WEBVTT 00:00:00.000 --> 00:00:02.520 Welcome to The Deep Dive, your shortcut to getting 00:00:02.520 --> 00:00:06.679 up to speed. Today, well, we're tackling a career 00:00:06.679 --> 00:00:09.019 that really acts like a mirror, doesn't it? Reflecting 00:00:09.019 --> 00:00:12.300 the last, what, 30 years of American media shifts. 00:00:12.500 --> 00:00:15.820 Exactly. We're digging into the, let's say, unfiltered 00:00:15.820 --> 00:00:19.079 evolution of Nicholas Rocco DiPaolo. Yeah, Nick 00:00:19.079 --> 00:00:24.519 DiPaolo. And when you trace his path, you're 00:00:24.519 --> 00:00:26.820 not just looking at a comedian born in... You 00:00:26.820 --> 00:00:28.780 know, Beverly, Massachusetts, back in 62. Right. 00:00:28.879 --> 00:00:31.859 You're actually tracking this this really controversial, 00:00:32.159 --> 00:00:35.219 often confrontational voices. It moves from like 00:00:35.219 --> 00:00:38.719 the traditional local standup clubs to writing 00:00:38.719 --> 00:00:41.979 for Emmy nominated TV shows, then becoming a 00:00:41.979 --> 00:00:44.340 fixture in that whole shock radio era. Huge part 00:00:44.340 --> 00:00:46.420 of it. Oh, absolutely. And finally landing where 00:00:46.420 --> 00:00:49.140 he is now. Yes. Hosting his own very independent, 00:00:49.259 --> 00:00:52.020 very political digital show. It's quite the journey. 00:00:52.299 --> 00:00:54.320 That's exactly our mission today, then, to trace 00:00:54.320 --> 00:00:56.640 that whole arc, which is, frankly, pretty complex. 00:00:56.659 --> 00:00:59.899 It's a real study in, well, adapting on one hand, 00:00:59.920 --> 00:01:01.960 but also refusing to compromise on the other. 00:01:02.100 --> 00:01:04.040 We're looking at the whole timeline. From those 00:01:04.040 --> 00:01:06.379 first open mics in Boston, what, the late 80s, 00:01:06.379 --> 00:01:09.939 all the way to his current setup. I mean, the 00:01:09.939 --> 00:01:12.879 guy's been everything. Stand -up, writer, actor, 00:01:13.120 --> 00:01:16.780 radio guy, podcast host. A true multi -hyphenate, 00:01:16.840 --> 00:01:20.430 as they say. And his specific style. Which, yeah, 00:01:20.469 --> 00:01:22.730 we'll break down later that mix of observational 00:01:22.730 --> 00:01:25.590 stuff, black comedy, insult humor. It was so 00:01:25.590 --> 00:01:28.590 consistent. Right. And that consistency actually 00:01:28.590 --> 00:01:30.409 let him succeed in all these different, sometimes 00:01:30.409 --> 00:01:34.719 conflicting media worlds. It also set him up 00:01:34.719 --> 00:01:36.959 for some major clashes, you know, with the powers 00:01:36.959 --> 00:01:39.200 that be, the gatekeepers. Yeah, you can see that 00:01:39.200 --> 00:01:41.120 coming. I mean, he was key to tough crowd with 00:01:41.120 --> 00:01:43.060 Colin Quinn, always popping up on the Comedy 00:01:43.060 --> 00:01:45.620 Central roast, a regular voice on massive shows 00:01:45.620 --> 00:01:48.879 like Opie and Anthony, Howard Stern. His career 00:01:48.879 --> 00:01:51.689 pattern seems to be. Get in, do incredibly well, 00:01:51.790 --> 00:01:54.409 push the boundaries and then often get pushed 00:01:54.409 --> 00:01:57.250 out only to like immediately rebuild somewhere 00:01:57.250 --> 00:01:59.390 else. OK, let's unpack all of that. We really 00:01:59.390 --> 00:02:01.349 need to start at the beginning, right? The foundations. 00:02:02.510 --> 00:02:04.670 There's this surprising academic background. 00:02:04.890 --> 00:02:06.549 Yeah, that's interesting. And apparently it was 00:02:06.549 --> 00:02:08.990 sheer desperation, not ambition that got him 00:02:08.990 --> 00:02:10.689 on stage in the first place. Yeah, it's funny. 00:02:10.750 --> 00:02:15.050 His early life. Gives you almost no clue about 00:02:15.050 --> 00:02:17.509 the kind of political and controversial figure 00:02:17.509 --> 00:02:19.150 he'd become. It's pretty standard New England 00:02:19.150 --> 00:02:21.889 stuff. Right. Born in Beverly. Grew up in Danvers, 00:02:21.909 --> 00:02:24.949 Mass. Followed a pretty traditional path, actually. 00:02:25.590 --> 00:02:27.469 Academics, sports. He went to the University 00:02:27.469 --> 00:02:32.060 of Maine. Graduated in 84. Major. Marketing. 00:02:32.379 --> 00:02:35.659 Marketing. That's almost the opposite of his 00:02:35.659 --> 00:02:37.639 later persona, isn't it? Marketing is usually 00:02:37.639 --> 00:02:39.800 about, well, politeness, persuasion. Exactly. 00:02:39.840 --> 00:02:42.180 Not roasting celebrities till they cry. It's 00:02:42.180 --> 00:02:44.360 a fascinating contrast. And yeah, he was apparently 00:02:44.360 --> 00:02:46.400 quite the athlete, too. A running back for the 00:02:46.400 --> 00:02:49.159 university football team. Oh, wow. And he was 00:02:49.159 --> 00:02:52.639 in a fraternity, Sigma Nu. So you see maybe a 00:02:52.639 --> 00:02:55.060 bit of that competitive team player background, 00:02:55.280 --> 00:02:57.379 maybe even, you know, disciplined in a certain 00:02:57.379 --> 00:02:59.360 way. That competitive drive. Yeah, that makes 00:02:59.360 --> 00:03:01.259 sense when you look at the sheer volume of work 00:03:01.259 --> 00:03:04.020 he put in later in comedy. Totally. And competition 00:03:04.020 --> 00:03:06.139 was kind of in the family, it seems. His brother 00:03:06.139 --> 00:03:08.340 was also at Maine doing play by play for the 00:03:08.340 --> 00:03:10.520 Black Bears hockey team, worked alongside Gary 00:03:10.520 --> 00:03:12.740 Thorne, the big time announcer. No kidding. Gary 00:03:12.740 --> 00:03:16.120 Thorne. Yeah. So. You know, the world around 00:03:16.120 --> 00:03:18.879 him valued performance, quick commentary. Yeah. 00:03:18.939 --> 00:03:21.159 Even if it was focused on sports initially. But 00:03:21.159 --> 00:03:23.759 OK, so he graduates with this marketing degree 00:03:23.759 --> 00:03:27.259 that doesn't jump into comedy. No, not right 00:03:27.259 --> 00:03:30.280 away. The sources say he tried the, you know, 00:03:30.280 --> 00:03:33.659 the expected path first office job in marketing. 