Guest Bio
Lisa Pagotto is the founder and CEO of Crooked Compass, a pioneering adventure travel company redefining how people engage with the world. With a deep commitment to cultural integrity and immersive experiences, Lisa has carved out a space for meaningful, off-the-beaten-path journeys that challenge traditional tourism models. Her leadership empowers travelers to connect authentically with remote and emerging destinations — far beyond the ordinary itinerary.
Lisa is also a captivating speaker known for her raw honesty and practical wisdom. Drawing from her entrepreneurial path, she encourages audiences to embrace uncertainty, trust their instincts, and lead with resilience rather than perfection. Her storytelling inspires people to transform setbacks into opportunities and to rethink what success truly looks like. Whether on stage or in the field, Lisa champions bold thinking and values-driven exploration as tools for personal and collective growth.
Show Summary
In this episode of the Big World Made Small Adventure Travel Podcast, host Jason Elkins speaks with Lisa about her journey building Crooked Compass into a leader in experiential travel. They dive into how the company curates unconventional itineraries, often in lesser-known or emerging regions, offering travelers both challenge and connection in equal measure.
Lisa shares how safety remains a top priority in these remote adventures, and how traveler psychology — especially around risk and group dynamics — plays a crucial role in the experience. She also reflects on how her early travel memories shaped her vision for Crooked Compass, and what she’s learned along the way as a founder navigating the ever-evolving world of entrepreneurship. The conversation highlights the power of trusting yourself, staying flexible, and pushing past the expected to create something truly original.
Key Takeaways
- ✓ Crooked Compass specializes in immersive travel to unconventional and emerging destinations
- ✓ Safety is a core pillar, especially in regions with complex dynamics
- ✓ Many travelers are open to taking greater risk when the experience is unique and meaningful
- ✓ Group chemistry can shape the entire arc of a travel experience
- ✓ Repeat travelers often build lasting community through shared journeys
- ✓ Early travel influences often guide future adventure choices
- ✓ Building a business starts with self-belief and a willingness to take risks
- ✓ Flexibility allows for richer, often unexpected experiences
- ✓ Cultural perceptions are frequently challenged by firsthand travel
- ✓ Entrepreneurship is a constant learning curve driven by resilience
What You’ll Find on Crooked Compass
- Tailored adventures to off-the-map and emerging destinations
- A strong focus on cultural respect and responsible travel
- Small group journeys that foster connection and community
- Itineraries built for curious, courageous, and conscious travelers
- Expert guidance with an emphasis on safety and authenticity
- Stories and experiences that challenge the way we see the world
Learn more about Crooked Compass and connect with Lisa at:
https://www.crooked-compass.com
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Podcast Transcript
This transcript is auto-generated on recording, and has not been edited by a human. It may contain lots of mistakes, crazy words, and stuff that makes no sense. The host and the guest are not responsible for the accuracy of the transcript.
Jason Elkins (00:00.954)
Welcome back everybody to another episode of the Big World Made Small podcast for the adventure traveler. So happy to have each and every one of you back today and super excited to have a special guest with us as well. We’ve got Lisa Pagato. She is the founder and CEO of Crooked Compass. Lisa, welcome to the show. Happy to have you here.
Lisa Pagotto (00:18.562)
Thanks Jason, thank you for having me.
Jason Elkins (00:20.998)
I know you are kind of an old pro with podcasts. know you’ve been on quite a few different shows and this is kind of nothing new for you, but hopefully we’re gonna touch on some things that maybe you haven’t discussed in the past, some kind of childhood stuff, traumas, whatever things happened that caused you to go this direction in life. I’m sure there were a few. And so that’ll be fun. Before we do that though, Lisa, just maybe for our listeners, give them kind of a quick idea of what is Crooked Compass? So maybe the 36,
60-second elevator pitch and we’ll kind of go from there.
Lisa Pagotto (00:53.71)
Yeah sure, so Crooked Compass, so we do both small group touring and private touring, really focusing on your more emerging frontier, challenging geopolitical type destinations. So the more tricky it is to logistically plan and put together, the better it sells for us. So we basically cater for people who are very well traveled, they’re looking for that what’s new and what’s next and they’re looking to do it at a premium level.
Jason Elkins (01:21.772)
said when you said complicated the first thing that popped in my head was the United States
Lisa Pagotto (01:27.474)
So we don’t do the United States, it’s not quite frontier enough. That’s a different level of geopolitics to what we tinker with.
Jason Elkins (01:31.654)
Well, well, I know there’s some travel complications there right now, but kind of a joke. We’re going to get into kind of what some of those places are and what you mean by that. Before we do that, I’m sure all of our listeners kind of figured it out intuitively, but you mentioned, I can’t remember the exact term you I think you mentioned private and group.
Are those the two words you use? So just for those that might like, well, what’s a group? If I bring my family, is that a group or is that private? So give us just kind of what’s definition between private and group in your world.
Lisa Pagotto (01:57.794)
Yes. Correct.
Lisa Pagotto (02:09.741)
Sure, so small group is there’s fixed dates for the set itinerary and you basically book on to that date and that’s a maximum of 12 people so very small and intimate and then private touring is anything so if you wanted to travel just with your family and not anybody else we would do that as a private tour and that could be replicating one of our existing itineraries it could be curating something completely from scratch it could be just one person it could be a couple so anything that falls outside of a scheduled tour that is on our website
into the private touring category.
Jason Elkins (02:42.0)
So let’s just say, well, let’s not be hypothetical. Do you have kind of fixed number of destinations, and by destinations I mean countries, can you clearly say we do 22 countries, or is it we’ll do pretty much any country if it makes sense and we’re able to help our clients put together a good trip, or how does that work?
Lisa Pagotto (03:05.76)
Yeah, so we operate in 46 different countries and in terms of our small group tours we have 142 departures across those 46 countries and then on top of that we do private touring but only to the destinations where we offer small group touring as well because that’s where our relationships are.
Jason Elkins (03:24.23)
Nice. Okay, very, cool. Do you want to give us? I don’t want to make any like I told you the first thing that popped into my head was the United States Obviously that was kind of a joke meant to be a joke but give us an idea Are we talking, you know, North Korea? Turkmenistan type places. What are we what are we talking about?
Lisa Pagotto (03:40.289)
We are.
Tick tick, both of those. Yes, so North Korea. But unfortunately, the border still hasn’t reopened post pandemic, but we have an incredible wait list. So we are, you know, waiting with bated breath for that destination to reopen. That used to be number three for us before the borders closed. Papua New Guinea is one of the more challenging ones. We do do Turkmenistan. We do that that whole Silk Road area. So all of the Stan countries, Central Asia. We do a lot of West Africa as well. Togo, Benin, Ghana.
Jason Elkins (03:57.146)
Wow, okay.
Lisa Pagotto (04:11.248)
those areas a bit of Congo We also do Mongolia is a huge destination for us very very big Timor Tibet Where else have we got the Guyanas in South America Colombia? Yeah, that there’s there’s and a lot of the Middle East so Saudi Arabia Oman Lebanon we’ve just reopened and yeah that that region’s obviously a bit of a shifting beast but yeah, one of the biggest parts of our
Jason Elkins (04:37.254)
you
Lisa Pagotto (04:41.208)
business was the Middle Eastern. It’s good to see it’s starting to bounce back now.
Jason Elkins (04:45.67)
I feel compelled to have a conversation about perceptions around safety. Because I have a feeling you have these, well I don’t know if you have these conversations a lot because the way you put yourself out there, I’m guessing you kind of self-select people that aren’t too terribly worried. I don’t know if I should say worried, maybe they are, I don’t want to put any words in your mouth.
Lisa Pagotto (04:53.129)
Yes, go for it.
Jason Elkins (05:12.304)
Let’s talk about what kind of people you attract into your business and then how those conversations come up around safety.
