Matt Bowles: Hey everybody, it’s Matt Bowles, welcome to The Maverick Show! My guest today is Sean Tierney, he’s back on the show. If you missed the first episode with Sean, it was episode No. 21, you’re definitely going to want to check that one out. But we have a whole bunch of new and amazing stuff to talk about today. If you did not meet Sean yet, he, first of all, has over 10 years of entrepreneurial experience. He is currently 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. 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% 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 combined, Sean’s sales expertise has helped Pagely grow from an eight-employee company, to a 38-employee company, and he has subsequently gotten international media attention and speaking engagements around the world for the sale systems and processes he has built at Pagely. Now, Sean is also the founder of Charity Makeover, he is the host of the Nomad Podcast, and he is the founder of Nomad Prep Academy, an online training course to help more people transition into the nomadic lifestyle. Sean, welcome back to the show, my man!

Sean Tierney: Dude, I just want to quit right now, that’s like the most amazing intro. I just feel like I can drop the mic and just be like – accept the Grammy Award and go home, and just be done.

Matt: Well, now, you and I – let’s set the scene here: we are actually not in the same city today. The last time that we hung out, we were in Lisbon, Portugal, where you interviewed me for your podcast, Nomad Podcast. And when we were there, we opened a beautiful bottle of Portuguese red wine from the Douro Valley, and it was a really, really amazing experience. And I understand that even though we’re in different cities today—I’m actually in Lagos, Nigeria in West Africa—I understand that you still being Lisbon, have carried-out our tradition and that you are literally opening a bottle of Douro Valley wine as we speak.

Sean: Indeed, I’m looking at a bottle of Douro Reserve Vinho Tinto. And Douro, for the people listening, it’s a wine region in the north of Portugal, and I think it’s the best wine. I know you were just in Stellenbosch, and I have a feeling it’s similar in that it’s like 100 of the most premier wineries in Portugal are all in this region. So, that is what I am drinking. What do you have in front of you right now?

Matt: Man, I have a South African red blend that I’ve been drinking here in Nigeria. South Africa is really the preeminent wine region on the continent of Africa, and so, I was just in Cape Town, I was out in Stellenbosch, and doing a bunch of wine tasting out there. So, really, whenever I’m in Africa, I try to get the South African reds because that’s really the preeminent stuff on the continent. So, cheers to you, my man.

Sean: Well, cheers, brother.

Matt: All right. So, let’s also – I should also mention that as you logged-on here, and we put our names into the registration to record this podcast virtually, I looked at your name, and instead of Sean Tierney it says “Sean Diddy Combs,” so that’s who I’m speaking to at the moment, according to my computer. So, I appreciate the Hip Hop references, my man. Anybody that heard the last episode heard you drop your top five Hip Hop artists of all time as the final Lightning Round question, that’s where we left off. So, I guess that’s where we’ll begin again today. So, we’re back on track and continuing right where we left, which I love that. So, let’s open up with – I want to go through a whole bunch of stuff. I mean, you and I have known each other now for over a year. We’ve spent time in a number of different countries, and there’s just so much stuff that I keep learning about you each time we spend time together, and I’m like, “Man, we have to talk about that on another episode of the podcast.” So, I’m super-excited to reintroduce a whole bunch of stuff about you on this episode. And let’s maybe start a little bit back, I want to kind of go through your entrepreneurial background. And just to start way back, I mean, last time we talked a lot about the sales stuff that you’ve done at Pageley. But prior to coming to Pagely, I know that you were an entrepreneur and that you had those tendencies from a very early age. So, can you kind of talk about where you grew up, and how those tendencies came to fruition?

Sean: Yeah, for sure. So, I grew up in Phoenix, Arizona, and I think the first entrepreneurial thing I ever did, I was in eighth grade and I just got this harebrained idea that I was going to produce VHS—because VHS was the tape back then—but I was going to make VHS tapes of the school plays and sell those to parents. And so, what I did was: I took my parents’ fax machine—and you’ll probably remember, this dates us, but thermal paper, that really crappy paper—I printed up a bunch of these flyers on their fax machine, and then, inserted them in the pamphlets of the folks at the school play. And I just kind of rouge went in and “flyered” the whole placed, and said, “$10.00 for a copy of your son or daughter performing,” and had 100 orders come in and made 1,000 bucks, because I had no costs, my parents were buying the tapes. I basically, went to a bunch of neighbors’ houses and got the VCRs from them, and then, figured out how to chain them together so I could produce these things; instead of one-at-a-time, I could five-at-a-time. And so, yeah, so I made 1,000 bucks as an eighth-grader, which was a huge chunk of money, and I was like, “Wow, this is really cool.” So, I think that was really like the first entrepreneurial venture I ever did.

Matt: That’s unbelievable, $1,000.00 in eighth grade. I mean, that must have been very inspiring that you successfully executed that. And then, from there, what were your next sort of entrepreneurial moves as you grew up from there?

Sean: Yeah, I mean, I would love to say that I started the next big thing after that, but I think I went – just did school, went through high school, got into music and guitar, I didn’t really do much entrepreneurial in high school. But I did with my brother, shortly out of college, our next entrepreneurial thing: we started a business – I had been running this thing called Pub Crawl, so back-up. So, we would throw Pub Crawls and I was technical—I was at that point a computer programmer—so built a site that enabled us to publicize this and throw pub crawls. And then, figured out if I could add one more column to the database, we could make it so anyone could use this system to promote and execute pub crawls. And so, we built this thing called pubcrawl.net, and it grew to have something like 120 different cities that were using it to through pub crawls. And so, it kind of inadvertently became like this meetup.com of throwing pub crawls. Anyway, long story short: we did a number of these and each time I was just renting a 40-passenger bus, and then, selling tickets and doing it that way. And we came to the determination that – we started doing these monthly, it was better if we just bought a bus and it would ultimately be cheaper. And then, during the week we could rent it out for bachelorette parties and stuff. So, we ended up buying a city bus, gutting it, putting in pseudo marble floors, and leather seats, and plush curtains. We did like networked X-boxes—and we hacked the X-boxes, so they had like every game on it—and we made this ridiculously cool thing; I think I’ve still got some photos, maybe you can link them in the show notes. But we built this insanely cool thing, and learned a lot about it as the transmission dropped in the week that we got it, so we ended up having a lot of money that we had to spend there, and then X-boxes got stolen on the second ride. So, there was a lot of lessons. It was very glamourous from the outset, and we learned that driving drunk people around at all hours of the night is actually like really annoying. But yeah, that was the next entrepreneurial adventure.

Matt: That’s a significant lesson, though: driving drunk people around at all hours of the night can be annoying. And so, you were in – so you were in Phoenix at the time. And then, I know that you got involved with the Lean Startup Group in Phoenix and that you were involved in that as you were going through some of your other entrepreneurial experiences. Can you talk a little bit about what that is—the Lean Startup concept—and what you were doing there? And then, some of your other entrepreneurial endeavors that came out later?

Sean: Yeah, absolutely. So, about that time, I was starting my first products company called JumpBox. And the Lean Startup Circle for the people listening, this is a global thing. A guy named Eric Ries came out with a book called The Lean Startup, it’s not actually the first – I have to give homage to the original founder, Steve Blank is the godfather of all this stuff. So, go read his stuff, he’s the one who really is the person behind this. But Eric Ries is almost like the apprentice who got famous, or he’s the protégé that got famous, and the master didn’t get the credit that he deserves. So, Steve Blank is the guy. But anyway, Lean Startup Circle is this global network of these meetups, and it’s all around this methodology for doing startups. And so, I became a practitioner of this and started the first group in Phoenix, the Lean Startup Circle for Phoenix. And what this was was basically like a support group for people that were trying to actuate these ideas in pursuit of their own startup. And so, I ran that for three years while I was building JumpBox, and we helped a number of entrepreneurs who were going through similar challenges apply these concepts. 

Matt: Awesome. And then from there, can you talk a little bit about JumpBox and what that was, and how you built that company?

