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December 19, 2023

The Art of Creating Incredible In-Person Retreats for Your Remote Company With Matt Young of Nomadic6

In this episode of Remotely Cultured, Jeanna chats with Matt Young, CEO of Nomadic6, about the art of creating in-person retreats for remote companies.

Matt Young is the Founder and CEO of Nomadic6, a network of coliving, coworking, and community spaces specializing in event strategy for distributed teams. He is also a founding member of Experience House, an association of experienced design and community-building leaders.

As an advocate for the future of remote and distributed teams, Matt has traveled the globe immersing himself in societies of people building lives of location independence. He and his team launched Nomadic6 while living in Thailand, and he continues his commitment to designing experiences for remote teams to reconnect in exotic places while independently living in some of the world’s most alluring locations.



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Here’s a glimpse of what you’ll learn: 

  • The why behind Nomadic6 — its genesis, mission, and goals today
  • Why building in-person connections for distributed teams is so essential 
  • How to design an A+ in-person meetup for your remote team 
  • What an ideal company off-site should consist of 
  • How to ensure your introverted teammates thrive during a company retreats

In this episode…

While working remotely offers a world of benefits, many remote-first employees yearn for the positive aspects of an onsite workplace, such as socialization and relationship building. So, are there solutions that allow these individuals to have the best of both worlds?

In-person retreats offer a vital balance to remote work, providing a space for employees to connect in ways that aren't possible through a screen. These retreats allow for real-time collaboration, team bonding, and the development of personal relationships, which are essential for building trust and understanding within a team. These in-person connections can boost morale, increase job satisfaction, and foster a sense of belonging and team cohesion.

Companies like Nomadic6, which specialize in organizing these retreats, play a crucial role in facilitating these benefits. They understand that while remote work offers flexibility and autonomy, it can also lead to feelings of isolation and disconnection. By arranging in-person gatherings, they help bridge this gap, ensuring that teams can enjoy the best aspects of both remote and onsite work environments. These retreats are carefully tailored to meet the unique needs of each team, combining structured activities with free time, allowing for both professional growth and personal relaxation.

In this episode of Remotely Cultured Jeanna Barrett sits down with Matt Young, CEO of Nomadic6, to discuss the art of creating in-person retreats for remote companies. He shares insights on Nomadic6’s mission and approach, the significance of these gatherings, and how to craft intentional meetups that address specific team needs and objectives.

Resources mentioned in this episode


Jeanna: Hey, everyone, welcome to Remotely Cultured. I'm your host Jeanna and calling in from Roatán, Honduras, where I run FPS and host this podcast. This episode is brought to you by First Page Strategy. At FPS we use data and big ideas to produce exponential growth for product-led brands who need to nail their acquisition goals and want to work with a flexible, non-traditional agency. For example, in one year, we've grown a client's revenue 197%, their organic revenue by 300%, and their paid revenue by over 1,000%. If you're a SaaS, FinTech or startup and need to hit your 2023 high-growth acquisition goals, check us out at firstpagestrategy.com. Today on the podcast we have with us Matt Young. Matt is the founder and CEO of Nomadic6 where they build in-person events for distributed teams. Hello, Matt. 

Matt: Hi. Thanks so much for having me.

Jeanna: Yeah. Nice to have you here. Fun fact, I was introduced to Matt through Running Remote, which is a really incredible community for remote founders, leaders and employees. So check that out if you're not a part of it already. But Matt, where are you calling in from today?

Matt: So I'm in Naples, Florida

Jeanna: Naples, Florida.

Matt: Not the Italian one.

Jeanna: Yeah. Right on. And what is it like in Naples? I haven't been there. And can you tell our listeners like what it's like to live in Naples or be working in Naples?

Matt: Well, that's a million degrees outside. I'll tell you that. 

Jeanna: Lots of AC?

Matt: Whether it's Celsius or Fahrenheit, I can tell you it's quite warm. But Naples is a charming little town on the west coast of Florida. If you know anything about the state, we're mostly known for Disney World and the beaches and of course, Miami. Naples is kind of tucked away. It's what you can say is probably the most Floridian town I've lived in. I grew up in Tampa, went to school Miami, I did live in Orlando. But Naples has this little bit of charm, in that it's very seasonal. The snowbirds, as we call them, everybody from the north fly in for the winter. Most of the economy here is based on tourism, or landscaping, construction services, things like that. And then they leave for the winter. And then we have the whole place to ourselves and it's kind of nice to be able to walk around the beach and nobody's here.