Lisa Pagotto (05:15.863)
Yes.
Lisa Pagotto (05:20.142)
Yes, so I guess just to sort of provide context to where you were going with that, it is a conversation that we do have very often, especially when a destination is just like emerging from a war, a civil war, local conflict, whatever it might be, tribal conflict. And it is something that we do have to take very seriously. Obviously, passenger safety has to be paramount. And we’re certainly no cowboy operator that’s just like, all right, war’s over, let’s go. That’s not how it works.
Jason Elkins (05:46.832)
Well, let me ask you this before we go any further though. Because kind of what I heard you say is safety has to be paramount. It’s kind of that safety first thing, right? We talk about safety first, but honestly, Lisa, if it was really safety first, maybe you wouldn’t be doing anything other than Italy tours.
Lisa Pagotto (05:57.825)
Yes.
Lisa Pagotto (06:10.446)
Well, I mean, Paris is the number one city in the world for terrorism attacks. that just let’s just put some perspective here. But to go back to who our travellers are, because that will also provide further context here. So as I mentioned before, our travellers are really, really well-travelled. They’re looking for that what’s new, what’s next. We do have a bit of ego with some, not all, but some of our travellers who want to be the first to get to a destination that’s reopened.
Jason Elkins (06:16.582)
that’s a good perspective. I love it. I love it.
Lisa Pagotto (06:40.48)
the dinner party store is they you know didn’t I’ve just been here I got VIP access and behind the scenes this and that that’s what they want and that’s those people have a higher risk tolerance is probably the best way of putting it but not in terms of stupidity you know these people are very well educated they are very very curious minded and they have time and money on their side we’re talking the sort of self-funded retiree market is who most of our travelers are and so
Jason Elkins (06:50.452)
huh, yeah.
Lisa Pagotto (07:10.32)
A lot of our travelers went to Afghanistan back in the 70s when it was a very, very different world and it’s one of the most incredible places. So they’ve been to destinations like that before they’ve gone through more modern situations. And now they want to go back. with Syria. And obviously we have to tread very, very carefully with these destinations. not just to put a caveat there, we’re not operating in Afghanistan at the moment or Syria for that matter.
Jason Elkins (07:23.622)
Mm-hmm.
Lisa Pagotto (07:40.32)
we can’t get insurance as a tour operator, we can’t operate because if we can’t get insurance they’re not going to be able to get travel insurance and we need to have both to be able to operate. That’s kind of the baseline. If we can’t get insurance it’s just not an option because the traveler can’t get insurance.
Jason Elkins (07:57.574)
And even if the traveler said, hey, don’t worry, I don’t care, I’ll self insure, it’s still your business. You don’t wanna put your business on the line. Yeah, yeah, exactly.
Lisa Pagotto (08:05.27)
We take the payment, we’re liable. It’s just not worth it. We do so much due diligence and risk assessment and risk management and evacuation, security evacuation, all the planning that we have to do and not just for extreme destinations. We do that for everywhere. We do it in Vietnam. We do it in Morocco. All of those destinations as well, because I mean, you mentioned Italy before and I used Paris as the example. Anything can happen anywhere at any time without notice. I look, I’m based in Sydney. Look what just happened here.
before Christmas. Just because it’s a well-established Western country it doesn’t mean that it’s you know void from things going awry, which I like to remind people of.
Jason Elkins (08:46.858)
And, well yeah, that’s where I was gonna go with this next question. I don’t know if it’s a question as much as an observation that it’s interesting how many people I’ve run into, know, having grown up in the US and having a lot of connections to the US and probably some similar mindsets to Australian travelers can be. I don’t know, you tell me. But I’ve heard so many people in the US talk about, I would never go there. That’s really…
dangerous. I remember it was many years ago, I’m sure no one listening to this will remember the exact the case, but I remember I was speaking to someone about going fishing, saltwater fly fishing, and had suggested
place on Belize. I suggested this great place in Belize. We were talking about it and he’s very concerned. He’s like, wow, I don’t know. I heard something about gorillas along the border with Belize and Guatemala. It just sounds really dangerous. I heard something about a bus got hijacked or something and I just happened to ask him. I said, I’m just curious, where do you live? And he said, well, I live in Oakland, California. And some people will recognize Oakland, California doesn’t necessarily have the best reputation for safety. But again, that’s the conversation.
perception stuff. And just like a week before that they’d had a big shootout where a bunch of cops got shot and killed and and it was so interesting for this man to be worried about going to Belize but sometimes we’re willing to accept that stuff around us in our neighborhoods where we live but if we read anything about it in another country that we’re not familiar with it it’s just interesting how people respond to that.
Lisa Pagotto (10:03.799)
Yeah.
Lisa Pagotto (10:27.598)
Yeah.
Yeah, can add to that. I, yeah, no, that’s okay. And that is, you know, one of the biggest barriers that we have is people question safety and we have to be able to answer it. And if you don’t feel comfortable with our answer, we’re not the right to accompany for you. Or perhaps that destination is not the right destination for you. But in terms of, guess, taking risk and not recognising what’s literally happening in your own backyard, people seem to have a bit of a filter with what they’re prepared to accept in a different country. And I mean, even in the most
Jason Elkins (10:29.83)
I don’t… Yeah, please do. Because I don’t know where I’m going with it.
Lisa Pagotto (10:59.2)
most tame travel sense like going to Fiji or something like that, people are always more likely to take some kind of risk because they’re somewhere exotic and somewhere exciting as opposed to in their own home. And it’s just it’s a really interesting sort of psychological element of the human brain, but just sort of heading back to our travelers. So they’re also people who aren’t easily swayed by what they see in the media because the media play. Yeah, they play.
Jason Elkins (11:26.628)
I suspect so.
Lisa Pagotto (11:29.104)
a big, big part of how people perceive things. Everything’s click bait, everything’s scare tactics. And because they’re so curious minded and they’re so educated, they want to go and see it for themselves. If there’s a tour operator that can get insurance and you can get travel insurance, there’s a pretty good, and your government travel warning says that it doesn’t say do not travel. And again, those travel warnings, we’re an Australian owned business, so we’re governed by DFAT, our equivalent of
Well every country has their own, the British have the FCO and the US have their version as well but if it’s under do not travel that voids our insurance immediately. So you know that there’s certain parameters that we need to or we don’t need to we choose to work within because there’s other businesses who certainly will operate without insurance and we’ll take that risk but we’re not them.
Jason Elkins (12:23.014)
Yeah, it’s, I was just having a conversation recently about kind of the stuff. People are either open to certain things or they’re not. And, you know, trying to accommodate those that are not interested in what you offer is not good for anybody. It’s not good for you, it’s not good for them. It’s just kind of, you know, just.
Lisa Pagotto (12:32.674)
Yeah.
Jason Elkins (12:45.24)
just kind of pretending, yeah we can help you when you can’t really. So and the reason I bring this up is I remember someone came to me back when I was setting up a lot of these trips to different places in the world. had somebody that worked in the same company. wasn’t, I ran the travel business for this company. Had somebody that worked in the company outside of the travel business. He came to me and said, you know my wife is terrified to travel outside the U.S. I really want to take her to Europe.
You guys should come up for trips. You should come up with trips for people that are afraid to travel.
Lisa Pagotto (13:21.334)
but that’s a tough market to crack. That’s yeah, that’s like a niche within a niche.
Jason Elkins (13:25.926)
Yeah, and I can joke about Adele, but when he said it he was dead honest, you know, just being serious and I didn’t laugh at him. I you know, but it’s it’s interesting. It’s like It doesn’t matter how great of a trip you put together if people aren’t inclined to take that type of trip if they’re not open to the curiosity and the putting themselves in uncomfortable situations They’re not gonna do it. So I think it’s really smart to I guess what I’m going with all this is I love
that you basically have identified. Look, we’re helping people go to places that are not easy to get to, that are not necessarily the popular places that just kind of self-select for the type of person that’s actually gonna book a trip with you, guess, right?
