Do you dream of traveling for a living while working on your personal goals? This episode is for you. Today’s guest, Dylan Grace is a travel journalist, entrepreneur and media expert. Tune in to hear her serendipitous journey from working all over the world to the business she owns now. Dylan has appeared in Vogue, WSJ Magazine, Condé Nast Traveler, Travel + Leisure and many more!


Tune in to hear:


  • How taking the leap to move to the Middle East helped Dylan make progress as an entrepreneur.


  • Advice from Dylan on how to stay in line with your vision in pursuit of your dreams.


  • About the power of media in your business from a media genius!
Do you dream of traveling for a living while working on your goals? Today’s guest has advice for you! Dylan Grace is a travel journalist & entrepreneur.
Podcast Episode  

Transcript of Episode

Leah Gervais: Hey visionaries. Welcome back to the Your Biggest Vision show. I’m your host Leah Gervais and today we have a friend of mine, a wonderful client of mine, and quite a divisionary herself, Dylan Grace. Dylan is a travel journalist, a travel preneur and a media expert. She has so much wisdom to share with us. So thank you for being here. Dylan.


Dylan Grace: Thank you so much for having me.


Leah Gervais: Very excited to hear from you. So, um, you have done so much in your young years, you’ve traveled a lot, you’ve been, you’re very successful doing what many would consider a dream job. You travel for a living and you’ve made it your career. So I’d love for you to take us back a little bit. Um, maybe we could go to high school, college. What did you think you were going to be when you grew up?


Dylan Grace: So that’s a great question. Um, so I always had a propensity for writing. It was something that I just like helped me digest the world around me, go up in my room, um, kind of write down my observations and you know, so I always envisioned, um, some sort of writing path for myself. I actually, for my college application created a grace magazine with a photo of my mother and all of my little writing clips, um, from being in the high school newspaper, et cetera. So there always was this kind of common thread of women and my mother was a flight attendant, so travel, um, and writing from a really young age, I would say. Um, and then I, I don’t know, I mean we can get into this little bit later, but I wondered like, how could I make a living off of writing? Um, what could that look like? Would that be possible? Um, so that transition from a passion into sort of an actual career, um, was a little less known, I would say from an earlier age.


Leah Gervais: Okay. So you’ve always loved to write, but you just didn’t know how it would turn into a career. So you didn’t really make it a career in the beginning. And so I happened to know you didn’t go to school for journalism. Um, what did you decide when you were going to school? Was it like, I’m going to do the responsible thing or what was kind of going through your head at that point?


Dylan Grace: So I was, I was an English major. Um, but it didn’t have a specific, um, journalism focus. I was thinking potentially a prelaunch. That was my minor. Um, I also had a philosophy minor as well. So kind of the world of, you know, philosophy writing, pre law. But law seemed like, as I know, you can relate to I safe, steady, you know, path to choose for myself. Um, so that’s what I think I was really considering throughout, throughout college.


Leah Gervais: Okay. And so what was your first job when you graduated?


Dylan Grace: So this is a great question. So I was always in school. I’m responsible for my, you know, any costs that I had associated with going to college. My books. Um, you know, taught to be super independent. So I was a nanny all through my college years and um, worked with some great families and in the summers would nanny. So my first, like one of my big nannying jobs, I lived with a family and the woman was in human resources and at the end of the day, like after the kids were asleep, her and I would always chat. Um, and she was like, Dylan, I think that you have a great propensity for, uh, training and development and onboarding and working with people and listening to people and problem solving. She was like, I think, you know, maybe human resources are changing and development could be a great path for you.


So she introduced me to that sort of world. Um, and I ended up getting a, my first internship out of college, uh, at coach, the handbag company where I worked, um, as an assistant to the head of training and development there and um, kind of Rose through the ranks a bit in that first job and ended up being the person who like onboarded you on your first day in coach. So golf culture, welcome to coach, like got everyone hyped to be there and excited to be there, which was an a, I mean, I loved it. It was so fun meeting new people and, and um, learning about how teams were, um, et cetera. So that was my first job out of college.