Sean: Mm-hmm. Yeah, so JumpBox, the way that emerged: I had been – at the time I was a consultant, so I was doing freelance work, I was building commerce applications. Somehow, I had this career where I was a computer programmer of eight years, and I don’t know how I did it. I’m the worst programmer in the world, and yet, somehow I made that my living for eight years. I had no formal CS training, I just kind of learned it and went down this interesting rabbit hole of getting into that position. But anyway, I was a freelance consultant. Through a number of lunch conversations—I was sharing office space with another guy who was a freelance consultant, and he was a way better programmer than I was—and so, over those lunch conversations, we came up with this idea, we tried something called Grid 7. It was a co-op concept where we would help – we’d have other experts all come together on the weekend, and the idea was that we would build these passive recurring revenue projects on the weekend, and it would allow us to all quit our day jobs, and eventually, this would be the thing. That failed, but during the course of that endeavor, one idea that was just too big for that format that we had was this concept called JumpBox. And we ended up building what became a whole space called Virtual Appliances. So, we came up with a radically different approach to distributing software. If you think about normally how software is distributed, it’s an installer that people install the application on their computer and set it up that way. Well, we figured out a way using virtualization that you don’t even need to do that, you can ship a mini-virtual computer with everything already set up on it, and it runs in the context of your computer. And so, people’s eyes may be glazing over right now what this is, but essentially, this became a tool for server admins. We got every major Ivy League school; every branch of the US Military was using it; we had customers in 40 countries around the world using it. It became a big deal, and we really created a whole space in computing. We ended up not winning that space, but we were the first people really doing it.

Matt: And you raised a significant amount of money for it, as well, I understand. Can you talk a little bit about how that evolved, and then, ultimately, what happened, why did you transition out of that?

Sean: Yeah, so we raised – well, I don’t know, “significant” by whose standards? We raised $750,000.00, I just raised from friends and family initially, and then, got into The Angel Network. We found a vein of hockey players that ended up investing. And I had initially taken out a home equity line on my house to fund the company at the beginning. And then, just started raising money, and eventually, we had revenue as well. So, we got to an interesting cul-de-sac where we were meeting – I basically drove my truck up to San Francisco, couch-surfed for a month, ended up having no connections when I got there, and by the end of the month, I had met with 14 venture capitalists. And so, it was like an eye-opener into really how connected that city is. If you just go and network, and go to all the events, and kind of share your vision, and get out there, you can really in pretty short order embed yourself in that community and get to – there’s a ton of money in that area, and they’re just looking for good ideas. So, we had some luck there. I had a verbal go-ahead with Sequoia, but it fell during a really crappy timing during 2008, September, when the Lehman Brothers – just the whole financial crisis happened. And so, we had the go-ahead from them, we didn’t have a terms sheet, but we had the verbal go-ahead to work with them, and they were like a top-tier.  Arguably, Sequoia is one of THE top-tier investors. So, we had the go-ahead; unfortunately, the timing was really bad, so the door slammed shut on the capital markets. We had to basically get profitable. At that time we had a $50,000.00-a-month run rate, and like 11 employees, and so, it was painful, we had to lay some people off. Fortunately, the revenue was increasing at that point, and so, we did turn the corner on the runway that we had left, maybe like three months of cash in the bank at that point given that run rate. Anyway, we managed to extend it, turn the corner. It never broke out; it became what they call a “zombie company” in that people fund a startup because they think it’s the next unicorn and they’re going to make a crap-ton of money on it. We built what was more accurately a lifestyle business that was in a very interesting space, and albeit we did some really cool stuff, but it was a lifestyle business ultimately. And so, we eventually made the decision to shut it down. We had a lot of code debt, and we had obviously the convertible notes and the investor debt, we basically ended up just giving them back the money we had in the bank and [inaudible] [00:15:34].

Matt: And I know you also got into the real estate space for a little bit, which I was really interested to hear about, we have a lot of real estate people that listen to the show. Can you talk a little bit about how that came about and what you were doing with real estate for a little bit?

Sean: Yeah, I mean, that 2008 period, I was living in Phoenix at the time, I had a house in Phoenix. And Phoenix was, I believe, the second city that was hit the worst by the real estate crisis. And I know you’re intimately familiar because that’s when you were starting your real estate firm at that time, as well. So, you know about it. I had a house; I had taken out the home equity line to start the company; I wasn’t paying myself; I was paying my employees. And so, it was a particularly difficult time, and the house was well under water given that I took out a second mortgage to do the company. So, I was looking at just walking away and leaving the keys, and going through the foreclosure process at that point. And a friend of mine heard about that; he said, “No, you really should short sell it, and here’s why.” Long story short, I ended up short selling the house successfully with the help of a friend-of-a-friend. And he was so good at navigating the process, and this was like such an eye-opener to me, I didn’t realize that this whole concept of a short sale existed and that you could purge the debt and all that. And so, it was amazing, and I decided – I said, “Look, a lot of people are going through this right now, you’re really good at navigating it, why don’t we team up and we’ll take your knowledge of the short sale process, my knowledge of legion and technology, and we can do a startup around basically helping other people, introducing them to this option, and assisting with their short sale. And we ended up building that, we did something called “Shortsaleopedia,” it was the largest question-and-answer site—and that’s a whole other story of how we growth-hacked that—but we had – for a while, we were No. 4 for the term “short sale” on Google. But anyway, we ended up building up this massive system, and we made a network of – across the US, I think we had 150 total realtors in it. And we would just basically originate leads, and get people who had questions and who need help with short sales, and then, we formed relationships with the best CSR-designated realtors in each location. And we would pair them up and make the referral, and then make referral commission on that arrangement.

Matt: Awesome! Let me ask you now about this. I know you also got into and during this time you were doing things with art, and you were also doing things with music. And some of that overlapped with business, and some of it just was creative, and personal, and stuff like that. But can you talk a little bit about both the art side for you and the music side for you? And I’ve noticed on Instagram recently, for example, you’re doing some really interesting projects with some of the past things that you’ve been involved with and stuff like that. So, can you share a little bit about that and what that’s meant to you?

Sean: Yeah, for sure. So, we have music and art in our family, from my dad’s side: my aunt is a really skilled watercolor artist; my grandfather was both a sketch artist and a very talented piano player. So, that gene comes from my father’s side of the family, and I’ve had art and music in me since a very young age. So, yeah, the experiment that Matt’s referring to, I have a thing going right now just for the heck of it: for seven days I am pairing an original painting with an original piece of music, and I’m pushing that out through Instagram and Facebook, and then, I’m telling the story behind the music and the art. And it’s just kind of an experiment more than anything right now to see if we can do something more interesting with Instagram than travel photos and soundbites. But business-wise, I tried to meld those back in – God, I don’t even know what year that was, but I went and – I wanted to live by the ocean, and so I went and moved to Newport Beach. And a buddy there talked me into working with him in Laguna Beach, which has a huge artist scene. And so, we decided to try and take my knowledge of computers and marketing automation, and see if we could help artists sell their works, and just really scale – growth hack the sales of original works for artists in Laguna Beach. And so, we started that company, it was called Artilidge, it was a very short-lived project. What we learned, we met with – God, we screened about 100 artists, we met with 15 of them, we boiled that down to three, and the goal there was to help them basically figure out: what can we apply of our knowledge to help them sell their paintings? But what we learned pretty quickly, working with artists is the lack—at least the ones we found, and these were the best of the best that we could find—there’s a reason they’re starving artists, they kind of embrace that role and almost cherish that vision of being a starving artists, versus wanting to just go out and crush it. And we found it very hard to get them to actually contribute content, and stay on top of it, and just be – you know, hustle. So, anyway, we pulled the plug on that business about a month after going through this whole screening process. I was still in Newport, I had a lease, and so I was like, “What else can I do?” I went through this Simon Sinek “Start With Why” program, which I love, it was really powerful. And that led me to another project that I started that was called “Survival School TV,” and what that was – this is just a radically different business than the art stuff. So, Simon Sinek, you have the Start With Why process, you learn about what your “why” is, and then, basically, you want to envision: what is the most ambitious thing that you can contribute to the world? And I started thinking like: if my task was to eliminate crime and disaster from the world, if that was what I was charged with, how might I go about trying to attack that? And the thought was: you can’t secure all the targets, but you can – what if we could implant essentially sky marshals throughout society? So, if you could get half a percent of the population trained-up in things like emergency medical, and self-defense, and weapons knowledge, and just like all the skills of a Jason Bourne, if you had enough of those people scattered throughout society, that’s how you mitigate issues like terrorism, and disasters, and floods, and any tragedy you can think of. If there’s enough of those people in society, then it’s actually going to be very good. It’s going to make the whole society safer. So, we set out to try and make that. Did a pilot with a Krav Maga instructor. And long story short: it’s very difficult to monetize this, it was really more of like an ambitious, well-meaning project, but very ill-conceived revenue model around it. So, that didn’t last long; we were unable to monetize that. I ended up ultimately pulling the plug, heading back to Phoenix, and falling back to what I know, which is the consulting.