Lisa Pagotto (14:10.22)
Yeah, yeah, exactly. And they’re not something you can put together with, you know, chat GPT or Google or anything like that. Like you need a specialist to help you get there. And that is really where where our specialty sits. And, you know, further to that, people respect that. And so much about what we do is just being so bluntly honest with managing expectations to the point where sometimes it feels like we’re telling someone not to come with us by, you know, there’s not going to be hot water. You might not have toilets for three days.
depending on what it is. But that’s how we get the right people on our tours. Because if you’re not okay, you want to go and sleep next to the crater in Turkmenistan that’s still burning for the next 18 months or so, you have to sleep on the floor in a yurt and you have to use shared facilities. If you’re not okay with that, then don’t come.
Jason Elkins (15:00.518)
Well, and especially at a group trip where you’ve got, you know.
Lisa Pagotto (15:03.36)
Yeah, well, group dynamics is everything. doesn’t, you know, we’ve all experienced it. It doesn’t take much for that one person and there’s always one. And if you don’t know who it is, it’s probably you.
Jason Elkins (15:12.57)
I love that you said, I was getting ready to say it because I’d heard that conversation with someone recently, like, there’s always one jerk in the group and if you can’t figure out who it is. Yeah, yeah. Do, I don’t know if it’s fair to ask this question, but I suspect you have a lot of repeat in your groups, a lot of people that go, have been on many group trips with you.
Lisa Pagotto (15:21.079)
Yep.
Lisa Pagotto (15:38.731)
Yeah.
Jason Elkins (15:39.238)
Do you, if you average, if you average it, like on a typical group trip you’re doing, roughly what percentage of the people on the trip would you say have been with you on a trip before, or have traveled in a group trip before? Is it the 10 % or is it 50, what does that normally look like? I had a feeling.
Lisa Pagotto (15:58.592)
It’s over 50. It’s over 50. So generally what we see, yeah, once people sort of find us and they are like, wow, yeah, this is, this is my style. This is how I want to travel moving forward. They keep sticking with us until they get to a point where there’s a destination that they want that we can’t deliver. But otherwise, once they come through that cycle again, once they’ve done their Greek Island sailing or whatever it is that they might do, and they get ready to do that next more adventurous type destination, then they come back to us. So
Yeah, we have a very strong, and like once a year, so I run a founders tour. Once a year hosted by me, never to be repeated, elevated way above anything else that we offer. And that is 100 % sold out with repeat passengers every year.
Jason Elkins (16:43.91)
and I’m envisioning the dinner conversations, especially like the first night or two.
And you’ve got, you know, Bob over here who’s been on six trips and names off all the places he’s gone with you. And then you’ve got, you know, Mary over here that’s like, oh, you went there. Oh yeah, I went there with them the year before when we did this and they’re, and they probably all know people like, oh, there was this guy in our group last year that, and the other person’s like, oh, I know that guy. I went here with him. I, right. Is that pretty much what the conversation is like at dinner? I know.
Lisa Pagotto (17:14.11)
Yeah, that’s what happens. And then I just sit back and they all sell themselves onto each other’s tours that they’ve done. It’s like the perfect marketing formula. I’ve put a bunch of people together who have done a couple of tours with us and then by the end they’re all booked on the ones that they haven’t done that the other ones have done. So yeah, it’s quite incredible.
Jason Elkins (17:19.461)
You
Jason Elkins (17:30.443)
yeah, that resonates so well.
That’s what I was doing when I was leading a lot of group trips. And I remember it was great because I took a job running a travel business for this company. And when I got there, I took the job because I wanted to go a lot of places. I wanted to see a lot of places. And my boss, I just loved his attitude. He’s like, Jason, I want you to take as many trips as possible because your job is to sell trips.
Lisa Pagotto (17:53.56)
Fair enough.
Jason Elkins (18:02.979)
You know develop trips but sell trips and when it all comes down to it and he said and the best place to sell a trip is on a trip and It was it was so true. I mean it was it was so quick to get to the point of every trip I went on at the end of the trip. It was like where are we going next? Not where you going next? It’s like where are we going next and the people yeah, the people in the group would all become friends So then it was like the last night the whole conversation is where are we all going next?
Lisa Pagotto (18:09.422)
Yeah.
Lisa Pagotto (18:23.968)
Yep, they’re in.
Jason Elkins (18:32.903)
And very quickly it was at least 50 % of every trip. I had a few trips, you know, probably like your founders trips that are just everybody on the group that traveled with me before. It was almost like, man, we need to do something to let some new people come in too.
Lisa Pagotto (18:47.946)
I know, I know, it’s like gone in 24 hours, it’s not even breathing space for any new blood to come through.
Jason Elkins (18:54.181)
But it was so much fun because it allowed so many, it was so fun to sit down with the guests and listen to them talk about where they wanted to go. Because they might say, Jason, where are we going next? I’d say, well, I don’t know. Just curious.
if we could go anywhere, where would you want to go? And then you get that kind of consensus and then it got so then I’d go back and start doing some research and say, you know what? Yeah, actually, I’d kind of like to go there too. So I’d put a trip together around what they said that they wanted to do. It was was a lot of fun. So and you know, the other thing that I bet comes up during those conversations and is that there’s a bit of Lisa, how the hell did you get into this?
Lisa Pagotto (19:32.012)
Yeah, yep, everybody wants the story.
Jason Elkins (19:32.453)
Walk us through this so let’s do let’s do our listeners a favor and let’s for those people that haven’t been able to have that conversation with you around the dinner table at some exotic place Let’s let’s I’m gonna ask you those questions that I know you’ve been asked a thousand times Lisa. Where did you grow up?
Lisa Pagotto (19:50.83)
I grew up in Sydney, Australia. So, local girl, yes.
Jason Elkins (19:53.349)
Okay. Yeah. And what was going on when you were a kid? Did you ever think you were going be doing this kind of stuff?
Lisa Pagotto (20:00.607)
not to this extent, but yeah, probably from the age of eight, I was like, I want to be, I didn’t know the breadth of what was possible in the travel industry. All that I knew that existed was a travel agent and an air hostess.
So I knew that I wanted to be one of those two. And I was really, really privileged as a child. I got to travel overseas a lot with my father’s work. I grew up with the most incredible Nana who was, you know, she lived in Perth, so the other side of Australia, but in the school holidays she would come and stay with my brother and I and she would bring over coins from different countries she’d been to. She would tell me stories about when she went to China and you had to take your own padlock to lock your hotel room and you’d use coupons.
Jason Elkins (20:13.455)
Okay.
Lisa Pagotto (20:42.816)
to buy food and so I grew up hearing those stories and so it was just naturally embedded into me that I would travel and my nan yeah Nana yeah grandmother yes sorry that could be an Australian term yes my grandmother
Jason Elkins (20:50.789)
You said that was your said that was your net did you use the word Nana? Help me Nana means grandmother, right? I’ve heard it before I think some people in us use it it’s it’s I just want to make sure I was clear because Because we have this term like I don’t know if we have a term but we talk about like
Lisa Pagotto (21:06.786)
Yes.
Jason Elkins (21:13.315)
lot of families have a crazy aunt or crazy uncle that, you know, kind of left the normal routine and has been traveling for 30 years and sending postcards and has been to all these places. It sounds like maybe your nana was pretty adventurous.
