Shaina Shiwarski, Legends

[00:00:55] Sanjay Parekh: Shaina Shiwarski knew the drill. Friends would ask her questions about an upcoming trip and a lengthy WhatsApp exchange would follow. She knew there had to be a better way to share ideas and create friendships across the globe. Shaina founded Legends, a private community of global travelers inspired by each others’ experiences, that seeks to put the traveler first. Here to talk about her story, Legends’ growth, and how she balances her life is Shaina Shiwarski. Shaina, welcome to the show! I'm super excited to have you on.

[00:01:25] Shaina Shiwarski: Thank you so much. I'm super excited to be here.

[00:01:28] Sanjay Parekh: So, I would love for you to tell me and our listeners a little bit about your background first and kind of what got you to this point right here in life.

[00:01:36] Shaina Shiwarski: Yeah, I think it's a great question. So, I think when I look back at my background, I tend to look back at my childhood, and I would spend hours if not nights building 1500 to thousand-piece puzzles. And I would try to figure out how quickly I could build them. And I wanted to complete them all in one night and I loved it.

I would sit in my basement and just build them and then I would frame them and I would give them to people as gifts. And so why I look back on that is, thinking about really what I love. I love to solve problems. I love to look at trends. I love to look at commonalities or patterns and be able to say, okay, this is not just a one-off thing, but this is a pattern that is happening.

And how do we solve a problem around that? And how do we create solutions around that? And so, I went to university and studied. I also was very connected to nature and to being outside as a kid. And so, I ended up studying sustainability and environmental sciences with business in college and I really wanted to do something in that space, but at the time, no one was really doing anything transformative in the energy world yet.

There were some consulting agencies that were doing stuff but not to the place of where it is now. So, I figured going to a consulting company out of college and being able to, you know, take my problem-solving skills, but also get exposure to energy projects as well as financial projects, being in New York, would solve some of the things that maybe I enjoyed as a child.

And what I quickly learned in that process was, you know, being in New York, I got put on a lot of technology bank projects and I learned corporate world in finance was not the route for me. Extremely structured, extremely process driven, very little innovation. Like it is the process because it's the process.

But what I learned is I still love solving problems and consulting was something that really brought that out in me. And so, I got the opportunity to, in New York when the startup scene was just kind of getting started, start at an early-stage series A startup to help build, you know, a company and a product in the go-to-market team.

And so, for the last 10 years you know, it was the first company when I went to that startup where I actually was excited to wake up to work the next day. And I think looking at my parents, and looking at their generation and seeing how they looked at a job as, you know, stability and this ladder that you had to climb.

But every day they weren't excited by the things that they did, right? They were excited to provide for their family, but not solve the problems. Was something that I wanted to wake up and do every day. And so, for me, that is what building, you know, a company is and building a startup in entrepreneurs.

And so that led me down a path of two startups that I worked up for the last 10 years. And ultimately said, you know, you learn a lot. I want to do this related to something I'm passionate about, and so now with Legends, I'm bringing in that sustainability energy aspect of the earth and the environment in travel and exploration, which has been in my DNA from a child of exploring, with the mix of my experience in tech.

And so, I think if you would've told me, this is where I'd end up as a child I probably wouldn't know, but it makes total sense when I look back at it.

[00:05:09] Sanjay Parekh: Yeah, okay. So, in that kind of landscape, it sounds like there wasn't any kind of entrepreneurship in the family. Are you the first in the family? What was your first entrepreneurial experience? Was it doing these startups? Or did you do something as a kid that now looking back on it and like, oh, I was an entrepreneur and didn't even realize it.

[00:05:28] Shaina Shiwarski: Yeah. I mean I definitely think I, if there was in, in my, I look back at even, you know, from a kid to in college, like if there was a product that I really was passionate about, I would be the promoter to all of my friends, right?

Like I would find, because I think of this ability to see trends before other people. And I do bring it back to like the puzzles and just my ability to observe things. I can, one of my, I think, superpowers is I can observe things really strategically and then come really tactically and then go back to strategic and then tactical.

