WEBVTT 00:00:00.000 --> 00:00:02.779 Welcome back to The Deep Dive. Today we're looking 00:00:02.779 --> 00:00:05.900 at what you might call a career blueprint for 00:00:05.900 --> 00:00:09.240 a working comedian. And we're using John Caparulo's 00:00:09.240 --> 00:00:12.980 path as our sort of case study. Yeah, it's a 00:00:12.980 --> 00:00:14.679 great example. We've got this really detailed 00:00:14.679 --> 00:00:17.379 biography, almost like a strategic timeline. 00:00:17.699 --> 00:00:20.359 And when you lay it all out, Caparulo's career 00:00:20.359 --> 00:00:25.179 is not just a series of gigs. It feels planned. 00:00:26.179 --> 00:00:28.460 Calculated almost. Right. It's a master class, 00:00:28.600 --> 00:00:31.000 really, in how you take that temporary buzz, 00:00:31.239 --> 00:00:33.700 a late night set, being a panelist, and you turn 00:00:33.700 --> 00:00:35.840 it into something solid, something you own, like 00:00:35.840 --> 00:00:38.219 that Vegas residency he has now. Exactly. And 00:00:38.219 --> 00:00:39.820 that's the core question we want to unpack today 00:00:39.820 --> 00:00:42.429 for you listening. How does someone like Caparulo 00:00:42.429 --> 00:00:45.509 strategically navigate that balancing needing 00:00:45.509 --> 00:00:47.630 that mainstream TV exposure, which is crucial 00:00:47.630 --> 00:00:49.969 early on, but then pivoting towards creating 00:00:49.969 --> 00:00:52.130 your own stuff, independent content and finally 00:00:52.130 --> 00:00:53.969 landing something sustainable like a residency? 00:00:54.210 --> 00:00:56.149 It's not just about the jokes, is it? It's about 00:00:56.149 --> 00:00:57.929 building a business, controlling your creative 00:00:57.929 --> 00:01:00.229 output. Precisely. And looking at the source 00:01:00.229 --> 00:01:02.329 material, you can kind of break his journey down 00:01:02.329 --> 00:01:05.329 to three key phases, strategically speaking. 00:01:05.730 --> 00:01:08.109 First, you've got what I call the grind in proximity. 00:01:08.409 --> 00:01:10.969 Those early years, pure hustle, just trying to 00:01:10.969 --> 00:01:13.590 be physically near where things happen. Then 00:01:13.590 --> 00:01:16.930 comes phase two, the visibility engine. This 00:01:16.930 --> 00:01:19.950 is where TV, especially consistent TV, turns 00:01:19.950 --> 00:01:22.090 him from just another comic into someone people 00:01:22.090 --> 00:01:24.790 recognize, a brand. Makes sense. And finally, 00:01:24.790 --> 00:01:28.260 phase three. IP control and residency. Taking 00:01:28.260 --> 00:01:30.480 that brand recognition and locking down ownership 00:01:30.480 --> 00:01:33.299 of his material, his schedule, his income. All 00:01:33.299 --> 00:01:35.439 right, let's dive into phase one then. The beginning. 00:01:35.620 --> 00:01:37.200 Okay, so starting right at the beginning, let's 00:01:37.200 --> 00:01:39.680 ground this. John Caparulo, born East Liverpool, 00:01:39.920 --> 00:01:44.140 Ohio, September 22, 1975. Solid Midwestern roots. 00:01:44.340 --> 00:01:46.459 Yeah, and he stayed there through college, Kent 00:01:46.459 --> 00:01:49.420 State University, graduated in 98. And it's interesting, 00:01:49.519 --> 00:01:51.200 these roots aren't just trivia points, are they? 00:01:51.260 --> 00:01:53.079 They seem kind of central to his whole comedy 00:01:53.079 --> 00:01:56.459 persona later on. Absolutely. That everyman thing, 00:01:56.599 --> 00:02:00.780 it feels authentic because it is authentic. For 00:02:00.780 --> 00:02:03.459 observational comedy, having that specific grounding, 00:02:03.640 --> 00:02:06.359 that viewpoint, it's gold. He wasn't trying to 00:02:06.359 --> 00:02:08.879 be some edgy coastal type. Right. And he didn't 00:02:08.879 --> 00:02:11.439 waste time. The source says he started stand 00:02:11.439 --> 00:02:14.500 -up in 1997. So while still in college or just 00:02:14.500 --> 00:02:17.120 after? Yeah, which shows an immediate commitment. 00:02:17.180 --> 00:02:19.219 He wasn't waiting around to feel ready or whatever. 00:02:19.360 --> 00:02:21.199 He just jumped in. Where did he start performing 00:02:21.199 --> 00:02:23.680 then? Back in Ohio? Uh -huh. Initially, yeah. 00:02:24.460 --> 00:02:26.879 nightclubs in Cleveland and Pittsburgh, too, 00:02:27.039 --> 00:02:29.259 those regional scenes. That's often overlooked, 00:02:29.360 --> 00:02:32.400 that early grind outside the big centers, learning 00:02:32.400 --> 00:02:34.800 to handle crowds that aren't, you know, industry 00:02:34.800 --> 00:02:37.000 people. Oh, it's crucial. It toughens you up, 00:02:37.060 --> 00:02:39.360 makes you learn what actually works with real 00:02:39.360 --> 00:02:41.939 people, not just other comics. It's like a crucible 00:02:41.939 --> 00:02:44.300 for your material. Builds the stamina, I guess. 00:02:44.500 --> 00:02:48.620 Totally. But the real commitment, the L .A. grind, 00:02:48.840 --> 00:02:51.039 as we called it, starts when he makes that move, 00:02:51.159 --> 00:02:54.050 West Coast. Los Angeles. Right. The classic move. 00:02:54.310 --> 00:02:56.770 And this is where you see the sacrifice involved. 