Hidden Gems, Big Adventures: LGBTQ+ Travel In South Dakota With Daniel Milks
Who says you have to leave the country to find adventure? In this episode, we’re heading to the Black Hills and Badlands with Daniel Milks, the awesome founder of My XO Adventures — a tour company that’s all about uncovering South Dakota’s best-kept secrets. Daniel gets real about his journey from globetrotting to building a thriving, LGBTQ+-owned business in a spot you might not expect. We chat about what it’s like being an out entrepreneur in small-town America, the magic of storytelling in travel, and how AI (yep, AI!) is shaking up the tourism world. Expect laughs, inspiring stories, and a whole lot of heart as we explore what it really means to find community — and adventure — in unexpected places. If you're craving LGBTQ+ travel that's way off the beaten path, this one's for you!
For our viewers:
Any listener that books one or more tours with My XO Adventures will receive a 15% promotional discount using the code PRIDENOMAD upon checkout. The reservation must be booked by February 28, 2025, and is good for any tours reserved from today through the end of the year.
Contact Daniel:
Listen to the Podcast here
Hidden Gems, Big Adventures: LGBTQ+ Travel In South Dakota With Daniel Milks
From Sydney Studio To Travel Tales: Daniel's Nomad Journey Begins
I’m thrilled to see like a real mic and stuff. It's awesome. I used to live in Sydney and I had a full studio and put everything in storage months ago. The camera, mic system, lighting, and the backdrop are all in storage.
This is the basement of my home and everything that's down here is from my travels. All the textiles in the back and I've got hats on the wall that you can't see over. Behind my computer, I have a tapestry for Ecuador from the Kachwa who invited me into their homes. When they all work together, they call it the factory. They produce amazing textiles. Everywhere I go, I try and get something. Not the typical kachi item but something meaningful. In this particular room, I'm surrounded by my travels, so it makes me feel good.
That's one of the biggest challenges that we as digital nomads have because we can't buy stuff. I've got a year, is the plan now and it's with this backpack, which has my computer and shit and a roller board. That's it. You got the big thing on the wall back there, the head. I was in Thailand years ago and I found this gorgeous Elephant head carved out of wood at the night market in Chiang Mai. I wanted it and I couldn't buy it. What I'm going to do travel on the piece of wood? Having this home base with it is nice.
I've tried to make it like everything is a story. If you're going to get something, it should invoke a story or a memory in your head and it sure does. It's like this is me room.
It's nice. Sometimes, when I do these things, we've got the ironing board in the background with the diapers on it. This is nice. Most of your travels have been where?
I've traveled extensively through Europe, parts of Central America, South America, and all over the US. I don't know how much about me, but I have spent nine and a half months in a van being a digital nomad if you will during the pandemic because that's what I had to do to survive. There's a connection there in the name and what I've done. I ended up out here in South Dakota at the end of that journey not knowing where I was going to end up.
It's because the Badlands National Park was the first park to open in the National Park system. I made my way from Erie, Pennsylvania, my home town, down this direction slowly doing like doing a videos on covered bridges in Ohio, in Gary, Indiana on abandoned buildings and photography, video, content, and graffiti art and then into the Badlands. I spent the first night in the Badlands camping.
Around somewhere on the same time, was the movie Nomadland being filmed in the Badlands. That's where that whole thing takes place in the Badlands. That's how I ended up here was by being a nomad during the pandemic because travel was not happening. Everybody wanted to refund. I almost lost the business at that time. It was tough, but that's what I did. It was the best year of my life.
Since we’re in that topic, what was the core business before the current evolution? Where are you now? Give me that story.
I'll tell you it but I don't want some of it broadcast. There's company names I don't want to mention but I can go into my company. I opened up My XO Adventures.
My XO Adventures: The Meaning Behind The Name & The Love Of Travel
What's the significance of that of XO?
The XO back in August of 2018 when the company started, I had to think of a name of what it was going to represent to me. XO might seem unusual, it’s a representation of love and affection. I chose that because it represents the love of travel and that's my tagline. It’s for the love of travel. As if it's like a book about to open up and go into some wonderful journey.
That's a nice backstory. I love that. That's great. I’ll share mine then since we're sharing that. My company is Seagrass Media. Now, we published the Pride Nomad Letter. The thing behind Seagrass is that when a hurricane hits, and I used to live in Saint Croix in USVI and I lived through Hurricane Hugo, which was hell of a thing. I was in the mortgage business and homes I’d financed, in the morning were gone that afternoon.
It was pretty horrific, but guess what stands? Even though the concrete houses blow away, the Seagrass still remains. It goes with the flow. It's got a solid root system and knows what it is, but even when it gets tramped down because of the storm, the sun comes out and it's back up again. I produced an event back in 2015 called World Love Week™. I own WorldLoveWeek.com, which is all about love and business. The XO resonates.
It also gets the people to ask, what is that? Even in my line of business, stories are a big deal. It opens up a story to tell somebody about it. It is a good opening at the beginning of an experienced year about to have.
Stories are what sells. With our brand, Pride Nomad is about travel because as nomads we travel but at the same time, we’re still doing business. Whether our audience is either working for someone else on a remote job or entrepreneurial. The key to any business is the story and that's what gets people engaged emotionally to buy.
