Today’s guests on the Your Biggest Vision Show are Anna McNaught and James Bonanno, founders of Leave the Map. They are here today to talk to us about pivoting through entrepreneurship, starting a brand together and what it means to work together as husband and wife and business partners. They also share what it has been like to pursue travel in the thick of a pandemic and how they have continued to stay aligned with their vision. 

Tune in to hear:

  • How Anna and James combined their individual entrepreneurial pursuits to create the platform they have together today.
  • How Anna and James have found stability and freedom in their business while traveling full time.
  • About the launch of their 90 day mastermind coming soon!
Tune in to hear Anna McNaught and James Bonanno, founders of Leave the Map, share their entrepreneurial journey as full time travelers and husband and wife.
Podcast Episode  

Live Replay

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 two of my best friends to come and talk to us. Anna McNaught and James. James, how do you pronounce your last name? 


James Bonanno: Banana. Bonanno. 


Leah Gervais: Like how do you pronounce it?


James Bonanno: I probably pronounce my own last name wrong. I feel like I say Banano. No, but like if you’re really Italian you’d be like Bonanno you know, so like, yeah, you don’t have to say like that. 


Anna McNaught: I truly don’t know how to say it. Usually I’m just like, Oh yeah, James, uh, James, my husband.


Leah Gervais: So Anna and James are husband and wife. They are the masterminds behind the travel platform, Leave the map. And I’m really excited to have them on the show for so many reasons. Many of you may know who Anna is because she’s actually been on the show before. Um, and she’s one of my best friends in the world and I wanted them to come on and talk about their journey of pivoting through entrepreneurship, starting a brand together and what it means to work as husband and wife together and business partners, uh, pursuing travel in the thick of a pandemic, which at the time of the recording we’re in right now. Um, and just really the example that they’ve set of continuing to say yes to themselves, which I think you guys are really to hear, especially in the last year. Um, they really followed their guts in a way that’s just super inspirational. So thank you guys so much for coming on and sharing it with us.


Anna McNaught: Of course. Thank you for having us.


Leah Gervais: My pleasure. All right, so, um, you guys, let’s take your story back a little bit. I know both of you have a lot of entrepreneurial, um, pursuits and you know, you’ve done a lot. Uh, but I would love to focus on you guys working together. So you started this platform, Leave the Map, you know, last year in 2019. Talk to me about what was going on during that time and, and hi guys to start or to start working together.


James Bonanno: Um, okay. Yeah. So I’ll, uh, I guess I’ll start and then we can just bounce off of each other. But, um, leave the map as a page before it really became, a full fledged business started as a feature page on Instagram. Um, Anna and I have always been passionate about traveling and even before we could get out there and do it ourselves all the time, we wanted to showcase others that were doing that. Um, and that’s really how it started. 


Anna McNaught: That was actually in 2017. We came up with the name and we’re like, let’s just post cool pictures. 


James Bonanno: Yeah. So that was a, that was like almost three years ago that we decided to do that. Um, and it was a very slow burn. Like we, we didn’t really know what we were doing. Um, we had our own pages built, you know, I had my account, Anna had her following, um, continuing to grow with her. Anna Menotti, um, you know, digital art page. And, uh, we sort of, I don’t know when the train, like when did we really decide to like transition into posting our own stuff? 


Anna McNaught: Well, I think we were kind of starting to share like pictures from our weekend travels and everything because you know, we’re both still working full time and they are pictures are just bad and not edited well. And I was trying to copy the blogger look and totally overexposing things like very just like blown out and really, really poor quality. Um, and I think it was maybe not until the beginning of 2019 and um, around there that we started to like to take it seriously and be like, let’s kind of pay attention to how we’re doing this in our editing and like the quality of pictures we’re creating.


James Bonanno: Yeah, I get, well I guess, um, we got married in September of 2018 and that was kind of when we took a small leap into a more like travel focused content. I mean most everyone has different honeymoons and different ways of doing that. But our, what we chose for our honeymoon is to rent a camper van and spend like, what was it, 14 days, 14 days driving from New Jersey where we got married back to Los Angeles where we were currently living.


Leah Gervais: I call that type B fun, be fun. 


James Bonanno: Yeah. That’s not Leah Fon. That’s more like our cup of tea.


Anna McNaught: Yeah, it was pretty funny and like, especially cause the van we rented was so small, like it wasn’t high top so he couldn’t stand up. We were like getting dressed laying down and we had like a little rooftop camper that we’d climb up into and every night like super romantic.


James Bonanno: I was going to say, so romantic.


Anna McNaught: Although I think the one night we were in the grand Tetons and like that place will always hold a special place in our heart. And we um, we found this like really quiet, uh, kind of like off the beaten path campsite and no one was around and we parked the van and our view was looking out over the field with the grand Tetons in the background, like surrounded by pine trees, pure, peaceful, quiet. And like it was a crystal clear night. The stars came out, we had our campfire, we were all set up. And that was one of those moments that we were like, Holy shit, like this is everything. Like why are we not doing this for a living? Like, and we see so many people doing it, why can’t we do it too? You know? And then after that it was like brainstorm, brainstorm, brainstorm. 


