Ash co-founded the Lisbon Digital Nomad Meetup which has become the largest meetup of its kind in the world. Learn how he did it.

Ash founded an online vintage arcade emulator site when he was 13 and has had a number of entrepreneurial ventures since. He crossed paths with Trevor Gerhardt of the very first Remote Year group while they were in Turkey and has been a pillar of the Lisbon nomad scene having founded the Digital Nomad Meetup group. That group has been so successful that sent delegates to study how it’s operated to learn why it’s thriving so well.
In this interview we’ll hear about Ash’s video game business, his entrepreneurial journey since his first venture, what’s been involved in growing the largest nomad meetup in the world and what he’s up to with his latest venture purchasing and renovating a coffee shop in Lisbon. Enjoy.

Show Notes

Time   Topic
0:02:22   Welcome and context
0:03:25   What is Retro gaming?
0:08:44   What was the Dubizzle Startup?
0:13:26   Tell us about your transition into digital nomadism?
0:15:26   What was the startap scene in Chile?
0:17:22   What have you learned from that experience?
0:21:03   What was different about the Chile Startup program?
0:24:53   When did you move to Lisbon?
0:26:12   What were your motifs for starting the meetup group in Lisbon?
0:32:47   How did you end up running a coffee shop in Lisbon?
0:43:20   The importance of branding and culture
0:44:45   What is one book that profoundly affected you?
0:45:47   One person you’d love to have dinner with?
0:47:12   What is your favorite tool or hack that saves you time, money or headaches?
0:48:12   How did you get into meditation?
0:49:22   What important truth do very few people agree with you on?
0:51:00   If you could go back in time, what would you tell your 20 year old self?
0:54:41   How can people get in touch with you?


Lisbon Digital Nomads
Remote Year
Ep #1 With Tevor Gerhardt
Nomad Cruise
Charity Makeover
Google Ventures 3 hour Branding Sprint
The Untethered Soul: The Journey Beyond Yourself
Michael Singer, Tony Robbins and Sage Robbins
Isha Kriya Meditation
The Surrender Experiment
Selva Lisboa



Image 1 of 1


Sean Tierney: 02:22 All right. Hey everybody. Welcome to the podcast. I’m your host, Sean Tierney and I’m sitting across from Ash. Ash founded the digital nomad meetup group here in Lisbon, which is currently the largest digital nomad meetup group in the world. He also, uh, this is also the largest meetup group in all of Portugal. Ash worked at an early stage startup pre-investment called Dubizzle that later became the largest classified ads portal in the middle East and North Africa and was later acquired by OLX at the ripe age of 13. Ash founded the largest retro gaming website in the world and rode that train for 18 years. His latest hustle. He’s just recently purchased a specialty coffee shop in Lisbon and is now learning the food and beverage business rapidly scaling this latest venture. Welcome Ash to the show.

Ash: 03:06 Thank you for having me here, Sean. It’s great to be here.

Sean Tierney: 03:09 Awesome. Okay, so I figured, uh, we’re doing this kind of hurry up. Offense is like my last day in Lisbon for awhile, so I’m, I’m stoked that you were able to come in and I figured we’d just kind of go chronologically through your history. Just like what you’ve been up to. Um, why don’t we start at age 13? What first off, what is retro gaming? What does that all that?

Ash: 03:25 Well, it’s these old video games that you can no longer purchase anywhere. And, um, while I grew up in India and what happened was that I hadn’t played a lot of those games because back then the video game industry didn’t use to market in India. So when I found out about this technology called emulation, I figured that I could somehow play those games and you know, catch up with global culture in a way. And I started playing those games and I realized that they would be a lot of other people like me who would want to relive those games and those experiences. So I started this website and I started, you know, uh, helping people out with emulation and stuff like that. And that’s how they got, you know, really into it. And it grew slowly and steadily, but I worked on it for 18 years and eventually, I mean, for the last eight or 10 years, it was the largest retro video games website.