We were just talking about that before we started but think about yourself. You are a story. I'm a story. Everything that is in the background is a story from somewhere that I've been and I've surrounded myself with these stories. For people in my line of business, which is a bit different but for tour managers and things like that, you do have to be able to tell a story in a good way and not in a rehearse way. That's like from the heart and it just flows from you. I love that part of this business.
I was on the website. It's a gorgeous website, by the way. I like pretty pictures.
There was a lot of blood, sweat, tears, and fist holding too getting it to that point but thank you. I appreciate the compliment.
There's always backstory to that. Let me ask what. What's your specialty because there are people that are reading that aren't familiar with you? What is the specialty of XO?
From International Dreams To Black Hills Realities: My XO's Evolution
Originally it was where it was designed to be small group international travel company. It is not at the moment but it will be very shortly again, which is exciting. I would specialize in going to places that people usually had traveled extensively or enough to where they were seeking something different. I would design a trip like that. We used to go to Cuba, for example. We were just talking about Ecuador. Not Ecuador in the sense of Keto and the Galapagos, but getting in with the culture, learning, and maybe even volunteering and things like that.
It was small group travel where people were vetted. You knew you were going to be with a good group and intimate experiences that were meaningful and impactful and life enriching. From that, as we were talking about before when COVID hit, it kicked the legs out from underneath that. Now that's coming back. I am located in Rapid City, South Dakota and I am in the Black Hills, which is a beautiful place in South Dakota. If you're going to be here in South Dakota, that's where you want to be. The Black Hills are gorgeous. To a contrast, that is the Badlands, which is a whole different ecosystem and environment in of itself. I'm far North. It's chilly outside now, but beautiful. I do love it here. It's a great place to live.
Most of the stuff you recommend is Badlands, is that primarily the tours you've been running?
People might pick up on a couple of things here, which is Devils Tower or also known as Mato Tipila or the Great Gray Horn. Mount Rushmore is something that people have on their bucket list usually somewhere and they want to see. Those are two points that people go, “I know where that's at,” because they don't know South Dakota to well.
In between all of those things are the ancient Black Hills, the sixth oldest mountain chain in the world, canyons, spiers, and some of the most amazing roads that you've ever driven, Iron Mountain Road and Needles Highway. It is fantastic. It has a rich history from first nation or indigenous people here and also settler history. The contrasts around here are outstanding. You can drive ten minutes and you're out in the country. You're away from that traffic. You are you are like one with Earth. It’s that much out. There are trade-offs being in South Dakota but it's beautiful.
I expect that when you want to tour of South Dakota, your curating it. You're people are seeing the stuff that they need to see as opposed to the stuff that they don't want to be experiencing.
In my tours, they're a bit different. We don't do that. What you're referencing is, let's just say, your general good representative of the area. I’m going to tell you this and look over here and this is what we want you to think about this subject.
Navigating LGBTQ+ Acceptance In South Dakota: A Candid Discussion
I was thinking more in terms of any, I'll use redneck as perhaps a term. Those that are not accepting and so on of the LGBTQ+ Community. I was at an event in Orlando and there's people in the room that were wearing Manga T-shirts. That's why we created the whole Pride Nomad brand. That's what I was considering. You’ve got the ecosystem of acceptance and community versus being afraid for your life walking down the street and being an Andrew Shepherd.
We are pretty close to Wyoming, and I will admit that South Dakota is a tough place when it comes to that thing, the LGBT community and those topics that surround that subject. However, I would say that, first of all, we don't have Manga T-shirts and hats around here, believe it or not. It's assumed. You don’t see a lot of that. Maybe a flag here and there at somebody's front yard or whatever, but I personally have never had an issue here in South Dakota.
If you're going to get something, it should invoke a story or memory.
The thing about this area that people should know and the gay community is that there's a libertarian type spirit out here, which is a live in and let live. Do many people feel that being gay is a sin, for example? Yes, I'm sure but out in the community and making my way through the community, I don't feel uncomfortable. There is not much of a gay scene here. There isn't a bar you can go down to or a huge Pride Fest. Although, there is one.
It's not that, but that's not why I moved here. I didn't move for the for the gay scene. I moved here because I just love the land, but it is a tough sell for the gay community because that's what they think. It’s exactly what you just said. People should know that South Dakota certainly is open for business to the LGBT community, and you're looking at the guy right here.
It's important. It's interesting because I went to Africa years ago and a couple of times. I went because I read a book by Danielle Laidley. I forgot the name of the book but the whole concept of it was when you are in the Savannah and you were with the elephants and all these other animals. These guys are the King of the jungle or of the whatever the animal world. It humanizes us and the majesty of that. Part of me is like, “Being in this environment with the beautiful environment. It does create a whole other experience.”
At the same time, when I was in Africa, being gay was not a conversation. It was not part of the experience at all. There's not a gay bar in the Sinara. Not experience at all unless we bring it in with the gay tour. To me, it's not the conversation and that's why I want to address it because we want to support the tours that you do and at the same time, I've never been there. I've spoken of South Dakota in the most states.
You're having an invite. Come on out. I'll show you around.
I'm all in. I just going to find the time. I've never been a Mount Rushmore. I want to see this stuff and I want to do videos. I want to tell the world about it. This is cool stuff. People need to experience that and then experience it in an environment that yet is exclusionary. Whether it's a bus, on bicycles or whatever it is, that the person next to me, I can kid with.
