Moving To Argentina With Only 5 Grand Changed Gareth Leonard’s Life | Drop A Pin Ep. 98

Drop A Pin

Gareth Leonard, a content creator known for deep travel experiences, shares how moving to Argentina with just $5,000 transformed his life an

Key takeaways

• Moving to Argentina with minimal funds allowed Gareth to live authentically and build a sustainable travel-based livelihood.
• Traveling deeper means engaging with local culture, not just sightseeing—especially in places like Buenos Aires where nightlife and street life reveal hidden layers of society.

Main topics

• Living abroad with minimal resources
• Cultural immersion through local experiences

Notable quotes

"Never ask for permission. That's exactly right."

Conclusion

Gareth Leonard's story illustrates how stepping outside comfort zones—whether financially or

Transcript preview

Speaker 4 (0:00) Hey, Barstool listeners, you can find every episode of this show on Apple Podcasts, Spotify, or YouTube. Speaker 5 (0:05) Prime members can listen ad-free on Amazon Music. Speaker 2 (0:08) Tired of nicks, cuts, and bumps? It's time to ditch the blade. Nair, the award-winning number one hair removal brand, gives you silky, smooth skin in as little as three minutes. That smooth that lasts for days longer than shaving. Easy to use, blade-free. Dermatologist tested and made for all skin types. Plus discover our new sensational fragrances that turn hair removal into a whole vibe. Shave less, glow more. Find Nair at all major retailers. Speaker 1 (0:39) Hey, how are you? At Boar's Head, we've been going back to school for over 115 years. And this year, every school lunch is reason to celebrate with the flavors your kids love and the exceptional quality. you expect. Helping you make school lunch fresh, easy, and delicious. Ring the bell. The deli is open. Speaker 1 (1:06) Boar's Head. Committed to craft since 1905. Speaker 3 (1:10) Today on Drop a Pin, we talk to content creator Gareth Leonard, who teaches us how to travel deeper and how to make a living doing it. Did you ever have to get a job down in Argentina? I was a Speaker 5 (1:20) bartender. Speaker 4 (1:20) All Speaker 3 (1:21) right. Speaker 5 (1:21) I was playing basketball with the son of a small microbrewery. And right in Recoleta, like right next to the famous cemetery. Speaker 3 (1:32) And Speaker 5 (1:33) so a lot of people in there was also some... Putarias around there. Some like establishments of the night. Speaker 3 (1:42) Puta means like a whore or like a bitch. So like a putaria, a place that sells whores. Yeah, like a Speaker 4 (1:49) bitch factory. A bitch factory. That's a great translation. Speaker 4 (1:56) All right, Donnie, for today's top five, I want you to go back to your home state. What are the top five most populated cities in Massachusetts? Speaker 3 (2:05) Oh, I like this one. All right, so number one, Boston. Boston Speaker 4 (2:08) has a population of 672,000 people. Speaker 3 (2:12) Okay, another one is going to be Worcester. That Speaker 4 (2:15) has a population of 213,000, and it's number two on the list. Welcome to Speaker 3 (2:19) Worcester, $1.25. Speaker 3 (2:23) Watch the skit Tollbooth Willie if you haven't. It's an old Adam Sandler skit. Springfield. Speaker 4 (2:28) Springfield is number three. You're going in order with 154,000 people in Springfield. Speaker 3 (2:35) No, it's going to get a little tough. I mean, does a town count too? Does the town of Plymouth count? Speaker 4 (2:42) Plymouth is not in the top ten. Speaker 3 (2:44) It's a huge land area. All right, so now give me Quincy. Speaker 4 (2:50) Quincy is number eight on the list with 103,000. Oh, what about Lowell? Lowell is number five with 119, so you're just missing number four. Speaker 3 (3:00) Okay, shout out Lowell, old mill town. And then number four, Attleboro. Speaker 4 (3:11) It sounds like an old college town. Amherst. No. Dartmouth. No. No way. That would maybe even be in England. Speaker 3 (3:22) Oh. Cambridge. Speaker 4 (3:24) Cambridge is number four with 122,000. The top 10 would end up being Broxton, Lynn, Quincy, New Bedford, and... Fall River rounds out the top 10 with only 95,000 people. Speaker 3 (3:39) I think Fights is from around Fall River. Yeah, he is. Yeah, it's known for being very rough around the