00:02:57.150 --> 00:03:00.449 The source details his jobs at the time, and 00:03:00.449 --> 00:03:02.449 it's pretty revealing. This is the part that 00:03:02.449 --> 00:03:05.090 always stands out to me. He had two jobs for 00:03:05.090 --> 00:03:08.349 several years, right? Yep. Wildly different jobs, 00:03:08.389 --> 00:03:11.469 too. He was a doorman at the Comedy Store in 00:03:11.469 --> 00:03:14.969 Hollywood. Iconic place. Wow. And at the same 00:03:14.969 --> 00:03:18.189 time, he was working as a groundskeeper at Golf 00:03:18.189 --> 00:03:20.990 Course. A doorman and a groundskeeper. That's... 00:03:21.360 --> 00:03:23.919 that's a serious hustle like physically demanding 00:03:23.919 --> 00:03:27.500 long hours probably absolutely think about it 00:03:27.500 --> 00:03:29.639 the groundskeeper job that's the practical one 00:03:29.639 --> 00:03:32.400 pays the rent probably decent reliable hours 00:03:32.400 --> 00:03:35.360 outdoors yeah keeps you solvent okay makes sense 00:03:35.360 --> 00:03:37.379 keeps the lights on but the doorman job at the 00:03:37.379 --> 00:03:40.219 comedy store that's the strategic move that's 00:03:40.219 --> 00:03:42.180 not just about the paycheck which was probably 00:03:42.180 --> 00:03:44.419 minimal right what's the strategy there just 00:03:44.419 --> 00:03:46.840 being your comedy exactly it's proximity you 00:03:46.840 --> 00:03:48.719 are literally standing at the doorway through 00:03:48.719 --> 00:03:52.020 which every important comedian booker agent manager 00:03:52.020 --> 00:03:55.780 network exec in town has to walk you're seeing 00:03:55.780 --> 00:03:58.000 everyone you're seeing everyone you're hearing 00:03:58.000 --> 00:04:00.520 everything you become a familiar face it's like 00:04:00.520 --> 00:04:03.139 an apprenticeship through sheer presence but 00:04:03.139 --> 00:04:05.680 couldn't that be like psychologically brutal 00:04:05.680 --> 00:04:08.099 you're exhausted from your day job maybe and 00:04:08.099 --> 00:04:10.560 then you spend your night watching comics kill 00:04:10.560 --> 00:04:13.159 on stage people living the dream you want while 00:04:13.159 --> 00:04:15.479 you're checking IDs or whatever oh it's definitely 00:04:15.479 --> 00:04:17.920 a massive mental test yeah no doubt and that's 00:04:17.920 --> 00:04:20.279 probably why not everyone who tries that path 00:04:20.279 --> 00:04:23.600 makes it you need resilience yeah but if you 00:04:23.600 --> 00:04:26.939 can handle it the payoff is potentially huge 00:04:27.670 --> 00:04:30.230 You're soaking up comedy just by being there. 00:04:30.610 --> 00:04:34.209 Timing, stage presence, joke structure, osmosis. 00:04:34.209 --> 00:04:36.709 You're learning passively. And crucially, you 00:04:36.709 --> 00:04:38.689 become known to the people who matter, not as 00:04:38.689 --> 00:04:41.170 a threat, just as that guy who works the door. 00:04:41.350 --> 00:04:43.230 Yeah. So you finally do get a shot on stage, 00:04:43.290 --> 00:04:45.490 maybe an audition spot. People recognize you. 00:04:45.529 --> 00:04:47.699 They know you've put in the time. paid your dues. 00:04:47.819 --> 00:04:50.120 Okay, I see that. It's about demonstrating commitment, 00:04:50.319 --> 00:04:52.699 being visible within the scene itself. He was 00:04:52.699 --> 00:04:55.639 prioritizing that strategic position, that network 00:04:55.639 --> 00:04:58.740 access, even if it meant hardship over maybe 00:04:58.740 --> 00:05:01.319 a slightly better paying job somewhere else that 00:05:01.319 --> 00:05:05.579 kept him isolated. So phase one summed up. Maintain 00:05:05.579 --> 00:05:09.079 your authentic voice. The Ohio roots. But physically 00:05:09.079 --> 00:05:11.800 plant yourself where the industry action is, 00:05:11.860 --> 00:05:14.920 L .A., and find a way to be in the key locations, 00:05:15.019 --> 00:05:18.240 even if it's sweeping the floor. Proximity over 00:05:18.240 --> 00:05:21.279 pay, basically. Perfectly put. And all that groundwork, 00:05:21.300 --> 00:05:23.740 all that grinding, it set the stage for what 00:05:23.740 --> 00:05:25.720 happened next, which wasn't slow and steady. 00:05:25.819 --> 00:05:27.720 It was pretty explosive. Right. The breakthrough. 00:05:27.839 --> 00:05:31.579 OK, so 2003 seems to be the watershed year. Everything 00:05:31.579 --> 00:05:34.079 changes. Dramatically. All that time, work in 00:05:34.079 --> 00:05:36.379 the door, work in the clubs. It paid off. Yeah. 00:05:36.439 --> 00:05:39.399 Big time. The catalyst was his appearance at 00:05:39.399 --> 00:05:41.759 the Just for Laughs festival in Montreal. The 00:05:41.759 --> 00:05:43.860 big one. Yeah. For comics, that's like the Olympics 00:05:43.860 --> 00:05:45.819 or something. If you do well there, everyone 00:05:45.819 --> 00:05:47.920 notices. And apparently he crushed it. And the 00:05:47.920 --> 00:05:51.019 source says the impact was immediate. Immediate 00:05:51.019 --> 00:05:53.259 is the word used. Yeah. It's kind of rare. It 00:05:53.259 --> 00:05:55.120 says he was immediately offered a sitcom. Wow. 00:05:55.240 --> 00:05:57.860 Straight off the bat. They saw him as having 00:05:57.860 --> 00:06:00.279 that commercial appeal, right? And maybe even 00:06:00.279 --> 00:06:02.699 more importantly, strategically, he got offered 00:06:02.699 --> 00:06:04.920 a spot on the Late Late Show with Craig Kilbourne. 00:06:05.279 --> 00:06:07.540 Okay, that's huge. That first late night spot, 00:06:07.699 --> 00:06:09.639 that's the traditional marker, isn't it? Moves 00:06:09.639 --> 00:06:12.459 you up a level. It's the currency. It turns you 00:06:12.459 --> 00:06:15.959 from a club headliner, maybe, into someone bookable 00:06:15.959 --> 00:06:18.660 nationwide, someone agents take more seriously. 