Jeanna: Oh, lovely. So big beach culture and do you like partake in any beach activities when you're not working?

Matt: We love kayaking. There's lots of intercoastal around here. A lot of, like, we see the manatees and sea turtles. It is sea turtle season. So there's Loggerhead turtles laying eggs all over the place. Otherwise, there's plenty of restaurants and it's very low-key. We go bowling a lot, bowling is a wonderful activity to do.

Jeanna: Something we don't have in Roatán, so I miss it. Right on. And how long have you been working remote?

Matt: Oh, man. Well, I guess the story of being a digital nomad starts as most people's I took. I took a traveling sales job after I finished graduate school that were really based on just contracts. So four four-week or six-week contracts. I packed up my apartment put it in storage and said I'll get a real life after this. And that was in 2015. So I guess I never really went back!

Jeanna: Yeah, cool!

Matt: So it's been a while since COVID. I have been more based in Florida. Kind of setting more roots. My family is here, closer friends are here. But that's why I built the business I built so I can kind of scratch that itch to go travel whenever I want to.

Jeanna: Yeah, beautiful. I think that's like you know, the the digital nomad thing. When it first started that term started right when I moved away from the US about seven or eight years ago I feel like and, I don't know, I feel like there's something to be said about staying put, laying down roots, but then being flexible to travel as much as you want and going places instead of doing that full-time and not having like, community and people to rely on and stuff like that. So I like that approach.

Matt: That was the biggest lesson I learned when I was really trying to think about that idea of setting routes. I came across the story of the traveler's curse. And the whole concept is, the more you seek or experience other people's version of happiness, the harder it is for you to find your own happiness.

Jeanna: Oh yeah, wow. 

Matt: So I think it's really in the people you're surrounded by, and that's been my focus since the last few years.

Jeanna: I love that. I feel like that is just like, the traveler's problem, right? Because I constantly think about something like that, because I feel like I truly am at my happiest when I'm experiencing another culture. So when I'm on a vacation, extended vacation, or a trip or wherever I'm at, I feel like there's a light inside of me that I don't feel like when I'm at home. And I think about that. Lately, I've thought about that a lot. Like, why is it that I feel so lit up around, like, you know, strangers and not my community than like, where I'm at? And I'm kind of personally trying to work on that. But maybe that's just like the travelers way, I don't know.

Matt: It's the curse of dopamine, the rush of new experiences, unfortunately. And being in the experience economy, that is what we sell. We're selling the adventure and the fun stuff, but it is good to be aware of what really makes you tick. What do you really find to be fulfilling in different ways? 

Jeanna: Yeah, right. 

Matt: A little more metaphysical there. We don't have to go there.

Jeanna: All right. That's another podcast. 

Matt: Right. 

Jeanna: Cool. So can you tell us about Nomadic6, and you know what you guys do, what your mission is, how you're capitalizing on that dopamine of experience?

Matt: Well, it all began once upon a time, I had just finished traveling China for a few weeks with a Zen Buddhist master, speaking of the metaphysical realm of life, and I had some time leftover from my trip that I didn't need to be anywhere, I was remote, I was doing my digital marketing thing at the time. And I said, well, I hear Chiang Mai is kind of like a mecca for digital nomads. And Thailand generally is a hub spot. Let's go check it out. So I ended up on this island called Koh Phangan. And Koh Phangan is now probably high on the list of nomad destinations. So I can say I was there early, if there's any credibility to be established. But in any case, I say this space called co-space, and it was my first time experiencing co-living and co-working in the same building. And having a little bit of experience from property management, and thinking about real estate as a business I wanted to get into, I just fell in love with the model.

Jeanna: Yeah. 

Matt: The idea that I can have all these needs met, you know that the idea of an office place to live and a community of people immediately by plugging in that share my lifestyle. Oh my god, sign me up. So I ended up making really great friends with the owner. Over the next few years, I managed the space, we expanded the business, we added two more locations, to the point where we had maybe 40 beds under our management. One of the units was or one of the buildings was a beachfront property. It was gorgeous, sunsets every day, it was a dream. But low season kills, as we all know. 

Jeanna: Yeah.

