Ugly Talk
Ugly Talk
Podcast Description
A Podcast About the UGLY Side of the Entrepreneurial Journey.
Anson Wu & Matthew Jaffe get into conversations with entrepreneurs, who are eager to share their stories, the good ones, the bad ones and especially the ugly ones.
Our podcast resonates with entrepreneurs at all stages of their journey, from aspiring dreamers to established founders. It serves as a voice of shared struggles and triumphs, reminding listeners that entrepreneurial life can be a journey of failure, resilience, and success.
Want to get on the show and share your Ugly stories? Go to uglytalk.com/podcast and send us a message!
Podcast Insights
Content Themes
Explores themes of failure, resilience, and entrepreneurial challenges with episodes showcasing stories of founders like David Kobrosky, who discusses fundraising difficulties, and David Simnick, who shares insights on leadership during crises, aiming to provide listeners with authentic and relatable narratives.
A Podcast About the UGLY Side of the Entrepreneurial Journey.
Anson Wu & Matthew Jaffe get into conversations with entrepreneurs, who are eager to share their stories, the good ones, the bad ones and especially the ugly ones.
Our podcast resonates with entrepreneurs at all stages of their journey, from aspiring dreamers to established founders. It serves as a voice of shared struggles and triumphs, reminding listeners that entrepreneurial life can be a journey of failure, resilience, and success.
Want to get on the show and share your Ugly stories? Go to uglytalk.com/podcast and send us a message!
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.
Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.