edges. They kind of had a bit of a pill problem down there. But it's a beautiful area. Yeah. Speaker 4 (3:48) And Speaker 3 (3:48) they got a lot of Portuguese. That's a fun fact. Final Speaker 4 (3:52) Bird's been known to do a pill or two. Yes. Speaker 3 (3:55) Is it the Portuguese or the Cape Verdeans that are all down there? I think maybe both. Who knows? Speaker 4 (3:59) Oh, I think you're thinking of... Speaker 3 (4:01) Rhode Island? Rhode Island. Speaker 4 (4:03) Providence is where. Because that's the only. Speaker 3 (4:04) The Speaker 4 (4:04) Cape Verdeans are? Yeah, that's the only direct flight in the United States. The Cape Verde is from Providence to their capital city. Speaker 3 (4:12) Yep. We should do that sometime. I want to Speaker 4 (4:14) do that flight. Speaker 3 (4:17) I mean, we should. It looks like we can find enough things to do in Cape Verde. Oh, Speaker 4 (4:22) yeah. We'd love that. Yeah. All right. Let's hop back in the pod. Speaker 3 (4:27) Okay, very excited for this podcast. I wasn't super familiar with Gareth Leonard's content. I'd probably just seen like four or five of his Instagram reels. But then we heard he was going to be in Chicago. And I would honestly say it could be one of the top five conversations we've had on the pod. Yeah, Speaker 4 (4:45) he was an interesting guy for sure. Speaker 3 (4:47) And yeah, I felt like we could have just talked to him for like another hour or two. Another two hours. Speaker 4 (4:53) not gotten bored. Yeah, I went home and watched a couple of his videos. They're all really interesting. He does a great job. Speaker 3 (4:59) Yeah, very funny too. But before we get into the pod, a little bit of housekeeping. We just dropped our first Geo Grand Prix. Great job with that, chaps. Speaker 4 (5:08) Thanks. Good job, Sam, doing the edits and everything. Crushed that. And shout out to the Pinheads for supporting. You guys showed out. We're very happy with how the video performed. There's going to be a lot more of those coming. Speaker 3 (5:23) Yeah, we're going to try to make it a monthly thing. The prize of this first one was going on a day trip with us, obviously KB1. So he'll be doing a day trip with us to Montreal. So if you've got any Montreal tips or you're from Montreal, hit us up. I don't know if the prize every month is going to be a day trip unless we get a sponsor that wants to fund that. Speaker 4 (5:45) Yeah, and if you're a sponsor listening. Yeah. I mean, Blue Chew, I'd fuck KB. Speaker 4 (5:53) We could. Speaker 3 (5:56) Yeah. I mean, yeah, we are probably all going to be sharing a hotel room if we're there for the night. Yeah. Because in terms of flights, you might have to like like leave Chicago at 7 a.m. and then leave Montreal at 6 a.m. the following morning. So we either sleep in the airport or we all share one hotel room. I Speaker 4 (6:13) want to sleep in the airport. Speaker 3 (6:15) Yes. And I feel like. I mean, I might join you there, but like KB won this. And so I feel like as a prize being like, and by the way, you now have to sleep in an airport. Do you think, do you think the airport would let us like pop a tent? Speaker 3 (6:30) Definitely, I think, inflate a small little aerobed tent. I don't know. We could try. We could try. You always got to ask for forgiveness. Never Speaker 4 (6:39) ask for permission. That's exactly right. That's Speaker 3 (6:41) probably one of my biggest travel hacks. Yeah, that's a huge one. Never ask Speaker 4 (6:44) for permission. I mean, when we went, Mia, I think you weren't there. It was a San Francisco trip, I think. Might have been Vegas, but I brought a little blow-up mattress in my backpack just in case we were there for a long time. Slept like a baby in there. Threw in some earplugs and put my eye mask on and had the little sleeper mattress in my backpack that I blew up. Speaker 3 (7:06) Which airport was this? I think it was Speaker 4 (7:08) in, was it San Francisco or? Portland, yeah. One of the West Coast ones where we didn't fly back until like 1 o'clock in the morning. Oh, okay. And so we got to the airport, back to the airport at like 8 or 9 or something like that. And I just slept on the floor for like three hours. Speaker 3 (7:23) That sounds way better than I sometimes try to sleep on this, just like the