Leah Gervais: Wow. Okay. And it’s so funny now, like kind of knowing you so well and hearing that those are your strengths. Like I can see you being so great at it, but then being like, I’m not going to do this. So you have a whole life, like you imagine, you know, massive sprawling company. Um, a lot of, you know, corporate policy is, and so it was, it’s, it’s always like five, I would think of that journey. Right. So, um, so zooming in a little bit, so at this point, you’ve graduated college, you’re living in New York, right? Cause Curtis in New York, I assume. Yeah. You, um, you know, you have a good job. Like, I know that not everyone gets these jobs, but then somewhere along the way you kind of decided that you’re gonna not do this anymore. When does that happen? And I’d love to like really hear the specifics of when the voice thing you started and how you kept listening to it.


Dylan Grace: Yeah. Um, so my story is a little bit unusual. Um, I was working at Coach that was for about two years. Um, and I actually met someone and um, he was living in the middle East American and I had this opportunity to, to move, um, and honestly like it took me six months to decide I’m from Connecticut, my family is like, Dylan, what are you thinking? But truly there was always this part of me that wanted to explore. The world was taught to go see the world. That was curious just about how I had been raised versus how other things could be. Um, and although it didn’t make sense, it made total sense to me to make this move. Um, and that kind of started what would be like the next chapter of my life. Um, and also, you know, we ultimately ended up breaking up. I ended up staying for six years living in the middle East. Um, I got my first journalism job. Um, working as a culture editor into BI, um, and got a little beach bungalow and you know, a little studio and kind of found my way really there. So I always say it’s the wrong path to the right station.


Leah Gervais: Hmm. Oh my God, that’s such an awesome story. Especially that you stayed like, you’re like, okay, I’m going to keep doing this. And so when, when you were living in the middle East, did writing come back into the picture and you start to realize like, Whoa, everything actually might be working out the way. I never knew I wanted it to but wanted it to.


So I think like again, just as writing as a way to observe this new environment that I was in, um, I was like [inaudible] writing about everything I was seeing. Um, just like digesting being in this place that was so far from home notebooks and notebooks and notebooks full of writing. But again, on a more personal level. Okay. So I originally moved to Beirut Lebanon. I was there for a year and ended up getting a job. Um, again, like my path is extremely serendipitous, but some things, um, I, my job in Beirut was actually working for Elie Saab, the fashion designer. Um, he is like an amazing couture designer and I got that job because I was sitting on a beach in India actually, um, at like a yoga retreat and just happened to meet a woman who knew Elie Saab and about my coach and my passion background and was like, you would be perfect for Elie.


So I was the only American working in Beirut. Um, and you know, fashion has always been something that I’ve also been like interested in. It kind of pulled at me and got to work with that family in Lebanon. Um, and actually for personal reasons, there was a bombing that happened, like very close to, it sounds like a movie when I’m talking about this. It’s almost surreal, but, um, you know, there was, it was, it was close to where I was living at the time and my family was like, Dylan, we’ve supported you. We’ve had your back, but we don’t want to see your neighborhood like on the nightly news. Fair enough. Right, right. And I really thought about that and Dubai was someplace and I’d been working with journalists in the middle East and like internationally and I loved this one magazine and Dubai and I just reached out and was like, I would love to, um, you know, is there any open positions? I ended up sending through no personal writing and the editor in chief like I guess saw something and ended up taking a chance and I um, she groomed me and I ended up extending their features editor and that’s right.


Leah Gervais: Wow. Okay. What an amazing story, Eli Saab. No big deal, just this guy that you met. It’s just incredible. Um, okay, so your, what I love about, you know, your story and knowing you well is that like I know that you believe in kind of like divine timing and things like that. And do you think that a lot of that has come from like every, all the proof that you have about when things have just like shouldn’t have worked out for you but then has like how do you feel like as you’re telling these stories now that’s changed you as a person now and as an entrepreneur now because you’ve been shown time and time again that things have a way of working out?


Dylan Grace: Yeah, I think, um, there’s a few ways, you know, you and I have talked about this one. I think making that level of a leap so young really helped me have a point of reference for leaps moving forward. Like sometimes I’ll laugh and be like, I moved to Beirut. Like, I can do this, I can get on this call. I get you right. Like ha, like doing something that drastic, um, always serves as this thing I can fall back on and feel so proud of, you know? And I also think when I was writing in those little journals when I was younger, when I was dreaming about seeing the world, I had no what that can look like or what it might mean. But it’s always like my dreams. It’s always ended up even better and bigger than I could have imagined. And I think that I like hold on to that and I choose to like day in, day out believe that, um, I’m moving towards the path. Um, but sometimes the path is even like more incredible than I could know.

