Is Nearshoring the Smartest Way to Build a Remote Team in 2025? | 🎙 The Nearshore Cafe Podcast

Welcome to another episode of the Nearshore Cafe Podcast. I'm Brian Samson, your host. Today's going to be a great show if you are thinking about hiring an executive assistant, a virtual assistant, really some leverage and how all that comes into play in Latin America. Before I introduce our guests, let me thank our sponsor Plug Technologies, plugg.tech. Great way to connect talent all over Latin America with US companies. Without further ado, let me introduce Josh Allen Dykstra, CEO of WorkRevolution. Josh, great to have you on the show.

Thanks for having me, Brian.

Josh, we've talked a couple times and you're known throughout the industry for your keynotes and really the mission that you've been focused on most, if not all your career. Maybe let's start there. Just give a little, a little bit about, uh, your, your mission and what's been driving you all these years.

Yeah, sure, sure. So, uh, initially I thought I was going to do music. So I grew up as a classically trained pianist on stages and churches and recitals and stuff like that. And so I always knew I liked to be on stages. And so, you know, as I got into high school, picked up more instruments, then, you know, got into college, started writing songs, forming bands, right? And so kind of left college with this idea that I should probably be a rock star. And, uh, so I decided that would be a good good plan and moved to Los Angeles and got a management deal and shopped the record labels and recorded the albums and did the gigs and then realized pretty quickly that I actually did not want to do the music business. I love music, but I did not like the music business. So I had this quarter-life crisis, dark night of the soul. I was like, what am I going to do if I'm not going to do this thing I thought I was going to do? And so I reflected on all these jobs I'd had as a musician. And what I noticed was that when my job was better, my life was better. When I had a good manager and there was a good culture, it affected the rest of my life in a positive way. And then on the opposite side, if it was a crappy manager and it was just like, that was really interesting to me. And so I did a little bit of research, realized that this isn't a Josh thing. This is an everybody thing, right? Everyone is just completely, we're just so impacted by our work because we spend the majority of our waking lives there. So of course we are. Then I did a little more research and realized, oh my goodness, most everybody actually does not like work. Most everybody kind of hates it, or at best they feel kind of meh about work. And I was like, that's really dumb. Why did we build a life like that? And so I've devoted, so it's been almost 20 years now, but I've devoted my career to trying to make work not suck for as many humans as I possibly can. And that's, I'm kind of like a serial entrepreneur in that space. So like everything I do has been like towards that mission. But yeah, I've done a bunch of different companies, right? Consulting firms and training coaches and consultants and tech companies and all sorts of things, but always after this idea. Of how do we make work life-giving instead of life-sucking.

Love it. Let's actually dive a little deeper step by step because I think that shapes the narrative later for how you might have thought about Leverage. But if you could start the first couple companies, what were they? What were you doing? All that. Yeah.