00:03:33.800 --> 00:03:37.319 OK. But the job that really seems to define that 00:03:37.319 --> 00:03:40.120 period or rather the failure that defined his 00:03:40.120 --> 00:03:43.259 later success was selling meat and seafood. Door 00:03:43.259 --> 00:03:45.620 to door. Door to door meat sales. That sounds 00:03:45.620 --> 00:03:47.900 character building, let's say. Character building 00:03:47.900 --> 00:03:50.580 or soul crushing. Maybe both. But that seems 00:03:50.580 --> 00:03:52.759 to be the key, the motivator. He said he was 00:03:52.759 --> 00:03:55.020 always a fan of comedy, watched Carson, Letterman, 00:03:55.120 --> 00:03:59.379 Leno, Robert Klein, all the greats. But he just 00:03:59.379 --> 00:04:02.020 didn't have, in his own words, the guts to try 00:04:02.020 --> 00:04:04.460 it himself. It took hating that sales job so 00:04:04.460 --> 00:04:06.280 much, that grind that finally pushed him. He 00:04:06.280 --> 00:04:08.439 literally said, desperation led me to the stage, 00:04:08.539 --> 00:04:11.860 not ambition. Wow. I think a lot of people, especially 00:04:11.860 --> 00:04:14.740 creatives, can probably relate to that. You know, 00:04:14.780 --> 00:04:17.079 the pain of the safe job finally getting worse 00:04:17.079 --> 00:04:19.439 than the fear of trying the thing you actually 00:04:19.439 --> 00:04:22.100 love. It's that existential push, right? Makes 00:04:22.100 --> 00:04:24.579 you take the risk. So what was that first actual 00:04:24.579 --> 00:04:27.139 step onto the stage like? Oh, the origin story 00:04:27.139 --> 00:04:30.860 is perfect. Summer of 86, open mic night, Stitches 00:04:30.860 --> 00:04:35.259 Club in Boston. Okay. But he didn't just like... 00:04:35.420 --> 00:04:38.240 calmly prepare he apparently came straight from 00:04:38.240 --> 00:04:42.180 a family barbecue oh having had and i quote about 00:04:42.180 --> 00:04:45.019 22 beers in me 20 okay that's not just loosening 00:04:45.019 --> 00:04:47.220 up that's anesthesia yeah it tells you something 00:04:47.220 --> 00:04:49.920 about the anxiety level maybe but he did his 00:04:49.920 --> 00:04:52.079 five minutes that it went pretty well and crucially 00:04:52.079 --> 00:04:54.980 he knew right then instantly this is what he 00:04:54.980 --> 00:04:57.120 had to do he found the thing he found the thing 00:04:57.120 --> 00:05:00.519 but uh life intervened slightly that sales job 00:05:00.519 --> 00:05:03.019 moved him temporarily to rhode island ah okay 00:05:03.019 --> 00:05:05.810 so a slight detour It's just a brief one. It 00:05:05.810 --> 00:05:09.050 wasn't until spring of 87 that he got back to 00:05:09.050 --> 00:05:11.189 Boston properly and started hitting those open 00:05:11.189 --> 00:05:14.170 mic nights regularly. So 87, that's really the 00:05:14.170 --> 00:05:15.649 starting pistol for the career we're talking 00:05:15.649 --> 00:05:18.209 about today. Trading scallops for hecklers. Pretty 00:05:18.209 --> 00:05:21.009 much. Yeah. A definite upgrade, I imagine. So 00:05:21.009 --> 00:05:24.529 1987, he commits. And from what the sources say, 00:05:24.709 --> 00:05:27.449 he just went all in. Right. Hit the ground running. 00:05:27.610 --> 00:05:29.629 Absolutely relentless. He worked that whole New 00:05:29.629 --> 00:05:32.839 England circuit. The comedy vault, the comedy 00:05:32.839 --> 00:05:34.959 correction places like that, pretty much nonstop 00:05:34.959 --> 00:05:38.500 until about 92. This was his boot camp. Forging 00:05:38.500 --> 00:05:41.439 the act in the fires of Tuesday night crowds 00:05:41.439 --> 00:05:43.819 in Providence. Exactly. Pressure testing the 00:05:43.819 --> 00:05:45.899 material constantly. So what was his style like 00:05:45.899 --> 00:05:47.500 back then? Was he already doing the political 00:05:47.500 --> 00:05:50.720 stuff, the really aggressive bits? Not quite 00:05:50.720 --> 00:05:53.660 yet, it seems. The descriptions from that time 00:05:53.660 --> 00:05:57.040 focus more on the technical side. A rapid -fire 00:05:57.040 --> 00:06:00.819 approach. He aimed for four or five punches attached 00:06:00.819 --> 00:06:03.259 to every joke. Dense. Like a machine gun setup 00:06:03.259 --> 00:06:06.000 punchline delivery. Yeah. Aggressive in pace. 00:06:06.360 --> 00:06:09.420 Trying to just overwhelm you with jokes. It sounds 00:06:09.420 --> 00:06:11.319 like he was really focused on the craft, the 00:06:11.319 --> 00:06:14.240 mechanics of stand -up. His early manager, Barry 00:06:14.240 --> 00:06:17.100 Katz, mentioned he did over 300 nights in his 00:06:17.100 --> 00:06:21.579 first year. 300 nights. That's insane. That kind 00:06:21.579 --> 00:06:23.860 of dedication, you just don't see that as often 00:06:23.860 --> 00:06:26.379 anymore. It's serious work ethic. And that kind 00:06:26.379 --> 00:06:28.399 of grind, well, it naturally leads you to the 00:06:28.399 --> 00:06:30.540 next level, which for comedians then was New 00:06:30.540 --> 00:06:33.120 York City. Right. The big move. And this is where 00:06:33.120 --> 00:06:35.680 a pretty major connection happens, isn't it? 00:06:35.699 --> 00:06:38.279 His roommate in New York. Yeah. None other than 00:06:38.279 --> 00:06:41.019 Louis C .K. Wow. OK. So they were sharing an 00:06:41.019 --> 00:06:43.860 apartment back then. But the move wasn't just 00:06:43.860 --> 00:06:45.959 about networking, right? It actually shifted 00:06:45.959 --> 00:06:49.720 his comedy itself. It seems so. NYC was the catalyst. 00:06:50.490 --> 00:06:52.949 For him getting more political. And how he did 00:06:52.949 --> 00:06:54.709 it is really interesting, especially thinking 00:06:54.709 --> 00:06:57.129 about his later stuff. He said he started reading 00:06:57.129 --> 00:07:00.009 all the local papers, the Post, the Times, Daily 00:07:00.009 --> 00:07:03.050 News. The whole spectrum. Right. The liberal 00:07:03.050 --> 00:07:05.459 ones, the conservative ones. And he'd compare 00:07:05.459 --> 00:07:07.480 how they covered the same story. He was mining 00:07:07.480 --> 00:07:10.319 the differences, the contradictions. Ah, okay. 00:07:10.399 --> 00:07:12.480 So he's actively looking for the tension in how 00:07:12.480 --> 00:07:14.139 things are reported. That makes perfect sense. 