Matt Bowles: Hey, everybody, it’s Matt Bowles! Welcome to The Maverick Show! My guest today is Sean Tierney, he is the Director of Sales at Pagely, a managed WordPress hosting provider that serves clients such as Disney, Warner Bros., Comcast, and many others that you would surely know, and he does it all while working remotely from some of the most epic locations around the world! In Sean’s first year of being a digital nomad, he increased Pagely’s annual revenue by 70 percent year-over-year, and he did it all while traveling the world on the Remote Year program, and living in 18 different countries on four continents that year.

In the last three years total, Sean’s sales expertise has helped Pagely to grow from eight to 38 employees. And he has subsequently gotten international media attention, and speaking engagements around the world for the sales systems and processes he has built, including his concept of “flinstoning”, his automation philosophy on scaling personal attention, and the Choose Your Own Adventure video consultation experience that he designed and implemented at Pagely.

Sean is also the host of the Nomad Podcast, and founder of the Nomad Prep Academy—an online training course to help more people transition into the nomadic lifestyle—Sean, welcome to the show!

Sean Tierney: My, man, it’s good to be here!

Matt: Awesome to have you here, brother, this show has been a long time in the making, man, this episode.

Sean: It has, indeed.

Matt: Let’s just set the scene here for people a little bit: you and I are in Jericoacoara, Brazil; we are on the beach, and it’s about 6:30 in the evening right now, our time. We have just opened a bottle of Chilean Carménère—which we will be drinking through on this episode—and you and I have just spent about two full weeks together in Brazil.

Sean: Indeed.

Matt: And your first time here?

Sean: It is, yeah.
Matt: So, I feel like we just need to explain a little bit for people that have never been to Brazil, or have never been to this part of Brazil, just a little bit about what we have experienced thus far. So, do you want to share some of the highlights from the last two weeks?

Sean: Well, I think it bears mentioning we’ve got a cat sitting in the corner now that just wandered into the room; my water bottle is sweating about much as I am. So, no, it’s been great, man. So, you came off the Nomadic cruise, and I basically flew into Recife and met you in Porto de Galinhas, did a couple days there, did a couple days in Pipa, and then we came to Jericoacoara.

Matt: The entire town is literally on the beach! Like, there are no paved roads, there are no – it’s all sand, so every path that you can walk on is all sand! And there are restaurants, and there are shops, but it’s all sand, there are no paved roads, and if you really needed to drive somewhere, you get in a dune buggy, and you drive in that.

Sean: Yeah, exactly.

Matt: I mean it’s totally insane! But the other thing is that this also one of the preeminent kitesurfing destinations in the world. And I know that you are a kite-surfer, and you got out there on the water this week, so do you want to share a little bit just for people maybe that don’t even know what kitesurfing is? What is kitesurfing? And maybe talk a little bit about: what you connected with about the sport; what it feels like when you’re doing it, and what it means to you.

Sean: Yeah, absolutely. So, kitesurfing is – probably people are more familiar with windsurfing, but it’s the same concept: it’s a wind sport, you’re on a board, and you’re being propelled by the wind; except instead of holding that sail up in front of you, you’re actually holding lines that lead to a kite, probably 30 meters out. So, picture just flying a big kite behind a wakeboard, essentially. I first learned the sport in the Dominican Republic a few years ago, and it was of those things where I first tried it, and I knew I was going to be doing this forever; it’s an incredible sport.

But yeah, no it was really strong – I went out two days ago, and I have a larger kite with me right now, and man, it was gusty here. So, it was like right at the edge of what I could handle, but it was a lot of fun.

Matt: And how was the experience learning to kitesurf? You told me when you initially were learning in the Dominican Republic you were renting kites before you owned your own.

Sean: Yeah.

Matt: And then, how was that experience when you were initially learning, and what was that experience with the other kites-urfer – rooky guy came down the street?

Sean: Right, right, so –

Matt: He was on the beach.

Sean: – the story that I related to you in learning – so, fortunately when you’re learning, there’s insurance on it. So, if anything happens to the kite, you’re under supervision, very unlikely you can get hurt, and if something happens, they’re going to foot the bill for it. So, anyway, I’m kiting, I’m doing okay, and a beginner comes up, and just absolutely tomahawks my kite, I don’t think he saw me or something, but just brings his kite down, dives the kite right on top of mine, and splits it right in half. And the instructor – yeah, it just peeled – it did something it should not ever do, and it’s a $1,000.00 kite, and the guy said, “Oh, okay, that’s on us,” so.

Matt: I think that’s why I would always rent a kite, and have somebody there with insurance because, for me, I’m sure that type of thing would be very likely to befall me. But that’s amazing, I mean, the sport looks incredible, and I’m hoping – I’m going to be here for another week, so I’m hoping to be able to get out, and least try it and get sort of a rookie lesson because it does look amazing. And all the people that I know that kitesurf just rave about it in terms of what it feels like and –

Sean: It’s a life-changing sport. It’s one of these things where it’s a learning curve to get into it, but once it clicks, just that feeling of being out on the water propelled by the wind, nothing else, it’s just quiet, and you’re just – and the jumps – it’s an amazing sport.

Matt: That’s awesome, well I definitely have to get out there and try that this week while we’re still here. So, you and I have been planning to do this interview I feel like for a really long time, we’ve been waiting until we are in-person, again—and just for background: you and I probably met I feel like it was a good six months ago now in Lisbon –

Sean: That’s right.

Matt: – where you’re based now for at least half the year or so, and then you’re traveling around for the other half to epic places like this. And then, we had met because we both finished the Remote Year program, we were in different cohorts, but we both completed Remote Year, so as part of that alumni network we met in Lisbon. And then, we later reconnected this past summer in Barcelona, and we hung out with—actually, listeners will know Jen Magee from episode five—so it was me, and Jen Magee, and then our friend Erica’s birthday.

And so, we connected with you, you took us out, you bought us all round of Fernet and Coke, and I feel like the last time I saw you—until Brazil—was on the street corner at 3:00 in the morning in Barcelona, that was my final Sean Tierney memory. But at that moment we were like, “Man, I have to get you,” I was like, “I have to get you on the podcast.” And you were like, “I get you on my podcast,” so we’re like, “Let’s record them both when we’re down in Brazil!” So, this has been many months in the making, so I’m super-excited to get this conversation under way, man.

So, the other thing – I mean, let’s start a little bit back: you grew up and as you were coming up, music has always been a strong passion for you, and you’ve been musically inclined, and musically involved, and that kind of stuff. Can you talk a little bit about that part of your personal history, and what music has meant to you?

Sean: Yeah, so, I don’t know, this is an interesting thing, I was taught violin early-on as a kid, that never really stuck; I took piano lessons, that didn’t really stick. And I think this is like the larger lesson that I took from this after finally finding the guitar—which is my instrument—is that I think a lot of times people give up before they find their instrument in music, but then also take what you will from that to other things. But I really think that if you have a failure, and a failure, it could just be that third time that is your instrument, so don’t give up on that.

But I discovered the guitar, and it just clicked—just like kitesurfing—I knew I was going to be doing this forever. I had a great teacher; I’ve given actually one of the Ignite Talks on the subject of the different plateaus in music, and how you break through those. But for me, it was a teacher, and then learning how to read tablature, and getting a four-track. You’re into music, and DJing, so you know about – four-track is the old school way of recording, that was the next level. So, yeah, music has been a huge part of my life.

Matt: That’s awesome! I mean, literally just last night we were hanging out with a bunch of digital nomads here in Brazil, there must’ve been, I don’t know, 25 people or 30 people at this barbecue, hanging out at somebody’s villa. And it got dark, and everybody was just sitting around outside on these outdoor couches, and somebody pulls out a guitar, you know? And it was just basically an ad hoc jam session, and you jumped on it, and everybody was sitting around you, and there was a couple of other people that were playing as well.

But it’s an amazing skill to have I think, and something that certainly you carry with you for the rest of your life. And certainly one skill that I appreciate because I am in no way musically inclined at all, other than my DJing era. But I thought it was amazing because you really – when you go different places, you really immerse yourself in those cultures through music. And so, when we were coming here to Brazil, you had said to me, “I just memorized this Brazilian song, and I can sing it in Portuguese, and I can play it on the guitar,” and it’s a Brazilian song by a Brazilian pop artist.

And you were like, “I have to figure out a venue, I have to figure out how I can get on stage somewhere, or in front of crowd somewhere, and also come up with a guitar”—because you’re not traveling with a guitar—“so I need a guitar, and I need a microphone in front of an audience, and if I can get that, I can drop this Brazilian song for the Brazilian audience.” And so, when you told me that I immediately started thinking, I was like, “All right,” so this is on the back of my mind for the whole time we were there. So, were in – we’ve been now to three towns: so we’ve been to Porto de Galinhas, we’ve been to Pipa, and now we’re in Jericoacoara.

And so, when we were in Pipa, and we were walking that night with a couple of friends of ours, I see this – exactly the venue that I had pictured, that you said you wanted. So, it was a bar, it was open to the street—a restaurant-type bar—and there was a – obviously, the singer that was in there was playing the guitar, acoustic guitar in front of a microphone. And I looked in, and I remembered what you wanted, and I was like, “I’m going to go in and see if I can negotiate my man to get up and do one song because I know these people when they’re going to see you –” right?

Because you’re like 6’7”, American dude, and you were going to roll in there, and they’re going to be like, “What is this dude going to play?” and then when you dropped that song I knew they were going to go crazy. So, I go in, and I was like, “Wait here,” I told you and our friends, “Wait here, let me go see if I can get him on.” And I go in—and of course, my Portuguese is very – very minimal—but between my broken Portuguese and their broken English, we kind of – I explained what we wanted, and they were amenable to it.

And so, we got you up there, with the guitar, you got to use that person’s guitar, and in front of the mic, and – are you able to—we don’t have a guitar here is the only thing—but you are able to do like maybe just a verse or part of the verse a cappella in terms of what it was that you sang that night? Because as you soon as sang it, the first three or four words, I was looking around like everybody just looked up, and they all knew the song! And so, they’re all singing along like, “Oh!” and it was crazy! Are you able to do a verse just to give people a sense of – that song?

Sean: Just a cappella off the go? Sure, with a disclaimer that my guitar is my strong suit, the singing is just like the – singing is not my strong suit, but yeah, sure. So, the song is “Donna Maria,” and it’s [singing in Portuguese].

Matt: I love it, man!

Sean: Enough, that’s all you get!

Matt: It was so good! It was so good, and everybody just looked up, and the whole place was singing along! And they were like – couldn’t believe that you knew it, and you played to the crowd, my man, which was amazing. And now we’re here in Jeri, and we are seeing all kinds of remarkable things here. I mean, I expected this super-secluded, tiny, beach town, remote town and stuff, and I didn’t know if it’d be – like everybody would be asleep by – 8:00 or what it would be, but this town is just totally nuts! They have this section called Caipirinha Street, which is literally like 50 caipirinha carts. And so, for people that don’t know what caipirinhas are, it’s the Brazilian national drink. So, the alcohol that’s in it is called cachaça—which is a Brazilian spirit—and then there are only two ingredients which are: lime and sugar. And if you blend those three ingredients properly, and you make this drink properly, it is absolutely outstanding!

