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Authentic Leadership in Business with Lisa Pagotto, Founder of Crooked Compass

25m 36s

Authentic Leadership in Business with Lisa Pagotto, Founder of Crooked Compass

Lisa Pagoto, founder of Crooked Compass, recounts her entrepreneurial journey marked by a near-catastrophic failure and a successful pivot. After appearing on Shark Tank Australia, she didn’t secure an investment on the show but later struck a deal with a shark post-filming. Blinded by the allure of media attention, she agreed to terms that led her business into administration when the deal collapsed unexpectedly via an email she wasn’t meant to see. This occurred just before she became a mother through adoption, giving her a fierce determination to save the company. A guardian angel investor, moved by Lisa’s story at an International Women’s Day event, provided the funds needed to clear debt and remove the shark from the business. When the pandemic hit, Lisa used government jobkeeper payments to learn to fly, which exposed her to private aviation. She pivoted to “Crooked Compass by Air,” offering private air tours within Australia using charter planes, saving the business. She rebuilt from first principles, returning to her original why—taking people to remote, obscure destinations with high-touch, premium service. Her leadership now emphasizes alignment with core values, radical transparency about travel realities (including worst-case scenarios), and investing in team firsthand experience to deliver authentic, credible travel. This authenticity and human connection, she believes, cannot be replaced by AI and is key to the company’s continued success.