Okay. Yeah. So when I was transitioning out of music and into this thing, I was pretty enamored with this notion that people could get paid to speak from stages instead of sing from stages, which very few people get paid for that. And so I thought, oh, that's interesting. And then you could write books instead of write songs. So it was just like there's this world of performance art inside kind of a business context, which seemed like a much more reasonable way to actually pay my rent and buy food. So I thought, that seems like a good idea. Strangely, I didn't end up actually doing that stuff, like being on stages as a speaker for quite a few years. The first business that I ended up doing came out of the great financial crisis. So I went back to school, got an MBA, focused in leadership. I'm not a finance MBA, but I went, so I got out of this with a shiny degree, right? I graduated in 2009, right? So like right into the middle of the financial crisis, not really having any luck finding a job, but fortunately some friends from grad school brought me in to work with their companies. And so I became a consultant kind of accidentally. And so I started consulting around leadership and culture and employee engagement and positive psychology and strengths and how to do more of what you should, right? And more of the things that are right with you and that bring you energy instead of the things that are wrong with you and that suck the life out of you. And so I started doing a lot of consulting, a lot of workshops. I did a lot of little stages, right? Like, small groups of people that I got to speak with and to. And that's what I did for almost a decade is mostly consulting and workshops. In 2012, I published my first book, first business book. And so then I started actually getting on more stages. And it was slow, right? It was slow going and it was always kind of on the side of my consulting and workshops business. And then I ended up doing a TED Talk in 2018 called How Work Can Heal the World. And that was a pretty transformational experience for me. And then after the TED Talk, I just totally stopped speaking. This was not a very smart business move, but it's kind of what I needed. I had been on the road now for over a decade. I was pretty burned out on business travel. My kiddos were little babies. We had just moved to Denver. I wanted to be home more. And so I just stopped. I stopped speaking and I built a business where we trained coaches and consultants. So we trained 300 or 400 coaches, consultants, and HR people inside companies and out. And then, I don't know, about 6-ish years ago, I got this crazy idea to build a tech company. I thought, you know, this is a big problem, right? People do not like their work all over the world, right? There's hundreds of millions of us that experience this kind of disconnect. From loving our work. We just don't. And so I thought to meet the scale of this problem at kind of the scale of the whole, you need something exponential like tech. And so I was like, I'm going to, I'm going to build some technology. So this is like, you know, 2018 or something like that, 2019. So man, Brian, I thought, I thought we had it right. I thought, cause we were going, cause then the pandemic came and I was like, employers are like, oh, we need digital stuff. We care about flexibility, work from home. We need more tech products to help with this. We care about your burnout. That was the message for a couple years. I really, and I thought we were building a unicorn and I thought we were building a billion-dollar company, but it was not to be. When the tailwinds kind of switched to headwinds in 2023 or so and people started demanding return to office and we were just, we were underfunded. We didn't raise enough back in the day. And so I learned a lot of valuable lessons. And yeah, when we closed that company down last year, I really thought, what do I want to do? And speaking became my thing. That was what I wanted to go back in because I didn't do enough of it back in the day. And so that's primarily what I do now is speaking and thought leadership. Yeah. Yeah.

Back to your tech company. I remember those, the years of quiet quitting and everyone resignation. Yeah, the great resignations.

Totally.

More, probably twice as many jobs available as there were people and—

Yep. Yep. It was just a, yeah, it was such a market for employees. It was so, that was such a rich time for people, for labor, right? For workers. And then, yeah, to see it kind of flip pretty hard in the last couple years has been that's been an interesting bit of whiplash.

Yeah. How would you describe the market today for labor?

You know, I think what we're still seeing a lot of this whiplash effect kind of, you know, it's the pendulum has swung back, I think in the other way. In a lot of ways there's still, at least here in the US, right? There's still a decent amount of, you know, get back to the office kind of stuff. Yeah. And we've got all this office real estate and, you know, we, we try to make a good case, or leaders try to make a case saying that this helps collaboration, or we do our best work when we do it together in person. And the data really doesn't bear that out as true, but it's a good talking line for the reporters, I guess. But Yeah, I think, I think this kind of like hybrid remote thing is, I think it's here to stay, at least in people's psyches. People, we just can't experience that kind of freedom and flexibility and then go back to the way that it was before without some pretty serious psychological consequences, right? Like we don't, I don't think a lot of people want to do that. And that's not really a great recipe for employee engagement to be forcing this thing, but we'll see how it we'll see how it plays out.

Josh, when you were running your HR tech company, did you only hire in the US? Did you have people kind of all over the country? What did that look like?

We were totally spread out. And my other companies, so my service-based companies were actually fully remote. So we were those kind of like distributed remote, you know, kind of, we were that kind of company, you know, before it was cool, right? So, or before it was necessary, we were, we had really kind of learned how to work on Zoom and in Slack and build a really cohesive culture remotely and virtually because we were just— my business partners at the time were in Kansas City and I'm in Denver, and then neither of us were going to move to the other place. And so it was like, well, I guess we've got to figure this out. And then when we started hiring people, we always just hired them from, from anywhere. It just kind of made sense, right? And we weren't limited by geography at all. So kind of at our peak, we had just about 20 people and we had people, yeah, all over the world. We had people in Austin and we had people in Israel and we had people in Brazil and Mexico and we had people in Venezuela and just got, yeah, just like all, I think, I think we were across, I don't know, 4 or 5 time zones and yeah, it was, it was a really, it was a cool adventure.