James Bonanno: Yeah. That was kind of, I would say that was like the launchpad of when we chose to, cause we got back to Los Angeles and I think felt differently when we returned to this apartment and to a life that I was still working a corporate job. Um, you know, and super busy doing that. And also then trying to manage like the side business and we both really decided, okay, let’s like use the honeymoon, let’s use the photos and the content that we got from this trip as a way to try to like, uh, you know, jumpstart the next trip and, and like just put one foot in front of the other and see what happens. Um, so I would say that was really when Leave the Map was in, it’s like second birth. Like that was really when it started I think as more of a business as opposed to just like a feature page.


Leah Gervais: Right. Okay. So you guys have this adventurous honeymoon and you start realizing like, Whoa, you know, we are living a double life essentially. Like we have our life in LA and it’s fine and we’re happy there but then we have this weekend life, this vacation life and it just feels like it’s out of alignment and why can’t they kind of be sinking up. So you’re living in Los Angeles, I know Anna you were full time at the, or you were already full time on your own at the time, but you’re still working like a pretty prestigious job in LA. And so you know, I remember this in real time, but there were a few months there of you guys trying to wrap your heads around giving that all up and leaving LA James quitting his job, working together. And so what were some of the challenges that you guys were facing or that you guys talked about, about getting on the same page and really putting that into action during that time?


Anna McNaught: Yeah, I remember that was a rough few months after our wedding. And I remember talking to you, Leah on the phone and everything and being like, I don’t know what I’m doing. Like we just had this crazy awesome adventure and like now I’m totally lost in my business and like James is back to work and I’m alone again. And I just, I feel like everything that just was so incredible has just crashed down for a few months. And I remember I was just like crying and like so upset and I think we just like, we kept facing these challenges of like, one like how can we make this a reality? Like what steps do we actually need to take and really being stuck in our own heads. 


James Bonanno: I would say that was that you, you hit that wall way before I did like you were hitting it because Anna, like you were already working for yourself and I was working for myself on the side, but I always had the luxury and the stability of a full time, you know, well, good paying job that we were able to sustain a life out there. But what we were missing was like, I no longer had the passion that I did when I first started this job and it just became like a routine. And our passion, which we realized long ago was like, okay, we want to do a lot of these things as photographers and continue to work for brands, but we don’t want it. We want to do it on our time and we want to have the flexibility to travel whenever we want because the feeling we had, any trip we went on was always the same.


We’d get back and we’d be like miserable because we knew that what we left behind was what we should be pursuing. Um, and so that, that took both of us a while to get there and then once we were there to actually like execute it. And for me personally to say in order for this to happen, I not only have to leave my full time corporate job but we have to leave Los Angeles because we don’t really have a way to afford it if we stay here, we then have like we were in the process of researching these vans. So there were all these things that were happening simultaneously that had they happened in like different orders I think would have changed, changed the way in which we left and did our own thing. 


Anna McNaught: Yeah. And it was almost like the way everything hit at once and kind of like the stress around it all really helped push us to keep going forward. And then when we had a 7.1 earthquake I was like, Nope, we’re out. I don’t care. I don’t care if we were thinking of staying here for months longer, we are done.


Leah Gervais: Totally, well, I can really relate to that moment you guys had on your honeymoon because I, I’m like when I had started Urban 20 Something, you know, that’s a whole nother story, but it was just kind of like this. I would dabble with it around my nine to five job, kind of seeing if it would work here and there and I get down on myself cause I wasn’t making as much money as I thought I could or as other people were. And it totally makes sense to me now because I was like half asking it, which, which totally explains it. But, I remember like that moment, my equivalent of that moment was a trip that Adam and I took to Barcelona when it was like over Thanksgiving and I ran a black Friday sale successfully. And for the first time in my life I had kind of like meshed traveling with my business and it completely shifted my view of what was possible because I had always not only felt like that double life, like I have who I am on the weekends and what I’m passionate about and when I’m happy and then work and like there’s always like work was funding, you know who I was.


And I thought that that’s just how it was because for a lot of us and for our parents and for a lot of what society tells you that that is the truth. And so I hope that the, like, I think the first nugget of wisdom from you too is that, you know, you guys questioned that and you had the bravery not only to think how could we, how could this not be the way it is? Like what would it look like if this was all one? But then you guys actually sat down and thought, okay, what do we need to do to make this happen? How can we quit our jobs? So to anyone out there listening, if you relate with that, you know, push and pull, kind of like, I like doing this but I have to do this. You don’t have to do that.


You can literally stop listening to this episode right now. Pause it, come back, this is going to be good. But write down what do you actually need to do to amend that life? So, okay, so you guys are in LA, you start thinking about how you want to leave. James needs to quit his job. Like you kind of have this really daunting to do list and I’m sure that, and you’re newlyweds and so you’re dealing with like how to navigate this all. So what were some of the first things you guys started doing business wise too? You know, set yourself up for success?


