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!
In this live-recorded edition of the Ugly Talk Podcast at NomadWorks, Times Square in New York City, we hosted an open and honest conversation about how eCommerce brands can pivot in today’s downturn.
Moderated by Manish Chowdhary, founder & CEO of Cahoot, the panel features three founders & strategists digging into how they’re reengineering growth when old tactics no longer work:
Sabir Semerkant (Growth by Sabir) unveils his Rapid 2X Protocol, the model behind $1B+ in revenue across 200+ brands, and warns why many brands won’t survive 2025.
Maya Juchtman (Roswell NYC) blends artistry and performance marketing, sharing how to build brand stories that convert, even when consumer attention is fractured.
London Glorfield (Kickback) talks culture, product, and community: how to launch a youth-forward electronics brand in a time of shrinking attention spans and rising expectations.
🎙️ Expect real talk on:
– What growth tactics are relics now (and need to go)
– Fresh playbooks beyond Meta & Google ads: marketplaces, communities, wholesale, B2B pivots
– How to build resilient unit economics and margin-first growth
– Which experiments are worth backing in a down market
Whether you’re still early in your founder journey or navigating your fifth scaling phase, this episode offers the raw behind-the-scenes of how to build profitable eCommerce when everything else seems broken.

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