Here's one of the reasons why I'm doing this. My mom and I did a bus tour of Ireland a lot of years back. It was a great trip. We had a lesbian tour operator and that was it. It was my mom and I, and this lesbian tour operator. Everyone in the bus is straight and it wasn't that they weren't inclusionary. They are just freaking boring.
That's fair.
It was dull. We didn't do this because it didn't monetize for us but we created fam-friend adventures. It was going to be gay guys and their moms. Can you imagine a bus of gay guys and their moms on it? Everyone wanted to play. It’s like, “Can I go, too? My mom's dead but can I come? I'm not gay but it'll be fun. Can I come, too?” Yes.
I can imagine that because I am the gay guy and his mom because she's been on trips with me that we discussed before gay themed trips. It's hilarious and she enjoys it thoroughly.
My mom's 90 and we traveled together. They like her better than they like me. That whole element was amazing. Having something that's freaking gorgeous which what you're showing people. We want to definitely provide photos and all that. Having that and having tours that you can have fun with and you're not just seeing breaks and then you're bored because you can't relate. That's an important experience.
Personalizing The Journey: Private Tours & Daniel's Approach
It's a great subject, by the way. Thank you for bringing it up, but as it relates to my business, we do private tours. There's no such thing as 50 passenger buses or anything like that. The largest vehicle I have holds fourteen passengers. Anytime somebody books, it’s a private tour. You are not mixing with anyone. You have purchased that vehicle for the day and me and cheap.
You’re a call boy. It’s what it is.
Yes, exactly. I do everything. Everything has a price. You have an invitation. Remember, I gave you an invitation.
Every inch of Daniel Milks, you can buy him.
I didn't know this was going to be that kind of show now.
It's all about engagement.
It wouldn't be right at gay show if something like this didn't come up.
A friend of mine who's been like the biggest fan of the Pride Nomad brand was yelling at me. He said, “Ken, you're doing these videos on our YouTube channel. Are you like running a gay show or not because I can't tell that you're gay or that you're markets gay. You've got to let people know.”
I can tell that you're gay.
Thank you. I’m like, “I don't know how to do this.” Thank you. It’s great. We wanted it to be fun.
That's a key element of any trip that you're going on, certainly if you're designing it or if how to design one. In my past and I still do, fun is the element that must occur through the whole thing. It's a big part of it. It's a big part of the memory. You want to laugh and enjoy it. When you were going back to your travels and you were saying that there wasn't a gay bar in the middle of the Messiah.
It's something for the gay community to understand from my point of view. When you travel and your first few times, you don't maybe get this but after a few moments, you start to understand things out in the world are very different than they are in the United States. We live in a fantasy land, honestly. When you travel, for instance, to the Middle East, or, let's just say South America, which is a very religious area in the world.
First of all, you abide by their laws and you understand where you're at and act accordingly. When you are out and out, let's say in a religiously conservative area. It wouldn't be a good idea to flaunt anything and you want to blend. You don't want to attract a lot of attention and that's just smart travel. I don't think you have to do that in South Dakota but there are limitations no matter where you go. Maybe they're just a little less in San Francisco than they are here or in Wilton Manors and Fort Lauderdale. When the LGBTQ community visits, the people here are not going to be heckled. They're just not going to. It's a matter of respect all the way around and that's it.
An intimate experience is one that's meaningful, impactful, and life-enriching.
Taking this to years ago when I went to France for the first time. People said to me that the French are rude and this and that. I happen to love France and I love the language. I didn't learn Spanish in high schools. I learned French. I was there and sincerely wanting to be there and trying language and everyone was friendly, loving, and caring about pronouncing this. They were laughing at me and with me wasn't. It wasn't like an ugly American. It was like you're cool because you're sincere. If we travel with that in mind and are respectful. With all due respect to my Australian friends.
Australia is the best to travel with in my opinion.
They’re fun but they can be loud and obnoxious.
You mean like to get drunk? I think that’s what you’re saying.
Yes, and I don't drink.
Neither do I.
My husband at the time and I, and this is before we could have husbands but I say that because everything was that way. We're American.
We have to disclose that. It used to be that way.
We’re just married. I don't get that. It's like we didn't want to be lumped into that obnoxious category of the drunk Australian and mind you, I freaking love Australia. I can't wait to go back, but the thing that I want people to remember is that when we do travel, we are representing us. We do need to be respectful of meeting people where they're at. We've come a long way in America not far enough and other countries still have to come a long Thailand just to approve in gay marriage and stuff.
Travel is so important with that, so I'm thrilled that you're doing international travel again. People need to see us as wonderful, cool, and fun people that they want to go to. When we see the straight women want to go to the gay bars because we're more fun and have better music and even the straight guys come along. That's amazing.
Creating Change Through Engagement: Representing The LGBTQ+ Community Abroad
I love what you're talking about. I want to say that even back in the beginning of when I was in travel and going to some places, they were clearly not approving by majority of the LGBT community or whatever. We got some pushback on traveling to those areas but along the lines of what you were just saying, is the way that you create change in the world is by engaging with it. If you're going to engage with it, you have to understand what the playing field is and engage on that playing field according to those rules so that they have an opportunity to get to know who you are and who the community is and that there are just okay. They're alright. How can you get there any other way?
