Leveraging Virtual Assistants and Hiring Strategies with Josh Allan Dystra | The Nearshore Cafe

**Brian:** Welcome to another episode of the Nearshore Cafe podcast. I’m Brian Samson, your host. Today is 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 guest, let me thank our sponsor, Plug Technologies, plug.gg.te, a great way to connect talent all over Latin America with U.S. companies. Without further ado, let me introduce Josh Allan Dystra, CEO of Work Revolution. Josh, great to have you on the show!

**Josh:** Thanks for having me, Brian.

**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 bit about your mission and what’s been driving you all these years.

**Josh:** Yeah, sure, sure. So, initially, I thought I was going to do music. I grew up as a classically trained pianist on stages and in churches, recitals, and stuff like that. So I always knew I liked to be on stages. As I got into high school, I picked up more instruments. Then, I got into college, started writing songs, forming bands, right? I kind of left college with this idea that I should probably be a rock star. So I decided that would be a good plan. I moved to Los Angeles, got a management deal, shopped the record labels, recorded the albums, and did the gigs. Then I 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 like quarter-life crisis, a 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?” 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, there was a good culture that affected the rest of my life in a positive way. On the opposite side, if it was a crappy manager, that was really interesting to me. So I did a little bit of research and 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, right?” 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?” So I’ve devoted—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. I’m kind of like a serial entrepreneur in that space, so everything I do has been towards that mission. I’ve done a bunch of different companies: consulting firms, training coaches and consultants, tech companies, and all sorts of things, but always after this idea of how do we make work life-giving instead of life-sucking.

**Brian:** Love it. Let’s actually dive a little deeper, kind of step by step, because I think that shapes the narrative later for how you might have thought about leverage. But if you could start, like, the first couple companies, what were they? What were you doing all that?

**Josh:** 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, right? So I thought, “Oh, that’s interesting.” And then you could write books instead of writing songs. So it’s 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. I got out of this with a shiny degree. I graduated in 2009, 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. I started consulting around leadership and culture and employee engagement and positive psychology and strengths, how to do more of what you should—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. I started doing a lot of consulting, a lot of workshops. I did a lot of “little stages,” small groups of people that I got to speak with and to. That’s what I did for almost a decade: mostly consulting and workshops.

In 2012, I published my first book—my first business book—and so then I started actually getting on more stages. But it was slow, right? It was slow going, and it was always kind of on the side of my consulting and workshops business. 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. 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 because we had just moved to Denver. I wanted to be home more. So I just stopped; I stopped speaking. I built a business where we trained coaches and consultants. We trained three or four hundred coaches, consultants, and HR people inside companies and out.

About six-ish years ago, I got this crazy idea to build a tech company. I thought, “This is a big problem, right?” People do not like their work all over the world. There are hundreds of millions of us that experience this kind of disconnect from loving our work. We just don’t. So I thought to meet the scale of this problem at the scale of the whole, you need something exponential like tech. I was like, “I’m going to build some technology.” So this is like 2018 or something like that, 2019. Man, Brian, I thought we had it right! I thought, because 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 thought we were building a unicorn. I thought we were building the billion-dollar company. But it was not to be. We were—when the tailwinds kind of switched to headwinds in 2023 or so, and people started demanding return to office—we were just underfunded. We didn’t raise enough back in the day. So I learned a lot of valuable lessons. 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 to, because I didn’t do enough of it back in the day. So that’s primarily what I do now is speaking and thought leadership.

**Brian:** Yeah, yeah. Back to your tech company. I remember those years of quiet quitting and everyone—yeah, the Great Resignation. More, probably twice as many jobs available as there were people. Yep, yep, it was just a…

**Josh:** Yeah, it was such a market for employees, right? It was such a rich time for people, for labor, for workers. And then, to see it kind of flip pretty hard in the last couple years has been—that’s been an interesting bit of whiplash.

**Brian:** How would you describe the market today for labor?

**Josh:** I think we’re still seeing a lot of this whiplash effect. The pendulum has swung back, I think, in the other way in a lot of ways. There’s still, at least here in the U.S., a decent amount of “get back to the office” kind of stuff. We’ve got all this office real estate, and 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. The data really doesn’t bear that out as true, but it’s a good talking line for the reporters, I guess. I think this kind of hybrid remote thing is here to stay, at least in people’s psyches. 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? 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 plays out.