Lisa Pagotto (21:28.874)
Yeah, yeah, she was. And I mean, she was married, but off she would go. She’d go travelling through the Middle East for months at a time on her own. She ended up becoming an English teacher in Tunisia. And she would constantly say to my parents, let me take Lisa and Michael, my brother, let me take them to Tunisia. I want them to meet these families that I, you know, I teach their children. And my parents were like, no way. North Africa is so dangerous. There is no way the kids are going. And I was so desperate to go. And so the minute that I turned
I was like, bye guys, I’m out. And I said to my Nana, I’m coming to Tunisia, let’s go together. And so we went and that was my first, yeah, that was my first experience of somewhere that, well, even now still, I mean, in particular in the Australian market, I’m not sure about the US, but Tunisia is very unheard of. You ask most Australians where it is, they wouldn’t be able to point to it on a map. So it’s very exotic from our perspective.
Jason Elkins (22:07.308)
So cool.
Lisa Pagotto (22:28.804)
And that was my first exposure to something that wasn’t Asia or the Pacific. It was something that was different. It was Islamic. I’d never heard call to prayer. I’d never seen goat carcasses hanging in the street. Everything was different. The food, the culture, the architecture. And I was like, wow, what else is out there?
Jason Elkins (22:48.857)
So other than I get the whole like, I don’t know if I use the word stimulation. need to stimulate. That’s why I like to travel to places like that is because there’s so many new things to see. I probably have a dopamine imbalance in my head that probably gets satisfied when I have these new experiences. So I know that novelty is a big part of it for me, but I also know that, well.
Honestly, what I hear you saying is kind of like almost the forbidden fruit or the your parents say no, you can’t go to North Africa. And then as soon as you can go, you’re like, I’m going to North Africa. Right. So I wonder how much of it is just the novelty of it as opposed to just that sense of freedom like I get to decide where I’m going. What do you think? What’s the mix? Is it 50 50 or do you think?
Lisa Pagotto (23:23.394)
I’m outta here.
Lisa Pagotto (23:36.846)
I would say probably at the age of 18 it was probably an element of rebellion but because that’s something that has stuck with me obviously now I don’t need my parents approval to do anything I’m a parent myself it’s the curiosity the curiosity of what else is out there that I haven’t seen that is so so different that I can learn from that’s really the basis of it and I ended up living overseas for three years and I was a tour leader through Western Europe but beyond that anytime I would have downtime
I wasn’t doing the, you know, boozy way through German beer halls or anything like that. I was, you know, I had a month in India, I had a month in Turkey, I had a month in Egypt. I was doing things as at that point a 21 year old that was not what other 21 year olds that were backpacking were doing. And that really kind of built that framework of what I enjoyed getting out of travel. mean, Italy and France and Germany and all of that are beautiful, but that wasn’t what stimulated my mind.
And yeah, I started off as a travel agent, was a tour guide, worked in product marketing and just literally got to this point of a light bulb moment where I was building a brand for another tour company. And I was like, why am I doing this for myself, but in my style of travel?
Jason Elkins (24:38.159)
Get it.
Jason Elkins (24:52.933)
Okay, we’re gonna come right back to that. And before we do, just help me, I wanna kinda understand the timeline. What I heard was, okay, I’m 18, I’m going to Tunisia with grandma. And it sounds like you just kinda kept doing that, cause you were mentioning 18, 19, 20, early 20s. Were you going to school as well or working or just did you do like the year long, I guess Aussies would call it walkabout?
that just lasted longer? Is that what the first few years were like or what were you doing?
Lisa Pagotto (25:20.59)
No, well yes and no. So when I left school I went to college and I started to be a travel agent. So I worked as a travel agent when I was 18 and then just before my 19th birthday was when I went to Tunisia and then I was overseas for a year. I came back for 18 months, had itchy feet and then I went back again for another two years which was when I was a tour leader. So when I came back in that gap I was also in the travel industry as well but behind the scenes.
Jason Elkins (25:28.613)
Okay, cool.
Jason Elkins (25:44.517)
Okay, so.
Lisa Pagotto (25:50.604)
in the wholesale side of things.
Jason Elkins (25:53.285)
Do remember, cause you were already going to school to be a travel agent, sounds like 18-ish, traveled to Asia. Do you remember a moment, I don’t know, I’m imagining thinking, initially you were probably meeting people like your grandmother that had been a lot of places. Do you remember the moment when you realized, oh sh, oh crud, I’m not gonna, I’m trying to keep this clean, but in my mind I’m thinking, oh shit.
Lisa Pagotto (25:57.259)
Mm-hmm.
Jason Elkins (26:21.273)
I’ve been to a lot of places. I kind of actually have a lot of experience and I’m and where that that realization came that maybe you were a little bit different than everybody else.
Lisa Pagotto (26:32.91)
I don’t think that I actually realised that I was different until probably, so my business that I run now, I’ve had it for 12 years, it probably wasn’t until…
six years into that business that I realised that and that was nearly 20 years into my career. So I never understood it. I never understood why every job in the travel industry I interviewed for I got. I never understood what I did that was so different from anybody else. never understood, I never recognised that I had this unique first-hand experience that other people didn’t. You know, they had to sell from a brochure or from what they could learn online. I just, it just didn’t register and people would say things, you know, people would make comments like, wow,
you’re so well traveled for someone your age. Wow, look at the things that you’ve done. And it just, it just never registered, never registered at all. And I just didn’t get it.
Jason Elkins (27:23.877)
Did you remember feeling well? No, there’s so many other places, like more focused on all the experiences that you wanted to have that you didn’t maybe stop to reflect and say, wow, look at all this stuff I’ve done. So when someone says you’re well-traveled, you’re like, no, I haven’t been to North Korea yet or whatever. Was it like that or?
Lisa Pagotto (27:44.79)
Not really. It probably wasn’t until people started being fascinated by how many countries have you been to. Because you would hear the comments of, you’ve just been traveling again. how many countries are you up to? And then I didn’t actually keep count because I didn’t realize that it was a thing. And especially with people from the US, the travelers from the US, you know, this is very generalist, but so many of them are country counters. And so one day I went, OK, well, maybe I’ll make a list and I’ll see.
Jason Elkins (28:00.805)
thing.
Lisa Pagotto (28:14.774)
my number is. And then when I started actually having a number to share with people, that was when I was like, whoa, okay, okay, yeah, okay, I’m very privileged. I’ve been very, very lucky with what I’ve done and where I’ve been.
Jason Elkins (28:31.119)
love that you say that you were privileged because that’s kind of the way I look at it when people are, you’re probably way ahead of me if we were counting. But I think a lot of people said, wow, you’re so, you know.
Well-traveled whatever you’ve been a lot of places and I make you know what? Yeah, I’m very fortunate and not because Somebody gave me a bunch of money not because I made a good stock choice or anything I mean most of the time when I’m traveling I’m eating ramen noodles and I’m staying really crummy Airbnb’s so but it’s I still feel very fortunate to have had those those experiences Is there
I think I know better than to ask you what your favorite place is because I know when people ask me that it’s really really hard. I won’t even put you on the spot but if it’s something you want to share that’s great. But I will ask you is there a place calling your name that you haven’t been to yet that you’re super excited about?
Lisa Pagotto (29:31.071)
Yeah, there’s-
There’s quite a few places that I haven’t been to. I’m desperate to get to Mali, but there’s a civil war conflict going on there at the moment, so that’s not going to happen anytime soon. I’m so, so interested in hiking through what’s known as Dogon country. It’s very tribal in the mountains of Mali. So that’s one for who knows when, sometime in the future. That’s probably the biggest one on my list. I do really, really want to get to Afghanistan too.
but yeah also again I have to I have to be patient so they’re probably the two that are sitting at the top.
Jason Elkins (30:10.309)
So let’s use those as the example. Let’s use Afghanistan as the example. Can you put your finger on what it is that you’re most intrigued about or intrigued by in a country like Afghanistan? Yes, okay, go ahead.