00:06:18.819 --> 00:06:20.339 And you can see in the dates, right, he gets 00:06:20.339 --> 00:06:22.459 on Kilbourne quickly. Yep. First appearance, 00:06:22.720 --> 00:06:27.639 May 7, 2003. Then, crucially, he's back less 00:06:27.639 --> 00:06:31.240 than a year later, May 5, 2004. Getting rebooked 00:06:31.240 --> 00:06:34.029 quickly like that? That's a good sign. It's the 00:06:34.029 --> 00:06:36.250 industry saying, OK, he worked. The audience 00:06:36.250 --> 00:06:38.589 liked him. I'm back. That builds momentum fast. 00:06:38.769 --> 00:06:40.810 And that momentum opened other doors, right? 00:06:40.870 --> 00:06:43.529 More TV spots. Definitely. He landed on Comedy 00:06:43.529 --> 00:06:47.310 Central's Premium Blend in February 2005. That's 00:06:47.310 --> 00:06:49.389 important for reaching the core younger comedy 00:06:49.389 --> 00:06:52.029 audience on cable. OK. But the real mainstream 00:06:52.029 --> 00:06:55.009 validation back then, the big prize, was The 00:06:55.009 --> 00:06:58.399 Tonight Show. With Jay Leno. Ah, yes. The ultimate 00:06:58.399 --> 00:07:00.819 seal of approval for broad appeal. Did he get 00:07:00.819 --> 00:07:03.240 on Leno? He did. And not just once. He became 00:07:03.240 --> 00:07:05.300 a recurring guest, which is even better. Really? 00:07:06.019 --> 00:07:08.720 Multiple times. Yeah. The source lists, August 00:07:08.720 --> 00:07:12.259 2005, then again, April 2006, and a third time, 00:07:12.319 --> 00:07:16.310 January 2008. OK, three shots on Leno in that 00:07:16.310 --> 00:07:19.829 prime era. That tells you his stuff was connecting. 00:07:20.029 --> 00:07:22.470 It was clean enough, relatable enough for that 00:07:22.470 --> 00:07:25.110 huge middle America audience. That translates 00:07:25.110 --> 00:07:27.709 directly to ticket sales on the road. Absolutely. 00:07:27.910 --> 00:07:30.730 It confirms you're a reliable bet for theaters 00:07:30.730 --> 00:07:33.790 and bigger clubs. And this TV exposure wasn't 00:07:33.790 --> 00:07:36.470 just solo spots. It led to bigger opportunities 00:07:36.470 --> 00:07:39.689 like tours. Exactly. He became part of the blue 00:07:39.689 --> 00:07:43.019 collar comedy tour, The Next Generation. Hosted 00:07:43.019 --> 00:07:45.860 by Bill Engvall. Oh, wow. Joining that franchise. 00:07:45.939 --> 00:07:49.259 That's tapping into a massive built -in audience, 00:07:49.420 --> 00:07:51.519 isn't it? Huge. Strategically, that's brilliant. 00:07:51.720 --> 00:07:54.259 The blue -collar brand had this incredibly loyal 00:07:54.259 --> 00:07:56.600 following. People bought tickets because they 00:07:56.600 --> 00:07:58.920 trusted the name. Being part of that instantly 00:07:58.920 --> 00:08:00.860 put him in front of enormous crowds who were 00:08:00.860 --> 00:08:03.899 already primed to like his kind of humor. A very 00:08:03.899 --> 00:08:06.480 specific, very dedicated demographic, probably 00:08:06.480 --> 00:08:08.899 more valuable long term than just a random viral 00:08:08.899 --> 00:08:11.600 moment. Much more. Reliable ticket buyers. And 00:08:11.600 --> 00:08:13.240 then there was the documentary exposure, too. 00:08:13.399 --> 00:08:15.459 Right. Vince Vaughn's Wild West Comedy Tour. 00:08:15.519 --> 00:08:18.079 That came out around 2008, filmed a bit earlier. 00:08:18.319 --> 00:08:20.740 First shown in 2006, yeah. What's the significance 00:08:20.740 --> 00:08:23.339 of being in something like that? Is it just cool 00:08:23.339 --> 00:08:25.540 or does it serve a career purpose, being seen 00:08:25.540 --> 00:08:28.100 hanging out with Vaughn and those guys? Oh, it 00:08:28.100 --> 00:08:30.720 definitely serves a purpose. In that world, association 00:08:30.720 --> 00:08:33.919 is credibility. Right. Being documented on tour, 00:08:34.159 --> 00:08:36.799 joking around, basically being accepted into 00:08:36.799 --> 00:08:40.240 the inner circle of a major star like Vince Vaughn. 00:08:40.379 --> 00:08:43.700 Yeah. It sends a signal. To who? Agents. Not 00:08:43.700 --> 00:08:46.000 managers. Yeah, exactly. Agents, managers, network 00:08:46.000 --> 00:08:49.120 people, club owners. It says, this guy is legit. 00:08:49.279 --> 00:08:52.220 He's professional. He can handle big tours, big 00:08:52.220 --> 00:08:54.940 venues. He's validated by people already at the 00:08:54.940 --> 00:08:57.080 top. Okay, so it's an industry stamp of approval? 00:08:57.399 --> 00:09:00.240 Pretty much. So this whole period, roughly 2003 00:09:00.240 --> 00:09:03.159 to 2008, it was all about taking that initial 00:09:03.159 --> 00:09:05.779 festival buzz and leveraging it into consistent 00:09:05.779 --> 00:09:08.220 TV appearances, which then built the credibility 00:09:08.220 --> 00:09:10.840 needed for major tours and industry recognition. 00:09:11.220 --> 00:09:13.559 He went from the guy at the door to a known quantity, 00:09:13.700 --> 00:09:16.240 a touring professional, setting things up for 00:09:16.240 --> 00:09:18.340 the next big phase, which really cemented his 00:09:18.340 --> 00:09:21.639 public image. Precisely. The phase where he became 00:09:21.639 --> 00:09:25.320 truly recognizable to almost everyone. Okay, 00:09:25.399 --> 00:09:27.019 so the next big chunk of his career, let's say 00:09:27.019 --> 00:09:30.139 2008 through 2014, this is really where the John 00:09:30.139 --> 00:09:33.159 Caparulo brand gets locked in. And the centerpiece 00:09:33.159 --> 00:09:36.559 of that is undeniably Chelsea Lely. Ah, yes. 00:09:36.879 --> 00:09:39.460 The E! Show. He was on that a lot, wasn't he? 00:09:39.740 --> 00:09:41.960 Constantly. For the entire seven -year run of 00:09:41.960 --> 00:09:44.600 the show, he was a regular recurring face on 00:09:44.600 --> 00:09:47.879 that roundtable panel. Seven years? That's more 00:09:47.879 --> 00:09:49.740 than just occasional exposure. That's becoming 00:09:49.740 --> 00:09:52.460 part of people's daily or weekly routine. Exactly. 