Matt: Low season is rough, and we started receiving groups, like a hacker's paradise. And when we, when we hosted that group, we started to kind of think about, well, this is another side of this business that kind of gets us off the island, maybe we put this in our back pocket and save it for a rainy day. That rainy day came, COVID, as everyone knows, we had to close up shop and get out of town. I kept the brand alive, Nomadic6 was just the name at that time. So this is December 2019, when we left Koh Phangan, and over the next couple of years, we were establishing kind of new relationships and thinking about new ways to kind of practice our craft of bringing people together. And then we launched Experience House. So Experience House was a collaboration with their founder, Sam, Sam Current, his name is, and it's just a playground for experienced designers and event planners and community builders to practice their craft. So you just use it as a sandbox to experiment with new ways of connecting people, brainstorm workshops, masterminds, all the above and we had a kick ass time. We were hiking volcanoes, going through the Sahara Desert. Nomadic6 was kind of the, we call it the back-end side of the business. So we were doing logistics and the accommodations. And all that to say that at the end of that experience, of Experience House, not to be redundant, we were kind of thinking about like, well, if we can take strangers, 30 strangers, and put them through a 30 day experience and see this community evolve afterwards, and knowing that the worst thing about Experience House is that it ends and we often go back to our lives, what happens if we work with existing communities? Let's call them remote teams, run them through maybe not as long of an experience but multiple experiences over a year or a couple of years? What happens over time? How does that business transform and how does that community transform and our hypothesis is that it makes a better business, it makes a better crew. So we pivoted to the remote world about a year ago, and we've been kind of slowly rockin and rollin, since. It's a game, it's B2B. But it's fun. It's great. And so far, it's really kind of proving to be true that in-person experiences are essential to remote operations or to remote organizations. 

Jeanna: Yeah, love it. Okay. I want to dig in a little bit later in the podcast and kind of talk specifically about like, our, you know, remote experiences at my brand and some of the brands you've worked with, and how other founders can take advantage of that. But before we go there, can you talk a little bit or share about the philosophy behind Nomadic6? On your website, you talk a little bit about co-living, the scaffolding arch, ten post experiences, like some of this stuff. So can you tell us like, what it is behind this philosophy that you're following to get people together?

Matt: So the philosophy of co-living is: shared space, shared time, shared resources. If I'm opening a co-living space, that is essentially what I am doing.

Jeanna: Yeah. 

Matt: Shared intention takes it one more level. If you want to have an eco-friendly co-living or a startup co-living, you can kind of take it to the next level. So that's like one philosophy that we always try to incorporate. That is what we're doing. We're doing topical livings with these groups. We're not bringing them to the Marriott or the Hyatt regencies. We're trying to build a campus experience a, I don't use the word compound, but maybe the compound experience might be the idea is that we have the space to ourselves, which is key. So when we talk about space, and our vision is that we're designing these these spaces for human thriving. And what I mean by that is the space checks all the boxes in terms of Maslow's hierarchy of needs, but goes one step further, and is ensuring optimal nutrition. So the food and beverage program is catered to each guest. There's physical state altering amenities, like saunas and jacuzzis. And there's plenty of activity and fitness and we're surrounded by nature. That's another big key here. Yeah, we're usually a little bit more remote, as opposed to being in a city center. And the vision, the idea is that we think no problem can be solved, or no problem cannot be solved, if people are able to thrive. And that's what we're here to do.

Jeanna: Love it. That's beautiful. Cool, cool. Okay. So let's talk a little bit about remote teams and why you think it's so important for remote teams to build in-person connections, like what kind? What does that do to transform the business and working relationships?

Matt: Well, coming from the remote world, as a digital nomad, and I've always kind of had remote teams, even when I was in graduate school, I had a full time job and in order to negotiate going remote, so I can take more classes, I basically sacrificed my raise and say, hey, you don't need to give me my annual, but I'd love to go remote. 

Jeanna: Nice. 

Matt: So I was kind of just starting like oh, this is great. Now I have more free time to like, go to school. But I did get immediately disconnected from my office. So the relationships and the friendships I had made, the buddies I had had at work, we traveled to New York, we did things we kind of just separated and we lost eye contact and said I got distracted with the school and other things. It just kind of reminded me or I always think about that experience of like, I can understand the perspective of the back-to-work movement, or back-to-office movement because you do want that for your team, you do want your team to have those natural friendships, those friendships promote career development, and feedback and mentorships. And these ideas that you can kind of talk to somebody about work without being afraid of being monitored or recorded. So you kind of want to make sure you have that space. While the other side, I will never work in a cubicle ever again. I can never do it. The office is constricting. The office is demanding. It's an overwatch kind of mentality. There's no trust. It's all about the intention. So when I think about in-person events for remote teams, it comes down to the intention, why do you want your team to come together? Well, if I want them to come back to the office because I want to watch them, it's a little malicious, it's a little — it builds a bad culture, as opposed to I want to do an event with my team in person because I want them to connect and be more of a cohesive unit and collaborate better or work on this particular project or even onboard new team members and show them what our culture is in person. That's a little bit more wholesome. Sign me up, right? if I work for a company that said we're doing a company retreat Barcelona twice a year. Absolutely. Let's do it. I love Barcelona. It's great. So that's it. 