And I think I can go big picture really easily. And I think that I was always an entrepreneur, right? I was always trying to make things better, was trying to see things differently, was very curious as a child. Like, why does it have to be this way? Like what if we thought about it this way, right/ And so from an entrepreneur perspective of looking at something and saying, how do we improve it?

Or how do we make it better for the people who use it? I think that was always something within me. Yeah, my parents were, you know, first generation college themselves on both sides. And my father definitely has an entrepreneurial background, but he chose a very safe career as a financial controller of a titanium company.

So could not be more safe. But really stable for him to, you know, send me and my brother to college and provide for us and, you know, have a stable life that he didn't have. And my mom was actually at 17, decided to be a woman engineer in the healthcare space. And so, I think she was a pioneer in the sense of, you know, not many women were going to coding school at the time that she was, especially in the healthcare space. And she's worked for McKesson as an engineer for 45 years now running teams and developers.

But my dad had ideas and he was creative, and he thought of businesses growing up. And before I went to college, he actually gave me the option and said, I will pay for your college, or I will actually give you that money and you can start your own business. And I didn't understand the choice and so, of course, I chose college because all my friends were doing that, and I didn't know what I would've started. But now looking back at it, I'm like, wow, if that was today, I would've taken the money and built something.

[00:07:49] Sanjay Parekh: Right. Yeah. That, that is fascinating that I don't think I've heard of many parents giving their kids that kind of choice. That is, now even though you didn't take the choice and you still went the regular path, it's still a gift, right?

[00:08:03] Shaina Shiwarski: Yep.

[00:08:03] Sanjay Parekh: Because it kind of affects the way you think about things in the future and the people that you deal with. So that's fascinating. And by the way, I often say you know, people talk about taking a job is the safe choice. I think that what we do as entrepreneurs is the safe choice. Because we go to work every day and nobody can fire us except ourselves and these people that take jobs with companies, man, they are so courageous.

Because they're taking jobs and they're not in control of when they might lose their jobs. So, you know I kind of twist that idea a little bit. So, I think your parents are actually the courageous ones. We're taking the easy way out and just starting up companies.

So, let's dive into Legends. What made you decide that you wanted to do a travel company? First of all, I will tell you, I'm fascinated by this. I have been looking at travel apps lately quite a bit, because as things are starting to open up and we're traveling more, I'm trying to understand kind of what apps are out there.

So, I really am super excited about what you're building. So, but what, you know, I know you said that, you know, as a kid you wanted to be outdoors and all that, but what really made you want to say like, I really want to do this, you know, for the next eight, 10 years?

[00:09:13] Shaina Shiwarski: Yeah. So, I met my co-founder about six years ago. She is Stephanie Daniels. She is British. She's also from, you know, grew up similarly to me, grew up in a small town outside of London and we both met each other socially in New York and every time we would talk, you know, we were bound by this passion of exploration and travel and both of us had been through a series of different things in life.

And we kept coming back to this aspect that when you travel, you are put in situations and circumstances that really bring you back to yourself, right? Remove the barriers, they remove the bias, and you're presented with challenges and different situations that make you think about, who are you?

And so often in life, we work for those moments to come back to ourselves for the week or the two weeks that we take trips, right? And for us, like self-actualization and mutual evolution really comes from exploring the world and finding community of people around the world to help doing that.

And so, when we met on this shared kind of idea of how do we empower people to authentically connect with themselves, each other, and the world, we said, what is our unique skill set as well that we have, that we can kind of harness here? And so, with my background in tech and hers, she spent 15 years at at Deutsche Bank running, you know, hundreds of millions of dollar revenue teams on the executive team there.

We said, what can we do in this space that hasn't been solved? And while we were traveling, we said, you know, it's really strange in, in the 21st century, especially with all these apps that we have, and we use every day, that there still isn’t app for travel that you use every day. And so, when we looked at the travel landscape and the travel tech landscape we saw that everything that was built in this linear cycle of: you plan, you dream, you plan, you book, and then you experience.