James Bonanno: Um, well I guess for me, um, and Leah, like we’ve had this conversation before, um, as you helping us as, as a, you know, a mentor and a coach as well to just continue to like push forward in this way. But for me it was like at first was a mental block. It was this mindset, um, to get past certain things. And one of those big issues for me was the financial stability that I had worked so hard for and had my whole life, never gone from like one job without having another one to fall back on. And that was something that was instilled in me as a value growing up and I’ve just, that’s just how I was raised and operate. And so for me to like change that took a really long time. Um, and once I realized that I was still getting client work outside of my nine to five, um, then there was actually proof that like what I was doing was working. And I think there was a few months at the end that I was making more money freelancing than I was at Verizon. And I think like one month I, before we left, I’m like, Holy crap. Like, if I were to put my all into this and dedicate all the time, like I know it’s working, I just have to stay to myself, I can do it and take the jump. So, uh, for the people that worship stability, I 100% stand behind that because that’s how I operate. But I also realize that there was another world that if we wanted to make this a reality, I had to get out of my own way and just say, let’s just try it and, and take a risk that hopefully, you know works.


Anna McNaught: Yeah. And I would say in terms of like actually building the business and whatnot, we focused a lot on like, you know, what our content looked like to, you know, like what, you know, how we were editing the photos and like if we were making sure we are using a camera when we take photos and not like our phones and, and just like little things like that to really like up the ante and be like, Hey, look like we’re really good at what we do. And like, you should hire us. You know, and like trying to build a portfolio around that and whatnot. And then I think for me the other thing was like, I greatly suffered from self doubt and not seeing like what I was doing, um, in the past and like being grateful for the place I was currently in and like just my own potential.


When I was in Leah’s mastermind, that all kind of like came at me so fast that it was like a very emotional six months. But like, it really, really helped me to truly understand my potential as well as my money mindset too because um, you know, we had always kind of talked about like, Oh well and like what James said about stability. Like we need to make sure we have consistent money coming in and like money in the bank and like, you know, can we afford this blah, blah blah. And we just were thinking about it in totally the wrong way rather than like, you know, the potential of like what there was to come and like we are just hitting our ceiling and not able to break through it. And I think like Leah, your mastermind helped me to just understand like what I can do. And once I understood that for myself, I stopped buying “how-to” courses. I stopped reading like emails. I stopped Youtubing, everything. I was like, I have all that information within my heart and within my head and all I need to do is just take action.


Leah Gervais: Oh well thank you so much for sharing that. You know, obviously that moves me a lot and it was amazing to see you stand out of your own or you know, move out of your own way and you know, I adore you and have always thought so highly of you. And to see you just, you know, double your income like in the second month that you were in that mastermind was, was a joy. And you know, I think one of the things that’s really special about you two and I know that you now help other people that want to do travel related businesses and you guys have so many diverse skills within that niche, but the couple of you together, like just the kind of the struggles you just highlighted. Like James, you know, having to think differently about security and having to realize that security’s a value he had.


But there’s other ways to find security than a nine to five job. I mean now a great example, you have way more security in working for yourself than you edit a nine to five job because we’re in a recession, people are getting laid off left and right, so you have so much more security and you know, then Anna needing to like realize her own potential. You guys have always really played off of that while with each other and always been each other’s number one fan with that. Like, I’ve always seen Anna, you know, talk to James about what he really cares about financially and when was security and, and she like has always been there for him. Finding that out. And same with James, always believing in Anna and always thinking of like the highest version of herself. And so you guys being able to do that together and kind of, you know, know that you want the same things but have different ways of maybe seeing them I think is what makes you guys so powerful as a couple and business owners. And that’s why you’re so good at mentoring other people too because you can kind of like level with wherever they’re coming from, get to the bottom of what the value they have is and then think of what it means to get there in a way that they might not be able to. So you guys are incredible.


Anna McNaught: Oh, thank you. 


James Bonanno: Thank you. 


Anna McNaught: I am going to get teary thinking about all of this and the journey, it’s like it’s so, it’s so awesome. Thanks for saying thank you Leah. 


James Bonanno: It does feel very like genuine. And, and I think one of the, one of the things that we feel most proud about what we’ve created and what we will continue to grow is just like how authentic we are. And some people can say they’re authentic and then not really show it. From the beginning we’ve always just really wanted to have this brand and this message of doing good in the world and of, you know, helping people to build a business that reflects our core values. And you know, Anna and I, like you said, really bounce ideas off of each other 24 hours a day. Like she was up at like 1:30 in the morning last night and I’m sleeping and she’s like “what do you think about this” and she is on Tik Tok showing me. And I’m just like answering something self consciously.


Anna McNaught: He was answering in his sleep, he doesn’t remember. And I was like, Ooh, this is cool. What are you, what do you think of this? 