Leah Gervais: Mm. I love that. And I so, so resonate with that. I have had things like that happen in my life along the way where, yeah, when I kind of tell it back, I’m like, this sounds like, Oh, this sounds like a movie or this just sounds like it doesn’t actually happen. But it does. And the thing is these kinds of things happen to all of us if we like open our eyes and look for them. If you have tunnel vision, that’s what I really believe. If you like, don’t have that open mind or that open way of seeing, then you won’t see it. But that doesn’t mean it’s not there. That doesn’t mean that like I got my first job out of college from someone that I met on the beach in Nantucket when it wasn’t even supposed to be there and it was totally cool. Like of all the places I applied, right was just like, you know, and I’m still very close with, you know that guy, he ended up coming to our wedding. And so all of those things happen. But unless you like decide to talk to the person who has the dog that you’re playing with, you’re never going to know that they own a law firm and that they’re looking for a paralegal and you’re interested in law school and you’re never going to go.


Dylan Grace: Absolutely, I couldn’t agree more.


Leah Gervais: Beautiful. Okay. So let’s speed up a little more to where you are today. So you have, you know, ended up becoming a very successful travel journalist. Tell us a little bit about, you know, what, what along the path is most meaningful to you? Like, in terms of deciding to come back to the U S deciding that you’re going to continue on and, um, you know, ending up transitioning from what it sounds like was a very stable career in different, not a stable career, but a stable nine to five job in Dubai to freelance writing.


Dylan Grace: Yep. Um, so for personal reasons, I was ready to come back to the state. It’s, you know, it was one of those times in my life, kind of an inflection point where my grandparents are getting older, my, you know, friends are getting married and I was missing some kind of key life events. Um, and so I just decided to come back. And, you know, one of the biggest parts for me of moving to the Middle East was the friendships and the people that I met while I was there. And growing up in Connecticut and in New York and, you know, even being in a 9/11 environment, um, I just had my world flipped upside down in terms of education and knowledge and, and really, um, getting to know the Middle Eastern culture. And when it came back to the U.S. it felt really important for me to be sort of an unofficial ambassador for all of the amazing people that I had met there and the experiences I had had.


So I started writing a lot about the middle East for, you know, everyone from Conde Nast traveler to WSJ mag and kind of from a new Yorker’s perspective, this is what I experienced. And, um, with writing in general, I think that always feels like a big part of my purpose is just showing a place in a new lens. Going back there, flipping some of them maybe like generalizations and finding that like beautiful nugget of like even humanity, like just shared humanity. And that’s why I travel writing and, you know, um, has always been like such a big part of who I am and what I love to do.


Leah Gervais: That’s one of my favorite things about you and what you do is that it’s so clear that you know, you do love to travel, who doesn’t love to travel, but you’re so, um, clear within your work and it comes off so genuinely that you love travel because of what it has done for you, what you think it has the power to do for others, why you think it can have a positive impact on society as a whole. And I feel like for you, travel is the means to that end. It’s never just about travel for the sake of traveling. And I love that that has, you know, continued to guide you as you’ve done so many different things with your business. 


So, um, you have now written for people  like Conde Nast and Vogue and really publications from, you know, just having this experience and having this sort of duty that you have felt to spread this message. Um, and I guess just kind of summarize for us like last year because that’s kind of like what I know the most about your business and how things have shifted. And maybe some of the ways that you have had some stumbles when it comes to, you know, creating a brand that is not just Dylan and a journalist or Dylan the writer, but like Dylan, the person who cares about the power of travel and what that means across all platforms. Um, and just what that looks like. I’d love kind of like an inside look.


Dylan Grace: Yeah. Um, so it’s been, it was really interesting. I think when I first got back it was an amazing opportunity to just write for these publications. I had grown up everything that I dreamed of and I’m always grateful when I’m on assignment and I get to take my family and you know, I brought my dad to Bora Bora recently and I’m getting paid to go see a place and to be able to bring a loved one is like the dream situation. I started to think about, cause I predominantly focused on luxury travel, which is not a bad beat to have. Um, but I, you know, I was thinking like this and I think a lot of entrepreneurs feel this way. I know you and I have had these conversations, like this is a part of me, I love this like beautiful luxury travel lifestyle, but there is this other part of me too that is very interested in personal development as interested in serving and, and, and mentoring.


