Sept. 10, 2021

274 Jason DeFillippo - A Brief History of Podcasting

274 Jason DeFillippo - A Brief History of Podcasting

Harry welcomes to the show, professional podcast producer, editor and host, Jason DeFillippo. Jason is the co-host of Grumpy Old Geeks, a no-holds-barred show about the Internet and how it's affecting our lives for good or bad. Since 1994, Jason’s launched hundreds of websites as either a programmer, designer or founder. Almost eight years ago, he pivoted from programming to full time podcast producer, editor, and host.

In this episode, Harry and Jason geek out over the podcast industry, how far they’ve both come as professional podcasters and what the future holds for the medium. Jason opens up about his journey as a podcaster, specifically how he’s honed his hosting skills and what inspired him to start Grumpy Old Geeks. He speaks to the work he did on the Art of Charm, the impact COVID- 19 had on podcast downloads and his feelings on dynamic ads and monetization.




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06:35 – Harry welcomes to the show Jason DeFillippo, who shares his podcast origin story and the impact Tim Ferriss had on his career

17:15 – Jason’s love of technology and the wave of new technology that has emerged

22:25 – The inspiration to start Grumpy Old Geeks and how Jason honed his hosting and producing skills

29:04 – The Art of Charm and what Jason learned about himself throughout his podcasting career

35:47 – The impact COVID-19 had on podcast downloads and monetization

43:05 – Why Jason continues to put out episodes of Grumpy Old Geeks

48:01 – The most misunderstood thing about Jason and something he has changed his mind about recently

51:20 – Jason’s issue with dynamic ads

55:41 – Harry thanks Jason for joining the show and let’s listeners know where they can connect with him




“You can’t do a retake on a Live show. You gotta roll with it, keep the audience engaged and still make a decent show in the end.” (12:58) (Jason)

“Back then it was just get on the mic and try. And then over time, my hosting skills got better and better and better. And now, you put me in front of a microphone I can talk for days. But back then it was a stretch just to even look at the microphone and talk.” (23:59) (Jason)

“Compound questions are terrible when you’re a podcast host. Always remember that!” (27:16) (Jason)

“I hate going to an office. As you can see, I’m in my home right now and I’m never leaving. I did the corporate life for a long time and I never want to do it again.” (35:47) (Jason)




FullCast Website

Podcast Junkies Junkies Facebook Group

Link to Podfest Expo Virtual Summit

Jason’s LinkedIn

Jason’s Website

Jason’s Twitter


Jason’s Podcast:


Grumpy Old Geeks Podcast 


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