And sharing is this after thought that is done on social platforms like Instagram and TikTok, but none of it feeds back to the ecosystem of the travel landscape and the travel tech doesn't connect together either. And you look at all those categories of dreaming, planning, booking. There's hundreds of different sites, none of them integrate.

None of it is socially validated and also the process isn't linear, right? When you purchase fashion now on Instagram, you can go in, and not even know you're looking for inspiration, and end up buying something because the inspiration is so well, there's social validation, but also maybe like, it doesn't need to be that intentional.

And then when we looked, and so we looked at the travel landscape, we looked at then the social landscape of social networks, like Instagram and TikTok, and we said, when you look at Twitter and when you look at why a new niche, interactive community or a social network has evolved it's because all of the ones that exist, the infrastructure of how they're built, doesn't align for the category that is not being served. Right?

And so, in this sense, category is travel. And so, you have a ton of demand for people wanting to share their travel experiences. So, you have a ton of people sharing, you know, one moment in time post on Instagram of a beautiful picture of them, but not actually the hotel or restaurant they went to that then their friend can book.

And so we said, we believe there's a huge gap in the architecture of how these social tech companies are built that aren't set up for the travel journey of a user. And we said, what would it look like to actually put the user first, incorporate web three principles of ownership, contribution, value to the users, and layer in the travel kind of ecosystem and process.

And so, for us that excites us. Because us as travelers that solves, you know, big pain point of coming back from a trip and someone saying, share recommendations to me, or I was just talking to someone this morning who was saying they're going to, you know, Lisbon, Paris and London, and I have all these recommendations, and normally it would take me hours to sift through, okay, what was that restaurant I went to? Where did I stay from that hotel?

And now imagine all your photos that you take becoming instant recommendations for your friends. And that's what we're doing is we're removing the barrier to share and to create these experiences for other people, for the everyday person and not the influencer who spends their career doing that or is trying to make money.

[00:13:57] Sanjay Parekh: So I absolutely love this because I have experienced this myself. So, we do road trips, we do travel and whatnot, and I end putting together an itinerary in a text document. And then I save that on Dropbox for the case when somebody asks like, hey when you did that Southwest trip, what did you go do?

I can just give them the text document then it's kind of up to them to sift through it all and figure it all out. So, the other part of what you're doing that I love, is the social part of it, where you know, that it's your friends that are making these recommendations. I think that one of the biggest struggles that everybody has is you go to these sites that are recommendation engines, and you don't know if you can trust the recommendation, right?

It's supposed to be crowdsourced, but now we know that there's so many bots and things that people do to game the system and game the rankings, and you've got it on Amazon. You've got it on all these sites, but if it's your friends, you know, look, I know Shaina's telling me this. She's not going to steer me wrong.

She's not like trying to get me to go to some place because she has a stake in that place.

[00:15:03] Shaina Shiwarski: Right.

[00:15:03] Sanjay Parekh: She's telling me because it's the right place to go. So, I absolutely love that. The challenge, I think, that you've got and you've obviously, already think thought about this is like, how do you grow this? How do you scale this? Because that's why a lot of these sites have gotten it opened for everybody. So how do you penetrate this market and say like, hey, you and your friends need to all come on board to, to make this useful.

[00:15:24] Shaina Shiwarski: Yeah, it's a great, great question. And you know, the cold start problem that everyone asks you know how do you get the network?

[00:15:31] Sanjay Parekh: Right.

[00:15:31] Shaina Shiwarski: I think there's two things that we believe are true. One, content is not the issue. Like we there's information overload on the industry. It's about how do you take data that is currently unusable. So even for our process, right, like users have thousands of photos on their phone. Like there is location data on those photos that we automatically translate through our technology into a recommendation, right?