00:09:53.049 --> 00:09:55.350 Think about the difference. A five -minute stand 00:09:55.350 --> 00:09:57.730 -up set on Leno is great. People might remember 00:09:57.730 --> 00:10:00.289 your name or a specific joke. Right. But sitting 00:10:00.289 --> 00:10:03.250 on that panel, night after night, for seven years, 00:10:03.490 --> 00:10:06.169 viewers get to know you. Your personality, your 00:10:06.169 --> 00:10:08.549 takes, your reactions, your patents. You're not 00:10:08.549 --> 00:10:10.909 just a comedian doing material. You're a known 00:10:10.909 --> 00:10:13.210 personality. Yeah, you become familiar, like 00:10:13.210 --> 00:10:15.889 someone they kind of know. Totally. It's cemented 00:10:15.889 --> 00:10:17.629 him in the public consciousness in a way stand 00:10:17.629 --> 00:10:20.509 -up specials alone rarely do. Chelsea lately 00:10:20.509 --> 00:10:22.409 was a cultural thing for a while there, and he 00:10:22.409 --> 00:10:25.269 was a core part of it. That show became his main 00:10:25.269 --> 00:10:28.590 marketing platform. And did he leverage that 00:10:28.590 --> 00:10:31.090 platform? Did he use that visibility to do other 00:10:31.090 --> 00:10:33.149 things? Oh, definitely. He was smart about it. 00:10:33.190 --> 00:10:35.129 He diversified. Didn't just rely on Chelsea or 00:10:35.129 --> 00:10:37.710 stand -up. Like, what else was he doing? Well, 00:10:37.769 --> 00:10:40.570 he took on a hosting gig, Mobile Home Disaster, 00:10:40.590 --> 00:10:44.350 on CMT. The source notes, it started in 2008 00:10:44.350 --> 00:10:48.039 and was ongoing. CMT, interesting. Connecting 00:10:48.039 --> 00:10:50.279 back to that blue -collar country audience, maybe. 00:10:50.419 --> 00:10:52.500 Seems likely, doesn't it? Reinforcing that connection. 00:10:52.980 --> 00:10:55.799 Then he also dipped his toe into scripted TV 00:10:55.799 --> 00:10:58.399 acting. He played a character called Brian on 00:10:58.399 --> 00:11:01.019 an ABC sitcom called Work It. It was short -lived, 00:11:01.100 --> 00:11:03.340 apparently. Trying different things. Yeah, and 00:11:03.340 --> 00:11:05.639 maybe most surprisingly, he got into voice acting. 00:11:05.879 --> 00:11:08.620 He voiced a character named Headphone Joe on 00:11:08.620 --> 00:11:11.700 a Disney animated show, Fish Hooks. Voice acting? 00:11:11.899 --> 00:11:14.340 That's a different skill set. It is, but look 00:11:14.340 --> 00:11:17.000 at the strategy here. Hosting on CMT targets 00:11:17.000 --> 00:11:20.240 one audience. A network sitcom tries for broad 00:11:20.240 --> 00:11:23.460 appeal. Voice acting on Disney. That opens up 00:11:23.460 --> 00:11:25.460 a whole different demographic. Kids, families. 00:11:25.700 --> 00:11:28.259 And it gives him experience in animation, which 00:11:28.259 --> 00:11:31.019 becomes important later. Smart. Hedging his bets, 00:11:31.159 --> 00:11:33.720 building different skills, not putting all his 00:11:33.720 --> 00:11:35.639 eggs in the stand -up basket. Exactly. It's career 00:11:35.639 --> 00:11:38.539 management. Building a portfolio. And all this... 00:11:38.750 --> 00:11:41.350 Steady work, this visibility, presumably gave 00:11:41.350 --> 00:11:43.649 him the stability to release his own stand -up 00:11:43.649 --> 00:11:45.409 specials. Yeah, that's when his first big special 00:11:45.409 --> 00:11:49.230 dropped. John Caparulo, Meat Cap, aired on Comedy 00:11:49.230 --> 00:11:53.590 Central December 2008. Meat Cap. Okay. Standard 00:11:53.590 --> 00:11:55.490 Comedy Central release. Pretty standard, yeah. 00:11:55.590 --> 00:11:57.409 And the release strategy was typical for the 00:11:57.409 --> 00:12:01.070 time, too. CD came out February 2009. DVD followed 00:12:01.070 --> 00:12:03.889 in April 2009. How did it do? Commercially? Did 00:12:03.889 --> 00:12:06.350 alright. The album hit number eight on the U 00:12:06.350 --> 00:12:08.909 .S. comedy charts. Solid performance for a Comedy 00:12:08.909 --> 00:12:11.789 Central special. Okay. Standard success. But 00:12:11.789 --> 00:12:13.669 then comes the second album, and this is where 00:12:13.669 --> 00:12:15.049 it gets really interesting, I think. What was 00:12:15.049 --> 00:12:17.769 the second one? Come Inside Me. Released a few 00:12:17.769 --> 00:12:21.330 years later, August, September 2013. And this 00:12:21.330 --> 00:12:23.669 one came out on Netflix. Ah, Netflix. The game 00:12:23.669 --> 00:12:26.289 was changing by then. Right. And the chart performance 00:12:26.289 --> 00:12:29.769 for this album, this is where you see the payoff 00:12:29.769 --> 00:12:32.549 from all that previous work. How so? Did it chart 00:12:32.549 --> 00:12:35.190 higher on comedy? It did hit number two on U 00:12:35.190 --> 00:12:38.690 .S. comedy. Huge success. Great. But it also 00:12:38.690 --> 00:12:41.070 charted on the U .S. country albums chart. Wait, 00:12:41.110 --> 00:12:43.470 what? A comedy album charted on the country music 00:12:43.470 --> 00:12:46.389 chart? Yep. Peaked at number 59 on U .S. country. 00:12:46.590 --> 00:12:50.830 That's bizarre and fascinating. Why? How does 00:12:50.830 --> 00:12:52.830 a stand -up comedy album end up on the country 00:12:52.830 --> 00:12:55.509 charts? This is the proof, right? It confirms 00:12:55.509 --> 00:12:58.610 that the strategy worked. All those years on 00:12:58.610 --> 00:13:01.049 Chelsea lately gave him broad name recognition. 