Jeanna: Yeah. Cool. That's great. So do you think, like I obviously you think that there's some benefit here to get your team in person, in real life when you're remote to build relationships. Do you think there are certain things or is it possible to build those same relationships in ways when you're remote? Like certain things you can do when you're not getting in person?

Matt: Absolutely, it really comes down to awareness of the team. What we do during our onboarding process, after we sign and we're getting to work, we have a very extensive survey that we send out to the team members. So this is before we even start planning the event, picking locations, buses, all that kind of stuff. We need to know what the team's like. And we base it around our story arc, if you will. So the four pillars of every event, just kind of naturally organically follow these, these rhythms. And we built that into our programming, where we survey and ask, how connected are you to your team on a scale of one to 10? How's the collaboration, one to 10? How's the education of new members or career advancement, development? Things like that, one to 10? 

Jeanna: Yeah. 

Matt: Then finally, integration. How well is your work and your life, together? Is it conflicting? Are you taking phone calls at two in the morning, it's, it's make sure that —

Jeanna: Yeah, right. 

Matt: Yeah, we've all done it, but, right. So once we have a clear picture of that, from your team, we can start to kind of paint a picture and say, hey, marketing is really disconnected, or customer service has no education program, how can we start addressing that now before we get on site, so we don't have to use that time for other purposes? And it makes a nice little picture of how the organization's running. And then from there just coming up with strategy, right? If education is the goal, we're targeting the customer service team, assign that person, sorry, design a remote experience for that.

Jeanna: Love it. All right. So you're doing like some consulting a little bit about like, what kind of culture their company has before they get in person and like opportunities to improve it?

Matt: Absolutely. Some things we're doing with one of the groups we're working with now, we're having them build a playlist for the trip. So they're already kind of familiar with each other's like tastes. We did like a crossword puzzle, based on some of the survey results, where the answers were each other's names. First Name.

Jeanna: Cool, yeah.

Matt: Just fun stuff to kind of keep the engagement going. We were sending them riddles. We're just kind of playing. We're very playful.

Jeanna: Yeah. I love that.

Matt: We like to have the conversation going or to have the game going. 

Jeanna: Yeah, that's great. Get people interacting and talking before you all get in person and then meet each other. Some people meet for the very first time, right, which is always like, overwhelming.

Matt: Exactly. And that's what we noticed, too, is even from our side, we can kind of observe the team, watching them do the crossword puzzle and say, hey, these three or four people are really not comfortable sharing or asking for help, or whatever it may be. Let's let's reach out to them individually, schedule the one-on-ones, have them do little coffee dates, kind of like the Donut app. 

Jeanna: Yeah, we use it and love it. Yeah. Yeah, we use it at FPS. But then obviously, you and I were introduced that way through working remote. 

Matt: And it works! We're already doing a podcast. It's great.

Jeanna: Oh yeah! I weaseled that one in there. Okay, so you talked about how like a company retreat, their goal might be education. But what are some of those goals that you're, that companies are choosing that you are, that they can achieve when they're doing a retreat with you?

Matt: One thing we hear a lot, especially the companies we're talking to, is they've either never done a retreat before, or they haven't done one since COVID, or they've onboarded a lot more people. So it keeps coming up that they're new people, new connections, new, just new faces. So that's one and at the very least in time, or in-person time, is going to solve a lot of those problems. I usually advise to keep the groups smaller. So if you're a 100-person company, and you're trying to get 50 people, new people to meet 50 new people at the same time, it's going to be tough, and it's probably not going to work. We usually say, the longer the duration, the longer the bigger the group can be. If it's a week long, I like to say keep it under 30 and cycle the group. So maybe you do three trips of 30, if you're a 100-person team, for example. 

Jeanna: Yeah. Okay, so more intimacy. 

Matt: Exactly. And then it comes down to like, so that's connection. I think, making sure there's, we call it programmed unprogrammed time or unprogrammed program time, where you kind of leave space for the natural connections. So the between the events, the natural conversations that are really important, that's usually when people say they had the most fun is in the unprogrammed stuff. But beyond that, we have a pretty good network of facilitators and educators that could be flown in if you're looking for like a values workshop. And you want to not only build company values, but build individual values for your team and see do those align, which I do think is important work a company should do anyway. Do our team members even resonate with our values and our mission and our vision? What are they? What are their missions and visions in life? Having somebody facilitate that is just valuable anyway. And then you could go even further and say, do you want to have a shaman come in from India? If that's your company culture, absolutely. It just really depends on what you're looking for.