00:07:14.379 --> 00:07:16.980 It explains why his later commentary often feels 00:07:16.980 --> 00:07:19.040 like it's hitting from multiple angles. It's 00:07:19.040 --> 00:07:21.680 comedy born from comparing the narratives. Exactly. 00:07:21.680 --> 00:07:24.600 That method, that discipline of looking at conflicting 00:07:24.600 --> 00:07:27.300 media views. You could see the seeds of his news 00:07:27.300 --> 00:07:30.259 satire approach right there. decades before his 00:07:30.259 --> 00:07:33.040 own show. But, you know, comedy dreams often 00:07:33.040 --> 00:07:36.759 lead West to L .A. Yep. In 92, he relocates again. 00:07:37.410 --> 00:07:40.189 Los Angeles this time. Yeah. The goal was TV 00:07:40.189 --> 00:07:42.870 and film roles. And did that L .A. move pay off? 00:07:43.069 --> 00:07:45.470 Pretty quickly, yeah. He got some really crucial 00:07:45.470 --> 00:07:48.350 early national exposure out there. A spot on 00:07:48.350 --> 00:07:50.529 the Arsenio Hall show, which was massive at the 00:07:50.529 --> 00:07:53.310 time. And he did one of ASPO's Young Comedians 00:07:53.310 --> 00:07:55.250 specials. That was a really important launch 00:07:55.250 --> 00:07:57.509 pad for comics back then. Put you on the industry 00:07:57.509 --> 00:08:01.089 radar. So L .A. gives him visibility, but then 00:08:01.089 --> 00:08:03.769 he gets pulled back east. He does. The call came 00:08:03.769 --> 00:08:06.069 from Chris Rock. The Cricks Rock. The Chris Rock, 00:08:06.170 --> 00:08:07.910 offering him a writing job on The Chris Rock 00:08:07.910 --> 00:08:10.490 Show, which filmed in New York. So DiPaolo takes 00:08:10.490 --> 00:08:12.790 it, moves back, settles in Queens around 2001. 00:08:13.209 --> 00:08:16.329 Now, this writing gig, this is important, isn't 00:08:16.329 --> 00:08:18.129 it? Because it kind of pushes back against the 00:08:18.129 --> 00:08:20.329 idea that he was only ever about shock value 00:08:20.329 --> 00:08:23.850 or just insult comedy. Absolutely. Critical context. 00:08:23.910 --> 00:08:26.689 This was high -level, prestigious writing. The 00:08:26.689 --> 00:08:29.050 show was huge, critically acclaimed. He wrote 00:08:29.050 --> 00:08:32.200 for two seasons. And in 2001... He and the whole 00:08:32.200 --> 00:08:35.120 writing team got nominated for an Emmy. Wow. 00:08:35.700 --> 00:08:38.120 Outstanding writing for a variety music or comedy 00:08:38.120 --> 00:08:41.299 program. And get this, it was actually his second 00:08:41.299 --> 00:08:44.200 Emmy nomination overall. Second. Okay, see, that's 00:08:44.200 --> 00:08:46.259 the kind of detail people might miss. He wasn't 00:08:46.259 --> 00:08:48.700 just a club comic who stumbled into radio. He 00:08:48.700 --> 00:08:51.159 had serious writing credentials recognized at 00:08:51.159 --> 00:08:53.580 the highest level. Totally. It proves the skill 00:08:53.580 --> 00:08:56.509 set went way beyond the stage persona. Being 00:08:56.509 --> 00:08:59.230 able to craft sophisticated comedy for TV, getting 00:08:59.230 --> 00:09:01.590 multiple Emmy nods, that underpins everything 00:09:01.590 --> 00:09:03.950 else. It's that combination, the sharp writing 00:09:03.950 --> 00:09:06.649 mind and the increasingly confrontational delivery 00:09:06.649 --> 00:09:09.090 that really fueled the next big phase. Which 00:09:09.090 --> 00:09:12.450 was? Radio on the roasts. This where that unfiltered 00:09:12.450 --> 00:09:15.009 style found its kind of perfect home for a while. 00:09:15.070 --> 00:09:17.289 We're talking major guest spots. Howard Stern, 00:09:17.509 --> 00:09:19.399 Opie and Anthony. Okay, let's talk about shock 00:09:19.399 --> 00:09:21.240 radio for a second, because that term gets thrown 00:09:21.240 --> 00:09:23.259 around. For listeners, you have to understand, 00:09:23.419 --> 00:09:27.919 these shows in the late 90s, early 2000s, they 00:09:27.919 --> 00:09:30.279 were a different beast. Totally different. They 00:09:30.279 --> 00:09:33.419 operated largely outside the FCC rules that governed 00:09:33.419 --> 00:09:36.480 regular radio and TV. They were built on being 00:09:36.480 --> 00:09:39.519 edgy, pushing boundaries, being confrontational. 00:09:39.789 --> 00:09:41.990 So for a comedian like DePaulo, whose whole thing 00:09:41.990 --> 00:09:44.129 was becoming about saying the unsayable insult, 00:09:44.289 --> 00:09:47.690 humor, dark jokes, these shows weren't just tolerating 00:09:47.690 --> 00:09:49.590 him. They were inviting it. Yeah. They needed 00:09:49.590 --> 00:09:52.190 that kind of content. It was the perfect ecosystem 00:09:52.190 --> 00:09:54.789 for his style at that time. And that radio heat, 00:09:54.809 --> 00:09:57.330 it bled back into TV, specifically with Tough 00:09:57.330 --> 00:09:59.980 Crowd. Yeah. Tough crowd with Colin Quinn. Ran 00:09:59.980 --> 00:10:03.340 2002 to 2004 on Comedy Central. Such a foundational 00:10:03.340 --> 00:10:05.740 show for that era. It was basically just comedians 00:10:05.740 --> 00:10:08.039 arguing about the news. Unscripted, political, 00:10:08.320 --> 00:10:10.899 often really heated. The perfect training ground 00:10:10.899 --> 00:10:13.360 for his later podcast, you could argue. That 00:10:13.360 --> 00:10:15.940 rapid fire debate style. Absolutely. And then, 00:10:15.980 --> 00:10:18.139 of course, the ultimate showcase for that aggressive 00:10:18.139 --> 00:10:22.620 style. The Comedy Central roasts. Ah, yes. The 00:10:22.620 --> 00:10:25.340 roasts. He became a staple there. Oh, yeah. Hugh 00:10:25.340 --> 00:10:28.620 Hefner, Pam Anderson, Dennis Leary. Jeff Foxworthy, 00:10:28.740 --> 00:10:31.580 Larry the Cable Guy, he was on a bunch of them. 00:10:31.659 --> 00:10:33.639 And the roast stage is basically a laboratory 00:10:33.639 --> 00:10:36.200 for insult comedy, isn't it? Mixed with maybe 00:10:36.200 --> 00:10:38.539 some of that black comedy stuff. Exactly. You 00:10:38.539 --> 00:10:40.740 could take that aggression, that precise joke 00:10:40.740 --> 00:10:43.620 writing skill he'd honed since Boston, and just 00:10:43.620 --> 00:10:46.360 unleash it in this high profile televised format. 