00:13:02.100 --> 00:13:05.200 But the blue -collar tour connection, the CMT 00:13:05.200 --> 00:13:08.299 hosting cake, that built a genuine bridge to 00:13:08.299 --> 00:13:10.840 that heartland, country -leaning audience. So 00:13:10.840 --> 00:13:13.200 his humor, his persona, it resonated with them 00:13:13.200 --> 00:13:16.120 specifically. Seems so. His style is very observational, 00:13:16.179 --> 00:13:18.580 relatable, often about everyday frustrations, 00:13:18.580 --> 00:13:20.820 family stuff. It's grounded, not particularly 00:13:20.820 --> 00:13:23.320 edgy or coastal. It connects with the kind of 00:13:23.320 --> 00:13:24.960 audience that listens to country music, watches 00:13:24.960 --> 00:13:27.240 CMT. He wasn't just playing to the comedy club 00:13:27.240 --> 00:13:29.659 nerds or the lay New York crowds. He was reaching 00:13:29.659 --> 00:13:32.740 the people Bill Engvall reached. Exactly. And 00:13:32.740 --> 00:13:34.620 that country chart appearance is statistical 00:13:34.620 --> 00:13:37.120 proof of it. It shows incredibly deep market 00:13:37.120 --> 00:13:39.379 penetration. That audience is known for being 00:13:39.379 --> 00:13:41.860 really loyal, too. Right. They stick with their 00:13:41.860 --> 00:13:44.200 artists. So charting on both comedy and country. 00:13:44.570 --> 00:13:47.889 That tells you he had arguably the broadest possible 00:13:47.889 --> 00:13:50.809 touring base in the U .S. market at that point. 00:13:51.110 --> 00:13:54.070 Diverse geographically, diverse socioeconomically. 00:13:54.149 --> 00:13:56.889 Wow. Okay. So the visibility phase wasn't just 00:13:56.889 --> 00:13:58.929 about being seen. It was about strategically 00:13:58.929 --> 00:14:02.049 building a connection with a massive, loyal audience 00:14:02.049 --> 00:14:04.289 segment. And that success, that broad appeal, 00:14:04.529 --> 00:14:07.809 set him up perfectly for the next big strategic 00:14:07.809 --> 00:14:10.750 move, taking control. Moving into independence. 00:14:11.129 --> 00:14:14.070 OK, so Chelsea Lately ends in 2014 after that 00:14:14.070 --> 00:14:17.129 long seven year run. What happens next? Does 00:14:17.129 --> 00:14:19.409 he look for another panel show, another network 00:14:19.409 --> 00:14:22.340 gig? Nope. He makes a really clear, decisive 00:14:22.340 --> 00:14:25.259 pivot almost immediately. He shifts away from 00:14:25.259 --> 00:14:27.460 relying on traditional TV for his primary output 00:14:27.460 --> 00:14:30.000 and starts building his own thing, his own content 00:14:30.000 --> 00:14:31.659 world. This is where it gets really modern, right? 00:14:31.720 --> 00:14:33.759 Taking control of distribution. Exactly. And 00:14:33.759 --> 00:14:35.639 his first move was pretty innovative, especially 00:14:35.639 --> 00:14:38.399 for 2014. He launched something called Caplets. 00:14:38.639 --> 00:14:41.399 Caplets? Like little pills of comedy. Kind of, 00:14:41.399 --> 00:14:45.360 yeah. The concept was a brand new set of professionally 00:14:45.360 --> 00:14:48.559 filmed stand -up comedy released every single 00:14:48.559 --> 00:14:51.950 month. 30 days, new material. Every month. That's 00:14:51.950 --> 00:14:54.169 a demanding schedule. Most comics wait years 00:14:54.169 --> 00:14:56.549 between specials. Right. But think about the 00:14:56.549 --> 00:14:59.830 advantages. Why do this instead of waiting for, 00:14:59.970 --> 00:15:03.450 say, another Netflix deal? Well, you're constantly 00:15:03.450 --> 00:15:05.330 putting out new stuff, keeping your name out 00:15:05.330 --> 00:15:07.629 there, staying relevant between big projects. 00:15:07.870 --> 00:15:09.970 That's part of it. It manages audience expectation. 00:15:10.129 --> 00:15:13.730 They know they'll get fresh, quality stuff. It 00:15:13.730 --> 00:15:16.210 also means he's constantly working out and refining 00:15:16.210 --> 00:15:18.529 material in front of an audience, not just hoarding 00:15:18.529 --> 00:15:20.710 it for two years. Like a public workshop, almost. 00:15:20.950 --> 00:15:23.269 Sort of. Yeah. But the biggest thing, strategically, 00:15:23.690 --> 00:15:27.230 ownership and distribution. Ah, where were these 00:15:27.230 --> 00:15:29.730 caplets released? He filmed them himself, or 00:15:29.730 --> 00:15:32.190 his team did, at well -known clubs like the Comedy 00:15:32.190 --> 00:15:34.610 and Magic Club in Hermosa Beach and the Ice House 00:15:34.610 --> 00:15:37.210 in Pasadena, good venues. And then he released 00:15:37.210 --> 00:15:39.990 them for free on his own website. For free? On 00:15:39.990 --> 00:15:43.070 his site? Yeah. Bypassing networks, bypassing 00:15:43.070 --> 00:15:45.409 YouTube monetization initially maybe. Yeah. Just 00:15:45.409 --> 00:15:47.389 direct to the fans. So he controls the content 00:15:47.389 --> 00:15:49.870 100 percent. No network notes, no platform rules. 00:15:50.049 --> 00:15:53.370 And he owns the footage. Exactly. He owns the 00:15:53.370 --> 00:15:55.889 IP. He controls the data, the fan relationship. 00:15:56.129 --> 00:15:58.809 He essentially became his own mini comedy network 00:15:58.809 --> 00:16:01.370 delivering directly to his audience. That's a 00:16:01.370 --> 00:16:04.950 huge shift in power from being just a performer 00:16:04.950 --> 00:16:07.370 for hire. That's the producer mindset kicking 00:16:07.370 --> 00:16:10.399 in. Okay, so the Caplets were about frequent 00:16:10.399 --> 00:16:13.419 owned content. Was that the only independent 00:16:13.419 --> 00:16:15.580 thing he was doing? No, that was just the start. 