Sept. 19, 2019

204 Jay Clouse - Always Looking at the Upside

204 Jay Clouse - Always Looking at the Upside

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.

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


“I’m kind of a student of interviewing at this point, and the interviewers that I hate are the ones that talk so much.” (13:06)

“If you’re trying to get a slice of that attention from people, the shorter your show, the easier it is for them to stomach.” (21:36)

“You’re giving away the best secret of podcasting, which is that you win just by doing the act and meeting the people. It’s such a phenomenal networking hack.” (26:00)

“I’m a dabbler. I’m a professional dabbler.” (39:06)

“We’re just getting better and better at forming relationships with people in a short period of time.” (51:04)

“Entrepreneurship is a grind.” (59:03)


Focusrite - Makers of my go-to sound card, the Scarlett 2i2

Aweber - Hosts of the Beyond the Podcast Summit


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



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