00:10:46.970 --> 00:10:49.389 This period really cemented his public image 00:10:49.389 --> 00:10:51.950 as the guy who'd say anything, the unfiltered 00:10:51.950 --> 00:10:54.669 one. Okay, so before we get into how things started 00:10:54.669 --> 00:10:56.929 to shift with mainstream media, we should probably 00:10:56.929 --> 00:10:59.210 nail down the specific kind of comedy he was 00:10:59.210 --> 00:11:01.049 doing and talk about the key people he worked 00:11:01.049 --> 00:11:03.409 with. Right. The sources list out his genres 00:11:03.409 --> 00:11:06.330 pretty clearly. Observational humor, black comedy, 00:11:06.590 --> 00:11:09.929 insult comedy, news satire, and off -color humor. 00:11:10.330 --> 00:11:12.429 It's quite a mix. Let's unpack maybe two of those. 00:11:12.490 --> 00:11:15.029 Insult comedy is pretty obvious from the roasts, 00:11:15.029 --> 00:11:16.990 right? Yeah, that's straightforward. But black 00:11:16.990 --> 00:11:18.750 comedy is really important for understanding 00:11:18.750 --> 00:11:21.710 him. In his case, it means finding humor in really 00:11:21.710 --> 00:11:25.169 dark, controversial, or taboo subjects. Things 00:11:25.169 --> 00:11:28.330 like race relations, death, social issues people 00:11:28.330 --> 00:11:31.129 usually whisper about. And he uses observational 00:11:31.129 --> 00:11:34.100 humor to pick those apart. Seems like it. pointing 00:11:34.100 --> 00:11:36.399 out hypocrisy or absurdity within those dark 00:11:36.399 --> 00:11:39.019 areas, which is probably why PC culture became 00:11:39.019 --> 00:11:41.500 such a frequent target for him. He's looking 00:11:41.500 --> 00:11:44.059 for the uncomfortable truths, often through a 00:11:44.059 --> 00:11:46.799 deliberately offensive lens. And this style wasn't 00:11:46.799 --> 00:11:49.399 developed in a vacuum. He had some really long 00:11:49.399 --> 00:11:52.220 -standing collaborations. The Lee C .K. one is 00:11:52.220 --> 00:11:54.799 maybe the biggest, started as roommates. It just 00:11:54.799 --> 00:11:56.919 kept going. It wasn't just a brief thing. This 00:11:56.919 --> 00:11:59.159 was a creative partnership that lasted, what, 00:11:59.220 --> 00:12:02.000 two decades? Across different projects. Like 00:12:02.000 --> 00:12:06.500 what? Well, DiPaolo played the super on CK's 00:12:06.500 --> 00:12:09.659 HBO show Lucky Louie. He was in like a dozen 00:12:09.659 --> 00:12:12.440 episodes of Louie on FX, often playing a version 00:12:12.440 --> 00:12:14.460 of himself or characters close to his persona. 00:12:14.519 --> 00:12:17.240 Right, I remember him on Louie. And even as recently 00:12:17.240 --> 00:12:19.879 as 2022, he was in CK's film Fourth of July, 00:12:20.100 --> 00:12:22.360 playing that really obnoxious Uncle Kevin character. 00:12:22.519 --> 00:12:25.360 Stole scenes in that. So that long collaboration, 00:12:25.620 --> 00:12:29.379 it's just a real... Mutual respect or understanding 00:12:29.379 --> 00:12:32.500 of each other's comedic voice. Even if CK's path 00:12:32.500 --> 00:12:34.919 took its own controversial turns later, they 00:12:34.919 --> 00:12:37.940 both seemed drawn to uncomfortable realism. Definitely 00:12:37.940 --> 00:12:40.360 seems that way. Another big partnership, maybe 00:12:40.360 --> 00:12:44.399 a bit more wild, was with Artie Lange. Ah, Artie 00:12:44.399 --> 00:12:46.779 Lange. Met him at a pilot audition, apparently. 00:12:46.980 --> 00:12:48.639 They became good friends and toured together 00:12:48.639 --> 00:12:50.720 a lot. They even went overseas for the troops, 00:12:50.960 --> 00:12:53.539 right? They did. The Operation Mirth USO tour 00:12:53.539 --> 00:12:57.679 in 2008. Went to Afghanistan, Lange headlined, 00:12:57.820 --> 00:13:01.200 DiPaolo was with him. And, you know, performing 00:13:01.200 --> 00:13:04.820 that kind of edgy material in a war zone, it 00:13:04.820 --> 00:13:06.659 said something about their shared no boundaries 00:13:06.659 --> 00:13:08.980 approach. That partnership even became a formal 00:13:08.980 --> 00:13:10.740 show for a while. Yeah, the Nick and Artie show. 00:13:11.399 --> 00:13:14.159 Launched in 2011. It was a syndicated sports 00:13:14.159 --> 00:13:16.539 talk radio show, but with their comedic spin. 00:13:16.860 --> 00:13:19.360 How long did that last with Nick? He left in 00:13:19.360 --> 00:13:22.820 January 2013, so about a year and a half. But 00:13:22.820 --> 00:13:24.639 it was a significant move into being a dedicated 00:13:24.639 --> 00:13:27.259 host, not just a guest. Showed he could carry 00:13:27.259 --> 00:13:30.179 a show, bring that opinionated, funny take to 00:13:30.179 --> 00:13:32.039 sports talk. And we can't really talk about his 00:13:32.039 --> 00:13:34.019 development without mentioning Colin Quinn again. 00:13:34.320 --> 00:13:37.200 Absolutely not. Quinn was huge. Tough Crowd was 00:13:37.200 --> 00:13:39.600 obviously the big platform Quinn gave him, which 00:13:39.600 --> 00:13:42.080 honed that political debate skill. But Quinn 00:13:42.080 --> 00:13:45.299 also apparently titled DePaulo's first two stand 00:13:45.299 --> 00:13:47.460 -up albums. Oh, really? Which ones? Born This 00:13:47.460 --> 00:13:51.639 Way from 99 and Road Rage from 2004. Huh. Interesting. 00:13:51.720 --> 00:13:54.139 So there is this whole interconnected group feeding 00:13:54.139 --> 00:13:56.059 off each other, shaping each other's brands. 00:13:56.200 --> 00:13:57.919 Yeah, it was definitely a scene. They kind of 00:13:57.919 --> 00:14:00.220 created an environment where that aggressive 00:14:00.220 --> 00:14:03.440 truth telling style was the currency. And speaking 00:14:03.440 --> 00:14:07.159 of odd pairings and creative ideas, we have to 00:14:07.159 --> 00:14:09.139 touch on that animated show. Shorties watching 00:14:09.139 --> 00:14:11.600 Shorties. Oh, my God. Shorties. That show was 00:14:11.600 --> 00:14:15.580 peak early 2000s Comedy Central weirdness. Totally. 