Ash: 04:12 And in the world, Alexa, top 1000 and all of that. So it was amazing. So we’re, we’re talking about like these massive arcade games. Yeah, exactly. Yeah, yeah. All the favorites that you ever played, you know, all the favors that you wasted all your coins on. They are kids. All of them were there and people would really, I would get a lot of amazing feedback from people, emails from soldiers that were at war or people who were, you know, um, hospitalized for long periods that you know, that the only way they could cope with their situations was playing the games that they were, you know, into as kids. So it was a really rewarding experience in terms of just running that side and giving those experiences to people somehow. Nice and cute. Was this something where people would download these things and play them locally on their computer or is it possible to actually play these in a web browser?

Ash: 05:04 How does it work? Well, back in, so this is the thing, like I’ve been, I started the website, um, I think we had the Pentium two processor at that time. So, you know, we didn’t really have the kind of computational power, uh, you know, an iPhone is way faster than any of those computers today. So back in the day you had to download special software and download the games and you know, run them and sometimes they wouldn’t even run at full speed. But today you could play them inside your browser, you could play them on your phone, you can play them anywhere really. Probably even on an Apple watch. I never tried it, but it’s possible I guess. What’s the like business wise, how does it work? Like licensing? Did you just like, cause I would think people like Nintendo or whoever those big gaming companies back in the day, like do you have to then like purchase rights from them to resell it or are these just kind of like public domain after a certain amount of time or how does that work?

Ash: 05:55 No, I, the issue here is that a lot times these the studios, so it’s the studios that develop the games that own the rights to the games. And most of the times I’d say about 95% of the times, the studios don’t exist anymore. The companies do not even exist. So there is no provision or way of purchasing the licensing for most of these games. There are some companies today that are trying to find out who, you know, what the chain of copyright ownership was and who’s the final, you know, holder of the estate that holds this license and stuff like that and try note, we release the games, but you’re only able to track number about 5% of them. So what we did was we had games available there for free and what people could do was play them. And if we ever received any kind of issue or complaint from somebody saying, Hey, this is our game, you shouldn’t distribute it, we would take it down and that, that’s what we did for the longest time and it worked fine.

Ash: 06:45 There was no issues with that. Right? So that’s how we worked it out. Cool. So it’s almost like in the same way that like you don’t have to police a website, but if you get a DMC, I take down requests, you’ll just honor the request. Yeah, absolutely. I mean, ultimately we were in, in interested in preserving the games and not, and, and, you know, having people have those experiences. And you know, this type of stuff is very important today because if you look at the movies from the 1920s and thirties and forties, 99% of them have vanished because of lack of preservation efforts. And the same is happening with video games right now. Like games from the 70s, 80s and 90s are just, you can get, get your hands on them anymore because the physical media degrades over time and you can’t even find them anywhere.

Ash: 07:27 And then, um, you need to digitize them and store them and distribute them so that people can have those experiences in container environments. So we’ve been trying to do that, uh, and honor any copyright issues there. Never really had any trouble with that, so that’s awesome, man. Yeah, you’re like a museum preserving all these. Yeah, absolutely. Yeah, absolutely. But, um, so it’s, it’s been a really interesting journey and it’s just amazing how much people love those games. It’s, it’s just unimaginable because when I started the website, I thought it would be people who had not played the games that would be interested in them as was I, but it was also like people that had played those games in their childhoods and often now they were fathers or mothers and they wanted their kids to experience the games that they play it as, as children and you know, like those kinds of things. So I think back to like the arcade after school and seven 20 skate or die. Yeah. Marble madness and shoplifter and these games that like, yeah, you just, it was a magical, I can see why people, like there is no substitute, like playing that again will take you right back to whatever those are. Exactly. Absolutely. And that nostalgia, I mean, nostalgia never gets old. That’s the thing.

Ash: 08:41 Never gets a hold. That’s awesome. Let’s shift to the dub ISIL startup. What was that all about? So I had moved to Dubai for a few years and because I had experience, let’s be honest, I was a terrible developer. Like I, this website that I developed, I just kind of learned how to develop it online and I kind of hacked it together, you know, using PHP and HTML and all that stuff. But, but I was a self starter and a motivate, motivated person. So, um, when I saw the Bizzle and I was looking for a job, I told them about my website and that I’d been doing this stuff and they said it was very interesting because I send them, I was looking for a job and I sent them my resume at 4:00 AM because as whatever, late night owl and um, they got in touch with me at 10:00 AM saying, Oh, we’d love to talk to you.