When you said you do volunteer stuff, I was at the IGLTA Convention in Osaka and there was someone who wanted award. Part of what they do with their tours is a lot of volunteer stuff. It's important. So much of it is certainly for the experience of us as volunteers. I did that when I was doing some Tony Robbins stuff. Volunteering is so much fun, especially with kids.
It makes you feel great.
I'm dropping all these things and I don't mean to, but it's part of my journey. I was in Indonesia a couple years ago and we went to the school. We gave them school supplies. What we were doing was throwing tennis balls at each other. We were like having tennis ball fights with the kids. It was the most fun ever. That wasn't a gay group. I was the only homo of the group but feeling joy.
If we're doing it as a gay group as an example, LGBTQ+ group. They're seeing us and they're not feeling threatened. They're like overcool and the kids of the future of the world, both everything. The more that we're out there, the more that we do that, the better. If you bring that experience as you are to people on your tours, how much fun is that? It's something you never forget.
As a community too outside of travel, we've gone through. We were talking about marriage before and then he was your husband but you weren't legally married. I know those days. Even then when the gay community was moving forward, there was a lot of joy and a lot of happiness even though there were restrictions on who we were. Over the last, maybe let's say ten years or so, we've been very busy with fear and anger.
To your point of volunteering, it's important that we re-engage in that path that we set a long time ago and get aligned with that to learn how to laugh and get along, engage with, have fun, and represent again of who we are, which is a vibrant, colorful, amazingly, talented and beautiful community. The world needs to know that and the world, believe me, wants to know those things because this is not just us that feels this way about what's been going on lately but the whole world. Volunteering and putting a smile on somebody's face does make a difference in the world.
It's interesting you're saying that. We're going a little bit off topic but fuck it. One of my side businesses is a company called 123Nonprofit. We take for profit businesses. We set them up with a nonprofit and then we get them Google ad grant because nonprofits get $10,000 a month from Google for free every month. It's pretty cool. Anyway, one of our new clients, who's become a dear friend. His mission was not just to not to get $10,000 from Google. He wants to help kids. He wants to help gay kids.
We're putting together a program that will look like Richard Branson's entrepreneurship program in South Africa. What we're looking to do, we're setting up a Mastermind within the Pride Nomad community with a whole bunch of entrepreneurs. We want to have that community come and teach in little entrepreneurship centers to help the gay kids. We can't restrict it to gays, but it'll be LGBTQs and embracing it because a friend of his back in the day could not come out to him.
He didn't come out to the friend and the friend and committed suicide. There's a lot to do with that. Doing stuff with kids, empowering kids, and volunteering along that way changes the world. Only because you're talking about volunteering, I want to hook you up. His name is W, because all of us can do that and with tours that way, it makes a ship and makes a change. It's pretty remarkable.
It's like a self-feeding circle that keeps going. It makes you feel good and makes them feel good. It changes the world. That just keeps going around and around. It's just not like cliche or whatever. It’s true. This is these things we need to believe in again.
I was going to ask you what’s inspiring you but I think you just told me.
Representing The Gay Community: Building Relationships & Changing Perceptions
It is an element of my tours because as we were talking about, I get a lot of people that are very conservative. That would be expected here. When I first came out here during COVID, there were political vacations or revenge vacation. You could say, “I'm getting out and doing this thing.” Your customers or your guests are in all my tours because I've never had an all gay. You need to be gay friendly to be on my tours.
When we do international stuff, you have to know how to communicate. This is just my personal philosophy, I feel obligated to represent the gay community of whatever place in their journey that they are. It's not my job to go beyond or do not enough, but to show like, “This is who I am and it's okay.” A lot of straight guys think you’re attracted to them immediately because you're gay or something like that. Don't flatter yourself. Even beyond the ecology, biology, and geography and everything else of the area, I'm creating relationships with people and that's very important. Somebody might leave the tour and say, “I don't believe in all that stuff but that Daniel, he's okay.” That’s better than when they came.
That's exactly right. I don't think we want to wear our rainbow flags in their face because you met people where they are. That's why I had this conversation with my friend. It's like my people need to know that that Pride Nomad is gay. I’m like, “I thought it did.”
I’m looking at your shirt. I'm pretty sure that people would know, but people know.
I'm not sure where you’re coming from with that, but I have to process and figure it out. The point is, when I teach, I teach whatever it is because running an ad or creating a lead magnet is creating a lead magnet whether you're straight or gay or bi or tri or whatever you are. I don't care.
You and I don't get the lingo exactly.
I'm old enough now that it was all gay. Gay included lesbians, transgender, and bi. Now, I still trip over the syllables. It just takes it too many syllables to say LGBTQ+.
It's just like math. We learn math the different way. They do it different now. It's hard to understand.
My mom and I were talking about this. I'm like, “Mom, the younger people like to call it queer and includes everybody.” I think it does. She's like, “I don't like that word.” I'm like, “I don't either, mom, but you're 90. I'm 67. What we say doesn't matter. That's what it is and it doesn't have the same meaning anymore.”
Kids have different languages. Now I learned what rizz means and stuff like that. Have you ever heard that one?
No.
Let me bring you into the conversation.
Also, to our older readers.
This is for whatever generation. Maybe thirteen or something like that. It means charisma but that's just one of probably hundreds of words. There could be a dictionary that is just all new words. When you and I talk and say whatever we say, they don't understand. We have our own language, too.