Transcription

4733 Words, 25196 Characters

English
[Music] All right, hello and welcome to another expert inside interview. My name is John Golden from Salespop, online Sales Magazine and Pipeline or CRM, joining you as usual from a sunny, actually a bit of a heat wave, San Diego today. And I'm delighted to be joined from down under from Australia, and lovely Sydney by Lisa, and Pagato, how are you, and Lisa? I'm good, thanks John, how are you? Yeah, and I've given up with that stupid joke about, oh, give me the lottery numbers, because you're a day ahead of me. You're a darling in from the future. So, Lisa, you're the founder and CEO of Crooked Compass, a multi-seven figure immersive travel company, specializing in small group, culturally deep expeditions for emotion, extraordinary destinations. And you were on Shark Tank, Australia, and you pitched your vision for authentic community connected travel, and then you built the business from the ground up, then the global pandemic hit, right? And you had to make some big high stakes decisions, including a major pivot, and they could have derailed everything. But instead, a folding you rebuilt from first principles launched Crooked Compass by Air, later evolving into Adventure by Air, and emerged stronger with a reshape leadership philosophy. And that's what we want to talk about today is, is that, so let's start off, when you appeared on Shark Tank, you know, and you were chasing growth for Crooked Compass, looking back, and what was the most consequential, yes, you had said in the years that followed, and why did it turn out to be catastrophic? In the years that followed. So, for me, my Shark Tank journey, I didn't get investment on the show. My business was in a very unique position where it was the only business in the history of Australian Shark Tank that was able to film a follow-up a couple of years later. Usually, they only choose the businesses that have had the investment. But the reason that I was able to do that was offset myself and one of the sharks. We struck up this incredible relationship, and we got into a deal post-filming. And this is probably, there was just some incredible learnings from this time, where I was very much caught up in the start of having a shark interested in me and my business, and the exposure that they could give me that I was just, I kind of had blinkers on. And I was just in this tunnel vision mode of not being able to see anything, but wanting to do what this shark wanted me to do. And I ended up agreeing to things that effectively, yeah, I mean, I was very lucky, but I ended up getting myself into a point where I was just so obsessed with wanting this media attention, and all of this, um, slushiness that came with it, that I ended up getting my own business into administration, because I just lost track of what my business was about, who I was, why I started it. And I was just shiny penny syndrome. I was taken off over here away from the focus of what I did, what I did. So what was that like when you suddenly were faced of administration, and you were suddenly going, oh no, I've been, I've been blinded by the glitz and rather than the business, uh, for the moment, what was that moment like for you? I mean, obviously it wasn't like it didn't happen like in one second, but what was that gradual, probably realization? Actually, it did happen in one second. Oh, it did. It ended with an email that I wasn't meant to receive, basically saying, this is not happening and someone let her know. And it was literally the rug being pulled out. I had literally signed on seven new staff members. We were in full scale mode and I did not have the cash to be able to facilitate that. This was all part of this deal. And so it was an instantaneous. Wow. Holy, I'm not sure if I'm allowed to swear, but holy moly moly. And that feeling it was a mixture of, I need to vomit right now. What have I done? I've got this so wrong covered with all of the sweats and the goose bumps and just that lump in your throat. All of those reactions in an instant and going, I can't trade out of this. I cannot trade out of this. What do I do? And that was all of those things happening in what felt like a micro second. Yeah. So when was it like, so you received an email that you weren't supposed to get? So you weren't supposed to know this immediately, you know, that they were pulling out and that. So obviously that was massive shock. And how, what did it take or how did you manage to kind of pull yourself together? Because that's face it. I mean, in a situation like that, a lot of people would just gone to pieces completely or maybe just thrown in the towel or maybe even just gone into poor pity me mode and like just retreated from the world. How did you, how did you pull yourself out of that? Yeah. And it's really interesting. I'm looking at that South Korean flag behind you on the wall. So when this happened, this was one week before I was about to become a mum for the first time. And I was adopting my son from South Korea. And I think if I wasn't in that position, I probably would have been one of those people that just went, you know what? This is, this is the card, you know, most, I was the business was only three years after this point. Most don't make it to five years as a small business. I possibly, I don't know, but I possibly would have gone, you know what? It's just not worth the fight. But because I was about to become a mother, there was just this fierceness of, I'm the bread winner in my family, you know, my husband at the time he was taking a year off to be the state home, while our son settled. And so it wasn't an option to allow that to be an option. And so I, I mean, it took a long time. It took about six months, but I literally tried every possible avenue that I could to get finance to I applied for every possible zero interest credit card. I spoke to my accountant every possible bank and just no one would touch the business because travel the travel industry is so volatile and the business was so young. And it wasn't until it was international women's day. So good couple of months later. And there was this lady hosting a session and she said, I would love all of you to write down someone who you would love to meet that you've never had the courage to introduce yourself to. And I put down her name. I'd met her very early in my career and she said, would anyone like to share? And I said, yes, I will. And I put my hand up and I watched the front of the room and I gave her my business card. And she kind of looked at me like what? Okay. Anyway, what ended up happening was two weeks later, I ended up having a lunch with her and I told her she said, okay, I've heard of crooked compass, but who are you? What's your background? What's your career? I told her, told her everything. I told her the shark tank story, the position I was in and she said she just paused and she said, what is the figure that you need? And I said, what are you talking about? And she said, what is the figure that you need to clear that debt and to get that shark away from your business? And I said, oh, it's roughly X. And she goes, I need a firm figure. Can you get it for me? And I said, yeah, I can get it for you this afternoon from my accountant. Why? And she said, give me your company bank details right now. I have believed in you from the moment you have opened your mouth and I'm in a position to help. Wow. And that guardian angel moment. Yeah. Yeah. So basically the rug pulled on to you in an instant and then almost an instant. And in instantaneous, like suddenly you get this in that moment, it's also it's all it's all it's all it's a good back to the flag. It's the umyang. It's the in and young. Yeah, yeah, it really is. And it's just, you know, I'm still speechless to this day about she didn't even know who I was. Right, right. Like that kindness of straighters and we're not talking $50. Yeah, no, no, I clearly clearly clearly. I think part of it is what you just said there, I think it's really interesting because sometimes I think when when issues come up with business, whether it's your own business or the busy working one is you don't have a really powerful why and a purpose because the powerful why and the purpose will drive you just like you said, I'm about to become a mom, I don't have a choice here. I've got to