James Bonanno: So yeah, we’re constant, constantly, constantly, um, pushing each other. And I think sometimes that’s always a good thing. Sometimes we like, maybe get frustrated with how we’re doing it, but the end goal is always pushing each other to be better as human beings and as husband and husband and wife and we’re always questioning things. And I think that’s important for anybody, whether you’re in business with your spouse or by yourself. Like it’s important to question things and how can they get better, how can you continue to move forward? And that’s something that I really feel proud of in the, in what we’ve built.


Leah Gervais: Yeah. 100%. And I think that that, you know, really comes through. So, okay, so you guys, you know, you work through a ton of mindset stuff. Like I very clearly remember this and we could do a whole episode on that, but like you guys really shift into this idea that like we met in LA, we have lived in LA, you know, James has this job that he likes and is not going to be easy to say no to. Um, we’re going to give that all up. We’re going to move our apartment or get rid of our apartment. James is going to quit his job, we’re going to move. And yeah, I remember Anna was like in my mastermind during this, so it was incredible to see in real time. And it was like a really great decision for you guys because pretty quickly things started taking off. So will you walk us through kind of like that exciting time? A little bit.


Anna McNaught: Yeah, I remember being on one of the mastermind calls and being like, so I’m kind of over what I’m doing right now teaching Instagram and I kind of want to buy a van and maybe just travel. What do you guys think? I remember like, then from there on out, that was kind of like my goal and it was, it was just like crazy for James and I to start like really making that a reality and being like, okay, let’s take the steps to like start looking on Craigslist and you know, find a company maybe that could build one for us.


James Bonanno: Well, let me back. Let me backup for a quick second because skeptical Jimmy over here, you know, like those-


Leah Gervais: I’m going to only call you that from now on.


James Bonanno: Skeptical Jim. That’s a good one, I like that. Yeah. People should just start calling me skeptical Jim. So, I remember one day I came home from work and like, um, I’d come home from work and be kind of just wiped and Anna would be in her throes of inspiration at like seven o’clock at night and want to go over work in business. And I was always interested, but I didn’t have the mental capacity sometimes to really give it my all. And I remember she had built this vision board, like on an actual poster board during the day where she put, um, you know, she like, it was like fifth grade arts and crafts all over our apartment and she would like cut out, uh, like newspaper articles and like a blank check that said like a million dollar million dollars on it. And there were photos of different vans and I was like, what the F? What is this? What’s going on.


And uh, you know, she had explained to me like how a vision board works and why it’s so beneficial to really manifest what you want and like to see it every day and to say it every day and to like have it clear in your mind that like, this is what I want, this is what I’m going to go after and I’m not going to fail. And it wasn’t until like months later when we left and we had the van and we started making some money that I was like, do you remember that vision board? Like if we looked at that right now, I bet you it would look a lot like what we’re doing right now. Um, and skeptical Jimmy, not so skeptical anymore.


Anna McNaught: Yeah. And then I made you write a vision board list in your journal cause he was not about to do arts and crafts, but he, uh, I remember we like looked at it a couple months later and I was like, you can literally cross almost every single one of these off your vision board list. And it’s like, that was such a, just like, wow, you know,


James Bonanno: One was like, make you know, a five figure a month consistently. And we were like, Oh yeah, cross that off. Like we did that last month and, and we, it was, it was like without the full time job that I had done that, that we had done that together and I’m like, Oh my God, like we’re doing it. We just didn’t, we didn’t realize that we hadn’t quite jumped fully on board. And so I just thought that was funny to like think back on as a tangible, as something tangible that like Anna had done that really helped her to see what her goals were and just like push towards them.


Anna McNaught: And then I think going back to your question of how everything started coming to place, it was like once we were in the van and traveling around like an even, even kind of more like talking about what our plan was on Instagram and Facebook and everywhere. We started having like clients, um, or you know, people who found us on Instagram start reaching out and be like, Oh wow, this is so cool. Like, how can we work together? And then even like reaching out to people we’ve worked with before, like getting referred to other clients and stuff. And it kind of started this whole spider web of people and hearing about what we’re doing and feeling like it was cool and it aligned with like their photography brand goals or whatever. And that was like, really when we started picking up momentum and we’re like, wow, this is actually turning into a legitimate business. 


Leah Gervais: Yeah. Awesome. And so you guys started having those five figure months exclusively from travel related work within a few months after you guys left LA, right? Like it was quick.


James Bonanno: Yeah, we left, we left LA in July-ish. Um, and a lot of like what I, what we had planned on trying to do was, um, retain the clients that we currently had to make sure that they were sort of aware that we now had a little more time on our hands. And also over that last year I think we were really working on like, um, getting as much work and as much content out there and like high quality brand work that we had already done so that people knew. Like clients knew that okay, these guys are good at what they do. They’re the real deal. And trying to just simultaneously do two things at once. Like do you know, move across the country but then also build our portfolio and our website. And I think in like September, October. October was probably the best month and that was only three months, four months after we… math. I hope that’s right.