And so, thinking about the tech that you actually implement and how it visualizes and surfaces information that's actionable is one thing, right? And so, from a content perspective, I think content is not the issue. And so when we think about how do we have coverage, right? We're not thinking about, how do we, which a lot of companies in the travel space think of, how do we have a bunch of agents or people adding content and keeping it updated and and managing that and it gets outdated, right?

We say, how do we make the technology amazing so our users, similar to Waze, right, like our users are creating real time content and data. And then how do we apply really interesting visualization on top of that. So, in terms of the map, how do we show the data of your upcoming travels overlapped with your friends’ upcoming travels? So, planning doesn't have to be a full list of an itinerary.

It can be a visual, or it can be a push notification, right? And we're thinking about it as a game, right? Like it's not just one time transaction, right? We're thinking about over the life cycle of how you want to interact daily, like, what is the information you want to be fed and how do you want to interact with it?

And then the second thing, from a user-based perspective, there's a lot of existing communities out there that we can partner with. And so, we're really focused, initially, on what we call the new nomad, right? And so, for us, the new nomad is, you know, an adaptation of the digital nomad, right? The digital nomad, I think, has traditionally been seen as this person who is a backpacker, who doesn't have any money, who is going from one place to the other.

And the reality is, there's over 40 different countries right now that offer digital nomad visas for people who are in tech, who make more than, you know, anywhere from three to $5,000 a month. And the population of entrepreneurs and of managers, and now people in tech, who are this new nomad is quite significant.

And there's, you know, projections that by 2035 there'll be a billion, you know, of these new nomads. And so, we're looking at that person, and we're saying, not just specific to travel, but specific to communities, where do these people spend time, right? And so, we look at it from a work perspective.

So, is it people who, you know, spend time at WeWorks, spend time at Selina Hotels, use certain kind of products to help themselves efficiently, you know, work remotely on the go? Where do they stay, right? Do they stay at Soho House? Do they stay at Selina? Do they stay at some of these communities that are focusing more on this remote population? What type of wellness stuff do they like?

And how do they think about their mental health, their spiritual health? And then also what's the impact organizations, right? And so, we've laid out actually, the, all these categories of, you know, an individual as, you know, this new nomad and what does their day look like and what products are in their lives?

And then we're creating partnerships with those people to create community together. And I think we are more powerful, collectively, not only to make change, but also to help each other. And that's been our approach from the beginning is, not how do we do everything ourselves? But how do we do it with the community that we create?

[00:19:19] Adam Walker: Support for this podcast comes from Hiscox. Committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:19:36] Sanjay Parekh: Let's pivot a little bit and talk about you and why you decided to kind of take this leap. So, in doing this you were already working at a startup and then decided to go and do your own startup, essentially. When you were making this kind of transition, were you doing the new startup while you were still working or did you make a clean cut and then start, you know, without any safety net or anything?

[00:20:02] Shaina Shiwarski: Yeah, definitely. I think it's tough to just do the straight cut without any, you know, safety net. And so, my co-founder and I, we actually, you know, had a full year where both of us were working and we were prototyping. Right in the beginning, even when we said, hey, let's do something, you know, and some of our friends who have known us for a while, they're like Legends is like been, you know, the name Legends we've had for so long in our domain.

Because we said, hey, we're going to do something. And I think that's really where like, just taking one step at a time really does matter and it all adds up. And so, when we look back at where we started one step might be just buying a domain. And for a year playing around with different ideas. And we, you know, our first was she was, you know, a very important job at Deutche Bank, I was working out so many hours, you know, at a startup. But, you know, evenings and weekends, we would meet and we would talk about Legends and we'd have, you know, a glass of wine and we'd be like sketching on you know, large pieces of paper, like different product ideas.

And we got, we did a very small proof of concept on our first year, and we tested it, and we learned so much about working together and about, you know, the teams that we wanted to use. And then last year around kind of March, did we fully say, Okay, we're going to do this. And I was still working full time at my last company, and I was responsible for, you know, 90% of the revenue, right, at my last company.