do something and that why and that purpose gave you the energy and I think that's probably sometimes what what people lack when they get into a situation like this is they've never asked themselves why and what is the purpose of this and why why do I even want to do it. Exactly. And then if you flip the card on that, that's how I got myself into that right in the first place because I deviated from my purpose and from my why I lost track of it and I nearly lost everything because of losing that focus. No, it's such a great, it's such a great story. And then tell me about so you so obviously the pandemic and all of that and tell me about, you know, tell me about the pivot you made because I think people, people love to hear about pivots. And pivots are things that are so, you know, they're so difficult in one way because you have to decide am I pivoting completely am I pivoting somewhat am I going to am I am I okay with you know abandoning what I'm doing now or you know, even I've invested all this time and energy or whatever I'm going over here. I mean, that is also a very hard thing for people to make a decision on. Yeah, it really is and the pandemic was something that you know hopefully none of us ever have to experience again in our lifetime where particularly in the travel and tourism industry every possible channel that you could consider was closing in front of you especially here in Australia you know we had one of the tie to lockdowns in the world and so you know for us originally with with the crooked compass brand we launched domestic touring product and it sold out within a week of launching it and I thought wow okay well we can survive we can survive with this but then our state board has started shutting we could not break any of them and I'm going well what do we do we're Australians stuck in Australia and we can't even travel in our own country no one's interested in traveling within their own state like and then we got locked down and we couldn't even leave our own homes and so for me I'm that person where my brain just constantly needs to have something stimulating it and having literally nothing everything was in reverse refunds cancellations it was just there has to be something there has to be something there has to be something and our government gave us what we called jobkeeper which was effectively a percentage of your salary for yourself and any employees to try and keep business business whilst we couldn't trade and I decided that I would use mine to learn to fly I needed something that would stimulate my brain because nothing else was at the moment and being surrounded by negativity is not yeah it does not offer creativity or anything like that and so despite everybody telling me that I was insane wanting to use that money to do one of the world's most expensive hobbies yeah what ended up happening was I was exposed to this private aviation part of our industry that I had no experience in right and charter planes were still allowed to fly commercial flights weren't but charter was and so my brain suddenly kicked into gear and went you know what we can do private touring around Australia with charter aircraft and so that was where the crooked compass by air brand came from and that is what saved the entire business and so that's what we did we we did private air tours taking people from wherever we could use regional airports as well so it brought in our scope to some of the most beautiful remote luxury lodges but even cattle stations as well and that's what saved us and we could do that state by state because everyone had different restrictions but because of the price tag attached to that product and the business wound back to just being me the overheads were so low but there was enough for it to help reveal the business and to keep it going so that was that was the COVID pivot that came about because everybody told me I was crazy now that's fantastic actually I have to say because you know I've been to Australia a load of times but I've never been to like the interior you know and the really it sounds fantastic I'd love to do that to take a flight into somewhere like even the cattle stations would be awesome yeah the other side of things and you say also by the way anyone watching Australia has a federal government system so their states are you know have certain amount of autonomy so you can that's how they could close everything down like that and restrict internal travel etc you said you built from first you built from first principles what what were the first principles you used to rebuild the business I used the same principles that I used right back at the beginning when I started Crippet Compass and for myself and for it all had to be with it start with why it had to have a why and that why was taking people to remote and obscure destinations and we could do that in Australia because having child aircraft we could go so remote we can land on brass strips dirt strips we could take people to places that weren't what you find on Google and so it was it all followed the same philosophy and the same values as the Crippet Compass business where it had to be high-touch it had to be a high price point a premium price point I should say and it had to be service the service from both you know customer service but the delivery of the product itself and those three when they're combined together they work so beautifully and they deliver something premium that you know people value in terms of what they're paying for and what we offer across both brands even still today um things that you just can't do yourself you can't figure it out Australia is so big and is so broad and whilst there's no language barrier um you know the the language is so read me well it depends what state you're in yeah yeah Sydney science should be able to understand Queensland maybe a bit different yeah no I love I'm a jerk I love the Australian accent and seniors I think Ireland had a little part in in the evolution of that accent too so yeah it's all our rebels all our rebels in convicts um but it was there any um was there any like beliefs or assumptions or things that you had to let go of that may be from before that you had to let go of for this for to in order for this success to manifest yeah I I have to basically relearn to be me and to go back to trying to you know hang on the co-tails of a celebrity effectively and and leverage off that I had to go back to it all came back to why why did I want to start it and why me why would I be the person that runs this business and what I've really learned through all of the the rollercoaster journey of this is if I just stick to what I did when I very first started this business 12 years ago that was trusting my gut knowing that the experience that I've had in my career that's allowed me to get to this point is what made the business successful before I went on Shark Tank like Shark Tank obviously you know we had the TV exposure and salt made it boom yeah but after everything that came back to what I went back to the values that it started at and they still continue now 12 years down the track and that is why the business continues to flourish because we stick with that why we stick with that purpose and it's me just being me it's you know you see that coming through the brand you see it coming through the communications we're not trying to be the world's biggest premium adventure brand we want niche high-touch experiential curiosity stimulating travel experiences and that's the comfort manufacturing something it comes from being truly authentic yeah and it's such a good point because I think and if you think about the pandemic I mean it was happening before the pandemic but the pandemic accentuated it and now and now with AI and everything is that that authenticity and that connection with with real people who have you know who have real you know passions and purpose and everything that's be that is becoming more and more I think what people crave because we live in a world because we had that shut down lockdown and then we live in a world where nobody knows what's real anymore I think the authentic leadership and and connecting with companies who have authentic leaders or people in the business I think that's a massive competitive differentiator going forward I completely agree and I know that you know even if