Leah Gervais:  Oh, awesome. You guys, it’s just incredible. And I don’t even know if they, they are the real deal. I don’t, I think I told you this story, Anna, I know a few years ago, this was like earlier on in our journey you had posted, you had re-posted something on Instagram, like on one of your stories. Um, and long story short, someone saw it who followed you, who lives in New York. And I ended up connecting with him. And the way he talked about your Photoshop skills, he’s just like, I don’t understand. She will take one picture, a totally opposite picture. I don’t even know how she thinks of her vision, but she does. And then all of a sudden it’s like perfectly like, he’s like, I will never understand how she does it. So you’re blowing people away all over the world. 


Anna McNaught: That is so amazing, I love that. 


Leah Gervais: So tell us a little bit about like kind of what you’re, I know no day’s the same, but like kind of what are some of the common types of work you guys do? And I know it’s all travel-related, but for people out there who relate to your guys’s story, like they love the idea of traveling. They love the idea of working while traveling, but they can’t really conceptualize it. Like what does that look like for you guys and where, where could they start?


James Bonanno: You want me to take that off? So I think there’s a lot of different ways in which people can start traveling. Whether they make a little money while they’re traveling or they use it as a place to start and create content and get things for, you know, get a hotel compensated for the exchange of, you know, um, photos or video. I think our biggest clients really come from, um, from brands that are, you know, hotel companies or airlines or like companies that feel like on brand for us too. One of our, one of our, our best, uh, clients that we’ve been working with since last year is, uh, is a current retainer client. So we’ve found ways to maintain a monthly retainer with certain clients so that, that’s sort of, that’s like the consistent income that might be happening every month.


Whether you don’t have a, in a situation like a pandemic, like we’re obviously not flying places right now, so we need to make sure that we’re still balancing that evenly. But I would say the majority of what we’re doing are like brand campaigns through photo, video, Instagram posts, things like that. Because the one thing that we can offer, um, is video services. That’s my profession and photography services as well as the photography element of us in the van and us traveling full time. So we’re sort of using our, we’ve used our situation as a way to like pitch brands and say, look, this is what we’re doing. You can fit in this story perfectly or vice versa. Um, and that seems to be a pretty good message so far. 


Anna McNaught: I would agree with that. And I, I feel like also, you know, especially during this pandemic and everything, like people tend to forget like what they have, um, on hand at home for like photos or you know, brand photos and stuff. And like, if that’s something that they want to get into or maybe they haven’t started, like traveling yet or kind of, they’re like, I don’t, I can’t get any content. I can’t even leave my house. You know, there’s so many ways that you can get creative at home, whether it’s like staging something on your bed or like in a window or, you know, even on the floor with your camera next to you and be like, you know, I’m dreaming of traveling or something. You know, there’s like little ways to kind of get innovative and creative with it. And that’s really what we were doing when we were still in LA and like, you know, couldn’t travel during the week or something. We’d be like, okay, well let’s, you know, stage something on the couch. Like, I remember we did a shoot for um, Dogfish head and we were just sitting on our couch with our beers and we’re like, Oh, we’re so cozy at home, you know? And it was awesome cause we were just like literally in our living rooms.


James Bonanno: Well I think a good example of like ways that we’ve taken advantage of, uh, of one job and like rolled it into other ones. And this is really good advice for people that are currently in a nine to five wanting to travel and they want to get there. So there’s ways to like ease into it a little bit. We had applied to everything under the sun. We had built our website up and we were looking for making a list of like, okay, where do we want to travel? In an ideal world, where are these places we want to go? Um, and Banff was actually one of these places that we were like, Oh my God, I want to go to Banff so bad. I want to see Lake Louise and Moraine Lake and all these places. And so I just started kind of drafting a pitch email on who we were and had the website and the content to show for, for what we had done.


And I remember sending this email and like hours later they responded and said that they had been building this program called the creator house program, um, where they would bring creators like ourselves out to kind of tell the story of their experience over a few days. And then with that, you have all of these awesome things like we went dog sledding, we were in a helicopter, we got to go skiing. And in doing a trip like that, um, even if it’s not for a lot of money or if it’s free, you’re putting yourself in a position to create content that is building your portfolio. So then you’re pitching the next client on what you’ve already done. And so there’s ways to like take work for less money or free if you have the stability to cover it. And that goes such a long way and like building a portfolio so that down the line you can, you know, get paid for it. 


Anna McNaught: Definitely. And I, I think like the interesting thing with that was that we did the Banff trip with this company as well as um, a trip to Winnipeg and that’s actually like our highest watched video on YouTube right now, which has brought in like a ton of subscribers for us. And then now because we’ve had like such a great time working with them and they like us and our content, um, now they’re starting to put us on like more paid jobs cause now they see like what we’re offering in the quality and like literally those two jobs that we did in Canada like launched so many other paying gigs because like Jane said, they saw our content, you know?