Yeah. What did you learn or maybe, you know, what kind of advice could you share to leaders that are building remote companies and they've got people in different time zones, different countries, and there's the leadership part of that and there's also the management part of that.

Yeah, I think that one of the most important things to think about when doing a remote thing is that you have to just be so much more intentional about something like culture, right? Because what happens in an office, and I think this is maybe one of the things that office people have, office leaders, office-based leaders have struggled with is that they're conflating culture and office because when you're in an office, you can actually be kind of lazy about culture because what happens in an office culture is people have natural collisions, right? They can stop by your desk and you might run into each other in the hallway or in the bathroom or the water cooler or in a cafeteria, right? These collisions kind of happen organically when you're in the same physical space. And of course, that doesn't happen if you're spread across 5 time zones. And you only meet on Zoom. So the biggest thing I would say for leaders of remote is you have to just be very intentional and thoughtful about the culture that you want. You're going to have a culture, right? It's going to be the kind of the outgrowth of you as the senior leader or as the founder, right? You're going to kind of like imbue this company with the things that are important to you. And you just have to be really thoughtful about if that's the way that you actually want it to be because some of us have really quirky ways of doing things or we have learned some bad habits from working for bad managers or whatever. And so you can absolutely build a world-class phenomenal culture entirely remotely. You just have to do it in a very intentional way.

How would that come into play when it's US only versus like, you know, you had people in Israel, you had people in Texas, you had people in Latin America. What were some of the nuances that you had to keep in mind with that?

I think one of the things that we did really well was to celebrate not just company culture, but culture, like culture, culture, right? Like all of these different rich cultures from all of these different places in the world. What we did, we ended up having a culture meeting once a month. This was one of my business partner's ideas, was to really try to like deliberately celebrate and learn about, hey, what are your holidays in Venezuela? What are you like doing today in Israel? What are you like? Right. So it's like we tried to open up a space or create a space and hold a space for people to be able to share and celebrate the things about their culture that we would maybe would not know or understand, or, and that was really rich. That was a really rich time for us. There's, there's so many things where across the world we want the same things.

Right.

And I think that's the other thing that I learned very clearly from, from doing this is there are many things that we all just, we, they're the same that we want. We all want respect and dignity and time off and flexibility and the ability to be with our friends and family and, and, you know, be able to work in our strengths and, right, like that stuff is true no matter where you are in the world. And then there's also these really unique things that I think is really important to celebrate the uniqueness of the different cultures. And so I say it's kind of like both of those things, like appreciate all of the similarities that we have. And then celebrate the places that were different. And if you can do both of those things, you'll have an awesome, awesome culture no matter where your people are. Yeah.

And then just with all the different places that you operated in, you had team members in, it sounded like it was an intentional choice of good talent can be anywhere versus say like, okay, we're going to be US-based and Venezuelan-based and all of our non-US people will be in Venezuela. Can you share a little bit of like how that thinking kind of came to be? And did you debate that at all internally?

That's a great, really interesting question. I don't know that we ever even really talked about it in that way. So some of our core values as a company, and we called them vital behaviors, but some of our core, these really core belief system kinds of things that we organized around, our very, you know, one of our very first ones was to start with energy. And what we mean by that is that we start the conversation like that. The way that we start our dialogue with people is to start with what brings them life and energy. And so when you start with that frame, it just doesn't even really come up where they live. It just doesn't. It's kind of irrelevant. It's almost like a degree. Or something like, I don't really care if you have a degree. I don't really care where you live. Can you do the job? And like, will you be energized by the work you need to do? And do you align with our values? Then it's great. But yeah, it's really, it's funny because we never, I don't think we ever even had a conversation in that frame of like, where should we hire people from? It just didn't matter.

Can you think back to the first time you hired outside of the US and like just the mechanics of it? You know, like how did you, like, did you go to Upwork or agencies? You know, how did you guys even start? And I'm sure there's, you know, uh, business owners, startup founders that are listening and they're like, this sounds interesting. Like, like what's the first step? What's, what's step 2? What's step 3?