And so, here in Jericoacoara, there’s something called Caipirinha Street—which again, remember, the streets here are just sand, so it’s literally just like a section of the beach path, right?—and there’s probably literally 40 to 50 caipirinha carts of people that make the caipirinha drink. They all look identically the same, and then when you go down there at night, every single one of them is doing business.

Sean: Yeah, when we got there, I’m like, “How is this possibly going to support the demand? There’s nobody here, it was a ghost town, and there are 50 caipirinha trucks, what are we doing?” And then sure enough, yeah, there’s like a line five people deep an hour later, it was crazy!

Matt: It was amazing! And they have this super-interesting club—I’m going to call it a “nightclub”—although it’s called Café Jeri, and it’s a roof-top nightclub. But the fascinating thing is that it’s only open during happy hour; it’s literally only open from like 6:00 to 8:30 or something but it’s as live and crazy as any nightclub that you’ll ever imagine! They have on the roof: fire twirlers, and people – I mean, I’m talking like eight to 12 people that are like juggling fire, and they have the flair bartenders that are juggling the bottles, and standing up on the bar. They literally have a tank, a water tank, with a mermaid in it, right?

So, they have – this woman is wearing this whole mermaid suit with the mermaid tail swimming around. And then they start doing AcroYoga on the roof, and they’ve got the mermaid up doing AcroYoga. I mean, it was like one of the wildest nightclub scenes I’ve ever seen, and it’s here in this tiny beach town. And oh, by the way, this is only happy hour because it closes at 8:30, and then everyone goes to Caipirinha Street. I mean, it’s just been completely over-the-top!

Sean: It’s ridiculous, yeah. And I’ve never seen a town like you said built completely on sand. I don’t know if there’s bedrock somewhere there, or all these houses are just built on sand, I guess, I don’t know.

Matt: I have no idea, but it’s basically a giant beach with buildings on it, it’s totally nuts and totally amazing! Brazil is a place that is always, to me, a very magical place. Each time I come here, I’m just like, “Oh, yeah, that’s what I love about Brazil!” I mean, it’s just really, really, a very, very special place! So, it’s awesome to be back here, and I feel like some of our discussions about the caipirinha trucks, and the market there, and this particular club, and how packed they are every night, all of these actually tie in well with our sales discussion, which I want to have on this podcast with you, and I want to go pretty deep and granular on the sales stuff.

And for all the people that are listening that are either in sales, or they’re in business of some kind, or they’re building businesses, I think are going to get a lot out of this discussion. But I think this actually leads into it quite well because you were talking about, “Oh, there’s 40 caipirinha trucks, is there really a market for 40 caipirinha trucks in Jericoacoara?” Oh, yes, there is and they know exactly what their market is, and they’re all catering to it, right? Or this amazing club that has all of this crazy acrobatic stuff going on, but it’s only open during happy hour!

And it was interesting because today I heard a number of our digital nomad friends talking, and they’re like, “I love this concept!” I go to the club—and I mean, it is a dance club, I mean people are soaked with sweat, they’re dancing, like hard dancing like you would at a club. But then it closes at 8:30, so they’re like, “I go, I party as hard as I can. I mean, the bar, and the dancing, and all this stuff, from 6:00 to 8:30! And then, I leave the club, I go to dinner, and then if I want to, I can be in bed before 10:00!” they’re like, “I love this concept!” right? So, they’ve clearly hit a product/market, or a service/market fit there, and they’re crushing it!

Sean: Oh, yeah. No, and it’s wall-to-wall; if you get there I think after 7:00, there’s no way you’re getting in, so.

Matt: Yeah, exactly! So, let’s talk a little bit – let’s go into the sales stuff here, and maybe let’s just start with that from the very beginning, and then I want to go – start from people that are at the early stage of developing their product or their service, and getting their sales initiatives off the ground. And then, I want to just go through the whole acceleration process, and the systematizing, and get quite granular because I think a lot of people that run businesses are going to really get a lot out of this conversation, so. But let’s just start at the very beginning for people that are conceptualizing a product or service, how do they think about product/market fit and the minimum viable product, and what should they be doing at that stage?

Sean: Sure. So, I guess this is a key distinction that people need to realize: so I used to run something called The Lean Startup Circle for Phoenix. Lean Startup—for those people that are listening who aren’t familiar with it—it was book put out by Eric Ries that was actually a follow on to Steve Blank’s original Four Steps to the Epiphany. And it’s this concept of: there is a way to build a startup that de-risks how you do it. It can drastically reduce the headaches, and the capital loss, and all the heartache of building a startup.

So, there’s like this magic demarcation point where if you’re pre-product/market fit, it’s foolish to worry about growth. Don’t even think about: how do we scale this thing because it’s not working yet? So, pre-product/market fit, everything that you do should be around finding product/market fit. And I’m not going to remember this off-hand, but Sean Ellis I think has the best definition, it has to do with: a certain percentage of people say they can’t live without your service once they try it. So, it’s like 60 percent of your target market once they use it, they just say they can’t live without it, and that’s kind of the litmus test of: have we achieved product fit yet or not?

Once you do achieve product/market fit, your emphasis totally shifts away from that. It’s not like you forget about it, and you don’t keep improving your product, but your emphasis now shifts towards: how do we scale this thing? So, I guess my advice to those people who are pre-product/market fit would be: do the things that will get you to product/market fit.

Matt: And what are those things? How do you test for minimum viable product? And how do you – what are the threshold where – or the benchmark where you can say, “Okay, this is going to work, this is solid, and now I want to start scaling?”

Sean: Yeah, so this is not a science it’s an art, but straight-out my best advice is to Google Steve Blank Udacity; that’s Steve Blank Udacity, and that course is now—in my opinion—the de facto thing that everyone should just watch. They now teach this – like at Stanford I don’t believe they teach writing a business plan anymore; Steve Blank’s Business Model Canvas and this whole process is definitively how you do a startup at this point. So, if you’re in that phase, I highly recommend you just Google Steve Blank Udacity, there’s a free course out there, it’s like a six-hour/one-month long course, you do a bunch of exercises and whatnot, but I highly recommend doing that as the next step.

Matt: Okay, cool. And then, once you get to that point, and you say, “Okay, I have established it, we’ve sold enough to demonstrate that there is clearly demand for this, we want to scale it,” what are the steps to scaling a sales department?

Sean: Yeah, okay. So, I will take you through – I basically came up with a seven-step system, this is just cobbled together from books I read, and my personal experience, and whatnot. But this got some traction, I did a talk in Lisbon, if you Google Pagely Sales System, it’s the first thing that comes up, and this is all the Prezi presentation video and what not. But we use walk-through, there are basically seven steps; so the first step is to what I say, map-out your flows. So, you need to understand – I parachuted into Pagely, I didn’t know where the skeletons are buried, and how things work, and what the sales system was; there really wasn’t a sales system.

So, you have to really map-out what exists, and I have two types of maps that I do—I don’t how deep we want to go into this—but basically, I draw out a map that shows me: what are the flows of information; how do people get to the site; where are they going in the site, and then where does that information land? So, what are the repositories of this data, and how did it get there? And then, the other one that I do is called – I basically took it from the Infusionsoft lifecycle marketing funnel, but you basically do a left-to-right diagram of the lifecycle, the customer journey: where do these people start in the ether, and then what are the tributaries that feed them into your site?

How do you capture that email address, turn them into a lead, nurture that lead, convert the sale, up-sale them, cross-sale them, get referrals out of them, and just basically move them down that continuum left-to-right? So, those are the two maps that I recommend doing.

Matt: Okay, so first, what you need to do is you need to basically, literally map that out, and actually create a physical, visible flowchart?

Sean: Correct.

Matt: And then, you can see what that path looks like, and what the sales funnel looks like, and you can actually visualize it, which is important because I feel like most people don’t do that. Even if they could rattle off – be like, “Oh, yes, this is what happens, your lead does this, and they come in, and then they have this,” and they kind of verbalize it. If you don’t have it written down, that’s the important step that you’re saying must happen first?

Sean: There’s something about putting it on paper—and I think people who do this will testify to it—but something changes, when you put it on paper it somehow commits you at a greater level to it, and it forces you to acknowledge it, and I just think it’s absolutely worth the time to do.

Matt: And there’s a plug-in you were telling me for free that you can use to actually map it in a visual way with images and stuff like that?

Sean: Yeah, yeah draw.io is a Google – it plays nicely with the Google Docs and Google Drive. So, draw.io, highly recommend that, it’s a flowcharting software, but it also does a bunch of other stuff, and it’s great for this kind of thing.

Matt: Okay, cool. So, then after you have that mapped-out, and you have it visualized in front of you, what is the next step?

Sean: Yep, so track metrics and KPIs—the distinction there being: metrics are very tangible numbers, things like page views, and time-on-site, and things that Google Analytics can quantify for you; KPIs are key performance indicators, and those are more – basically have strategic business value, so they translate to things that matter to your business. So, an example might be MRR—monthly recurring revenue—is a key one that we track; sales cycle, anything that moves the needle or that’s important for you to keep in a dashboard and monitor week-to-week would be KPIs.

And you have to – I mean, they say you can’t improve what you can’t measure, I don’t necessarily agree with that; you can improve things and not be measuring them, but it is far better to measure those things, get a baseline, know where you stand, and then you can actually see what you’re doing, how the changes you’re making are impacting those numbers.

Matt: Cool. So, for each business, the actual KPIs might be slightly different, especially if they’re like micro-KPIs or certain conversion points. Depending on how the flowchart goes, they might say, “How many people are we converting here?” or “How many people are we converting there?” and then they would have different KPIs than another business. So, it would be important for each business to kind of go through and say, “What are the most meaningful key performance indicators for us?”

Sean: Yeah, that’s absolutely right. Everything is contextual based on what you’re doing and the situation. KPIs can roll-up into other KPIs, so you can have a very high-level one like MRR, and then deconstruct that into, “Okay, well what is our lead flow, and what is our close times?” and all the things that lead up to the actual sale.

Matt: Right, and then you’re really looking at the different points of your sales funnel, and so then you’re able to see: where are your different conversion points at each step along your sales funnel, and then where are they dropping off? And so, what are the weak points in your sales funnel that you could then focus efforts on bolstering this is why our end KPI of whatever it is—monthly revenue—isn’t where it needs to be because of this particular point is the weakest in our sales funnel. So, therefore, if we put effort into leveraging and improving that, most likely all of our results would go up.

Sean: That’s right. And the way that I like to think about it is: picture a garden hose where water’s coming in at one end—that’s your flow of leads—and at the other end are your sales; it’s dripping out, some fraction of that is actually converting to a sale. And so, your job as the entrepreneur is basically to look at that, and figure out: where is the kink in this hose; what is the simplest thing I can do to make more sales drip out the other end?

Matt: Right, exactly. Okay, so once you have your flowchart of what your sales process and your buyer experience path looks like, and you have that mapped-out visually, and then you’ve identified the metrics and the KPIs that are the most important for you to track, what then is the next step?
Sean: Sure. Yeah, so establish a process. So, this can be, again, contextually specific to your situation, for us it was as simple as just getting a pipeline created. Trello is a good example of a Kanban-based, I like that style of pipeline, very visual, let’s you see the stages; you have to pick stages that are relevant to you and your business. In our case, kind of the simple flow of how people come in, become a lead, and become a customer is: basically we have a quote forum—and we now have the interactive video thing which I showed you—but people fill out their information, become a lead, we have a dance back-and-forth with sales and some nurturing that goes on with automation.

