Amazing Nomads Podcast: Dan Pierson - Walking Cuba

Travel Adventurer Dan Pierson has achieved what The Proclaimers threatened to do, walk 500 miles - he did it across Cuba.


Photo © Dan Pierson

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What’s In the Episode

00:08 We are world nomads

00:25 Welcome Dan Pierson

00:47 Overcoming fear

01:28 Why Cuba

03:04 Dan’s white lie

05:46 The logistics of walking across Cuba “…I mean, carrying enough food, enough water, I mean a lot of places outside of Havana, Cuba, while everyone has enough, that's something that's obvious. Everyone has enough in Cuba, that doesn't necessarily mean there's enough to share somebody coming to a small town at night and looking for food.”

10:40 Attending a Brazilian wedding

14:42 What is the Bolt Collective

Who Is On the Show

Dan Pierson’s professional background is in the production of events for brands like Airbnb and the Rockefeller Foundation. He's also the creator of Subway Sets, a sold-out concert series bringing New York's best underground musicians up to rooftops above the city. Previously, Dan worked in growth marketing at technology companies Lyft, the Collaborative Fund, and Getable. 

In this episode, Dan talks about facing his fears surrounding adventure “…Yeah, you need to overcome some fear and take that first step.”

Dan's adventures have taken him to more than 50 countries, with stints living in Argentina, the Czech Republic, and Mexico, long bicycle rides across the United States and New Zealand, and a 500-mile walk across the island of Cuba.

Dan is also the founder of the Bolt Collective - “…the basic idea, you bring a community of like-minded explorers together and you use their collective purchasing power, so pool their resources. To unlock travel experiences.”

Photo Supplied: Dan about to cycle 3000 miles through the States

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Explore your boundaries and discover your next adventure with The World Nomads Podcast. Hosted by Podcast Producer Kim Napier and World Nomads Phil Sylvester, each episode will take you around the world with insights into destinations from travelers and experts. They’ll share the latest in travel news, answer your travel questions and fill you in on what World Nomads is up to, including the latest scholarships and guides. The World Nomads Podcast is not your usual travel Podcast. It’s everything for the adventurous, independent traveler. Don’t miss out. Subscribe today.

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Speaker 1: The war nomads podcast bonus episode. Hear amazing nomads sharing their knowledge, stories, and experience of world travel.

Phil: We are world nomads right? We all love the idea of tucking in the day job and hitting the road. But sometimes it's hard to take that first step.

Speaker 3: Yeah, lovely idea. Fear not though, inspiration is at hand. One of our listeners, and we should say hi to Shannon, emailed us about her friend Dan Pierson from the Bolt Collective.

Phil: Dan has visited over 50 countries, but it started with one particularly memorable trip. Three months walking across Cuba. Dan Pierson, welcome.

Dan P.: Hey, thanks so much for having me Phil, I'm thrilled to be with you guys.

Phil: All right look, we'll get to the Cuba trip in a moment. But that's true isn't it, those ... Yeah, you need to overcome some fear and take that first step. What was your first step?

Dan P.: Oh, absolutely. Well, I mean for that Cuba trip it actually started all the way back in San Francisco. So I was working in technology back in 2014 at a great company, great friends, great life, but realized, was kinda just ready for something else. I started taking 30 minute long walks during the day, then the hour-long walks during the day, then two hours long walks during the day and realized I just wanted to be outside all of the time. So, quit my job, two weeks later I was riding a bicycle from Seattle Washington down to the Florida Keys across the United States. With the intention of getting to Florida and finding a boat and if money and motivation allowed, going over to Cuba and doing some exploration.

Phil: Why Cuba? Was that one of your bucket list places?

Dan P.: Sure, you know, I think it holds a special [inaudible 00:01:35]. I'm from the United States, I'm American. I think it holds a special mystique for us, just given all the history. I mean now more than 50 years since the revolution, almost 60 and as someone who has been lucky to travel all over Latin America through Mexico, all the way down to the very southern tip of South America and Patagonia. That was one place I just never had the chance to explore and was so interested in learning more.

Phil: But of course, as an American, at that time it would've been [inaudible 00:02:07] impossible to get there. But that changed whilst you were on your trip, tell me about that?