Leah Gervais: Yeah. You guys are very smart about, you know, having, it kind of goes back to your natural skills, like having the mix of having that security in your business but then also thinking creatively about different opportunities and how they could feed into something in a bigger picture. And just you were making me laugh, Anna, about your ideas to like have creative content at home. Because Anne and James helped me with a Stella partnership in my New York City apartment with our mini Christmas tree. We did a whole photo shoot. It was great. It’s totally possible. But what I think you guys have done so well, and this is like something I really, really drill on in my mastermind, but I don’t think many travel focused entrepreneurs do it, is you have let go of the label around we’re travel Instagrammers, we’re travel bloggers, we’re travel creators even or Youtuber’s or whatever. 


Like you guys have such a clear mission. Going back to what James was saying, closer to the beginning of travel as a vehicle for good for social change, for you know, connection. And you have just been able to really cross that through a variety of platforms and therefore a variety of income streams, which is so smart. And I think people get very bogged down in like, well what am I? And what am I doing? And you know, what kind of thing am I creating and how do I make money? And it might feel a bit more secure to think about that at first. But that’s a false security because if you can really think of your mission, you actually have so much more flexibility to, you know, to cross pollinated occur in different ways. And I think that that’s another reason why you guys are in such a good position in the midst of this economic, I don’t even want to say collapse because I don’t believe the economy is collapsing, I think it’s shifting and we’re just at a low point. I know, um, you know, and so it’s just amazing that you guys have kind of set herself up in a way where, because your mission is so clear and you guys know your community and you know what you want, that is so resilient. And I think that that’s why you guys are such good people to learn from. If you, if people do want to become a travel entrepreneur or get better at it. 


Anna McNaught & James Bonanno: Thank you.


Leah Gervais: Yeah, definitely.


James Bonanno: Man, Leah’s just throwing all the compliments out today. 


Anna McNaught: I know.


Leah Gervais: I love you guys so much. I mean, it’s no secret. 


Anna McNaught: We love you too.


Leah Gervais: You guys are like my favorite. Just, you know, such a good example of what it means to, um, have a network as an entrepreneur and not feel like you have to do this alone. And for those of you that don’t know, like Nina and his friendship very well, we met on social media years ago when she was living in LA and I was in New York and our then blogs were like in their infancy and you know, she ended up joining my mastermind and her and came to my wedding a few months ago. And it’s just like so incredible to think of that chain of reaction in events and that’s, you know, the kind of community you guys create too. And I know that you guys really value the relationships that you’ve created. So yeah, I actually can’t run out of good things to say.


Anna McNaught: It’s such, it’s such a crazy journey like with our friendship and everything. Like I love telling people about how awesome it is. I’m like this random girl I met on social media has become like my best friend, my mentor, my coach, like everything. It just, it’s so cool. What world we live in on binders. Just like wow. 


James Bonanno: It’s amazing.

Leah Gervais: Yeah, it’s been incredible. So what would you guys say are the three, like if you could think of three things that have really contributed to your success in building this travel business, what would they be and how can people start thinking about those resources for themselves?


James Bonanno: Ooh, um, well I guess I might think of them more in like a general, um, like theme or an idea rather than like a tangible thing you could do because I think all of those tangible steps come from like what you believe in up here. And I think the first thing that you would need to have or you want to have is passion and that passion comes from, it doesn’t have to be travel, it could be whatever else you’re passionate about that you want to go and pursue instead of what you’re doing now. But I think passion is like number one on the list of everything else falls under that because it’ll just, it’ll happen naturally if you’re passionate about something 


Anna McNaught: And that will drive your goals. 


James Bonanno: That was my second. Did you just read my mind?


Leah Gervais: Are you guys together 24/7 or something because I’m starting to get that sense.


Anna McNaught: We’ve only seen each other pretty much.


James Bonanno: Yeah. Thank God for Zoom or else we’d have only seen our faces, so it’s nice to see like- I love this, I love this woman. But drive is the second piece that I was going to say is passion and then you know, it leads to the drive and the motivation behind it to really like pursue what you’re passionate about. And I think that drive then like funnels into everything else that you do. Um, and because you’re so passionate about something, you’re just like way more inclined to want to work all hours of the day or night work to find this dream and to do everything you can to get there and I guess the third piece, I’m doing this on the fly. 


Leah Gervais: I did not prepare them for this.


James Bonanno: Well, the third piece I was going to say is like execution. Maybe that’s similar to drive and motivation, but I think you can have one and not the other. I think you have to have the passion to want to do what you’re doing and travel, the drive to really like push for it, and then you have to execute. You have to be willing to actually like take the steps necessary to get there and do it. Um, put the work in, like build the website, the content, have the really shitty client meetings that don’t work out, get a lot of no’s, fail a ton of times, get more no’s, you know, like have struggles and break through them. And that’s the execution part that I think people sometimes, um, like get scared of and don’t push through that. 