00:14:15.950 --> 00:14:18.389 It was animated. DiPaolo and Patrice O 'Neill, 00:14:18.490 --> 00:14:20.909 another legend gone too soon, voiced these two 00:14:20.909 --> 00:14:23.110 babies. Yeah, unsupervised babies just sitting 00:14:23.110 --> 00:14:25.309 in diapers, watching clips of other comedians 00:14:25.309 --> 00:14:27.389 and, like, commenting on them in these really 00:14:27.389 --> 00:14:30.210 foul -mouthed, cynical ways. It sounds bizarre, 00:14:30.289 --> 00:14:32.929 but what's fascinating is why they did it. The 00:14:32.929 --> 00:14:34.669 network apparently wanted to capture the chemistry 00:14:34.669 --> 00:14:36.809 between DiPaolo and O 'Neill, which was known 00:14:36.809 --> 00:14:40.480 to be volatile but hilarious from radio. Right. 00:14:40.559 --> 00:14:42.299 They couldn't just put them on another panel 00:14:42.299 --> 00:14:44.559 show, maybe. Maybe not. Tough Crowd was already 00:14:44.559 --> 00:14:46.879 doing that. Yeah. Apparently, DiPaolo himself 00:14:46.879 --> 00:14:49.860 came up with the idea for the babies, which is 00:14:49.860 --> 00:14:51.659 kind of brilliant, right? Using these innocent 00:14:51.659 --> 00:14:53.899 -looking characters to say the absolute most 00:14:53.899 --> 00:14:56.679 offensive, cutting stuff. He made a commentary 00:14:56.679 --> 00:14:59.740 almost. Totally. It really shows his knack for 00:14:59.740 --> 00:15:03.279 blending that intense commentary with these weirdly 00:15:03.279 --> 00:15:05.659 creative formats. Okay, so summing up this phase. 00:15:06.220 --> 00:15:08.740 He is a proven Emmy -nominated writer, a successful 00:15:08.740 --> 00:15:12.240 niche actor, a master of insult and black comedy, 00:15:12.419 --> 00:15:15.019 honed in the wild west of shock radio and shows 00:15:15.019 --> 00:15:17.950 like Tough Crowd. But the media landscape was 00:15:17.950 --> 00:15:19.590 starting to change. Yeah, and that's where the 00:15:19.590 --> 00:15:22.789 friction really starts to build. His style versus 00:15:22.789 --> 00:15:25.870 the changing times. So the early 2000s, he's 00:15:25.870 --> 00:15:27.570 pretty established within the system, right? 00:15:27.629 --> 00:15:29.429 He's got the writing cred, the radio presence. 00:15:29.470 --> 00:15:32.370 He can draw crowds. Definitely an insider. He 00:15:32.370 --> 00:15:34.809 even got his own solo radio hosting gig for a 00:15:34.809 --> 00:15:39.590 bit. Late 2006 on WFNY in New York City. An afternoon 00:15:39.590 --> 00:15:42.029 show. How long did that last? Only till about 00:15:42.029 --> 00:15:46.419 December 2007. The station flipped formats. Which 00:15:46.419 --> 00:15:49.779 happens. After that, though, he became a go -to 00:15:49.779 --> 00:15:53.039 fill -in host for some big names. Jerry Doyle, 00:15:53.080 --> 00:15:55.720 Dennis Miller, Dan Patrick. So he was trusted 00:15:55.720 --> 00:15:58.320 talent, someone the networks could rely on to 00:15:58.320 --> 00:16:01.159 deliver that edgy but still manageable content 00:16:01.159 --> 00:16:02.820 within their framework. Exactly. He was working 00:16:02.820 --> 00:16:05.159 within the system. But you could feel the cultural 00:16:05.159 --> 00:16:07.399 ground shifting underneath, couldn't you? That 00:16:07.399 --> 00:16:09.460 kind of confrontational humor was starting to 00:16:09.460 --> 00:16:12.169 run up against Will. Evolving corporate ideas 00:16:12.169 --> 00:16:14.669 about sensitivity. Yeah. The landscape was changing. 00:16:14.730 --> 00:16:16.690 Yeah. And that tension eventually boiled over 00:16:16.690 --> 00:16:19.429 around 2017, 2018. It did. He got another big 00:16:19.429 --> 00:16:22.970 shot. His own dedicated evening show on Sirius 00:16:22.970 --> 00:16:26.710 XM on the Faction Talk channel. Started May 2017. 00:16:27.129 --> 00:16:29.730 Okay, Sirius XM, satellite radio, that was supposed 00:16:29.730 --> 00:16:31.929 to be the safe zone, right? The place edgy comedy 00:16:31.929 --> 00:16:34.909 could still thrive away from FCC regs? The successor 00:16:34.909 --> 00:16:37.330 to old -school shock radio, in a way? That was 00:16:37.330 --> 00:16:39.549 the perception, yeah. But even satellite radio, 00:16:39.610 --> 00:16:43.210 by the late 2010s, had its limits. Or maybe the 00:16:43.210 --> 00:16:45.230 public nature of social media changed the game 00:16:45.230 --> 00:16:48.629 for everyone, regardless of platform. Ah. So 00:16:48.629 --> 00:16:50.690 what was the specific incident? What finally 00:16:50.690 --> 00:16:52.289 broke the connection with the big institutions? 00:16:52.690 --> 00:16:55.730 It was a tweet. A direct collision between his 00:16:55.730 --> 00:16:58.629 unfiltered style, the immediacy of Twitter, and 00:16:58.629 --> 00:17:01.610 corporate HR policies, basically. What's a tweet 00:17:01.610 --> 00:17:03.690 say? According to the sources, he posted something 00:17:03.690 --> 00:17:05.930 like, school shooters, please confine yourself 00:17:05.930 --> 00:17:09.309 to call campuses, specifically faculty lounges 00:17:09.309 --> 00:17:12.329 at Berkeley, Fresno State, et cetera. Oof. Okay, 00:17:12.390 --> 00:17:15.089 yeah, that's textbook DePaulo black comedy, right? 00:17:15.250 --> 00:17:17.569 Hyper -political, off -collar, hitting a raw 00:17:17.569 --> 00:17:21.049 nerve, extremely dark satire. Exactly. The kind 00:17:21.049 --> 00:17:22.690 of thing he might have said on Opie and Anthony 00:17:22.690 --> 00:17:25.390 10 years earlier, maybe it was some controversy, 00:17:25.569 --> 00:17:28.089 but likely survivable within that bubble. Yeah. 00:17:28.109 --> 00:17:30.410 But posted on his own Twitter account, while 00:17:30.410 --> 00:17:32.549 employed by a major corporation like SiriusXM 00:17:32.549 --> 00:17:35.309 in 2018, the context was entirely different. 00:17:35.410 --> 00:17:38.089 The reaction was swift. Immediate. SiriusXM fired 00:17:38.089 --> 00:17:40.609 him. Termination. And his response, did he apologize? 