Yeah. Yeah. So. Initially, and I don't remember how we got connected to these folks, Brian, but somehow we got connected to a group called Virtual Latinos. And that, that was our go-to for a while. And they, they did us real well, right? They found us some really amazing folks. And yes, but we always went through an agency like that. So there was a couple projects here and there that we've, we've done over the years through like an Upwork where we contract directly with the person. But yeah, more so, I would say the people that we hired were always through an agency like, like a Virtual Latinos. And for us, it was a great experience. I think they— everybody's interests are kind of aligned, right? Is that the agency wants to do a good job, right? They want to put a great person who fits what you need into your company, which of course what we want as company operators. And so everybody's interests are aligned there. And, um, yeah, I just, I thought it was a, a great system that worked really well.

Yeah. Did you, um, were these like virtual assistant type roles? Do you remember?

Or like, not, not always. No. Like we, we did a lot of different things. So we did everything from, uh, like a video production person in Mexico to project managers to customer success people. Because, you know, this was mostly with the tech company, right? So we had a a lot of kind of different roles that we needed to fill in there. Trying to think the other ones that we had, but yeah, it was a pretty wide gamut of a bunch of different kinds of roles. And then we would, what we would try our best to do, which is what we would do with everyone who worked in our company, is try to evolve them over time into roles that they felt really energized by. So that again, that was our philosophy. Um, but yeah, that, and that really worked well, I think, for a lot of the folks that, that worked with us because over time you get to do more things that energize you and hopefully less of the things that don't. And then maybe we can go and hire somebody else who actually enjoys doing the things that nobody else wants to do. And that, so that was always a part of our philosophy is just because nobody here is energized by that thing doesn't mean that there's nobody anywhere. That is energized, right? We just need to go find that person who's energized by that thing and recruit them.

Yeah. And the mechanics of it, now, did you put these people outside of the US on your payroll or was it on the agency's payroll and you would get like an invoice? And I'm asking, you know, for other listeners that are just like, how does this even work?

Yeah. Yeah. We would always pay the agency and then the agency would pay the people. And, you know, for us that was really simple. You know, so yeah, from a company operator perspective, that's a pretty, that's a pretty easy transaction. And so I, you know, I imagine that's at least one of the reasons why they're doing it that way. And then also it kind of like shields us a little bit too from having to understand all of the complexities of doing business in all of these different countries, right? That's the other obvious benefit probably is I don't want to have to like learn about, How to set up registered entities in Ecuador if I don't have to, right? Like that. So yeah, I always appreciate the agencies for that too.

Yeah, sure. Would you say there was any work that you would be uncomfortable moving offshore or nearshore, or was everything on the table in your company?

Oh, let's see. I'd say almost everything was on the table, right? We kept a lot of the kind of the strategic leadership team roles here, not because we didn't believe we couldn't find them elsewhere, but just because this is where the founders were, you know? And we had a pretty clear vision for what we were trying to create and what we were trying to do. And yes, we never got to that point where we were, recruiting another person for the leadership team or the strategic team, right? Like at that level, we never recruited for. And so that would have been an interesting exercise to see how we would have done that. But yeah, it was— I was pleased with everybody we hired. I mean, yeah, it was a really good experience overall. Yeah.

So today in your role as CEO of Work Revolution, you're doing a lot of writing, a lot of speaking. And from my understanding, you're working with executive assistants, virtual assistants to give you leverage. Can you tell us more about that and what countries you're working with?

Yeah, right now I do have one. I call her my chief of staff. And so still part-time, right? We're building, right? This is building phase of new business. So yeah, entrepreneurs out there, you know this phase, right? You're wearing a lot of hats and working a lot of hours. But yeah, I'm really happy to to have a little bit of help, uh, from, uh, yeah, a new colleague in Ecuador. And so, yeah, she's been great and it's, it's still very new. And so we're still kind of learning how to, how to work together. And, you know, she's learning about all my idiosyncrasies and all of, all of that. Um, but yeah, it's been just a huge help already in, in helping me on social media and doing reachouts and building the database. Uh, Yeah. So it's kind of a combination of some, I wouldn't say too much admin stuff. Like there's, there's right now she's doing a lot of social stuff and a lot of kind of sales reach out kind of stuff to help us build the pipeline of people that, that we will hopefully get to partner and work with down the road.