And then eventually, they either become a customer, or they don’t. And so, moving through that process, if you make sensible milestones in whatever system you’re using to track that, at least now you have a system, and you’re not just shooting-from-the-hip in email.

Matt: Right. And so, when people are trying to establish that process, what should that look like when the process is completed? Because again, it might vary, obviously it’ll be customized from business-to-business, but what are kind of the core tenets of that, or what should it look like when it’s finished?

Sean: So, again, with the lean stuff, I’m a huge believer in don’t pre-optimize; so do only the minimum thing necessary to get you to the next level. I think that’s actually kind of an axiom in entrepreneurship, and you’re nodding your head, so I know you agree. But basically, I would figure out what is the simplest pipeline that we can put in place that will give us useful data in terms of where people stand? What are those major milestones of being a lead, being in dialogue maybe, and closing?

And so, if those are the main kind of high-level pipeline stages, you can always deconstruct those and get high-resolution down the road, but for now, just start with the most basic thing. And don’t get ground-up in trying to figure out all these stages that don’t really mean anything anyway, because I think that’s where people can go off the rails.

Matt: Okay. And then, once you’ve established that process, what then is the next step?

Sean: Right, so I have a philosophy, you eluded to it in the intro: flinstoning. It’s actually not a term that I came up with, I first heard it many years ago from a Canadian thing—it was called Cambrian House—but it always just stuck with me because it makes so much sense. And the gist of it is this: on that theme of not pre-optimizing, and not spending too much time worrying about stuff that doesn’t matter, and automating things that just aren’t important, always do things – err on the side of doing it the manual way.

And so, the reason it ties back to the Flintstone thing is: if you remember the Fred Flintstone mobile: it looks like a car, there’s no engine though, it’s his feet underneath that’s powering the vehicle. And so, you have what seems to be this well-oiled sales machine, but under the hood, it’s you guys just running as fast as you can, human-powered to start. By going through it manually like that, it really – it does a bunch of things: it forces you to confront the situation and to figure out what actually needs to happen, so you’re not diving in and trying to machine-automate things that then turn out to be the completely wrong thing, and don’t matter.

Matt: Okay, so once you establish the process, execute everything manually so that you understand exactly how to do everything and how everything works, and then once you’re doing that and you’re running that fast, what then is the next step?

Sean: Yeah, so I believe—and again, this is all my process, so who’s to say that there isn’t a better way?—but to me, the next step is to delegate. Your last episode that I listened to was Ali Boone, and that was a good example of the idea that you just can’t possibly scale yourself, you run into physical barriers as to what one person can do. And you’re not even necessarily the best person – you’re not going to be amazing at everything. So, it really is cleaving off the roles—to start you’re going to do a lot of functions—but as soon as humanly possible, you want to try to cleave off the things that aren’t your strong suits.

And the way that you choose, or how you choose which roles to cleave off I think is a function of that: picking what you’re good at and trying to not spend time on things that aren’t your core competency; but also, what are the things that are truly eating up all your time?

Matt: Right. And then you can build – once you build the actual system and the process, and you’ve done it yourself, and you can actually write down or record upon video exactly how to do what you do, now all of a sudden, you have a system that you can hire and train someone else exactly how to do what you’ve already been doing. So, it gets done the way you want it to get done because you built that system and you did it, but now you’re just training someone to replace you in running that portion of the system.

Sean: Yeah, that’s absolutely it. And so, once you – that is the key though, what you just said: as soon as you can describe it in terms of like a playbook or a recipe, then that is the instruction set that you either hand to a new person, or you can take that and actually automate it with software.

Matt: Okay, and then after you are able to build those processes, and start hiring other people to run them, and start delegating them, what then is the next step?

Sean: Yeah, so after that, I would say the next step is to automate. At the point at which you’ve been able to successfully delegate these roles, and have other people do them, that shows that you understand it to the extent that it can be passed along to someone else; that’s usually a good opportunity to take that and then take it one step further, and even automate it with a machine.

So, I specialize in – one of the things that I picked up in my weird, winding career trajectory was Lifecycle Marketing automation. And so, I’ve been able to learn a skillset that’s super useful in terms of email automation, intelligent stuff where you can see what people are doing on your website and with emails, and adapt the messaging, personalize it, and just put everything on autopilot.

Matt: Cool. And then, once you do that, I mean, there – well there’s certain things, right? Would you break it out and say that there are certain things that you want to delegate, meaning that you want another human being running at all times; but then there’s a subsection of things that can actually be machine automated, and you should break-out which is which?

Sean: Yep. Yeah, so this is a judgment call: I think the messier stuff – not everything lends itself really well to being able to have a computer do it. We’re going through a process right now actually for Pagely where we are flinstoning this pretty aggressive outreach thing—I told you, the Dr. Dre/Mr. Miyagi thing—and we are delegating, for now; making it very human-powered by design; but at some point, once we know all the variables, we know everything and how it works, and what is effective, at that point then we can look to machine-automated.

Matt: Got it. And can you give some examples of maybe a couple of things that are machine-automated that you were maybe like at one point flinstoning them, but now they’re machine-automated?

Sean: Sure. So, I built a system called Leviathan—which is our – kind of our nerve center, I showed it you—but it’s basically the thing that powers all follow-up with all stakeholders for Pagely. Regardless of if you’re a lead, a prospect, whoever you are, a writer, an investor—although we don’t have investors—but any stakeholder in the system would basically – the follow-up to that person is powered by this thing.

And what it is, is: it knows how we’ve tagged you; what dimensions we’re tracking; about what your pain points are; what features you need; what host you were previously with; who you’re investigating; all these things that we gather, it knows that information and it can basically follow-up at the right time with very highly targeted stuff that’s going to make – that’s going to grab your interest.

Matt: And that’s now all been machine-automated?

Sean: Correct.

Matt: Okay.

Sean: Yeah, but it didn’t start that way, we had to figure out: okay, what’s the right formula here? We kind of came to the conclusion that case studies are very strong for us, we have a lot of big clients—you listed some of them—and so by doing those case studies, and then I essentially coded each one of those case studies on these dimensions, figured out the whole tagging system that we use in calls, and then – yeah, and then once I knew what worked from sending these case studies out manually, then just automated the whole thing.

Matt: So basically, just to give a case study example here—if I’m understanding it correctly—would be: you have a client like Disney, or like Warner Bros., and they have very specific needs, or pain points that they come to guys for, and they say, “We need to pay for your service to fill these needs that we have.” And then you guys say, “Okay,” and then you’re able to create a case study about how your service benefited Disney, for example, or Warner Bros. And then, when another prospect comes in, and they have the exact same – or very similar pain points or needs as Disney, let’s say.

And they come in to you guys and they’re looking around, and they’re checking out your product and that kind of stuff, you’re able—based on the tagging process—of saying, “Okay, this person is in this category of their needs or their pain points.” You’re able to then trigger an automated sequence to them, let’s say, of emails where you’re sending them relevant information saying: here’s how this particular service worked for Disney, or worked for Warner Bros., or works for a company in a similar position to yours. So, they’re getting relevant information, as opposed to maybe a different way that your service works for a different company that would be less relevant to them.

Sean: That’s exactly right. Yeah, yeah, telling people the stuff that is important to them because there are so many things we could talk about at any given time, but it’s going to fall on deaf ears if that’s not relevant to them.

Matt: Right, and you’ve now been able to automate that, so as your leads come in and you’re able to identify their needs, you’re able to get them into the right automated sequences and get only the relevant information to those people.

Sean: That’s right.

Matt: And therefore have a higher conversion rate, I assume, because they’re getting all of this information that magically is relevant directly to them.

Sean: That’s exactly right.

Matt: Okay, and so then once you’ve delegated and you’ve automated those things, what then is the next step?

Sean: Yeah, so the seventh and final step is what I call “scaling personal attention,” and that’s not my term, that’s actually a guy—Jermaine Griggs—who I think you said you saw at InfusionCon. So, this is one of the most brilliant guys I think out there; he has an incredible story. He’s been kind of a personal mentor to me; I took his course. But his concept is – it’s really a philosophy of how you apply automation, and the way to think about is: basically, how do you deliver a boutique experience at scale?

So, how do you give – people come to boutique stores because they like that one-on-one, concierge, personal touch, but how do you deliver that at scale with millions of visitors? And there is a way to do that in a very tactful manner. Usually, when you think of automation, you think of annoying drip campaigns that you just like unsubscribe, this is spam and whatnot. But if you do it right, it’s actually very helpful to those visitors, you’re servicing them, you’re meeting them on their turf, and you’re connecting with them, and it’s actually – it’s well-received if you do it right.

Matt: Can you give an example of that?

Sean: Yeah, well I think the interactive video is a perfect example, that’s not something that I had seen – I’ve never actually seen that done before, we just kind of – I came up with that idea but based on this concept of scaling personal attention, so this is actually a really good example because it also involves flinstoning: so, we did – our sales process emerged over many calls, and then I documented that using that draw.io flowchart stuff, and then I took that document and made a – stubbed-out a bunch of videos that would allow us to deliver out normal consultative sales process, but entirely done via video.

And really, the best way—if you’re listening, I know this gets kind of abstract—but the best way would be just to go to Pagely.com/explore, maybe put it in the Show Notes, but this is – it’s truly an organic feeling—I think you’d agree—sales consultation.

Matt: Yeah, I’ve gone through it, and I think the way you characterized it to me initially was a choose-your-own-adventure, which I think a lot of people get the concept of what that means. And it’s literally an interactive Choose Your Own Adventure video consultation, which I’ve never seen anything like it, either. And so, can you explain a little bit more? I’ve gone through it, so I know what it is. And I agree, we are definitely going to put that link in the Show Notes because I think people should go and see what you’ve done and what you’re talking about. Because the principles and the concepts are super applicable for any business obviously who are trying to scale personal attention, but can you just describe a little bit about first of all: I guess describe it from the buyer or the prospect experience; and then, the behind-the-scenes a little bit about how you actually built it?

Sean: Yeah, well so let me start with the goals of this project—we have one account exec right now, one SDR—my goal is basically: how do we get Matt in front of more people without consuming his time?

Matt: So, SDR, say what that acronym is?

Sean: Oh, Sales Development Representative.

Matt: And his name is –?

Sean: Chad.

Matt: Chad, and then Matt is –?

Sean: The account executive.

Matt: The account executive, okay. So, I just want to make sure that people have this straight. Okay, so go ahead.

Sean: Yep, so the goal is a couple-part: we wanted to get Matt in front of more people without actually making him physically get on the phone with folks; we also wanted to offer the customer a self-serve option so at midnight if they feel like going through a sales consultation, they don’t have to wait and book a Calendly appointment with us the next day, they can just go – if they’re ready to do it, boom! There’s no reason they shouldn’t be able to go through it.

The other thing this does is: in the background – so it gives people that convenience of being able to experience it on their own terms, but in the background, we’re also logging all of their answers to each of those bullet points. And I decidedly use the exact same structured notetaking process that we use on our sales calls: so it makes use of those exact same tags, we collect all that information, and then I’m able to trigger the exact automations I had already built, that already exist, to then reach out to those folks, and we’ve never even talked to them yet.

Matt: So, yeah, so I went through it and just to share my experience in going through it: it’s basically a video, and you just click on the video to play it like you would a normal video; and then your sales guy Matt comes on, and welcomes me there, and gives me some basic information and different stuff. And then he asks me a question, and he says, “Would you like to do this – or would like more information about this, or would you like to go – would you like this other thing instead?”

