Recently, I had the chance to sit down with Tony Gasparro, Founder & CEO of West Vegas Media Group and both a member of Chad Nicely’s Entourage Mastermind and POD group known as The Sensational Six. Being users of Nicely’s incredible newsletter publishing software known as Letterman, our conversation quickly became focused on how Tony built The 215 Insider into a bold, unapologetic media voice in West Vegas.
Known for his “chaos and scars” approach, Tony thrives on speed, grit, and raw authenticity. For him, Letterman isn’t just a newsletter tool, it’s a battering ram for attention. By combining TikTok, SEO, and his newsletter into one “control tower,” Tony has transformed cultural drops into loyal subscribers and turned disruption into his signature brand of influence.
Join Tony and I as we discuss his powerful Local Newsletter The 215 Insider, what makes it different, read and highly awaited from issue to issue.
Carol: Every member of the Sensational Six brings something different to the group. What do you feel is your contribution, whether it’s skills, perspective, or experience that not only supports the newsletter’s success but also helps us stand out as a POD?
Tony: I bring the chaos and the scars. I’m the guy who screws up loud, gets knocked flat, and still keeps running until the marathon’s done. My whole thing is taking pain and flipping it into firepower, building machines people can’t ignore. That’s The215Insider.com. The West Vegas media beast already loose in the streets. I’m not here to blend in, I’m here to stir it up. Love me or hate me, just don’t sit in the middle like a loser.
Carol: That’s powerful! Could you share a quick example of when this ‘chaos and scars’ approach actually moved the needle for The 215 Insider, maybe a moment when your bold style got real traction?
Tony: Yeah, there was a week when every other outlet was posting the same boring event recaps and safe photos. I dropped a raw piece calling out the noise in the Vegas scene, straight, no filter. Half the people trashed it, the other half couldn’t stop sharing it. That single post doubled my subscribers in three days. That’s what happens when you stop playing nice and punch straight through.
Carol: Can you share what first drew you into Chad Nicely’s Entourage and what led you to start using Letterman?
Tony: I didn’t join Entourage to high-five people on Zoom. I joined because I was drowning in noise and needed something sharp enough to cut through it. Chad dropped the tools in my lap, and I turned Letterman into a battering ram. Most people buy software just to tinker with it, I strap it to the empire I’m building and swing for the fences.
Carol: Is there a story or campaign you can share when Letterman was turned into that “battering ram,” where it cut through the noise and got results?
Tony: First time I really swung it, I blasted out a local event campaign, quick and dirty, no polish, pure lipstick on a pig. While everyone else was still “workshopping” their perfect copy, my email was already in inboxes. Result? Hundreds of new subs and calls from local sponsors asking how I am moved so fast. That’s when it clicked: Letterman wasn’t a tool, it was my wrecking ball.
Carol: As you’ve started putting Letterman into action, what’s been the most powerful or even surprising part of the experience for you?
Tony: Honestly, the shock wasn’t the wins, it was how damn fast they came once I stopped hiding behind “perfect.” I used to stall, over-edit, second-guess myself into silence. Then I said screw it, slammed send, and suddenly people were either leaning in or running away, but at least they saw me. Years of faceplants finally paid off, because now Letterman takes all that grind and makes it louder.
Carol: I love the shift from perfection to action. Do you have a specific story or event that initiated the “slam send” that blew up bigger than expected? Something that showed the power of moving fast?
Tony: Oh yeah, Summerlin event drop. I almost didn’t send it because it felt messy, too rough. Hit send anyway. That e-mail ended up one of my most opened, most forwarded blasts ever. That’s when I realized: speed and honesty beat perfection every single time
Carol: Everyone brings their own strengths to the table. What do you feel you’ve brought to Letterman that helped you get results or set you apart?
Tony: Grit you can’t fake. I’ve eaten dirt more times than I can count, and I learned how to turn failure into fuel. That shows up in every word I write. My newsletters aren’t “updates,” they’re frontline dispatches. Letterman is my control tower, syncing TikTok, Instagram, SEO, X, Pinterest, and The 215 Insider into one precise strike. I’m not just sending emails, I’m running air traffic for attention.
Carol: Very strategic. Could you walk us through one example of how you synced all those channels (TikTok, SEO, newsletter, etc.) into one campaign? I think it would make your ‘control tower’ metaphor even clearer.
