Best Jason DeFillippo Podcasts (2025)

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714: Crossfade This 1:22:31

Play Pause

5d ago1:22:31

1:22:31

The internet continues its chaotic march, with a TikTok deal potentially happening (for real this time, maybe), while LimeWire bought the Fyre Fest brand, because more viruses are always a great idea. Corporate America is going full AI-bro with massive layoffs at Fiverr, xAI, and Google, while OpenAI reveals people are using ChatGPT for pretty much…

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713: Ourovibeos 1:22:37

12d ago1:22:37

1:22:37

This week on Grumpy Old Geeks, we're diving headfirst into the digital dumpster fire, starting with follow-up that will make you wonder if the rich are finally getting their comeuppance. It seems Tesla's market share is plummeting, and Elon Musk has been unceremoniously knocked off as the world's wealthiest person. Meanwhile, OpenAI and Microsoft a…

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712: Preparation WTF 1:12:39

19d ago1:12:39

1:12:39

The internet's still broken, folks, and apparently, AI's here to make it more awkward. Intel caught a break from Uncle Sam's CHIPS Act, cool for them, not so much for those 'flashing warning signs' in the job market. Meta's been letting celebrity chatbots run wild (and creepy), Midjourney's getting sued by Warner Bros. for stealing IP (who'da thoug…

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711: Oh Thank Heaven 44:45

26d ago44:45

44:45

Remember when we thought AI was going to bring about utopia or Skynet? Turns out, it's mostly just a bunch of fancy spreadsheets, a potential bubble ready to burst (looking at you, Nvidia), and a legal minefield. We're talking wrongful death lawsuits because a chatbot encouraged suicide, OpenAI admitting their 'safety controls degrade,' and then se…

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710: Mass Delusion Events 1:17:08

1M ago1:17:08

1:17:08

Remember all that "AI is gonna change everything" nonsense the kids were screaming about just a few months ago? Yeah, about that. It turns out 95% of corporate generative AI pilots are, to use a technical term, completely shitting the bed, according to a report from MIT. This shocking revelation has sent Wall Street into a tizzy, wiping trillions o…

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709: Grumpy Old Gardeners 1:12:09

1M ago1:12:09

1:12:09

Well, strap in, because this week the tech world decided to set itself on fire just for kicks. First up, Elon Musk’s much-hyped Tesla Diner in Los Angeles is already a culinary disaster, slashing its menu faster than you can say “over-promise and under-deliver.” Speaking of rolling garbage fires, the Cybertruck now apparently sounds like Fred Sanfo…

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708: Spicy Mode 1:08:50

2M ago1:08:50

1:08:50

Alright, buckle up, buttercups, because this week's "Spicy Mode" episode of Grumpy Old Geeks proves that while things change, they mostly stay the same—just with more AI and less common sense. First up in FOLLOW UP, some poor schmoe automaker actually got a federal exemption for automated vehicles. Because what could possibly go wrong when we let r…

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707: Someone Spilled the Tea 43:55

2M ago43:55

43:55

While Brian frolics somewhere in the Pacific Northwest, Jason brings in cyber-sleuth Dave Bittner for a jam-packed episode covering everything from Gen X’s slow descent into obscurity to furries, feds, and face-scanning your way into porn. The guys start with a salute to the late, great Tom Lehrer—a math nerd with a piano and zero tolerance for BS—…

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706: Let There Be Scams 1:07:24

2M ago1:07:24

1:07:24

This week, we're drowning in the genius of our tech overlords as Elon Musk opens his Tesla diner, complete with $17 hotdogs and a blocked apartment view, while his $9 billion Neuralink startup claims it’s a "disadvantaged" business. Not to be outdone, SpaceX is mad about other people's space junk, France is criminally probing X for algorithm manipu…

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705: Vibe Defunding 1:22:02

2M ago1:22:02

1:22:02

Kicking things off, Jack Dorsey—a man with too much time on his hands—has vibe-coded his beard into an insecure messaging app that the company admits you shouldn't trust... yet. Meanwhile, if you want a piece of a legendary disaster, the Fyre Festival brand sold for a mere $245k after some shady bidding that might be a "shitty agentic AI" at work. …