00:17:40.650 --> 00:17:43.329 Walk it back. Not really apologize for the joke 00:17:43.329 --> 00:17:46.029 itself. His public stance was that SiriusXM completely 00:17:46.029 --> 00:17:48.890 overreacted. He called the tweet poorly worded, 00:17:48.890 --> 00:17:51.710 but argued it was only worth a suspension at 00:17:51.710 --> 00:17:54.269 best. So he wasn't backing down on the intent 00:17:54.269 --> 00:17:57.630 of the humor, the satire. He was arguing about 00:17:57.630 --> 00:18:00.940 the punishment. Precisely. He was basically defending 00:18:00.940 --> 00:18:03.420 his right to make that kind of joke, framing 00:18:03.420 --> 00:18:05.799 the firing as corporate overreach and attack 00:18:05.799 --> 00:18:08.579 on comedic freedom. It perfectly encapsulates 00:18:08.579 --> 00:18:10.619 his whole philosophy about speech and offense. 00:18:10.900 --> 00:18:12.920 It makes you wonder, though, with his track record, 00:18:13.059 --> 00:18:15.680 the Emmy nods, the connections, why not just 00:18:15.680 --> 00:18:18.759 soften the edges a bit? Play the game to stay 00:18:18.759 --> 00:18:21.180 within those big platforms instead of essentially 00:18:21.180 --> 00:18:23.940 burning that bridge with Sirius XM. I think for 00:18:23.940 --> 00:18:26.220 him, compromising the material, softening the 00:18:26.220 --> 00:18:28.700 edges would have been like abandoning the entire 00:18:28.700 --> 00:18:30.730 point. His whole brand, his whole philosophy 00:18:30.730 --> 00:18:34.130 was built on not doing that, on pushing back 00:18:34.130 --> 00:18:36.970 against exactly those kinds of pressures. So 00:18:36.970 --> 00:18:39.569 the firing, in a weird way, might have been inevitable. 00:18:39.750 --> 00:18:42.410 It forced the next step. Which was? The independent 00:18:42.410 --> 00:18:44.990 leap. He had to build his own platform where 00:18:44.990 --> 00:18:46.609 he couldn't be fired for being himself. Then 00:18:46.609 --> 00:18:48.829 he moved fast on that, didn't he? Incredibly 00:18:48.829 --> 00:18:51.670 fast. Yeah. The SiriusXM firing was April 2018. 00:18:51.890 --> 00:18:54.910 By July 9th, 2018, just a few months later, the 00:18:54.910 --> 00:18:57.460 Nick DiPaolo show launched. audio and video podcast 00:18:57.460 --> 00:19:01.319 wow that's the modern playbook isn't it get deplatformed 00:19:01.319 --> 00:19:03.660 by the old guard immediately pivot to your own 00:19:03.660 --> 00:19:06.220 audience directly online textbook example don't 00:19:06.220 --> 00:19:08.200 wait don't complain too long just build your 00:19:08.200 --> 00:19:10.039 own thing let's look at how he built it because 00:19:10.039 --> 00:19:12.160 the structure seems pretty smart for this kind 00:19:12.160 --> 00:19:14.319 of unfiltered content it's basically talk radio 00:19:14.319 --> 00:19:17.140 but redesigned for the internet age an hour long 00:19:17.140 --> 00:19:19.920 four days a week he broadcasts live from his 00:19:19.920 --> 00:19:22.220 own studio setup and how does he manage reach 00:19:22.220 --> 00:19:25.559 versus revenue smartly The live show streams 00:19:25.559 --> 00:19:28.420 free on YouTube. They get some maximum eyeballs, 00:19:28.660 --> 00:19:32.160 keep some visible. But the real money, the dedicated 00:19:32.160 --> 00:19:34.960 fan base, that comes through Patreon. Premium 00:19:34.960 --> 00:19:37.759 content, archives, extras. And the Patreon name 00:19:37.759 --> 00:19:41.220 itself is a statement. Oh, yeah. Creating an 00:19:41.220 --> 00:19:44.880 unsafe space for all. Chuckles. Okay. That's 00:19:44.880 --> 00:19:46.960 pretty direct. It's defiant branding, isn't it? 00:19:46.980 --> 00:19:49.940 A direct flip of the safe space idea. It clearly 00:19:49.940 --> 00:19:52.000 signals exactly what you're getting. The opposite 00:19:52.000 --> 00:19:54.359 of PC culture. That's his core audience. And 00:19:54.359 --> 00:19:57.160 his topics reflect that. News, politics, modern 00:19:57.160 --> 00:20:00.920 society, race, social justice, all through his 00:20:00.920 --> 00:20:03.839 specific lens. And this setup allows him to talk 00:20:03.839 --> 00:20:06.619 to whoever he wants, right? A guest who might 00:20:06.619 --> 00:20:08.740 also be a bit too controversial for mainstream 00:20:08.740 --> 00:20:11.559 platforms. Exactly. He's had people like Kurt 00:20:11.559 --> 00:20:13.940 Metzger, A .J. Rice, Colin Quinn comes back, 00:20:14.039 --> 00:20:16.559 Anthony Cumia. He's created his own ecosystem. 00:20:16.839 --> 00:20:18.359 But here's where it gets interesting, right? 00:20:18.539 --> 00:20:22.440 He achieves this total independence. But he doesn't 00:20:22.440 --> 00:20:26.079 stay completely isolated in his own digital world. 00:20:26.240 --> 00:20:28.380 No, he doesn't. And this is a really key development. 00:20:28.579 --> 00:20:31.480 Since 2021, our sources say he's been a contributing 00:20:31.480 --> 00:20:34.299 writer for Greg Gutfeld's show on Fox News Channel. 00:20:34.440 --> 00:20:37.460 Gutfeld, the late night show, writing for them. 00:20:37.599 --> 00:20:40.000 Yeah, providing material, helping write, opening 00:20:40.000 --> 00:20:42.519 monologues sometimes. It's a subtle but significant 00:20:42.519 --> 00:20:45.460 shift. He went from being fired by a generally 00:20:45.460 --> 00:20:48.599 neutral corporation like Sirius XM to contributing 00:20:48.599 --> 00:20:51.440 content within a specifically political conservative 00:20:51.440 --> 00:20:55.039 media structure like Fox News. It's just that 00:20:55.039 --> 00:20:57.740 even for an independent, some kind of alignment 00:20:57.740 --> 00:21:00.640 might be necessary or desirable for visibility 00:21:00.640 --> 00:21:02.920 or stability. He's aligning his writing talent, 00:21:03.039 --> 00:21:04.900 which we know is top notch, with a very specific 00:21:04.900 --> 00:21:07.420 political brand. And that alignment trend continued. 00:21:08.119 --> 00:21:11.680 In March 2023, he officially joined Mug Club. 00:21:11.859 --> 00:21:14.000 Stephen Crowder's network. Right. Which puts 00:21:14.000 --> 00:21:17.180 him alongside other very polarizing, mostly conservative 00:21:17.180 --> 00:21:20.660 figures like Alex Jones, Brian Callen. It's another 00:21:20.660 --> 00:21:23.599 move away from pure independence towards joining 00:21:23.599 --> 00:21:26.319 a larger politically defined digital platform. 