Matt: So, all right, I have to ask you one more Phoenix story.

Sean: I know where you’re going with this.

Matt: Which is the story about the license plate. I’m not even going to say anymore, I’m just going to allow you to tell it, and explain the context, and tell this story. But we have – this did get you on the news, and I understand that we actually have a link to the news clip of when this happened, which we’re definitely going to put in the show notes for people to go see. But how old were you, and just set the context, and then you can tell the story.

Sean: Yeah, it was while I was building JumpBox, so I would’ve been about 30 or 31-ish, around that area. Okay, so the one Matt’s referring to: I hate photoradar—I don’t know if you’re listening if you know what that is—but photoradar are these cameras, they put them in our case both on the highway and on red lights in Phoenix. And so, they’re largely billed as being a safety measure, it’s designed to slow people down, and in theory, makes the whole society safer. But there was a bunch of studies that were indicating that no, it was actually people were slamming on the brakes at the red light, just because they were realizing they might get the ticket. Or stopping on the highway, slowing way down because they didn’t want to trip the camera, and it was causing more accidents than it was helping. So anyway, I hate photoradar, I looked at it, and I started thinking: what are the options for defeating photoradar? I went through a number of different things: I know there are sprays, and trick plates, and various things you can do. But then, I got this idea: okay, well how do you actually get the photoradar ticket?  I started thinking about the process of how that works. There’s a camera, and at that point they didn’t have the optical OCR stuff, so there was actually a person that would have to look at the films and pair that up with the license plate, and then issue the ticket, and there you go, that’s how you get the ticket in the mail. So, I said, “Okay, well, I can get a vanity plate, why I don’t get one that has confusingly similar digits and letters? I ordered a vanity plate online for Arizona that was like ODO 00D, or something like that, and I don’t even know what the plate was. But I order this plate; I got it, it was right before I was going on a vacation when it arrived. So, I posted it, I wrote up this blog post called The Vehicular Thomas Crown Affair, and I was promoting this, I’m like, “Hey, anyone can get this, this is how you do it, and this like F*** photoradar, this will defeat it.” I come back from Cabo San Lucas to literally an email Inbox full of all this stuff like the news crew was at our office, that was on a radio show, the newspaper did an article on me. So, it was like my 15 minutes of fame for essentially hacking photoradar, and telling people how to do it. And it pissed-off a lot of people. I’ll give you the blog post that was kind of the seminal piece I did on it. And like half the comments were just scathing people like, “Oh, I can’t believe you’re telling people how to – just slow down, don’t –” whatever, and half the people are like, “Right on! F*** photoradar!” But yeah, that was kind of my claim to fame in terms of defeating that creatively.

Matt: That’s one of the most amazing-looking license plates I’ve ever seen because it’s like three different letters, like O, D, and zero, but they all look basically exactly the same, so you can’t tell what the letters are on the license plate.

Sean: Yes.

Matt: Unbelievable. Well, we’re going to post the link to the news story that actually interviews you when it happened, and it shows the plate and all that kind of stuff. So, we will put all of that in the show notes. So, let me ask you this: throughout your entrepreneurial experiences, can you talk about what were the lessons that you learned from going through all of these different endeavors? And ultimately, when you landed at Pagely, I mean, can you just kind of talk about your reflections on that path and how you decided through all of your experiences that Pagely was the right fit for you?

Sean: Yeah, for sure. I mean, I don’t know, it’s hard to boil 10 years of entrepreneurial experiences into concise statements. But I think overall, if I had to do it, I think adopting a mindset of experimentation, it kind of all boils down to that. And our mistake with JumpBox: we built an amazing product, but it took us a year to build it, and then it took us probably another year to figure out how to sell it. And so, if I had it to do over again, I would really recommend validating demand and validating the method by which you’re going to sell the thing before you build it. Or at the very least, in parallel while you’re building it, you should not wait until it’s done to learn those lessons, you should try to parallelize that. But yeah, overall, if I had to collapse it all down to one bit of advice, it would be that mindset of experimentation, figure out everything is an experiment, minute-to-minute. And if you can get good at that, and decide what is the key thing we’re trying to solve for right now? What is our biggest bottleneck, and what does that look like? And so, what question are we trying to answer? What data would we need to have in order to answer that question? And then, what experiment do we need to run to yield that data? And then, you basically back your way into: okay, so this is the experiment, and this is what it’s going to produce, and then we’ll be able to answer that question. And then, do that: run the experiment, get the data, answer the question, and then, rinse and repeat. And it’s literally just a series of that.

Matt: Right, you know, I think one of the things that is really interesting about your story is that with Pagely right now, you’re not – you were not one of the founders of the company, and you’re not the CEO of the company, you’re the Sales Director. And I feel like that’s really, really interesting because you have this entrepreneurial background. I feel like a lot of people feel that in order to get the autonomy that I need, or to travel, or to do my own thing, or to have the  level of freedom that I want, the control that I want to have to become an entrepreneur, and I have to start and found my company, and then I have to run it. And then I think a lot of people get intimidated by that a little bit, you know, with, “Oh, well, maybe I’m not an entrepreneur, or I’m not a CEO, or I’m not a whatever,” and so forth. So, I’m wondering if you have just reflections that you can share from someone that does have entrepreneurial tendencies and has that experience, but has chosen a role in a place that’s not a founder/CEO type of role, can you share thoughts on that?

Sean: Yeah, absolutely. I think I get the best of both worlds. I mean, I’ve heard this term “intrapreneur” that is thrown around now, and realistically, that’s kind of how I operate at Pagely. I don’t have any oversight. I mean, I answer to the CEO, but he basically says, “Keep doing what you’re doing.” So, I run experiments, I figure out what works, what doesn’t work, and then I support our sales team. And so, I feel like I get to act much like an entrepreneur does, only in a safer environment in that I’m – I get a steady paycheck, and I do have performance incentives, I get commission based on how well we’re doing. But overall, I have a team behind me; I don’t have to worry about the overhead, the HR issues, the crap that you go through in running a company, that’s just not fun. I get to really do what I’m best at, which is figuring out the sales and marketing stuff. So, it’s absolutely an option. I think that’s a really good insight that you don’t throw the baby out with the bathwater, don’t think that you have to be an entrepreneur, and take all that risk on yourself, and it’s a binary option. It’s not. There are other ways to have the freedom and to work for a remote-friendly company in an entrepreneurial capacity, and kind of have your cake and eat it too. So, I think that’s a really good insight.

Matt: Yeah, because you’ve been able to do a lot of very innovative and ingenuitive stuff at Pagely. Can you talk a little bit about the Leviathan system that you developed at Pagely, and what some of the lessons are that you’ve learned from that? 

