Ugly Talk Podcast by Ugly Talk

Episodes 8

Avg. Duration 53m

Activity Highly Active

Apple Rating ★ 5.0 (4)

Since Dec 2024

Latest Episode May 2026

Outreach Signals

Features Guests

Publishing Details

Schedule

Every 2 Months

Format

Episodic

Consistency

49%

Hosting

feed.pod.co

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About This Podcast

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!

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Recent Episodes

UGLY TALK: BUILDING AND SCALING TECH COMPANIES IN MIAMI

May 07, 2026 1h 6m

Recorded live at Mana Tech in downtown Miami, this edition of Ugly Talk pulls back the curtain on the Florida tech boom. While the city is often celebrated for its energy, the panel explores the…

UGLY TALK: FOOD & BEV FOUNDERS 2025 LESSONS AND 2026 PREDICTIONS

Feb 11, 2026 47m

Recorded live at The Yard in Herald Square, this edition of Ugly Talk dives into the unpolished reality of building and scaling a food and beverage brand in 2025. This isn't about the highlights—it's…

Ugly Talk Live: Leveraging AI to Optimize Ecommerce Logistics and Profits

Jan 14, 2026 1h 8m

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…

Ugly Talk Live: Building Effective Personal Brand for Founders.

Dec 03, 2025 32m

Recorded live, this edition of Ugly Talk dives into the real, unpolished side of building a personal brand as a founder — the cringe, the doubts, the consistency, and the unexpected wins that come…

Ugly Talk Live: Building Profitable eCommerce in a Downward Market

Oct 15, 2025 1h 15m

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…

Sevak Avakians from Intelligent Artifacts

Mar 11, 2025 53m

In this episode of Ugly Talk Podcast, Anson and Matthew chat with Sevak Avakians, an AI pioneer who built one of the first artificial intelligence models back in 2008. Sevak shares his journey of…

David Kobrosky from IntrosAI

Jan 13, 2025 51m

In this episode of Ugly Talk Podcast, Anson and Matthew chat with David Kobrosky, founder of Intros AI, a platform revolutionizing how communities connect. David shares his story, from a…

David Simnick from Soapbox

Dec 10, 2024 29m

In this episode of Ugly Talk Podcast, Anson and Matthew chat with David Simnick, the founder of Soapbox Soaps. David shares the gritty reality of building a mission-driven brand, including his…