We're old people. It's like, “Baby, I'm a daddy.”
Speak for yourself. I like that term better.
I never considered myself that. I lived in Bangkok for like 8 or 10 years and they love older men. Some of them want money from us.
How much money?
It's like, everything can be bought. There is hope. I got a friend and I think he's hitting 90. He's living in Thailand. He's got a 26-year-old Filipino boyfriend. He could not be happier.
I'm sure. I'd be happy.
In every conversation, he’s like, “My 26-year-old Filipino boyfriend is wearing me out.” I'm like, “Okay. Thank you.” Anyway, back on topic. How are you because you want to attract more business from the LGBTQ+ community? How are you attracting them? We're doing this and we want to help get you promoted. What are your strategies for getting more of the market?
Aside from like statements on our website and belonging to different organizations that are LGBTQIA supportive, which we are. I'll just be honest, it's still hard. It's difficult to be perfectly honest with you to develop a strategy for someone like me in this area exactly for the LGBT community and to go gangbusters on it. It will not yield good results. It just won't.
The way that we market ourselves is being open and honest. On our Google business profile, you can see that we're LGBTQ owned. We find that the people that want to come to this area are like what we were talking about before were it's always been on the checklist Mount Rushmore but they hadn't yet gotten to that point.
They're going to come here and they're going to look for an LGBTQ friendly company. They're just going to do it. We're here for them, but now, to be perfectly frank, it's difficult. It is difficult to get the community. We've advertised in Florida and California and things like that, but you have to piggyback on the flight routes and where they go to because otherwise, you're just throwing money out the window and marketing dollars. This is exactly how we would let people know who we are and there is a welcoming company here that's going to show them a great time. It's just a little amount of time.
AI & The Future Of Travel: Data, Personalization, & Innovation
There's some great ways to target market. I just finished this whole three-day program on this. There's some technology and we'll have access to this shortly, so we will talk. Also, for everyone watching, while we're talking travel, the fact is those that are traveling still have to pay the bills and I mean as a traveler. If we're running businesses, for example, we still need data. The key to everything is data.
We're going to have access to people that are searching if they're searching for Black Hills or for South Dakota or for unique interesting vacation. We know who they are. If we can communicate with those people directly rather than blanketing the market. I'll give you an example. We're running this Summit in March. It's called the World Playground Summit. We'll have 75 speakers all about how to run a digital nomad life. We want to bring on Amex as a sponsor, for example.
You don't want to attract a lot of attention, and that's just smart travel.
Now, to me, because we're we have a market of people that are LGBTQ+ digital nomads or those who want to be. These are people that have money, love to travel and will spend a fortune and could use an American Express card if they don't have one already. Amex has sponsored a number of pride events. They've got the banners and they got the little Amex this or that but that's not targeted. They have no idea who they're talking to other than the gay community. What we've got is data. We know who you are. We have your email address.
You're starting to sound like Mark Zuckerberg now. Data is everything, isn't it? It is, and this is something that anyone who's reading that is in the travel business or digital nomad, AI is going to change the world. It has already but by the end of 2025, we're going to see exactly how powerful of a change it is. We are using AI in many of our efforts as well and understand the importance of it in what you're doing and what I'm doing. If you don't think it's important, you're going to miss the boat here because it's revolutionary.
Here's a scary stat. I think it's 5.4% of all American businesses are only using AI in any of their business.
I just read that somewhere, too. We might have read the same article. Honestly, I can't believe it and in some ways, I don't even want to talk about it. I'm like, “Good. Let them be that way.” If you're not playing with ChatGPT, just play with it. If you're not doing that, you're missing the boat. If you're not learning how to integrate that with other apps and programs and put it onto your website and deal with it in your marketing. I created a video from Surah and it was hilarious. It was a rusty old bus with people that were sharing a tour and they were miserable looking out the window and here comes a My XO Adventure vehicle.
We'll talk about that offline, too, because I know about it. I didn't know that it was available yet. I'm tickled. There's so much more with that. The lesson for all of you watching, if you're not playing with AI and those technologies, you need to. Its what's part of our business model. There's some members of the community that are not and we have all these resources.
We have a full CRM that's completely AI powered that does a massive amount of stuff. Basically, it's white label of one of the best CRMs out there. It's called Zenware AI and it's ours. We're customizing a lot of that for our community, which will be ridiculous. What it's going to do is ridiculously, especially with the data. It's crazy. That's allowing us to power all this stuff.
Balancing Digital Nomad Life: Technology & Enjoying The Moment
I have a question for you, though. I'm curious. As a digital nomad, when you deal with the technology that you must deal with on a daily basis and with AI coming in and opening God knows what Pandora's box. It's going to be things we can't even imagine. How do you make sure that you have time to enjoy the place that you're in and do this at the same time because isn't that important to do?
A great question. That's one of the things that I'm so bent on teaching within the community in terms of running businesses that run for you in the background. Years ago, I was in Barcelona with my mom and I had added webinars to do. I was on deadline for stuff and she wanted to go see the Gaudí Cathedral before I got finished. She and I have seen it before but I couldn't go with her because I had shit to do. That's troublesome.