Sean: Yeah, definitely. I did two years as a marketing automation consultant, so I got to know a system called Infusionsoft really well. I’m not actually a fan of that product; I’ve since become a fan of this other thing called ActiveCampaign. But long story short, I learned quite a bit about marketing automation, I was able to apply a lot of my experience as a programmer to do it in a little bit more elegant way; and so, this turned some heads at this ActiveCampaign company. I built something while on remote year called Leviathan. And I basically, imagined – given that at the time, I was the only salesperson for the company, I was doing a number of roles: I was writing content for the blog; and I was generating the leads; and then setting up the phone calls; playing basically an SDR role as well as the account executive role; doing the calls, and then babysitting the proposals, and yada, yada, yada. I was doing a lot. So, this Leviathan system, I identified that the biggest bottleneck to my progress was my inability to babysit deals once I had a productive phone call. In other words, we were losing deals with people. I’d have an amazing phone conversation, it was a right fit, it was truly the best thing for them, and then they would go off, and they’d go dark, and end up talking to a second-rate competitor. And they would just go with that person because they were the last person they talked to. So, I was like, “That can’t happen, and yet, I don’t have the capacity, I’m still too busy generating the leads, and doing all the other stuff. So, I need a system that will do that for me. I need to use my knowledge of computers to build something that will essentially be like an intern that I can assign to every prospect in the system, who will watch that person, and see what they need, see what we know about them, what are they doing on our website, how are they interacting with our emails, and just give them really targeted, personalized follow-up.” And so, that’s what I built; I called it Leviathan—every project for Pagely is named after a sea creature for some reason, so Leviathan was the thing, and yeah, it turned some heads. ActiveCampaign ended up getting wind of it, of what I did, I ended up meeting with their chief data scientist and 10 people from their team, and I think it was pretty – actually formative in the recent stuff that they rolled out. But anyway, this is – the whole methodology is pretty sophisticated. I’m going to be doing a webinar on it, I actually made a link for you too, by the way, so if you for Pagely.com/Maverick, I’m doing a webinar on July 9th that kind of unveils all this stuff so you can see how it works. But yeah, lots of lessons there, I think the one that might be most relevant to your listeners—because it’s applicable in other contexts, not just this programming context—but basically, if you ever get writer’s block or what I call “blank canvas syndrome” when you just – you’re starting something that’s kind of a big, massive project, and it’s like that first step is like: where do you even begin? What I learned from this project is if you can take an intermediary step, if you can break it down—in other words, don’t go try to sit down and start programming this thing. If you go one step before that to just pen and paper if you have to, but whatever conceptual sketch, if you can forget the technology first, just diagram it out on a decision tree. Like: what does this need to do; what does the logic look like; and think of it independent of the technology first; and then, once you have that blueprint, it’s far easier to then go and be like, “Okay, what are the constraints of the technology? How do I map this over to that?” Because it’s just too much – it’s too many variables to keep in your head at once if you try to jump straight to implementing in the tech.

Matt: That’s awesome. Let me ask you a very, very general sales question, which is: what do you feel, and with all of the years of sales experience you have in all these different capacities, what do you feel is really the key to closing a sale and to being an effective salesperson if you were kind of to distill that down? And also, feel free to break it out, if there is a distinction between B-to-C sales— where you’re selling to individual consumers—versus B-to-B sales which is what you’re doing now when you’re selling and closing Fortune 500 companies.

Sean: Yeah, I mean, the distinction, I think, is just one of sale cycles, and number of stakeholders, and complexity of the sale. I don’t think fundamentally – like to me, the best way – and our motto at Pagely and our philosophy of sales is that “sales is simply customer service before they’re a customer.” And I’ll say it again because this is literally – our core philosophy comes down to this one statement: sales is customer service before they’re a customer. If you think in those terms, then all you’re doing is trying to get them the best outcome based on what you know of their situation. That then dictates that you do a lot more discovery, that you try to get on the same side of the table and truly understand their challenges, that you have a deep knowledge of your own product and can map that effectively – bridge-build so you can help understand their challenges, and then show how your stuff maps to what they need. And yeah, as long as you – I’ve had plenty of calls where we weren’t the best fit, and I’ll be the first one to say, “Look, based on what I know of your situation, I don’t even think we’re good for you. I think you should go talk to this competitor, and here’s why,” and people will respect that so much. And we’ve had referrals come from those folks because we treated them so well, and they love the fact that we were very forthcoming and saying, “Hey, we’re not the best fit, go talk to them,” but they’ll still tell other people about us. So, I think that’s just – it all comes down to truly try to have fiduciary—the real estate term—but try to have their best interests ahead of your own, and get them a good outcome.

Matt: That’s awesome. Now, I know that you have been – in traveling the world and traveling to some epic locations, you have been losing some sales from some pretty incredible spots. In the last episode, you told the story about how you closed your largest sale of all time from a Moroccan bowling alley—which made it into the title of the episode, by the way, of course. But I know that you’ve had some other epic experiences, you were telling me one about, I think you were in Ireland, what was that story?

Sean: Yeah, so three of us did a side trip to Ireland, a road trip across Ireland, had this amazing trip. Wound up at the Cliffs of Moher, got there just right at sunset, and had this just incredible few moments watching the sun go down, and just like this fog coming up out of the cliffs. And anyway, my phone goes off because, at that point, I was doing all the calls for Pagely, and people could book appointments unbeknownst to me, and I didn’t have a quarantine of like three hours that I did after that. So, someone had booked a call, and there’s like – I looked at my phone, it’s buzzing and it tells me I have 10 minutes to get back to do this sales call. So, I race back; it starts hailing, so I’m running through the hail, get to the car, my laptop’s there—of course we’re far from any Wi-Fi—so I tether-off my phone and get the Zoom meeting up. And I’m doing the call, and it’s just like hailing, and they’re like, “What’s that noise?” I’m like, “Oh, yeah, it’s pretty loud, I know, some construction,” or something like that, and it’s just like pelting this little car. And long story short: had a great sales call, closed it. But how do you explain to someone what that is, you know? Where do you even begin to be like, “Well, it’s this digital nomading thing.”

Matt: That’s amazing. I mean, it’s amazing. When we were on Remote Year, our group, and we were – Remote Year for people that don’t know is a work/travel program for working professionals that are location-independent, and they can work from anywhere. And so, you travel the world together for a year, and you live in a different city each month for 12 months. And so, you get some really interesting and amazing people on the program, and they’re all doing stuff like that, right? I mean, it’s like you’re walking around on like a street art graffiti tour, and people are on conferences calls; they’re trying to close deals on rooftops at midnight, and yet, stepping out to do this and that, and it’s just – it’s amazing. The digital nomad world—whether you’re in sales or whatever it is—is just an amazing work/travel environment that just lends itself to some insane stories.

Sean: It is definitely the period of life when you find yourself saying, “Is this real life?” more than any other time, just the most random things like that happening, for sure.

Matt: For sure. And I know you’ve had a whole bunch of travel adventures over the years. We talked about on the last episode about you falling off South America’s tallest volcano. But I know you also in spending time in South America got certified for paragliding, can you talk a little bit about how that experience went down?