And he asks me a question, and he says, “Choose now,” and I get to click a button to go one way or the other, which is the Choose Your Own Adventure thing, and I was like, “Oh, that’s cool! I want to”—click—“I want more information on this thing here,” and I click the button, and then immediately he responds to the button that I clicked. So, I said, “I want more information on this thing,” or “I want to understand more about this,” and I clicked on it. And then he says, “Cool!” and then he tells me exactly what the button said, what he just asked me if I wanted to know, and then when we get to the end of him explaining that, he says, “Okay, cool! At this point do you want this, or do you want that?”

And so, at the end of each video clip—which is just like a few minutes long, each one, let’s say—he’s asking me, “Do you want to go here or here?” So, it’s like one video screen, but I’m just clicking the answers to his questions, and based on what I want, I’m directing his conversation and getting the replies from him that I’m most interested in.

Sean: Yeah, I don’t know if – maybe the people listening have seen that thing Robot Chicken, or if you remember that from back-in-the-day? But it’s essentially Robot Chicken with a sales process. You’re getting to dictate the flow of the sales process: what do you want to talk about next; you want to talk about our scalability, our security, our speed, or whatever?

Matt: Right.

Sean: You get to guide that discussion, but on the backend kind of the nice thing for us is we’re logging all those answers that I’m then able to make use of with highly targeted follow-up.

Matt: Right, so each time I – when I went through your site and when I went through this Choose Your Own Adventure video experience, each time I clicked a button and told Matt what I wanted more information on or what my situation was – because he’ll ask – I mean, he’ll ask qualifying questions too, right? Or he’ll ask me to designate like, “Oh, if you’re a small business, or a such-and-such, click this,” I thought, “Oh, okay, cool,” and boom! And then it’s, “Oh, cool, for businesses we do such-and-such,” or whatever it may be, right?

Sean: Yeah.

Matt: And so then, each time I’m doing that, I’m giving you more information about myself, which I’m happy to do because it’s customizing the value that you’re able to give me because you’re going to then – he’s going to then speak to me about my specific situation which is what I want. But you’re also capturing and auto-tagging me as a prospect with that information so that if I haven’t let’s say bought the service by the end of the call, you’re now able to put me into your automated drip marketing follow-up with those case studies or information that are applicable specifically to my needs.

So, you know I’m a small business, you know my pain points are this, you know I’m interested in this because I’ve clicked all that stuff, and now you’re able to just hit me with information that’s directly, immediately, and customized, applicable just to me.

Sean: Yeah, and that’s exactly – the email that you’re going to get after that is going to be, “Matt, you related on our call that you’re a small business, and here’s a great case study for you to check out, this is what we did for this other small business. You shared with me that you are also concerned about security, here’s why security’s important.” So, I can hit you, I know exactly the pain triggers, and pain points, and psychological things that I need to do in each of those emails, so it’s – yeah, it’s really been a boon.

Matt: And you’ve now automated that entire process, but it’s in a very customized way; and by the end of the video, I feel like I know your sales guy, Matt.

Sean: Yeah. That’s the other thing, yeah, it prizes – so something we’ve noticed is our no-shows have drastically decreased. For the people that go through that – so folks who go through what we call “Bottled Beard”—that’s the code name for it, and you’ll see why if you do it—but people who go through Bottled Beard are 58 percent more likely to close, so it’s a really – it has a dramatic effect on closings. But yeah, just like the value of every lead that goes through that, we make a huge effort to push people through it.

Matt: Yeah, but I really like that aspect about humanizing your salesperson that I’m going to be in touch with—and I feel like I already know him by the end of the video, even though he doesn’t know, right?

Sean: Yeah.

Matt: And for people that have seen the Nick Nimmin episode of The Maverick Show, one of the things he talks about as a YouTube expert, he talks about the concept of building parasocial relationships with people that watch your videos, which is a one-sided relationship, because they feel that they know you—even though you obviously have never met and don’t know anything about them—because they’ve seen you on a video, so they see your personality, they kind of know you, and this kind of stuff.

So, you’re really humanizing yourself and starting to build that rapport, so I’m sure by the time Matt actually gets on a live consult with one of those buyers, they’re much more comfortable with him, feel that they know him and that they’ve already gotten up-front value from him.

Sean: Yeah, well so first off, before you even get there, the no-show rate declines, so they’re more likely to get on the phone because we’re actually – subtly what we’re doing is we’re prizing Matt, we’re saying, “If you want to speak to Matt, you can book a call. You’ve just now gone through this thing,” but once they see what a rock star he is, they’re like, “Man, I hope I can – I’m definitely not going to miss this appointment.” Whereas, people who don’t know who he is don’t have that, they’re just thinking, “Oh, it’s some sales guy, I can blow this off.” So, we see the no-show rate go down; you’re right, the rapport on the call is instantly there, they feel like they know him.

I would imagine you with a podcast are going to experience some of this yourself at some point, once you’re in places, and people will recognize your voice, and they know you, but you don’t known them, it’s definitely a real social media phenomenon that I think –

Matt: Yeah, for sure, people that are going to hear this episode, it’s like, “Oh, now they know I was in Brazil,” and they know all this stuff, and they know about some of our experiences here. And then, as people listen to you they know more and more about you; so yeah, definitely solid. So, can you talk a little bit about – for people that are listening that have a company, and they run a sales department, and they’re like, “Yo, that sounds really epic!” I want to try to give them as much value as we can, can you talk a little bit about the backend: how you built this, what software programs you use to do this, and what from the backend of the sales department side it actually looks like to create something like this?

Sean: Sure. So, everything starts with planning. Well, so right off the bat, so the platform that I used for the interactive video it’s called Dot.vu—so Dot, D-O-T.vu—is that system. Zapier is the glue, it’s basically like a message bus. So, Dot.vu sends stuff to Zapier, Zapier is kind of like this switchyard thing that determines what needs to happen, and then it pushes the leads into our CRM system, which is Active Campaign. So, those are the three technological pieces to this, but everything starts with planning. So, the very first thing that you need to do is actually sit down with a blank slate—draw.io is that flowcharting software, I highly recommend it.

But just sit down and really try to map-out: what is that sales process? Just do a decision tree diagram: what are the yes/no questions; where do you send people, and just map all that out. And the processes of doing that – even if you don’t do anything with what we’re talking about technologically, just going through that process is invaluable to understand your sales process. They say – the quote that I love is: “If you can’t describe what you’re doing as a process, you don’t know what you’re doing.” And so, go through that, and map it out at the very least, if you do nothing else, do that much.

Matt: Awesome! So, then they use the – if they were to use the dot.vu actual software program, and they were to pay for that service in the way that Pagely has paid for that service, what then is the process for actually creating that interactive video? What does it look like on the backend, technologically?

Sean: Yeah, it’s a lot like the Flash IDE, I don’t know how to describe it. I mean, it’s pretty daunting interface the first time you see it; it does make a lot of sense once you use it, but there is a steep learning curve. What it’s doing behind the scenes is actually taking a single YouTube video, and it’s overlaying HTML5 screens on top of it that then jump you to various timestamps within that video. And the net result of all that is what feels to be—as you experienced—just this organic kind of adaptive video experience; but that’s what it’s doing under the hood.

Matt: Got it. And so, that’s really the way that – so, it’s asking me to choose something, I’m choosing something that is, first of all, registering in your system my choice, so you know more about me, you know how to market to me; the other thing it’s doing is jumping me to a timestamp in the video where it appears to me like all of a sudden, I’m on a brand new video, and he’s answering my questions. But it’s the same screen of course, and that’s because, in fact, he has just recorded all the answers to all of the questions, and so whichever one I say I want to hear about, the software behind the hood – or under the hood, is just jumping me to the timestamp where I’ll then get the answer I requested.

Sean: Yeah, that’s exactly it.

Matt: Awesome.

Sean: I think there are 72 videos that we had to shoot in the thing that you saw. And of course, you only – at the end of the day I think you saw like eight of them, right?

Matt: Yeah. Yeah, exactly, because there are so many different choices that people could have, and that’s why it’s so comprehensive, and why it’s so meaningful, and real.

Sean: Right.

Matt: Because there are so many different specifics that you could choose and get the specific answer for that, which is why it’s relevant. It’s not just some shallow, automated, generic thing, it’s actually giving real substantive answers to most of the questions and scenarios people would have, but on video.

Sean: But this is also why we flintstone it because you would never want to dive into this. If you don’t have your product and your sales process figured out, it’s foolish to even try to build something like this up front, you’re just going to fumble. You really need to get that all down pat, diagram it all out, and then this is like the very last step. Entrepreneurship is a game of leverage and – this is a very high-leverage thing you can do at that point where you truly understand it, and you can take the person out of the process and just automate everything, so.

Matt: Right. And now, you are also doing some other pretty cutting-edge sales techniques that you’ve developed and conceptualized, and you’re now implementing some pretty advanced stuff—which I was very intrigued by—and you have amazing names for them. You just alluded a minute ago to the Dr. Dre project, and the Mr. Miyagi project, and some of those things, which is just amazing, you guys internally must have an absolute blast at Pagely! I love that! But can you talk a little bit about what some of those projects actually are?

Sean: Yeah, let’s talk about that one; I mean, that’s the most recent thing that I’m working on. So, this is – basically, I am able to operate in either a sales capacity or a marketing capacity. Right now, marketing is our biggest bottleneck, so I have hopped the departmental fence to go assist the marketing team in helping generate more leads; so that’s kind of the backstory. What this is, is a two-part thing: so Dr. Dre is what I would think of as the fuel source towards this effort; Mr. Miyagi is the engine. And the idea is that we have a very high-dollar, premium, B2B SaaS product that we sell to companies like Disney.

Matt: Can you say what “SaaS” stands for?

Sean: Oh, yeah: Software as a Service. So, this is something where getting the right people – leads to us are extremely valuable if they’re from the right companies.

Matt: Because you’re – and just to be clear, you’re only selling business-to-businesses, this is not a business-to-consumer company. So, your clients are all businesses, and they’re major businesses.

Sean: Correct.

Matt: Disney, Warner Bros., that caliber of enterprise.

Sean: Fortune 500, exactly.

Matt: Right.

Sean: Yeah, so the leads – it’s not a high-volume game, it’s a really targeted how-do-we-get-those-upper-echelon-leads? And so, what this particular system – or tandem systems that I envisioned, so we get a fair amount of traffic, and extracting more value out of that traffic was my goal; not to go try to find new traffic sources, but how do we get more out of the people that are already visiting our site? So, that’s the goal, and the approach here was basically: I am able through reverse IP look-up—which is a fancy name for doing some technical stuff to see – based on your IP address to take a guess at what company you are.

It doesn’t work with VPNs and things where people are using a public Internet access point, or whatever; but it does work – since a lot of these people are companies that I’m able to do a reverse IP lookup: get what company they’re coming from, take a guess as to that, and then I can go to LinkedIn—and all this is automated—so, I get that, I get the company name, I go to LinkedIn, I pull the five people that are most high-priority targets for us at that company—so those would be people that have either the term “marketing” or “IT” in their title—so I pull those upper-level management people.