Dan P.: Exactly, exactly. So, I got down to New Orleans after about 3,000 miles of riding my bicycle and this kinda series of, call it, coincidences, spiritual stuff. In New Orleans, you'd probably call it voodoo, made me realize my bicycle trip was over, and I'd had this pretty huge crisis of identity right. I quit this wonderful job in San Francisco and my whole being was wrapped up in that bicycle trip but realized that trip was over. And through a series of kinda whatever you wanna call them, but however spiritual deep you wanna go, it all culminated in December 17th, 2014. Which was the announcement of the beginnings of the relationship, kinda turning around between the United States and Cuba led by Barack Obama and Raul Castro and brokered by the Pope.

Dan P.: So actually that morning I saw that, remembered 'cause as I've mentioned a bit earlier, that the intention of the trip was actually to go to Cuba in the first place. So, hope the U.S. Government isn't listening, but basically, I printed out a fake itinerary to fly to London. Went down to the U.S. passport office in New Orleans, went up to the window because I needed a new passport expedited, I needed proof, and I needed and explanation of why I needed the passport so quickly. So I told the woman, I said, “You're never gonna believe this crazy story, but was on Bourbon Street a couple nights ago, met a beautiful English girl, and I'm following her back to London.” And I had the ticket to back it up and two days later I had a passport and 10 days after that I was in Havana.

Phil: Nice little lie, as well by the way. I like that one. (laughs)

Dan P.: Yeah, I'd like to call it a white lie. That's one of those white lies, that's what we call it.

Phil: So tell me, your first impressions of Havana?

Dan P.: I mean it's a really spectacular, magical city that I would compare in many ways actually to New Orleans. Which is a place that I lived for so long. There was that kind of almost mystical connection going from New Orleans to Havana. Both have such heavy African influence and were both major slave ports during the time of slavery. And that African influence, it's just everywhere in the music, in the dance, in the art. And it's really, I mean its, I could spend I think 30 years in Cuba and I might just be as turned around as, as when I got there that day because there's just so much, so much to learn and so much to see. So many different perspectives to take into account to really try to get to the bottom of everything that's happened there in the past 60 years.

Phil: So is that part of your motivation for saying, right now I'm gonna see as much of it as I can? I'm gonna walk across the entire country.

Dan P.: Yes, I've been on ... It's funny, I'd been on that bicycle trip, just had this urge to kind of slow down even further. So you can imagine traveling at 7 or 8 miles, or 13 or 14 kilometers an hour and then having just an urge to even slow it down further. And there were some logistics around getting my bike down there. That seemed pretty challenging. And then I actually, I don't know if some of your [inaudible 00:05:22] have seen that movie with Reese Witherspoon called Wilds? But it's about her trek through the Sierra Nevada on the Pacific Crest Trail. But saw that, in the kinda 10 days in between ending my bike tour and starting that walk, and was just like “You know what, I'll just walk.” Which, yeah, turned out to have its own set of unique challenges but also, obviously just so fulfilling.

Phil: What were the challenges?

Dan P.: So, I mean, carrying enough food, enough water, I mean a lot of places outside of Havana, Cuba, while everyone has enough, that's something that's obvious. Everyone has enough in Cuba, that doesn't necessarily mean there's enough to share somebody coming to a small town at night and looking for food. So, always making sure to carry food. I mean, I got caught out without water at one point. I'd been walking along the coast for about 35 miles and pretty much completely empty country. And I ran out of the water, and I was honestly at that point, delirious and there just off in the distance, almost a mirage appeared, and it was this guy on horseback, and he came towards me looking at me like I was absolutely insane.

Dan P.: You know, white guy, kinda sweating profusely with a backpack on. Walking across the middle of Cuba. And he was so gracious he took my water bottle, this massive water bottle and galloped off into the distance, filled it up with ice cold, literally ice chunks, in the most like pure water and brought it back to me. And I mean, pretty much saved my life. A lot of us can identify with what that culture of adventure travel, whether that's something like, bicycle touring, or whether that's bungee jumping, or whether that's whitewater rafting.

Dan P.: Cuba just doesn't really have any of that culture. For a lot of different reasons, I mean, there just isn't really opportunity in a lot of cases to engage in that kind of stuff. Your busy working kinda ... But also the overriding Cuban sentiment is towards this collective social outlook towards, the group or towards the, what you call, like the people themselves. So there's kind of an aversion to risk. Which is where I ended getting into a little bit of trouble. 'Cause there just wasn't particularly on the official side of things with the Cuban police. There weren't really ... they didn't really understand what I was getting up to. 