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dropping the great burden | Zen teacher, Valerie Forstman 1:28:48

2M ago1:28:48

1:28:48

What happens when a world-class musician trades the pursuit of perfection for the practice of letting go? Valerie Frostman spent 20 years in classical music's pressure cooker before a personal shift sent her to a Zen center. What she discovered there—through experiences that defy ordinary description—transformed not just her relationship to perform…

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704: I’m Lovin’ It 1:22:19

2M ago1:22:19

1:22:19

Apparently, you can’t keep a good grifter down, as Billy McFarland’s seven-figure Fyre Fest deal collapsed, so he’s hawking the brand on eBay like a box of junk. Meanwhile, Indeed and Glassdoor are laying off over 1,000 workers, probably to pay for the AI that’s jacking up our electric bills. Speaking of AI, a Tesla robotaxi crashed itself while El…

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703: None More Black 1:16:43

3M ago1:16:43

1:16:43

This week, we saddle up for another bumpy ride through the dystopian tech clown show. We kick off with the surveillance state’s greatest hits: ICE raids sweeping L.A., a website literally called FuckLAPD.com that lets you ID cops by their mug shots, and a Norwegian tourist who learned the hard way that having a JD Vance chipmunk meme on your phone …

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our journey with alcohol | Jason DeFillippo 1:31:01

3M ago1:31:01

1:31:01

In this deeply personal and unflinchingly honest episode, Kevin sits down with his friend of over two decades, Jason DeFilippo, to explore a journey that has defined much of their lives: their relationship with alcohol. Their friendship, like many, was forged over countless pints and late-night conversations. Jason shares his harrowing story of a n…

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702: TikTaco 1:24:51

3M ago1:24:51

1:24:51

In this week’s episode, Trump delays the TikTok ban for the third time—because procrastination is the new policy—and Twitter’s old sign finds new purpose as desert firewood. Tesla continues its streak of “hold my beer” engineering by blowing past a school bus in FSD tests, then mysteriously dumps Cybertrucks in Jersey parking lots while prepping a …

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for the love of play | Jason Fried 1:02:35

3M ago1:02:35

1:02:35

Today, we're joined by Jason Fried, the co-founder of 37signals, the company behind groundbreaking tools like Basecamp and HEY, and the co-author of influential books like Rework. Jason is the quintessential authentic builder, someone who has spent over 25 years forging his own path, guided by a philosophy that often runs counter to the hustle cult…

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701: Dancing in the Streets 1:18:19

3M ago1:18:19

1:18:19

This week, we light a candle for lost legends and torch a few bad takes. In Follow Up, Molly White reminds us that giving a damn still matters—despite the rising tide of apathy (and flaming robotaxis in downtown L.A.). Protesters across the country chant “No Kings!” while Elon does his best impression of a bootlicker groveling back to Trump. Meanwh…

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18 - From Coldplay to Core Values: A Schmactors Redemption Arc 40:16

3M ago40:16

40:16

In this episode of Schmactors, James and Mark crack open a fresh six-pack of emotional baggage and Red Bull to revisit James’ Buffy-era fitness routine—spoiler alert: it involved starvation, rollerblading disasters, and enough sugar to trigger a Canadian health minister. But it doesn’t stop there. The guys detour into tragic photography gigs, baby …

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700: Going Antiquing 1:19:28

4M ago1:19:28

1:19:28

On this week’s episode of Grumpy Old Geeks, we kick things off with the glorious meltdown of two of our least favorite Bond villains: Elon Musk and Donald Trump. Not only is their public pissing match tanking Tesla’s market cap, but now Trump’s launching a crypto wallet to… fund freedom? Or at least funnel it straight to his latest shell game. Mean…

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17 - Stage Fright, Buffy Reboot Buzz, and Velveeta Confessions 40:22