Sean: Yeah, so this is way back in the day. I lived in Quito, Ecuador, for six months as part of an exchange program. And I would walk home from school and see these guys just flying in parachutes, flying for hours off the main mountain, Mt. Pichincha in Quito. And so, I was actually, “Wow, man, I really want to try that,” and so, I got into a class, learned how to paraglide, went to the beach, this little town called Crucita, Ecuador. And ended up – that was like my first extended flight, and ended up flying for like two-and-a-half hours. I was just transfixed, you know, like one of these things where you lose track of time, and you’re just in the zone. And I’m following seagull in Crucita, Ecuador. There was a park there called La Cuchara, “The Spoon.” And so, the winds would come across the ocean, and it hit this point in the mountain where it was like a spoon, it was kind of like – just the way it was structured, it was like a big bowl. And so, it was like an elevator, you could go where the wind was hitting it, and it would reflect the wind up. And so, you kind of just like sit on this elevator, and go up 1,000 feet, and then fly out over the ocean, and come down, and then go back and go up. And so, I’m following the seagulls and just having this incredible experience—and that was Crucita—but my certification jump was like two weeks later. Went back to Quito, and we drive up Pichincha—which is that big, towering mountain that’s like 3,000 feet about Quito, which is already at like 9,500 feet or something. And so, I’m way up there, and it’s the one day we can do this certification jump, and we get there, and it’s fogged-in, there’s fog on the take-off site. And so, you’re not supposed to launch in that scenario; you should never fly when it’s zero disability, but the instructors are like, “Eh, you’ll be fine. Just go ahead, you’ll be fine,” and I’m just like, “Really? Are you sure this is a good idea?” they go, “Yeah, you’ll be fine.” So, I start going down, I’m running down this hill, and because it’s so high – flying at sea level is very different, the air is as dense as it can ever be, at sea level, right? Because you’re at sea level. Up that high, we’re at like whatever, 13,000 feet, I’m having to really run, and I’m running down this hill, and I’m not taking off, and I’m going really fast at this point. But anyway, get off the ground, and it’s a complete whiteout, I’m flying in just a bank of fog, I can see anything, I’m flying for 30 seconds in just a pure whiteout. Pop out over the city of Quito, Ecuador, which is this sprawling city, and it was just surreal. It was one of the moments, again, where you’re just looking at it like, “Is this real life?” like, “What am I doing?” And the guy’s on the radio like, “Esquerda derreche! Derreche!” they’re like, how did I get here? So, I land, and then what was crazy—I didn’t even tell you this before—but what was crazy is I land and the guys from this company Pro Design, which was a paragliding company, they were there – and you’ve got like Red Bull paragliders—these guys doing these wingovers and B-line stalls, and crazy maneuvers—coming in after me, they’re all landing. And one guy, who was a local, he’s coming in, he’s the last one, and you see this guy, he’s way over-shooting the LZ, the landing zone. And so, he’s coming in really high, and we’re like, “What is he doing?” and this guy flies into the freaking power lines and just knocks out the power to that section of the city. Barbecues his glider – this guy could’ve died. He was suspended in air, dangling from the power lines in his paraglider and no one wanted to touch him. He’s begging for someone come cut him down, and of course, nobody wants to – they don’t know if he’s still electrified. And so, the dude lives because – he was suspended, so he didn’t arc the circuit to the ground, so it was actually fine. But what a freaking crazy 30 minutes, right? It was just like, “What just happened?”

Matt: That is unbelievable! And yet, you continued paragliding after that?

Sean: I did for a while. Ultimately, this is a sad story, my instructor in Phoenix died doing it—he died in a flight accident with a student; the student lived, he did not—and I stopped the sport after that. It’s an amazing sport, I hope to do it again someday maybe, but that rattled me. And so, yeah, I ended up – kitesurfing became the thing, it’s a far safer sport, so that’s what I do now.

Matt: Yeah, wow! And we talked about the kitesurfing thing on our last episode when you and I were in Brazil, and we spent a few weeks there, and you brought all your kitesurfing gear, and we talked a little bit about that on the last episode. Now, the other thing that we talked about on the last episode was when we got you in Brazil, in front of an audience, with a guitar, to be able sing a song in Portuguese that you had memorized and prepared. But the thing was that on that last show we did not have a guitar, so I was like, “Um, can you sing a minute of this song acapella?” and you’re like, “Well, the main point is kind of the guitar piece.” And so, for this episode, I had you in advance schedule this at a moment where you could actually have a guitar with you. And I think that the song that I want to ask you to play is the one that you played on the Nomad Cruise—you and I were just on the Nomad Cruise a few months back—which went from the Canary Islands up to Lisbon, Portugal. And on the Nomad Cruise they have a talent show, and you played this song in the talent show. Now, we should also talk about the aftermath –

Sean: No, you played the song!

Matt: So here’s the – all right, so people can’t see us because this is an audio podcast. You and I are both about the same age, we’re both Irish-American guys, and we’re both over 6’5”—I’m about 6’5”, you’re about 6’7”. And so, what happenes was when you have a boat with 200 people on it, apparently, is that when you and I were doing things separately, there was a very high percentage of people that mixed the two of us up, me and you. And so, literally, the night after you played this song, and you got a huge response, and ovation and everything after you played this song.  And the next day, I had people coming up to me all day long and like, “Oh, my gosh, that song you played was so amazing!” And I would kind of laugh and like, “Oh, thanks, but actually, it wasn’t me, that was my man, Sean, who played the song,” and they’d just look at me and be like, “No, it was you, I saw you.”

Sean: Well, Matt, I can’t remember if I told you, but I was at brunch the next morning after your talk, and I’m sitting there, and this woman sits down next to me and starts unloading on her woes about real estate investing. And I can’t figure out why she’s opening up, and she feels so comfortable telling me about this. And then, I’m like, “Oh, you think I’m Matt, don’t you?” and so, it cuts both ways, right?

Matt: Well, and so much so, that you were getting all the feedback on my talks, and I was getting feedback on your talks and the things that you did. The most amazing example of that was: I literally – after the Nomad Cruise when we were in Lisbon, I facilitated a panel discussion for Nomads Giving Back—which is our mutual friend, Tarek, who people know from The Maverick Show, as well, he was a guest. So, Tarek put together this amazing panel, and he asked me to facilitate it, which I did. So, I’m up there in front of the audience for an hour facilitating this panel. At the very end of the panel, there’s an opportunity for people who have charitable opportunities to give a 60-second pitch, and people that are interested in that can come and talk to them. And you got up and gave a 60-second pitch, right? Literally, after that panel, somebody comes up to me—I had been facilitating for an hour—they come up to me and like, “Yo, that 60-second pitch you gave, how can I get involved with that?” It was one of the most amazing things I’ve ever seen; I was like, “This is unbelievable!”

Sean: Yeah, I feel like we’ve got to use this somehow. I think of that movie The Prestige where the twin brothers have the magic show that they can pull off and it seems like they’re disappearing, or whatever. I feel like we have to figure out a way to monetize this.

Matt: Yeah, I mean after a while, I just gave up when people were like, “Oh, that song you sang was so amazing,” I was like, “Oh, thanks very much, that really means a lot to me, I appreciate that,” you know? And I was just not even going to – I was not even going to correct them, I just accept the accolades. And then, I pass an idea, I’m like, “Sean, today four people came up to me and appreciated the song that I played.” But anyway, not that we’ve built that entire thing up, the song actually was legitimately, authentically amazing. And I was wondering if you could play that song for us, including with the guitar. And maybe before you do that, just share a little bit about the context for it, what the song means to you, how it came about, and then, if you could play it for us, that’d be awesome.

Sean: Yeah, for sure. So, the song was actually the very first song I ever wrote; it’s called “Blind.” It was written – gosh, I was river rafting in the Grand Canyon with my brother and my dad, and I had just met this amazing girl in Phoenix, but I was on my way that summer to go to college in Texas. And so, it has a lot of different stuff wrapped-up in one: it was kind of like this theme of rebellion, and how we’re in this gauntlet of education that just leads us to the next schooling, to the next job, to the what after that. And it was kind of that theme, but it was also a theme that I think a lot of Nomads will identify with. Which is when you meet someone amazing, but then, you’re also about to leave that place, and it’s like that kind of bittersweet holy-crap-this-is-so-great-that-I-met-this-person, but this sucks that it’s kind of destined to not work out from the very beginning. So, there’s a lot of those themes, and that’s why I played it on the boat. And yeah, it seemed to resonate with a lot of people, so. But yeah, I’ve got a guitar here, I can give it a shot. All right, yeah, so the name of the song is “Blind.”