we just look at the past 18 months everybody did get caught caught up in the AI flurry and how exciting and how powerful it is but it really depends on your business model and because the destinations that we operate in obscure their stigmatized their controversial people want to speak to a human they don't want a bot replying to them they want to know that they're getting accurate information because someone's personally been there and so that human touch element that we offer that has to come with the style of product that we offer it can never be replaced with AI yeah we can use it to improve processes and systems but that human touch that builds trust and connection and that demonstrates value that can't be replaced in our style of business by AI yeah and what would you say now is your is is the leadership the leadership strategies or characteristics that you that you really believe that you that you epitomize if you like and that really drive your business forward yeah absolutely so there's probably three that are the main ones the first one is alignment it has to align it has to align with what my values as the founder it has to align with why we started the business in the first place and it has to align with what we're wanting to deliver with to the communities that we work with which is obviously sustainable income and not changing things for the sake of tourism right so that means it has to be small low scale that's how it has to be we're not interested in having departures every Tuesday and what that does to a community that's so not our thing the second one is about being really transparent I often say that we over service and we are often over transparent we go to the point of telling people the worst case scenarios because some of the destinations for example papanigini is one of our top selling destinations you have to manage expectations it's not like going to feature right so we will talk about how rougher it is tires getting punctured probably once a week no hot water we talk about all of the worst case scenario things to manage expectations in advance and our travellers respect that because we're not trying to hide something we're not just showing the beautiful tribal pictures we're talking about the reality because we know if we don't we're going to be dealing with all sorts of complaints and our we we have to be honest with ourselves that our style of travel is not for everybody we're not a smart at brand and we don't want to be and so we shouldn't pretend to be so that's the second one and then the third one is just being the best at what we do we know because we go you know the destinations that we sell most people don't even know where they are on a map let alone how to talk about them from firsthand experience so that investment in getting the team to go and experience to be able to talk from first experience about, you know, the quirks and the nuances that come with these this style of travel, that is why people keep coming to us because they're choosing destinations that Google or AI can't give you accurate information. They want to know that true touch point of what it's like over there and we can only deliver that if we've been there ourselves and can talk truthfully, not textbook trained. And as you mentioned earlier, I mean your relationships with the communities and the destinations you go to is obviously critical because you know, let's face it, I mean there's there's probably plenty of other people out there who would exploit that. But that obviously is key to the experience that your travelers have is that you have that good you have that good relationship with the communities that you that you bring them to. Yeah absolutely and I mean just to give you an example of that, one of the two is that we operate in Mongolia is with the reindeer tribes of Mongolia. Now this tribe is a fragile, it's a diminishing tribe, there's only 200 people left in the world in this tribe and it takes us seven days to reach them because they are so remote. But the government is protective of them. They only allow 20 permits a year per company. So we have 20, I think we're one of two companies in Australia that have these permits. But to obtain those, it's about what you do to support this community. It's not about I want access because these guys are really interesting and we'll get some great photos and content. No, this is a fragile tribe, it's a diminishing culture. So we send over 12 dentists a year that we fund to go and look after this remote tribe. Their number one cause of death is Septusemium because their forages, they crack nuts and things with their teeth and they get gum infections. And so you know, they don't even use currency. So taking into less dollars doesn't benefit them. They're a bar to have community still today. And so the thing that we can do to help them is to help their health because they don't have vehicles, they have reindeer as their transportation mode. And so those sort of initiatives is how we do what we do and how we continue to grow and to show that we make a positive impact. We're not taking in masses of people to see if we take 20 a year maximum. - Yeah. - Loathe how tiny that. - Unfortunately, they don't have the flying reindeer's doing. - No, no, no, no, no. (indistinct) They are further north, they say these forest reindeer. - Absolutely, well listen Lisa, this has been fascinating. If there was one last piece of advice you would give to somebody who maybe is, their businesses and going well, they're facing into struggles, they may be starting to doubt their own like abilities and all that, well, what would be the one piece of advice you'd give them? My one piece of advice would be go back to where you started. Just take a total pause and it's okay to pause. You don't have to keep peddling underwater and hope that it's all gonna stick. Just take that breathing space to reflect on why you started and are you still there? Have you deviated? Have you, you know, been distracted like I was? Have you lost that connection as to why you started to do what you did? And nine times out of 10, it's something along those lines. You've lost that connection to your purpose as to why you started to build it. That would be my number one piece of advice. Take the time to pause and really, really reflect on where you're at, why you started and where you're wanting to go and is that in alignment? - Yeah, and to do that, you probably need to dig out some space and time that's quiet and not like distracted and actually, because I think that's the other thing too, is I think sometimes people allow the whole world and all the noise to be in. They don't give themselves the time to think and reflect. - Yeah, absolutely. And other people's opinions, you know, they're not in the weeds with you. They're not running the business with you. It's just an opinion and I completely agree, John, to take that time just to give you an example, literally last week, I have three hours lying on a bat in the bush alone, just so I had no phone, no distractions, no team members, no one else's voice except my own. And I just lay there, watch the clouds, whatever, I just needed space, the decisions that, you know, need to be made in the business without everybody else's noise. - Yes. - And that time in that space is so precious and it's so rare. - Yeah. - But remove the digital devices, they're the worst. - Yeah, yeah, absolutely. And even if it's just like getting up and going out for a walk, you know, don't listen to your phone, don't look at your phone. - And like, it's really amazing. - Listen to nature. Yeah, exactly. Well, this has been fantastic. God of Least's information to be below this video. But before we go, please do remind people about what you do. - Sure. So I've got the two tutoring brands. Crooked Compass is our small group and private tours to your more stigmatized, controversial, controversial frontier and remote destinations internationally. And Crooked Compass by Air is our private air chart is around Australia, taking you to the most remote and luxurious properties within the country all in your own private air craft. - Absolutely fantastic. Well, hopefully maybe one day. So listen there. Thanks again, Lisa. Thank you for watching and listening. I'll see you all again very soon. Thank you. - Thanks so much, John. (upbeat music)