Ash: 09:30 So it was a really quick turnaround. They saw my resume, they were like, Oh, this guy sounds like it’d be cool to have him on our team. And they got in touch with me and I started working with them. I think I was the fourth or fifth person on the team and um, it was, we were in a small Villa that, that they had rented. And uh, it was very chilled out and unofficial and we were working on the new release of the, of the platform at the time. And then we got institutional investors in and they came in and within one and a half year, the company went from like seven people to 55 and in another six months had went to 200. So we moved from that to the 15th floor in a glass tower to the 30th floor in different glass tower.

Ash: 10:14 And then it just grew like tremendously. Yeah. But that’s what brought me to the next phase of my life where I felt like it became too corporate. There were too many processes and the impact that I was having was now too level two, you know, enjoy. So I decided to become a nomad at that point of time. Well first I said I’d like to go on a break for like four months or six months. And they were like, no, no, no. Just 20 days. We need you here. And I said, okay, then I quit and I got to go, you know. So, um, and that’s how in 2011 I became a nomad and nobody called themselves and no matter at the time, the term had not even been like, well, no match. Sure. But digital nomad, nobody said that that phrase didn’t exist back then.

Ash: 10:56 Well, I feel like even today, like people who are doing it don’t call themselves that. It’s just one of these weird terms where from an outside that’s how you have to refer to it because we need some label for what it is, what we’re doing. But yeah, absolutely. So I think at the time people would just call themselves remote professionals or location independent travelers or you know, this kind of stuff. Yeah. But yeah, but I think the term digital nomad, or maybe I’m deep inside the bubble right now, so I had no idea how it’s perceived outside the bubble. But, uh, I didn’t hear it a lot. I didn’t hear a turnaround a lot back then. But now I, I see a lot of people know what it is. And you know, yeah. So I think it’s probably a bit more common place at the moment.

Ash: 11:36 Ironically male, if I was a developer as well, back in the day, a terrible one. I boom. And I was good enough to make apps. I like, I taught myself the things I needed to know to make something, but you know, like horribly in elegant way. Right. And it was just enough to like get the right thing working and then it would just inevitably break because I was CS trained. But uh, I feel your pain in terms of like scaling to the point where it’s not funny anymore and now it’s like very corporate and yeah. But the good thing was that I really, um, so I used to be a bad developer, but working with the people at the Bissell, I learned a lot. Like just working full time with a really great development team. Um, very switched on people, very talented, you know, a players.

Ash: 12:25 I learned so much that I was able to at that point make a lot of improvements to my website as well. And that’s how I became like really confident that I could build any kind of platform for anybody. And that’s how when I was a nomad, I ended up becoming CTO of this startup in Chile because I was confident enough to be like, Oh you need this platform, I can build it for you and I can make a team and we can do it together. Well I think that characteristic is also interestingly enough in the space of no matter, and I feel like that’s one of the muscles that gets worked really well is when you are constantly put into these different environments of new challenges and new sets of circumstances and people and like figuring stuff out is a skill. And so it doesn’t surprise me that like you gravitated to that and then you were able to absolutely.

Ash: 13:14 I think today the world is just divided into two sets of people, those who know how to Google and those who don’t. So if you’re good at figuring stuff out, you’re so far ahead already. Yup. Yeah, for sure. So let’s talk about that transition. So you became a nomad and was that about the time when you met the people on remote year with their thing or was that before then? Um, no, I was the, no, I became a nomad in 2011 so remote here. I met in 2015 so while I was traveling in Istanbul, that’s when I bumped into this, uh, girl [inaudible]. She is from New York and she wasn’t the first remote your batch. And I think she was following me on Instagram or something like that. And she said, Oh, let’s have a coffee. And then she, I said, Oh, what are you doing in Istanbul?

Ash: 13:57 And she said, Oh, I’m in this thing called remote here. It’s a new thing that just started. Uh, why don’t you come and have dinner with us? And what they used to do back then was, I don’t know if they do it still, but back then in remote here, every, if you had your family in the city that you were in, sometimes they would do like a small dinner with your family, just like a select group of people. So I met Sam and Trish and we played some guitar and we signed some songs. And because the girl, there was a Turkish girl in the group at the time and her family was from Istanbul and her father was a famous musician. They could Turkish musician. So they invite us for dinner and then we, you know, sat around and played some music together and it was a really beautiful evening.