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

**Josh:** We were totally spread out. My other companies, my service-based companies, were actually fully remote. So we were those kind of distributed, remote companies before it was cool, or before it was necessary. We had really learned how to work on Zoom and in Slack and build a really cohesive culture remotely and virtually, because my business partners at the time were in Kansas City, and I’m in Denver. Neither of us were going to move to the other place, and so it was like, “Wow, I guess we’ve got to figure this out!” When we started hiring people, we always just hired them from anywhere. It just kind of made sense, right? We weren’t limited by geography at all. At our peak, we had just about 20 people, and we had people all over the world. We had people in Austin, and we had people in Israel, and we had people in Brazil and Mexico. We had people in Venezuela. Just like all—I think we were across, I don’t know, four or five time zones. It was a really cool adventure.

**Brian:** What did you learn, or what kind of advice could you share with leaders that are building remote companies, and they’ve got people in different time zones, different countries? There’s the leadership part of that, and there’s also the management part of that.

**Josh:** Yeah, I think 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, office leaders, office-based leaders have struggled with—is that they’re conflating culture and office. 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 their desk. You might run into each other in the hallway or in the bathroom or at the water cooler or cafeteria, right? These collisions kind of happen organically when you’re in the same physical space. Of course, that doesn’t happen if you’re spread across five 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 outgrowth of you as the senior leader or as the founder, right? You’re going to kind of 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. So you can absolutely build a world-class, phenomenal culture entirely remotely; you just have to do it in a very intentional way.

**Brian:** How would that come into play when it’s U.S. only versus, like, 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?

**Josh:** I think one of the things that we did really well was to celebrate not just company culture, but culture, like, “C” culture—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 is one of my business partners’ ideas: to really try to deliberately celebrate and learn about, “Hey, what are your holidays in Venezuela? What are you 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 maybe would not know or understand. And that was really rich; that was a really rich time for us.

There are so many things where, across the world, we want the same things, right? I think that’s the other thing that I learned very clearly from doing this: there are many things that are 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 be able to work in our strengths, right? That stuff is true no matter where you are in the world. And then there’s also these really unique things that I think are really important to celebrate: the uniqueness of the different cultures. So I’d say it’s kind of like both of those things: appreciate all of the similarities that we have, and then celebrate the places that are different. If you can do both of those things, you’ll have an awesome, awesome culture no matter where your people are.

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

**Josh:** Huh, 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—or core values, right—as a company, we called them vital behaviors. But some of our core, these really core belief system kinds of things that we organized around—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. 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. I don’t really care if you have a degree. I don’t really care where you live. Can you do the job, and 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.

**Brian:** Can you think back to the first time you hired outside of the U.S. and just the mechanics of it? How did you, like, did you go to Upwork or agencies? How did you guys even start? I’m sure there are business owners, startup founders, that are listening, and they’re like, “This sounds interesting! What’s the first step? What’s step two? What’s step three?”

**Josh:** 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. That was our go-to for a while, and 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 were a couple projects here and there that we’ve done over the years through like an Upwork, where we contract directly with the person. But more so, I would say the people that we hired were always through an agency, like a Virtual Latinos. And for us, it was a great experience. I think everybody’s interests are kind of aligned, right? Because the agency wants to do a good job; they want to put a great person who fits what you need into your company, which is, of course, what we want as company operators. So everybody’s interests are aligned there, and I just thought it was a great system that worked really well.

**Brian:** Were these like virtual assistant type roles, do you remember? Or like…?

**Josh:** Not always, no. We did a lot of different things. So we did everything from a video production person in Mexico to project managers to customer success people, because this was mostly with the tech company, right? So we had a lot of different roles that we needed to fill in there. Trying to think of the other ones that we had. But yeah, it was a pretty wide gamut of a bunch of different kinds of roles. And 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. Again, that was our philosophy. That really worked well, I think, for a lot of the folks 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. So that was always a part of our philosophy: just because nobody here is energized by that thing doesn’t mean that there’s nobody anywhere that is, right? We just need to go find that person who’s energized by that thing and recruit them.