Lisa Pagotto (30:22.508)
Yes.
Yes, I can. So I guess it comes from what you learn from traveling in surrounding countries. So I’ve spent a month traveling through Pakistan. I’ve spent time in mainland Yemen. I’ve spent time in Iraq, Iran, basically everything that surrounds Afghanistan except for Afghanistan itself. so and I also haven’t been to Tajikistan, interestingly, which also borders Afghanistan. But interestingly, with all of those countries and Pakistan in particular, there’s leakage over the borders.
of those cultures and I just find it fascinating like I just that Middle Eastern, Central Asian culture, cuisine, it’s my favourite part of the world, the history, the ancient, ancient history, not so much the more recent conflicts but just that you know really ancient civilisation side of things really, really fascinates me and Afghanistan is one of those places where there is so much of that. So that is a big draw card, the food, the hospitality and I guess as well
you know even though I mentioned I’m not so you know deeply fascinated in the more recent changes with the Taliban and that sort of thing but just seeing what life is like there now what is it like for people and in particular women I’ve seen that there’s quite a few tour operators who are operating women’s only tours to Afghanistan which intrigues me firstly I know that you can’t get insurance to operate there but anyway that’s not my my place to comment but I’m
Jason Elkins (31:53.797)
No, don’t judge me just yeah, I got you
Lisa Pagotto (31:58.21)
I’m watching, I’m just very, very curious. And there’s a part of Afghanistan called the Wakhan Corridor. That’s the part. It’s like a 21 day hike and it sits between the border of Afghanistan and Tajikistan. So it’s basically hiking through villages. I have this fascination with crumbled villages where life is still really preserved. It’s super traditional, nothing’s been touched and transformed for the sake of tourism. And that just truly authentic, untouched way of life is what really draws me to
to that destination and to that particular corridor because I know how inaccessible it is so it’s got to be amazing.
Jason Elkins (32:34.469)
Right, I imagine it is. And you kind of, you touched on it when we talked about, you know, women and women’s trips and stuff like this. And right before you mentioned that, I was like, I’m gonna ask you the question that I’m not sure I would ask, but I know people ask you, you know, as…
I don’t know if you’ve traveled to these countries with groups, solo, I don’t know, but either way, I know you have people asking you, oh my gosh, you’re a woman, why would you go to these places and must be horrible and are you uncomfortable and are people rude to you and why would you want to go to these places? So just pick one of those questions I know that you’ve been asked a bunch of times and pretend I’m asking it.
Lisa Pagotto (33:15.554)
Yeah, sure. And I mean, the answer to that’s really simple. And it comes back to what we were talking about earlier with perception. In all honesty, those, countries, and I will use Iran, Iraq, and I’m going to use Afghanistan, even though I haven’t been there, I’ll throw Yemen into this mix as well.
You don’t get hassled at all. Like I’m blonde in a lot of these countries you are, you know, wearing a hijab and everything. So that’s hidden, but I still have fair skin. You can tell I’m not local. You get hassled in more in the countries that are developed for tourism. Like I’ve just come back from Egypt. I’ve never been more hassled in my life. Jordan’s the same, you know, it’s built for tourism. They know tourists have dollars. But in these other countries, they’re so, because tourism is so not a thing and it’s so in its infancy stages,
They’re just curious. They don’t want to hassle you. And you know, it’s not a female thing. And I guess that that’s also a bit of a Western lens on how we perceive the Islamic culture with how women are treated. mean, unless you’re Islamic yourself, you don’t really truly understand how that all works. We just see it as oppression, depending on how we want to view it. But in reality, it might be like that more in certain destinations than others. But until you’re there and you can witness it and you can truly
to the locals without the tourist lens. You don’t get that depth and you don’t get that level of insider knowledge and that education and that is why our travellers travel with us because that’s what they want. They don’t want to go to you know the sound and light show at the pyramids and then get hassled to buy scarves so that they can look like that they’re a Bedouin. It’s just such a different style of travel so I have never once in any of those destinations because of being
a female had any kind of security issue at all.
Jason Elkins (35:08.005)
love that and I love that it is the perception thing and I tend to go to places that my family’s not always happy that I choose. And unfortunately even that, that could be Mexico sometimes. I love Mexico. I think it’s amazing place. I think there’s so many cool things to see. Are there issues in places? Yeah, there are and there are in Arizona where my family lives as well. But I think…
of the things I found interesting in my travels is that we have, as somebody from the US, people in the US, not all, in general terms, I’m say we have perceptions, misperceptions about, let’s say a country like Colombia, which is probably my favorite place on the planet. And there’s a lot of people in the US that would never go to Colombia because they have all these misperceptions. I shouldn’t call them misperceptions. I don’t even know if misperceptions is a real word, but.
They have all these ideas in their head of what it might be like and what is so interesting is when I’m in Colombia And I was speaking with Colombians about the United life in the United States Guess what they have just as many miss Perceptions, I don’t know this perception they have so many perceptions based on what they’ve seen on social media and the news and They ask questions like my gosh. It’s really dangerous in the US and what are you guys doing there? Why you know, why do you have these school shootings or these?
Road rage incidents or all these things and and it’s interesting when a Colombian says I’m not going to the US that sounds horrible That sounds terrible terribly dangerous and they forgot all these people in the US like I’m not going to Colombia no way would I ever go there and And once you’ve been to enough places like that you start to realize. maybe it’s kind of the same thing with Afghanistan Maybe it’s the same thing with Iran or Iraq
Lisa Pagotto (36:41.836)
Yeah.
Jason Elkins (37:01.625)
or Pakistan or whatever and the more you find proof that maybe things are not the way we’re being told, it just kind of makes you want to go explore a mine, doesn’t it? It does, it does mean.
Lisa Pagotto (37:13.132)
Yeah, it does.
It’s addictive. know, once you realize that you’re wrong and you’re okay with that because you’re learning and you’re growing as a person from it, you’re like, well, hang on. What else have I, you know, misconstrued in my own mind? Let me, let me keep exploring. Where can I go next to keep learning? Because yeah, maybe the national news at seven o’clock every night hasn’t given me the right perception of XYZ country. Yeah, I know it’s, it’s mind blowing, but it does. It becomes addictive.
Jason Elkins (37:27.525)
What else did I get wrong?
Jason Elkins (37:41.647)
do that.
Lisa Pagotto (37:47.12)
and you just have this hunger for it’s the curiosity it’s insatiable.
Jason Elkins (37:51.301)
It’s also very interesting to me that, because I’m quite familiar with a few places now, I still go to a lot of places I don’t, I wouldn’t say I fully know, but there’s a few places I feel like I kind of know. And one might be an example would be Medellin, Colombia. And, you know, I’ll see in the social media groups, there’s large groups of expats or people that, you know, whatever people that are talking a lot about Colombia.
Many of them have never been, they’re just in these groups lurking, I think. But the common questions you see is like, where should I stay? And then the other, I’m gonna use the term gringos, it doesn’t offend me, it’s just a word. But the other gringos might tell each other, well, you should stay in Poblado. And everybody’s talking about Poblado. Well, most of the tourists stay in Poblado, da-da-da-da-da. All this talk about these areas that are…
where the tourists go or whatever. And interestingly enough, those are also the areas that very clearly are the most dangerous. Yeah. And once you get there and you start to look around, you realize, geez, I think I’m a lot safer up in the barrios in the hills because the…
Lisa Pagotto (38:53.93)
Yeah, they’ve got the crime because the tourism dollars are there.
Jason Elkins (39:08.025)
People up there don’t see, they don’t look at you the same way. If I’m walking around in some of the barrios up in the hills, they’re like, okay, you have a reason to be here, it’s not tourism. If you had a lot of money, you probably wouldn’t be here.
Lisa Pagotto (39:20.419)
Yeah.