00:16:15.779 --> 00:16:18.620 Around the same time, also starting in 2014, 00:16:19.159 --> 00:16:21.740 he began developing a much bigger, more ambitious 00:16:21.740 --> 00:16:25.320 independent project, Cartoon Comic. Cartoon Comic, 00:16:25.399 --> 00:16:27.720 what's that? It's basically an animated series 00:16:27.720 --> 00:16:31.200 concept based directly on his own life. Being 00:16:31.200 --> 00:16:33.759 a working comedian, but also a husband and eventually 00:16:33.759 --> 00:16:36.620 a father, leveraging that whole relatable persona 00:16:36.620 --> 00:16:38.580 we talked about. An animated series, that's a 00:16:38.580 --> 00:16:40.679 big undertaking. And it connects back to that 00:16:40.679 --> 00:16:42.399 voice acting he did for Disney, right? Makes 00:16:42.399 --> 00:16:44.620 perfect sense, doesn't it? He's got the experience. 00:16:44.820 --> 00:16:47.279 He's got the established persona. Now he's building 00:16:47.279 --> 00:16:49.460 an intellectual property around it that he can 00:16:49.460 --> 00:16:52.259 potentially own and control long term. Has he 00:16:52.259 --> 00:16:55.029 actually made it? Or is it just an idea? He's 00:16:55.029 --> 00:16:57.210 been actively developing it in multiple ways. 00:16:57.389 --> 00:16:59.309 The source mentions he's written a comic book 00:16:59.309 --> 00:17:01.450 series based on the concept. Okay, multimedia. 00:17:01.809 --> 00:17:04.390 Yeah. And he's also independently produced several 00:17:04.390 --> 00:17:07.349 animated stand -up shorts using the cartoon comic 00:17:07.349 --> 00:17:09.410 style and put them on his website and YouTube. 00:17:09.670 --> 00:17:12.190 So he's building the world, testing the concept, 00:17:12.309 --> 00:17:14.690 creating assets. It's not just waiting for someone 00:17:14.690 --> 00:17:17.509 to greenlight it. He's actively making it happen 00:17:17.509 --> 00:17:19.789 himself, piece by piece. That's the independent 00:17:19.789 --> 00:17:22.809 creator model. Parallel processing, keep to it. 00:17:22.890 --> 00:17:25.990 keep doing the caplets, but also steadily build 00:17:25.990 --> 00:17:29.130 your own long -term IP asset on the side. And 00:17:29.130 --> 00:17:32.049 this focus on his personal life, his family, 00:17:32.109 --> 00:17:35.450 as the basis for the cartoon. That seems like 00:17:35.450 --> 00:17:37.910 a deliberate brand extension. Absolutely deliberate. 00:17:37.990 --> 00:17:39.650 And you see it reflected in his other independent 00:17:39.650 --> 00:17:42.029 stuff, too, like his radio show, The Madcap Hour. 00:17:42.130 --> 00:17:43.990 He had a radio show, too. Yeah, intermittently 00:17:43.990 --> 00:17:46.670 hosted. And who were his co -hosts? His wife, 00:17:46.849 --> 00:17:49.710 Jamie Caparulo, and another comedian, Mark Ellis. 00:17:49.990 --> 00:17:53.210 His wife. OK, so really leaning into the family 00:17:53.210 --> 00:17:56.049 domestic angle as part of the public brand. Totally. 00:17:56.109 --> 00:17:58.890 It makes the cartoon comic concept feel even 00:17:58.890 --> 00:18:00.910 more authentic because people are literally hearing 00:18:00.910 --> 00:18:03.630 him interact with his wife on the radio show. 00:18:08.570 --> 00:18:12.329 And the sources track this integration of personal 00:18:12.329 --> 00:18:14.470 life really clearly, don't they? Like, even the 00:18:14.470 --> 00:18:17.150 proposal. Yeah, it's quite specific. He announced 00:18:17.150 --> 00:18:19.269 the engagement on Chelsea Lately in November 00:18:19.269 --> 00:18:22.309 2010. But the actual proposal happened October 00:18:22.309 --> 00:18:25.589 29, 2010, at the Comedy and Magic Club, his workplace, 00:18:25.809 --> 00:18:28.109 essentially. They're blurring the lines. Professional 00:18:28.109 --> 00:18:30.809 venue, personal moment, announced on a national 00:18:30.809 --> 00:18:34.769 TV show. And the wedding. May... 2012, where 00:18:34.769 --> 00:18:37.609 was it held? At a tavern near Kent State University, 00:18:37.950 --> 00:18:40.829 their alma mater. Back to the Ohio roots. Grounding 00:18:40.829 --> 00:18:43.470 the success in that relatable origin story. It's 00:18:43.470 --> 00:18:45.789 very consistent branding. Extremely consistent. 00:18:46.529 --> 00:18:48.890 And then comes the baby news. How did they handle 00:18:48.890 --> 00:18:51.230 that publicly? Again, using their own platform. 00:18:51.970 --> 00:18:54.410 Jamie, his wife, revealed a pregnancy on their 00:18:54.410 --> 00:18:57.730 other podcast, Domestic Disputes. Episode 26, 00:18:58.089 --> 00:19:00.750 October 2014. They had another podcast called 00:19:00.750 --> 00:19:03.619 Domestic Disputes. Oh, it seems so. And then, 00:19:03.680 --> 00:19:06.500 a month later, podcast number 28, November 2014, 00:19:06.980 --> 00:19:10.019 they reveal the gender and the name of girl, 00:19:10.220 --> 00:19:14.160 Madden J. who was then born in May 2015. Wow. 00:19:14.319 --> 00:19:16.720 So they used their own podcast as like the official 00:19:16.720 --> 00:19:19.140 announcement channel for major life events. Why 00:19:19.140 --> 00:19:21.680 not? It's intimate. It's direct to their core 00:19:21.680 --> 00:19:24.779 fans. It generates content. And it constantly 00:19:24.779 --> 00:19:27.460 reinforces the real life basis for the cartoon 