204 Jay Clouse | Always Looking at the Upside

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Here’s the Recap:

Harry Duran welcomes to the podcast entrepreneur, author, and podcast host, Jay Clouse. Jay is the founder of Unreal Collective, a community aimed at helping founders and freelancers achieve their business goals. Jay is the host of Upside, a podcast that examines startup investing outside of Silicon Valley. Upside has conversations with early stage founders from the perspective as if they were angel investors considering the company as an investment opportunity. Harry and Jay talk about the evolution of podcasting, dynamic ad opportunities, and achieving profitability through sponsorship. Finally, Jay discusses the lessons he’s learned as a podcast host and some of the tools that have helped him along the way.

What We Covered:

  • 04:14 – Harry welcomes to the podcast, Jay Clouse
  • 04:46 – How Harry met Jay
  • 06:11 – The inspiration to start the podcast, Upside
  • 08:42 – How Jay attracted guests to his podcast
  • 12:14 – The dynamic of having a co-host
  • 14:17 – Harry and Jay talk about the podcasts that they enjoy
  • 18:28 – The evolution of podcasting
  • 23:54 – Harry talks about his continual passion for podcasting
  • 27:52 – Jay’s prediction for the future of podcasting
  • 32:07 – Harry discusses seasonal podcasts that perform well
  • 35:02 – Jay’s educational background
  • 38:04 – Jay’s current career ventures
  • 39:09 – Jay speaks to Upside’s path to profitability
  • 40:42 – How Jay engages sponsors in conversation
  • 44:42 – Harry expounds on dynamic geotargeted and programmatic ads
  • 50:05 – How Jay has grown and evolved as a podcast host
  • 52:13 – Jay shares how he utilizes the tool, Air Table
  • 55:42 – What is something Jay has changed his mind about recently
  • 1:00:58 – What is the most misunderstood thing about Jay
  • 1:02:04 – Where listeners can follow Jay


Links Mentioned

Jay’s Website

Jay’s Podcast

Jay’s LinkedIn

Jay’s Facebook

Jay’s Twitter – @jayclouse

Jay’s Instagram – @jayclouse

Podcast Movement Website

Link to Upside/Taft Collaboration

Link to Upside/Integrity Power Search Collaboration

Link to Air Table Tool

Podcast Mentioned


The Joe Rogan Experience

Techmeme Ride Home

A Very Fatal Murder

Books Mentioned


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Music Intro by Cedar & Soil: Twitter | Facebook | Website