Matt Bowles: My guest today is Kelly Lewis. She is an entrepreneur, travel maven, author and keynote speaker who grew up in Hawaii and has now traveled to over 85 countries on all seven continents. In 2010, she founded Go Girl Guides, a company that produces travel guidebooks and online resources specifically designed for women. Kelly’s innovative approach to female travel helped to revolutionize the industry, and in 2016, she founded Damesly. A travel company that offers immersive experiences for women led by female experts in their respective fields. The company provides opportunities for women to connect, learn, and explore new destinations together in a supportive and empowering environment. Kelly is also the founder of the Women’s Travel Fest, an annual conference that brings together women from around the world to share their travel experiences and learn from each other. The event has become one of the most influential gatherings in the travel industry, attracting thousands of attendees each year. Throughout her career, Kelly has been recognized as a trailblazer and innovator in the travel industry. And her work has been featured in numerous media outlets, including Forbes, CNN, the New York times, and the list goes on.

Kelly, welcome to the show.

Kelly Lewis: Thank you so much for having me. I’m so excited.

Matt Bowles: I am so excited to have you here. You are doing amazing things that we’re going to dive into but first let’s just start off by setting the scene and talking about where we are recording this from today. We are not in person unfortunately. I am actually on the West coast of Africa today. I am in Luanda, Africa. Angola. And where are you?

Kelly Lewis: Cool. That’s way cooler than where I am. I’m in rainy Portland, Oregon.

Matt Bowles: Portland, Oregon is a cool city though. You know, what’s crazy is that I had never been to Portland until about two years ago, and I actually went there for the first time with a mutual friend of ours, Nora Dunn; The Professional Hobo. She and I decided to do a cross-country train trip. So, we got on the train in Chicago, Illinois, and took the train all the way across the country to Portland. And then we were doing wine tours out in Willamette Valley and going into the Portland restaurant scene. And we had an absolute blast. I think it’s a completely underrated city.

Kelly Lewis: Yeah, I actually remember when she was doing that tour. It is. It’s really fun. It’s a great foodie town. I’ve spent this weekend actually at some of the hippest restaurants just because my friends are wizards at getting reservations that are impossible to get. And my husband always says bad food doesn’t last long in this town because we really are just such a destination.

Matt Bowles: Well, you also just had the Women’s Travel Fest and there was a whole bunch of incredible people there. It was really fun for me to see cause I have interviewed a bunch of these people on the podcast. People like Mickela Mallozzi, Gabby Beckford, Nora Dunn of course were there. And it’s really amazing to see just the caliber of people that you pull in as the speakers. I can only imagine. I’ve never been in person, but what the crowd and the audience is like, it looks like an incredible event, but how was the event for you this year?

Kelly Lewis: So, this year was year 10 of Women’s Travel Fest, which is just. Absolutely insane, because when I started Women’s Travel Fest, I was 25 and a bartender, and I just had this idea to bring together a group of like-minded women, because I knew the energy of talking about travel is so special and so contagious. And I knew if we could amplify that in a bigger way, that it would be a really cool thing.

So, I just started the show with zero experience in how to produce events. Really, it’s not a lot of money. I maxed out all of my credit cards. I utilized my bar connections. I was talking to our beer vendors to get things sampled, thrown in for free. I was so scrappy and hungry. And I just really wanted to create. An event and build a community. And so, this year was such a full circle moment because the very first year it started, it was me and Mickela Mallozzi in her kitchen. And I remember it like it was yesterday, we were saying, okay, if we could do something amazing in the women’s travel space, which by the way, there was no women’s travel space back then.

We really weren’t even talking about the differences between travel for different people. So, this was really like an innovative idea, but we didn’t realize that at the time. So, we were sitting in her kitchen, and we were like, who could we get? If we could get anyone. And we were like, Samantha Brown has to be Samantha Brown. And it was such a wild way that we went about it because Mickela knew Sam’s cat sitter, who we literally worked that connection. So, we approached the cat sitter, and we were like, hey, how do we get Samantha Brown? And somehow, we got her to keynote the first year, which we were like over the moon fangirling.

So excited because she’s an amazing human being and a wonderful speaker and just such an icon. And so, every year since that year, we’ve tried to get her back and it has never worked out. And then for year 10, it was like full circle. She came on. Pauline Frommer came on. We had 35 powerhouse speakers. It was probably the biggest and best show we’ve ever had. And it was phenomenal. It was so fun.

Matt Bowles: That is so amazing. And it’s so fun to hear the original story with Mickela. What an extraordinary human being she is. I’m going to link up Mickela Mallozzi’s interview in the show notes, because that was an incredible conversation. She is doing absolutely amazing things.

So, if folks don’t know Mickela, definitely want you to go back and listen to that episode as well. But Kelly, let’s start now all the way back because I want to give folks a little bit of background and context on you. Can you talk about where you grew up and as you were coming up, how did your interest in world travel initially start to develop when you think back?

Kelly Lewis: I grew up in Hawaii on the East side of Oahu. And I always talk about how I feel like I had a Moana moment. I was on my neighbor’s swing set legitimately in her backyard. We had to bend like six or seven. And I remember thinking there are places where you can just drive for more than two hours, like, because I’ve never had that experience, and I just remember understanding how vast the world was, and really being curious about exploring it, but I grew up in Hawaii, which is like, amazing, but it’s also a super expensive destination, which I didn’t realize when I was a kid, but it explains why we never traveled because I had a family of six.