My model should be that we run 2-3 hours a day of that and then go play. When I moved to Thailand, I was I was in Pattaya for a couple weeks and my deal was, in the morning, I worked two hours, went to the beach for a few hours, came back after the beach and worked an hour. Went to dinner, went out after that to the shows at the venue with best drag shows and then come back and work a little bit more or maybe I got distracted because I got lucky. It was a stand of stuff. What do you know?
You got to taste the local food but you're right. AI Powers it better. Running the newsletter, for example. I run the Pride Nomad letter. It comes out every Tuesday. It allowed me to be able to do research and be able to write better. Even some of the stuff I write by hand, I'll take that writing and pop it into ChatGPT. I have the Pro, the 4.01 now.
That's what I have, too. It does get to know you, though, too. You don't have to explain it after a while. It knows your personality. With AI and the things that you're talking about, the one thing that I would say I'm cautious about is any technology that we've ever had is supposed to make your life better and easy. We're seeing AI do all these things that are amazing and making things that took us hours to do. It happens like that, but it’s going to add shit to this then it's going to become a lot of work to work with if you're not careful.
Here's the cool thing and we're we could go on forever with this. This is going to be a little longer episode that I want because we're supposed to be done now.
It's going to be worth it, though.
I freaking love this. This is the best thing ever. I spent three days at an AI conference and I just came back. I'm filled with this. There is AI agents that will talk to each other that will do much of the work for you and for you particularly. When you're doing a tour, you can't talk to people. There's AI voice agents that will answer the phone for you and talk to your customers and interview them about what tour they want because they've got all that information. It can be your voice. It's crazy what's available now. It's not even creepy if you do it the right way. We have this technology exists now and I can sell it to you right away.
I would love to hear about that.
I know we had the capability. I have no clue how to set the damn thing up, because there's so much.
It's like mapping a pathway and you're hitting all this stuff that’s relevant to your business and it just goes on. It's amazing what's happening up there.
The thing with all this AI stuff is it's added so much. One of the benefits that we have within Pride Nomad, we created something called Pride Nomad Concierge. The idea of the comes here is, we're scraping the web of everything that we can find that's related to gay and digital nomad stuff. We've been doing it by location just to keep things simple. Soon our automation will take place. We've been doing it manually.
If you want to go to San Francisco, you go to the concierge, “I'm going to be in San Francisco for four days. Give me an itinerary.” It does. “We're can I go for yoga?” “Here's the five top gay centric yoga places that have been referred to us.” Now, we can do is we can run ads to that as well because we're setting up a directory. All is powered by AI. You're the first one to hear this. We're building this global directory called the Prime Nomad Hub, where we will feature you and other tour companies.
The idea is that we're a central resource and AI makes it possible. Ultimately, it empowers us to do that and help everyone but the key to all of it is we can't lose sight of who we are, of the integrity with it and not making bullshit stuff because it should be helping us and not controlling us. That's the beauty.
That's the caution that I say. That's a yellow light there. Be careful because it can become overwhelming. From your end, you're looking at connecting these different resources around the world. From my end too, for those that own a business out there, it's about how to position your business so that AI can understand it and pull these things from you knowing exactly what business you are and what you do and how you're set up. It’s having the tools in place for AI to get that.
It's artificial intelligence but it's getting smarter and smarter. The thing, for example, for you and I look at this because I've been consulting businesses for years and training businesses for 40 plus years. We haven’t even talked about that because you’re like, “You don't know my backstory.” This isn't about me. This is about you.
The thing is, what it allows us to do from a data standpoint, not just in terms of learning data but customizing things for everyone because here’s your beauty. You do customed tours for folks. If all someone does now is your AI agent, asks your callers, “What appealed to you about calling us?” “I always wanted to see Mount Rushmore. I heard cool things.” “What cool things did you hear about?” It can do all that and then would you like to see this or that or this? It can design the damn tour for them while you're out giving someone else a tour. That's brilliant.
I just get a little list that says, “This is what they want to do,” and out we go.
AI is already changing the world. By the end of this year, we'll truly see the magnitude of that change.
Exactly. What's interesting and we'll get there. I don't know that we're there now but we are.
Pop it into Google Maps and it would put all the coordinates in there.
Where I'm going, Daniel, is we have their phone number and their email address. Therefore, we can then get into this massive ass database, which comes from the credit card companies, this and that. All the stuff is amazing. We now know your income and all this stuff, so we can craft things that do matter to you in a sense of who you are, where you go, and what your interests are so that we can craft tours that are that specific to you. It's like someone read your mind.
Years ago, before AI craze which I would say has been happening for a while but been in the public for like about a year. They were talking about Google has this this digital workup of you. They understand who you are. This is true, people. This is what AI is only taking and putting steroids into it. What they want to know is just like AI is structured to guess the next word in a sentence what it's going to be. It's wanting to guess your next move on how you feel, and what I can put in front of you that you are willing to purchase based on that mood. That's how it works. This is what's happening. It's not fake news. This is real.
For example, we can put your email list into a query and it will come back and tell us not so much specifically but like, “This person earns $50,000 a year.” Your email list of say 50,000 people, 40% went to university, 32% own their homes, 15% are married, and 12%, have kids. We can bake that here's the kids group. Here's the university graduate group and so on. How is does that marketing?
It's incredible. By the way, these things work well for businesses but let's be fair to the consumer here, too. I'm in the middle of removing that data of myself because the data aggregators are the ones that have this stuff or if you've got emails in your inbox that you haven't deleted forever or whatever it might be.