00:19:27.460 --> 00:19:30.240 comic project. Everything connects. It's a self 00:19:30.240 --> 00:19:32.819 -sustaining content loop. Life happens. They 00:19:32.819 --> 00:19:35.119 talk about it on the podcast. The podcast deepens 00:19:35.119 --> 00:19:37.700 the fan connection. The life events provide material 00:19:37.700 --> 00:19:41.269 for a stand -up. And the cartoon becomes comes 00:19:41.269 --> 00:19:44.269 the owned IP. It's really smart. This whole independent 00:19:44.269 --> 00:19:46.690 phase, it's not just about making stuff. It's 00:19:46.690 --> 00:19:48.789 about building an integrated ecosystem where 00:19:48.789 --> 00:19:51.450 his life, his work, and his own IP all feed each 00:19:51.450 --> 00:19:53.569 other. But doing all that, the caplets, developing 00:19:53.569 --> 00:19:56.250 animation, multiple podcasts, plus touring that 00:19:56.250 --> 00:19:58.630 takes a lot of time and energy, how do you sustain 00:19:58.630 --> 00:20:01.829 that level of independent output? Ah, well, that's 00:20:01.829 --> 00:20:03.390 where the final piece of the puzzle comes in. 00:20:03.660 --> 00:20:05.779 The move that provides the stability needed to 00:20:05.779 --> 00:20:08.160 fuel all this independent ambition. The residency, 00:20:08.380 --> 00:20:11.160 right. The Las Vegas residency. That feels like 00:20:11.160 --> 00:20:14.099 the ultimate goal for a certain kind of established 00:20:14.099 --> 00:20:16.799 comedian, doesn't it? Stability. It's the holy 00:20:16.799 --> 00:20:19.980 grail for many. Yeah. Predictability, less travel, 00:20:20.160 --> 00:20:23.380 solid income. And Caprillo made that leap in 00:20:23.380 --> 00:20:25.660 2018. Who offered it? How did it come about? 00:20:26.140 --> 00:20:28.299 Caesars Entertainment made the offer, which is 00:20:28.299 --> 00:20:31.000 a major player. They gave him a weekly residency 00:20:31.000 --> 00:20:34.150 show. And he's still doing it now. Yep. consistently 00:20:34.150 --> 00:20:37.529 performing John Caparulo's madcap comedy five 00:20:37.529 --> 00:20:40.710 nights a week at Harrah's Las Vegas. Five nights 00:20:40.710 --> 00:20:44.589 a week, every week at Harrah's. Okay, let's break 00:20:44.589 --> 00:20:46.549 down the strategic advantage of that compared 00:20:46.549 --> 00:20:49.150 to the old model of constantly being on the road, 00:20:49.170 --> 00:20:51.769 flying city to city. It's night and day, really. 00:20:51.930 --> 00:20:55.250 First, the obvious, financial stability. You 00:20:55.250 --> 00:20:57.089 have a contract. You have a guaranteed paycheck 00:20:57.089 --> 00:20:59.490 five nights a week. You're not constantly worrying 00:20:59.490 --> 00:21:01.490 about ticket sales in Des Moines next Tuesday. 00:21:01.609 --> 00:21:05.130 Takes away huge pressure. Huge. Second, eliminating 00:21:05.130 --> 00:21:08.309 the grind of travel. The source mentions he resides 00:21:08.309 --> 00:21:10.869 in Calabasas, California and Las Vegas, Nevada. 00:21:11.210 --> 00:21:14.190 So he's either home or a shore hop away. No more 00:21:14.190 --> 00:21:17.069 red eyes, no more crappy airport hotels multiple 00:21:17.069 --> 00:21:19.329 times a week. That saves so much physical and 00:21:19.329 --> 00:21:21.529 mental energy. The burnout for touring comics 00:21:21.529 --> 00:21:24.529 is legendary. It's brutal. So the residency drastically 00:21:24.529 --> 00:21:27.430 reduces that wear and tear. He gets to sleep 00:21:27.430 --> 00:21:29.869 in his own bed more often, be present with his 00:21:29.869 --> 00:21:32.990 family, which, as we saw, is central to his brand 00:21:32.990 --> 00:21:35.250 and content now. So the residency isn't just 00:21:35.250 --> 00:21:37.690 an endpoint like making it. It's actually an 00:21:37.690 --> 00:21:40.009 enabler for the other stuff. That's exactly how 00:21:40.009 --> 00:21:42.410 I see it. The Vegas show is the reliable high 00:21:42.410 --> 00:21:45.009 income anchor. It's the steady job. And because 00:21:45.009 --> 00:21:47.410 it's geographically fixed and predictable, it 00:21:47.410 --> 00:21:50.009 frees up his non -stage time and energy. Energy 00:21:50.009 --> 00:21:52.049 he can then pour into the independent projects? 00:21:52.269 --> 00:21:54.299 Precisely. He now has the financial security 00:21:54.299 --> 00:21:57.500 and the mental bandwidth to really focus on developing 00:21:57.500 --> 00:22:00.079 cartoon comic, to work on the animation, the 00:22:00.079 --> 00:22:02.119 writing, the business side of it. He doesn't 00:22:02.119 --> 00:22:03.799 have to take every single road gig just to pay 00:22:03.799 --> 00:22:06.700 the bills. He can be more selective. He can invest 00:22:06.700 --> 00:22:09.519 time in the long -term IP play because the short 00:22:09.519 --> 00:22:11.460 -term finances are secured by the residency. 00:22:11.819 --> 00:22:15.079 That's the strategic brilliance of it. The residency 00:22:15.079 --> 00:22:17.720 provides the foundation that allows him to pursue 00:22:17.720 --> 00:22:21.200 the ultimate goal. Owning and controlling his 00:22:21.200 --> 00:22:24.500 own successful intellectual property. It buys 00:22:24.500 --> 00:22:27.460 him the time and resources to take bigger creative 00:22:27.460 --> 00:22:29.980 swings. Okay. So if we zoom out and look at the 00:22:29.980 --> 00:22:33.220 whole arc again, it really does feel like a deliberate 00:22:33.220 --> 00:22:36.279 step -by -step execution of a plan. It really 00:22:36.279 --> 00:22:39.220 does. You see the progression. Start with the 00:22:39.220 --> 00:22:41.740 regional grind. Learn the craft. Okay. Move to 00:22:41.740 --> 00:22:45.160 L .A. Prioritize proximity and hustle the doorman 00:22:45.160 --> 00:22:48.230 years. Right. Get the big break. Just for laughs, 00:22:48.369 --> 00:22:51.210 2003. Capitalize immediately with TV. I know, 00:22:51.329 --> 00:22:53.990 Kilborn. Build mass market visibility and brand 00:22:53.990 --> 00:22:56.470 recognition over a sustained period. Chelsea 00:22:56.470 --> 00:22:58.670 Lately. For seven years. Goosehole branding phase. 