[Guitar prelude]

Once in a while the way things happen 

Once in a while things just work out

Once in a while between two people

Once in a while I just wanna shout

Did I ever say love to be with you

Did I ever say love the way you just say anything

Did I ever say I’m gonna miss you when I’m gone

Did I ever say that I believe

I believe that we are blind it seems to me

No one sees things in my own way

And we are blind and choose to be

All the rest just walk away

 

I lay in my bed and lookin’ around

I’m watching the walls they’re falling down

And the only thing left is you and me

And what choice in the voices of authority say

You gotta do well in school if you want a good job

You gotta have a good job if you wanna good life

Fuck the plan, I’ve got my own, and I’m living today

So you will hear me say that they are blind it seems to me

They can’t see the things that we see

And they are blind, and they choose to be

All the rest can just be what the rest will be

 

So where can we go from here 

It’s not much longer now till I’m off to new places and new faces

And you’re just another one in the crowd

But I’ll never forget these times with you

Change the world with all that we do

 

If you could keep one story, one thread, one line 

Listen up as I say it one time

Life is a river, we all live in a boat

It’s got enough, so hold on just sit there and float

Because sometimes in life you gotta battle upstream

Deal with holes in your boat, broken oars, broken dreams 

And I don’t always know how to steer

And I can’t always see, and I don’t always hear

But we take what we get, and forgive what we got 

One try, one life, our shot

And it’s not long now

No, it’s not long now

No, it’s not long

 

That’s it.

Matt: So, awesome, bro! I love that song, man. Thank you for playing that, that was amazing. All right, so now, the other thing that happened on the Nomad Cruise is your initiative of the Charity Makeover I think got revitalized, and in new ways. And I was wondering if you could just talk a little bit about Charity Makeover and what it is, exactly; and how it started; and now what you’ve got planned for 2019?

Sean: Yeah, absolutely. So, Charity Makeover was a project I started back in Phoenix a couple of years ago. I had gone to a really transformational event thrown by a now-friend-of-mine, Andrew Hyde, called Startup Weekend. So, this was – basically, I kind of modeled after what he had built with that, only tweaked it a little bit. Startup Weekend for the people that have never heard of that event, it’s basically, you build a startup in the course of a weekend. So, you have to design and execute and deliver a product in 52 hours from Friday night to Sunday night. And so, I went to one of the very first Startup Weekends ever in San Francisco, and then subsequently, was a part of nine of them: I threw three of them, and I was an attendee at six of them. And so, I was big believer in these, it’s an incredible experience for so many reasons, but the learning, the networking, the exposure to ideas, it’s just an incredible experience. The flaw that I saw with it though is that Startup Weekend, people were inventing these ideas for products and working on them, and then, at the end of the weekend, they would basically get thrown away. And so, you would build something amazing, and then, it would just kind of vaporware after that weekend. And so, I was looking at it like: well, how else could we have this exact same experience, but instead, purpose those efforts towards helping charities? Like, basically pairing up with a charity and building stuff for them, so it actually got used after we left. So, that’s what we did. Like you said, on the cruise, it got revitalized. This is a thing that I had started years ago, and then, it got kind of shelved due to time constraints, and then, I just got the idea to pitch it. There was something essentially like Shark Tank on the boat called Piranha Tank, and I pitched on that. It got a pretty warm response, and so, I said, “Well, now I have to do this.” So, we threw one in Lisbon May 18th—a couple months ago—and it went really well, we helped three charities; it was the first event where we’ve helped more than one. So, we scaled it, and one of those charities was remote; one was a charity that we worked with in Cordoba, Argentina, a monkey sanctuary; the other two were local Lisbon charities, both helping refugees. So we had about 22 members I think participated, and we worked that weekend, and we developed different stuff for each of those, but it was a pretty amazing experience. And this is something where if money is no issue, and I can figure out a model that makes this work – I see this as being potentially like the legacy that I can leave, to make this a global movement in the way that Startup Weekend became a global movement. So, the plan now is to – I’m going to do a couple more events locally in Lisbon, and then, there’s a couple of us that are aiming to do a road trip mid-September to mid-November, ultimately try to terminate it in Istanbul to coincide with the next Nomad Cruise. And so, yeah, I think we’re going to try to deploy it in eight different European cities. And yeah, I would love to have – anyone listening: if this sounds like your thing, it’d be amazing to have you involved. It’s just Charitymakeover.com; if it sounds up your alley, you can submit your details there, and I’ll be in touch with you.

Matt: Can you talk specifically about what happens that weekend? So, first of all, what types of people can volunteer? And then, of the people that do volunteer, what exactly does the weekend look like?

Sean: Yeah, so we can take pretty much everyone, depending what your skills are. Developers—obviously are very in high-demand—but designers, copywriters, anyone who has experience with PR or grant writing, or working with non-profits specifically, you name it. And even if none of those match what you do – translators, anything, we can use pretty much everyone we can get. But the idea is to really just find local charities that are poised to do great things but lack the in-house expertise in things like marketing. And they’re focused on whatever their cause is and solving that, but they don’t know how to promote and how to fundraise, and how to basically manage a non-profit. And so, we parachute in, and in very short order build the most high-leverage digital assets we can for those folks. And yeah, just really try to advance their cause for them so that after that weekend, they’re in a far better position.

Matt: Yeah, I think that’s really amazing what you guys are doing. You’re putting together this highly skilled dream team of individual practitioners who can do things like build websites, or write copy, or create marketing campaigns, and you’re all coming together, and coming in to completely overhaul the infrastructure of a charity in an extremely short period of time.

Sean: That’s right. Yeah, I mean, it’s what I envision if they were to reconceive the Peace Corps in this day and age. Like if you were to rethink what does that look like in the age of knowledge workers and people that don’t have two years to commit to something, and go live somewhere, and dedicate, but they could intermittently participate remotely and help causes that way. I mean, the tools have come so far, and this is really a thing now. And so, I really think it’s like what the Peace Corps would look like if they were to re-envision it today.

Matt: Cool, so what we’ll do is: we’ll put that website link at TheMaverickShow.com in the show notes, you can just go there and get all the links from this episode. And if you would like to contribute your skills to one of the Charity Makeover projects, you can just click through that link and check out the opportunities to do that, help out a charity, and also, to collaborate with some other amazing people that are involved with these projects. 

Sean, at this point, I want to continue a little bit on the music discussion. I know that you have a very wide range of appreciation for a lot of different types of music, one of which that we have in common is Hip Hop. And I want to just ask you about how you came to connect with that particular art form, what is it about Hip Hop music that resonated with you? And what is it about Hip Hop that you connect with and appreciate?

Sean: Yeah, so, I’ve always had this weird, rebellious kind of fight-the-system kind of gene, as evidenced in my hacking-the-photoradar-thing, which is just one of many stories like that. But I have a real deep mistrust of government, to be frank. So, I think that is what resonates with me – or not just government, but authority in general. So, that’s kind of what I connect with in terms of Hip Hop. And yeah, I think we share a lot of the same influences like old school/’90s type artists. Always love talking with you about the genre though, man.

Matt: Yeah, you know it’s been really amazing here in Nigeria to see the number of ‘90s Hip Hop in particular that is regularly played today, in 2019. I’m talking about in Uber rides, at pool parties by the beach, in restaurants that have DJs, it is all over, it’s completely prolific. I’m talking about artists like Biggy, artists like Naughty by Nature; it’s absolutely ubiquitous everywhere that you go here, and it’s particularly the ‘90s Hip Hop from that era. And it’s amazing to see that this many years later, in 2019, this current generation of people still has that level of appreciation for that music.

Sean: I think they stuck a nerve. I think that people identify with a lot of the themes that they have in that era of music, and it’s relevant. It’s interesting to see pockets of that and where it’s popping up, and why people are identifying with it, you know? I think it’s timeless, and those sentiments are no better captured than they are in that music, and that’s why we still see it around today.

Matt: Yeah, for sure. And at this point, Sean, I want to ask you about your podcast, which is called Nomad Podcast. I know that you did season one, and then you took a pause, and now you have just launched season two. And I want to ask you about that, give you an opportunity to talk a little bit about anything that’s different about season two, and what people can look forward to when they tune-in to season two of Nomad Podcast.