For someone who doesn't want to be known as well as that, there's also companies on the other end of this that are trying to prevent that from happening as well. From a business standpoint, this is an amazing and incredibly useful tool. Something I think like for guests of mine, if I get in front of them, they're getting the right person. I'm patting myself on the back, but they are getting.
You should. You have to believe that and all of us that are in business have to believe that. They also have to believe it, too. Again, this is generic. The more you know about your customer, the better because some of the folks are not aware. I didn't know that much about South Dakota. I'm like, “South Dakota?” How many more people are there out there like me?
Everybody. That's the fun part of the job. It’s because they come in and they think Mount Rushmore. They're like exactly what you said, “South Dakota?” I get to show them South Dakota and that is nice to surprise somebody around every single term. I got to have that little thing in there, too.
That's why smart tour operators bring on influencers so that they can run all their stuff on their social. One of the cruise companies brought a few people I know to Antarctica. These are expensive trips, but they were comped in because guess what? All this on Instagram now is, “Me and the penguins.” Now, I'm having envy. I want to do that trip, too. I've always wanted to go there, but having people talk about your stuff, and there's some software coming out that we should be talking about.
By the way, the penguin thing. If somebody hasn't done like a gay penguin themed trip. It's laying on the table right there now. They're always the animal. They say it exists. They have gay couples in penguin.
I am so in running that. I think it was a “gay trip.” The point is, I'm doing a press run to the Whistler Pride and Ski Week. They gave me a press pass and everything. What events are you going to cover? All of them, especially the swim thing because I want to see boys and Speedos and get frustrated. That's the thing, when you get someone enthusiastic, they'll tell their friends.
I'd been looking for money out of it. They just want to tell their friends because it's fun stuff. If you are in the media, it gets you eyeballs. I'm looking forward to coming up and visiting you because aside from just the business side of it, I want to experience this. This is cool stuff. The biggest challenge for us as nomads is seeing everything and seeing everything to be immersed in it. That's the key.
For me, I wouldn't do it any other way either because that the type of tours that we do, and this might seem like a long time for somebody but they go from 8 to sometimes 12 hours you're with them. You're not rushing but you're making sure that they're seeing it is much about the place that you that I love they're going to see and it just blows them away as the time goes on. It goes by like that. My favorites were one of them. The way it ends is sunset golden hour in the Badlands and then it goes into the blue hour and these beautiful shapes inspires that were these giant like butts and what looked like mountains turn into silhouettes.
You make your way down through the park and we lay out in zero gravity chairs and look at the sky because it's a dark night sky park. We see the shooting stars, the satellites, and the comet a while back. Sometimes, the Aurora Borealis. I have seen more Aurora Borealis in 2024 than I have in a lifetime. It is an incredibly unique experience. It isn't the, look out to your left and look out to your right and let's go. Now, it's time for potty stop thing. There's so much to see and to do. People who love travel, that is what they want to do, but it's hard to find sometimes the right person as you said with your cruise. I don't want to go on the cruise unless you're there. You're in important ingredient.
Unique Experiences & Tour Duration: What To Expect With My XO Adventures
That's what makes it fun. I got a couple more questions then we got to land the plane. The first thing is, what's the typical length of your tours? I know it's 8 to 12 hours a day, but the one day or two day or three days a week. What's the normal?
It depends. If you make a mistake, it's one because a lot of people come into South Dakota and they're going to Yellowstone in a combination tour. They might not look at it hard enough and they'll come in a day early. They have a very short period of time but the ones that look at it and understand a little bit more and if they have a chance to speak with us, so we can explain.
You should plan in this area of South Dakota, which is the Black Hills and Badlands, at least three full days of tours because you've got the Northern Black Hills and Devils Tower, the Central Black Hills that has Mount Rushmore and Custer State Park and the Bison. You've got the Badlands, which is in the other direction and is another day if you spend it right, if you get it, and if you are having a wonderful time and experience. That's the minimum. I would say, including your flight days and stuff, 4or 5 days would be a good timeframe to experience the area.
I was going to say we should probably coordinate like a 3 or 4-day whatever tour that is sold as a product.
There are some campgrounds here. A lot of people don't remember this, but like purple roofs and things like that that are friendly. We're working on that now too, which is not just to bring somebody in who's LGBTQ and get them in our favorite hotel, which we do have our favorite but to consider doing something of a buyout and bringing in a group of folks and maybe some entertainers and having a good time that way.
That's what I'm thinking and we can talk offline about maybe creating some of that stuff because my goal for all this is to use the framework of what Pride Nomad is as we build a community to empower that. You can seek and have that because that would be super fun. While there may be thousands of gay tour operators or gay friendly tour operators, every tour is different, every person's different, and every environment is different. There's room for everybody.
I have a Monopoly on this area though.
I think you probably do. I love this and then we got to close it up. Here’s the thing, it is that having that niche. Owning South Dakota, for example. Very few people are doing that. We're the like the only gay digital nomad thing out there, which we’re happy to have, versus I could go digital nomad just by itself. First of all, I don't want to be in that that space but having that marketplace. I moved to Saint Croix in the Virgin Islands years ago. I was the only mortgage company there. They were banks, but I was the only mortgage lender that could do that business.
Isn't that a great place to be?
It was amazing.