Jason Elkins (39:21.217)
And they all know each other. It’s a neighborhood. So they don’t tend to cause problems in their neighborhood. If somebody is going to cause problems, they tend to go where all the rich tourists are, cause the problems. But you wouldn’t know that if you didn’t kind of experience life out and about. I know you’ve come across probably a lot more situations like that than I have. I also suspect you have some, I don’t know. I don’t know if I to, I’m going to ask you this and you can figure out how to answer it.
I suspect you have had over the years some situations with clients where you needed to get somebody out of somewhere in a hurry or I don’t know how much detail we want to go into but.
Lisa Pagotto (39:58.286)
We have.
Yeah, yeah, we have, but more so for medical evacuation, more so than security. Yeah, I mean, we’ve had collapsed lungs in the Borneo jungle that have had to be helivact. We’ve done a gazillion and one helivacs out of Nepal. But in terms of from a security breach, not really. We’ve had not anything that’s been evacuation. We did have clients go into a bunker in Israel a couple of years ago for a day. And we did have
I was actually hosting a tour in Pakistan where we had to re-route our itinerary because there was a specific highway that went under Do Not Travel that we needed to travel on to get to the north of the country and so we changed that and just booked a flight to avoid that. And then we did have a trip, this was pre-pandemic to Iran when it was still relatively safe to travel there where we had to, the tour was in operation and an area fell under Do Not Travel by our government warnings.
and we just had to reroute the journey. The tour continued, but we just had to do an alternate couple of days into a new region. So that’s really kind of the hairiest that we’ve had. But in saying that, it’s so minimal compared to, you know, extreme circumstances that could happen. Yeah, it’s more medical than security in, you know, that we’ve been operating nearly 13 years.
Jason Elkins (41:25.367)
And I suspect with maybe that type of travel, I’m just curious what your thoughts are. I know for me, oftentimes the best memories and best experiences that I’ve had have been when unexpected things come up and maybe even things that feel like at the moment, they feel like, ooh, this is a little bit sketchy. So it could be, you know, getting in a taxi and ending up in a neighborhood and you realize this is not the neighborhood where I think I’m staying. I think we’re lost.
Lisa Pagotto (41:39.959)
Yes.
Jason Elkins (41:55.291)
I’m not communicating very well. And then before you know it, you’re at the taxi driver’s home with his family eating dinner because he didn’t know where to take you. So he took you home with him. I just, kind of made that up. That hasn’t actually happened to me, but that’s the type of thing that usually happens when things don’t go as planned. And I suspect you guys, you probably have those things come up quite often. Anything come up, anything can pop into mind?
Lisa Pagotto (42:16.663)
Yeah, we do.
We do and we certainly intentionally leave an element of flexibility in the way that we build our itineraries to allow for time for things like that that could happen that we know do happen, especially in areas where tourism just isn’t a thing because people are so, so curious and you know the general rule and looking at you know people think why would you travel to these destinations there’s not a lot of infrastructure but those destinations fall under that humanity rule of the the kindness of strangers more so than somewhere where tourism
is at its peak. And so I’m just trying to think of an example. Last year I had a group
What country were we in? We’re in Kazakhstan. We’re in Turkestan, which is a province of Kazakhstan. And it was one of our group members birthdays. And I told our guide, it’s Kim’s birthday today. Can we organize something tonight? He’s like, yep, no problems all over it. And I was the only one that knew what happened. it was unplanned, but it was semi-planned. But he basically had organized for us to go to his family’s home for dinner that night instead of the restaurant that we were meant to be going to.
Jason Elkins (43:21.466)
Mm-hmm.
Lisa Pagotto (43:28.048)
It was in this tiny village with 12 houses and pretty much the entire village were there the backyard was apple orchards and sheep and There were just all these locals and they came because they had never met Australians before they’d met foreigners but not Australians and they were so curious and they all turned up with their baskets of different sweets and things that they’d made and they all had different and they don’t have their homemade rocket fuel that they wanted us all to taste and It was just one of those it was the highlight the
Jason Elkins (43:54.413)
Hahaha!
Lisa Pagotto (43:57.968)
The absolutely loved it and there was just so much food. It was like this banquet. You would think that you were dining at Buckingham Palace or something and we were in the middle of nowhere. The group were like, where are we going? We’ve been driving for like two hours. What is happening? And I was like, apparently this restaurant’s really great and it’s worth the drive. And they’re like, we’re literally in the middle of nowhere. And then it just, it became the highlight and it was just so authentic with what was coming out. You we didn’t plan for the whole little village.
Jason Elkins (44:26.806)
huh.
Lisa Pagotto (44:27.908)
to be there, they just, yeah, they were curious.
Jason Elkins (44:30.503)
As a tour operator, former tour leader, I’m sure you’ve had that experience so many times when one of those things happens that’s either unplanned, completely unplanned, semi-planned, whatever, and it happens and you’re like, my gosh, if I could duplicate this, if I could only make this happen every week, like let’s say you do the same general itinerary every week all summer,
Lisa Pagotto (44:50.572)
Yeah.
Jason Elkins (45:00.697)
There’s certain things that happen you like my gosh if I could make this happen every week We would be like the number one tour operator in the world Because it’s like the most authentic just characters, you know, characters that wander up out of nowhere You know, I remember I had a hot air balloon ride business and I remember this one time
Lisa Pagotto (45:08.695)
Yeah.
Lisa Pagotto (45:13.525)
That’s what it is.
Jason Elkins (45:21.809)
We were out flying. landed in this place and this farmer came out. was so excited to help us. He thought we needed to pump air into the, we were taking the balloon down, letting the air out. He came out with like a bicycle pump. He was going to help us pump the air back into the balloon. And he was so excited. And we explained to him what was going on. This was in Arizona, but it was, he spoke Spanish. I didn’t speak any Spanish. Kind of managed to figure out, you know, and so he helped us pack up the balloon and then he goes over to his truck.
Lisa Pagotto (45:35.598)
that’s sweet.
Jason Elkins (45:51.763)
and it’s full of, it’s like a van, a little minivan, it’s full of watermelons. And he pulls out these watermelons and his machete and starts chopping these watermelons in half and we’re all sitting there eating these watermelons. And this guy was just so much fun. And it was the 4th of July, which is kind of an important day here in the States. And watermelon and 4th of July just go together. And I was just thinking like, this is…
I could not have planned this. Like, I would have spent months finding the right guy with the right personality, make sure you had the watermelons right, everything, like there’s no way I could have planned it. And then you kind of like look over at your guest and you’re like, you have no idea how cool this is. And you’ve probably had that experience everywhere, like a bunch of places, right?
Lisa Pagotto (46:16.01)
Yes.
Lisa Pagotto (46:30.982)
Yeah, yes, yes. Well, I have, yeah, I have one that I’m going to mention because this is going to be a little bit of a controversial one. So, yeah, North Korea. So it’s just so this was in North Korea. This was really, really random. So I had a month in North Korea when we were building our product. This is in 2018. And
Jason Elkins (46:42.223)
good, I love that. This is the one we’re going to turn into a clip. Just kidding.
Lisa Pagotto (46:59.758)
They’ve capped at 5,000 tourists a year and 95 % of that is Chinese. That’s how it was pre-pandemic as I mentioned, the borders not reopened. So to see Caucasian travellers is so foreign and no one makes eye contact with you. You’re so used to going for a walk and being like, morning, hello, you got, annyeong, annyeonghaseyo, whatever, you say hello and you get nothing. You’re just stone-faced, concrete. The guides are like, don’t talk to the locals, they won’t talk back, they don’t understand English, so just don’t bother trying.
like okay challenge accepted good morning but you were just by the point of what I’m about to share with you by the time this happened you were just so used to being ignored and whether it’s because they don’t feel comfortable with you around you don’t you really don’t know I mean North Korea is just such a mind-boggling destination in itself from every possible angle but we went hiking we were hiking in this national park and it was so incredibly beautiful
Jason Elkins (47:32.135)
Yeah.