There were six of us all together, four kids and my mom and stepdad. And so, we just couldn’t afford to get off the islands very often with all of us. And so, we really didn’t travel very much, but I always had this sense of curiosity about what the world was looked like, and like a really distinct calling to go out and see it for myself.

Matt Bowles: And so, when were you eventually able to leave the island and where did you go?

Kelly Lewis: Yeah. So, I left literally three days after I graduated high school. While Hawaii is an amazing environment, the house that I grew up in was not always so great. So, I was like, I am out of here. I want to make my own way. No one’s going to tell me what to do. I’m at peace. I’m out.

So, I left three days after I graduated. I moved to Arizona. I went to the University of Arizona. And then it wasn’t until after I graduated college that I finally had the time and the ability to go out and travel. I didn’t have the money, so I had to get really creative on what that looked like, but I went to New Zealand and Australia and Fiji. It was a graduation gift for my family, which really kick started my whole life, and I didn’t know it at the time. I went with my best friend and when we got to New Zealand, we met someone that she knew who was living there on a working holiday visa. And I was like, I need you to tell me every single thing about how to do this. How do I live here? How do I make this happen?

And he told me, and so I went home, I applied for a working holiday visa. I sold every single thing I owned. Like I sold my toaster, I sold my rug, anything that had value that could have a value, I sold. And then I moved to New Zealand for a one year working holiday visa. I think I had 600 in my pocket. I knew absolutely no one there, and I made it work. So, it turned out to be the best adventure of my entire life, and I had so many formative experiences in that year, and I’ll never forget it, because I graduated college in 2008 with a journalism degree. So, if we all remember 2008, it was like a terrible time to get a job.

And I had a job offer from this tiny newspaper in Wyoming and I was really considering it. But this was like, I have to turn this down and I have to see what’s out there because I know this is a chance for me to do that. So, I turned down that job, I went to New Zealand, and then I got there, and the first job that I got was as a cleaner, like a room cleaner, in this hostel. Which is a terrible job, very thankless position, I saw some things that I will never recover from, but it was also so much fun, and so I got to meet travelers from all over the place, and then I saw a job opening in Queenstown for this company that did Lord of the Rings tours. So, I flew over there, I met a girl in the airport, and we hit it off because our flight was delayed, and so I flew over there for the interview, didn’t get the job, actually, but stayed in touch with that girl.

And then the person that they hired didn’t work out. So, they called me, and they were like, hey, sorry, we made the wrong choice. Could you actually have the job? And so, I called that girl, Christie, and I was like, hey, I’m moving to Queenstown. Can I crash with you for a few weeks? So, I just feel like. Traveling is one of those things that shows you how delightful human beings are, and that the world is mostly safe, and people are mostly good. And my whole entire year on my own in New Zealand really reinforced that perspective and it became the driving force for what I do in my career. I just didn’t know it yet.

Matt Bowles: So, after you did the year in New Zealand and you were inspired to keep traveling, how did you make that travel happen? What did your travel life look like in the subsequent years?

Kelly Lewis: Yeah, those were the vagabond years, right? We had no money and a lot of time. So, actually, living in New Zealand was really the kick starter for everything because I lived in one of those super random traveler houses where there’s actually two bedrooms but nine people living there somehow and it took me a couple weeks to be like, okay, who actually lives here? Because there’s five people in the basement, two dudes outside in the vans, but being around all of those people travelers, I got to hear from them. And they would say, oh, China was amazing, and they’d tell me all about their experiences in China, and it would make me want to go to China, where I never really had that desire before.

And it’s the Traveler’s Grapevine, so that was my first introduction to that. So, I ended up getting a job at a Lord of the Rings tour company and saving all of my money and my roommates and I went on a two month long backpacking experience through South America. And so, we were taking buses everywhere, we were staying in hostels, we were just being hooligans, you know, stringing together every nickel we had to kind of like to have these amazing experiences, but I think that’s such a special time in life.

Matt Bowles: A hundred percent totally agreed. Well, I know you eventually did make it to China, and I understand you took the world’s highest bungee jump in Macau. Can you talk about that experience?

Kelly Lewis: Oh my god. Do you ever have experiences where you’re like, I feel an alien invaded my body. I am not brave enough to do these brave things. And okay, so, I was in Macau actually on a press trip and we were staying in all these beautiful resorts, and I knew that AJ Hackett had the world’s largest, highest bungee in Macau, and I knew that because I lived in New Zealand, obviously right next to AJ Hackett in Queenstown. And so, I was like, I would love to do this. And there was one other guy on the trip who was like, I’ll do it with you. But I don’t know why I said that because I’m such an actual chicken. So, then I spent six days in Macau, and this was happening on the fifth day.

So, I spent five days in full panic. Standing at the window of my hotel being like, how am I going to jump? How am I going to actually get my body to leave this platform? And then all of a sudden, you’re up there and it’s happening, and I’m out of my body, and you don’t realize the wind gushing at you. It was on the 60th floor of this property. And it’s not like, in New Zealand, you jump into canyons with water. It’s beautiful. This is like on asphalt. Like, you are in the city.