Tony: Sure. I did a campaign for a Vegas restaurant, dropped a TikTok reel as the teaser, had an SEO article already ranking for that same spot, then hit my list with a Letterman blast tying it together. People saw me on TikTok, Googled the spot, landed on my article, and then it got funneled into the newsletter. That’s what I mean by control tower. That every angle covered, so if you were breathing in Vegas that week, you ran into me.
Carol: Nice Tony, very nice! Subscriber growth is a huge part of Letterman’s success. Outside of Facebook, what have you tried, or are you exploring, to bring in subscribers? How is your approach different from what others are doing?
Tony: Amateurs gamble on one pond and hope for fish. Pros build oceans. While everyone else is begging Facebook for scraps, I built a net that drags from everywhere, TikTok, reels, SEO articles, local domination through The 215 Insider. That’s not list-building, that’s empire building. I don’t collect subscribers, I drop trapdoors into my world. Dodge me today, tomorrow you fall in anyway.
Carol: Great imagery. Has there been a specific channel that’s surprised you with subscriber growth? For example, is TikTok giving you faster traction than SEO, or has one local angle been the real powerhouse?
Tony: Funny enough, the surprise win wasn’t TikTok or Insta, it was local SEO. I put out a couple “hidden gems in Vegas” style posts and they started ranking. People were Googling “what’s happening tonight,” and I was the guy showing up. That pulled in subs way faster than I expected.
Carol: Tony, I have to ask: what drives your passion for entrepreneurship, and how does that show up in your workday?
Tony: Chains. I hate them. I’ve been broke, stuck, ignored, laughed at. Every one of those scars lit a fire that still burns. Entrepreneurship is how I break chains and melt them into weapons. Every day I wake up chasing the same thing: building The 215 Insider into the West Vegas media empire nobody thought could happen, until I made it happen.
Carol: That is so relatable Tony. Could you tell us about one of those ‘chains’ that really lit the fire in you, maybe a personal setback or ‘scar’ that fuels your drive today?
Tony: The worst chain? Being broke and invisible while watching weaker voices win. That stung. Nothing fires you up like being underestimated. That scar fuels everything I do now. Every e-mail, every system, every play is me making damn sure I’ll never be ignored again.
Carol: Powerful. I can relate. Tony, what’s one creative twist or strategy you’ve tried, whether with Letterman or your business, that really made a difference?
Tony: I stopped treating emails like chores and started treating them like cultural drops. Not “here’s your content,” but boom, here’s something you can’t ignore. That’s why people subscribe to The 215 Insider. Not just for updates, but because they know I’m about to pull a stunt, stir the pot, and they want front-row seats. That one shift turned a newsletter into a movement.
Carol: I love this idea of a newsletter as a cultural event. Could you share one of your ‘drops’ that created buzz, such as a stunt or theme that people couldn’t stop talking about?
Tony: Easy, “The Summerlin Takeover.” Instead of just listing events, I wrote it like an underground movement. Big headers, visuals, a vibe like you were joining something exclusive. People spread it in Facebook groups and DMs like wildfire. That was the moment I knew I’d built something bigger than a list. I’d built a culture.
Carol: If someone brand new came to you and asked how to succeed quickly with Letterman, what advice would you give them?
Tony: Burn the manual. Don’t wait, don’t ask, don’t apologize. Unsubscribes aren’t rejection, they’re proof you’re cutting deep. Kill the corporate zombie act and torch the page with your real voice. If people don’t love you or hate you, you don’t exist. Tie Letterman into something bigger, like I did with The 215 Insider, and it goes from “just an email” to a weapon that owns the room.
Carol: Great advice. If you had to boil it down to one sentence for a beginner, the #1 mindset shift they need before they touch Letterman, what would that be?
Tony: Stop waiting, send the damn email.
Carol: What is the legacy you’d like to leave Tony?
Tony: Legacy? I don’t care about comfort, I want disruption. I wanna be the fire in the sky you can’t unsee, the shadow that sticks even when you look away. Play small and you disappear, play raw and you live forever. I’m the Final Boss, you don’t beat me, you remember me, and when it’s all over, my name is still echoing past the event horizon.
Carol: Anything else you’d like to share Tony?
Tony: Don’t mix up noise with presence. Anybody can post, anybody can shout. The real game’s building something that outlives the scroll, something people can’t dodge even if they try. That’s The 215 Insider. That’s me. That’s the energy I drag everywhere I go.
To connect with Tony:
