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Ray Gutierrez
You're mixing your heritage, your past and a little bit of pain into your mission. Let's talk about your why. What is your why?
Shayla Paz
It's always comes to my family. It's always like you are broken into so many pieces when you are torn apart from your family and then you're trying to figure out how to get back together.
Narrator
Shayla Paz is a Cuban American entrepreneur, travel expert and the founder of Shayla Adventure Travel. Through her work as an award winning film producer and ast a verified travel advisor, she creates transformative journeys that connect people with cultures around the world.
Shayla Paz
Life in general is an adventure. You're doing one thing today, tomorrow you're going in a discovery mode or something else. And my whole life has been one adventure after the other one.
Ray Gutierrez
What are we going to learn from your episode?
Shayla Paz
Resilience sometimes is a tool that you can use to move forward and not giving up too soon. Don't give up before you know you reach a goal. Stay persistent, stay focused, create a vision board. Don't just think about your goals, just write it down and write down the steps that you're going to pursue to accomplish your goal.
Podcast Intro Voice
It spans the globe like a super high cold Internet. Elvis Preston. Today, Apple is going to reinvent Lefontein. It's not over until I win the living your legacy podcast for those who live to leave a legacy that's extraordinary. The impossible. Oh, that is sensational. Open Chicago with the lead. You can live your dream.
Ray Gutierrez
Welcome back to another amazing episode of the legacy makers podcast for inside Success. I'm your host, Ray Gutierrez. Joining me today is quite an adventurous soul that also enjoys the color red and is dear to my heart because we're both very much Cuban. Shayla.
Shayla Paz
Boss.
Ray Gutierrez
How are you, my love?
Shayla Paz
I am doing wonderful, Ray. It's such a pleasure to meet another fellow Cuban.
Ray Gutierrez
Oh, well, we hear it's two, two, two Cuban ships kind of crossing through the night going, hello. So welcome, welcome. You are in the chair, the nice green chair, which I'm going to brand now, the legacy maker chair. We literally finished your interview. We finished filming your episode. How do you feel?
Shayla Paz
I feel amazing. I think it was wonderful. I have some tears, a little tears, but a lot of happy moments. It's always like, amazing to share my story with other people and tell them where I come from and what I stand, what I stand for. And it's always an adventure.
Ray Gutierrez
Right on. Let's talk about where your adventure begins. You're mixing your heritage, your past and a little bit of pain into your Mission. Let's talk about your why. What is your why?
Shayla Paz
It always comes to my family. It's always like you are broken into so many pieces when you are torn apart from your family, and then you're trying to figure out how to get back together. And we're still not together. I mean, they are in Cuba. I got family in Italy. I got family in Canada. I'm here. So we are spread. And I'm always trying to figure out how to bring us together. And that's always like their mission impossible, you know?
Ray Gutierrez
Right on. Let's talk about your artistry and how you've merged your culture into the. Into your adventures. First of all, why adventures? Adventure of. I was corrected. There is no answer to adventure. It's just La Ventura, your adventure. Talk about the name and the philosophies.
Shayla Paz
Because life in general is an adventure. You're doing one thing today. Tomorrow you're going in a discovery mode or something else. And my whole life has been one adventure after the other one. From being a kid, from being from one house to the other one. Every week, every day was different. And the first time, I remember, the first time I got on a plane was because I had to go to Havana to have a knee surgery. And that in itself was an adventure because I'd never been on a plane before.
Ray Gutierrez
Oh, wow.
Shayla Paz
And I was traveling by myself with a knee injury. I didn't know anybody in Havana. And a stranger on the plane, Cuban, helped me. And I was like, oh, my God, I hope that he doesn't do something to me. You know, My mind was going through the worst, of course. But he was so nice to me. He took me to his house, and the next day, he helped me find a distant cousin's house so I could stay there.
Ray Gutierrez
Yeah.
Shayla Paz
And the distant cousin treat me like she know me for life, you know? And that's the essence of Cuban people. You know, he's like, oh, welcome. This is your house. It's, you know, whatever. And that in itself was the beginning of my adventure because that led to other moving around and traveling.
Ray Gutierrez
The moving around and traveling is what I want to focus on. Because this is how you developed your traveling agency. But you're beyond a traveling agency. I forgot what the terminology we used. It was essentially a wealthy adventure or a wealthy spiritual. A wealthy guide for immersive adventure. Something like that. Remember we said it towards the end.
Shayla Paz
It's a discovery trip. Where you go to immerse yourself in other people's culture is a true adventure.
Ray Gutierrez
Correct. You go beyond just Getting off a cruise ship and going through the touristy, you know, exit through the gift shop. No, you're really immersed in exploring what makes the island or that world tick. Talk about how you developed this adventure from. From onboarding? Actually, no. From the clicking on the ad to getting to meet you to getting on the ship. Because you said it yourself, you're planning three trips.
Shayla Paz
Yes, right now I'm planning, as in three trips.
Ray Gutierrez
The trip you get to before the actual vacation and right after it.
Shayla Paz
That's right. Oh, your philosophy. Okay, so when you going to travel, you experience the destination three times. Correct, that's what I meant. Before you travel. Because you're talking to me about what is it that you want to do, what is your dream, what is it that you want to accomplish on that trip and why you're going on that trip. And so I want to learn from you so I can match you with the right destination or the product that you are to accomplish your dream. Then when you are on the trip, then you are dreaming you're already going through that destination. The dreaming stations become a reality. So you're living your dream. And then when you come back, every time you look at your memories and you talk about that trip and everything, you're reliving that dream that you accomplished. So. So you travel three times.
Ray Gutierrez
That's amazing.
Shayla Paz
Yeah.
Ray Gutierrez
Do you see the transformation, the before and after?
Shayla Paz
Yes.
Ray Gutierrez
What are your clients? Are there folks that are lost, that are looking for a new adventure purpose? Some folks like to go to retreats and do ayahuasca. Some folks like to go to Antarctica. You're a little more tropical. And what do your clients look for when they come specifically to you?
Shayla Paz
Sometimes it's just like they have like a bucket list item, you know, Oh, I always wanted to be there. Oh, that's a dream mine. I said, well, let's talk about why it's a dream of your. Why did you wanted to go there? What is it that attracted you to that destination? That's what I want to know. When they talk to me about their trip for Cuba specifically, people was like, oh, I always wanted to be there. It's like the forbidden apple, you know? So, sure, okay. And they said, well, it's a shame that you cannot go there and say, why not? You can go. People think that Cuba is cloaked.
Ray Gutierrez
I still don't think I can go. And I live in Miami and I'm Cuban. I'm like,
Shayla Paz
absolutely, you can. It's so easy. I take care of everything. So you don't have to.
Ray Gutierrez
Yeah, but the way you say that sounds a little sketchy. I'm just joking because people go to Cuba. They go, well, you gotta leave Miami, go to Mexico. And then from Mexico, aha. Teach me your ways.
Shayla Paz
You can fly from Miami, you can fly from Tampa, you can fly from New York, you can fly from Atlanta.
Ray Gutierrez
Oh yeah, what's the airline?
Shayla Paz
Delta? No, American Airlines.
Ray Gutierrez
No way.
Shayla Paz
Yes.
Ray Gutierrez
The American Airlines just lands in Cuba. Like no big deal these days.
Shayla Paz
Yes, yes.
Ray Gutierrez
That's news to me, bro.
Shayla Paz
That's what I'm here to tell you. Yes. Thank you.
Ray Gutierrez
It's already working. I'm here. And this was for free?
Shayla Paz
Yes. You go to Cuba under a specific license, general license. The one that I work under is the support for the Cuban people. So you have to have a full itinerary and you have to certify that you're going under that certification. And I create that document. I already have that taken care of. All you have to do is sign it. I take care of your visa, your itinerary. What are you going to do every day? Who are you going to meet with? Your tour guide, your transportation, your meals, everything. I, I plan everything by the hour, pretty much.
Ray Gutierrez
That's amazing. That's so important because I don't go on vacation because I hate the planning for the vacation. By the time I'm done with it, I'm like, I'm not going to do half these things because I just want to just be still and be at peace. Someone else should do this for me. I need to find myself in these adventures. So it's amazing that I'm going to a place like Cuba, but with purpose. Not just as they say. You can curse on this podcast.
Shayla Paz
Always tell people that. Don't go on this on a trip with expectations. Yeah, okay, you need to lower your expectations because a lot of countries don't have all the sophistication and all the tools and all the technology and all that, that fancy stuff that people in the United States are used to. So when you go to a Latin country, they got going to a chalk and they expect to have like a five star service. Well, if you're booking a luxury travel, a luxury hotel, of course you're expecting that. But if you're going to immerse yourself in the culture, don't be expecting like a five star service. When you're trying to help the people,
Ray Gutierrez
how do you, how do you, how do you meet expectations Then like I say, lower the expectations. But how do you meet folks expectations? What are people expecting when they go to Cuba, like trees, like besides trees. But what are they expecting when they get there and what happens when they don't get that? How do you deal with that?
Shayla Paz
I always tell them to go open minded because once they come back they are like, wow, it's like an eye opening experience because they go with this scene in their mind of what they read on the papers or seen in the media and we get there is a different reality.
Ray Gutierrez
Yeah.
Shayla Paz
And I always tell them, bring enough money so you can, you know, buy souvenirs from the locals, give some money to people that you may want to give to for tip and you don't have to over tip if you don't want to, but you know, they will appreciate it.
Ray Gutierrez
Now you can be, you can be honest here. Well, I hope as always honest as, as honest as you need. Are you, are you able to bring tourists into the, the more high end areas of Cuba? Are you still going through the real progresa like, like the small towns that are suffering? Where do you navigate this vulnerability where it's beautiful sights and sounds versus suffering?
Shayla Paz
I always take people through the heart of Havana where they can see the beautiful old buildings that are still standing or some. You can see a beautiful restored building and you can see one that is falling. So they can see the contrast. Right. You can see that in all Havana. And then I take them to a place that is called Muraliando, that is a community art place where people go there to learn about the locals and they can get hands on workshop. Like they can make a plaque, they can make painting. You know, they have a hands on experience with the locals and then they have artists there that have their own art and they can buy from the locals. They can learn how to dance with the local and they can dine right there. They can have lunch with the locals so they can have that local experience. Immersion. That's what I'm talking about, you know, being with the local, getting off the beaten path. So they saw, oh, Havana, where he's being mixed up and you know, this is history here.
Ray Gutierrez
Sure.
Shayla Paz
And then you go off into the neighborhood and then you see, you know, like contrast. Right, Contrast. And then I take them to Vinales, which is two hours from Havana by car.
Ray Gutierrez
Wow.
Shayla Paz
And it's not a pretty road. You're gonna be like a bumpy road. And they're gonna be in a taxi on a car or something and it's gonna be hot. It's not gonna be pretty.
Ray Gutierrez
Oh yeah.
Shayla Paz
But I want them to see that. I want them to experience what a thrill Cuba is like. I wanted to see them people standing on the side of the road high shiking and trying to get a ride.
Ray Gutierrez
Sure.
Shayla Paz
And you wouldn't see that here or you see it sometimes and, but that's how you, you move around Cuba just asking people to give you a ride. And then they get to Vinales and they were like wow.
Ray Gutierrez
Yeah, the wizard of Oz. You follow the yellow brick road and you finally get to the big, big green palace. My question to you is, let's see me go through my nose. Security, when you, how do you keep your, your, your, your clients secure? Is there, is there security checkpoints? Do you already know that these zones are less violent? Because I brought that question up on, on the po on, on the inner interview. But I want to make sure we brought up in the podcast because a lot of folks don't like to venture off from comfort because of security of the unknown.
Shayla Paz
Yeah, well it depends on the destination. Cuba is a very secure place. There is no violence, there is no guns and people are very welcoming. It's always safe to go to the state website. I don't have the name from the top of my mind but I always put it on my clients itinerary to go on there and open a profile and submit their travel dates and what country they're going to. So they get alerts if there is unrest on that destination. So they stay within the area that are safe. Obviously if I'm working with a tour operator in another destination, the tour operator have an 800 number that they can call if there is any emergency and they are there on my behalf taking care of my clients. And I'll always have transportation provided for my clients so they always have to stay within the perimeters to stay safe.
Ray Gutierrez
How now let's talk a little bit of business. How do you ascend a client? You know when you get off a cruise ship they're already asking you to book the next cruise ship and then they're, they're asking you to book the photo and book the dinner, the dinner with the group and the cocktail. And how do you keep the clients part of your ecosystem system and go did you like Cuba? Well let me show you Puerto Rico and if you like Puerto Rico, there's a two for one selling Costa Rica. How do you keep the client in your flow?
Shayla Paz
Follow up, follow up, follow up, follow up, follow up. So every time the client travel I always send an email while they are in destination. Just checking in, just checking in, make sure everything is okay. Are you Having a good time, whatever. And they always respond, oh, we're having an amazing time. Or if there is a little complaint or something, I have to take care of that. And then they, when they come back, I send them three days later a welcome email. I want to know how the trip went and where do they want to go next and, and that's how I keep them engaged.
Ray Gutierrez
When you, when you are on site, do you have videographers, content creators, is that, is that something you supply or is a very intimate, quiet.
Shayla Paz
It's very intimate. I, I try to take pictures myself when I travel with clients or if they're not with me, I try to get the tour guide to send me pictures.
Ray Gutierrez
Gotcha.
Shayla Paz
So I can have that as a testimonial and share in social media. My clients having a great time in X destination or when they come back, I ask them on their review to send me a couple of pictures so I can share it.
Ray Gutierrez
Yeah, do. How, how are important are Google reviews? How important is the feedback from a client?
Shayla Paz
That is the number one source that I get. A lot of people come in because they can go in there and post a five star review of what my agency did for them. And also as a NAFTA verified travel advisor, there is a website that they can go, it's called Very Very Vacation that they can go and read the reviews from my clients that I have posted there. As a verified travel advisor, it's very important that people know that I've been vetted by one of the most trusted agencies in the world. Yes, very cool. And that I've been certified and that I took the time to learn and gain knowledge about the industry and that I'm always going to be there for them.
Ray Gutierrez
That's amazing. Let's talk about what we accomplished today. What are we going to learn from your episode?
Shayla Paz
They're going to learn that resilience sometimes is a tool that you can use to move forward and not giving up too soon. Don't give up before you know you reach a goal. Stay persistent, stay focused. Create a vision board. Write down your goals. Don't just think about your goals, just write it down. And write down the steps that you're going to pursue to accomplish your goal.
Ray Gutierrez
So let's say people are watching or listening to this podcast. What should they prepare before they come speak to you? You mentioned a vision board. A vision board is very important to you, right? Explain that. And why is that so important to your onboarding process?
Shayla Paz
Because when you do a vision board, you're visualizing what you want to accomplish.
Ray Gutierrez
Manifesting.
Shayla Paz
Yeah, yeah, manifesting. And we talk about my little green book. I have a law of attraction book that I write down my goals and I write it down by day, by week, by month, or by three months. I'd have my five year goals also. But to get to the five years, I must start at step one. You don't start running before you start walking or crawling. Right. So I always see my vision. I have it on my wall in my office. So I see it constantly.
Ray Gutierrez
Constantly.
Shayla Paz
As a reminder.
Ray Gutierrez
That's the goal. The North Star.
Shayla Paz
Yeah. That's your guidance. That's what you need to follow. So it is very important to have that taken care of so you can stay on path.
Ray Gutierrez
So folks that are scrolling through our app and they land on your thumbnail and they say, oh, a travel agent. I want to become like her. Where do I start?
Shayla Paz
You have to start by going to travel school.
Ray Gutierrez
There's a school for traveling?
Shayla Paz
Yes, there is.
Ray Gutierrez
I think it's called. I think it's called geography, ma'. Am.
Shayla Paz
Yeah, no, it's not geography. It involves geography. You must know geography. But I actually didn't start by going to travel school. I started because my passion of Cuba and giving back and because I had the knowledge of business from a previous business. I was like, oh, I know how to launch a business. I'm just going to start creating these packages and, you know, put a price on it. And I'm just going to go and talk to people about going to Cuba. That's what I did. And then when I went to become a member of the American Society of Travel Advisor, and I heard everything and saw everything and everybody talking. Oh, my God, I can be in trouble because there are so many laws.