00:22:59.029 --> 00:23:01.170 Prove your broad audience connection. The Country 00:23:01.170 --> 00:23:04.029 Chart. Unexpected proof. Then, the moment network 00:23:04.029 --> 00:23:07.009 support potentially wanes, pivot hard to independent 00:23:07.009 --> 00:23:09.210 ownership. Caplitz Cartoon Comic Development. 00:23:09.390 --> 00:23:11.890 Taking control. And finally, secure the stable 00:23:11.890 --> 00:23:15.039 high -income anchor. the Vegas residency, to 00:23:15.039 --> 00:23:17.400 fund and enable the long -term independent IP 00:23:17.400 --> 00:23:20.740 goals. Wow. Laid out like that, it's a blueprint. 00:23:21.220 --> 00:23:24.279 He went from being a performer hoping for gigs 00:23:24.279 --> 00:23:27.039 to being the CEO of Caparulo Inc. Pretty much. 00:23:27.200 --> 00:23:29.640 It's about leveraging exposure when you get it, 00:23:29.640 --> 00:23:32.000 building an audience, then using the stability 00:23:32.000 --> 00:23:34.640 you've earned to take full control of your creative 00:23:34.640 --> 00:23:37.140 and financial future. A powerful model for anyone 00:23:37.140 --> 00:23:40.259 in a creative field, really. Hashtag Chaga Outro. 00:23:40.720 --> 00:23:43.579 So, yeah, just to wrap up the key takeaways here, 00:23:43.740 --> 00:23:47.059 we saw phase one was all about that grind and 00:23:47.059 --> 00:23:49.019 proximity being there, even if it's tough, like 00:23:49.019 --> 00:23:50.880 the doorman gig. Right. Access over immediate 00:23:50.880 --> 00:23:53.779 comfort. Phase two showed how a single big break, 00:23:53.960 --> 00:23:56.799 like that 2003 festival, needs immediate follow 00:23:56.799 --> 00:23:59.460 through with TV appearances to build real bankability. 00:23:59.779 --> 00:24:01.920 You got to strike while the iron's hot. Phase 00:24:01.920 --> 00:24:03.819 three, those seven years on Chelsea, that was 00:24:03.819 --> 00:24:06.839 about embedding the brand, becoming a known personality, 00:24:07.059 --> 00:24:09.779 and proving that crossover appeal. Remember the 00:24:09.779 --> 00:24:12.039 country chart. Can't forget the country chart. 00:24:12.240 --> 00:24:15.000 And phase four, the pivot to independence with 00:24:15.000 --> 00:24:17.700 the Capleton cartoon comic. That's the crucial 00:24:17.700 --> 00:24:20.660 step towards owning your own destiny, not relying 00:24:20.660 --> 00:24:23.240 on gatekeepers. Which is all supported now by 00:24:23.240 --> 00:24:25.940 the stability of phase five, the residency. Exactly. 00:24:26.539 --> 00:24:29.619 So for you listening, what's the big lesson from 00:24:29.619 --> 00:24:32.440 tracing a career like Caparulo's? I think it 00:24:32.440 --> 00:24:34.740 really highlights that fundamental shift you 00:24:34.740 --> 00:24:37.539 need to make. Yeah. You have to move beyond just 00:24:37.539 --> 00:24:40.279 being a performer, hoping someone hires you. 00:24:40.339 --> 00:24:42.440 Waiting for the phone to ring. Yeah. Yeah. And 00:24:42.440 --> 00:24:44.119 become the producer, the one who creates the 00:24:44.119 --> 00:24:46.660 opportunities, owns the content and builds their 00:24:46.660 --> 00:24:49.259 own economic foundation. It's about taking control 00:24:49.259 --> 00:24:51.339 of the means of production, essentially. Right. 00:24:51.480 --> 00:24:54.019 Which leads us to that final provocative thought 00:24:54.019 --> 00:24:58.579 for you to consider. successful Vegas residency 00:24:58.579 --> 00:25:01.500 providing that solid base that time that money 00:25:01.500 --> 00:25:04.740 and we know he's channeling that stability into 00:25:04.740 --> 00:25:07.759 developing cartoon comic this very personal animated 00:25:07.759 --> 00:25:10.599 project based on his life as a comic husband 00:25:10.599 --> 00:25:13.599 father he uses his voice skills leans into his 00:25:13.599 --> 00:25:16.259 relatable brand so based on everything we've 00:25:16.259 --> 00:25:19.359 mapped out today his strategic planning his move 00:25:19.359 --> 00:25:23.599 towards ownership the stability he now has What 00:25:23.599 --> 00:25:25.619 do you think the chances are? Could cartoon comic, 00:25:25.779 --> 00:25:28.019 this independent project he's nurtured for years, 00:25:28.180 --> 00:25:30.880 actually become the next major phase of his career? 00:25:31.119 --> 00:25:33.579 Could that be the thing that breaks through globally? 00:25:33.799 --> 00:25:36.819 A new media success story that he owns, lock, 00:25:36.960 --> 00:25:39.220 stock, and barrel, all built on the back of that 00:25:39.220 --> 00:25:42.019 Vegas anchor? It's the ultimate independent dream 00:25:42.019 --> 00:25:44.900 funded by the ultimate steady gig. Something 00:25:44.900 --> 00:25:46.839 to think about. Definitely something to think 00:25:46.839 --> 00:25:49.119 about. Thanks for diving deep with us today into 00:25:49.119 --> 00:25:51.259 this fascinating career blueprint. Our pleasure. 00:25:51.440 --> 00:25:53.059 We'll see you next time on The Deep Dive.