Ash: 14:36 So that’s awesome. Yeah, I was, I was very intrigued with remote here because I thought that it’s a, it’s a really cool concept for people to, you know, take the leap if they’re not feeling that confident about, you know, being nomadic at some point of time. So that’s how personally I waded into this lifestyle. So it’s, it’s definitely good gateway drug. Yeah, absolutely. I mean, I think it shows you the best possible scenario in terms of community and organization and everything. And then, and then you can be like, Oh, I could also continue to do this on my own. And it kind of, you know, it’s like the training wheels. Right. So, yeah, for sure. Uh, interestingly enough, Trivor Gearhart, I don’t know if you remember him, but he was good friends with Trish. Uh, he was in that group. He was my first guest on the, of the podcast.

Ash: 15:18 Okay. That’s a crazy coincidence. Yeah, that’s, that’s funny. Cool. Um, okay, well, so in Chile, Chile has a good startup scene, right? Like I know they have that startup Chile program. That’s exactly what you were a part of. So yeah, that’s what it just happened randomly. So my first year of nomadic in 2011, I mean it was already 2012 at the time. I, after like six months, I was kind of feeling a bit like I needed to be productive again. So I was a bit concerned about doing something. And then I was in Sheila and there was this startup charity program going on over there. I just accidentally met, met a couple of people. It was a different startup. It was a startup called girl tank and they are a social entrepreneurship startup. And their mission was to empower female change-makers. So female social entrepreneurs.

Ash: 16:09 And they wanted me to build the technology platform for them, but they were not very clear about what they needed. So we tried to work out the specifics but it didn’t work out. But in the meantime I met these other guys who were building gap jumpers, which is a recruitment startup and they were pretty clear about what they wanted. So I joined them as cofounder and that kind of became a sub adventure of my whole nomad adventure. And so we founded that in Chile. And after a while we raised some money, we moved to San Francisco, we raised some more money, but we didn’t really achieve the hockey stick growth that San Francisco investors won. So I spent some time there, but we kind of like ease into a lifestyle business kind of mode. And that’s where the company’s at right now. We serve as like big clients, but it’s a very boutique kind of recruitment service and that’s pretty much it.

Ash: 16:55 Are you still involved with that venture? Have you been done peripherally? I’d say I, I left my role as CTO several years ago, but I still consult with them. They still need help because I built the entire platform, so I kind of know it best still even though they have some people working on it. But yeah, if they need something very specific, they ask me for it. So that’s how I help out with them sometimes. Would you like, what’s your big takeaway from that experiences there? Would you have raised money knowing what you know now or do you think that was the wrong decision given that business? To be honest, I, I really think that we spent a long time just dealing with our investors and their expectations. If we would have, we were able to get fairly good clients like McKinsey, Adobe, Dalby, Mozilla, you know, on our own and work with them directly.

Ash: 17:44 But our investors had different expectations of us. And to match those two sides took a lot of effort from the founding team all the time and they wanted to push us in various different directions that we didn’t feel were the right directions for us. So if you would have been like, okay, if you want a business that makes you know, 500 K to a million a year and then, you know, grow it slowly, I think that would have been much more feasible and we would have been able to do that much easier had we not taken on investment and been like, they should be a business that makes 100 million a year, you know? So I think sometimes not every business is suited to that kind of growth. So you really need to assess your market size and understand the demand and also figure out what you as a team are capable of and comfortable looking into.

Ash: 18:28 But there’s also egos involved. You know, everybody who makes a startup once it to be a unicorn or somewhere close to that. Right. So my, my co founders were like, no, we want hockey stick growth. But then three years into it they were like, uh, this has been a very humbling experience. So I think everybody really comes around to it. Eventually. We just did the long way around that said, yeah, I founded one in 2006 or cofounded one called jump box and ran that for nine years. And we did like some friends and families from angel and we were on track. We’d met with like Sequoia and about 13 other VCs in San Francisco had a verbal go ahead from Sequoia and then 2008 happened with like the whole financial collapse. So that got pulled out from under us and definitely agree. It was a humble experience, humbling experience in terms of, uh, just like realizing like going from that, that unicorn path to like, okay, no, we need to be profitable and lean and mean and like very, uh, austere in how we operated.