And so, it wasn't an easy job. And I would, you know, schedule my seven to nine in the mornings were my Legends calls and like work during the day and then five to nine were, you know my Legends calls. And so I was kind of bookending Legends and I had a goal of, you know, a certain amount of financial stability that I wanted to have to be able to make the jump so that I could fully commit to, to us doing this.

And that kind of came in August of last year. And both of us have been full time since. And so, I think it's natural to start taking steps and seeing where that goes. And I think you'll know when the time is right. You know, I was getting depleted at my other company. The energy that I was getting from it was distracting me rather than giving me energy. And I felt like I couldn't give my best energy to Legends. And so, at that point, I said, you know, it's not worth us doing this if we both aren't giving our full energy. And what would it look like if we gave our full energy?

[00:22:39] Sanjay Parekh: So, okay, for that year then, you basically had two jobs, right? Yeah. You were bookending your day with Legends. How did you deal with the stress? And how did you manage that life work balance? Like, how did you manage all of that stuff? I mean, one of the nice things is Legends is about travel. So maybe life work balance can come as part of work, right. Because you get to travel and say that it's work. But it's really enjoying yourself. But how did you manage that year and manage the stress of it all?

[00:23:08] Shaina Shiwarski: Yeah, it's definitely stressful. And I think it makes you reassess why are you doing this, right? And if you're doing it for money, if you're doing it for ego, if you're doing it because you want to be known for something, like, that'll wear down after a year. And, it came back to, okay, we are doing this because we both fundamentally believe this problem needs to be solved and we feel extremely aligned to solving it.

And I think, you know, a mentor had told me once, you know you need to build it when you think about it every day for a year. And like at the point of when I quit, we had thought about it for two years every day. And you know, you wake up and it's the first thing I think about and it's the last thing I go to bed to.

And I think that's when you know that, through the tough times, because there are so many tough times in the beginning, you're going to get through it. Because if you can make it through those stressful situations and I think it is a test to can you make it through the tough times as an entrepreneur having two jobs, right?

Because you're always understaffed and under-resourced and don't have enough money. And so, it also took me back to kind of, what are my tools within myself that I can use to, you know, optimize my energy? And what I mean by optimize my energy is, if my energy is not in my best state, then it affects the rest of the team, right? And it affects my co-founder and everyone else.

And so, what I think about every day is, how do I feel my best for myself so that I can show up my best to other people? And they can in turn do that. So like yoga, you know, meditation, just simply, you know, taking walks on calls sometimes, like moving my body makes me feel balanced. And I think there's certain things that all of us have tools that we need to figure out that, you know, create our own balance and it's different for everyone.

[00:25:00] Sanjay Parekh: Yeah. So, it sounds like your team is it mostly remote? Or is there any clustering of people anywhere?

[00:25:08] Shaina Shiwarski: So very remote, as you can imagine, we're very global. We, so, you know, Steph and I get together every six weeks and we'll bring some of the team together. So, we kind of have a little of that. But we've been remote from the start. Especially, you know, during COVID while everything was going on.

We have a cluster of engineers in India. Our lead engineer is based in San Francisco. But we truly are kind of all over the place, which I think is nice. And it provides for also, a nice cultural dynamic as well. And we're testing in different markets and for what we're building, I think it makes a lot of sense.

[00:25:48] Sanjay Parekh: So yeah, we haven't even touched upon the idea of building a travel company during a pandemic when nobody was traveling. But we're going to leave that to the side. I want to talk about how do you think about motivating, then and making sure that a remote team, you know, people that you can't see every single day. How are you thinking about keeping them motivated and checking in with them? Like, are there things that you're doing to keep that you know, going in the right direction?

[00:26:13] Shaina Shiwarski: Yeah, I think it's something I think about all the time. Operational efficiency or, you know, operational organization.