Sean: Yeah, thanks for that. I mean, so truth be told, you were impetuous in terms of compelling me to reboot it. And so, I thank you for that encouragement and all the tips you gave me, you gave me a lot of good advice. In terms of what’s changed, basically, I had – I don’t know what I’m doing, right?  I’m in front of a camera recording people I think are interesting, but learning as I go, and refining it. And you convinced me to get better, high-quality audio gear; so I got the Zoom 6 recorder, I got some professional mics, dialed that in. I also changed the format a bit, got a professional intro/outro, did the teaser. I pretty much follow your format in terms of how you drop that little compelling teaser upfront that gets people to listen to the episode. It does have a video component, so most of mine – or all of mine at this point I’ve filmed in-person, so I was fortunate to interview eight people after the Nomad Cruise. And so, I’ve had a steady stream of those hitting each week, and I was able to get a video with each one of them, and that’s like a little one-minute commercial for what they’re going to get by listening to it. So, all told, yeah, it’s just refinements to something. But the mission in my podcast is really to—like the Nomad Prep Academy that I  created—it’s to help others who are considering this lifestyle, who think that maybe they can’t do it. It’s to give them education and inspiration to make that leap and to do it, and be successful at it. So, I record basically three different groups of people: Nomads, what I would call “domain experts,” and founders, so product and program founders. And those three groups, I think between those, you get a really good cross-section of things that can help aspiring Nomads take the leap. So, that’s what I do, and then, all of that – the way that the podcast came about, I had produced the course first, I built an e-course called Nomad Prep, and this is like the two-week academy that I wish existed when I was preparing to do a remote year. No one really laid it out of, “Oh, this is what you need to worry about in this sequence. And then, go figure out – make sure you have your job situation on lock. Now you can shift emphasis and let’s take care of the minutiae around vaccines, and visas, and all that junk. And insurance, and storing your stuff, and selling your car, and doing all that stuff.” So, I basically, just wanted someone to handhold me, and put it on autopilot, and be like, “This is what we’re doing today, this is what we’re doing tomorrow.” So, with my course, you go through two weeks, and we just focus on a few things each day. At the end of it, you’re basically ready to get on a plane. And it paces it out, there’s a 42-point checklist that it runs you through. You can track the progress of what you’ve completed and what remains to be done, and then it will remind you as you get close if you’ve missed a crucial step, it’ll say, “Hey, you forgot to get your immunization, we’re three weeks out.” So, anyway, super-useful tool, a lot of people like it, but I just didn’t have a good way to promote it. And so, the podcast was kind of the next logical thing to build around it, it was like, “Oh, I can interview people, and then we’ll direct them to the Nomad Prep if they want to take it a step further,” so that’s how it came about.

Matt: Awesome. So, we’re going to link-up to the Nomad Podcast in the show notes, but it’s available everywhere, on iTunes or Spotify, or wherever you listen to your podcasts, you can go and check it out. But we’ll also have a direct link at TheMaverickShow.com in the show notes. And the Nomad Prep Academy we’re also going to link-up to that in the show notes. Now, I understand that people can start the Nomad Prep Academy for free, that the first few modules are completely free. So, they can just click on the link, go through and just start taking it and checking it out, and seeing what it is. And then if they want to continue and go through the whole thing, they can end up paying for it, but they can start it for free. Is that correct?

Sean: Yeah, that’s absolutely right. The first four days are free, and then, if they want to continue with it, they just pay; I think it’s a one-time charge, and it’s pretty reasonable. Just last week rolled-out the beginning version of the affiliate program. So, if you’re listening to this episode and you are already a Nomad, and you get asked that question – people see your Instagram, and they’re like, “Do you ever work? How do you do what you do? I want to have your life.” and you find yourself answering these DMs, these long, extended conversations with strangers explaining how you do what you do. If you face that scenario, basically, I made it so that you can point them to my course. You’ll be helping them, and you’ll get paid on it as well. So, you can learn more about that; it’s just NomadPrep.com/advocate.

Matt: Cool, so we’re going to link all that up in the show notes. And Sean, at this point, the final area that I really want to go into with you is a little bit on the personal growth and productivity side of things. And I know that you have a really interesting concept that I’d like you to talk about called reverse goal planning; can you explain what that is and how it works?

Sean: Yeah. So, I was first exposed to this way back in the day. I had reviewed a book called Innovation Games; the author was Luke Hohmann. And he had a number of games that he had created that were just games that you would play in a corporate setting with product owners and their customers. And it would be a way of unearthing insights. But he had this one in particular called “remember the future” that was all about basically a unique way of how you plan a product. And instead of thinking like what should this thing be? You project yourself forward, and then look back and “remember the future,” quote, unquote. And it’s just a different way of thinking about it. What’s interesting is, I’ve seen something recently, Amazon does this in a very specific way. The Amazon approach to product development is they will write a press release that they want to run six months from now. And it forces their people to think, “Okay, what do we want to be celebrating and saying, and how are we talking about the product and what has happened up to that point?” And it’s just the same concept of project yourself forward and look back, and what must have occurred by that point in order to be able to publish this press release. And it forces you to think differently and really get clarity on some of the product development decisions that led up to that point.

Matt: Cool. And then, you have another concept that you shared with me called “punching past the board,” can you share what that means to you?

Sean: Yeah, so “punching past the board,” I way, way, way back in the day took Taekwondo, and I had this insane, level-five blackbelt instructor. This guy – I watched him break river rock with his hand. But breaking a board – if you try to hit the board and you aim for the board, you’re going to break your hand; you have to aim at a spot that’s past the board. And the analogy there when applied I think in business is: that if you’re trying to accomplish a certain goal—case-in-point being like with our Charity Makeover thing—if we’re trying to this weekend knock-out this very small fundraising project idea, it is helpful to punch past the board, so to speak, in terms of getting them to see the larger picture. And so, I will go through this exercise where we’re doing visualization, we’re thinking about: who are the refugees that we’re helping; imagine being ripped from your homeland and coming in as a Syrian refugee in Lisbon; not having a source of income; not knowing the local language; like really embed and put yourself in that position, and feel what that’s like. And then, that is the person that we’re serving here, so then, that is the ultimate goal. And then, that becomes like: okay, so it’s not a fundraising campaign, it’s like that person that we’re helping. And once you can identify with that and internalize those emotions, and what that must feel like to be that person, it just energizes you. So, I think that’s a good example, but you can apply that a lot of ways. The point is: don’t think about the end goal of what you’re producing at that point, think about the bigger picture beyond that because that’s what fuels you to get through whatever the immediate challenge is.

Matt: I love that. Can you now talk a little bit about your personal productivity habits, routines, practices; how do you structure your day; do you have morning routines; how are you able to create the amount of output that you do for work and all the other things that you’re involved with?

Sean: Yeah, I didn’t use to. I’ve developed a pretty elaborate morning routine that I’ve been doing for the last couple of months. So, what that looks like – basically, one of the podcast interviewees that I interviewed—Danielle Thompson—convinced me to do this, and I’ve been doing it, and it’s a great practice, but a gratitude journal is the very first thing. So, when I’m just waking up in the morning, and I’m still out of it, and sleepy, and whatnot, I have a little book by my nightstand, I pick that up, and I just write three things that I’m thankful for. And then, one mantra, or affirmation, or a song lyric, it’s whatever I’m kind of feeling is like the theme for that day or that week. And I’ll write that down, and that’s just the very first thing I do. And then, I do this thing called “Wim Hof Breathing Method,” you can look that up, it’s a whole thing. But it’s basically a type of breathwork that oxygenates, hyper-oxygenates your body, so I’ll do that for 30 minutes. And then I do “Sam Harris, Waking Up,” it’s a podcast – well, it’s actually an app now, but it’s a type of meditation program that he does, similar to Headspace but I think it’s a little better. And then, I will drink a bunch of water, either go for a run or do TRX. So, I alternate, I’ll do minimalist running one day, and then, I’ll do TRX—which is like a suspension trainer workout in my house—the other day, and then that’s my morning. That sets me up to be productive that day. And all told, I think that the whole thing takes about two hours. But what’s cool—this is actually one of the cool things about being on Lisbon hours—is that working Europe hours – most of my team is on the West Coast in the US, so my day doesn’t really start until about 2:00 p.m. Lisbon time. Which is nice, because that means I can have an involved morning routine that I wouldn’t otherwise do just from time constraints. Back in the US, if I were to that, I’d have to be getting up at like 5:00 a.m. or 6:00 a.m., and I’m not a morning person. So, this allows me to do that, and then I work into the night, and it’s great.