4M ago40:22

40:22

In this wildly emotional and hilariously revealing episode, James Marsters returns from the convention circuit with juicy Buffy reboot rumors (which he can't actually talk about). Meanwhile, Mark Devine contemplates the delicate art of crying (spoiler: he struggles) and reminisces about his eyebrow-raising appearance on Sex and the City. James refl…

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699: TACO 2025 1:17:31

4M ago1:17:31

1:17:31

In this week’s “we told you so” edition, we kick things off with the latest AI faceplant—go ahead, Google “Is it 2025?” and try not to spit coffee on your keyboard. Meanwhile, over at Meta, Zuckerberg’s brilliant idea to loosen content moderation has, shocker, led to more harassment and violent content. Elsewhere in tech dystopia: Texas is trying t…

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16 - Adrenochrome, Hollywood Hell Parties, and The Beatles 46:49

4M ago46:49

46:49

This week on Schmactors, it’s time to zap into the void with a cattle prod, question your Beatle loyalty, and wonder aloud if David Caruso is still standing under that same damn porch light. Mark recounts the surreal politics of Hollywood parties (spoiler: Caruso smokes cigars like he’s in a noir), while James waxes philosophical about the dangers …

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698: Watch Out for That Tree! 1:20:32

4M ago1:20:32

1:20:32

This week, we kick things off with the return of Space Karen’s meltdown tour: Elon Musk got flustered in an interview, sputtered out one-word answers, and called the journalist an “NPC,” which is rich coming from the guy whose only real upgrade since PayPal is yelling “freedom” in meme fonts. Meanwhile, 23andMe sold your DNA to Regeneron at a bankr…

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15 - Stage Kisses, Broken Noses, and the Ophthalmologist Conundrum 41:06

4M ago41:06

41:06

In this episode of Schmactors, James and Mark go from superhero vision exams to existential midlife meltdowns in under 40 minutes. First up: can Clark Kent’s ophthalmologist really be fooled by a pair of glasses? The guys spiral into Superman’s colonoscopy cover stories, locker room etiquette, and how lying to protect a secret identity might actual…

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697: Office of Defects 1:17:16

4M ago1:17:16

1:17:16

This week on Grumpy Old Geeks: FOLLOW UP kicks off with Manus madness, a $2 million ticket to Trump’s crypto cash-grab, and Elon’s Boring Company worming its way into an $8 billion Amtrak boondoggle. Meanwhile, CryptoPunks gets handed off to a nonprofit like an expired Groupon—proof the NFT hype cycle ends with a 501(c)(3) and a shrug. IN THE NEWS,…

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14 – Method Madness, Brass Knuckles, and Time Machines 40:08

4M ago40:08

40:08

This week on Schmactors, James and Mark dive into the psychological side effects of method acting, accidental hate-symbol cosplay, and the crushing guilt of being slightly less generous than your saint-like friends. From dialysis dinner duty to Doc Martens and flannel misfires, it’s a journey into the absurdity of good intentions and the existentia…

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13 - Deathbed Lies, Piano Dreams, and Climate Crimes 53:36

5M ago53:36

53:36

In this wildly unpredictable episode of Schmactors, James Marsters and Mark Devine dive headfirst into the philosophical, the musical, and the deeply absurd. From pondering whether Patrick Mahomes is the Mozart of football or just another heartbreak waiting to happen, to deathbed confessions involving DB Cooper, Madonna, and… fake buried treasure, …

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696: Googliearchs 1:25:03

5M ago1:25:03

1:25:03

In this episode of Grumpy Old Geeks, we’re serving up a buffet of dystopia with a side of snark. First, Kuwait has finally realized crypto bros are an energy drain, not a feature. Celsius Network’s founder gets 12 years for running a “safe investment” Ponzi scheme. And in Lopez v. Apple, we find yet another reason to question Cupertino’s moral comp…

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12 - Galaxies, Groupies, and the $30 Sandwich 33:42