So, I’m standing up there, And I’m completely freaking out and I don’t feel my legs anymore and I’m on the edge before I even know it and then the guy’s telling me to look at the camera and I knew because I watched all these YouTube videos that when you look at the camera, then you fall. And so, I’m like, Oh God, I’m good. Like, how am I going to do this? And I remember just begging him. I was like, please push me. Please push me. Please push me. So, at the very last minute, he leans in, and he goes, okay, the next thing I know, I am falling down the side of this building and it was crazy. It was the craziest, most freeing, funniest feeling, but it wasn’t until I actually caught that I was like, woohoo, not going to die.

And then I could really enjoy it. The second I was dangling there, I was like, I want to do that again. Like you get so brave. But now that I’m looking at it, I’m like, never again. I don’t need to do that ever. One and done. It was terrifying, but fun.

Matt Bowles: That is incredible. But you’ve got the story to tell and the T-shirt to wear and all that good stuff. I know you have also spent a lot of additional time traveling around Asia. And I want to ask you about your experiences in Thailand. That’s a super special country for you. Can you share what your experience has been like in Thailand and any highlights from your travels there?

Kelly Lewis: Yeah, so Thailand is really special to me because when I started Go Girl Guides, it was 2010, so this was like after that time in New Zealand and I was back, working as a journalist, in an office that I hated, with a boss that was such a tyrant and the whole thing was awful. And I was bartending at night trying to figure out how am I going to pay to get myself back out in the world, saving all my money.

Anyway, I had this dream in the middle of the night that I was looking at a travel guidebook for women and in my dream, I was going, oh my gosh, this is totally you’re calling. You should have done this. Now somebody else did it. And so, I woke up from that dream and actually didn’t remember it until midday. And I was sitting in my office under these fluorescent lights, and I remembered the dream and I was like, oh my god somebody has got to have done travel guidebooks for women. This cannot be an original thought. This was 2010 so I started googling and it had never been done and so that’s when I was like, this is my soul’s calling. This is my purpose. I’m going to get out there and do it.

And so, Thailand was the first place that I went to was the first guidebook that go girl ever produced. So, I went to Thailand for four months with my best friend who I actually did that graduation trip with. And she was the photographer. And so, we just traveled around in every place we went, we said, what’s something that I feel women should know about this? Lonely Planet had been around, guidebooks had been around, but I just kept feeling there was so much information that my girlfriends were giving me that my guidebooks weren’t.

And so, I was like, okay, what part of town is sketchy? What’s the bus station like at night? How is that going to feel for someone who’s coming here by themselves? And so, I was thinking about it with a different perspective. What would I tell my best friend or my sister if she was going to Thailand? So that’s kind of how it started, and we went through Thailand. We traveled all over Thailand. It was incredible and I met so many beautiful people at that time in life and one in particular really made an impact on me. Her name is Lek, and she runs Elephant Nature Park.

And so, in 2010, we still were riding elephants most frequently. We had come a long way in the past 13 years in talking about not only gender, but how we travel, animal experiences, what that looks like. But Lek at the time was just building Elephant Nature Park. And I remember she was this tiny little five. I’m five foot one. She’s like, maybe even shorter than I am, maybe five feet, but so powerful because she was like single handedly taking down the logging industry in Thailand and changing how people think and how we talk about animal experiences.

Meeting her was one of those moments where I was like, there’s so much here to discover and uncover and to talk about as women doing really cool things in the world that are actually changing the world. And so, Thailand was so special to me because we saw every corner of it to write the book. And I really got to understand the culture and I can’t wait to go back. I’m actually going back for the first time in a long time in June. So, I can’t wait.

Matt Bowles: I, as well, have been to Thailand a number of times and it is such an incredibly special place. I want to talk a little bit about your entrepreneurial journey, and I think the Go Girl guides would be a great place to start with that. Can you talk about how that eventually came out, how it got published, and what sort of the trajectory was from there, from Thailand?

Kelly Lewis: Yeah, so, if I look back on my life, at every point, I had no idea what I was doing, right? So, like, the Go Girl guides were no exception. I was a journalist, I knew how to do that.

I had no idea about publishing books, nothing. I didn’t know about page thickness, absolutely nothing. But I figured it out. So, I had gotten an email in my inbox from Jostens. And what I remember from Jostens is they did yearbooks. But they also had a commercial print center, which I didn’t know. So, I just emailed someone randomly from my inbox, and I was like, hey, I have this idea. I have a vision for what I want them to look like and feel like. Can you help me to actually put them on paper? And they did.

So, Jostens came on as our print center, and then I kind of had to figure out everything on how independent publishing works and how to sell and market those books and so that was just a couple of years of trial and error. But I also knew that we were really on to something and so we needed to scale. So, Thailand came out and then Mexico came out and then Argentina came out. And then we just really grew London came out we did New York City we grew as quickly as we could and at one point online. Go Girl had probably 40 different writers writing from different sections of the world and the books were going really great.

And that was when I was living in Arizona, and I wanted to move to New York City. And so, at that point in my life was when I said, okay, let’s figure out how to talk about travel to more people. And I went on a cross-country road trip where I was talking about a cross-country book tour where I was talking to women about the books, and we were talking about travel, and I loved this conversation so much that when I got to New York City.