airport seats. They've got like three in a row, but there's kind of like a little gap in between them all. Yeah. It really messes up your back. Speaker 4 (7:33) Yeah. If you can find a nice little spot with no benches, that's out of the way, having one of those little things and then just putting a hoodie over your head or something like that. Loved it. That's awesome. Speaker 3 (7:43) Well, if we don't find a sponsor, I guess we could just make the prize every month a day trip to, like, Milwaukee. Because that would be cheap, and we just keep on going to Milwaukee. Speaker 4 (7:54) But Speaker 3 (7:54) I've honestly lived in Chicago over three years, never been to Milwaukee. I haven't either. Really? Okay. Let's do the train. Speaker 4 (8:02) Yeah, it's a quick little, like, hour and a half Amtrak or Speaker 3 (8:05) something. Yeah, do Speaker 4 (8:05) that. Have some train beers. Speaker 3 (8:09) Yeah. All right. I'm game. I hear it's nice. It's probably nicer now than it will be in the middle of the winter. Speaker 4 (8:15) Let's do it one Friday. We can find a Brewers game to go to. Speaker 3 (8:19) Oh, yeah. Are they going to be in the playoffs? I, like, have not been. Speaker 4 (8:22) Yeah. They're in first place, I think. Speaker 5 (8:24) Okay. Speaker 3 (8:25) Let's go. Shout out to Brewers. Yeah. Shout out to Brewers. I have not really. We're not Speaker 4 (8:30) baseball guys. I'm a big. Speaker 3 (8:31) I'm a playoff poly when it comes to baseball for sure. Speaker 3 (8:35) But yeah, without further ado, let's get into this pod. We talk about some more interesting places than Milwaukee. Argentina. We can't say that. We've never been. Yeah, that was a little rude of me just to throw Milwaukee under the bus right before we get into this pod. But Gareth Leonard's been all over. He lived in South America for many, many years. So we talk a lot about South America. We really just hop around the globe. Yeah, let's do it. Speaker 3 (9:07) This episode of Drop a Pin is brought to you by Shady Rays. Quick question for the pinheads. 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Head to ShadyRays.com and use code PIN for 50 % off two or more polarized sunglasses. Try for yourself the shades rated five stars by over 300,000 people. Speaker 4 (10:17) Today's show is also brought to you by the best candy in the world, which is Reese's, the peanut butter cups, the take fives, the nutrageuses. No matter what, if it's got the Reese's logo on it, you know it is. quality candy. It's the superior candy. It's the official candy partner of Barstool Sports. It's what's overflowing out of my backpack to go on me and Donnie's little road trip with Kate and Danny Conrad up to Camp Barstool this week. You can't do a five-hour road trip without shoving Reese's right down your gullet and enjoying every damn minute of it. Speaker 3 (10:51) Yeah, we're going to be on that road trip when you listen to this podcast. So just think of us. eating the most delicious Reese's you can think of. Oh, Speaker 4 (10:58) yeah, that's going to get them going, too. Yep. Without a doubt. Reese's is the official candy partner of Barstool Sports. Go get Reese's wherever you shop. Speaker 5 (11:08) So we did the whole VC, chasing money, that kind of thing. And I was based in San Diego. And I was like, all right, if I get the chance to go back, I'm going to take it. And I wanted a home base. And right before the pandemic, I'm like, I'm going to move to San Diego, set up shop there, and go from there. And it was the best thing I could have done. Speaker 3 (11:25) I mean, San Diego's. Hard Speaker 4 (11:27) to beat. Yeah. Speaker 3 (11:28) It's Speaker 1 (11:28) unreal. Speaker 3 (11:29) And Speaker 5 (11:29) being, I'm from upstate New York. Especially Speaker 4 (11:31) if you're not wearing like a Marine uniform. It's real great. Speaker 5 (11:33) Yeah. Yeah, were you based there? I mean, Speaker 4 (11:38) I did a lot of like pre-deployment training there. Speaker 5 (11:42) Whereabouts were you? Coronado? Yeah. Speaker 4 (11:45) Coronado and just regular Camp Pendleton. Speaker 3 (11:47) The weather sure beats Rochester, New York, which is, that's the area that you're from? Yeah. Yeah, I'm up Speaker 5 (11:52) by Buffalo, Rochester, so yeah, home base. Okay. But man. Yeah, it's