Gregory Day of the Weekly Portland Podcast Offers an Education in Entrepreneurial Pursuit

When asked why he started his podcast — the Weekly Portland Podcast — Gregory Day jokes that narcissism may have played a factor. He goes on to say that it might have been the desire to “produce a show that people actually want to listen to.”

The Manchester, England native points to a line he thinks might have been quoted in a Chuck Palahniuk book, “everyone has three lives,” as he explains his top passions. By day he manages the archives at Pendleton Woolen Mills — a job that’s not unlike podcasting because both involve scrounging up the details of people in podcasting’s case and centennials-old artifacts in Pendleton’s case. For ten years he’s worked with authors, getting references, and maintaining the artifacts of the worldwide phenomenon that is Pendleton. “It’s a big deal in Eastern Europe and Asia,” he says. “Everyone loves the American cowboy.”

As we run down Gregory’s passions — which have interestingly manifested into new roles that have been created for him — you might notice Gregory has more than three lives. But no one accused me of being good at math so who’s counting.

Reporter of “The Dish” for KPTV’s “More GDO”

Once-a-week, he swings downtown on his lunch break to film “The Dish,” an entertainment segment he hosts on the mid-morning show after KPTV’s early-morning show, “Good Day Oregon (GDO),” aptly named “More GDO,” airing at 9 a.m. on weekdays. Gregory’s two-and-a-half-minute segment offers the dish on five to six cool events happening in town.

The opportunity came about when the show had Gregory on to talk about his podcast. He then interviewed “More GDO” host, Stephanie Kralevich, on his podcast and a relationship was formed.

Gregory’s work on “The Dish” includes more than just filming each segment. He also selects the highlighted events and writes the “bits.” Gregory warns that the editors may cut an event out of his pre-recorded lineup. This is why he says that it’s important to send a video of each event, confiding that he’s been surprised by how many PR people do not have access to video. I interjected that people might not understand that they actually do have video — you don’t need to be worried if the video is too overly-marketed nor too rough — they just use a few seconds of each video on “The Dish” so anything that is streaming or on YouTube will do. Try shooting something on your iPhone and see what happens!

PR people should send pitches for both “The Dish” and the Weekly Portland Podcast to Gregory at: [email protected].

Showrunner of The Weekly Portland Podcast

Gregory started the Weekly Portland Podcast about two years ago for reasons that have morphed over time. It first began on YouTube with videos as he didn’t really listen to podcasts. But he eventually realized that podcasting was the best format to truly capture the essence of the person being interviewed. He wanted to portray the interesting people of Portland in a non-comedic way that remained light-hearted and professional.

“It’s a great excuse to stick your nose in a lot of offices. When would you meet these people? Adults rarely sit down together for an hour without a purpose,” Gregory adds to his podcasting evolution story.

Today, Gregory’s podcast “why” is about education. The amount of knowledge he’s secured from the people gracing his podcast, and the many others Gregory listens to, has brought him to realize that learning is his true passion.

The qualifier to get on his podcast is simple — Gregory wants to talk to local people doing really interesting things.

Organizer of Audiobook Club PDX

Gregory’s inner student is also being fed by his audiobook addiction. He rips through about two per week. That’s why he decided to start a book club that exclusively discusses audiobooks. Audio Book Club PDX meets the first Monday of each month at The Nines Hotel. It’s an open meetup format that anyone can join to discuss reviews, recommendations, and commentary. On December 4th they will be talking all about the Sci-Fi genre.

His passion for audiobooks is bringing another entrepreneurial idea his way: to write an audiobook by voice. “But we all want to do something,” Gregory quickly dismisses as I try to dig deeper into this fascinating idea.

Entrepreneur of Ideas

Gregory is an entrepreneur through and through. He may be employed at Pendleton, but over the course of the conservation I recognized the entrepreneurial spirit running through his veins. Not only are all of the side-gigs he’s started entrepreneurial, he actually was in business for himself as an art dealer in Portland before working with Pendleton.

And if starting a podcast, audiobook club and securing an ongoing segment on Fox for yourself aren’t entrepreneurial enough, a hunch tells me that someday his future may be pointed toward starting another company — this time focusing on his educational pursuits. He imagines a world in which education is delivered to us at the touch of a button specifically customized to our interests. “It’s like Uber for education,” Gregory explains.

Gregory, we are excited to find out what else we’re going to learn from your entrepreneurial ventures because we’re already learning so much from your work today.

Show Notes:

Gregory Day is the producer and host of The Weekly Portland Podcast, and The Dish on KPTV’s More Good Day Oregon. In his show, The Weekly Portland Podcast Gregory features TED speakers, creatives, industry leaders & entrepreneurs.

In this episode of PR Talk, Amy and Gregory talk about podcasting as Gregory shares its importance and how listening to a podcast becomes a tool to continuously learn and build up knowledge. He also shares tips and advice on how to PR consultants can take advantage of the growing podcast platform. 

Check out these episode highlights:

03:00   Gregory shares how and why he started The Weekly Portland Podcast

04:25   Gregory’s transition journey from YouTube videos to a podcast

08:08   Gregory’s work history

09:31   How The Weekly Portland Podcast helps grow Portland’s publicity

10:36   Podcast as a learning tool to build knowledge

12:23   Reasons for success for a podcast that is about creator’s passion and interest

14:16   Gregory on booking and qualifying his podcast guests

25:13   His life’s journey: struggles and successes moving from England to the United States

28:31   Gregory’s top tips for PR people on setting up their Podcast shows and how they can take advantage of the growing platform

40:49   Importance of persistence according to Gregory

About the guest: Gregory Day

Host of KPTV 12’s “The Dish” on More Good Day Oregon, Showrunner at The Weekly Portland Podcast. Billed as “The NW Fresh Air,” The Weekly Portland Podcast is hosted by Gregory Day featuring TED speakers, creatives, industry leaders & entrepreneurs. New shows every Monday.

Connect and follow Gregory on social media:

This episode of PR Talk is brought to you by PRSA Oregon

Throughout Oregon and Southwest Washington, PRSA provides members with networking, mentorship, skill building and professional development opportunities – whether you are a new professional fresh out of college or a skilled expert with 20 years in the industry. Check out PRSAoregon.org for more information on how membership can help you grow and connect.

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Amy Rosenberg
Founder and President at Veracity
Writer. Podcaster. Press Friend. Hand Holder.