Anna McNaught: Yeah. Yeah, definitely. And then I would just add one fourth bonus in there. And I think something that we’ve found a lot of success in is, you know, like I mentioned with the Canada stuff like networks and referrals for us have been like so huge and just like, not so much like going out and networking or anything, you know, but really like keeping like positive and upbeat, um, communications with our clients and even through like this pandemic just being like, Hey, how are you guys doing? Like, you know, everyone good there? You know, checking in, even like, um, uh, for, we just worked with Visit Tucson and it was like, it was a free job that we had. Um, just like, you know, hotel and airfare and everything covered. And we were like, well we want to go, cause we know some people and it could be fun to go back there, but one of the things we did was just like write a handwritten card afterwards and we were just like, thank you so much for this wonderful opportunity. Thank you for taking the time to like show us around and everything and little things like that go a long way to help build referrals and continue to get you like lots and lots of paid work.


James Bonanno: Handwritten is an understatement. Anna literally  water color painted the desert. 


Leah Gervais: I could not be less surprised. That’s not a fair piece of advice though, Anna because no one else can do that. So what you’re gonna do is do a personalized canvas and you’ll have-


Anna McNaught: That is why I didn’t mention it. All I said was “handwritten card”.


James Bonanno: To clarify, it’s the, it’s the act of doing it that’s important. 


Anna McNaught: But like the truth is just in like being a real person with your clients and like being down to earth with them and not making it all about like the paycheck, making it about like the human relationship that you have with each other. And that goes such a long way. 


Leah Gervais: Totally. And I think that that goes back to our story too. Like that’s how and why we’ve all come as far as we have together. Um, and I completely agree with you James. And if I were to piggyback off of what you said, I think I would say the execution part is like at least 80% of that equation because passion is necessary. It’s also easy. Everyone has a passion that they could say or dream. It’s easy to have those things. It’s not easy to do them. And I think you guys having like continued to show up, continuing to push yourselves, take risks, do things that what, what, what did you call yourself? Skeptical. Jimmy is skeptical about doing, you did it anyway. And, I mean it’s sad, but it’s true. Like I know having worked with so many entrepreneurs, that’s where Mo, that’s what most people won’t do is like actually do everything that it takes. Um, and then piggybacking off of what Anna said, the networking piece, do you guys kind of want to, I know you believe in that so much and do you guys kind of want to share, you know, the offering that you have that is exactly about that kind of thing?


Anna McNaught: Yeah.

James Bonanno: Yeah. Do you want to do it or do you want me to, I like how we’re still trying to decide who speaks here. Um, okay. Yeah. Um, I guess, are we talking about our program? Um, yeah. So, so going on that, on that piece of networks and referrals and just building a community, one of the things that Anna and I are really passionate about is building our own community of like minded entrepreneurs and creatives that, you know, either want to leave their nine to five job or travel full time, um, with ultimately with the goal of creating a business that, has way more freedom and is a business around what they love as opposed to having to go into an office and sit behind a desk. Um, and life is too short not to take those risks. And like we’ve talked about, we’ve done that where we’re currently in the throws of, uh, growing our business and we really wanted to do that and teach others to do the same. So we’re currently kind of in the process of onboarding, like minded individuals. And so far it’s been going really well. And I think it’s opened our mind to just how unique and different people’s mindsets are and what we can offer to, uh, to change some of those things.


Anna McNaught: Yeah. Yeah. We’re really excited because we’re going to be launching our first 90 day mastermind I guess end of April, early May and like we have some people signed up like James said, and it’s just like, it’s so exciting to see everything like coming full circle now and being able to help others follow their dreams and hopefully in as short amount of time as we did. And like something I told you Leah, I remember when I, when we first got in the van, it was like this, I think you texted me and said how’s everything going? And I said, I feel so good. Like my heart is quiet right now. It doesn’t have that pull in like a million different directions of feeling unhappy and like going all these different ways. And like when I felt that feeling of like everything just feels like so still inside my own body, I was like, wow, I want to be able to share this with other people because it’s like it’s an incredible feeling. 


Leah Gervais: What a beautiful visual and great representation. 


James Bonanno: Well said.


Leah Gervais: Very well said. We did not practice this. You guys, I think that that’s, that’s so relatable for whatever version, you know, that feeling is for everyone. Cause I think it will be different, but I think everyone can relate, especially if you’re an entrepreneur, feeling that perpetually behind-ness or like being pulled to do a million different things and that you guys found like your flow and that you can now teach others. That is, is just incredible. So thank you guys for sharing your story. Anna, I want to ask you one last question because I know you did my mastermind like near this time last year and um, we open it again. So I would just love it if you’d be willing to share any feedback on the program. And James, you can feel free to chime in because I know that you went through the thick of it with Anna. If there’s any like anything-


James Bonanno: I did.


Leah Gervais: you were like our other member, you guys and Lucy, she was a big part of it too (their cat).

James Bonanno: I was the silent partner.