Jeanna: Okay, cool. And what, um, let's talk about like some of the structure that you give to these retreats and offsites that you guys are facilitating through Nomad6, like, what's important to do? And what's important not to do?

Matt: Our tent post experiences build the frame. So we call that, we call it tent posts because it's holding up what the experience is on the inside, in that we really design around the entry experience, a peak experience, and then an exit experience. 

Jeanna: Okay.

Matt: Over the week, that might be our opening dinner is usually kind of a recipe for connection. It's not just sitting down having dinner, we kind of break out some some fun stuff. I can't tell you too much because it's kind of secret sauce at that point. 

Jeanna: Yeah, that's okay. 

Matt: But in terms of peak experiences, that's kind of our main event, that might be the volcano hike, that might be the Sahara Desert, that might be some big workshop, it really depends, again, on what the intention is at the event. And then exit experiences, how are we closing out? How are we celebrating what we did here? And how do we take this home with us? Everything else in the middle, it's up to the team. So once we start to identify those needs and say, hey, marketing needs some education work in person or customer service needs some collaboration work. Let's build some sessions around that. So then Tuesday at four to six is going to be that for these guys. This for those guys. And we start to fill the calendar that way.

Jeanna: Okay, great. And so are companies doing this for like, their annual planning? Is there like a little bit more structured work involved? Or is it more like this is, we want to get you guys talking and having fun together?

Matt: So far, it's been mostly the connection aspect. There are, we do advise on leadership summits, and taking the time for leadership to also spend in person time together to think about these things. And even before our big events, use that time to think about what's what's the ultimate goal of our team retreat, for example. Other than that, we think about regional meetups, that's another thing we'd like to talk about, as in between the events between the big retreats, really, really knowing where your team is. So for example, location tracking is really powerful in that, you know, hey, we have six people in New York City right now, we should absolutely organize an event for them, call a restaurant, put a reservation in for dinner, and say, hey, you guys have a table at five on Friday, go hang out. 

Jeanna: That's great. Yeah. 

Matt: Stuff like that is always nice.

Jeanna: I hope to be, that would be so fun to be that big someday. We've had a little bit of overlapping because we're up to 35 at FPS. And so we've had like two or three people in Colorado or like, you know, someone's visiting another state someone lives in and they take photos together, and they share them and like that, like, warms my heart as a remote founder like. So. That's like self-facilitated a little bit now. So that's cool. It would be cool to be able to do that from like a company perspective, and like setup the connections for them. 

Matt: Sure. 

Jeanna: Something I'm interested in, because I've come across this like, as trying to get my team to connect or you know, hosting in-person events. What about, you know, in the remote company environment, there's people that are remote because they're introverted, and they literally have no interest in team building or care to be friends or in an office or like, desire to go travel to meet their team members. Like I have had experiences where I'm inviting someone, they're like, I really just don't want to do this ever. And I'm like, okay, like, I have to respect that. Right? So how do you like, what's the piece with the introverts? And how are you like folding in the introverts when it comes to the event planning?

Matt: I love this question because I am a raging introvert.

Jeanna: Really? Okay!

Matt: I'm an introvert that brings people together. I like to describe it as I always had a fish tank growing up, and I love fish tanks. I don't have one right now. But I think the metaphor of the fish tank is I love building the container so that all the little fish can play inside, the water temperature's nice, there's enough salination, that kind of stuff. That's kind of my thing. So when I think about other introverts and knowing so many, and that was one of the big pieces of advice I got from a really great experience designer. We were literally in the van on the way to the airport, it's just him and I chatting — him and me chatting not him and I chatting — oh, my grammar's off today.

Jeanna: I'm not gonna judge on your grammar!

Matt: Him and I were chatting about this subject and he pretty much said, design spaces for introverts because nobody does that. Nobody thinks about these guys. 

Jeanna: Right. 

Matt: And I wholeheartedly agree. So when I'm talking to these guys, I'm thinking about that intentional downtime. It's not necessarily intentional downtime to connect, it's intentional downtime to go recharge, to have those spaces. When I think about space design for human thriving, there's also like little nooks and crannies. And I think of my spaces, my little, I call them my little caves that I usually find at venues, that might be perched up, a little reading room or this one library room is off limits for these few hours. And that's a place to go recharge and just be to yourself. Generally, we try to give introverts like a private room too by end of day, so they can always kind of have their space.