an entire Speaker 4 (11:57) parallel universe. I spent a couple weeks in Tonawanda. Speaker 5 (12:02) That's way too much time. That's way too much time to be in Tonawanda. Speaker 4 (12:06) What the hell were you doing there? That's a wild poll. Construction. Got hired when I was in college. They needed people to go up for like six weeks and help put a roof on this church. And I was like, I'll go. They paid us like 500 bucks a week. Not worth it at all. What time of year was it? It was summer. Summertime? Yeah. Okay. Speaker 3 (12:28) You were trying to earn some Jesus points? Speaker 4 (12:31) Yeah, I was trying to earn some Jesus points. Speaker 3 (12:32) You go Speaker 5 (12:32) to Tonawanda, man, and you don't often get out, so good for you. Yeah, I love it. When somebody says Buffalo, Rochester, Speaker 4 (12:37) I always throw out Tonawanda, and everybody's reaction is always like, ugh, God, Speaker 5 (12:40) why? We actually, the last time I met someone from Tonawanda, we were in Vegas, a buddy's bachelor party, and we went to the Hooters Casino just because we wanted to go low-class craps tables. Uh-huh. We go there. Our main craps dealer, whatever you call the guy, not pit boss, but the guy who's calling the shots. From Tonawanda, we found out he proceeds to get blackout drunk as we're playing. The pit boss had to come over and pull him off. And we're like, this is Tonawanda in a nutshell. The guy who's working at Hooters in Vegas. He's doing Speaker 4 (13:15) the culture of his people. Yeah, it's too much. It was too Speaker 5 (13:18) much even for Vegas Hooters. They're like, sorry, man. Tonawanda is too heavy here. That's the spot. Speaker 3 (13:26) I'm just going to drop a clap. Speaker 3 (13:30) Okay, today on Drop a Pin, we got Gareth Leonard. He's the dude behind the Instagram page Travel Deeper and the YouTube page Gareth Leonard, which is almost around 800k subs. Congrats on that. Thank Speaker 5 (13:41) you. Thank you. Speaker 3 (13:42) I was trying to pinpoint when I started first following you and I was looking back at your reels. It was the reel about the lobster capital of Mexico. Oh, Speaker 5 (13:50) yeah. Because I love lobster. Ortega's, yeah. Love Speaker 3 (13:53) Mexico. You're a very charismatic guy. I appreciate that. I got to Speaker 5 (13:57) watch this. That was Speaker 3 (13:58) a great little clip, and that's kind of got me into your content. Very cool. But you've been in the travel content game for a long time. Speaker 5 (14:05) A long time. Started in 2009 with a travel blog. Speaker 3 (14:09) And that Speaker 5 (14:10) was like me and 10 other guys had a travel blog, and it was all just best things to do in, top things to do in. And so my first thought was, all right, I'm going to try to do this a completely different way. And so I started a blog, which... terribly named. It was called Tourist to Townie. And Tourist to Townie was like the idea of, I'm a terrible traveler. So like by fault, people are like, oh, I've been to a hundred countries. I've been to all of these places and I'm terrible. I'm like 50 countries deep, but I spend a lot of time in one place. And so the idea was like Tourist to Townie. I was going to go live in Argentina for one year only. And I was just going to try to go from a tourist to a townie. And the funny aspect of that is. So the first time that name, I was like, oh, Tourist Atownee, it's like this, you know. And from the States, you know, Atownee is like the guy who's got a seat at the bar. He's a regular Speaker 3 (14:59) dude. But Speaker 5 (14:59) in the UK and other places around the world, Atownee is like. white trash? Speaker 3 (15:05) Yeah. So, yeah, I mean, it's kind of like, it kind of means white trash up in Boston too. Like when I started making vids in China, the whole premise was I was a Boston townie that blacked Speaker 5 (15:15) out Speaker 3 (15:15) at Logan airport and woke up in China. So that like that whole Speaker 5 (15:19) shtick of like tourist Speaker 3 (15:21) townie Speaker 5 (15:21) just immediately did not hit the global audience. Okay. But yeah, the goal was to live in Argentina for one year. Get a local job, local girlfriend, local friends, local roommates, all that kind of stuff, and trying to just live that foreign life. Because I'm from