Ash: 19:25 Uh, it was definitely a tough, tough thing, but good experience. A good learning experience for sure. Yeah, for sure as well. For me, I just, I never realized, uh, like it kind of made me understand why shark tank is called shark tank. So know you kind of learn about how the investment environment and what your, cause I think when you read tech crunch and all these um, blogs, you have a different picture of, of what the ground reality of the situation is. How do you, how you raise money, how do you approach VCs, how do you get them interested? Like how do you court them? Really? Yeah. And I think it’s in the dynamics of their, I think the key thing for people to understand is VCs operate with different dynamics than like a founder operates with, right? You’re an N of one. This is your baby.

Ash: 20:09 You’re just trying to make this thing work to the greatest degree you can. They see it as a portfolio place. So you’re just 20 companies, right? You’re just one file on their shelf, you know, it just doesn’t matter to them. So, and they’re like, they just have a different mentality where like they’re going for broke on everything. Like we want their model is like one of these is going to hit unicorn and 19 of them are going to fail and we’re going to make it on the one that’s a unicorn. So we’re just trying to make each one of them be a unicorn. But you’re just playing the tables at the casino. Exactly. And we’re just the dice. So it’s, yeah, exactly. It’s a great way to put it. Cool. All right, well, so, um, I I think what’s interesting about the um, uh, just that

Sean Tierney: 20:48 Chile is startup. Like it sounds like it’s really like that whole program. I know it’s attracted a ton of, of talent and whatnot. Like they’re doing something right with that program. I’m just curious if you had any insights, uh, being in that ecosystem for like what they figured out that other places didn’t or if there was anything different about Chile or Santiago that,

Ash: 21:08 well, the main thing with Chile is that they, their economy is heavily dependent on copper. So copper mining and now off late lithium is like their main bread and butter. Their economy is not diversified and the Chilean government is aware of this. So they were like, okay, we need to somehow um, you know, increase entrepreneurship in our country because for every middle class to wealthy Chilean kid that grows up, they know that they have a future in the corporate industry. They know that if nothing else works out, you know, there’s copper. So the government was aware of that and they really were good at creating this. Like usually your, you know, you deal with government bureaucracy and you feel like you just want to cry, but that they develop the system fairly well and it’s fairly efficient. It’s fairly transparent. You get, at the time when I joined it was you get $40,000, um, no strings attached, almost capital to start your company.

Ash: 22:06 You get a visa for one year to work in Sheila to hire a team or do whatever you want and yeah, that’s all. You just gotta make it work. It’s literally, here’s 40 K make this work. And they are just hoping that looking at all these people, you know, the Chilean applicants to the, to the program will be more inspired to also be entrepreneurs and at least if that’s their end goal, they’ve been really successful because in the beginning it was just foreigners. Like most of the people who participate in the program were coming from abroad. But five years into it, a lot of the startups in there allow Chilean. And so they’ve really been successful and in encouraging that kind of entrepreneurship and you know, that kind of ecosystem in their own country. And the only thing where I think the SF system is better is just because investors are more ready to put cash into startups over there.

Ash: 22:58 So the, that’s the same reason why we ended up in San Francisco is because you just, it’s really difficult to raise money in Chile. And I have heard from European startups as well that it’s fairly difficult in cities like lesbian or Paris even compared to San Francisco. So, um, investors are much more likely to take risk in, in San Francisco versus in Sheila ever. They’re very conservative. And so that’s something that they’ve been trying to address by also introducing further rounds of investment straight from the government as well. So you could apply for up to 120 K, you know, so to like just kind of take you to the next level before you need that series a round or something of the sword.

Sean Tierney: 23:36 Yeah, well cause otherwise it’s just a brain drain. Like they’ll, they’ll incubate the startups there but then they’ll just inevitably lead.

Ash: 23:42 Exactly. So, but they’ve been really good at doing that. So that’s that. I would really recommend that program in terms of just getting your feet wet and you know, maybe having a shot at making a really good product because you have everything available to you to do that. And I traveled a lot and she lands beautiful country and Santiago is a great city to be in as well. So, you know, so definitely worth it.