I was like, okay, I want to start the women’s travel fast. Right. And it happened because I was speaking at another event in New York city. And Michaela Mallozzi was like the AV girl. Like she was running the microphone. She was running Q and A, and somehow, she and I and Masha and Christine, a couple of other girls, ended up in a bar in New York city, and I was like, hey, I had this wild idea. What do y’all think about it? And they were like, that’s awesome. Let’s do it. So, I was like, okay, cool. So now we have Go Girl. Let’s talk about travel in a bigger way with the Women’s Travel Fest. And then after a few years of doing that, you know, the show started out as a one-day event.

It was 75 and it turned into a three-day event, which is now 497, but it really grew so. And very quickly. And then I was like, okay, cool. We’ve done this. We’re talking about travel. How do we actually take people traveling? And so that’s how Damesly started, which was in 2016. So, everything is kind of built on everything else.

Matt Bowles: Can you talk a little bit about women’s travel fast, just for folks that have never been, maybe it’s their first time hearing about it. What. What type of experience does it currently offer today and what can people expect from it?

Kelly Lewis: Yeah. So, it’s a three-day conference dedicated to inspiring, connecting, and supporting women who love to travel. So, we have speakers, panels, keynotes, everything surrounding women’s travel, everything from traveling safely, traveling on a budget, traveling with family. We’ve honestly talked about a lot in the 10 years, right? But every year we find new things to discuss.

This year, we had a really amazing speaker who was talking about renting out your house and traveling, which is a totally new angle. And I thought that we’ve never covered before. So, I thought that was really, really awesome and super informative. So, it’s three days of connection, networking, parties, speakers, keynotes, panels. It is a true fest. It is a blast. It’s women usually in three or four men, but men are allowed, you know, everybody, all genders are welcome. So, it’s just a good time.

Matt Bowles: Awesome.

Kelly Lewis: I don’t exactly know what the future is for the show because I actually just sold it. So, I am no longer the owner of the event. The new owner is Alex Jimenez of Travel Fashion Girl, and she is such a powerhouse. Such a boss and really such an inspiration in being Latina and being just who she is being such a leader in her own right.

So, we discussed how the transfer was going to happen, and I am so excited for her to go on her journey and put her stamp on the event and to continue it. And I got to a place in my life and in my entrepreneurial career where I was like, I can’t do all the things. Because if you try to do too many things, you end up overwhelmed and you do none of the things. So, I’m also newly married. I got married last year, and I just was looking at my life and where I wanted to go and I was like, something has to give, right? But I don’t want the show to stop because it’s such a special event. It’s Such a cool community. And it’s such a blast.

So, Alex Jimenez is the new owner, and I can’t wait to see what she’s going to do with it. And I will be supporting her and cheering her on from afar. I think that the way that she and I handled a transfer of a business has really been so beautiful. And we’ve really supported each other at every step of the way. And what I love is all the comments for people who are like, this is how women should do it. Supporting one another with love and encouragement. And that is exactly how we both feel, how I feel, how she feels. So, it’s been a really beautiful process.

Matt Bowles: That’s amazing. And congratulations on the exit and for building a brand that will now live on and continue to do amazing things. So that is super incredible. I also want to talk about the company that you are running now, Damesly. Can you give a little bit of the origin story of Damesly? What the initial need or the void was that you saw, why you created it, and what Damesly offers, and to whom?

Kelly Lewis: For sure. So, Damesly is a boutique women’s tour company. We looked at the travel industry and said, okay, right now, in 2016, this is 2016, right now you have either tours for older people. Or tours for younger people, right? There’s like Contiki, killing it for the 18 to 30 games. And then you had like Rick Steves and big bus tours for older travelers. But I couldn’t find anything in the thirties, forties range for women who were super career driven like myself and who had the means and the time and the want to do to travel.

So Damesly started originally as a kind of blending the workshop model of travel fest with travel. So, we started off doing photography tours through the Grand Canyon, led by a female photographer and creative writing retreats that included horseback riding through the Rocky Mountains and like really kind of blending adventure and creative learning.

And then we got a lot of people who were like, hey, this is awesome. But we don’t really want to learn anything. We just want to see the world. And so, I was like, okay. So, we expanded just to do general adventures. So, we do a lot of stuff in the Middle East and Africa. We routinely do Morocco, Egypt, Jordan, places that I think are just a little more intimidating for women to travel to solo. And that’s kind of been the way that we grew is we wanted to take destinations like that in Africa and the Middle East and make them boutique and luxe because we fancy, you know, we like a good hotel. We like good meals. My backpacking days are gone, and I don’t miss them. I think that’s really kind of how we evolved is to do more remote destinations and doing them very nicely.

And so that’s sort of where Damesly is now and looking forward with it being my only business now, which is wild. So Go Girl has transitioned. Travel Fest has been sold. I’m just in a different spot in entrepreneurship. And so, looking at it now, I’m super excited to pour 100 percent of my energy into it. Go back to our original model, expand our workshops, both digitally and around the world. And yeah, keep doing adventures and adding some wellness retreats. So, I think probably Hawaii is where I’m going to end up again, because all things come full circle and that’s where I’m from. So, I’m very excited about the future of that business.