And then I bring them into a system, we get a bunch of other demographic data about them, and I load them into something called ReplyApp, which is where we do our automated cold outreach. And yeah, so we basically do a cascading outreach, this is the Mr. Miyagi part—that former piece that I just described was Dr. Dre—Mr. Miyagi is the nurturing engine, basically, that goes through and cascades through each one of those stakeholders and says, “Hey, we noticed that someone from your team was investigating Pagely, just want to make sure you’re getting all your answers.”

And we have cadence to five different people in the organization, cascades through a series of emails, if it doesn’t work on that first person, it falls back to the next target.

Matt: So, just to sort of reiterate that and make sure that I’m understanding that properly: this is for a lead who comes, looks around in your website, but does not opt-in and provide their company information, and their contact information? They just maybe come, check-out the site?

Sean: That’s correct.

Matt: And you’re able to identify what IP address they’re coming from—assuming they’re checking it out from their office, or whatever—and say, “Oh, they’re from this major company,” and then you’re able to go on LinkedIn and pick out five people from that company that are relevant, right? That would be decision-makers with respect to potentially buying a service like Pagely?

Sean: Yep.

Matt: And then, you’re able to outreach directly to them, and send a personal email say, “Hey, I think somebody from your company was checking-out our website, just wanted to make sure you got all questions answered,” so it’s a personal email from you to them. And then, if they don’t respond—this is the part that I think is really remarkable—if that person doesn’t respond, like if it’s Adrianna is the first person you send it to let’s say, and Adrianna doesn’t respond, you’re able to then send it to the second person that you pulled from that company who would potentially be relevant, let’s say that person’s name is Joe.

And then, your email says, “Hey, Joe, I just contacted Adrianna about this thing,” and so there’s actually an interpersonal connection that you’re making between people in the same company in this email follow-up.

Sean: That’s exactly right, yeah. And this thing is a week in service now, we just deployed it a week ago, and we’ve already seen some pretty promising early results. And I think you nailed it: it’s that interpersonal – when you see someone’s name, you know the person, they’re a co-worker, and it’s couched in a very helpful way, it says: “Hey, Joe, I had reached out to Adrianna, and maybe she’s on vacation, I was wondering maybe if you’re the more appropriate person for me to be talking to about this?” that’s it; it’s that simple.

Matt: Right, and they know that it’s – it’s very different, they know it’s not a spam email, or some generic thing because you’re referencing another person in their company, and you’ve actually taken the time to go and look them up on LinkedIn, you actually have this information about them, it’s a personal email, and now you’re referencing someone else in their company, so they’re like, “Okay, this is at least not some generic spam email.”

Sean: That’s right.

Matt: That they’re getting, and so they know that, and so the likelihood of their response is going to be significantly higher, I would imagine?

Sean: Yeah. Yeah, and this is another example of that scaling personal attention. This is exactly what someone would be doing if we were to take an intern and put them on this task, only we’ve now automated it to a machine level.

Matt: And if that second person doesn’t respond, it then goes to the third person, and you have a cascading situation where it says – then it says, “I reached out to Adrianna and Joe, and neither of them responded, I thought you might be the right person,” and it goes cascading through all five people like that mentioning the names of their colleagues that you have tried to reach out to. And all of this: from pulling the information off of LinkedIn, to sending the initial email, to cascading down the list of the five people if none of them respond, you’ve automated the entire process.

Sean: So, we’ve automated up to the point – so the part that we are flinstoning right now—and it’s decidedly this way—is choosing who to email, and prioritizing those outreach. We use a system that I think of like an exoskeleton, it lets us do a lot of this without as much work, but that’s the function that ReplyApp performs. So, yeah, just choosing those priorities is all manual right now, putting them into the cadence; but then all that outreach is automated.

Matt: Well, super-exciting, and super-innovative to see where you’re going with all of this stuff! And what’s also been super-awesome to see is your ability to execute all this stuff, and design it while traveling the world, and being fully remote, and being in a different country and a different continent than most of your co-workers! Which is awesome.

Sean: Which has been something I don’t think I put in the – I don’t even think I’ve told you this, but the largest sale that I closed for the company was actually in a Moroccan bowling alley. And I don’t know if you know Rhonda, maybe you’ve met her, maybe – I don’t know, but she was an awesome girl in our group, you got to meet her. But she was throwing this event, it was at a Moroccan bowling alley—and I can’t name the client, unfortunately—but it was the biggest deal in the company history. And it closed, I literally got the PO – I have a picture of me holding up the PO in front of the bowling pins, and she’s controlling the music, and she throws on: “All I Do Is Win.” It was just one of the highlights, one of those moments.

Matt: That’s amazing! I mean, this is the nomad life that you’re able to do all this stuff, and run all the things at this level, deal with Fortune 500 caliber clients, close those types of deals, and be able to do it from a Moroccan bowling alley, or the beach in Brazil, or anywhere else, you know? I mean, and this I think is really significant; so let’s talk a little bit about travel, because I know that’s – the nomad lifestyle is something that’s been really important to you, and travel has been a really big part of your lifestyle.

And maybe, let’s just start back, way before Remote Year, way before your decision to become a full-time nomad, when you were first starting to travel outside the country when you were studying abroad in college. Can you tell us a little bit about what your initial experiences were internationally when you went outside the country by yourself?

Sean: So, that was quite a while ago—I’m going to date myself—but that was ‘95, and it was in college, and I went to Quito, Ecuador to live for six months. And it was just one of those completely eye-opening experiences; it was my first time out of the country. I learned to paraglide that trip, I got certified as a paraglider; I climbed a 19,700-foot active volcano, the largest one in South America, Cotopaxi; swam with the seals in the Galapagos. And it was just like – we lived in the rain forest for two weeks with a shaman, and got to – it was just a mind-blowing experience having never been outside the country prior to that. So, I think that really primed me and got this travel bug.

Matt: And on that experience when you were abroad, did you have highs, and did you have lows? Did you have travel snafus and things? And how did you cope with that, how did you deal with that, how did you process it all? I mean, maybe tell us what stories if any from that period in your life really stand out? What are kind of your top memories from that period abroad in Ecuador? And then, ultimately, what did you take from that?

Sean: Sure. Okay, so literally, the highest high would’ve been Cotopaxi at 19,700; we summited that. It was myself and this other guy—Ecuadorian guy, Frank, that I met there—and that was a crazy experience. We slept – we went to the refuge which was at like 14,000 feet, and at midnight we started walking up this enormous mountain, and I don’t think I really fully internalized how big of a mountain we were climbing.

Matt: So, this is the single largest active volcano in all of South America?

Sean: Correct, yeah, Cotopaxi. Yeah, so we leave at midnight, and we summited somewhere around 7:00 a.m., like right as the sun’s coming up, and you’re not supposed to be on top once the sun is up. So, we really didn’t have much time; we had like 15 minutes on the summit because there’s dangers of avalanche, and you’ve got – you literally were hopping crevasses; I mean, it’s legit dangerous stuff. And so, we’re roped-in, and we’re on the summit taking pictures, I’ve got some amazing photos from up there.

And then, we start our way down, and about 30 minutes on the way down your legs are just Jell-O at this point because we’ve been hiking for seven hours in almost zero oxygen, you know? So, hiking down the mountain, my crampons lock up. So, crampons for the people listening are those little teeth that you put on your boots that allow you to grip the snow, and ice, and whatnot. So, the teeth in my boots gripped each other and locked up, and I went over the edge. And I did what you’re supposed to do: I threw my ice axe and start sliding down this very steep-grade thing, it was like a 70-degree – yeah, it was ridiculous.

Fortunately, the guy that I was with was a very experienced mountain climber, so Frank knew exactly what to do: he jumped over the other side, threw his ice axe—he was a little guy, I’m 6’7” like 210; he is a little Ecuadorian guy—but he was able to – between us, between my ice axe and his ice axe, we were able to arrest my fall because I would’ve – we would not be having this interview right now!

Matt: Wow! So, wait, when you say “over the edge,” do you mean you were at the top of the volcano, at the summit?

Sean: We were about 90 percent up to the top at that point; we were on our way back down, so we were about an hour back down.

Matt: Wow!

Sean: Yeah.
Matt: And then, you put your ice axe –.

Sean: I’m sliding down at this point, maybe – I don’t even know what it is that, like a 70 percent grade? I’m sliding on a very steep hill at this point, and I just jammed my ice axe – it’s roped around your hand, you throw it into the ground as hard as you can, and it just starts to slow you down. But between that – I was roped into Frank, so he’s over – he’s basically diving over the other edge to counterbalance my descent, it was nuts!

Matt: Wow!

Sean: Yeah.

Matt: And then, when he threw his ice axe in, and you had yours in, he was able to slow your fall to a stop?

Sean: I slowed it, and then he – basically, when the rope caught, he was on the other side of it already, and so the two of us were just basically laying there draped over this mountaintop.

Matt: And then, you both had to then climb back up –

Sean: Correct, yeah.

Matt: – your respective sides, which you were able to do in a balancing act and both make it back up?

Sean: Yes.

Matt: That’s amazing!

Sean: It was bananas. I would – honestly, I would not climb another mountain like that again. I did it; I have no desire to do that again.

Matt: You got the picture to show for it! You got the story to tell on The Maverick Show.

Sean: There wasn’t really Instagram at that point!

Matt: Yeah, exactly, that was pre-Instagram! Wow, that’s amazing! And then, as you were living in Ecuador, were there any other experiences that stand out: travel snafus, different things that you sort of came across at that young age?
Sean: Yeah, for sure. So, I think the biggest snafu we had: there was a group of us – so this was an exchange program with 17 people, and I think a group of six of us did a side trip to Atacames, which is on the beach; Manta and Atacames are right there. So, we went from Quito to Atacames, and we didn’t know what we were getting into, this was just the ill-fated trip. We get in this bus, the bus drives for a few hours—leaves in the morning—we get to a road that’s been washed-out; it’s a literal mudslide, so you can’t – the entire road is just unpassable. So, everyone gets out, they take all their stuff, and we just trudge through the mud with all of our belongings to the other side of this thing, get picked up by a different bus.

There was a dump truck involved at some point where we had to all pile into the back of a dump truck. Anyway, long story short, we didn’t make it to the town in time—we thought we’d be there at a normal hour—but by the time all this is over and said and done, we get to the half-way point—we’re in a little town called Imbabura—and we arrive and it’s like 10:00 at night. And in a normal-size town, that would be no problem, there’d be a hotel with a front desk and whatnot; but in this town, everyone was asleep, there was literally not a soul awake in this town!

So, six travelers, freezing cold—this is in the middle of winter—we’re in this little town, and we were like, “What do we do? We’re going to freeze; we can’t sleep on the street.” So, we wander around, and eventually, we found an ATM booth, and so we literally – we spent that night—six of us huddled together, body heat—in an ATM booth, in Imbabura; made it to Atacames the next day. There was more craziness to that trip, but yeah, that’s probably the biggest travel snafu I’ve ever been involved with.

Matt: That’s amazing! Now, are you today still in touch with any of those six people?

Sean: I am, yeah. Yeah, Koby Johns is a firefighter; he’s now a captain in Fresno. He’s probably the one that I see most; he’s on Instagram now.