And I had a lot of people coming to me saying, Dylan, how did you get started? You know, what, what are some steps? What can I do? And it took me a while to sort of figure out how I could fuse these two things because at least in my world, and I think it’s quickly shifting, um, as we build businesses around just who we are, it wasn’t clear to me like this luxury magazine journalism path, how that could fit into like a coaching, uh, personal development, um, uh, serving sort of, um, career as well. And I spent a lot of time on this and thinking about it, I actually had a Venn diagram where it would be, um, like the two different sort of sides of myself and how those could cross over. And I was just really focused on that middle piece and I just knew that if I really thought about it and I, you know, focused on wanting to find an answer to that, it would kind of come together.


And I, it, it took, you know, I would say like several months. So just thinking and brainstorming and writing down what I’d like to do, who I like to do it with until I kind of came to this travel coaching, um, which is a combination of my two biggest passions. Like how can people transform and work on their personal development goals through travel, the experience of travel and, um, it’s just been rapid fire since then. Um, it, you know, I had a beautiful profile in Forbes recently about the work that I was doing and getting to just help and work with so many incredible people around the world has been truly like figure again than I could’ve ever imagined.


Leah Gervais: Mm. It’s been awesome. You know, kind of being in the front row or just seeing what you, what you’ve done in a quick amount of time and just continue saying yes to what you’re good at. And I think that that’s one of the secrets that’s not secret, but yet people make it really complicated about entrepreneurship is just not continuing more of your strengths and not paying more attention to your strengths. And I think we really over-complicate what we think we need to be doing because we see what other people need to like are doing. And that’s, that’s fine, that’s not their fault. Um, but it can, we need to have the awareness to know that our momentum comes from what we’re good at. And you really said yes to that so much lately. And um, you know, another thing I think you’ve done so smartly, and this is something I teach a lot with my clients and just in general, is to think about how you can add different income streams based on what you’ve already done.


This isn’t about putting pressure on writing a book and speaking on 15 different stages and you know, doing all those different things, but like one of my favorite, one of the things I love to do is you know, is think about how can I get better at what I do and then how can I potentially teach what I do, like let’s not overcomplicate it. Just really thinking about those basic things and you’ve done a great job with that. And by the way, for anyone who’s listening to this in real time, we are in the thick of this pandemic here in New York. Dylan doesn’t live in New York. She’s safe in the North, in new England right now, but we are really, really in the thick of it here and this is one of the things I’m most recommending to people wanting to stabilize their income a little bit is to look at what I’m good at and think about how you could maybe teach someone else to do that, especially if that would be in service. I’m kind of digressing. My point is I’m pulling out things you’ve done very well over the past year.


Dylan Grace: I think that’s a great point. I also think one of the big aha moments for us working together too is that some of these things that you just do and you, it, it’s like easy for you to do. I think we’re taught like it should be hard. Like you should write like work and income like we should, it should be really hard to like get that paycheck and we almost take it for granted the things that just come so easily and the skillsets that come so easily. So I think like taking stock, taking inventory of that and then knowing that like that deserves, you know, that that is a skill set that that could really help people and, and, and deserves monetary value. I think that that’s been something that I’ve been really realizing and working on um, over the last year too.


Leah Gervais: Hmm. I love that. 


Dylan Grace: So well put and definitely, you know, stepping into your worth is work, but it’s worth it to do that new, I feel like it’s, it really comes from you, like, and that abundance mindset and attracting those opportunities, it’s faster than you could ever even imagine.


Leah Gervais: Oh, totally. Totally. I love this stuff. So what about some of the challenges you have experienced going through this? How has there been, you know, maybe some voices that have come up again and again and maybe that you don’t even recognize anymore because you’ve said no to them, but what are some of the things that people might be, you know, maybe they love listening to you, they resonate, but when they actually try to put one foot in front of the other, something stops them. Did you have anything like that?