Jeanna: Yeah, that's a big one for me. I'm an introverted — no, I'm an extroverted introvert. 

Matt: I think introverts, introverts can be extroverted, if it's something that they're interested in, or in terms of conversation, or something they like to do. My partner in crime, she's a raging introvert, and it's funny, I like to plan events, and she doesn't want to do any, like she doesn't want to go, but every time she says, I'm so glad I went, that was so much fun. So we just have to know that, yes, I know the reluctance. I know that feeling of I don't want to do this. I guarantee you that you're gonna, you're gonna love it at the end of the day.

Jeanna: Yeah, I just I'm someone that just needs like the recharge space, right? Like, I don't want to share a room with four people. Like I don't want to be with people from 8am to 8pm. Kind of a thing.

Matt: Absolutely. If anything we break it down in percentages and say really are our trips are 40%, free time, 30% work, 30% for activities. So we really make sure that there's the free time to connect, but also the free time to recharge.

Jeanna: Yeah. Love it. Then what should founders of remote companies like myself, and you think about when looking at an advanced strategy for their distributed teams?

Matt: It's all the above, we wrote an in-person event strategy guide for distributed teams, which I'm happy to share.

Jeanna: Yeah, please do, I'll put it in the show notes. So people can find the link.

Matt: Perfect. And it really just breaks down all this stuff, right? It has from the very base level, location tracking, so you know where your team is, which simply having a community manager, it could be a volunteer from your company, or maybe a member of your team just keeps track of that kind of stuff. So that you always know, hey, so and so is going to be in London next week, let's make sure they meet up with the London team or the London crew. Up to regional events. The next level being like, hey, there's five or six people in Spain, let's just do a Madrid meetup and of coordinate that where we're, it's this mini retreat. So you might have a Spain retreat going on, a New Mexico retreat going on, etc, etc. Just kind of making sure that you're giving people that are nearby the opportunity to connect. Leadership summits, of course, definitely take time for leadership to do your thing and connect with each other and get on the same page. Usually around quarters is good. Setting all that kind of stuff. Conference strategy, what conferences are you sending people to? That's another great opportunity to send four or five people from your team to represent your company, which is how we went to running remote and met all these amazing people. And I got with my business development guy for the first time in person.

Jeanna: I missed you. I was there! 

Matt: Oh, you were there? 

Jeanna: Yeah.

Matt: There's four hundred people, too. Yeah. It was a great event. Next year.

Jeanna: Oh, yeah. Oh, man. Like I well, just excuse to go to Portugal again. But I had so much fun. Yeah. It was really well done.

Matt: I loved it. Yeah. And that's something I think most companies should think about is, what,  what conferences are good for your team? And your market? Right? 

Jeanna: Yeah, at least one, right? Because we've kind of gotten to like, we've peeled back going to conferences after COVID. You know, not a lot of companies go to conferences anymore. I feel like now people are just kind of starting back, get back out there and go. So it's like, at least put one in your budget, right?

Matt: Absolutely. And then the off-sites, right? So then we're talking about the big company, the trips and retreats. I am always a little, I think I haven't quite formed my own opinion on full company gatherings. So there is that tried and true conference technique of, especially for bigger organizations, having their 2000 employees come together for two days. That's a huge event. I think that's something that could be a lot of fun and could be really beneficial from an information-sharing perspective. But it's really not going to achieve any kind of connection. Much of it, anyway. 

Jeanna: Okay, so yeah, you guys are focusing on kind of highlighting that you need to keep the group small, like really foster intimacy and like vulnerability between teams so that you share those like those moments, right?

Matt: Absolutely. You might be a 2000-person company, I still recommend breaking it up into teams. And then if you want to celebrate the end of the year with 2000 people then go for it, I think that's a lot of fun. But if you're, if your goal, the intention of the event is to connect people keep it small.

Jeanna: Cool. All right. Um, before we wrap this up and go into our final three questions, let's do like a mini case study kind of thing. Like I would love to tell you about what we did with our retreat last year and you can just dissect it and tell me like maybe how we could do a better job next time.

Matt: Sure. And that's, that's great. And I'll tell you did a great job. 