00:21:26.519 --> 00:21:29.799 So the journey seems to be. Traditional media 00:21:29.799 --> 00:21:32.440 code, it gets pushed out, it creates independent 00:21:32.440 --> 00:21:35.539 platform, aligns independent platform with larger 00:21:35.539 --> 00:21:38.700 politically specific networks. That seems to 00:21:38.700 --> 00:21:41.180 be the trajectory. The traditional gatekeepers 00:21:41.180 --> 00:21:44.220 are gone, but maybe new politically aligned gatekeepers 00:21:44.220 --> 00:21:45.980 offer a different kind of structure and reach. 00:21:46.180 --> 00:21:48.660 It's less about content neutrality and more about 00:21:48.660 --> 00:21:51.029 finding your specific audience block. Throughout 00:21:51.029 --> 00:21:53.529 all these shifts, radio, firing, independence, 00:21:53.930 --> 00:21:55.890 alignment, he kept putting out stand -up specials, 00:21:55.890 --> 00:21:58.049 right? Those seem like key markers of his evolution. 00:21:58.349 --> 00:22:00.509 Absolutely. They're like snapshots of his material 00:22:00.509 --> 00:22:02.190 and worldview at different points. We mentioned 00:22:02.190 --> 00:22:05.369 the early ones, Born This Way, 99, Road Rage, 00:22:05.369 --> 00:22:09.210 04, What Came After. Funny How, in 2008. Then 00:22:09.210 --> 00:22:12.470 Raw Nerve in 2011. That one was interesting because 00:22:12.470 --> 00:22:14.769 it was released both as a Comedy Central Presents 00:22:14.769 --> 00:22:17.690 half hour and as a full special on Showtime. 00:22:17.970 --> 00:22:20.130 Still working within the traditional system then. 00:22:20.430 --> 00:22:22.650 But then things started to change, even in how 00:22:22.650 --> 00:22:24.970 he released them. Yeah, by 2014, with another 00:22:24.970 --> 00:22:27.009 senseless killing, you see him choosing a very 00:22:27.009 --> 00:22:30.170 specific vibe. He filmed it at Acme, a small 00:22:30.170 --> 00:22:32.430 club in Minneapolis. Really intimate setting. 00:22:32.549 --> 00:22:34.970 Going for that raw, immediate feel, like being 00:22:34.970 --> 00:22:37.650 back on the circuit. Seems like it. Less polish, 00:22:37.730 --> 00:22:40.509 more intensity. Then came Inflammatory in 2017, 00:22:40.809 --> 00:22:43.690 just before the SiriusXM stuff hit the fan. But 00:22:43.690 --> 00:22:45.769 the really strategic one, the one that reflects 00:22:45.769 --> 00:22:48.390 the big pivot, seems to be a breath of fresh 00:22:48.390 --> 00:22:51.410 air in 2019, released right after the firing. 00:22:51.650 --> 00:22:55.210 And he put it out. How? For free. Directly onto 00:22:55.210 --> 00:22:56.690 YouTube. Okay, that's a major statement. Why 00:22:56.690 --> 00:22:59.589 free? His stated reason was explicit. He wanted 00:22:59.589 --> 00:23:01.930 to release it without any media industry filter. 00:23:02.170 --> 00:23:04.569 No network notes from Netflix or Comedy Central. 00:23:04.730 --> 00:23:07.509 No executive demanding cuts to avoid controversy. 00:23:07.890 --> 00:23:10.289 So it was partly artistic control, but also a 00:23:10.289 --> 00:23:12.410 business move, bypassing the gatekeepers entirely. 00:23:13.099 --> 00:23:15.960 Exactly. Get it directly to the audience. Maximize 00:23:15.960 --> 00:23:18.380 reach. Find everyone who might be looking for 00:23:18.380 --> 00:23:21.420 exactly that kind of unsiltered comedy, but maybe 00:23:21.420 --> 00:23:23.640 wouldn't pay for a subscription or buy a special 00:23:23.640 --> 00:23:27.019 site unseen. It was a direct pipeline using YouTube 00:23:27.019 --> 00:23:30.140 as the distribution network. Very smart. Very 00:23:30.140 --> 00:23:32.000 much of the moment. And his personal life also 00:23:32.000 --> 00:23:35.440 kind of mirrors this political trajectory, doesn't 00:23:35.440 --> 00:23:37.539 it? His physical location. Yeah, that's another 00:23:37.539 --> 00:23:40.640 layer. He married his wife, Andrea. Back in March 00:23:40.640 --> 00:23:43.220 2003, they'd been together since 94, so a long 00:23:43.220 --> 00:23:45.160 -term relationship. Right. And they lived around 00:23:45.160 --> 00:23:48.259 the New York area for years. Queens, then Tarrytown, 00:23:48.440 --> 00:23:51.980 then Newcastle by 2004. Standard suburban New 00:23:51.980 --> 00:23:54.299 York life for a successful comic. But then came 00:23:54.299 --> 00:23:58.349 the big move. The big move. April 2019. Right 00:23:58.349 --> 00:24:00.109 after he'd launched his independent show and 00:24:00.109 --> 00:24:02.549 really leaned into the anti -establishment vibe, 00:24:02.789 --> 00:24:05.210 he and Andreu moved to Georgia. And he didn't 00:24:05.210 --> 00:24:07.789 just move quietly. He made a point of why he 00:24:07.789 --> 00:24:10.410 was moving. Oh, yeah. He made a very public, 00:24:10.509 --> 00:24:13.509 very provocative statement calling New York a 00:24:13.509 --> 00:24:16.289 liberal shirt hole. Wow. OK, so he's literally 00:24:16.289 --> 00:24:19.309 using his geographic move as content, as part 00:24:19.309 --> 00:24:22.150 of his brand narrative. Totally. It fused everything 00:24:22.150 --> 00:24:24.869 together. His personal life choice, his political 00:24:24.869 --> 00:24:27.690 stance, his comedy content. It became the symbol 00:24:27.690 --> 00:24:30.730 of him escaping the perceived liberal oppression 00:24:30.730 --> 00:24:34.170 of New York for the freedom of the South. Powerful 00:24:34.170 --> 00:24:36.839 storytelling for his base. And all of this, this 00:24:36.839 --> 00:24:39.720 whole journey, it really comes back to a core 00:24:39.720 --> 00:24:42.039 belief he seems to have held for a long, long 00:24:42.039 --> 00:24:45.240 time about offense, about words. Absolutely. 