Sean Tierney: 24:03 Did you ever make it to them and dosa

Ash: 24:05 yes, I actually did a huge road trip, uh, after the program finished and I had a little bit of time, um, before we moved to SF. I did a huge road trip, like I drove from Santiago all the way to Patagonia. So you have to cross the Andes and to Mendoza and then drive down along the route of Quanta and then keep like criss crossing between Sheila and Argentina. So probably the most beautiful road trip of my life.

Sean Tierney: 24:29 That sounds amazing, man. I, uh, I did a wine tasting tour in Mendosa when we were coming from [inaudible] to Santiago and learn incredible place, man. It’s just gorgeous.

Ash: 24:39 Beautiful. Yeah. With the Andes there. And the wines are really tasty too. Yeah, really good wines. I, um, I didn’t use to drink wine before I moved to Chile, but often when I would go out for lunch, the wine was cheaper than the waters, so I just drank a lot of wine and I started, I became a wine drinker in Chile. Um, let’s talk about, so when did you go to Lisbon? When, when did that move happen? So I had been to Lisbon a few times during my while. I was a nomad and I really loved the city, you know, the weather, the people and everything. And I thought that it was a likely spot for me to eventually move to. But you know, when you’re a nomad, you’re always thinking that, okay, at some point I’ll see this amazing place that really makes sense and I’ll just move there and it’ll be my new home.

Ash: 25:23 But often for most nomads, that doesn’t exactly happen. You just kinda keep moving from place to place. But after six years of traveling in 2017 I was like, I really need to be in a place at this point. Like I just need to have some roots somewhere. I need to have an apartment. I want to have my own couch, my own bed, you know, all those things. Right. Have a fridge full of Euro groceries and stuff like that. So I moved to Lisbon and I initially was very, very nervous about it. I was like, okay, if it doesn’t work out, I’ll leave in like three months, you know? But three months came and went and it was working out. I still traveled a lot, you know, I did, but the three months became six and six became a year. And so I’ve been living here since 2017 now. So it’s almost three years at this point of time.

Sean Tierney: 26:11 Yeah. And did you start the group when you got here as like a way to meet people or what was the motive for that?

Ash: 26:17 Yeah, pretty much. I was, so one of the things that I was, when I was on the road, I was very lonely. Like it was really hard to meet people who kind of understood what you were doing or why you were doing it. So I tried meeting people while I was traveling and tried to understand meetups and stuff like that, but nobody would really understand like, Oh, so you’re here for like two weeks and then you’re leaving like, okay, see you, you know, whatever. So when I moved here, I wanted to meet people. I also wanted to meet people who were kind of travelers but also like somehow digitally inclined. So that’s when the group was kind of good idea. And that’s how I started the first meetup in January, 2017 that I did. And it was really, um, really successful. I mean, I did it in Casa independent day.

Ash: 27:06 It was about 42 people or something like that. So I didn’t do any promotion. I just found this meetup group and I started doing it over there and a couple of meetups had taken place before this over here, but nobody had done it consistently. So I thought, let me try it. Like I live here now, so let me try and do this like every month. So we started doing it once, I started doing it once a month, but it grew really fast. Like the next meetup was like 80 people, you know? So it just kind of skyrocketed from there. And then I was like, okay, I don’t have venues big enough to have 80 people, so I need to do it more often. So I thought, let me do it twice a month, but every time 80 people would show up. So I was like, what do I do now?

Ash: 27:49 So eventually, like the summer came around and Rosanna came back to Lisbon and she was super excited that I was doing this regularly now. And she was like, Oh, let’s team up and let’s work on this together. So we started doing it once a week. So now we had a once a week, every Thursday, no mat meetup and still 80 people showed up. So, but luckily it was summer so we could like kind of spill out of bars and beyond the streets drinking. And it was just the most magical summer ever. Summer 2017 we spend a lot of time outdoors, you know, just meeting people, getting to know other nomads and building the community over here. And how big is the community at this point? Um, well on meetup it’s about 8,000 members. And on Facebook it’s about 12,000 members. So it’s really huge at this point.