Jeanna: Okay! So well, there's always room for improvement, there's going to be something in there, but maybe maybe I'm perfect. You never know. Um, okay, so I hosted our first in-person event. I have my company started, FPS started in 2016. And so it's a little bit late, but it was like, you know, we only started hiring full time people in 2021, we had this new leadership team, and we wanted to get together, it was basically a leadership summit for us to do some annual planning. And I took them to San Miguel de Allende. And we did actually, like, I think it was five days and we did, one day we're coming in, and we're kind of, you know, settling in and going to dinner together, a welcome dinner thing. The next day, we did one day of our, of our leadership planning. And then we had two days kind of off in the middle where we all did Dia de los Muertos together and got dressed up. 

Matt: Oh, that's fun. 

Jeanna: And yeah, had that kind of shared experience, so that might have been what you would consider to be our peak experience. And then, after the recovery day, and from that, we did the last leadership day planning, and the goodbye dinner. And then we left the next day. So that was our — and there's only five of us there. It was very small. So ask me questions, What could I have done better?

Matt: Well, I love the idea of building it around a festival. That's something that's, that's pro-level planning. If you can figure out how to plan an event around a festival where you get to experience something that culturally rich, bravo, yeah, that's fantastic. I'd love I love that opportunity to make something like that happen. So I think there's a plus for that.

Jeanna: Thank you. The only way I pulled that off, by the way, because like cultural like festivals, that is my jam, like I will travel to any frickin festival and across the world. The only way I pulled that off is because I'd done it before by myself. So I kind of I knew the like what to do and how to do it. And I don't know that I would have done it just like going in blind trying to take my team into like a blind festival. I didn't know how it was gonna go.

Matt: Right. I think that's the caveat. That's where we say we always like to have a local liaison when we plan something. So generally, we say we don't want to take a group somewhere we've never been or we don't have anybody that's ever been to those places. Yeah.

Jeanna: That's a great, yes. Okay. So that's a great piece of advice. Yes. Like, I felt very uncomfortable this year going into trying to plan a new one. I was like, Okay, where can I take them where I've been, and I know that they're gonna have a good time. But then the traveler in me is like, but I want to check another box.

Matt: It's such a, it's funny, because sometimes you have to surrender the process and trust that liaisons going to be there and handle everything. But assuming is always the danger. Right? So in this situation, I'd say you nailed it, because one, you've been there before, you've already experienced it. So you knew that everyone's gonna make it through okay. So in terms of risk management, another A+. That's kind of something people don't think about too is what are the risks? And if anything, I'm really not the fun guy. I'm the risk management guy. My team are the fun people. I just kind of push them in their direction, but I'm thinking, Well, what if something goes wrong? We've had broken arms on trips. 

Jeanna: Injuries, yeah, yeah. 

Matt: Where's the nearest hospital? What's the volcano eruption evacuation plan? These types of things you kind of should think about. Travel Insurance, things like that.

Jeanna: Yeah, I mean, that's important. I think, I like yeah, that's really important stuff to think about as well, because you want people to have a good experience. You don't want someone to go home like, yeah, with a broken leg or worse.

Matt: Right, exactly. So you're missing items that have sold and stuff. It's just things that kind of happen, but you have to have a plan for it. So I would say that's always something to consider when you're planning a retreat. Let's have that we call it a kind of a risk management meeting, if you will. We do it like couple weeks before the trip, and we just kind of sit in and say what's everything that could possibly go wrong? 

Jeanna: Yeah, right. 

Matt: Brainstorm. Throw it out there. And say alright, what happens if this happens with that? We give it like a one to five. How likely is this to happen? 

Jeanna: Yeah. 

Matt: Meaning if it's a five like this might actually happen.

Jeanna: Like the volcano erupting? 

Matt: Yeah. And maybe we shouldn't go.

Jeanna: What about length? Like, what would you say about the length of what we did? Like I think we were there not counting the travel to and travel away, four days, like what's the optimal time for people to be on a retreat?

Matt: Well, you're talking about genuine community building. Nobody, no company has ever taken the bait just yet. But our events used to be 30-day trips. 

Jeanna: Wow!

Matt: 30 days is a long time, but what it does is, I mean, the reality is, you can be anybody you want to be for a week, after 30 days, the real you comes out, the vulnerability comes out. 

Jeanna: That's true. 

Matt: And you get to kind of know, you, that's when the community builds. And that's when you, that's where our hero's journey, we call it the connection, collaboration, education, integration. I observe that during those 30 days, because it just happened naturally, like the first week was all about connection. The second week was, all of a sudden people were collaborating and working on new stuff. 

Jeanna: Yeah.