Leah Gervais: Probably at first just being like, what is this woman telling my wife today? But yeah, if there’s anything in addition you want to share, appreciate it. 


Anna McNaught: Yeah, for sure. So it’s funny because I remember like when you first told me about the program, it was during that time after our wedding where I was just feeling really down and everything and I, I realized that something like that could truly help me. And I remember when I first told James, he was like, what? Why? Like why are you going to spend like money to be educated about this stuff? And like, you know, just kind of like, what is the point of like a mastermind? Like he didn’t really understand. And, um, you know, of course he knew my relationship with you and knew the value that I’d gotten from you and your past in the past and the other programs you had. But I was trying to express it to him and he’s like, okay, well you know, whatever, it’s your business like you do whatever you want to do.


And I was like, okay, well I think I just feel in my gut that this is something that will be really helpful for me and Leah has never steered me wrong in the past. And so I want to give it a go. Like why not? Worst thing is I lose some money. Like it’s not the end of the world. Like I’ll learn something and I remember like the first month in the first or second month into the mastermind, like not only had I already like just learned so much about like myself and who I am, but I had my first five figure month, which was like so incredible, like such an awesome feeling to be like, wow, I can do this. Like everything that Leah has said as like, you know, it’s starting to happen. And, and then just like also the other women in the group and like, and they’d become, you know, some of my closest friends as well. And like, we all had just such a strong connection with each other. And I think learning from each other, learning from you, Leah and like, you know, really pushing through those boundaries that were so visible for me like early on in 2019. Um, and like I said at the beginning of this podcast, like talking about, you know, getting through my mindset and like getting rid of the self doubt and the money boundaries that I had on myself and like I came out of the program just feeling like I finally have clarity and I finally can like, listen to my heart and my gut and like I said, you know, not have to look at all these other things. Not have to keep buying courses. I can unsubscribe from literally everyone’s email, you know. I don’t need to read this crap anymore. I don’t need to watch a million webinars like I’ve learned what I need and what I needed was just like to trust myself and trust my instinct. And I can’t thank you enough for that because if it wasn’t for your mastermind I would probably still be maybe in LA, maybe still, you know, watching webinars and probably just crying every day.


Leah Gervais: Thank you Anna. That’s so amazing.


James Bonanno: Well, yeah, I can, I guess I can kind of uh, agree with that with all of what you said because I saw the transformation happening like in real time, like the whole, the whole time man, I was in your mastermind, I was working full time and I’d come home and there’d be nights when I think like going back to what we said earlier, you know, uh, holding people accountable and like questioning things that are often hard to swallow are often hard to question. I think one of the things that at least I took away through Anna was that you posed questions to people and you created situations that no one really thinks about that had transformed the way Anna viewed her business. And then ultimately our business. And, um, you’re a direct product of how I think we’ve built our business and the mindset in which like I’ve gone into business and we’ll continue to do so. So I think everything that Anna said is true. And, um, you know, I’m very appreciative that she was able to do this program with you and skeptical. Jimmy was skeptical Jimmy no more.


Anna McNaught: And like every time I’m working on something, I feel like I’m always like, tap into Leah. Like, okay, what would Leah tell me to do right now? And then I imagine your voice being like, okay, here’s exactly-


Leah Gervais: Oh my God, thank you for that. I have another like, uh, one client who’s in my mastermind right now and I had her do this exercise like this year projection thing and I don’t exactly remember how the conversation went, but something like, she’s like, yeah, my husband came home and I showed him this and he’s like, I’ve been trying to get you to do this for years. That’s what you should do. And you just did it. I think maybe sometimes it’s like it needs to come from like within or just you know, a different place than like your relationship or whatever. So anyway, it was a complete joy watching, you know, you do that. And thank you so much for sharing that. That obviously is like why I, you know, do this business and it moves me every time I hear you guys talk about her experience there and uh, I am honored to be part of your journey. You guys know how much I believe in you and how awesome I think you guys are at what you do and how many people you’re going to help. So thank you for sharing that experience. 


Thank you for sharing your story. Thank you guys for doing what you did. And I just, you know, I hope that you really sink into how many lives you’ve already changed just by doing this and just by, by showing that you can be brave, you can live a life that lights you up. And even though it doesn’t always look pretty, and even though you don’t always know what the next step is, you can be stronger than you realize and figure it out. And I think that just by you guys doing that, you’ve given so many other people permission to do the same thing. So thanks for sharing your story and yeah, you guys are the best. 


Anna McNaught: Thank you for having us. And thanks so much for the compliments. It really means a lot to us. 


Leah Gervais: Oh my God. Anytime. All right. Visionary as well. Go check Gow Anna and James on @Leavethemap on Instagram. Reach out to them. They’re like the most down to earth chill people ever. And if you just want to talk about, you know, how you can start with a brand partnership or how you can get better on social media or what could be possible for you, reach out to them, check out their stuff. And if you have any questions for us, you can reach out and we are all three cheering for your biggest vision. Talk to you guys soon.

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