Phil: Right, so they don't take kindly to people putting themselves in danger?

Dan P.: They don't, they don't and you can look at that two ways right. You can say that's kind of a restriction on peoples freedom and we should be allowed to explore and put ourselves into those situations. And you know, you could look at it another way and say, that's why Cuban healthcare works are because they take really preventative kind of social outlook on the well being of the entire community. So like everything in Cuba it really you could go either way on it and really try to look at it in a very flexible way.

Phil: Does travel mean to you then? What have you learned from it?

Dan P.: Absolutely. I think there's a lot to be said for learning that, really human beings at their basis are all, have the same motivation and the same drive and that comes around. Making sure that there's always more opportunity for the people that you care the most about. And that takes on a lot of different forms, but mostly people wanna see their kids have great access to schools and education. They want safety, they want security. So the more I've traveled throughout the world to places like Cuba, or Bolivia or some places in Southeast Asia that ... I'm always struck by just the universality of that concept, that everyone is really after the same things and thinking about how we can help give people more access to those core, those core things.

Phil: And how do you take that back to where you are now? I mean you've learned all those things. How do you ... Is there any opportunity the way you're living now to bring those to life?

Dan P.: Yeah, absolutely. I mean I try to do it in small ways through, through supporting organizations like Kiva, through microloans. And trying to ... when I travel myself and I'm lucky to have an opportunity both for work and pleasure to continue to travel, to take advantage of different opportunities. I mean I was in Rio in June for a wedding and spent a few days in the pavellas there, just learning about the challenges there. And doing some volunteering there.

Dan P.: So I'm definitely a fan of those opportunities while abroad to go out and make an impact on a local level and then I think, you know, all of us, particularly I think in parts of the world like the United States, where there's kind of imbalance of power, I think it's important to speak to that. And to make smart decisions here.

Phil: Hey listen, tell me, what's a Brazilian wedding like then? What's a wedding in Rio like?

Dan P.: Oh my god! Well, I was very lucky. I had the chance to meet a Brazilian supermodel in Mexico a few years back. (laughs) Very rumbling.

Phil: Oh, lucky you.

Dan P.: Yeah. Have since managed to become, strangely enough, better friends with her and her now husband. They're two close friends of mine. They invited me down to their wedding in Rio that was basically ... The bridal party was seven Brazilian supermodels and me and it was great. (laughs) I can't go into ... While I can tell stories about lying to the U.S. Government, I'm not actually allowed to tell stories about that wedding in Rio because it - (laughs) It might [inaudible 00:11:17]. No, it was, it was wonderful. It was an amazing trip.

Phil: You don't go to a supermodels wedding very often. (laughs)

Dan P.: That's once in a lifetime.

Phil: Yeah. (laughs)

Dan P.: I think that one was once in a lifetime. Absolutely, I remember ... I mean remember in Argentina all the way in the South of Patagonia getting invited to the wedding of a woman that I'd met on a bus and she was just like, you know, you're always gonna be, I think, particularly the further afield you go from kind of the standard tourist spots. You're always gonna be a bit of curiosity and yeah, they were so excited to welcome me into that wedding. You know, weddings I mean, they you know ... They made a movie about wedding crashing for a reason right? It's one of the best things out there. (laughs)

Phil: All right. Brazilian supermodel weddings aside, some of your favorite places that you've visited out of the 50? Just give us a ... just give us a taste of where you've been.

Dan P.: Absolutely. One bicycle tour around New Zealand. North and South islands of New Zealand. [crosstalk 00:12:12]

Phil: Wait, wait, wait, wait, wait a minute. Wait a minute. Bicycle to New Zealand? It's a bit hilly, right?

Dan P.: That's a bit hilly and I'll tell you that Kiwi's are of course the sweetest, nicest, most wonderful people outside of a car. They are absolute terrors when behind the wheel. (laughs) I was by myself and I got down to the South Island and I would knock on a door and say, "Hey, you know, I'm riding my bicycle across New Zealand, wondering if I might pitch a tent in your paddock?" And these people would look at me like I was absolutely insane. And they would say, "Why don't you come inside and have a hot meal and sleep in a bed." And it got to the point where, if I pulled up to somebodies house and I said, "Hey, I've got my tent, mind if I pitch my tent in your paddock?" They'd said, "Yeah go for it." You know what I've got a couple more miles in my legs, I think I'm gonna keep riding. And I would just go right next door, and of course, they would welcome me in.

