You Become the Buyer Everyone Calls: Passport’s M&A Flywheel[31:57] Why Brands Pick Passport: The Real Differentiator (It’s Not Just Shipping)[38:39] How Passport Uses AI: Internal Leverage, Faster Decisions, Better Ops[44:09] Scaling to 230 People: CEO Lessons, Bottlenecks, and Staying Aligned
🌐 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
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In this episode of The Orita Podcast, Aaron Schwartz sits down with Alex Yancher, Co-Founder & CEO of Passport, to go deep on the part of ecommerce most people underestimate until it breaks: international expansion. Alex has seen it all...investment banking during the financial crisis, early Facebook, building and selling companies, and then spending the last decade living in the messy reality of cross-border logistics. He shares what it really takes to help brands unlock global growth, why Passport leaned into M&A as a strategic weapon, and how the next wave of commerce will be defined by who can move fast across operations, regulation, and customer experience. Together, they dive into: • Alex’s path from Morgan Stanley to Facebook to entrepreneurship • The early “warehouse in Delaware” era that taught him cross-border the hard way • Why Passport made two key acquisitions and how to integrate without breaking the org • When brands should stay cross-border vs. go in-country with local inventory • The hidden complexity: importer of record, compliance, taxes, labeling, and marketplaces • Why TikTok Shop and marketplace rules are forcing new global playbooks • How Passport reduces “Where’s my package?” pain by owning the tracking and support layer • What AI is changing inside Passport from call recording culture to semantic search and analytics • Why international is a growth lever and a risk hedge for brands too dependent on the US 👥 Meet the guestAlex Yancher, Co-Founder & CEO at Passport 🎙 Hosted byAaron Schwartz, Co-Founder & Co-CEO at Orita.ai 🎧 Chapters [00:00] Meet Alex Yancher: The “Build + Buy” Playbook Behind Passport[05:40] From Wall Street to Startups: The Skills That Still Pay Off[09:54] Why Most Founders Ignore M&A (And Why Alex Didn’t)[15:32] How to Buy Companies Without Breaking Yours: Lessons From the Trenches[20:11] Going In-Country: The Hidden Mess Behind “Local Fulfillment”[25:33] When You Become the Buyer Everyone Calls: Passport’s M&A Flywheel[31:57] Why Brands Pick Passport: The Real Differentiator (It’s Not Just Shipping)[38:39] How Passport Uses AI: Internal Leverage, Faster Decisions, Better Ops[44:09] Scaling to 230 People: CEO Lessons, Bottlenecks, and Staying Aligned 🌐 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