Matt Bowles: I was super impressed with the Damesly website, just going through it and looking at some of your upcoming destinations this year that still have room available on some of the trips. You are taking people to Cuba. You are taking people to Bhutan. You’re taking people to Uzbekistan. I mean, these are places that I have not been to that are extremely high on my list. And then I was looking at your website and you’re going to all of these incredible places. So, for places like that, can you give folks an example of what the experience is like if they sign up for one of those trips?

Kelly Lewis: Absolutely. So, first thing, we stay in Boutique Accommodation, which is either four or five stars. That’s our jam. We like it nice. But every trip will have its own kind of flavor. So, Cuba, for example, we really do a lot of local experiences because we travel under support for the Cuban people. So, we have a lot of people-to-people experiences. A walking tour where we meet a street artist and we talk about street art and graffiti in Cuba and the legalities and complexities of that, which is so fun. And, you know, we do a lot of one-on-one cooking experiences where we’ll meet local female chefs and experience the world through their eyes.

Actually, I’m leading a tour to Georgia, Republic of Georgia, in May, and I’m not really the trip leader so often anymore because I have some exceptional ladies who are my trip leaders, so I’m kind of more like backend of things these days. But I am leading a tour to Georgia, and Georgia is the birthplace of wine biblically, and so I’m so excited to go there because I love wine. But really this tour has become a female wine winemaker and culinary experience.

So, we are meeting women who are winemakers in the birthplace of wine whose families have been producing wine for centuries and we’re dining with them. It’s going to be so fun and so cool and so different. And so, I like to put these little personalized interactions on all of my tours, because you can see something.

But I really do believe that people are different, like meeting people. Like in Thailand, sometimes you think back on that one person you met and how they changed your perspective on things. And that for me the reason to go on a group tour is because someone else has prepared this itinerary, has put you in front of these people, has allowed you to have space and time for connection because you’re not thinking about logistics. That’s something that I really like to do. We try to support as many women as possible on our itineraries. We really look for boutique properties that are women owned. If we can stay there to have female guides whenever possible, and it’s not always possible, like In Morocco, we struggle to find female tour guides and Oman, it doesn’t even exist.

So, it’s hard sometimes to fully make every, like in a perfect world, I’d love for everything to be female owned, right? Cause I’m just a huge feminist and I want to support women, but it’s not always possible in the destinations that we travel to, but it’s going to be cool to look back and see how Oman has progressed and even just in the past couple of years and in 10 years from now, where they’re going.

And one of the coolest things that we did on our Oman tour, which just ran, we had dinner at a local Omani businesswoman’s house, and there are not very many women in business in Oman. So just having the opportunity to talk to her, to buy from her, to see things from her perspective, to talk about women’s rights, to talk about the evolution of things I think is really unique and something we love to do on our tours.

Matt Bowles: Yeah, that is incredible. We’re going to link up the Damesly website so folks can check out what you’re up to, where you’re going and what these itineraries look like, because they are really incredible looking.

I also want to ask you know about your latest book, it’s called Tell Her She Can’t. Inspiring stories of unstoppable women, and it is blowing up. Can you talk about what inspired you to write the book and what it’s all about, what can folks expect from it?

Kelly Lewis: So, you might be sensing a theme here. I really like to do hard things, especially when people tell me not to, and I really like supporting women. So, tell her she can’t was kind of my pandemic project. I looked around and realized I had a handful of useless skills. I was a bartender who couldn’t bartend. A journalist when no one was writing. A traveler who couldn’t travel. A tour operator who had everything canceled. So, I was like, okay, well, all of my last case scenarios are not even available. So, let’s see what I can do.

But I had this idea, this spark, this fire to write a book for a really long time. And I really believe that things happen divinely and when they’re supposed to. So, I get a lot of like inspiration in the bathroom for some reason. So, in the bath one day and I kept hearing, tell her she can’t, tell her she can’t. And I was like, that is the title of my book, right? And I didn’t know what book it was going to be. I didn’t know the shape of it. And so, I started thinking about it. And then I started thinking about all the powerful women that I’ve met at Women’s Travel Fest. How many of those women were told that they couldn’t do things, including Mickela, she’s featured in the book.

But I grew up hearing that I wasn’t enough, that I couldn’t do things, that I would never be successful for whatever reason. And I had to make a conscious choice not to absorb that, and the only way that I could not absorb that was to just prove everyone wrong and prove myself wrong. That’s kind of like the impetus of my life. It’s like, screw you, watch me, right?

So that’s how Tell Her She Can’t started. I started writing my story about so many moments in my life when I grew up hearing all these things that I wasn’t enough and I couldn’t do it and how I just decided to double down and be like, just frickin’ watch me. And I started interviewing women. This was COVID time. So, everyone was home. We started having these hour-long conversations about people, the naysayers, the haters, the people who try to drag us down, the people who try to hold us back and how we kind of had to flip the middle finger to all of them and just do it, just do our own thing. And then how in doing that, you become an example of how things can be done.

So, people who doubt you, people who hate on you, they only do that until you’re successful. And then once you’re successful, then they’re like, oh my God, look at you go. Then they’re your biggest cheerleader. And that’s something that a lot of us spoke about. And with Mickela, obvioussly has been on your show before, but she has a TV show where she travels and dances around the world. And how many producers told her that she wasn’t ever going to be the star of the face of the show, that she wasn’t pretty enough. She wasn’t thin enough. She wasn’t this or that enough.