00:24:45.259 --> 00:24:47.279 It's remarkably consistent. There was a New York 00:24:47.279 --> 00:24:50.700 Times article way back in 2007. This is pre Twitter 00:24:50.700 --> 00:24:53.119 firing, pre Trump even, that talked about him 00:24:53.119 --> 00:24:56.059 and the. Shock Radio Brethren after the Don Imus 00:24:56.059 --> 00:24:58.400 controversy. And what did it say about DiPaolo 00:24:58.400 --> 00:25:01.079 specifically? It highlighted his stance against 00:25:01.079 --> 00:25:03.660 PC culture even back then. It quoted a bit he 00:25:03.660 --> 00:25:05.460 did mocking some kind of employee sensitivity 00:25:05.460 --> 00:25:08.460 training manual. The manual was apparently titled 00:25:08.460 --> 00:25:12.380 Words Hurt and Harm. OK. And DiPaolo's punchline, 00:25:12.400 --> 00:25:14.900 his core argument was right away we're starting 00:25:14.900 --> 00:25:17.099 with a false premise because words don't hurt. 00:25:17.500 --> 00:25:20.140 Words don't hurt. That's basically the key to 00:25:20.140 --> 00:25:22.059 understanding his entire approach, isn't it? 00:25:22.140 --> 00:25:24.559 It really is. It's the engine behind the insult 00:25:24.559 --> 00:25:26.819 comedy, the black comedy, the political jabs. 00:25:26.859 --> 00:25:29.720 It's his justification for saying anything, for 00:25:29.720 --> 00:25:32.119 pushing boundaries in every single environment 00:25:32.119 --> 00:25:34.960 he's been in, regardless of the fallout. His 00:25:34.960 --> 00:25:36.920 whole move towards independence, you could argue, 00:25:37.099 --> 00:25:40.480 was about finding or creating a space where that 00:25:40.480 --> 00:25:43.660 single premise, words don't hurt, could exist 00:25:43.660 --> 00:25:46.759 without institutional punishment. Okay, so looking 00:25:46.759 --> 00:25:48.619 back at this whole trajectory, Nick DiPaolo's 00:25:48.619 --> 00:25:51.380 career, it really is like a microcosm, isn't 00:25:51.380 --> 00:25:53.920 it? A case study of a performer whose style, 00:25:54.039 --> 00:25:57.140 that consistent confrontational style, it brought 00:25:57.140 --> 00:26:00.299 him success, but eventually just became incompatible 00:26:00.299 --> 00:26:02.700 with where mainstream media was heading on sensitivity. 00:26:03.390 --> 00:26:05.349 Yeah, he didn't really change his core product. 00:26:05.430 --> 00:26:07.670 The market around him changed. So he didn't bend 00:26:07.670 --> 00:26:10.609 his brand to fit the market. He found a new market 00:26:10.609 --> 00:26:13.349 or rather built his own venue for it. And he 00:26:13.349 --> 00:26:15.529 showed it's possible, right, to go from the traditional 00:26:15.529 --> 00:26:18.430 Heights Emmy nominations, big radio shows to 00:26:18.430 --> 00:26:20.950 being essentially kicked out and then successfully 00:26:20.950 --> 00:26:23.130 launching your own independent thing, your own 00:26:23.130 --> 00:26:25.470 profitable media company, basically on YouTube 00:26:25.470 --> 00:26:28.609 and Patreon. Definitely. And for you, the listener, 00:26:28.730 --> 00:26:30.650 that's maybe the big practical takeaway here. 00:26:30.920 --> 00:26:35.880 His path shows that modern reality for creators, 00:26:36.160 --> 00:26:38.819 especially those with strong, maybe controversial 00:26:38.819 --> 00:26:42.559 viewpoints, if you prioritize unfiltered content 00:26:42.559 --> 00:26:45.259 over playing it safe within the old institutions. 00:26:45.720 --> 00:26:47.519 The tools are there now. The tools are there. 00:26:47.619 --> 00:26:50.079 The tech allows the audience to find you, to 00:26:50.079 --> 00:26:52.460 follow the content directly, even if the big 00:26:52.460 --> 00:26:54.779 networks or platforms try to sideline you. That's 00:26:54.779 --> 00:26:56.880 the optimistic view, the independent success 00:26:56.880 --> 00:26:59.849 story. It is, but... And here's where it gets 00:26:59.849 --> 00:27:01.769 really, really interesting. And this is the final 00:27:01.769 --> 00:27:03.410 thought we want to leave you with today. Okay. 00:27:03.529 --> 00:27:05.470 We saw him make that move. Break free from the 00:27:05.470 --> 00:27:07.549 networks. Build a successful independent show. 00:27:07.910 --> 00:27:10.690 Run it for, what, five plus years now? Total 00:27:10.690 --> 00:27:13.569 control? Right. The unsafe space for all. Exactly. 00:27:13.750 --> 00:27:17.609 But then, recently, he takes these steps back 00:27:17.609 --> 00:27:20.470 towards larger structures. He joins Steven Crowder's 00:27:20.470 --> 00:27:22.769 Mug Love Network. He starts writing for Gutfeld. 00:27:23.259 --> 00:27:26.400 on Fox News aligning himself with big established 00:27:26.400 --> 00:27:29.240 politically specific brands not neutral platforms 00:27:29.240 --> 00:27:32.720 but ideologically aligned ones precisely so what 00:27:32.720 --> 00:27:36.000 does that tell us ultimately about how viable 00:27:36.000 --> 00:27:38.900 truly independent media or comedy is in the long 00:27:38.900 --> 00:27:42.480 run is that Total autonomy, that lone wolf status, 00:27:42.660 --> 00:27:44.880 actually sustainable for years and years. Or 00:27:44.880 --> 00:27:47.319 do you eventually need to hook your wagon to 00:27:47.319 --> 00:27:49.700 some kind of larger structure, even if it's a 00:27:49.700 --> 00:27:52.200 politically specific one, to maintain reach, 00:27:52.480 --> 00:27:55.519 stability, maybe relevance? Does that political 00:27:55.519 --> 00:27:57.680 alignment eventually have to replace the old 00:27:57.680 --> 00:27:59.799 institutional support in today's media world? 00:28:00.559 --> 00:28:02.799 Can you be truly independent and still thrive 00:28:02.799 --> 00:28:05.460 long term? Or does the need for audience and 00:28:05.460 --> 00:28:07.880 structure inevitably pull you into one camp or 00:28:07.880 --> 00:28:10.059 another? Does the desire for reach eventually 00:28:10.059 --> 00:28:12.680 compromise the purity of that independence? Hmm. 00:28:13.519 --> 00:28:15.359 That is definitely something to chew on. Yeah. 00:28:15.420 --> 00:28:16.980 A question about the future of media, really. 00:28:17.400 --> 00:28:19.940 Fascinating stuff. OK, that wraps up our deep 00:28:19.940 --> 00:28:22.099 dive into the unfiltered evolution of Ingrid 00:28:22.099 --> 00:28:23.839 Paolo. Thanks for joining us. See you next time.