Matt: Awesome! All right, Sean, at this point are you ready for the Lightning Round? 

Sean: [Imitates lightning striking] The Lightning Round. Yes, let’s do it.

Matt: Let’s do it.

Announcer 1: [Lightning striking] The Lightning Round.

Matt: All right, now, on the last podcast, you got the Lightning Round question to name your top five Hip Hop MCs of all time, which you did. But I understand that in preparation for this podcast, just in case I was going to ask you for another five, you prepared Hip Hop MCs No. 6 through 10. And since you had that prepared, we are definitely going to lead off with that. So, Lightning Round question No. 1: who are the next five MCs to round-out your Top-10 of all time?

Sean: All right, so for No. 1 I’m going to go with a relatively new person because we’re both from the same era now, but Kendrick Lamar. I think he is arguably the Dre of this generation. So, I would have to say Kendrick Lamar is probably No. 6. I have to say Jay-Z is No. 7, Hova. And I’m going to throw a curveball for No. 8: I don’t know if you know this guy, but Sage Francis. Yeah, so this guy – look him up, Wired Magazine – I first learned about him through – Wired magazine did some kind of study where they actually took all the top Hip Hop artists, and they tried to see – they analyzed their vocabulary based on all the lyrics they had written. And so, they wanted to see who was the most well-read and well-spoken Hip Hop artist, and DMX I think was on the other end of that spectrum with like the lowest number of words used in his songs. But Sage Francis, this guy was one of the most well-spoken, and so, I got introduced to him that way. But he is an absolute poet, this guy’s lyrics. He has so many lyrics per song, but they’re amazing. So, I would put him up there; I’d say he’s probably No. 8. I’m going to say No. 9, another maybe obscure one, but People Under the Stairs, they’re an old school one. I think I’ve recommended them to you before, but they are really awesome, kind of like West Coast—LA, San Francisco—old school vibe. And then, for No. 10, I’m going to say Zack de la Rocha, which is maybe an interesting not-necessarily-Hip-Hop, but like a cross-over artist, Rage Against the Machine’s old singer. But he — I think has that spirit, you know, that rebellion and that just fierce anger, just raw rage. I don’t know how – Zack de la Rocha, though, I think would be No. 10.

Matt: Awesome. Okay, next question: what is one tip that you have for stress reduction or stress management? When things get really hectic and stressful in your life, how do you handle that?

Sean: So, I’m pretty fortunate in the role that I have now. There was a lot of stress back in the day with JumpBox because it was my company and it was just – it was a really dark time, and we confronted a lot of uphill battles. It’s not that there is no stress with Pagely, but I have a far less-stressful environment these days. I would say when there is stress, exercise is definitely the best thing I can recommend. Just getting out and doing something, or just going for a walk. Break up your day, get some sun, reset your mind, listen to a podcast, or music, or anything else that just kind of resets you. Yeah, but other than that, I don’t know, exercise is probably the best thing you can do. Running, I love running; I do, again, the minimalist footwear, like Vibram-style running. And to me, that made running interesting again. I was a long-time runner of just using regular shoes, and so, that was kind of like the reboot to my running career, was getting into that about six or seven years ago. But I highly recommend just any form of exercise is probably what I’d recommend for stress.

Matt: All right, from all of your world travels, what is one travel hack that you can recommend to people?

Sean: Man, I can’t remember what I answered on the last episode, so I don’t want to repeat it. I mean, the thing that comes to mind is—and it’s so stupid—but loop the strap. On whatever backpack you’re wearing and wherever you’re at, loop the strap through your foot or at least put it around your knee so there’s pressure and you feel it. In any of these places, if you go and you sit on a patio, and you put your backpack on the back of the chair, don’t do that; don’t put it on under the table not touching anything, it will get stolen. So, yeah, I mean, just put it so there’s always pressure, and you can always feel it, and that’s just muscle memory for me at this point. Like anywhere I go, if I’ve got my laptop, I will just loop the strap so I can feel the pressure and I know it’s there. So, that’s like the simplest hack I can think of. I don’t know, there’s a bajillion hacks in my course, so take Nomad Prep. That’s a cheap, shameless, self-plug for Nomad Prep there, but there’s a lot of those type things.

Matt: All right, I know that you do self-defense and safety training for people, so I wanted to ask you for one safety tip that you have let’s just say for solo travelers, for example?

Sean: I think the biggest thing that most people can do to improve—and it doesn’t even require taking a self-defense course—but like just self-awareness, situational awareness. And being – we walk around – if you think of it as like a scale of white-, yellow-, orange-, to red-alert, most of us walk around in this white level of awareness where you couldn’t even name or describe the person who’s walking behind you or next to you, or what’s going on. Most of the time, we’re in our phones, we’re not paying attention, and we don’t know what’s going around us. So, the simplest thing you can do is just to operate at a yellow level, don’t be on red-alert, don’t try to like go nuts and become paranoid, but just know what’s happening around you at any given moment. This is also just really good awareness and training to be more present in the moment: if you just kind of – someone had this tip I thought was so great that it’s like every time you get the urge to look at your phone, let that be a reminder to become present in the current moment. And if you can make that the trigger, that anytime you go to check Instagram, or check your email, or whatever it is, just let that become the like, “Oh,” yeah, become present, come back to the moment, look around like what’s happening. I think if you do that, that’s the simplest thing. And of course, there’s a whole bunch you can get into in terms of like de-escalation, and distance, and combatives, and all that stuff. But that is probably the single best thing and simplest thing anyone can implement to improve their personal safety.

Matt: I agree with that a lot. I think that is really, really good advice. Okay, last question: if you could have dinner with any one person who’s currently living today—it could be a celebrity, author, public figure, anybody that you’ve never met—who would you choose and why?

Sean: Yeah, Naval Ravikant, 100%, and it’s a name that probably not that many people know. But this guy is modern-day – he’s a venture capitalist – the dude is just a prophet. He is so enlightened, and so well-read, and well-spoken, and not at all mercenary, I would say. He’s made a ton of money, and yet, you’d never know it. He’s like the Bob Marley that made a billion dollars, he’s just like – his attitude is so cool, and he’s so sharing with his knowledge. But Naval Ravikant would be my choice for dinner. And just in terms of why: what an incredible human being. He has a podcast, I listen to it, I read all of his stuff, and he Tweets and everything, the guys is just like a wealth of knowledge, and has such a chill attitude. So, I would want to have dinner with him.

Matt: All right, Sean, I want you to let people know: how they can find you and connect with you; how can they follow you on social media; how can they learn more about what you’re up to and get involved?

Sean: Yeah, for sure. I’m just Scrollin’ On Dubs on social media, it’s just no “G,” but Scrollin’ On Dubs on Twitter, Instagram, and Facebook, all that stuff. And yeah, I mean, you can go, I’m sure you’ll link this in the notes, but Charity Makeover would love to hear from you, it’s just CharityMakeover.com; my blog is ScollinOnDubs.com; and other than that, yeah, you can probably just find me on the Internet, Google my name.

Matt: All right, Sean, as always, so good to have you on the show, my man. Thanks for coming back.

Sean: Always a blast, Matt. Take care, my man.

Matt: Goodnight, everybody!

Announcer 1: 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.

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[End of Audio]

Duration: 82 minutes