Matt: That’s amazing! And so, then, fast forward to your current choice to live a nomadic lifestyle. And you had a job with Pagely, and you had a really good career, and you had all this stuff going on, what was it that made you decide to go and be a digital nomad, and to go and travel the world in the way that you have over the last number of years?
Sean: Yeah, I think the desire has always been there. I got kind of sidetracked for a while and – I have just a super rambling, weird career trajectory: I’ve worked as like a 3D animator; I have a real estate license; I was an EMT at one point; I’ve been a computer programmer of eight years, so I’ve done a number of things. I wrote a post 10 years – exactly 10 years prior to Remote Year, and it was when I was working remotely in Cabo, and I just – it said, “I’m going to do this, I’m going to travel the world, and this is the new lifestyle, and this can be done independently.

Unfortunately, I went back to the US and ended up starting a company called JumpBox that ran for 10 years, so it was like a 10-year kind of derailment of that effort. But then, when Pagely came around – that company we ultimately wound down, and then Pagely came along; was with them for a year, and then it was like all the stars came in alignment and facilitated it.

Matt: And what was your – when you decided to go, and Remote Year was your first, and that was the initial impetus, right? That got you from where you were based in the United States to saying, “I’m going to actually go and travel the world, and travel around, and work remotely, and I’m going to do this,” at this point in your life—when you were reactivating that nomadic spirit, and that desire for travel—it was the Remote Year opportunity that was your first inclination that ended up getting you actually out of the United States, and then you’ve obviously continued subsequently, is that right? And how did that sort of – how did that sort of impact you?

I mean, I want you to explain what Remote Year is for people that have maybe never heard of it, or they don’t know about it, what is Remote Year, and what was that experience like for you? What did that mean to you in your life at that point when you were able to do that trip?

Sean: Yeah, so Remote Year – well actually, let me back up just a previous step to that because it’s an interesting story of how that came to pass. So, I was actually working for Pagely like I said for a year, contemplating: how do I take advantage of this fact that I’m totally remote? The entire company is distributed, it’s an entirely virtual company, so I’m like, “This is silly for me to be working out of my apartment when I could be anywhere.” So, I started looking into the possibility of doing a US road trip, so reconnecting with a bunch of people I hadn’t seen in a while.
I started plotting this road trip, but the deeper I got into it, the more I realized that this is just not going to be feasible as a solo driver, and plotting the next thing, and where I’m going to stay that night, and then driving, and then all that while trying to work for Pagely, it was just going to be completely infeasible to be productive throughout that; so, I kind of gave up on that vision. But about that time my buddy, Chris—who was a neighbor who actually lived a block away from me in Arizona—he came over to my house one night in Arcadia, and he says, “I got accepted to this thing, I would love to do it, but I don’t know how you work remotely. You have a remote job; can you just tell me how you do your job remotely?”

So, he and I start talking, but he’s describing Remote Year and what he got into, and I’m like, “Man! This is what I need to do my – what I want to do with the US road trip, only it’s international. It’s going to all these amazing places.” So, he’s just describing it, and my jaw drops, and I’m like, “Dude, you definitely need to do this, first of all. I will help you work remotely; you can learn that. But yeah, absolutely, you’re doing this, and I’m going to do this with you!” So, yeah, we ended up both traveling, we were in Darién, and we did a year together, it was amazing.

But in terms of Remote Year, what that is: so it is basically a travel program that takes people with location-independent work, and they travel as a unit for one year—basically 12 months, 12 cities—and it provides the infrastructure: the flights, the accommodations, the workspace, activities, all the stuff to facilitate that.

Matt: Yeah, and I did Remote Year as well, which as I said in the beginning is how you and I eventually met through that alumni network. I was about probably three groups behind you; you started I think in May of 2016?

Sean: That’s right.

Matt: And I started in September of 2016, so I was like a few behind you. And so, you and I never met because our groups never crossed paths in the alumni network then. Now there’s just thousands of people that have gone through Remote Year, have completed Remote Year, and it’s just such an amazing network meeting people like you, and like a number of our common friends that we have now.

But it’s like anywhere in the world that I now go – I was just in, for example, Nairobi, Kenya for a month earlier this year with a different program called Wanderist Life, and they did a month-long experience program there, and brought a community together, and provided us housing, and workspace, and everything else. So, I was there with Wanderist Life, and I just threw out to the Remote Year channel, I was like, “By any chance is anybody going to be in Nairobi in September?” and six people were like, “Yep, I’ll be in Nairobi in September!” I was like, “You have to be kidding me!” and I didn’t know any of them because they were all from different Remote Year cohorts, right?

They weren’t from my group, but they were from different Remote Year cohorts, and they’re in this alumni network. And so, I met up with six Remote year people that I had never met, including – and one of them was Kenyan, who had done a Remote Year. So, he brought a whole Kenyan crew of people—who, of course, were at least as interesting as Remote Year people! You would not believe – one of the Kenyan guys that he brought that was his buddy – it was interesting because I was going from Nairobi, and I was going to go to Kyoto directly from Nairobi, and I was going to spend five weeks in Kyoto, and this was my last week in Nairobi when I met up with them.

He said, “Oh, yeah, what are you doing?” and I said, “So, yeah, I’m going to go to Japan, and I’m going to spend five weeks there in Kyoto.” And his Kenyan friend—born and raised in Nairobi—he was like, “Oh! That’s great!” he’s like, “Yeah, I just lived in Japan for seven years, I speak fluent Japanese,” and all this kind of stuff, this Kenyan guy! He’s sitting there, having a drink with me in Nairobi, he speaks fluent Japanese, he just lived in Japan for seven years, right? I’m like, “Really? That’s insane! Can you make some recommendations?” or whatever; he’s like, “Oh, yeah, yeah, I did this, and this, and this,” and all this stuff.

I mean, it’s just like the networking of these types of – and this guy had never done Remote Year; the Kenyan guy that did Remote Year was his buddy—which is how I met him—but as fascinating as anybody I’ve ever met in these circles and stuff. And so, it’s just amazing how these networks work!

Sean: Yeah, and that was something where going into Remote Year, I don’t know – I certainly didn’t foresee that being a benefit of it, I had no idea that this whole citizen/alumni thing would exist. It was really more about like, for me, solving the logistical issues—which was a different reason for you, I know it was more for the community for you; it morphed into that. I think people come to it thinking, “Oh, yeah, I just need someone to solve those logistics,” 100 percent of the time though, three months in you realize it is all about the community.

Matt: All about it. And I had been nomading around for a while before Remote year, and for me when I saw that I was like: they’re going to bring 40-plus people together that are going to be coming into this with the stated intention of leaving all of the people that they know, and their whatever behind, and traveling the world with a bunch of strangers for a year! Anybody’s that’s willing to do that is by definition an interesting person that I want to meet, and I want to hear their story!

Sean: Correct.

Matt: Period. And they’re making a commitment to being part of, and developing, and cultivating an intentional community with that travel group for the scope of the entire year, which means that the depth of those relationships, of living with people for an entire year, is just – I mean, incredible!

Sean: Yeah, you said it. I think it was the best year of my life; I think it was the same for you.

Matt: Yeah, for me as well. I mean, it was just – it was just totally incredible. Everybody that finished the program with our Remote Year group, we still have a chat – a Facebook chat group where we’re literally posting I dare say every single day, like 15 months after it’s over, you know what I mean? I mean, that for me is like – it’s family for life, you know what I mean? Any time I’m ever near any city where those people are, any time people need anything, any time – everybody’s doing their own thing, and we’re all supporting each other, and it’s just – it’s like a family for life thing! It’s just – it’s amazing.

And like at this age too it’s really amazing to be able to have that and to experience that. Because I talk to people and I’m like – people that are let’s say they live in a city, and I say to them, “Think about your – in your 30s or in your 40s—whatever it is—think about who your top let’s say three best friends are in your city, right? And then, if they don’t work with you in your office, how often do you actually see those people in person? “And maybe let’s take your No.1 best friend out of it, but take best friend No.2 and No. 3, how often do you actually see them?” and most people are like, “Um, once every like three or four weeks?” and it was like, “Oh, we should really get coffee, we should really go out to dinner, we should really catch up,” you know? And you see them once-a-month, or once every whatever, in Remote Year you see these people every day! I mean, that’s an amazing level of connection and depth that you just don’t have in a regular life!

Sean: And I think the other element that maybe isn’t as obvious, but I think is absolutely every bit as important, is that diversity. So, you’re talking diversity across age, obviously gender, sexual orientation, race, ethnicity, you name it, it’s just like this amalgamation of the most unlikely crew of people to travel together that ends up just becoming so close.

Matt: Yeah, and really, it’s like you’re going to meet some of the best friends that you’ve ever had, and some people that you connect with on an insane level. But even the people that let’s say are the furthest out from the type of person—if you want to call it that—that you’d normally be friends with, or somebody that’s like outside of your – has no perceived initial shared interest with you, whatever it is, they all do have in common: the fact that they’re passionate about world travel; they’re willing to leave everything behind, and then travel the world with a bunch of strangers for a year, and they’re committed to building a community with you, you know what I mean?

So, whoever was like the farthest from me of who I would normally be—whatever you want to call it—friends with or whatever, that person—even the farthest end out of that community—the fact that they were committed to me, and they were committed to building a community, an intentional community with me, and they had my back for a year, every single human being in that group is family for life, for me. Period. Like end of story, you know?

And your year will just I think bear that out, and reflect that in terms of how many different moments like down times, or whatever, that different people were there for you, and people you weren’t even that close to let’s say all of a sudden, they’re like there for you in this crazy moment, and you just connect with them. And then the depth just goes, and then all of a sudden for the rest of the year you’re like, “Wow!” and you’re viewing that person differently, you know what I mean? So, it was just – it was amazing!

Sean: Yeah, and I mean if it’s any testimonial, we had our one-year reunion after our group finished; so that was in June this year in Prague, which was the first city we went to on Remote Year. And we had finished with 50, and I think 36 of them came back to Prague. So, if that’s any testament, I mean, we had a really strong group.

Matt: That’s amazing. So, for you, after that year, what would you say— just reflecting back on your personal growth—what – in what ways do you view the world differently, or what can you now not – what do you now see differently, or what are sort of your personal growth reflections on what—pre-Remote Year, and post-Remote Year—what that travel experience did for you?

Sean: I mean, if I had to distill to one adjective, or one—I guess it’s a noun, I don’t know—but tolerance; being able to recognize that every situation is not as bad as it seems. And like, you’re going to just deal with so many inevitable little annoyances and things that don’t work quite right, I think we kind of spoiled in the US of – or we take for granted at least a lot of things that work extremely well, but that’s all we’ve ever known and therefore, we don’t have any perspective of anything other than that.

And so, I mean, Remote Year to me was like this weightlifting exercise in virtues like tolerance, and resilience, and patience, and just – I don’t know, virtues like that, that I think make us all better people having done it.

Matt: Totally agree. And what about travel in particular? I mean, Remote Year included, but also your travel outside of Remote Year, your experiences living abroad in different places for extended periods of time outside Remote Year? Everything all included together, why do you travel? What does travel mean to you? What do you get out of travel itself?

Sean: A number of things: so, I think it provides this constant stimulation that keeps you just – I don’t know, to me it feels like this is living. This is how we’re – we’re meant to lead extraordinary lives, and somehow along the way we get kind of lulled into a sedentary lifestyle where we’re expected to go to a 9:00 to 5:00, and expected to be in a cubicle, and somehow people get the idea that that’s normal; to me, this is how we’re meant to live. I think—this is a weird thought—but to me, we are hardwired – as a species we’ve lived in tribes far longer than we haven’t.