Matt: Then there's education, people are teaching — oh, I actually got that backwards. I'm sorry. It was connection then education, then collaboration, and integration. Week four. Oh, my God, this is ending. How do I take this home with me? Which was always the hardest part, because 30 days goes by so fast. I know it sounds like forever. And everyone that said, oh, my god, I can't sign up for 30 days. That's too long. I can come for a week. They always extended they always stayed the whole time. Yeah, it's just, it's just what it is.

Jeanna: Oh, man, I love that. That would maybe be my dream. It'd be really difficult, I think, in a company where you have a lot of people to have families.

Matt: Absolutely. So that's where we're coming from. 

Jeanna: Yeah, but I love the concept. 

Matt: Right. So a week is really ideal. I think of an ideal company trip. It's something like, arrive on a Monday, fly out Friday. Or if you're traveling from further away, what we advise is give more time for like international people that are going to be jet lagged. Get them there like Saturday or Sunday before the event, have a few more days for them. And then same on the other end, give them a few extra days. We also like to offer or coach, or advise that you leave space at the end. So if somebody says, hey, I just kind of want to stay another couple of weeks in Honduras. Can you just book my return flight for later? Yeah, absolutely. It's their trip, it's their time. 

Jeanna: Oh, that's a good idea. 

Matt: Maybe five or six people, maybe they want to stay, maybe half your team does want to do 30 days together. And then you're like, sure, just have the return fights ready to go. It's just up to them to coordinate everything else, which is kind of where we can drop our seat a little bit, too. If your team wanted to extend five or six of them, we would help kind of facilitate that.

Jeanna: Right, cool. I love it. So there we go. There's a good critique of mine, I could have done a lot, I need to do my retreats longer than four days.

Matt: I say the bigger the group, the longer the duration. So it sounds like you were just a few of you guys. So five of you for a week. I think that's pretty good, right? It's kind of like a dinner party. Where, in The Art of Gathering, if you've read that book by Priya Parker, she talks about the group sizes. 

Jeanna: Yeah. 

Matt: And if you want to have, for example, a dinner party where everyone's having a joint conversation, you have to have less than six people, five people at a table, you're gonna all, you're going to be part of the same conversation. As soon as there's six or more, there's going to be separate conversations. And you see it every time. So we break off here, break off there. 

Jeanna: Yes. 

Matt: Same with group dynamics. If you really want your five people to connect a week is totally fine. But if you start getting up to that 6, 10, 15, 20, 30 people, you should think about longer duration.

Jeanna: Cool. All right. Great tips. Thank you Matt, that was a good convo about how to have in-person connection when your remote company. Final three questions for you before we call this GTG. What is your work from anywhere item or tool that you could never live without? You can't say computer.

Matt: These headphones. 

Jeanna: Okay, specifically those headphones what are they?

Matt: They're noise canceling just boys, Bose headphones. Boys, ha. Bose headphones. With a little plug so I could plug into the airplane media guys. And it's, they're so comfortable. And they fit my head so well, yeah, I have to have these. 

Jeanna: Okay, so Bose noise-cancelling headphones. Right on. And do you have like a remote work productivity tip you can share with our listeners?

Matt: Productivity tip? I have a, I do have a daily practice of managing not only my own, like practices, but my work practices in that it's like a daily download. We can call it a daily journal. But I'm doing kind of more check-ins. So I'll do like a mind dump of everything that's on my mind right now. Including things that need to get done. What's on today's agenda and things like that, but also have a checklist of did I schedule by exercise today or do I have an intention to get to the gym today? 

Jeanna: Yeah. 

Matt: Am I gonna get this thing done today? How are my deadlines? I just kind of, I asked myself, well my form asked myself these questions. And it's a yes, no, yes, no. And I'm very lenient with myself. Usually.

Jeanna: So you built a form to ask yourself these questions?

Matt: I can't take full credit. My buddy Andrew Cruzi built this self-mastery system. This is a whole nother conversation. 

Jeanna: Okay...

Matt: But it's just this, it's like gamified life, where even if just by staying consistent with this like daily uploads of your work life, your your personal life, your fitness, mental health, etc, etc, etc. You start to see it over time.

Jeanna: That's my jam. I have to have him on the podcast.

Matt: Oh my god Andrew would love talking about it. Yeah.

Jeanna: Cool right on okay. And if someone wanted to go learn more about you or Nomadic6 where should they go online?

Matt: Nomadic6.com. We're on LinkedIn, we're on Instagram, Nomadic6 with that number six, so one letter or one word. 

Jeanna: Yeah. Cool. All right Matt, thank you for your time.

Matt: No problem. Thank you so much. This was fun.

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