Eli Weiss (Yotpo, Olipop) and Nate Rosen (Express Checkout) have built followings by writing the kind of honest, insightful newsletters founders and marketers want to read—and in this episode, they bring that same clarity to a live conversation with Aaron Schwartz (Orita).

They get into how the best teams make decisions under pressure, and what writing regularly teaches you about brand voice. Plus: when not to go omnichannel, why repeat purchase rates are rising, and what happens when you scale too fast.

💡 Want to know how to grow without blowing up your brand—or your soul?

👉 Watch for sharp takes on retention, capital constraints, and why your words still matter more than your stack.

👥 Say hi to the guests:

Nate Rosen, Founder & Editor-in-Chief Express Checkout

Eli Weiss, VP Retention Advocacy at Yotpo

🎧 Chapters:[00:00 – From Tariffs to Tweets][06:21 – CX Like You Mean It][13:03 – Retail's Back, Baby][26:27 – “We Just Need a Little Capital…”][30:56 – Growth at What Cost?][32:09 – Running Lean Without Losing Soul][35:21 – Keep the Love Alive][39:37 – Writing Is the Retention Strategy][52:22 – Thinking About Writing?]

🌐 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 Aaron Schwartz, co-founder and co-CEO of Orita. Orita uses machine learning to help brands send smarter, more profitable marketing—by figuring out who actually wants to hear from you and when.If you’ve got a customer list, this show is for you. Whether you’re deep in Klaviyo flows, thinking through supply chain strategy, or just trying to make your paid media budget stretch a little further, we’re here to help you learn from the people building some of the most resilient and resourceful brands and agencies out there.

🔗 Connect with Aaron on LinkedIn https://www.linkedin.com/in/aaroncharlesschwartz/