And I think there’s something that is unacknowledged with this whole travel program thing where Remote Year provided like the modern-day tribe; you felt it. It’s a squad, it’s your people, and you’re moving as a unit from place-to-place. And I don’t think we can underestimate the value of returning to this tribal existence, I think there’s something incredibly powerful about that, that just like—at least in my situation—it awakened me, it revitalized me. I was in kind of a social rut prior to going into Remote Year, and it just like shocked me back to life, for lack of a better word.

Matt: That’s amazing. How do you see the future of remote work, and how do you see the evolution of the digital nomad ecosystem? I mean, I just go back to like when I started traveling, I became a full-time digital nomad. And what I mean by that is I got rid of my home base—got rid of my apartment entirely, I had no home base—and sold my car, sold my stuff, downsized my possessions, and I started traveling the world in 2013. At that time, Remote Year did not exist, nor did any other work-travel programs. I was thankful at that moment that Airbnb existed, I was like, “Airbnb is amazing!” you know what I mean?

I was like, prior to Airbnb I would have to either stay in a hotel, or rent a long-term apartment that I’d find through a broker, or whatever. Airbnb I can just pick a city, and stay for 37 nights if I want, exactly when I want to come and go, and I can take an Uber to the airport, to my Airbnb and back, and it’s crazy! I don’t even have to speak the language, I can just order an Uber, and it just takes me there! And then I stay in an apartment for how long I want, and isn’t this insane? Because 10 years before 2013, none of that existed, there was no Uber, there was no Airbnb; you really would’ve had to either rent a long-term apartment or you rent a hotel, right?

And so, I was just so thankful in 2013 about all of this crazy stuff that was there. And now, literally five years later, the evolution of the digital nomad ecosystem, and the ease with which people can travel the world, and ingratiate themselves in amazing communities at pretty much all times is just unbelievable! So, I mean, I put the question to you just in terms of like what you see as the future of work—both from a business perspective, corporate perspective, that kind of stuff in terms of remote work—but also in terms of the digital nomad ecosystem, the way that this is evolving, and where it’s going, what do you think?

Sean: Yeah, I mean, I don’t see work going backwards; I don’t see us returning to a primarily office-centric environment, at least for a while. Maybe there will be some weird backlash/pendulum swing later, but I think we’re still on the up-and-up in terms of more people doing – making this transition to this type of lifestyle. Remote work in general, even if you don’t go nomadic in the sense – like you’ve been traveling for five years now, not everyone has to go to – you wade into this at a pace which is comfortable to you, and I think we’ll see more of that.

I think technologies like Slack and Zoom, and these tools that we use now that really make it so there’s no reason you need to be in an office, and there’s actually a lot of advantages to not being in the same office as everyone. Personally, I can say that I felt the time zone offset was actually a super-helpful thing in our case: it forced some issues, it created a – it made it very obvious the hiring that needed to occur, it also gave me a lot more white space to be able to act strategically versus being very reactive, and living out of my Inbox. So, it had a lot of advantages, not to mention just the creative stimulation of being in all those places.

But yeah, there’s so many benefits to this, and it’s becoming like the – what do you call it? The geoarbitrage, or whatever, that idea of: being in cheaper places; getting paid an American salary, your money goes further so you can stay there longer. There are just so many reasons why this makes sense now, and the barriers to doing it are basically falling away. So, I don’t see it – I only see it increasing in the near term.

Matt: I want to ask you about the Nomad Prep Academy that you created, can you talk about: first of all, what inspired you to create that; who it’s for; what the purpose of it is? And then, maybe describe a little bit about what it actually is for people that are interested?

Sean: Sure. Yeah, so the Nomad Prep Academy is an online course, it’s a two-week course that I created that attempted to distill everything that I learned from my travels, and make it so I can help more people make this transition, basically. I just see this as being so valuable that I’ve devoted all my spare time really—between that and the podcast, and Nomad Bloggers—to making these properties that demystify this lifestyle change. It came about, I was working in Mexico City at the WeWork, and I was sharing – basically sitting at a desk with a bunch of other Remote Year what are called “PAs,” which are essentially their sales development representatives.

And I overheard a bunch of phone conversations, I heard all the questions being asked, I heard the repetitive nature of everything, and I said, “You know what? I can make something that will address all those questions and more, and inspire people to want to do this.” And so, I put it into a format; I put a lot of time into making basically the tool – the onboarding tool that I wish I had in going into Remote Year.

And so, yeah, it’s got gamification, it’s got some inspiring – not just educational content, but inspiring content that keeps people motivated to do it; it uses all the automation that we talked about. So, it just basically takes everything I know how to do, and I built the best thing that I could build to help people make this transition.

Matt: So, for people that are interested in exploring and learning about how they might be able to make that transition, right? As like your buddy who came to you with the Remote Year proposition, and he said, “Oh, man, I want to do this Remote Year thing, how do I do this? How do I create this? How do I transition into this?” or whatever it may be. For somebody that maybe is working at a regular job right now, or they’re maybe trying to figure out how to get into this, maybe they listen to The Maverick Show podcast and they hear the types of people I have come on, and they say, “How do I get into the game?” or “How does this stuff apply to me particularly?”

The Nomad Prep Academy, does it talk about how to talk to your employer about working remotely? Does it talk about – or how to get into a remote income situation? Or is it more just the preparation for the lifestyle once you’ve achieved that?

Sean: So, it approaches it the way that I would approach a startup in terms of de-risking, taking the biggest pieces first. So, like day-one is all about mindset, and philosophy, and I go through this visualization exercise where you have to embed that resolve of what is that vision, why do you want to do this? Really get that firmly embedded because that’s the thing that’s going to carry you through the inevitable heartaches that are going to appear during the way.

Matt: One hundred percent.

Sean: So, but yeah, day-two is exactly what you said: the employer – what are the biggest obstacles? It’s the financial situation: you’ve got to have some funding source, and for most people, that’s going to be a job or some form of passive income; so how do you get that in place? And how do you have that conversation with your employer if you have a current job? And then the other thing that holds people back that I think is a big obstacle is just like what’s the lease situation, or if I own a home, how do I resolve that? So, we tackle those the second day. And then from there, it’s just literally de-risking pieces of it.

Matt: So, anybody that’s in any situation—even if they have a W2 income job or whatever else going on—you actually talk to them about how you can negotiate with your employer to do your job remotely, or how you can do something that’s included in the Nomad Prep Academy?

Sean: Yep.

Matt: That’s amazing. I think that’s really important. And people that listen to this podcast will know that it’s not only entrepreneurs, or business owners, or people that have passive income that I’m interviewing; I mean, people like you, for example, you actually have a full-time position at a company, and you’re a senior level director of the sales department of a major company that services Fortune 500 clients. And yet, you have been able to negotiate a remote work location, and execute your deliverables—and actually even execute them at a higher level—while traveling the world, and living on the beach in Brazil, or hanging out at bowling alleys in Morocco, or whatever it is.

And so, even if people are at a very high senior executive level like you are, there are ways to negotiate with your employer to work remotely, and even to show increased results while working from another continent!

Sean: Yeah. Yeah, anything is doable; I think it’s all about risk mitigation. Take the perspective of your employer, and think: what could I do, how could I frame this as an experiment that would make them feel comfortable; how do we wade into this scenario; what’s the minimum viable product that I could produce working remotely one day a week to start, and produce a result, and gain their trust? And now, okay, I want to go remote a couple times a month, whatever; earn your right to do this, and then at that point, you’re building that trust.

Matt: I agree 100 percent with that. And it’s interesting because I believe that people—and a lot of people that I have conversations with, right?—if they’re not into this lifestyle, a lot of people will try to come with objectives first, “Oh, I couldn’t do that because – ” and a list of reasons why they couldn’t do it.

But in reality—as you and I know from being in these nomad circles—the people that we hang out with, either the people – I mean, we’re here in Brazil with literally, there’s probably 40 digital nomads from all over the world that are actually here with us now that we’re hanging out with, and having barbecues with, and going to these clubs with, and drinking caipirinhas with, and these people are from all over the world! And these people are a combination of: some of them are entrepreneur business owners; some of them are investors living off passive income; some of them are freelancers, and some of them are full-time salaried employees.

So, whatever situation you are in, there is a path. And there are people that have done it from your situation. And so, if you want to do it, there is a way, and I think that’s awesome that your Nomad Prep Academy addresses that, and addresses different situations, and helps people to understand how to negotiate that, and how to begin talking about that process.

Sean: Yeah—I wish I could remember the quote, and I won’t—but it’s by Saint Antoine Exupéry, he’s saying like: if you’re trying to build a ship, you’re not going to go out and try to teach people the process of shipbuilding; if you want to do anything, the single most valuable thing you can do is teach them to long for being on the sea, right? Embed that resolve. And so, I think that’s – get that clear in your head first of all, and in your heart, and once you have that the other pieces will find a way to fall in place.

Matt: I agree with that entirely! If your drive is strong enough, you will figure out a way. And because you’re going to change your excuses – see, here’s the thing: I think that people will either make excuses which are self-justifications for maintaining their current position, which is the definition of an excuse, in my opinion, right? And basically, you’re trying to self-rationalize why you are in your current position and why you can’t do what those guys in the podcast I heard about are doing, right? Or you’re going to say, “This is –” the same thing that’s on person A’s excuse list, on person B is going to say, “This is my obstacle that I have in front of me.”

I identify it as an obstacle, i.e., my employer will not currently let me work remotely, right? And then, they’re going to say, “How can I potentially begin overcoming that obstacle?” And those are two totally different frameworks.

Sean: Yeah, just by framing it in that way, “What might I be able to do that could change this equation?” Frame it that way, and that is a fundamentally different approach to saying, “These are the reasons why I can’t do it.”

Matt: Exactly, exactly. And so, if you are in that mindset, and that is what you want to do—you want to achieve that, you want to have that lifestyle, you want to do that—there is a path from every single position. It doesn’t matter if you’re a salaried employee, or a freelancer, or an entrepreneur, or anything else, there are people in every single category that are literally here with us right now in Brazil that have done that. So, there is a path.

But then, beyond that—assuming somebody has actually established a location-independent income stream, right?—there’s a big difference between being location-independent, and being a digital nomad, right? I’ve been location-independent for 11 years; I just chose to spend my first six years of location independence in Los Angeles, California because I love LA. I had no business purpose there. I had no geographical restriction confining me there. I just loved LA. And then, five-and-a-half years ago, I decided to start traveling the world and becoming a digital nomad, becoming an itinerant world traveler, and those are two different life choices.

So, there’s a difference between location independence and digital nomadism, so for people that have established that location independence income stream, meaning they can quote/unquote “work from home,” but they can also work from Brazil or Thailand, if you can work from home. So, for people then to say, “Okay, I got my income straight,” the Nomad Prep Academy is then also going to be able to tell them how to prepare to travel the world, is that right?

Sean: Yeah, so it is applicable to anyone who wants to do this, regardless of how they want to do it. If they want to do it with a travel program or go via solo travel like you did, it’s making the assumption that if it’s your first time, you’re likely – the way to easily wade into this pretty confidently is through a travel program; so, it makes that assumption that you’re going to go with one of those. But it’s agnostic—actually, on day-one we help you choose whatever travel program is the most beneficial given your circumstances.

Matt: Awesome, man! And then, tell us a little bit about the Nomad Podcast.