And it’s like, I have that too. And so many other women. And so, we just started talking. I had all of these phenomenal stories from women who have overcome traumatic experiences in their life, in their health. I had a woman in my book who a tree fell on her neck and broke her neck, and she had to reassemble her entire life. And everybody told her that she couldn’t, and she wouldn’t. And she did. She became a bestselling author. And then in creating that book, I have these 35 women who were really my champions, my circle, my corner.

And I love all of them. We still talk regularly. We’re all friends regularly. And so, in promoting the book and supporting the book, we created a huge boom and that it became an Amazon bestseller, like instantly it was number one in three or four categories, and we just pushed it, and it turned into a beautiful, beautiful project. And I am so happy that the pandemic gave me that opportunity.

Matt Bowles: Well, we are going to link it up in the show notes. I love that you have an audio version of the book as well. Folks can get it on audible if they prefer to do that, or they get it on Kindle or however they want to get it. So, we will link that up in the show notes for sure.

So, after your experience with writing the book and then marketing and selling the book to the extent that it’s sold, what reflections or tips do you have for first time authors who want to write a book and want to market and sell it as successfully as possible.

Kelly Lewis: Biggest thing that I did that made a difference was create a book squad. I said to my Facebook people, my friends, my family, hey, I need a crew of cheerleaders. I want you to be the first people to get the book. And in exchange, I need you to be the first people to review the book. I will send it to you for free to read it and then I need you to go buy it the day that it goes live or the day that you can pre-order it. And I need you to tell people about it because you’ve already read it.

So that was the biggest thing that I did was creating a community and I think I had like 60 some people in there and those 60 people, let’s say maybe 40 actually did that, but 40 people going out there and creating a big impact. In getting the book, in sharing the book, in talking about the book, that was the hugest thing that made a difference. So, if you are thinking about releasing a book, I’m a giant advocate for self-publishing. I could speak forever about the benefits of self-publishing, and I self-published Tell Her She Can’t, and it went so far so fast. Because it was a concerted effort, but that required being super clear on what dates you need things done by, who is going to do it, where they are going to go and really getting on with that tiny group.

I made a Facebook group just for my book crew. And I would get on video and say, I need you to do this right now. Please go. And everybody was so supportive and epic and amazing. And I know that some creators and some entrepreneurs are more private, they don’t really want to share their thing until it’s done because they’re afraid somebody might take the idea or they’re afraid for whatever reason.

I am a huge proponent in just being authentic and telling people where you’re at. This is what I’m trying to build. This is what I’m doing. This is the idea for it, and I need support. I need your help. And I feel like Just that attitude has been really helpful for me in all of my businesses and having a crew of people who are lifting you up when you doubt things and when it gets hard and helping to make your launches successful. And so that’s what I would say is like, share, share often and don’t be afraid.

Matt Bowles: Well, I also want to ask for some of your tips on event organizing. You have done the Women’s Travel Fest for 10 years. It is now a massive, consistently sold-out event. When you reflect back now on everything you’ve learned and how you are pulling this off consistently year after year, what tips do you have for folks that might want to start organizing events and doing it as effectively and getting such passionate returning customers as you are.

Kelly Lewis: I think the biggest thing I did, aside from not being terrified of my credit card statements, the first year I maxed out all of my credit cards. And that was so scary, but it had to be done. It was like a necessary risk. And I got super lucky in that. As soon as Samantha Brown came on, Expedia came on and they were like, we want to be your platinum sponsor. Let’s do this together. And they were our platinum sponsor for the first three years. And then Uber came in as our platinum sponsor and helped continue the show. We’ve worked with American Airlines and a lot of bigger brands, but that could not have happened had I not put my credit card down and just said, I’m not going to look at it yet, right?

I’m not going to think about it. Because it is expensive to do big things. And that was so scary. It took some steel cojones, right? To just be like, I’m not going to worry about it. It’s going to work itself out. Have faith that it’s going to work itself out. And then the other thing is I really reversed engineered the show based on what I thought the customer would want; my attendee would want.

So, I was thinking first and foremost about attendee experience and each year got better and better, right? We added coffee service. We have a really nice catered lunch every day. Our swag bags are so phenomenal. This year we gave people entire towels. The whole U.S.  park system maps on it. We give people shoes. It is so good. You can come just for the swag bag and be happy.

So, I think that’s the thing that is like, we really think about what’s going to make people happy. Are they going to be comfortable sitting here all day? And the other thing that we did was unique, which I did not realize at the time is I chose destinations like properties that were not hotels or convention centers. So, I think when you have an event, obviously it’s easier in a lot of ways to hold a show in a hotel. But everyone then has the option to go to their room whenever they want. And we had events off property. So, we took over our New York City show. It happens in an old synagogue from the 1800s and it’s two or three blocks away from the hotel, but it’s not so close that you can just dip out.

So, everybody stays in the room, the entire show. And we create an ecosystem in that energy because everyone is there from start to finish and they show up on day two in the morning it is always harder to get people there. So. At the end of day one, I say, listen, we have an amazing speaker kicking off day two and out of respect for her, I need you to show up here so you could hear her story because it’s going to inspire you and it’s going to change your life. And so, I think having an event in a nontraditional space has been pretty critical and the show has happened in New York City, San Francisco. It was also in a nontraditional space, New Orleans. It was in the jazz center. And Portland.