Ash: 28:35 Usually at a time, of course, most of them are nomads, so they’re in and out. But at the time we have about two to 3000 people in the city. And so we have an event at this point, almost every day we’re doing like comedy nights. True story, true, true story events. We’re doing workshops, we’re doing sports events like volleyball and hikes and stuff like that. And it doesn’t matter what you post, like people will be, most of our events are free. So it doesn’t matter what you post, people are up for it and they want to do something and they want to meet other people and it’s been a great way for people to meet other people and to create community and connection in the city.

Sean Tierney: 29:11 Yeah. Well I think that’s what’s really interesting is because of the transient nature of the people that come in and it seems like every group that I’ve gone to has been, it feels like about half fixed people and half kind of new people. So it’s this really nice like reoxygenation of the group if you want to think of it that way. But then all those people are also circulating and you see faces that you know, have gone elsewhere that have since come back. And so it’s this really just a, I don’t know, fountain of interesting people just constantly circulating.

Ash: 29:38 Yeah, it’s been really interesting because what, I don’t know what, but perhaps the mind works like this, but the first few meetups that I did, like January, February, March, April, 2017, I kind of almost remember everybody who came to them even today. So sometimes people come back to Lisbon like three years later and I’m like, Oh Hey, yeah, you’re Patrick from Germany, you did this and that. And they’re like, Oh, do you remember me? I mean, nowadays I don’t remember everybody because I met so many people already. Like I think my databases, my mental databases overflowing at this point. But I remember the people from the first few meetups very well. They’re always freaked out. Like this dude is like creeping on me.

Sean Tierney: 30:16 Didn’t, uh, if I remember correctly, meetup themselves, sent some delegates here to just see what you guys are doing because it’s so successful.

Ash: 30:23 Yeah. They actually were, were quite curious about like what was going on over here and they invited us for a dinner. Uh, unfortunately I was out of town, but I think, uh, two of our organizers, so now we’re a team of 11 organizers. So we grew the team as well to handle all these events and everybody brings their own kind of, you know, twist to it. Everybody has their own passions. So it’s really nice. Some people like to do charity events, some people like to do sports events, some people like to do like productivity, like talks and workshops, those kinds of things. I personally love to do comedy. So, you know, there’s a lot of different things happening. And so yeah, the, the meta people were here and they invited us for dinner and two of our organizers went for it and they were just curious about what’s going on over here and how we’re, you know, doing so many events and what’s our revenue model? And we were like, we don’t have a revenue model, which is to a volunteer organization. And they’re pretty shocked at that.

Sean Tierney: 31:15 Well, you’re doing something right, man. So kudos on that. Uh, and I agree. Like it’s, uh, it’s very cool to see the different organizers. There are different spin that they put on events. Uh, Olivia helped us, actually you guys co promoted the charity make-over that we did here, which was very cool of y’all. [inaudible]

Ash: 31:29 Hey, that’s a cool event. I mean charity makeover is, uh, you know, when I was traveling I had this idea, um, which was, um, it was a skills like skill based volunteer platform. Like, so I, I was working with a charity and she lay for a couple of months where we were trying to build a technology product for them but they didn’t know what they wanted. And I was thinking that often charities need technology skills or they don’t need money all the time. They need people to volunteer their skills sometimes. Right. And not just skills where they’re, you’re like feeding people or something, but maybe design skills or maybe planning skills or maybe coding skills. Right. And so when I heard about charity make-over I was like, this is it. This is the way you can mobilize people to volunteer their skills. Like, cause you packaged it into this hackathon platform and it works really well because you can really like get a group of people together like a really strong team and then do something really quickly that, you know, kind of elevates a charity and their output. So I was really like, that’s cool man. That’s a really cool idea.

Sean Tierney: 32:29 Exactly the vision. Well ironically by the time this airs we will be on the boat. So we’re there. We partnered with nomad cruise for this time and they’re letting us conduct a charity make-over during the entire cruise. Oh

Ash: 32:40 wow. People and we’re, we have a pretty ambitious vision for what we’re trying to do there. So that’s really, wow. That’s amazing. Yeah. Cool. Um, all right, well let’s talk about your latest venture, the coffee shop. What, uh, how did that come to pass? Are you just buying a coffee shop? Yeah, that was uh, even unsurprised to be honest, cause it wasn’t really like I had this idea in the back of my head like yeah, I would love to own a coffee shop or some like a small like you know, this kind of business, a bar or a coffee shop at some point. I just didn’t think I’d be doing it when I’m 32 like you know, I was just kind of, so this coffee shop was across the street from my house and I would go there every day. It’s a specialty coffee shop.