Lisa Pagotto (47:59.332)
and this was mind-boggling in itself because all you really hear about North Korea is how it’s all grey and dim and smoggy and you know you just kind of imagine like factory type I don’t know horse and cart old-worldly type situations but this National Park was so beautiful it was so clean there was no rubbish anywhere the water was so so blue and so crystal clear the mountains we had the first snow we were there in November it was like being in the Rockies it was so beautiful
And when I show people pictures, they’re like, that’s not North Korea. That could be like Switzerland or whatever. And I’m like, no, no, no, this is North Korea. This is the side that you just, media would never show this. But what happened, we’d done this hike and we were just talking about how beautiful it was. And we came back to our vehicle and I was like, my God, what is that smell? This smells amazing. There was like this barbecue happening.
And our guide said to us, it’s just a family. They’re just cooking some skewers over there. And I went, my god, it smells so good. And she says, why don’t you join them? And I was like, what?
And she goes, go and join them. said, I thought we weren’t allowed to talk to the local people. She goes, well, they won’t understand you, but go and join them. And I said, well, can you come? Can you, you know, we don’t want to just impede on them. Can you translate and explain who we are and that we think that their food smells amazing? Could we just sit with them for a few minutes? I don’t know what she said. Next thing we were handed these skewers and we were sitting there eating wasn’t quite lunch, but an afternoon snack of chicken skewers sitting in this forest in North Korea after having nearly three and a half weeks of
being completely ignored and these people just were normal like everywhere else in the world. You know it was just so unexpected but amazing, super amazing and in the most beautiful setting.
Jason Elkins (49:48.423)
Tour operators try and set those things up, know, I mean you have I know you’ve tried to set that stuff up I know I’ve tried to set that stuff up and It just it’s it’s when you don’t try that it ends up just happening and it’s the most amazing Amazing thing and yeah I am a little bit curious about I think
want to go back a little bit to, you said your parents, you traveled a bit with your parents and when you went North Africa, no you’re not going to North Africa, but you went anyway and then you obviously went into the travel business and kept going to all these places. Were your parents supportive at some point along the way? Like did they think you being a travel agent was a great idea? I’m just curious like how much support and encouragement you got.
Lisa Pagotto (50:44.226)
Yeah, they’re very supportive about my career in the travel industry, not overly supportive about my choice of destinations that I choose to explore. There’s a bit of a…
Jason Elkins (50:49.607)
They’re not happy with your dish, I’m sure I get that.
Lisa Pagotto (50:54.316)
very happy at the success of my business and that sort of thing. But when I’m like, all right, guys, next week, I’m off to go and watch a rocket launch at the Russian Rocket Launch Center in Baikonur in Kazakhstan. Yeah, a few eyebrows are raised, but they’ve stopped questioning because every time I’ve come back, they know that due diligence that we do, it’s just not their cup of tea. And, you know, I’m very aware that what we do is not for everybody. But yes, the overall consensus is they are supportive and they are proud and they are very aware that, you know, the way I was raised.
Jason Elkins (51:03.142)
you
Lisa Pagotto (51:24.33)
was the building blocks for this.
Jason Elkins (51:26.85)
At this I suspect at this point they probably don’t say much But I’m curious, you know earlier on were there places where they other than you know when you’re eight when you’re 18 and they say no you’re not going to North Africa or Before you’re 18. You don’t have a lot of control over that But I’m curious where their points when you’re in your 20s or 30s or you know
just now in your late 30s obviously so but where their point I wouldn’t have known but were there the places that they just like no absolutely you’re not going but you just kind of had to assert that mom dad I’m an adult and yes my it’s important for me and my business to go do something in Kurdistan or whatever do you remember any of those moments
Lisa Pagotto (51:54.023)
I’ll take that as a compliment because I’m not.
Lisa Pagotto (52:14.826)
Yeah, I do one in particular. So this is before Crooked Compass. This was at, I mentioned to you that I went overseas for a second time and it was for a two year stint. So this was at the very start of that trip. I had planned to have two months backpacking through Syria, Israel, Jordan and Lebanon. And at this point, this was 2008 and Lebanon was in a bit of a fiery situation. And my dad said, absolutely not. You need to cancel those flights. You are not going to that region. And I was like, well,
Jason Elkins (52:25.255)
Hmm?
Lisa Pagotto (52:44.98)
I’m really fascinated by this part of the world. So I’m going. Nothing’s going to happen. I’m all registered with the government. They can track where I am. I’ve registered all my accommodation. Didn’t have mobile phones back then, so I wasn’t traveling with a phone. You still had to go to an internet cafe to tell people where you were. And I went. I had two months backpacking, literally myself and a girlfriend. We started in Jordan, went into Israel, came back through Jordan, up into Syria, and then finished in Lebanon.
Lebanon there were tanks in the street the airport got shut the borders got shut we were under hotel lockdown for a week in Beirut and we had internet there was a computer in the hotel lobby and so I would email my dad all’s good we’ve got a rooftop pool here it’s fine the hotels look it was just wasn’t it was a non-issue despite what was going on in the media and then everything reopened and I took my flight to I think I was actually going to Italy next so that was one of
Jason Elkins (53:43.111)
Did you for a moment on that trip, just curious, they, geez, maybe Dad was right. good for you.
Lisa Pagotto (53:44.59)
those moments.
Lisa Pagotto (53:52.982)
No. No, I didn’t. I was…
My biggest concern was I’ve missed my flight out of Beirut because the airport was shut. But then at the same time, because I’d had the experience of working in the travel industry, I kind of understood how it worked. And I was like, well, if the airport’s shut, it’s no one’s fault. Like the airline will need to reshuffle people around. So that was really my biggest concern. We were treated like queens when we were in that hotel arrest. Obviously, it wasn’t an unfamiliar situation for the local people, and especially being in the hospitality space of a hotel.
their number one thing is to look after their guests and so you know as a early someone in their early 20s being on a rooftop pool for a week and it was the middle of summer as well so it’s like 50 degrees it was perfect
Jason Elkins (54:39.943)
It’s a lot worse than getting stuck in a snowstorm in Chicago or Detroit for a week or something when they shut down the airport. Yeah, yeah, absolutely. that’s pretty fun. Was there?
Lisa Pagotto (54:44.778)
Exactly, exactly.