Podcast Summary

Key Points:

  1. Lisa Pagoto, founder of Crooked Compass, nearly lost her business after a post-Shark Tank deal fell through, leading to administration.
  2. A guardian angel investor rescued the company on International Women’s Day, allowing Lisa to clear debt and regain control.
  3. During the pandemic, Lisa used government support to learn to fly, leading to the pivot “Crooked Compass by Air” using charter planes for domestic private air tours.
  4. The pivot saved the business by tapping into a niche, high-touch, premium travel market within Australia.
  5. Lisa rebuilt the business using first principles
  6. Key leadership strategies include alignment with founder values, radical transparency about travel realities, and investing in firsthand team experience for credibility.

Summary:

Lisa Pagoto, founder of Crooked Compass, recounts her entrepreneurial journey marked by a near-catastrophic failure and a successful pivot. After appearing on Shark Tank Australia, she didn’t secure an investment on the show but later struck a deal with a shark post-filming. Blinded by the allure of media attention, she agreed to terms that led her business into administration when the deal collapsed unexpectedly via an email she wasn’t meant to see.

This occurred just before she became a mother through adoption, giving her a fierce determination to save the company. A guardian angel investor, moved by Lisa’s story at an International Women’s Day event, provided the funds needed to clear debt and remove the shark from the business. When the pandemic hit, Lisa used government jobkeeper payments to learn to fly, which exposed her to private aviation.

She pivoted to “Crooked Compass by Air,” offering private air tours within Australia using charter planes, saving the business. She rebuilt from first principles, returning to her original why—taking people to remote, obscure destinations with high-touch, premium service. Her leadership now emphasizes alignment with core values, radical transparency about travel realities (including worst-case scenarios), and investing in team firsthand experience to deliver authentic, credible travel.

This authenticity and human connection, she believes, cannot be replaced by AI and is key to the company’s continued success.

FAQs

Lisa didn't get investment on the show, but struck a deal with a shark post-filming. She became obsessed with the media attention, lost focus on her business, and ended up putting Crooked Compass into administration.

She received an email by mistake, learning the deal was off. She felt shock and panic, as she had already signed seven new staff and couldn't trade out of the debt, but her impending motherhood gave her the determination to fight.

She sought financing everywhere but was rejected until a woman she met at an International Women's Day event offered to personally lend her the exact amount needed to clear the debt and remove the shark from her business.

Lisa used government jobkeeper funds to learn to fly, which exposed her to private aviation. She launched Crooked Compass by Air, offering private air tours around Australia using charter planes, which saved the business.

She returned to starting with why: taking people to remote, obscure destinations. The business remained high-touch, premium-priced, and service-focused, following the same philosophy as the original brand.

She had to stop relying on celebrity association and instead trust her gut and the experience that made the business successful before Shark Tank, sticking to her core values and authenticity.

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