a tiny town in upstate New York, a suburb of a suburb of Rochester, New York, up by Buffalo. And it was like I just wanted to experience something unique to anything that I've known. started this journey. Yeah, it was crazy. Speaker 3 (15:49) And you were blogging because that was like before there were a lot of big travel YouTubers, right? No YouTube whatsoever. I mean, it was like the first Speaker 5 (15:56) videos were coming out right 2006 about the first videos from like the San Diego Zoo. Yeah, or it'd be Speaker 3 (16:02) like family guy clips. I remember that was like the first YouTube video I watched. It Speaker 5 (16:07) was random clips. Chocolate Speaker 3 (16:08) rain. Yeah. You Speaker 5 (16:10) can always remember like your first YouTube experience. And so it was that. And also, At that point, blogs were the only thing being monetized too. So I was like, all right, I can maybe sell some text links, some banner ads, things like that, and I can make a run at this financially too. Because I left home with $5,000 in my bank account. I was like, all right, I'm going to make this work. Sink or swim, I have to find a way to make five grand work for a year. in Argentina. And I liked, it wasn't after until like a year and a half that I started getting, I started doing like affiliate stuff with local tour companies in Argentina. Cause I'm Speaker 4 (16:48) like Speaker 5 (16:48) my, like the, the positioning was like all the things to do in Buenos Aires. And so then with that, it came some additional income, but nothing to, you know, that monetize like YouTube and that kind of stuff does now. Did Speaker 3 (17:02) you ever have to get a job down in Argentina? I was a Speaker 5 (17:05) bartender. Speaker 3 (17:06) I Speaker 5 (17:06) was playing basketball with the son of a small microbrewery right in Recoleta, right next to the famous cemetery. There was also some putterias around there, some establishments of the night. Speaker 3 (17:27) Puta means a whore or a bitch, so a putteria, a place that sells. Whores? Yeah, like a bitch factory. A bitch factory. That's a great translation. Speaker 5 (17:39) So that was kind of where they all were. And so a lot of American tourists would come in, so they hired me. But I spoke zero Spanish at that time. So I got hired because I was friends with the guy who played basketball with his dad. And he was basically like, you work tomorrow? I'm just like, I start work tomorrow. And I was working there five nights a week. making like 30 to 50 bucks a night. But I was working from like 3 p.m. to like 2 in the morning. So I'd go in early so I could get the family meal because also they did pizzas and things like that. And so I'd go in early enough to get the family meal and then I would just stay for the whole night because I had no other money to do anything else. And I spoke zero, so nobody there spoke English. So it was like the owner. and myself and he literally fired me three times but i never understood so i just kept coming back and by the end of it i became like the bar manager and still was really struggling to learn the language for the first few months i mean Speaker 3 (18:37) that's the reason why hank who works here he's uh very successful at barstool he was fired like twice and he kept on showing up he Speaker 5 (18:44) just keeps showing up Speaker 3 (18:44) yeah that's the way to do it yeah I mean, now would you say you're like somewhat fluent in Spanish? Speaker 5 (18:50) Now my Spanish is pretty good. A little bit less now. I had traveled through the first five years I was through Latin America. I lived a year in Argentina, six months in Colombia, six months Guatemala, five months Bolivia, and then I moved to Brazil. And the goal was to work at the World Cup in 2014. Oh, yeah. And so I ended up getting a job at the World Cup and started learning some Portuguese. So Spanish is, at one point, Pretty good, and Portuguese got good at one point as well. Yeah, that Speaker 4 (19:19) one was in Brazil, wasn't it? Speaker 5 (19:20) Yeah, that 2014. That was France's year, and Germany just destroyed Brazil. I was on the beach in Copacabana, and Brazil and Germany played 7-1. I don't know if you guys remember that match. Speaker 3 (19:34) I do, Speaker 5 (19:34) yeah. pounded them. Speaker 3 (19:36) There's always so much drama leading up to the World Cups. For the Brazil one, I remember they were like, Brazil's way too corrupt to host the World Cup. What are they going to do with all the stadiums they built? Once the tournament started, it seemed like everybody had a blast down there. Speaker 5 (19:49) It was my first gig. This kind of opened the world to this whole world of travel. My first real paid gig was with the Tourism Board of Brazil. And they paid me $13,000 to visit 13 of the host cities around the country. That's Speaker 3 (20:07) great. Speaker 4 (20:08) That's a Speaker 3 (20:09) dream game. I paid for Speaker 5 (20:10) all my hotels, all my flights, all my own food. But the idea was to visit all of them and start their blog on their tourism board website. And so I traveled all 13 cities that the World Cup was in and made a blog and took photos. And I thought, This is where I should start making videos. Speaker 3 (20:29) Because Speaker 5 (20:30) I was like, I'm having all this stuff, getting it paid for essentially. I better film while I'm writing these blogs. And that became my first series is Travel Deeper Brazil. And it was all these different cities, which, you know, the Curitibas, the Porto Alegres, the places you would never go as a regular traveler. So I got to really travel deeper. That became the mantra. Speaker 3 (20:50) Now, did you see success on YouTube right off the bat? The first Speaker 5 (20:54) viral hit? was a play on that Pharrell's Happy. Speaker 1 (21:00) Do Speaker 5 (21:01) you remember that? It was like the trending audio before trending audios. Speaker 3 (21:06) Yes. Speaker 5 (21:07) And so they allowed it for whatever time. And that was my, I did Rio Carnival to Happy's, Pharrell's Happy. Speaker 3 (21:16) Okay. Speaker 5 (21:17) And it got like 300,000 clicks. But at that point, there was no monetization. True. So Speaker 3 (21:23) I Speaker 5 (21:23) was like, oh, that was cool. Now what? And then so that became the progress forward. But at that point when you're young and dumb, views are just all that matters. Views Speaker 4 (21:34) was the currency. Speaker 5 (21:34) Yeah, views was like, dude, I got this many views. That's all that matters. Speaker 3 (21:38) Yeah, that's like a mind-blowing amount of views when you first start off on YouTube. So Speaker 5 (21:42) that Speaker 3 (21:42) was Speaker 5 (21:42) my big hit. So thanks to Pharrell. It was the trending audio. Speaker 3 (21:47) And did that hit kind of give you... the confidence to like vlog more and you're like, maybe I can eventually somehow turn this into a career? Speaker 5 (21:54) Yeah, it was still a balance because the blog was still, you know, bringing in the money through all the different, you know, ways that those used to be, you know, before all like AI chats and things like that. It was still selling guides and all those kinds of things and clickable links and everything like that. But then the passion was in video. Because the video, I knew I could see it. I could tell a better story that way. I didn't love writing, but I knew that was a way to document, right? But once they started video, I could really give people that feeling of what it's like to be in a place. And it's to go back to like the first idea of all of this is most of my friends have never left the country. Speaker 3 (22:36) Most Speaker 5 (22:36) of my guys from back home, it's like, you know, they take their vacation to Florida. And that's... you know, fine, you know, right. People don't always have the Speaker 3 (22:44) luxury to do that. Yeah. Speaker 5 (22:45) But I wanted to show people a different world. And you guys do this all the time. Like when you guys like name a place or like geography quizzes that you guys do on, on, on your, your shore form. It's like, you see what the reality is for a lot of Americans and it's just not built into our culture. Speaker 4 (23:01) No, it's really interesting talking to other people too, like from different countries when you go there about like Americans traveling abroad, like in how, The amount of cultures that you can experience inside the United States is significant. The difference between how you grew up outside of Rochester and how I grew up outside of Jacksonville, Florida is two totally different