I think, you know, especially as a startup and in the beginning of of the stage, especially when it's your company, like there's this tendency to want to like over micromanage, right? Because you want control of how everything is happening. But I think that disguises the gaps that you have sometimes.

And so, I think you have to be willing that you have to be willing for things not to be perfect and for things to fail, but quickly iterate and solve them. And so, we, you know, obviously use, you know, certain communication tools like Slack and different project management tools like Monday.com, and those have helped us like create consistent kind of weekly organization structures.

But it is I think, you know, it's something that I wouldn't say it's perfect. Right? And that we are constantly optimizing for. And I think why it's interesting, you know, from a remote perspective, I think there's a lot of policies and procedures you can put in place to say, hey, this is how we communicate, or this is how we do that.

And what a lot of people don't realize is everyone has already a kind of inherited like way of communicating that they come into a situation. And if we don't first stop to say, how does this person perceive information, receive information and then how do they take action on it, and create something around that, then we're just trying to fit everyone into one box.

And so, what we've tried to do is really uncover across the team, like how do we need to communicate to this person to make them feel heard, to make them feel supported, to make them feel like they can take action without us. And that's something that has to be intentional. And I think in the beginning is really one to one.

And so that's worked really well for us is not looking at everyone the same. And saying, okay, this person is this style, how do we then put support around them that is a different style? And how do we make our expectations that this person is really amazing at this, but might not be great at this, in managing the team that way.

[00:28:29] Sanjay Parekh: Yeah, I love that. What you said reminded me of every time I go to the doctor and I don't know why they ask me this every single time, they ask you, do you learn better by seeing something, doing something, or something? I don't know what it is. I feel like it's a test every time, because I feel like I end up picking the wrong, you know, like the different thing every single time.

And they're probably wondering, like, why does this guy keep changing the way he learns? I don't know. Okay, since I've got you on the podcast there's one question I've been burning to, you know, like ask you this whole time because you are obviously a travel junkie.

If there was just one place that you could visit or vacation in, where would that be and why? I'm trying to give our listeners like a little tip here before they even use the app. Like you're now all of our travel friend. Like what's that one place that we should go?

[00:29:18] Shaina Shiwarski: Oh my gosh, it's so hard. I really would love to go to Namibia. There's these like sand dunes with these old shipwreck hotels that are supposed to be amazing.

I just haven't explored that part of the world yet. So that's definitely on my list. If I would say someplace I have been, that I think is really fascinating is Malta, that no one talks about. And Malta is this, you know, really interesting mix between, you know, Africa and the Mediterranean, cause it's so close to both, but also, you know, you've got Sicily right above as well.

And the geography there is just really interesting and weird at the same time. But also, so much history has happened in Malta, and so a lot of the bases for wars in the past. And so, they have these really beautiful churches, really beautiful towns, but no, one's really in it. So, you can walk through these villages that have so much history and beautiful architecture. But then also you can do scuba diving there and rock climbing and — yeah it's one of the most unique little islands and places that I've been to that I think, that never really shows up on people's radar. So.

[00:30:38] Sanjay Parekh: Well, I’ve got to say Malta was not on my list of places to go, but now it is. And Namibia, I didn't even know about shipwreck hotel, so yeah. That's definitely going to be on the list too. Shaina, this has been awesome. Thank you so much for coming on the podcast. We all now at least have a couple of places that we need to now visit in the world. But our listeners can find you at Live Like Legends. Is that right?

[00:31:04] Shaina Shiwarski: Live my legend.

[00:31:05] Sanjay Parekh: Live my legend. Sorry. LiveMyLegend.com. And check out the app and travel the world and share your experiences with friends.

[00:31:14] Shaina Shiwarski: Yeah, exactly. Thank you so much for having me. It's been a pleasure.

[00:31:23] Sanjay Parekh: Thank you for listening to this week’s episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit Hiscox.com/shareyourstory. I’m your host, Sanjay Parekh. You can find me on Twitter at @sanjay or on my website at sanjayparekh.com.