Sean: I think, we both enjoy interviewing nomads because they’re amazing, inherently interesting people. And so, I would do it – it’s the thing I would do every day – if money were no object I would just be doing Nomad Podcasts, interviewing people right and left.

Matt: Yeah, and you’re getting very high-caliber guests. I mean, you’re getting founders of a lot of the top nomad work-travel programs, and full-time digital nomads that are doing really interesting stuff, and have been for many years; I mean, you’re getting really premium quality guests. And I think that you’re asking and you’re talking about very cutting-edge travel issues—I, of course, subscribe to the Nomad Podcast, I think I’ve listened to every episode so far.

But it’s really high-level conversation with people that are – if you want to call them influencers, or if you want to call them – whatever you want to describe them as, they are people that are certainly on the forefront of developing business solutions, lifestyle solutions, and really forward-thinking people that are deeply engaged in this lifestyle, and thinking about developing solutions for other people to engage in this lifestyle, and really building a movement of sorts, you might say.

Sean: Yeah, I break it down into three categories. I wanted to interview nomads—so full-time nomads like yourself—founders: product founders, program founders, and then domain experts. And the domains that I focus on are things that I really think can help nomads; so things like – the last guy I think I had was a business coach that helps you figure out that “What could I build?” in terms of a passive recurring, sustaining income. But like sleep experts, self-defense experts, nutritionists, all the things that I think can teach us – all the people – the experts that can teach us things that are very useful to nomads on the road.

Matt: Yeah, that’s awesome. So, we’re going to link up to all of this stuff, everything we’ve talked about we’re going to link in the Show Notes; just go to TheMaverickShow.com and go to the Show Notes for this episode, we’re going to have the link to the Nomad Podcast, the Nomad Prep Academy, if you’re interested in that we’re going to link to all the Pagely stuff that we talked about, so you can actually see the sale systems that Sean has developed, and actually go through the Choose Your Own Adventure video, and just see what they’re doing, and see what elements of that might be applicable to you, and to your business. So, all that stuff is going to be in the Show Notes.

Sean, so at this point, are you ready for some Lightning Round questions?

Sean: Man, I am so ready, but only if I can do the sound effect for it!

Matt: Hit it, man!

Sean: [Imitates lightning striking] The Lightning Round!

Matt: Okay, now see if that sounds like the actual Lightning Round effect, which we’re going to drop in right here.

Male Announcer: [Lightning striking] The Lightning Round! [Thunder rolling]

Matt: What is one book that you would recommend that has really influenced you over the years?

Sean: I mean, so business book, I think it’s got to be: Steve Blank, Four Steps to the Epiphany; a horribly written book, by the way. It was basically a summary of a bunch of lectures he had given, and it’s just strewn with typos, but incredibly powerful insights and ideas. So, that would be the biggest business book. I would say Ayn Rand, maybe Atlas Shrugged is up there, it’s just a really powerful book; Alchemist was another favorite, so.

Matt: What would be one either blog that you read, podcast that you listen to, a YouTube show that you watch, some type of content medium that you consume that you would highly recommend to other people?

Sean: So, I read Hacker News daily. Contrary to what it sounds like, it’s not all like geek hacker stuff, but it’s just a super interesting – it’s Paul Graham, the founder of the Y Combinator, incubator. He built essentially a news aggregator like a Reddit site, but it tends to focus on kind of the programmer types. But it’s super-interesting – it’s not the boring news, or the depressing news, it’s all kind of the positive advancement, cool stuff going on.

Matt: Cool. What is one app, or productivity tool, or gadget that you’re currently using that you’d recommend?

Sean: I have to say the TRX stuff has been really useful, so I use that TRX Suspension Trainer. It’s what I do in place of going to a gym in every city that I’m in; I just use that, and it’s phenomenal.

Matt: Can you explain how it works?

Sean: Yeah, so actually, I had met the founder of it, Randy Hetrick, was a Navy SEAL who created this device. They trained, and I believe the backstory is they were – this elite unit of Navy SEALs that had to live in shipping containers in China, and they had to be ready on a moment’s notice to go and deal with like a hijacked boat scenario, but they were literally living in shipping containers, so very confined spaces. This was what he created to be able to stay in shape in that scenario, and that’s an extreme use of it.

But like for a nomad, it folds down to something the size of maybe a softball. But you can string it up on a doorframe, on a tree, whatever, and it provides a full body workout: back, thighs, chest, tris, shoulders, abs, legs.

Matt: That’s awesome, man, I love that; I love the minimalist stuff as well. So, okay, let me ask you this: what are your top three travel destinations that you’ve ever been, that you would most recommend other people visit, or you’d most like to go back to?

Sean: Galapagos was up there. I mean, it’s just incredible; you’ve been, it’s a good one. Galapagos, I would say Machu Picchu had to be probably my top thing that we did on Remote Year, it’s mind-blowing to me. It blows my mind that more people aren’t blown away by it, how is everyone not just going like, “Holy crap, we have to go visit this because how is this even here?” So, just a surreal place, and it lived up to its expectation, I was very excited to go there, and in person it’s just as amazing; so, definitely do that. Third one – man, that I would return to?

Matt: Or that you’d most recommend that other people do. I mean, even if it was a once-in-a-lifetime/bucket-list thing, you know? What do you – what sticks in your mind as a really influential, or inspiring, or amazing place that you’ve been?

Sean: We did a side trip – when we were in Valencia, three of us went to Ireland, and we drove across country. And we – there was just this really powerful moment where we got to the Cliffs of Moher, and it’s all mixed-in with nomading; I then realized I had to do a call, so I raced back and closed a sale in a hailstorm on a laptop tethered in the vehicle, and it was just like all this crazy. But standing there on the Cliffs of Moher just pre-hailstorm, it was a really magical moment.

Matt: That’s awesome. And you and I, of course, are both Irish-Americans, and I have spent a good bit of time, as you know, in Ireland as well: I went to Trinity College in Dublin for a year, and have been back to Ireland a number of times, so definitely a very, very special and magical place on many levels. For people that haven’t been to Ireland, for sure. Okay, so what are your top three bucket list destinations that you’ve never been, that are the highest on your list right now, that you would love to see?

Sean: Yeah, so I have never been to Asia, actually. Of all the places I’ve been, I’ve never been to that part of the world, so I really want to make it over there. Sometime in the next year, I’d like to go around Southeast Asia, and while I’m there then do Australia and New Zealand; so, that’s got to be No. 1. I’ve never been to Iceland, that’s high up on the list. My buddy, Chris, who I traveled with recently did a trip there, and he’s just a brilliant photographer/videographer, and so seeing his photos, I feel like that’s got to be on the list.

And then, a third destination – man, can I go back to one of the places I’ve been to? And it’s even in the US, so it’s not even that exotic, but the Grand Canyon. We did a backpacking trip to the bottom of the Grand Canyon, and that was just – just so epic. So, that probably would be my third to go back there.

Matt: Yeah, Grand Canyon is frigging insane. I mean, it’s just totally nuts, I agree! I went there for the first time, I don’t know, five years ago? That’s the only time I’ve ever been there, and it was just like, “What is this place?” There’s a lot of amazing places, as we travel the world it’s interesting because sometimes we put so much emphasis on the international travel, but then all of a sudden, there are so many insanely epic places in the United States also that are just like totally nuts, so that’s a good reminder and a good thing.

Sean: Yeah, and scratching-off a bucket list item doesn’t preclude it from being a future bucket list item again. I feel like it was that epic where I would absolutely go back to the Grand Canyon.

Matt: Or doing something different there, doing it a different way, right? I didn’t go all the way down to the bottom or do the rafting trip through the river, I went and did certain things there. But you could go back and do other things there, which is how I feel like I leave a lot of cities.

I’ll go and stay – even if I stay in a city for four or five weeks, a lot of times I don’t – sometimes I tell myself —and I don’t know if it’s intentionally, or like if I just kind of got too busy or lazy to do everything—but I kind of like leave cities with major things that I actually didn’t do in that city, and that inspires me to go back. Because like, “Oh, yeah, I still have to go and do that,” and so, I want to return and have a new experience doing something else in that city, you know?

Sean: I have a feeling this won’t be the last time either one of us comes back to Brazil, this is just amazing!

Matt: Goodness me! Goodness, gracious! Yeah, it’s magical every time I come, and I have the 10-year visa, so I’m allowed to come for 180 days a year for I think seven more years, so I’m sure we’ll both be back. Awesome! So, Sean, tell people how they can get in touch with you, how they can follow you on social media. We are going to put in the Show Notes at TheMaverickShow.com, all of the links to everything that we’ve mentioned, including all of your recommendations from the Lightning Round, and all of your Nomad Academy and everything else. But if people want to connect with you, follow you on social media, how do they find you?

Sean: Yeah, so I’m Scrollin On Dubs on most social media, which you’ll appreciate I know with a hip hop background. But Scrollin—no “g”—Scrollin’ On Dubs, and I’m just not even going to attempt to explain that handle.

Matt: That’s just an amazing handle. One of our mutual friends, she was like, “What’s Sean’s Instagram handle?” I’m like, “@Scrollinondubs,” she was like, “No, it’s not,” I was like, “Oh, but it is.” Which actually – wait a minute, that reminds me! I have to do one more Lightning Round question with you that I forgot!

Sean: Okay.

Matt: There are a select group of people that I interview that I have one very special question for, which is to name your top five hip hop artists of all time. And you are somebody that has a very diverse music background, appreciation for a lot of diverse types of music, but one of them is hip hop.

Sean: Yeah.

Matt: And so, I want to ask you as the final sort of question here, @Scrollinondubs, to name your top – and we’re going to go out with your naming your top hip hop – top five hip hop artists of all time.

Sean: All right, so I would put Eminem up at the top; Dr. Dre, obviously up at the top; Ludacris, big fan; probably Ice Cube, and then – I don’t even know if this qualifies, but Beastie Boys, old school Beastie Boys I think.

Matt: They definitely qualify, man. They definitely qualify, yeah. And that’s actually a really diverse group of five because you’ve got East Coast, you’ve got West Coast, and you’ve even got the South, man, so you’re spread all over; you’re diversified! I love it, brother, those are great choices! So, Sean Tierney, @Scrollinondubs on Instagram, we’re going to put all his stuff in the Show Notes, be sure to check that out. Thank you so much for being here, brother, this was a really special interview.

Sean: It’s been awesome, man. Safe travels.
Matt: All right, good night, everybody!

Male Announcer: Be sure to visit the Show Notes page at TheMaverickShow.com for direct links to all the books, people, and resources mentioned in this episode. You’ll find all that and much more at TheMaverickShow.com.

Would you like to get Maverick Investor Groups White Paper on real estate investing for digital nomads? How to buy US rental properties from anywhere in the world, and finance an epic international lifestyle? Just go to TheMaverickShow.com/nomad. The report is totally free, and available for you now at the TheMaverickShow.com/nomad.

Female Announcer: Do you want to learn how to travel the world for a year-plus with carry-on luggage only, and look good while you’re doing it? Go to the TheMaverickShow.com/packing to see a free recorded webinar and learn exactly how Mad does it. He shows you the luggage he uses; the specific items he packs, and the travel brands he likes most. Even if you’re just looking to go on shorter trips but pack more efficiently, and eliminate your checked luggage, you won’t want to miss this! You can watch the free recorded webinar at TheMaverickShow.com/packing.

[End of Audio]

Duration: 105 minutes