So, when we held it here, we held it in the World Forestry Center, which is kind of like in the forest. It’s in Forest Park. So, it’s really not close to your hotel. And that has been pretty critical in having space for community to gather and to stay together so that they can connect further. And I think that’s been a big part of it.

Matt Bowles: Well, you have now built from scratch multiple six figure businesses in different spaces. And it strikes me that you started having zero experience in any of these spaces. You had never written and published before. You’d never organized events before. You’d never run a tour operational group before, and yet you just started from scratch, figured it out, and then built all of these different companies in these different spaces and scaled them. To be successful brands. And I want to just ask for your reflections on that now, looking back and tips that you have for building a brand and scaling a business when you were bootstrapping it.

Kelly Lewis: Yeah. And then selling it. That’s been a new part of my entrepreneurial journey. So, here’s the thing I remember in 2014, I started as a travel blogger and as I was bartending. My first blog was called Travel Bug Juice, and I started it in like 2009 and that was kind of like a golden era of travel blogging. So, all of us travel bloggers, Nora, all of these people that you know, we all kind of were in that sphere at that time.

But then everybody started switching to the influencer led model. So, they would make their blogs about them and their perspective. And I think Nomadic Matt did a great job of that back before any of us were doing that. It was like one person’s perspective and moving forward and I kind of felt like I was doing it wrong for a while by building brands that I was not necessarily the face of.

So, people knew that I was running them, but I was building companies that were not just about me. And now in retrospect, well, that was exactly what I needed to do because building a company that’s not tied to just you allow you to grow that company and then sell that company. And that’s ultimately what entrepreneurship is, is like, I am an ideal machine. Every time I take a shower; I get an idea for a new business. So, I have to create the space for that in my life by letting go of things so I can build new things.

And so, building brands turned out to be. a key piece of that because if I just had Kelly Lewis’s travel blog or Kelly Lewis’s Women’s Travel Fest, it would not have been the same in building a community and a cause because it’s just attached to me. So now I’m getting a lot of really cool, exciting, and interesting requests to do one on one coaching with people who are trying to build brands. And I love doing that because what I thought in the beginning, I was doing wrong by building up myself, I actually realized I was doing right in the end. So, I’m excited to help other entrepreneurs build up companies, build up brands, and have the same success.

Matt Bowles: How do you structure your workdays? How do you optimize your productivity and maximize your efficiency and also just balance your life with all the other fun, cool stuff that you’ve got going on?

Kelly Lewis: I wish I had like a solid answer for this, but I honestly, I know what needs to get done and I do it when I feel like doing it. That’s not typical because I feel like a lot of entrepreneurs will say, well on Mondays we have to batch content and on Wednesdays we have to do, you know. I like to send out my newsletters on Wednesdays, so I try to get them done on Tuesday or Wednesday and then I send them out and I don’t overthink it too much.

I just try to get it all done and I just keep myself moving. And I also give myself space, so I don’t really work on Fridays because I don’t want to. Mondays I usually work half a day because I don’t want to. And I can be so hard on myself. I can be so critical of myself. I’m not productive enough. I’m not doing this enough. I don’t have a big enough team. I’m not delegating enough. But you have to do it at your own time. And remember that you are an entrepreneur because you want freedom of time. You want freedom to choose when and where and how you work. And so, giving myself that grace has been really powerful this year because I’m like, no, I’m going to sit here and watch Real Housewives because I want to.

And then maybe I’ll write a newsletter and then maybe I’ll have lunch. So, I just kind of figure out what do I want my life to look like? And now that I’m married, I married my husband last year, and so I want to be home with him more often. I don’t want to always be traveling. So, I also realized that I’m not great at everything. And my trip leaders, for example, are so good at group dynamics and leading groups. One of my trip leaders was a former teacher for 35 years, so she can hold a classroom. And she’s better at that than I am. So, I don’t lead a lot of groups because I take it too personally. If everyone’s not having a great time, I’m like, oh God, I ruined it. It’s my fault because I’m the owner of the business.

So, I make decisions that are best for my lifestyle right now. That means I want to be home more with my husband. We want to have a family at some point, and you have to kind of create space for that and not feel like you’re doing it wrong because here’s the thing. Like you said, I never knew what I was doing. I just knew I wanted to do it. So, I didn’t know anything. I had no expertise or certification in any of the things that I did. I just had a credit card, some balls, and I would just went for it. And that’s kind of what you have to do. And on the flip side of that is finding that energy of being like, okay, now I can just chill and I’m not going to feel bad about it. I’m going to take a Friday off every week because I want to. It’s giving yourself that permission.

Matt Bowles: You have now been to over 85 countries, all seven continents. When you think back about all of those travel experiences, what impact do you think travel has had on you as a person?

Kelly Lewis: Oh God, immeasurable. Travel has impacted my life immeasurably. Number one, it reminded me that people are good, and the world is safe. That is first and foremost. Anytime I have traveled, and I’ve had something go wrong, strangers who are angels have come to my rescue. I mean, I’m an optimist human being, so I really believe in the good of people, and I think travel has reinforced that for me. It’s also shown me how powerful and strong I am. And how capable I am at getting anything done because you can look back at things and be like, oh man, if you can navigate that insane market in China and figure out where you’re going, figure out how to get on the bus, you can do anything. You can apply travel skills to life skills.

