Recorded live, this edition of Ugly Talk dives into the real, unpolished side of scaling ecommerce operations with AI — the messy systems, the tool overload, the margin pressure, and the hard tradeoffs that come with growing fast.

Moderated by Manish Chowdhary (Founder & CEO, Cahoot), the panel brings together operators and investors who work at the intersection of logistics, technology, and growth:

Brian O’Connor (CEO, Aevisor Solutions) breaks down how founders can turn operations into a self-funding growth engine by freeing up cash, improving margins, and building systems that scale.

Mat Kaliski (Principal, Acronym Venture Capital) shares how investors evaluate operational discipline, AI adoption, and resilience when backing early-stage ecommerce and technology companies.

Frank Pacheco (Amazon Guru, Nearly Natural) delivers hard-earned lessons from inside Amazon and beyond, revealing how the best brands use AI, data, and logistics strategy to win where “best practices” fall short.

You’ll hear their unfiltered takes on:

• The highest-leverage improvements brands can make in the next 7 and 30 days
• Common scaling mistakes teams repeat — and how to avoid them
• Choosing the right tools without creating costly tech sprawl
• Practical AI workflows for order management, support, merchandising, and reporting
• Simple scorecards to measure speed, accuracy, and cost
• Hiring and vendor decisions that keep operations lean and resilient

If you’re an ecommerce founder, operator, or leader trying to protect margins while scaling smarter, this conversation cuts through the hype and gets into what actually moves the needle.

Want to share your Ugly story?

Visit uglytalk.com/podcast and send us a message.