5M ago33:42

33:42

In this episode of Schmactors, James Marsters and Mark Devine catch up on travel tales, revisit brushes with fame, and plunge headfirst into the black hole of existential curiosity. From James’ sticker-shock in Australia (turns out the $30 sandwich isn’t quite what it seems) to Mark’s brush with Sex and the City fame (and the ensuing emotional brea…

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695: Mad Hatter 1:10:16

5M ago1:10:16

1:10:16

In this episode of Grumpy Old Geeks—Mad Hatter edition—we kick things off with a refresher on Staingate and the joys of delamination (spoiler: it’s not a spa treatment). Then we dive into the U.S. government’s latest tech innovation: buying up domains that sound like QAnon Mad Libs in support of Trump’s meme coin. Meanwhile, DOGE decided to hand th…

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11 - Chug It, Brah: Dead Guys, Bad Plays, and Taco Butts 38:47

5M ago38:47

38:47

Welcome back to Schmactors! Season 2 kicks off with James Marsters and Mark Devine diving straight into the fine art of… playing dead. Yep, it’s harder than it looks, and they’ve got the stories (and the scars) to prove it. They’re also spilling the beans on caffeine binges before shows, disastrous productions that still haunt their dreams (Marriag…

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694: Hammers Don’t Hallucinate 1:23:43

5M ago1:23:43

1:23:43

This week on Grumpy Old Geeks, Fyre Festival rises from the ashes yet again—but not as a festival, because even Billy McFarland finally figured out he’s better at selling pipe dreams than tents. Meanwhile, Amazon and Microsoft are tapping the brakes on their AI data center dreams, Google’s AI keeps confidently explaining made-up nonsense like it’s …

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693: Let Them Eat Space 1:23:59

5M ago1:23:59

1:23:59

This week, we blast off with a tale as old as grift: Fyre Fest 2 has been postponed—again—proving that you really can fail upward if you squint hard enough and wear enough white linen. Over at Automattic, employees discovered secret watermarks in their internal comms, because what workplace isn’t better with a sprinkle of corporate surveillance cos…

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692: Confabulation and Frivolity 1:26:41

6M ago1:26:41

1:26:41

This week, the boys kick things off with some serious déjà vu as Fyre Fest’s favorite grifter promises he’s totally throwing another festival — because nothing says “I’ve changed” like doubling down on the same scam. Meanwhile, the IRS decided to become ICE’s BFF by casually sharing migrant tax data, and their commissioner moonwalks out right after…

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691: Cry Me A River (to Cool Off My AI) 1:19:37

6M ago1:19:37

1:19:37

This week, the Geeks wade into a swamp of tech meltdowns, governmental facepalms, and the usual Elon-flavored absurdity. Kicking things off, protesters take their beef with Tesla to the streets while Proud Boys decide this is the hill to vroom and die on. Meanwhile, Elon’s privacy prayers have finally been answered—thanks to new FAA rules, he and T…

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690: An Insult to Life Itself 1:08:00

6M ago1:08:00

1:08:00

The Dunning-Kruger Effect is alive, well, and running the show. Elon’s approval rating is cratering while experts warn he could blow a hole in federal spending; war plans are accidentally texted, and top U.S. officials’ passwords are found online; 23andMe files for bankruptcy; TikTok attempts a patriotic glow-up to stay alive in the U.S.; OpenAI ad…

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689: What Would Dave Do? 1:17:26

6M ago1:17:26

1:17:26

AI influencers with Down syndrome are selling nudes; Tesla’s Autopilot crashes into a cartoon wall while 46,000 Cybertrucks get recalled; ICE ramps up creepy surveillance; OpenAI’s copyright grab faces pushback; California might hand AI to Big Tech on a silver platter; BYD dunks on Tesla with lightning-fast EV charging; White Trash Wins Lotto retur…

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688: Why, Combinator? 1:23:42