Dan P.: So I got a little spoiled there, but New Zealand is, I mean, just such an amazing place. Mexico, I've now been lucky to spend probably a couple years total in Mexico traveling throughout Mexico. The just pure range of different cultures in Mexico, it's something I didn't really know existed, but across food and art and language and temperament. They're so many different parts, and of course geography and what the landscape actually looks like. I mean Mexico is just as diverse as the United States.

Dan P.: So, Oaxaca in particular, down in the coast of Oaxaca, there's a town called Mazunte which where I lived for about six months. And that is just paradise on Earth. To me it's the last place in Mexico that really is not overdeveloped and yet still has just the most spectacular landscapes and beaches. So I love Mexico. I mean Southeast Asia for like a beach vacation, you can't really beat just hanging out on the beach in Thailand or Indonesia. Your part of the world, Australia. When I was 18, down to that, that whole kinda east coast route. I don't think I could survive that at 31. But maybe I'm selling myself short and I should try to give it a shot and try to relive my earlier glory days.

Phil: Hey listen, look you've generous enough to give me your time here, so here is my opportunity to give a little bit back to you too. Do you wanna talk about the Bulk Collective? What's that about? How can we help out?

Dan P.: Oh, cool. Yeah, yeah sure. So that's a new company that I started last year. The basic idea, you bring a community of like-minded explorers together and you use their collective purchasing power, so pool their resources. To unlock travel experiences. So great example of that, in January we were down in the British Virgin Islands and I'd been on the phone with these charter companies saying, "Hey, we wanna rent four catamarans, we're looking for a 40% volume discount." Which takes something that normally would cost a couple thousand U.S. dollars per person, makes it more like $1200. Just opens those kinds of exclusive experiences out to more people.

Dan P.: So I think of it as kind of like group travel, for people who hate group travel, 'cause nothing is mandatory. It's all optional. And hopefully, it provides kind of a framework for personal growth and folks to meet new lifelong friends.

Phil: And how longs that been going? I mean you've done a BVI. You've had other trips as well?

Dan P.: Yeah, yeah. So, the first experience, the first Bolt experience was down in Oaxaca. Over in a year or so brought folks down to that town that I lived in for six months and we rented out this entire compound of treehouse villas. And every day there was just an optional piece of programming, whether it's folks jumping into a temezcal, which is the native's sweat lodge and having a ceremony. Another day we chartered a boat and went whale watching out to a private beach. New Year's Eve dinner right there on the beach in town.

Dan P.: So, really trying to bring a sense of, apart from bringing amazing people to amazing places, like really trying to bring like a sense of design and make these experiences really thoughtful and kind of ... The adjectives that come to mind are, unexpected, delightful and really thoughtful. So, yeah, so we've done three of them now. Oaxaca rode down to the British Virgin Islands with our fleet of catamarans, which is also spectacular. Or maybe that's not quite the right word but, just a really amazing, important time to be there, in the wake of Irma and Maria the hurricanes that came through back in August and September. Just seeing the resilience of the Caribbean people and folks living down in the Caribbean. They're rebuilding and they're there to stay.

Phil: How can people make contact with the Bolt Collective then?

Dan P.: Sure, we're just at or you can type in Bolts Collective and it'll come up with our Instagram, Twitter, website. And yeah, I think we're looking for people, it's a bit of a different community in that we're organized around things like adaptability, adventurousness, curiousness, our people just generally really nice people. So those are the kinda folks that we're trying to attract and that we have a bit of an interview process for. So if that sounds like it's right up your alley and folks are thinking maybe any of those experiences kinda peak their interest. Yeah, we're pretty easy to find out there on the internet.

Phil: Dan, thanks very much mate. You are an amazing nomad. Thank you so much for spending some time to tell us about some of your travels.

Dan P.: Hey cheers Phil. Hope to see you in Australia soon.

Phil: We will have a link to the Bolt Collective in show notes. And by the way, Dan's professional background is in the production of events for brands like Airbnb and the Rockefeller Foundation. He's also the creator of Subway Sets a sold-out concert series bringing New York's best underground musicians up to rooftops above the city, love that.

Speaker 3: Oh, yes, please. If you know an amazing nomad we should feature, email us, podcast@worldnomads. com. You can find our bonus episodes alongside the world nomads podcast on iTunes.

Speaker 1: Amazing nomads - be inspired.

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