Jason Elkins (54:52.365)
So when you’re working for somebody else, you said you’re helping them build their business. And I would love to just real quick hear about, you know, your decision to launch Crooked Compass. What was behind that? And maybe one or two takeaways that we could share with our listeners who maybe, you know, are thinking about getting into travel or thinking about maybe they’re working for somebody else. You know, they’re they’re an advisor on a tour operators team or something like that. And they’ve been thinking they want to go do something
their own just you know just in case they’re listening what would you like to say
Lisa Pagotto (55:23.502)
Thank
Yeah, absolutely. the way that that light bulb moment came about was I was working for an adventure tour operator who actually went bust and I was then contacted, I lost my job and I was contacted by the owner of another tour company who said, hey, I’ve seen what you’ve done at this company. We would like to bring you over to our company because we specialize in battlefields as in like the Western front, Gallipoli, those sorts of things. And we can see that our business is going to plateau when it hits
2015, the centenary of the Australians landing at Gallipoli. So we would like to create another brand so that we have a new revenue stream as that business sort of hits its peak. Can you bring your contacts? Is this something you’d be interested in doing? And I was like, yeah, absolutely. This would be fantastic. I can literally pull all of my skills together and yeah, build you a new brand. So I did that. I spent 18 months building a new brand of 42 different tours for somebody else. And at the same time, I’d started a blog in the
I’ve always written every time I travel even now I still keep a travel journey. It’s still manual with a pen But I’d started to put it onto a website onto a blog and this was just this is 2013 just when blogging was starting to become a way of influencing people and it was called crooked compass and it was me writing about all these weird wonderful travel experiences that I had had that weren’t normal for someone of my age and It just grew a following really really quickly and I was like, oh interesting
And then people would start to comment. my god. How did you find out about this? How can how can I travel like you and so my mind started going? Okay? Well, how can I commercialize this? How can I turn this into a business? And so I went down the path of should I sell advertising on my blog? That’s a bit yeah, don’t really want to be wasting my time trying to get advertisers and sponsors pass Then it went to maybe I should write an e-book about you know a hundred unique experiences that you can’t find on Google and I thought yes, that’s it
Lisa Pagotto (57:25.366)
I can do that nine dollars ninety nine everyone will want it I had a mentor at the time and he was like no one reads ebooks anymore Why don’t you create an app and I said I know nothing about tech. I don’t know anything and he said I’ll just speak to a few developers share your ideas and basically that evolved into a thousand individual outside-the-box experiences that you couldn’t find on Google and so I did I built an app and Sold sold my house to be able to fund it because I didn’t have the money at that age to be able to do
and just backed myself that I could turn this into something. And it took six, seven months for the app to be built and then another six months for all the content to be loaded. I’d been writing it while it was being built and it launched and in its first six weeks it went into the top 100 travel apps. And initially I had it as a $1.99 to download and I had this light bulb moment of I was still working for this other company at the time where the guy next to me I said, have you got my app? Have you got my app? Have you got the Crooked Cup app?
and he literally slid a two dollar coin across the table to me he goes I don’t know what my password is for my my apple account so just tap the two dollars and I was like no it’s not about the two dollars and when I realized that that was a barrier for someone that I knew I thought well this is going to be a barrier for people that I don’t know so what if I pull the price tag off it and I made it free and it just skyrocketed there was so much PR floating around about it at the time and that was basically the basis of it and you could send inquiries through the app
and then that started the bones of what became Crooked Compass. yes, and then I started off with six small group tours and then it went from there. You’re on mute.
Jason Elkins (59:12.379)
Yeah, I saying yeah, I did I muted myself because there were trucks driving by in the background listening to that and and you were saying that’s how it started and I said and here we are so that’s That’s very very cool Congrats
Lisa Pagotto (59:21.23)
Here we are nearly 13 years later. So in terms of takeaways for people who might be listening, if you have an idea, just back yourself. Don’t wait for someone to tell you, now’s the right time or you need permission or yes, yes, you can do this now. Like if you feel something in your gut and you really, really believe in something, you will find a way to make it work. And don’t have a plan B. Plan B is a distraction. It’s a full black plan. Like if you really want something, that is the only option. And then you will put everything
Jason Elkins (59:28.07)
Yeah.
Lisa Pagotto (59:51.214)
in to making it work.
Jason Elkins (59:53.711)
I’m sure you maybe have heard the story. The story I’ve heard anyway. I don’t know if there’s any truth to it at all, but when the Spanish led by Cortez were somewhere off the coast of Latin America, I won’t give details because I’m sure my details are wrong, but at some point they were going to take the island and they pulled up and got off the ships and then he turned to his men and said, burn the ships. And because if you burn the ships, then there were no other option. We were either going to take the island or we were going to die trying because
There was no retreat, there was no plan B. So I’ve heard many times that term is like, give advice, okay, burn the ships. That’s the biggest piece of advice I can give you is burn the ships, get rid of your plan B, sell your house to pay for the app, whatever, that type of thing. And if I was to run every episode of this podcast through AI and pull out the common threads, that’s gonna be a big one.
Lisa Pagotto (01:00:25.815)
Yes.
Lisa Pagotto (01:00:51.979)
Interesting.
Jason Elkins (01:00:53.385)
to people on the show is it’s that ability to just take action without knowing what the outcome is going to be. And I suspect there’s an awful lot of people that think, oh, I would love to work in tourism someday. I would love to have my own tour operation business someday. But I have to do this first. I have to do that first. I have to do this first. And the ones that most of the people that have been on the show have been people that have been successful doing it. And I’ve heard the story.
Lisa Pagotto (01:00:59.864)
back yourself.
Jason Elkins (01:01:23.375)
times it’s like take action do it you know invest in yourself and just just decide you’re gonna do it and get rid of the other plans so great advice and I hope that
Lisa Pagotto (01:01:31.426)
Yeah.
Jason Elkins (01:01:37.639)
I hope people will listen to enough of these conversations that they will start to believe it. If this one conversation with Lisa is not enough to get you to believe it, listen to a couple more, you’re gonna hear, because what she’s saying is the truth. That is the trend. If you wanna be successful in this business, you gotta be able to just do some crazy stuff and just go to Tunisia.
Lisa Pagotto (01:01:59.662)
Take the trip.
Jason Elkins (01:02:00.187)
Regardless of what your parents are telling you. anyway, at least a lot of great stuff. We discussed a bunch of stuff and I want to be respectful of your time as well as the audience. But I’m curious, like what did I forget to ask you? What do wish I would have asked you? Or what do you think, is there anything else you’d like to share with our audience either about you, Crooked Compass, life in general? Before we wrap.
Lisa Pagotto (01:02:24.674)
We’ve covered a fair bit. guess I would probably just add to what we were just talking about, about backing yourself. And, you know, that’s one of the most common things that people say to me is I wish I could do what you do. And I think that another way of looking at it is reversing that situation into what is the worst that could happen? What is the worst that could happen? I could lose my business. You know, I almost lost it when our board is shut for two and a half years with the global pandemic, but we’re still here. You know, what is the worst that could happen if I lost my
business, I’m not unemployable, I can get another job and I probably have built a very unique skill set because I have had to be the jack of all trades in my own business that you couldn’t find if you were trying to recruit for it. So what you learn when you back yourself and when you believe that you can, even if you’re just doing one tiny step every week, it doesn’t have to be all in straight away. You can chip away at it. know, not everybody has the ability to sell their house.
extreme and I was very fortunate to have had a supportive husband to be able to do that at the time but think about what is the worst that could happen what is that thing that’s holding you back what is the worst that could happen and is it really that bad that’s probably the last thing that I would add
Jason Elkins (01:03:40.465)
Yeah, and I’m sure there’s people out there listening saying, Lisa, you have no idea how bad it could be if I lost my job or if I lost my house. I get that, so we get to be sensitive to that. But there’s also a lot of people sitting there that are in the position. They just don’t realize it. They don’t realize that, wow, I actually do.
Lisa Pagotto (01:03:51.895)
Of course.
Jason Elkins (01:04:02.855)
a supporting family, a supporting spouse, some money in the bank or skills, like you said. And that’s a huge thing. And part of why you have those skills is because you took risks and took chances early on.
Lisa Pagotto (01:04:15.554)
Yeah, yep exactly and that’s not something that can be taught. You can’t teach someone that. You’ve got to have it in you.
Jason Elkins (01:04:22.074)
exactly so
Thank you so much. This has been a fascinating conversation. Really appreciate you coming on and sharing your story and hopefully inspiring somebody either to go somewhere to question that perception that maybe they’ve been carrying around with them or their families are carrying around with them. Go do something, go make this big world feel a bit smaller. Cause that’s, there’s a reason that I aimed the podcast is because I want that to be the case. And I think you’ve, you’ve helped make that happen. So Lisa, thank you so much. I appreciate you for joining us.
Lisa Pagotto (01:04:53.91)
No problems, thanks so much for having me, Jason. See you.
Jason Elkins (01:04:56.081)
Talk to you soon.
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