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AI-Powered PR Pitching & Visibility Systems | Rebecca Cafiero of PitchWell | The Brainiac Blueprint Podcast

  • Acy Rodriguez
  • Mar 31
  • 43 min read

In this episode of The Brainiac Blueprint Podcast, we’re joined by Rebecca Cafiero, Founder and CEO of PitchWell, to break down how PR, visibility, and earned media are evolving fast in the age of AI.


Rebecca shares how she’s building Winsley (PitchWell’s AI publicist), why most pitches fail, and what it takes to earn credibility in a world where content is increasingly automated.


Full transcript below.


🎧 Watch or listen to The Brainiac Blueprint Podcast:

Apple Connect: https://bit.ly/3VMNtlH


⏱ In this episode, we discuss:

00:00 | Intro

03:31 | “I think AI is…”

07:12 | Raising kids in an AI world

18:34 | PitchWell breakdown begins + why PR is gatekept

22:55 | Founder mindset + integrity in pitching

23:31 | PitchWell platform demo

28:09 | Pitch for Good + giving back

33:22 | Closing segment

46:20 | Rapid Fire Questions

51:43 | Open forum: giving back + Pitch for Good program


🔗 Rebecca Cafiero



🔗PitchWell


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Episode Full Transcript:


Kyle: Welcome back to another episode of The Brainiac Blueprint where we discuss the intersection of AI and how it impacts business and the world around us with our esteemed guests.


I am your host Kyle Lambert, founder of LeftBrain AI and Action Hero Marketing. In today's episode, we discuss how to use AI to supercharge your visibility, PR, and even your pitches.


With that being said, today's Brainiac is Rebecca Cafiero. Welcome to the show, Rebecca.


Rebecca: Thank you so much. I'm excited to be here and talk about all things AI.


Kyle: Absolutely. I know you've got a lot of good stuff going on, so I'm excited to jump in.


You are kind of a serial entrepreneur, it seems like. Founder and CEO of The Pitch Club and PitchWell, you do a lot of podcasts. So tell everybody who you are and what you're working on.


Rebecca: Yes. So my name's Rebecca. I say I'm a founder by necessity. I love systems. I love thinking. I love design.


My background over the last, well, I'll say I started in journalism 27 years ago. And after that I have been in strategy, sales. I've always loved storytelling whether it was journalism, marketing, but everything that I've ever built is about taking really powerful ideas and how do you make them more visible? Obviously where can you scale? Where can you create more profit?


And so I have built, I built brands, solo services, went on to run a PR agency, group coaching programs, masterminds. But I don't necessarily call myself a publicist, even though that's very much of what we do and the agency does, but I like to think of myself as a strategist.


I love understanding what someone has to offer, what's their unique thing, how do they need to build credibility to be able to scale that, to get in the right rooms, the right conversations, and how to ideally compound that to create a lot of profit and a lot of impact in the world.


And so, right now, PitchWell, which is, yes, it's what I'm focused on, but I really feel like it's the probably the biggest legacy-building thing I've ever done.


Kyle: Very cool.


Rebecca: Yeah. I mean, well, and I think that's the thing about AI, right? It is the ability to expand what we can do.


And so when I look back, you know, I've had a really cool storied career over the last two and a half decades, but I've never had something that I feel like I've never felt like is so right time and is just the culmination of everything that I've experienced, I've known, I've learned, and I've made mistakes on.


And it's a little bit of an obsession right now. And so I know we're going to talk about that, but it's a visibility operating system that helps founders, business owners, thought leaders, coaches, authors go from being the best kept secret, which is not a unique problem, it's a universal problem, to really stepping into that trusted source or, you know, becoming a go-to expert and doing it without gatekeeping, without having to guess, without having to figure it out on their own, and also in a very small amount of time because, you know, AI is giving us more time, but time is still probably the most precious human resource outside of health.


Kyle: 100%, 100%. That's awesome.


I can feel the passion. It's exciting when you can really think about your legacy and have it feel a little bit more tangible, a little bit more clear in terms of the vision and where you're going. And we can definitely see that coming from you.

So lots to jump into there. Definitely want to keep expanding. But before we do, I would love for you to set the stage. As I told you, all of our guests finish the prompt, "I think AI is," so I'm going to pass that on to you.


Rebecca: I think that AI is here to expand us and not replace us.

You know, yes, we're going to offload repetitive tasks, things that don't require like our brains, our voices, you know, the most strategic, creative parts of us, but I believe the real power of AI is how it amplifies us.


Like for us, our voice, obviously in PitchWell, our vision, our values. It allows us to remove a lot of those excuses and limitations off of us, but it really is to expand the most human parts of us so that that part can lead and not the things that we're not so good at.


Kyle: I love that. I love that.

Are you somebody who typically embraces change? Because something like AI is, you know, there's a lot of change and obviously fear can come with it. And especially something so large, so intrusive, if you will, so disruptive.


So do you typically enjoy a little bit of change, a little bit of chaos, maybe?



Rebecca: I wouldn't just say I enjoy it. My personality type, so on the Enneagram, I am the 7, which is the enthusiast or the visionary. And 7s prioritize novelty, intensity, and experience, and they need all options available at all times, which, I mean, that is exactly what AI is, right? It intensifies whatever you're working on.

What I would say is I wouldn't say I'm like, "Oh my God, AI is all good." I think it's like any other tool in human evolution, which is if used for good, it's incredible. And at the same time, we also need to be aware of where it can also expand things that aren't good.


And so it's just like kind of having that 360 view of where can we utilize it in the ways that are going to, again, forward humankind, forward our lives, and where do we need to be very careful?


Like I have small children, so I'm going to be careful about the access I give them or create guard rails.


But today I was thinking, I was like, I feel like I use my AI really well. Sometimes I talk to my AI. I'm like, like that show Upload. I'm like, "Do you talk to the other ChatGPTs and what would be my usage percentage of you?"


And sometimes I'm like, "No, I'm using it really well." And then there's other times I'm like, "Have I ever asked AI, 'How do I solve our top world problems?'" I haven't. That is a prompt I need to give it.


Kyle: Well, there's that old, you know, marketing joke that, you know, Google knows more about you than like your priest or whatever. You know, I think ChatGPT and AI is becoming that even more so. Like the random questions that get typed in there is insane.



Rebecca: I mean, yeah, you know, some of the most fun prompts are just "Based on everything you know about me, what are my 10 strengths and what are my 10 blind spots?" Things like that. And it's true if you use it as much as I do, which my, what is it, screen time settings tell me. It's probably my best friend - don't tell my husband.


But it is true. And, you know, and again, it's like, what do you want to do with that information, right?


Kyle: I do want to focus on the business stuff, but I always like to ask: you mentioned that you have some children and they are growing up in this AI world. I'm curious how you think about this.


Because, you know, if you were born, call it 20 years ago, you essentially were born knowing how to use a phone, right? And now kids today are basically going to be born knowing how to do prompts or, you know, create apps via AI and things like that.


And to your point, there's a good and a bad side to this. So I'm curious how you approach it just from a mom standpoint.


Rebecca: I think the fear is that we just, we don't know what we don't know. And so if we look back at like when the internet came about, right? Like there obviously would have been huge jumps in technology and ways that it impacted our life, you know, in and outside of that tech.


I think it's even more important now to really focus on like the human values. So like my kids, it's like resilience, like understanding, "How is what I'm doing in any way impacting others?" Those things are not different. It's just more important than ever to rely on those.


But for example, you know, we're in Italy right now. We're doing a sabbatical here. I'm working. My husband is on a true sabbatical because he's a tech founder and he sold his startup.


But when we looked at, what are the things that we prioritize while we're here? It's family time. It is learning the language. That's important because I want to get my citizenship, the rest of them get it. And then the third is developing resilience.

And when we think about AI, one of the things, it is an incredible resource when used as a resource.


And I'll tell you a story. My son and my daughter, you know, they see me using it. In fact, often if they don't believe me, they'll say, "Ask ChatGPT, ask ChatGPT." They want me to fact check. I'm like, "Well, I can get the answer I want depending on what prompt I give it."


But we have a cabin in the woods in Big Sur and my husband and my son were out there probably about two years ago. So my son was about seven and a half at the time. And my husband left with the phone. There is no internet. Sorry, there's no phone reception, but we do have Starlink, so we have internet.


And he said, "I'll be back in like 20 minutes." Well, apparently it was longer than 20 minutes. My son started to get worried. He went to ChatGPT, which he'd never done before. You know, he'd seen us use it, but he'd never used it.

And he said, "Hey, I'm seven and a half. I'm in the woods. There's no one around. My dad is gone. I'm getting worried. What do I do?"


Kyle: I can't imagine the response that he got.


Rebecca: Yeah, it was like, you know, "Stay calm, do this, do this, do this." And I was like, wow.


I mean, first of all, I was really excited to see him be resourceful and use an incredible tool. And it kept him from spiraling. And my husband got back like 10 minutes later.


But now, you know, we're in Italy and they're doing homework. And, by the way, they're in school all in Italian. He was like, "Hey mom, can I use your phone?" Because he can take a photo with ChatGPT and say, "What do am I not understanding here?"


And actually we're finding that utilizing, and again I'm saying ChatGPT, any LLM here, right, we're finding that actually the LLMs are way better than a Google Translate. It helps us with nuances. Like, you know, my Italian is okay, it's conversational, but when I am trying to understand like cultural norms and nuances or local speak because we're in Sicily, it understands it and it's so helpful.

So I think my kids are seeing it as an incredibly, incredibly great tool. And again, it's our job as parents to give them the values. The amazing thing about ChatGPT is we're utilizing that to help us be more effective parents.


I actually have a blueprint built for my family. And no, this goes both science and woo. I have each of my family members' Enneagram types, including their tri-types, which is like the deep dive. I have their human design type, their birth charts, and their Ayurvedic types all in a family blueprint.


And so when I say, "Hey, I'm having this challenge with my son and I'm triggered and I want to respond in a way that he can hear and communicate so I can be really effective," it looks at his information and it helps me deliver a message that I can deliver authentically, that he's going to receive. I feel like it's made me a 10x parent.

I mean, 10x of what I could have been on my own. But you have to have the curiosity to do that.

Even down to like some of the littlest things, like we used to come home from school, it's like a 10-minute walk, and I'd have the tutor there at 2:15. And they each get an hour of tutoring with an Italian tutor.

And he was really, my son specifically, was really resistant. And I'm like, you know, this is a problem. So, I asked my family blueprint, I'm like, "What do I need to do?" And it's like, based upon his type, he needs more downtime in between. "Have the tutor start at 2:30. Have a snack. And from 2:15 to 2:30 while they're having their snack, let them play a board game."

And so I bought wooden board games. Fifteen minutes changed the game of having that kind of in-between break.

So again, these are the things for AI. I'm not just using it to build, you know, an AI PR media tech company. I am using it to be a more effective human in the way I communicate with people I love.


Kyle: That is incredible. That is one of the coolest examples that I've heard because, you know, we talk about how it's using or impacting business. But of course there's personal real-life applications as well.

You know, I've been getting excited because I'm trying to play around with it to help my, I was mentioning this in the last episode, to help my fantasy sports teams, and here you are becoming a better mom. I'm like, "Oh, wow. I really got to step up my stuff." And not, I mean CEO too, right?


Rebecca: Right.


Kyle: So, I mean, and again, please understand, like we don't want to get rid of creative thinking. And often I'll come in and I'll say, "Here's kind of what I've done on my own. What am I not asking? What am I not thinking of?" Before I'm just like "Give me the answer."


But even like our developer is an Enneagram 5. He's a massive introvert. And so I am a massive extrovert. And so we have very different communication systems, value systems, priorities, like what motivates us.


So I'm going in, I'm like, "Hey, I got to have this conversation. What's the best way for me to communicate this in a way that is going to get his buy-in?" So it also works as a leader too.


Kyle: Very, very cool.

You seem like a very emotionally intelligent person. You're deep into the personalities and everything. And again, it's just expanding that, to your point earlier. It's very cool to see.


Rebecca: Well, because before, you know, and I think this is the power of AI, is before, I mean, I was, and I'm not against paying experts. I mean, I love experts. That's what I'm building a platform for, but I, you know, I'd have one expert here and one expert here and one expert here and I'd be getting these pieces and I would be trying to assimilate them as the hub, which is not my strong point.

And that's what, you know, AI can do for us is it can bring in those things and allow us to navigate in a way that's useful for us.


Kyle: Very cool. Very cool.

So you have this journalism background. You have, clearly we'll call it a passion in terms of personality types and who everybody kind of is and how they operate. How do you translate that into, you know, value from a PR standpoint, maybe a content standpoint, a podcast standpoint? You know, how do you marry all of those? Because they're kind of similar but different in different ways as well.


Rebecca: So, I like to call it visibility. And so, visibility. Visibility, by the way, I used to say everyone hates sales. Not everyone - salespeople don't hate sales - but you know, business owners, like, "Oh, I'm not in sales."


And one of the, I'd say the best lessons I taught my husband, because he is an engineer by trade, is how to become a salesperson. I'm like, "You're never going to sell a company unless you learn how to sell." You can't sell, you can't raise funds if you can't sell your vision, right? And you can't sell the company, you can't sell your customers. You know, all of the things, like that is sales. And sales just really is fitting people into an opportunity to see if your product, service, or offering can create whatever the transformation that they want.


And so when we think about all these things, what we're really talking about is visibility. Without visibility, impact doesn't get created. And sometimes visibility is small. It's just being in the right room with two people. And sometimes visibility is, you know, if you're trying to, like what we're doing, launching a SaaS platform, we need millions of users to create the impact that we want.


So when you redefine that as visibility, the first thing, a lot of people struggle to be visible because they feel performative.


And so this, we're going to go a little bit more to like, I don't want to call it woo, like early childhood psychology. What is our innate desire as a human? It is to be seen and heard and valued.


Kyle: I'm a marketer so I love this stuff. So keep going. I love it.


Rebecca: Okay, perfect. So you know, I mean, yes, like we, Maslow's pyramid or Maslow's hierarchy, like we need food, we need shelter, you know, air, water, all those things. But you know, self-actualization, like part of that is, again, being seen and heard and valued.


So when I was really focusing on founder coaching, you know, outside of just business metrics and growth, one of the things I looked at is, where is someone struggling to show up? Now, I'm not talking about like showing up for a reel, but it's the same mechanism. It's like, where are they struggling to show up in their genius? And why is that?


Why can't they communicate the things that they're passionate about? Why can't they communicate the things that they're knowledgeable about? And it usually is because someone isn't locked into - it's like a Venn diagram. Ikigai is really what it is, if anyone's ever heard of that.


Have you heard of Ikigai?


Kyle: I'm not sure. No, it's not ringing.


Rebecca: It's a Japanese term. It's I-K-I-G-A-I.


Kyle: Okay.


Rebecca: Yeah. I-K-I-G-A-I. And before that, I used to say, like, it's your lived experience, right? So that's a type of expertise, maybe your education or training, and then what is your passion? And it's kind of that through-line.


Because someone else could have a very similar bio. They could have a similar education. They could theoretically have had the same job. But when you bring in the uniqueness of your passion point, it is going to totally change why you do what you do, for who you do it.


And so instead of like trying to be a version of someone else or like, I mean, yes, if someone is doing something successfully, look at what's working, but don't try to copy someone because they have different motivations.


So the more someone can go into that unique point, in Ikigai it's your center point of what the world needs, what you're good at, what you love, and what you can get paid for. And then that center point is called Ikigai and it literally means "reason for being."


So we have to start there for visibility because that's actually sustainable for a human.


And so when you're like, "Okay, I'm clear on who I am, what I'm doing, where I create impact and where I can be compensated," if you, in Taylor Swift's words, like, "If we're entering an era of visibility," this is no longer what it was five, seven, eight years ago of likes and followers and like going viral and dancing on TikTok. I mean, that might still be out there. I don't have TikTok because I'm like, that's probably too addictive. I don't need that distraction.


When we think about visibility, especially authentic visibility as leverage, it's our reputation. It is market signal for founders. It's a currency, right? And so being seen isn't the goal. It's being trusted, or it's being seen by the right people in a way that we show up in our expertise.


And so there's been this shift over the last, I'd say like, really I've seen it the last one to two years from like this kind of fame and clout chasing to authority building.


Kyle: 100%.


Rebecca: And so visibility today means like, hey, you should quote me, but it's not like, "Oh, because I just want a logo." Yeah, logos are helpful. It's more of like, "I have something to teach or offer," and/or, "You should buy from me," but not, you know, just because I want your dollar. It's because my perspective or what I've built is proven and valuable.


And so in short, influence is earned. It's no longer about the performing, the performative. And I think really like smart in-the-know founders are treating visibility as an asset, not like a to-do that's by accident or an ego metric. It's like, actually, this is an asset for me that is really required to go where I want to go.


Kyle: Well, that makes so much sense and I totally agree. I think a lot of people have, you know, there's impostor syndrome and things that they need to overcome to be able to get their authority and their passion out there. And I can see how that directly then translates into what you're doing with PitchWell to help them kind of get that message out, build that authority where there might be some trepidation or fear or doubt, whatever it may be, to then be more successful with their pitches, with, you know, getting that passion out there. So, I can see that linear kind of progress.


So, I think this would be a good time. Let's jump into PitchWell. If you don't mind, give us a rundown of what it does. I don't know if you're prepared to do…


Rebecca: No, I would love to do it.


Kyle: That'd be awesome.


Rebecca: Let me, before I, before I… I'm going to show you the platform. I want to give just a little bit of background of, like, one, because PR has been so gatekept that if most people that aren't at seven figures are not going to be able to afford PR, traditional PR. And I, over the years, you know, before AI, I taught DIY PR programs.


So my little origin story is, you know, I'd done journalism for a few years. I worked as a reporter at a daily paper many, many, many years ago when print media was like still print media was king. And then I went into corporate. I was VP of sales and marketing and then I became an entrepreneur 11 years ago.


And I actually, about three years into entrepreneurship, I'm like, I would like, I want to be seen as more of an expert. I know I'm good at what I do. I know I'm getting results. And so I interviewed PR agencies, but none of them could answer the question I knew as someone that had a lot of sales experience, which is, "How does this lead to metrics, KPI growth? How is this going to lead to either, you know, for me at the time it was email list growth, it was higher conversion rate, it was consultations."


But for founders that could be like click-through, that could be again email list growth, whatever that metric is that's important. And so I started doing it on my own and then I started teaching it because I was like, "Oh, this works unbelievably."


But even in DIY, the problem was that it was so time intensive, which obviously AI is changing.


So the shift is, one is PR used to be gatekept, or if you did it on your own, it was just such a beast.


And so now that it's becoming more guided, LLMs have like, they've democratized search logic, right? Journalists are using AI to search faster through their sources or their pitches. And so if a pitch doesn't match like the search intent, you don't get seen.


And so what we've done is, in PitchWell, well, before building PitchWell, I had all these DIY courses, workflows, you know, all of these different things. But again, they were resources.


And when someone used them, they had to first learn how to do it. They had to learn, "Why is this important? What does a good pitch look like? What does the process of going out and finding the journalist's beat or the, you know, for you, podcasters, I need to go look at their show notes or I need to listen to some episodes." Like they needed to do all these things.


And so if you think about like pitching, like if I'm going to pitch you, it could be hours of research to formulate a good pitch. And we know because you and I are both podcast hosts, there's a lot of terrible pitches.


Kyle: Terrible. Yeah. I mean, I would say 90% of them are pretty terrible. And even the ones that aren't terrible aren't usually very personalized, right?


Rebecca: Right.


And so what we've done is, when I asked myself, "How do I take all this proprietary information that I've created over the years, knowing, I think courses are dead?" I mean, I know there's still some people, but I looked at the rate in my, not even my courses, my courses were very driven by action.


I used a learning designer from Stanford who had worked with like J.Lo and Tyra Banks and, oh my gosh, Gary Vee, to make sure… I was like, "I want to make sure that when someone gets on my course, my rate of completion is higher than you."

But the average in the market is 3% of people finish courses.


Kyle: Wow. I did not…


Rebecca: It's terrible.

And what that means, and I'm not like, like, yes, all of us want to make money, but for me, I'm like, if I'm making money, but the person buying isn't getting the transformation, I feel like I haven't served them.


Right. That's what we want. We want people to use the thing and then tell everyone they know about it and then have referrals.


So when I looked at that issue, I was like, "Okay, how can I utilize AI to make the tension, like to reduce the tension greatly?" And so we built PitchWell.


And so what PitchWell is, is a visibility operating system. And we've trained Winsley, and Winsley's like your virtual or AI publicist, on editorial strategy, not just like, "How do you structure a pitch?" We've really trained it on like, "What does a journalist want to see?"


So our users can pitch a lot smarter to a journalist or podcast. We call them the decision makers. And it also has angles that map to actual media demand.

So, I'll show you all of this and then as we're showing, I'm going to show a podcast first because podcasting is my favorite. And I'm like, I'm going to give the behind the curtain on a podcast. It's very meta of us.

Let me share my screen.


Kyle: Well, and I'll even say, I know that you used it to reach out to me and it worked. You know, the research that it did and the messaging, I was like, "Oh, wow. This seems perfect." So yeah, absolutely.


Rebecca: And the funny part is I pitched you during a workshop where I was showing it and your pitch - I mean, sorry, your contact - was just one of the matches that came up.


Kyle: Incredible.


Rebecca: Now here, and I'll show you in a moment because I do tell people, listen, it's going to say, I mean, you can choose whether or not it says, "I listened to a podcast episode," and I said, "If you get a response from the host, you, to be in integrity, you either take that out or you need to listen before you show up," right? Or you need to meet with them. Like you need to actually do the work.


However, you're not going to listen to 10 episodes before you do 10 pitches.


Kyle: Sure.


Rebecca: Which is great.

Okay. So let me share my screen.

Welcome to PitchWell.


Fun little fact. So this is not an AI wrapper. This is an actual like custom dev software code. You know, I can find my tech base or my tech stack somewhere for my developer.


But when I was designing this, I was going through Duolingo in anticipation of us moving to Italy. And so you'll notice there's a couple little things. I didn't steal anything from Duolingo, but I was like, "How do we make this like when you log in, it's like the daily?" And then you go into Duolingo, it's like, "Do three things." Every day there's three things. They do change.


And I was like, "We need three things that can be done in 10 to 15 minutes so that there is a streak." And so we have some of the same things.


Kyle: Everybody loves to get rewarded.


Rebecca: Exactly. And that's the thing is, is even looking at, and again, I ran this through the Enneagram personality test. I was like, different users will use for different reasons. Some want validation. They want to be told they did a good job. Some want to win, so we're going to introduce leaderboards. There's a credibility score. Some of them want to feel in community. So we have weekly live pitch sessions.


So I looked at like, what is the user behavior and how do we create stickiness for different personality types that are motivated by different things.


Okay. So I'm not going to go through the back end, but there is, in the settings, there's an onboarding. It takes like five to six minutes and it basically, you put in your bio, any previous media.


The second thing is under persona, you upload a writing sample, a non-AI writing sample. I mean, this goes from like one person uploading a long-form LinkedIn post all the way to, I had one client who was a doctor who uploaded her five books she's written. And what it does is it creates a persona around your voice and it's phenomenal.


And then you can add in like, "Don't use dashes. I like to use a plus instead of an 'and'." So we're going to go to pitch now.


And this is just like a little thing for me. We're actually building this into the little plus right here and "add more info," but I have redacted or distilled like what makes a good pitch, and there's like four components.


So the first one is "What do I believe?" And I prepped this early. So like one sentence on "What do I believe?" And mine is like about credibility, because we're now in a world where there's Instagram accounts with voice. There's podcasts out there that are all AI. Like we're getting to a place it's actually, you have to do a lot of extra research to make sure the person you're talking to is real.


Kyle: 100%.


Rebecca: Right. Or it could be a real human, but now every single photo and video is AI. And I mean, that looks really pretty, but like, is it landing? I don't know.

Okay. Now whatever you're saying, why does it matter right now? Okay. And so I'm saying like, PR is not optional, and we'll talk why. It's now a filter that algorithms are using to decide what's making it into publications and into LLMs.

So a little proof. Pages ranked with expert quotes, so we call this high domain authority. Publications, iTunes, Libsyn, anything that has quotes or media references are 45% more likely to be used in LLM. I'm going to put in one more stat.


Google search, which is going down and down and down. Google search converts through link clicks at approximately 1% while LLMs convert through link clicks at 11 to 17%, which is wild.


So if you have a business that you want sales for, you need to be like, "How can I get in the LLM?" And this is one of the ways.


Absolutely.


And then I'm like, "Okay, well, what advice do I have for people to do something about this and start treating earned media like product?" Like, you need to pitch it. You need to track it. Building a visibility system. So this is just a couple bullet points. I did not give it a thesis. I did not write an article or a blog.


So now I'm going to say, "Okay, let's do a podcast episode." Our data shows that our users, we're going to hit 300 users today, which we launched four months ago, and it's just like we're on a J-curve here. But our users are pitching podcasts more than every other form of media combined.


Kyle: Yeah, that makes sense.


Rebecca: Yeah. Well, it makes sense because again, we're craving that human perspective because everything else we're like, "Well, was that, I don't know, was that written by ChatGPT?"


Typically we can still tell. It's so funny. Before we moved to where we're moving, I found two podcasts about the place. It's a super little ancient city. It's the oldest city in Italy. And one of the podcasts was all ChatGPT - or not ChatGPT, it was all AI - and I'm like listening. I'm like, "This is all AI."


Kyle: And I just, it was so flat, right?


Rebecca: Yeah.


Kyle: So okay, so we got…


Rebecca: Oh, go ahead.


Kyle: Oh, I was just saying you can still tell, you know? If you have a keen eye, you can see like even like a little bit of emotion, which is weird, or something like that. Yeah, it's not perfect just yet.



Rebecca: No. And it was mostly that because they had actual voices. The voices were very flat. Like it was like a perfect cadence. It was like a metronome or whatever it's called. You're like, "Done."


So what it has now is it has a podcast pitch. Now, I've had an agency, a PR agency, over five years. We've worked with, you know, from brand new, brand new companies up to $50 million a year companies, some of the biggest names in the business, which I will not name because of NDAs, but some people that you have definitely heard of that are household names in personal development, health and wellness.


So it starts out, and I'm like, "Okay, this isn't bad."


However - and I can wait to modify until I pick someone to modify it - but I'm going to say, "Use bullet points. Make it 20% shorter."


Now, this is very similar to like an LLM and: "Make the subject line clickbait. Let's make a really great subject line so that the open rate is good."


And so it's going to take those edits. You can also edit directly into the pitch. And it is going to, and the other thing I'm going to say when I personalize is like, "Don't talk about, 'I work with women.' This needs to be for everyone."


Okay. So now: "AI-proof credibility secrets: scale your influence without losing your soul." I'm going to say, "Remove the woo-woo soul talk."


Because, you know, there's some platforms that that totally is fine, but I'm like, "Let's just be a little bit more factual here," and we'll see what it says.


Okay, "without compromising integrity." Now I'm going to save this pitch and I'm going to say, "This pitch looks really good. It's a good start."


I'm going to go down to my pitches and there's a couple of things I can do here with this. One is I could say, "I want to talk about this more," which obviously I do want to talk about this more. And I can personalize this or repurpose it, recycle it into any other form.


So I can do a TV pitch, which is a different format. I can do it into a publication. I can do it into a magazine, a newsletter, almost whatever I want.


Right now, what I'm going to actually do right now, just for the sake of time, I am going to personalize it. And there were tags earlier, and I'm going to say "AI, business growth." I want to see what comes up because I usually use like "business AI marketing" or "business AI visibility."


Okay, so it's got all kinds of podcasts here. "10X AI for business growth." This is being pulled directly from Libsyn and iTunes, but then it's vectorized, which means it's not just pulling from that feed. It's also pulling the website of the host. It's pulling their social media.


The first thing I'm going to do is say, "Is this podcast actually live?" So this one is six months old. It's not dead yet, but it's considered inactive. Once something's over a year, it goes dead in our database.


Kyle: Okay.


Rebecca: Let's look at "Elevate AI: business and personal growth," see if that's a better fit.


Okay. Nope. One episode. They were in the death trap of, they didn't get past their first eight.


Okay. Let's try this one.


Okay. Let's see. AI Growth Insiders.


All right. Again, let's just go with this one. I know it's also inactive. One of the things, actually one of the updates that we're pushing right now is actually this one is even better, is we're doing an update to remove all the dead podcasts if they've been over a year.


Oh, so one thing is if there's no email address, it won't come up.


Kyle: Okay. All right. I think what we're learning here is that The Brainiac Blueprint is the only AI podcast out there and everybody should be subscribing to us.


Rebecca: That is 100% right.


Well, you know, and that's another thing is I could have just searched free. It won't let me actually re-pitch you because we, I pitched you in the last 30 days. So I was, I can't, I could use you as an example, but it wouldn't do what I need it to do.

So it's going to look at this podcast. I'm now saying personalize. And what's amazing is it just went through all of the information and it personalized it not only to that podcast host, but literally to their episode.


Now, if this was a publication pitch, it does the same thing with the journalist, but it's a previous article. If it's a TV pitch to a producer, it's going to be a recent segment, right?


So I can go through and again, I'm going to say, "Make bullet points, shorten, and make the subject more powerful."


Okay. So I'm going to do that and then I like to add in a personal touch. So I'm going to say, "I listened to it while walking my dog," because that is actually when I usually listen, or, "while doing laundry and dishes at 10 o'clock at night when my family's asleep."


Kyle: There you go.


Rebecca: So, you know, that human element is really important because I know you probably get so many crappy AI pitches also.


Kyle: Well, you know, I think, you know, to your point about AI being, you know, taking over in a lot of ways and people looking for the human touch, relatability still is so important. To be able to say, "Oh, yeah, yeah, I listen while walking my dog too." And it's such a simple thing that I think gets overlooked with, you know, the return, if you will, from the effort of adding that in.


Rebecca: I mean, I would say the human touch is more powerful than ever. I got a voice memo today from a woman that she has a, she's having an event with 500 people, and she's like, "We'd love you to be there." And it was actually a pitch because she wants me to, she wants us to be a sponsor, which we're like, "Hey, PitchWell, this is the ideal audience. Let's like look at making this happen."

But she left me a voice memo, like a minute and a half. And, you know, that's not an assistant.


Kyle: Yeah.


Rebecca: Right? You know it's the person.


And so I actually think that because so many people are taking like the shortcut with AI that it makes it even more powerful now when we actually use our, literally use our voice for good, right?


Okay. So now that pitch is personalized. It's in my personalized folder, which you can look at things as a card or a list.


And so now I can go in and see, you can see the woman's email address. I can hit send. Now you can send it to yourself to preview. I'm going to go right to the review pitch.


Here's the really cool thing, though. I'm going to remove her last name. We use a Google integration. So it's going to pitch actually from my inbox, but it sends a pixel out that the person receiving can't see, which calls from our database. So we know when the person saw it.


You can schedule send it if it's not a good time. If it's middle of the night or on the weekend, like don't bother people, schedule send it. Don't pitch journalists Friday through Monday morning.


And now it's sent and it is in my nurture. And then we have a basic nurture. The nurture also utilizes Winsley or proprietary AI.


Can I show one more really cool thing that I didn't show you in our demo?


Kyle: Please. I'm enjoying this. I think everybody else will be too.


Rebecca: Yeah. Okay. So this is so funny. Our developer did this update and I hadn't tested it before I was doing a live workshop. Probably pretty foolish to actually demo a new feature without testing it before I put it in front of people.


Kyle: Shows a little vulnerability. It's all right.


Rebecca: I mean, I like to show behind the curtain. I'm like, you know, I want to take you along for the ride. I tell people, "We are in beta. Thank you. You know, excuse our dust and thank you for your patience."


But this is Winsley. So obviously Winsley powers all of the generation, the searches. We actually, I think, use five different versions of LLMs because different LLMs have different strengths right now.


But I go in here and I say, "Can you give me three prompts to turn my podcast pitch into a viral LinkedIn post?"


So you can actually ask Winsley to give you great prompt generation because as we know, our result is only going to be as good as our prompt generation typically.


Oh, I like this. Okay, let's do a value-driven listicle. So I'm going to grab this. I'm going to go back to my pitches, and it's going to be - oh, actually, I should personalize. So here it is.


I can go to recycle. I'm going to go up here to other platforms, social media. I'm going to just literally copy and paste from Winsley to Winsley the prompt.

And one of our features that might be out by the time your podcast is out is actually just having some recommendations for some of the top prompts.

And now, by the way, this can be turned into a carousel for Instagram. So now it's turned that pitch into social media content.


And why this part is so important is, I understand and I'm very honest about the fact that everyone knows they need visibility, PR, authority, but it's going to go to the bottom of the list with all the other things founders do.


And we're founders. We're not content creators. And even marketers, right? Like, if you're a business owner, you have a product or service, you know you need to create content, but it still is typically the thing that takes the longest and is last on our list.


So the reason we put content recycling in here is two, well, three reasons. One is to give people a tool where they're now only in one thing that already understands their voice, but is to create content that is authority content that then you turn into social.


Because right now people are like, "What do I post about today? What did I just talk about?" If you really think about, "What is the thing I can talk about that I can show up as that credible expert and then how do I turn the thing I just pitched into my post?" It's so powerful. And it obviously, for us, it makes the platform more sticky too.


Kyle: That was so cool. I love all the stuff that you have built in there. I think there's a lot of great use cases. I think everybody can kind of see how it fits into their own business.


I'm curious. I think to your point, it can be something that gets deprioritized or even could just be overwhelming. You know, don't know where to start.

So I'm curious if somebody is starting their, we'll call it visibility journey, what is that first step for you in your mind? Obviously you could say, you know, go to PitchWell, of course, but, you know, if, you know, how do they start? What does that first step look like, you think?


Rebecca: Well, so regardless of PitchWell, when someone would ask me, "Hey, I want to build my credibility," or, "I want to differentiate myself," I mean, coaches want to differentiate themselves, "I want to be able to charge higher rates," right? Authors want to sell books. Like everybody has a reason that they want to be more credible, more visible.


Credibility differentiates you. It increases your possibility if - especially in service space. It gets someone to pick your product or service over the other person. But the other thing is it shortens the buying cycle significantly, which everyone's interested in.


The visibility is new eyes on you. And so I always tell people, you know, you can kind of go two directions. You can go credibility and you can go visibility. They're not always the same.


So yes, pitch media, get a couple quotes because that will be credibility when you've got the logo. I also tell people a logo does not mean it's going to bring you leads, followers, list growth. It can, but that's a bonus. But having, "Hey, I was featured on this," or, "I was featured on that," subconsciously it does matter to most people.


And so it is a signal that usually opens doors. But I personally love podcast guesting, not just for me, but for most people because even people that are a little bit afraid of public speaking, you're not on a stage, you're having a conversation. And if you're passionate about what you do and you've got case studies or testimonials or client examples, right, like most people can show up if they understand where to add value.


And the thing that most people don't know, and I've seen this by one, being a podcast host, but also I have community, I have events, is looking at podcasting as a visibility flywheel. It's like the modern addition, and it's proof of thought leadership. It's proof of depth, proof of clarity.


We're not even going to talk about the fact you can repurpose video. You can repurpose it into video clips, into long-form content, into blogs, into, I mean, email lead magnets, like 30 pieces of content per episode.


Kyle: Exactly. Exactly. I mean, and if you're good with repurposing. But what we're seeing, especially inside the PitchWell community, is like one good episode is a cascade of opportunity. And so I like to - I call it reverse prospecting the podcast host.


If people want to get on stages, I'm like, "Don't go apply for stages. That's actually really hard." Find a stage where the host has a podcast because guess what else? They usually have a mastermind and some type of other smaller event. They usually have maybe a group coaching program or a Facebook group.


Pitch their podcast because that is an audition for those other opportunities.

And I have literally seen founders that I've worked with on their visibility, they started with a podcast that landed them an opportunity to speak to a group that landed them on a stage. I had two different founders who got $200,000 raised from events where they did not pitch that they were fundraising.


They talked about their vision. They talked about their mission. They talked about the transformation. People tried whatever it was. One of these was an app. One of these was a physical product, and they had $200,000 raised from people in that room.


Kyle: That's awesome. That's so cool.

And it started on a podcast.


Rebecca: Yeah, that's so cool. And I couldn't agree more. I feel like a podcast is the perfect way to start, you know, building your voice, you know, sharpening that skill set. You know, I myself, I'm not necessarily afraid of public speaking, but I can even say just from beginning the podcast to now, like my speaking skills and question and listening, it has all improved and stuff like that. So just, the confidence, you know, just gets more and more, or gets better and better the more you do it.


Rebecca: And you don't always know where the conversation will go or if you're okay with that uncertainty, right? It can turn into, you're like, "Oh, wow, we went in a place that I hadn't gone before," and either the audience reflected back that this was super interesting or the host did.


And that can give you new content directions or new angles.


Kyle: 100%. I have totally agree. I've gone in a lot of different directions, you know, through some of these conversations and honestly just learned a lot and it's been fun. It's been great to have these, again, the human connection and everything.


Rebecca: And email list growth. Like most podcasters promote their episodes. And if they really love what they're interviewing someone on, you know, that can be turned into an affiliate or a partnership opportunity. I mean, there's, again, sky is the limit with podcasting.


Kyle: I agree. I agree.

All right, so last question I want to ask in terms of this big, you know, the core section of the podcast here.


You, again, you have a lot of experience in a lot of different components. You wear a lot of hats. I'm curious as to what advice you would give somebody who wants to make the leap into entrepreneurship. Again, I know you've kind of, you know, gone from journalism to PR to AI and you've made a lot of changes and adjusted.

So, you know, what piece of advice would you give someone looking to make that change, make that leap?


Rebecca: I think the first thing is just putting out valuable content, which I know might sound counterintuitive. Someone's like, "Oh, I need to build something and then I'm going to go market it."


But I know for me and so many of the people that I have worked with is when they were still in corporate, before they had built something, they just started putting out value related to their area of expertise and people started to listen as people started to watch. And it actually, what you're doing is you're nurturing your audience before you ask them for anything.


And the other is, is you're building the muscle of learning how to be in front of a camera or market yourself or just put yourself out there, which, I mean, that does require some vulnerability before you have to do it because you need to pay payroll or you have milestones that you have to hit.


So that would honestly be the first thing. And I think the other is be good being a beginner again, being curious.


Kyle: Yeah.


Rebecca: Yeah, because even for me as someone who's coached hundreds and hundreds of people one-on-one, thousands in group programs doing this, I know PR really well. I know business really well. You know, I have an agency, but I've never been a tech founder of an AI platform.


So it's that balance of, like, I am constantly asking for advice, for feedback. I'm watching things or reading things, and I can't ever think like, it's like that balance of "I know what I know and I also don't know what I don't know," and having humility and not a lot of ego around whatever it is that you do.


And I don't know if you've heard of Tim Draper. He's one of the biggest VCs like in the world.


Kyle: I think so. If anybody Googles him.


Rebecca: So Tim has, I mean, he founded, or not founded, but he invested in Bitcoin and, well, Theranos, and so, you know, some really big hits. I mean, probably one of the most successful.


His daughter, Jesse, who's also, she's like a fourth-generation VC, all-female fund, or should I say all-female founded companies. And I had her speak at one of my events and she was like, "The best founders are the most humble, hungry, curious. They don't come in with ego."


She's like, usually the loudest, most egoic are the ones that are like, I'm going to paraphrase this because she didn't exactly say this, but the gist was, you know, be really careful about the ones that are like, "This is exactly what I'm doing. I know my stuff," right? Like, yes, it is a balance. You want to have a confidence because you're obviously taking risk and you're putting yourself out there and saying, "I have something of value," but you also need to be constantly learning, constantly learning and adapting.


Kyle: Yeah, I agree. And, you know, I think along those lines, the action is always going to be better than inaction, right? So like, if you're going to go and learn something or even just go and do something and do it wrong, that's going to be better than not doing anything.


Rebecca: You learn through action.


Kyle: Exactly.


Rebecca: Action gives you information. And, by the way, there's no such thing as failure. It's like when you take action, you don't fail. You get feedback. And you're not operating in a vacuum, in an echo chamber of your own ideas, fears, and patterns.


Kyle: Progress over perfection. That is my mantra. I love it.


Rebecca: Exactly.


Kyle: All right. All right. Cool. This is awesome.

So let's jump into the rapid fire section. Got five quick questions for you.

I love the world of automation, hence LeftBrain here. So I always ask this one just to kind of see where their head goes. If you could just click your heels and all of a sudden you have this beautiful, fully built-out automation either in your business or in your life, what would it be?


Rebecca: Oh my gosh, for my life it would be related to every single domestic task.


Kyle: Of course.


Rebecca: Laundry, dishes, lunch packing, all the stuff that my kids are like, "Why are you bossing me around?" I'm like, "I'm not. I'm just trying to get you ready." That would be it.

For business… Okay, this is an oversimplification, but anything that doesn't use my brain, my creativity, or my voice, I would love to just automate out.


Kyle: Absolutely. The repetitive tasks.


Rebecca: Exactly. And I am, you know, I mean, thanks to AI, a lot of those are getting automated out, but I mean, I can't wait to see where it's going to go two years from now because I think that, again, it's going to take away the things that aren't creative for us. And so we will have more time, which is what we want.


Kyle: Exactly. That's the goal, right?

All right, question two. What is something you plan on doing more of in 2026?


Rebecca: Sleep.


Kyle: I like that.


Rebecca: No. 2026, actually, discernment. I haven't picked my word of the year, but discernment. I think that we're all going into that. It is being really aware of like, I don't need to fill all the space. Like I actually need to leave things open.

And the other is, is because I have for the last few years been in a business where everything is referral-based. Like we don't market our agency. Everything's been referral-based. Most of my coaching has been all referral-based or coming in from live events. And moving to a SaaS model, I have in the last month gotten really good at doing reach-outs. And right now they're still warm, but there's going to be a point where they're not, right? They're cold.


And asking, "Hey, who do you know that has a community or a podcast that I can get in front of, that we can serve their audience?" And so I think all of us need to do that, is reaching out to your network. However, you need to serve the network before you reach out to ask for something.


Kyle: Absolutely. Build that value, right?


Very cool.

Question number three. What was the biggest culture shock upon moving to Italy?




Rebecca: Italians are not interested in making money. And it is… I know that sounds really basic. And I'm not saying they're not interested. Obviously, everyone needs money to survive. But it is such a, you know, I come from, I've spent the last 12 years not only in California but in Silicon Valley. Everything is like bottom line, innovation, fast, optimization, productivity.


And here, some of it's beautiful. You're like, "Oh, it's lovely to go in a cafe and not be rushed." But there's times I'm like, "I just need the bill," and it's 20 minutes to get the bill.


Or I have a tutor, and I'm like, I asked her, I was like, "Wait, is my…" Because my husband and I both take classes from the same tutor but at different times. And I'm like, "Has he paid you?" We haven't paid her for six weeks. And she just kept tutoring us. And now I'm like paying her for the week ahead because I'm like, "Let's never be in that situation," but she never asked.


And so it's just like actually asking is so, it's so bizarre. And then also that nothing makes sense. Everybody says no to everything up front. Anything bureaucratic or like, "Can we do something?" And then you just continue to have a conversation and eventually they can figure it out.



But there's definitely a very big difference with just the everything-is-possible attitude that I think we have in the US as entrepreneurs. Interesting. That does not exist here.


Kyle: I've heard a lot about the, what is it, work-to-live mentality as opposed to live-to-work that we have. That's interesting to hear about that there.

All right, cool. Question number four. We're going to stick with Italy here. The Olympics is coming up. If you were to be an Olympian, what sport would it be in?


Rebecca: This is so funny because literally the Olympic flame went by our house last night.


Kyle: Oh, really? That's awesome.


Rebecca: I saw the Olympic flame parade twice. I haven't actually seen the flame. I saw the thing it's in.


If I was an Olympic sport, which one would I do? You said… Yeah, exactly, if you were an Olympian.


Okay. Oh my gosh. I've always loved the ice skating. Summer would be gymnastics. The ice skating is just amazing.


Kyle: Nice. Love that. Awesome.

Cool. Question number five. What is the best holiday present you have ever received?


Rebecca: That is… That's a tough one. My husband and I typically don't do presents. We do experiences.


Kyle: No, I mean, that's the best way to do it, honestly.


Rebecca: Yeah. So I'm trying to think of a specific one. Well, this year we're going to Taormina for three days and we're just going to do Christmas in Taormina.

I think a camera, though. I've always been really into photography. Obviously now everything's on my iPhone, but when I got a camera for Christmas.


Kyle: Very cool. Love that. Taormina sounds awesome though, too.


Rebecca: I'm pretty excited. If you've seen The White Lotus, you know, hopefully there will not be any dead bodies while we're there.


Kyle: Fingers crossed. Yeah.

All right. Awesome.


We have reached the open forum section. Is there anything that you're just passionate about, maybe we didn't get to talk about, that you want to share with everybody?


Rebecca: Giving back. And I think this is such an important thing.

Actually, in PitchWell we built it in because when I looked at building a platform, I was like, I've always included scholarships in my group programs and, you know, like equity-based, and I was trying to figure out, "How do we include that for a SaaS product?"


So we have something called Pitch for Good. We are launching it this month, so probably by the time the podcast is out.


And so for anybody that is a veteran or active-duty military that obviously, I mean, ideally they have a business or a product, or for anyone that has a 501(c)(3), you can email me rebecca@gopitchwell.com. We'll soon on the website have an actual form. And you get free access for life to PitchWell because we want to democratize visibility for voices that have not traditionally been heard.


And so the other is, go ask your ChatGPT, your Claude, your Gemini, "Hey, how do I give back this holiday?" Whether it's with your time, your energy, your resources. Go ask for something creative.


What I'm doing right now, just on a small scale, is we have a homeless guy that lives on the flat steps next to us, and I give him food every day. So that's just like a little thing, but it also is very human because I also just say hi to him like, "Hi, Rocco," and treat him as a human being because a lot of people don't.


And then for our kids' school, we're donating, it's a very poor public school in Italy, which is a great experience for our kids. We're donating their school supplies for the rest of the year and a printer, and we're paying for an English teacher to come in because right now they're being taught English by non-English speakers. And I'm not talking native English speakers. I'm talking they're learning English out of a textbook by someone that doesn't speak any English.


And, you know, obviously there's a lot of opportunities. I'm not trying to be in, you know, savior mode for this town, but it's like, "Where can I contribute because honestly it takes so little?"


And so I think everyone can do that. Everyone has the ability to give of their time, their energy, their resources, something that is going to move the needle.

And I think in business, if every business owner consciously gave one resource away every month, like really, not just like, "Oh, here's my lead magnet," but like really introduction or something, it would completely change the face of business for good.


Kyle: That is a beautiful sentiment. I'm feeling very inspired at the end here. I'm so glad you brought that up. I meant to jump into that earlier, but we just went through a lot of different stuff. So thank you for bringing that up. That's so cool to hear that you guys are doing that.


So, Rebecca, thank you so much for joining. This is great. Again, your passion comes through with every word that you say.


So, if people want to check you out, they can reach out on LinkedIn, Rebecca Cafiero. I know you have your website as well as gopitchwell.com.

Any other sites or social medias or anything like that you want to plug?


Rebecca: I mean, I'm on Instagram, @rebeccacafiero. There's definitely some founder stuff on it. There's also just a lot of Italy right now.


So if you want to hear more of my point of view of what it is like to move away from Silicon Valley while building an AI startup into a town that is the oldest place in Italy and barely has internet - thank you, Starlink - then yeah, follow me on social.


But if you just want PitchWell stuff, go to gopitchwell.com and try a trial out of PitchWell.


Kyle: That sounds like an upcoming Netflix documentary or something right there.


Rebecca: I still - you know, I did not purposely plan it.


Kyle: No, no. Actually, you know, just to close out, we knew we were doing the sabbatical and I was closing down or automating or delegating all parts of my business so that I could really be present. And we were supposed to be going January 2026. And my husband finished at his job after his, you know, four years after selling in August.


And I said, "If we don't go soon," I could already see the writing on the wall. He was like, there were conversations, people are starting to make offers for his next startup, which he hasn't even figured out yet. And I said, "If we don't go now, he's going to go back to, he's going to end up building something."


And I started building PitchWell. And we were getting such momentum that I was like, "If we wait six months, I'm going to be in so much momentum that to leave is going to be so discombobulating, it's going to kill our growth." So I said, "But if I build out the beta from there when I need to be in a cave anyway instead of when I need to be so visible, ironically, then that can work."


And there was also a piece of me that said, "Building a startup is so hard."


Kyle: It is. Absolutely.


Rebecca: But man, moving to a new place where you don't speak the language and navigating having your children in school where the first month they like cry or every day say they don't want to go and building that resilience, like, and navigating bureaucracy and paperwork and language, I was like, "That's actually harder than building the startup."

I believe.


So it exercised my grit muscle, and now I don't want to say it's easy, but now it's all doable. It's all figure-out-able.


Kyle: Absolutely. When you can survive that kind of real-life type of stuff, everything else just is, all right, just something on the to-do list to check off.


Rebecca: Exactly.


Kyle: Awesome. Well, this has been great. Thank you so much for joining me on The Brainiac Blueprint.

If you don't mind, please look at the camera and say, "Stay brilliant, Brainiacs."


Rebecca: Stay brilliant, Brainiacs.


Kyle: Awesome. Thank you so much.


 
 
 

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