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 building a personal brand as a founder — the cringe, the doubts, the consistency, and the unexpected wins that come from simply showing up online.
Moderated by Ben Buaron (Founder & CEO, Windmill Growth), the panel brings together two operators who’ve turned content into a growth engine:
Ben Sharf (Co-Founder & Co-CEO, Platter) shares how LinkedIn became his top acquisition channel — driving clients, hires, and even a six-figure inbound investment.
Blaine Davis (Co-Founder, Superconnector; GP at Mute Ventures) breaks down how personal brand powers trust, warm intros, and early-stage momentum — even while staying in stealth.
You’ll hear their unfiltered takes on:
- Overcoming the fear of cringe and publishing anyway
- What authenticity actually looks like online
- How founders convert content into revenue, pipeline, and investor interest
- Balancing top-, mid-, and bottom-of-funnel content
- Why personal brand is becoming non-negotiable in 2025
If you’ve ever wondered whether posting is “worth it,” this conversation pulls back the curtain on how founders really build leverage through content.
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.
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