Ray Gutierrez
Sure.
Shayla Paz
You know, they're always constantly changing the laws and regulation for travel. And you have a big responsibility when you're booking people on a flight or you booking people on a trip, on a cruise or, you know, you are liable. So I didn't know that I could be liable. I was just like, you know, you're gonna take people who kill us. So I just went on and did it. So having learned that, I went on and immediately got into travel school, of course.
Ray Gutierrez
Yeah, yeah.
Shayla Paz
So. But that was already two years in business.
Ray Gutierrez
Wow.
Shayla Paz
Yeah.
Ray Gutierrez
So what's next for you now?
Shayla Paz
Next for me is trying to get. I am going to get. No, I'm not going to try. I am going to get 40 people on board of my Norwegian jewel for the adrenaline Latin dance cruise.
Ray Gutierrez
Latin dance cruise?
Shayla Paz
Yes. 40 people. That will be my first big group. And then I'm taking a group of 16 to Ireland.
Ray Gutierrez
Okay, why 16 and 40? Why are those numbers 40?
Shayla Paz
Because the, the people who are working with at the Atlanta Salsa Congress, they did two of these cruises previously, and it was about 40 people. Is 20 cabins.
Ray Gutierrez
Okay.
Shayla Paz
So they did about 16 cabins. And I said, okay, let's add some extra ones because you need to have room for the professors. The instructions just put them in the kitchen.
Ray Gutierrez
Right. Isn't that. That works. Overflows the kitchen.
Shayla Paz
Yeah.
Ray Gutierrez
A couple conference rooms, but here's the conference room.
Shayla Paz
So you need to have some extra in case, you know, people decide the last minute to, to join. So you have to have some extra accounts.
Ray Gutierrez
Okay. I was just hoping you give me like, oh, 40 is like a numerical number that I use.
Shayla Paz
No, no, not really. I, I, you know, I would love to charter a cruise, but, you know, that will be like, how many cabins? Like 300, 500 cabins.
Ray Gutierrez
There you go.
Shayla Paz
I think it happen.
Ray Gutierrez
That it will happen.
Shayla Paz
Yes.
Ray Gutierrez
Give me your hand. Give me your hand right now. No, I'm going to smack it.
Shayla Paz
It will happen.
Ray Gutierrez
It will happen.
Shayla Paz
It will.
Ray Gutierrez
You're going to launch a cruise with 500 gas. Done.
Shayla Paz
Yeah. So you just, you cannot. Some people bark more than they can chew.
Ray Gutierrez
Yes, that's very true.
Shayla Paz
So you have to start small, but
Ray Gutierrez
you have to be ambitious when you start small.
Shayla Paz
Yeah, exactly. So this is a big step for me because I have done that, but it took me two years to get to that. So people are booking, and I'm very excited.
Ray Gutierrez
I'm excited for you.
Shayla Paz
And 16 is because. Is the smaller. Well, they actually, they have another number. I think it's 12. The group is 12, 16, 24. And then it goes up. They have different offer for the amount of people. So I thought, well, I'm going to go the second step instead of the first one because I get a bonus commission.
Ray Gutierrez
Nice.
Shayla Paz
And I get to go for free.
Ray Gutierrez
Oh, look at that.
Shayla Paz
So 16, it was the magic number. So I said, okay, all the perks. Nice. Perks. You want to get the perks, too, you know, travel with the people, get to meet your clients in person. A lot of my clients I don't know in person, but I know them because I talk to them. I plan their trips, and I know what they want and what they don't want, whether they like coffee or tea or, you know, the light architecture, you know, so all those things you need to know about your clients. So I want to get to know them a little bit more intimate when I travel with them.
Ray Gutierrez
That's awesome.
Shayla Paz
And then I'm doing a trip to Italy is 10 nights.
Ray Gutierrez
Wow.
Shayla Paz
In September. And I'm setting that up. I know that I want to do it, but I already talked to my tour operator about that.