Dylan Grace: That’s a great question. Um, I think that there’s a few things, like, again, I can’t stress this enough, just like traveling and taking that leap, um, has really almost laid like a foundation for how I make decisions in the future. Because, um, I trusted myself even though it didn’t make sense. And coming back to that trust with myself, I feel like it is such a fundamental piece of like being an entrepreneur and building a business. So I guess my recommendation would be, it doesn’t have to be moving to be rude. It doesn’t have to be with you by right. It doesn’t even have to be that extreme. But what are exercises that you can do to help just build trust with you, right? Like to just day in, day out. Like have your own back and know that like as great as the advice you’re going to get from other people at the end of the day.


And there is an intuitive level of like knowing what your path is. And I feel like especially now kind of pioneering this new space of travel coaching and building my business that trust is fundamental. Knowing that I see a vision, I see how I can go when it’s not really existed. Thus. Um, and I think for a lot of entrepreneurs just that it’s, it’s not even like there’s that level of like crazy dreaming which has to be there, but also just inherent trust with your vision, with yourself, um, to, to get you where you’re going.


Leah Gervais: Hmm. This is such, such good advice. And what I would actually maybe say is the most fundamentally important thing if you want to be successful. And I’ve talked about this on the podcast a few times and some things that we recommend, you know, to, to, to build that are even small things like just do what you’re going to say throughout the day. If you say that you’re going to go to the gym, then just go. Like, just having that small reliance on yourself to know that you will not self abandon and you will come through it builds a muscle that’s so much deeper than we think. So I love that you share that.


Dylan Grace: I do also like just on a sort of, um, you know, I know a lot of people are doing this now too and I truly think it like hardwires your brain differently. But I do a gratitude journal every morning. I never repeat anything twice. It’s my rule with myself. So it forces me to get like really specific with what’s going on. And I do like, it’s just laying those stones. Right. It’s like once you’re already rolling towards this abundance mindset, this gratitude that you have, everything that you need, it’s sort of like naturally allows you to kind of be braver and get even more because you’re already in that mindset of I’m just feeling like so lucky.


Leah Gervais: Exactly. Awesome. So looking, um, a little bit, you know, to where you are now and having the success in media that you have. Um, I know that you are, you know, you work with people to help them understand how to get in the media, especially entrepreneurs, especially travel entrepreneurs. I’d love to hear some mistakes that you see people make. Um, and maybe just some pointers for someone who is feeling intimidated about though


Dylan Grace: I, um, could not, like I love talking  media. It is my favorite topic. I have seen it skyrocket my own business. Um, and I just think like the opportunity now that we have, especially in the digital age, um, to get our message out to a lot of people is incredible. I’m really trained specifically as a digital editor. So, um, I think in that sort of mind frame and that lens, I think the biggest mistake that I see is at the end of the day, like any good entrepreneur, really thinking about, okay, what are the audiences and the reader’s pain points? What do they want to know and how can you serve them? And I see a lot of people come into it like, okay, how do I get my message out? How do I talk about my work? And I never approach a story like that.


I try to think about, okay, what are the things I was curious about when I was starting out? What are the things, you know, depending on the publication and the demographic, they would want to know, how can I, what I’m doing best serve them? Um, so I think that reframe of like getting into the reader’s mindset and then getting into the editor’s mindset, how can I make this as easy as possible? How can I make this so it’s just a yes. And that can be everything from, you know, being considered of your email length to providing imagery if you have it, if it’s a travel story. Um, so just really thinking about pretty much, even though it’s your work that you’re promoting everyone else and how you can make that as easy as possible for them.


Leah Gervais: Mm. That’s a great tip. So do you feel like too often people are just stuck in what they think they should be writing and not rarely thinking about like how it’s being received or the value it’s providing is kind of what you’re saying?


Dylan Grace: Yeah, and I would say kind of, um, getting out of that like tunnel vision of what you want to get from it. Like if you can think about what the reader can get from it, that’s always going to make for a stronger story. And if you do your homework and understand how that publication presents its stories, how it writes its headlines, et cetera, that’s going to make for a strong relationship with the editor. So it’s actually sort of just taking yourself out of the equation, letting your work speak for itself, and then letting your work resonate with the readership and the editor versus just trying to drive home a sales pitch.


Leah Gervais: Awesome. Really great advice. And for our audience here of entrepreneurs, mostly online entrepreneurs, what type of tips or you know, best practices do you recommend for people to be thoughtful about how media is connecting to their business? One of the things I will talk about at nauseum is, you know, driving people back to an email with us. It’s so important to grow your email list. Um, do you have any things like that that you see people not really thinking correctly on when it comes to media?