Here it is true. I'm the only gay operator that's out. We have other fine companies here. I'm not saying don't, but I'm the only one that's LGBTQ owned.
Meet Amy: The Heart Of My XO's Customer Connection & Future Plans
We are predominantly a loyal community that if I have a choice of four operators, I'm going to the gay one first. I know you're doing an incredible job, but you may not even be the best. They're not looking at that. They're looking at who can they feel most comfortable with. That's important. The next question is, you got to just woman sitting behind you that's been on the stairs watching us the entire time on camera. Who is this fabulous person?
That's Amy. That's who I was talking about earlier. Amy is my mom. She works for the company as well. Anybody who calls in and is making a reservation or wants recommendations and advice and things like that.
That's me. I take care of the front end of it and make sure that people understand what's available out here and how they can enjoy their time out here because as Daniel said, most people are thinking Mount Rushmore and they're just trying to squeeze it in. When you come out here and the one thing that they say when they're leaving is, “If I had only known, I would have spent more time.” I get them to spend more time right up front so there's no regret.
She's been in sales all her life, so there’s that aspect of it too. The cool part about being in sales is when what you're saying is 100% the truth. It's easy to sell because it's true. That is what it is.
It’s because love it and I believe it. Any chance I get to go out on a tour, I'm out because this area is just spectacular. I moved out here a few years ago from Florida and I never looked back.
I'm even more psyched. Daniel get the hell out of here.
She’s just like your mom.
I know. I'm like if she can bring her scooter, we're in. She now has scooter.
I don't need a scooter yet, Ken, but I will go hang with her.
She's 90. She took a spill in 2024 with me in Sydney. She's on a scooter but you can't stop her. The woman is impossible. She's a crazy.
I love the idea of the mom and son.
I'm not sure the site is still up. That wasn’t my primary business and I couldn't monetize it. Frankly, a friend of mine told me years ago, “Ken, you talk about wanting to do these trips but the fact is you want to be on the trip. You don't want to run the trip.” I was like, “You're right. I don't want to deal with something that's not happy with the bed.”
If you're gay and you've got a cool mom. They're the best moms. Gay moms are okay with it and everything like that. They're the best, but I'll bet you that there are some people out there that are both cool moms that maybe don't have a son. We used to have a name for those but we are not going to say that. Also, maybe guys or ladies that either don't have their moms anymore or maybe they're not approving and they need to be adopted.
We'll have to talk online about that, but there's a lot of merit to that for sure. I know there's a market for it for people that are in the travel business. That's not my business. We want to empower the travel folks rather than compete with them because I get to Switzerland. It would be a freaking a hoot. I was thinking, when we were together during the day, we're seeing all the stuff. At night, we go out to the gay bars or whatever and the moms do their stuff and everyone's has a fabulous time or vice versa. Whatever.
That would be crazy. It’s so much fun. As I was telling Daniel, I think you were still on the stairs at that point. At first, I didn't know that you were gay or not when we first started. I was like, “Is that his wife? What's the deal?” Here we go, but I had friends. When I told them about what I was doing, they're like, “My mom's gone, but can I still come?” Sure.
I had my non gay friends that were like, “I'm not gay, but this sounds like too much fun. Can I come, too?” I’m like, “Sure, 100%. As long as you as long as you're crazy like us, you can come.” That’s why it was called Fam Friends Adventures. I think there's a huge market there that we could play with for sure.
There has to be and identifiers in that club, too. When we would go to Cuba, we would make everybody wear these sunglasses and the scarf like the purple hats. Something creative.
For sure. We crashed the plane. I have people that rented a car to come see me and I'm like, “You're waiting.” This has been way too long, but so much fun. Daniel, thank you. By the way to reach you, we have coupon codes and there's discounts and all sorts of stuff that you arrange for. Thank you. I want you tell everybody about what that is because that's important.
FYI, we just launched PrideNomadAdventures.com which we're going to want to post everything you've got in that site. I'm saying this publicly and we'll talk offline about the mechanics of it because you’re the first to hear about it. We also own LastMinuteGayTravel.com and DiscountGayTravel.com as well.
You hear important news first in South Dakota. I just want the rest of the nations to know that's typical.
I’m first to hear it better than New Hampshire. Tell everybody what special stuff you're doing for our community that's important.
I've given you a link and that's going to give you a percentage off of your tour depending on what you decide to do with us. I will personally be your guide coming into South Dakota and make sure that you have a fantastic time. We provided a link with the information on that and different codes that the people that are reading this can use as long as they have PrideNomad as the promo code when they check out.
We appreciate that. Remember, if you paid attention, Daniel said he can be bought. Depending on what services you need. He will make you a happy trip, but Daniel has to take care of mom. Don't do it Daniel. Do it for mom. This has a slice of heaven. I appreciate your time. You have made this so much fun.
Thank you. I've had a great time, too.
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About Daniel Milks
Daniel Milks, the heart and soul behind My XO Adventures, turned a lifelong passion for travel into a career of creating unforgettable experiences. Having explored the world and learned through mentorship and hard work, Daniel combines his expertise and personal touch to design tours that feel less like guided trips and more like adventures with a friend. His attention to detail, storytelling talent, and commitment to excellence set My XO Adventures apart. For Daniel, it’s not just about showing you a destination—it’s about creating memories that last a lifetime."