Ray Gutierrez
Beautiful. Do you have any trips straight to the Ferrari factory in Italy?
Shayla Paz
I don't, but I can make it happen.
Ray Gutierrez
Please make it happen. Very VIP, just me and make sure Charles LeClaire and Lewis Hamilton are there. Okay, great, thanks. On that note, we're going to conclude this amazing podcast. Shayla, it's been such an honor. I've been quite. I'm happy to be part of your adventure today. And I hope that you feel like you're truly creating and building a legacy when you have the lights and the camera's on you. It's very much deserved and I'm happy to be part of your adventure.
Shayla Paz
Oh, thank you so much. And I hope that your venture take you to Cuba with me.
Ray Gutierrez
Yes, I would very much enjoy that because I've yet to go.
Shayla Paz
Yeah.
Ray Gutierrez
I need the right. I need the right guy, the Norwich
Shayla Paz
Star to show me the stars are always guiding us and gonna take us there.
Ray Gutierrez
Right on.
Shayla Paz
And to conclude my what is next. Cuba was always gonna be my number one destination. Even though that I expanded to other destination is always going to be there.
Ray Gutierrez
Bring it back to the source.
Shayla Paz
Yeah.
Ray Gutierrez
All right. And with that, keep building a legacy for inside success. I am Ray Gutierrez.
Podcast: Living Your Legacy
Host: Ray Gutierrez
Guest: Shayla Paz, Founder of Shayla Adventure Travel
Date: March 13, 2026
This episode spotlights Shayla Paz, a Cuban-American entrepreneur and the creative force behind Shayla Adventure Travel. Shayla shares her journey of using travel to connect people with meaningful cultural experiences, rooted in her personal history of family separation and resilience. She discusses her unique approach to immersive, transformative travel, how she creates “three trips in one” for her clients, and the business philosophies that underpin her growing legacy.
Motivation Rooted in Family: Shayla’s primary "why" is her family, dispersed internationally, and the lifelong effort of bridging those divides.
Cultural Influence: Shayla’s adventures and business are shaped by growing up in Cuba, navigating constant change, and helping clients understand what adventure and discovery truly mean.
Defining Authentic Adventure: Not just about sightseeing—it's about deep immersion into local culture, history, and people.
Memorable First Journey: Shayla’s first flight, taken alone for surgery, underscored the kindness of strangers and the Cuban spirit—shaping her belief in the transformative power of travel.
Understanding Clients’ Dreams: Shayla engages deeply with clients, asking about the motivation behind their bucket-list items to craft truly meaningful trips.
Mythbusting Cuba Travel: Dispels misconceptions about travel restrictions to Cuba and explains the step-by-step legal process for Americans.
Setting Expectations & Discussing Reality: Encourages open-mindedness due to cultural and economic differences with destinations like Cuba.
Journey Through Contrasts: Shayla brings travelers to both historic, restored areas and struggling local neighborhoods to show Cuba’s rich contrasts.
Travel Beyond Havana: Adventures include rural experiences, like trips to Vinales, revealing daily realities for Cubans.
Client Nurturing: Strong focus on post-trip follow-ups, addressing any issues, and inviting travelers to their next adventure.
Reviews and Certifications: Positive testimonials on Google and “Very Very Vacation” endorsed her business growth and credibility as a certified travel advisor.
Persistent Mindset: Shayla emphasizes the importance of resilience for entrepreneurs—staying focused on goals and repeating affirmation through vision boards and journals.
Vision Boards & Goal Setting: Encourages clients and aspiring travel professionals to map out ambitions step by step, visualizing their north star.
Upcoming Projects:
Vision for Growth: Dreams of eventually chartering a cruise for hundreds, while steadily growing.
This episode offers a warm, insightful exploration of what it means to design travel experiences that are not just bucket-list destinations, but opportunities for true transformation and connection. Shayla Paz’s story underlines the power of resilience, purposeful entrepreneurship, and embracing one’s cultural roots to create a business that brings people—and families—closer, one adventure at a time. Whether aspiring travel professionals or would-be adventurers, listeners will find both practical advice and heartfelt inspiration.