Dylan Grace: Yeah, I think that’s a great point. I would say it’s not a “write the article” and then you’re done. Like there’s such a way to leverage your media wins. Um, for example, you’ll see on my website, on your website having the local news, um, that are, you know, displayed, um, sending the article out to your email list I think is a big thing, um, that people can do, um, promoting it on social. Um, so making sure that you’re considering that article also as a marketing tool for years. Um, and I think that that, that’s like a, it’s a whole sort of, um, full circle ecosystem and you should be thinking about it that way. And that’s why media can be so powerful. Right. It’s more than just the one off story.


Leah Gervais: Right. Awesome. Well, media genius here. It’s so, so great hearing from you about this. Um, do you want to share a little bit about the media work that you do with clients specifically or do you feel like you’ve covered it here? Whatever feels good to you.


Dylan Grace: Yeah, I’m, I would love to. So as I’m sort of, you know, moving into the next phase of my business, as you know, I do a lot with, um, those interested in travel entrepreneurship, which is an absolute blast. And then I am, I’m doing a lot more and I do one on one work. Um, and you know, Austin B, uh, had also rolling out a mastermind program for those interested in learning the ins and outs of media, kind of understanding how to wrap up their stories in that perfect gift to the editor. Um, some best practices and yeah, just being their biggest champion and workshopping with them on their pitches.


Leah Gervais: Oh fabulous. Well, people should be lining up to have you do their media with them because you know what you’re talking about and you can clearly see like the bigger picture and the bigger, bigger functionality, which is obviously so powerful. Um, okay, this has been amazing. I have a few lightening questions for you. Are you ready? Yes. Okay. So as an entrepreneur, what is your go to when you’re having a bad day, things just aren’t going right. 


Dylan Grace: Exercise.


Leah Gervais: Exercise, that’s a great one. Exercise. And what do you consider some of your, what are, I’m going to actually ask you for three of your proudest business moments thus far.


Dylan Grace: Ooh. Um, I would say being published in Vogue is this is a lifelong dream of my, um, anytime that I’ve traveled with a family member, I mean I’ve brought my mom to Ireland. Um, you know, I brought my brother to Aubu Daubi. Um, anytime I’ve been able to be on assignment, uh, with family. Um, and I would say my third one is…


Leah Gervais: I can think of it for you. I know it’s always easier for someone else. So what would you say about what you’re doing right now? No, you’re like completely added a new pillar to your business. So it’s been super successful. I mean, it’s been amazing to see what you’ve done.


Dylan Grace: Yeah, I think like pioneering a new space, I would say it’s been incredible. Um, incredibly exciting roller coaster of, um, entrepreneurship and I’m excited for what’s ahead.

Leah Gervais: Awesome. Great. Okay. And do you have a, an entrepreneurship book or podcast that has really helped you, that you recommend?


Dylan Grace: Not particularly, I mean, apart from you. Um, and apart from our work together, I would say I love, I’m very into, uh, Tara Brock. She’s a Buddhist teacher. Um, I listened to her almost daily. Um, and although it’s not specifically about entrepreneurship is just about human psychology. Um, and I find that to be super applicable to business too.


Leah Gervais: Love that. Love that. Okay. And where can people find out more about you?


Dylan Grace: They can find more on a and they can follow me on, um, @DylanGraceTravels on my Instagram.


Leah Gervais: Great. And we will have links to both of those in the show notes so you can always find them on my website. Dylan, thank you. Thank you for sharing your story. Thank you for sharing your perspective. You’re proof that things are constantly working out for us. Um, the bravery that you’ve had by saying yes to so many different things and your media brilliance. It’s been awesome.


Dylan Grace: Thank you so much for this opportunity.


Leah Gervais: Oh my pleasure. Alright, visionary. So I hope you love this as much as sighted. Go check out Dylan’s Instagram, like have some wanderlust. Especially right now if you need, there you go. Because this pandemic will be over and we will be able to travel again. So she is there for you and here is to your biggest vision. I’ll talk to you all soon. I hope you are all happy and healthy whenever you’re hearing this. My heart is with each and every one of you during this time we’ve got this.


Show Notes:



Instagram: @DylanGraceTravels

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