I think it’s also taught me that the world is not that big. It still really blows my mind that if I wanted to, I could get on a plane today and wake up tomorrow on another continent, in another culture. And more and more now when I travel, I love having the space to do that. So, I’m leading the Georgia tour, but I’m adding in Armenia also, just for me, because I’ve never been to Armenia.

And I love just waking up in a new place and being like, I don’t know what this day is going to bring me, but let’s go find out. That’s my favorite. That’s how I feel the most free, the most activated, the most alive. So, travel has given me a spark for life in so many ways. It’s given me a career in so many ways.

When I was moving to New Zealand, I had no idea I’d end up working in travel. I thought I was going to be a journalist. I thought I was going to end up at that paper in Wyoming. And so, travel has changed my life and it’s given me a community and I have friends all over the world. That’s just such a beautiful ecosystem when you look at it. We’re only here on this planet for so long and this goes round. So, I just felt forever. I have to see it. I have to see it. I have to see it. And I would dream about places. I would dream about Egypt; I would just have these inclinations to go to these places.

And now I look at my life and I feel like I’ve seen so much and I’m so thankful for that because going to Antarctica and seeing water that clear and seeing ice that clear, it was like looking at the world before humans touched it. And that was so inspiring to me to remember our impact and what the world was and can be and is. Travel’s just given me everything and I never knew it. It was just me chasing my gut and following my intuition on where to go next. And I just let the road unfold before me.

Matt Bowles: That’s amazing. And I think that’s a great place to end the main portion of this interview. And at this point, Kelly, are you ready to move in? To the lightning round.

Kelly Lewis: Woo. Let’s do it.

Matt Bowles: Let’s do it. Alright, what is one book that has impacted you over the years you’d most recommend that people check out?

Kelly Lewis: Ooh, I just read a really good one called The Power by Naomi Alderman. So good. It was about if women were like actually electrical, women had like powers that men did not have. Obviously, I like that. And it’s just so good. Such a good read.

Matt Bowles: All right. What is one travel hack that you use that you can recommend?

Kelly Lewis: Pack two pairs of shoes and that’s it. Usually, I’ll pack a kind of flip flop situation and a walking shoe.

Matt Bowles: All right. Who is one person currently alive today that you’ve never met that you would most love to have dinner with just you and that person for an evening of dinner and conversation?

Kelly Lewis: My God. Can it please be Michelle Obama, please? Michelle, anywhere you want. I’m paying. Let’s go.

Matt Bowles: All right, Kelly, knowing everything that you know now, if you could go back in time and give one piece of advice to your 18-year-old self, what would you say to 18-year-old Kelly.

Kelly Lewis: It’s about, it gets so much better. When I was 18, I was still very much recovering from my childhood. I was still very much in that phase of having to feel like I had to overachieve to prove that I was good enough to prove that I was smart enough. If I could go back, I would just say it’s going to get so much better. And all you have to do is just trust that and trust your instincts and move accordingly.

Matt Bowles: Awesome. All right. Of all the places that you have now traveled, what are your top three favorite destinations you would most recommend that other people should definitely check out?

Kelly Lewis: New Zealand’s probably my number one. It’s my favorite. It’s my love. It’s where everything started. Argentina. Uruguay, Georgia. I’m like, can I keep going? I don’t know if I can fit over three.

Matt Bowles: All right. That’s four. We’ll give you four.

Kelly Lewis: All right. Let’s just stay there

Matt Bowles: All right. Last question, Kelly. What are your top three bucket list destinations? These are places you have not yet been. Highest on your list you’d most love to see.

Kelly Lewis: Guatemala. So, I’m severely lacking in my Central America and then that needs to change this year. So, Guatemala is my number one. Mongolia, I really, really want to go explore. And weirdly enough, Costa Rica, I think I’m maybe the only person that hasn’t been to Costa Rica. So, I’m going to make up for that. I’m sorry, Central America. I cannot wait to explore.

Matt Bowles: Amazing. All right, Kelly, I want you to let folks know at this point, how they can find you, how they can follow you, how they can learn more about Damesly, how they can read your book and anything else that you’re up to that you want folks to know about.

How do you want people to come into your world?

Kelly Lewis: So Damesly, if you’re looking for a group tour or workshop or retreat, definitely damesly.com. And then if you are interested in coaching, I’m also going to be launching some really exciting courses soon, including one on how to pitch and get paid as a speaker. So having been the organizer of an event for a very long time, I’ve seen a thousand good pitches and even more bad pitches. So, I’m going to be hosting a course on how to be a paid speaker. And I’m super excited about the things that I’m going to be developing in my own name and imprint, not as a brand. So that’s exciting too. I get to play around in business and see what works for me. So, I am gokellylewis all over the internet on com and anywhere else. So, if you’re interested in that journey, come on over and hang out.

Matt Bowles: Awesome. We are going to link all of that up in the show notes. So, folks can just go to one place at themaverick show.com. Go to the show notes for this episode. There you will find all of the ways to contact and follow Kelly, all of her events, her books, everything she’s up to will all be in one place at the maverick show. com.

Kelly, this was amazing. Thank you so much for coming to the show.

Kelly Lewis: I’m so honored to be here. Thank you so much for having me.

Matt Bowles: All right. Good night, everybody.