6M ago1:23:42

1:23:42

Pi Day gets its due; Y Combinator marks 20 years of “disruption”; Americans lose $12.5B to scams thanks to AI and social media; Deliveroo posts a profit but still tanks on Wall Street; Twitter’s security remains a joke; Pinterest steals user content for AI; and a rogue developer gets busted for a kill switch scheme. Severance Season 2 costs $20M pe…

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687: Uncanny Spaceballs 1:05:12

7M ago1:05:12

1:05:12

Techdirt has finally accepted the inevitable and gone full democracy blog—because let’s face it, politics and tech are now the same dumpster fire. Google rolled out AI Mode for Search, proving once again that the internet is just Clippy with better branding. Meanwhile, Billy McFarland insists Fyre Festival 2 is totally happening, despite Mexican of…

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686: Not All Heroes Vibe Code 1:00:07

7M ago1:00:07

1:00:07

This week, the U.S. government takes another L in court as a judge rules that handing out personal data like free candy to the Department of Government Efficiency (DOGE) is, in fact, a privacy violation. Meanwhile, Elizabeth Holmes and Sunny Balwani’s dreams of walking free are crushed as a judge upholds their fraud convictions and massive fines. S…

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685: Bezos, Jeff Bezos 1:04:53

7M ago1:04:53

1:04:53

Jason and Brian dive into a whirlwind of tech chaos, cultural absurdities, and dystopian developments. They kick things off with a nostalgic nod to the internet's past, highlighting the 88x31 GIF collection and quirky single-use websites like "Trump Golf Track" and "Are We Doomed Yet?" The asteroid 2024 YR4 briefly raises existential dread as NASA’…

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684: Don’t Be a Dick 1:25:47

7M ago1:25:47

1:25:47

In this episode of Grumpy Old Geeks, Jason and Brian dive headfirst into the latest tech absurdities, financial scandals, and Elon Musk's ongoing chaos. We start with the annual frustration of unsubscribing from an email list that just won’t quit before jumping into the latest gem from Musk himself: "Some of the things that I say will be incorrect.…

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683: There IS a Spoon! 1:20:38

8M ago1:20:38

1:20:38

This week, Jason and Brian dive into the chaos surrounding Elon Musk’s growing influence in government tech, with young engineers playing key roles in his takeover. DOGE employees are being ordered off Slack, USAID is crumbling, and Musk’s war with U.S. officials rages on. Meanwhile, AI takes center stage with the EU banning high-risk systems, Deep…

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682: We’re Gonna Need a Bigger Luigi 1:27:25

8M ago1:27:25

1:27:25

Brian and Jason kick things off with a look at why Gen Z grads are getting fired just months after landing jobs and a curiously viral declassified CIA sabotage guide. Speaking of sabotage, U.S. students are struggling with their lowest reading scores in decades, raising questions about the future workforce. Meanwhile, Google Maps’ controversial ren…

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681: Trough of Disillusionment 1:23:28

8M ago1:23:28

1:23:28

In this episode, Brian and Jason kick things off by highlighting the troubling state of the gaming industry, with 11% of developers laid off in 2024, according to a GDC survey. Meanwhile, Elon Musk finds a new way to perplex us all by admitting he pays people to play video games for him. They then unpack a whirlwind of news, including Trump’s contr…

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680: Failed Up 1:03:57

8M ago1:03:57

1:03:57

This week on Grumpy Old Geeks, Jason and Brian dissect the latest tech and cultural news, starting with a TikTok tempest. The Supreme Court’s decision to uphold a law potentially banning the app in the U.S. leaves the ball in Trump’s court, while TikTok’s CEO plans to attend his inauguration. As users flock to alternative Chinese apps and RedNote s…

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679: Set Sanity to Zero 1:23:49

9M ago1:23:49

1:23:49

In Episode 679 of Grumpy Old Geeks, titled "Set Sanity to Zero," Brian and Jason discuss the latest developments in tech, culture, and innovation. The episode opens with a look at Watch Duty, a wildfire-tracking app that has surpassed ChatGPT to take the top spot on the App Store amid California’s wildfire crisis. They also cover local news, includ…