And Josh, when you just think through like the logistics of working with somebody, probably very similar to, you know, if they were in Florida. But are using like Asana and Slack and, you know, to communicate work and outcomes and feedback and Google Meet? Like, what kind of tools are you using?

Yeah, yeah. So yeah, I've been a Zoom guy forever and I've been a Slack guy forever also. So those are still my two, two main platforms. And then other than that, we use a lot of Google Docs. To kind of go back and forth and create databases and spreadsheets, you know, for people we're reaching out to. And yeah, so those are probably my key collaborative tools. Yeah, G Suite, Slack, Zoom. I think that's the majority.

And any issues with English fluency communicating with your chief of staff in Ecuador?

No, not this, no. She's, yeah, incredible. Might be more fluent than me, I don't know. It's pretty incredible. In the past though, we had some of that challenge with some people. Never anything that was like a deal breaker, but yeah, sometimes it was a little bit challenging, but I think you can, if you just make that part of your hiring process, right? So, because not every role needs to be like super crazy fluent, right? Like some roles, right? They're working more in the background or they're working on data or they're working on projects and they're not super customer-facing. -facing and it's, you know, and they kill it and it's fine, you know, if, if they're not 100%, you know, English fluent. So I think it just depends on the job.

Yeah. Shifting gears a little bit to what you're doing now, you know, you're a prolific writer, prolific speaker. There's a lot of content to bring together. Tell us about how you're using AI for that.

Yeah. So what, what I'm experimenting with currently is, so right now I'm a ChatGPT user and a subscriber, right? So I pay for their pro plan or whatever it's called, or the plus plan. I don't know. The one that's not super, there's a super expensive one now too. I don't do that one, but like the middle one. And what I'm experiencing with now is trying to kind of like feed it all of my writing because I've got, I've been blogging I've been blogging for 20— I think it's been 20 years. I think I posted my first blog in January of 2005. So I think it's actually been 20 years since I started blogging, which is insane to me. And I— so I want to like feed GPT all of my writing. So I just thought the other day, I was like, this would be like— it should know what I think and how I write. And like, I've got this huge resource of all of this stuff that I've written over the years. And how cool would it be for it to be able to like ask this thing questions about myself? And so this is my current project, like side project. And so far I've not gone back that far, right? I just went to like, I don't know, middle of last year or something and fed it all of my articles. But it's amazing, like just how I can dialogue with it now at a really high level because it understands some of my verbiage and my perspective and framing. And it's really impressive. And so I'm, that's what I'm playing with now. And I think it's going to cut my book writing time in much, much smaller than it'd be much shorter than I think the last book that I wrote.

Yeah. As we start to wind down the show, Josh, you know, as you've been exposed to a lot of different countries around the world. Where's the next place that you love to travel to that you haven't been to yet?

Oh goodness. For forever, my answer to this was Thailand, and I actually got to go there last year. And so that was fabulous. Let's see.

Yeah.

What's next? Maybe I feel like there's some places in Europe that I would like to visit that I haven't been. So some of some of the Nordic countries I would like to visit. That's, uh, I've got some, some heritage there. So that, that might be up, up on my list. Then also, I don't know, I hear Croatia is beautiful. I'd love to. So there's some places in Europe I think I need to get to next, probably.

Yeah. Great stuff. Where can listeners find you? Where would you like them to, uh, to look you up?

Yeah, please, please do come connect with me. I'm super easy to find as long as you can remember how to spell my name. Look me up on LinkedIn. So Josh Allen Dykstra, and then also joshallen.com. So that's the other, other place. Just remember Allen has two A's and two L's. A-L-L-A-N. joshallen.com. And yeah, those are probably the best places.

Good stuff. Well, you're listening to the Nearshore Cafe podcast sponsored by Plug Technologies, plugg.tech. Great way to connect. Talent from all over Latin America, just like Josh shared with his, uh, chief of staff, virtual assistants, video production, all sorts of great stuff. Thanks so much for listening, everybody. We'll see you next time.