**Brian:** And the mechanics of it now: Did you put these people outside of the U.S. on your payroll, or was it on the agency’s payroll, and you would get like an invoice? I’m asking for other listeners that are just like, “How does this even work?”

**Josh:** Yeah, yeah. We would always pay the agency, and then the agency would pay the people. For us, that was really simple. So from a company operator perspective, that’s a pretty easy transaction. I imagine that’s at least one of the reasons why they’re doing it that way. Then also, it kind of 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: I don’t want to have to learn about how to set up registered entities in Ecuador if I don’t have to, right? So I always appreciate the agencies for that too.

**Brian:** 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?

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

**Brian:** 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?

**Josh:** Yeah, right now I do have one. I call her my Chief of Staff. She’s still part-time, right? We’re building—this is the building phase of a new business. So, 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 have a little bit of help from a new colleague in Ecuador. She’s been great, and it’s still very new. We’re still kind of learning how to work together. She’s learning about all my idiosyncrasies and all of that. But yeah, it’s been just a huge help already in helping me on social media and doing outreach and building the database. So it’s kind of a combination of some—I wouldn’t say too much admin stuff. Right now, she’s doing a lot of social stuff and a lot of kind of sales outreach to help us build the pipeline of people that we will hopefully get to partner and work with down the road.

**Brian:** And Josh, when you just think through the logistics of working with somebody, probably very similar to if they were in Florida: Are you using like Asana and Slack to communicate work and outcomes and feedback, and Google Meet? What kind of tools are you using?

**Josh:** 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 main platforms. Other than that, we use a lot of Google Docs to kind of go back and forth and create databases and spreadsheets for people we’re reaching out to. So those are probably my key collaborative tools. Yeah, G Suite, Slack, Zoom. I think that’s the majority.

**Brian:** Any issues with English fluency communicating with your Chief of Staff in Ecuador?

**Josh:** No, not this one, no. She’s incredible; might be more fluent than me, I don’t know. It’s pretty incredible. In the past, we had some of that challenge with some people—never anything that was like a deal-breaker. But sometimes it was a little bit challenging. I think you can just make that part of your hiring process, right? Not every role needs to be like super crazy fluent, right? Some roles, 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. And they kill it, and it’s fine if they’re not 100% English fluent. So I think it just depends on the job.

**Brian:** Shifting gears a little bit to what you’re doing now. 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.

**Josh:** Yeah, so what I’m experimenting with currently is—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—there’s a super expensive one now too; I don’t do that one, but like the middle one. And what I’m experimenting with now is trying to kind of feed it all of my writing. I’ve been blogging—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. So I want to feed GPT all of my writing. I just thought the other day, I was like, this would be like it should know what I think and how I write. And I’ve got this huge resource of all of this stuff that I’ve written over the years, and how cool would it be to be able to ask this thing questions about myself? So this is my current project, like, side project. So far, I’ve not gone back that far. I just went to like, I don’t know, the middle of last year or something and fed it all of my articles. But it’s amazing, 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, really impressive. That’s what I’m playing with now. I think it’s going to cut my book-writing time and be much shorter than I think the last book that I wrote.

**Brian:** As we start to wind down the show, Josh, as you’ve been exposed to a lot of different countries around the world, where’s the next place that you’d love to travel to that you haven’t been to yet?

**Josh:** Oh goodness. Forever, my answer to this was Thailand, and I actually got to go there last year, and that was fabulous. Let’s see, what’s next? Maybe I feel like there are some places in Europe that I would like to visit that I haven’t been. Some of the Nordic countries I would like to visit; I’ve got some heritage there, so that might be up on my list. Also, I hear Croatia is beautiful. I’d love to. So there are some places in Europe I think I need to get to next, probably.

**Brian:** Yeah, great stuff. Where can listeners find you? Where would you like them to look you up?

**Josh:** 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: Josh Allan Dystra. And also, joshallan.com. That’s the other place. Just remember Allan has two A’s and two L’s. Joshallan.com. Yeah, those are probably the best places.

**Brian:** Well, you’re listening to the Nearshore Cafe podcast, sponsored by Plug Technologies, plug.gg.te, a great way to connect talent from all over Latin America, just like Josh shared with his Chief of Staff, virtual assistants, video production—all sorts of great stuff. Thanks so much for listening, everybody! We’ll see you next time.