Ash: 33:19 They serve specialty coffee and it’s really good and very, very reasonably priced. Great environment. Everything was great. But one day I walk in there and get my cup of coffee and they’re like, Oh this we’re going to be shutting down in five days. And I said why? And they were like, Oh because the owner, he doesn’t have time to run this business. The owner is like a famous DJ in Portugal. So I was like, okay, can I talk to the owner about the, about this? Cause I just wanted to beg him to not close it down. But yeah. So I was like, please. So I, and I mean this guy’s a DJ. So I messaged him on Instagram, he didn’t reply to me. And then I told the barista there again, like, uh, the next day, like, Oh, I messaged this guy, he didn’t reply to me, could you please ask him to reply to me?

Ash: 34:07 And so then we got to talking and then he said, Oh, I’m willing to sell it. And then I said, Oh, okay. Interesting. And then I kind of messaged my friends who live in El Contra in the same area. We have like a little chat group, which I created called the Alcantara Contra crew because it’s just people who live in that neighborhood. And we sometimes hang out together in the park or you know, do barbecues or go out for a movie or whatever. Right. Just for a walk by the waterfront. So I messaged the people in that group and I said, Hey, this cafe is up for sale. Um, and two of the people from the group messaged me and said, I’m interested in partnering with you if you want to buy this cafe now. I’ve never bought a food and beverage or bought or run a food and beverage business before.

Ash: 34:50 So the first question was, how do you value a business like this? So we had like be starting from scratch. We don’t know anything, so all right, Google it. Right. How do you value a business? We started there, right? But I mean, in 15 days we closed the deal and we bought the shop. So, uh, in 15 days we actually reopened. So what happened was July 15th, they shut down. First August we were open again. So, um, and it was like a kind of stealth mode because we didn’t know anything about this business. Luckily we managed to retain the manager. She was going to leave and we managed to retain her. That was my first challenge and then came like so many more challenges I think since, so now it’s November. Since August, I think. Yeah, my brain could have exploded at least five times with all the information.

Ash: 35:36 It’s been, you know, pumped into it, but it’s just maybe just two or two or three of like the top challenges that you’ve dealt with. Would you say? Well, staffing is a big one because when you, so I’ve worked in software teams before, I know very well how to motivate a well-paid, you know, um, employees that are working on creative or you know, coding kind of projects when you’re working in a kitchen. Uh, and it can get very stressful in there. When there’s a lot of customers, it’s a whole different ball game. How you motivate these people, how you operate. You almost have to operate it like a basketball coach. So I play basketball and I’ve had a few coaches. I mean, you know, throughout my, the history of my basketball, I wouldn’t call it career, but just experience playing basketball. And um, our coaches are pretty tough on us.

Ash: 36:23 You know, coaches are, or sports coaches are not easy on you, but if you watch any shows on Netflix about chefs, you’ll see that there’s very much the same. We’re not that kind of establishment, so we don’t have to be that strict. But I think you really need to train people constantly on how to do things. And this is something that, um, I had to learn because I was used to a very Silicon Valley kind of approach where it’s like, you know, everybody gets free time, everybody gets to relax and you know, uh, but you really have to be on the ball in a cafe kind of business. Yeah. So that’s something I learned. Then there was other stuff about, you know, um, just inventory management. How do you reduce wastage? Because we liked, we’re very conscious about our, our wastage and we don’t want to waste any food or throw away anything.

Ash: 37:06 So we try to manage our inventory in a way that we’d never have any wastage. And that takes constant attention every day. You have to know what’s coming in, what’s going out, you know, how many things you’re baking, how many things you’re selling, and you have to constantly adjust every single day based on that. Are you guys just using spreadsheets for that or do you know? We just use our eyes for action. All right. We have four cakes left. We’ve got to make two more. You know, it’s just this, it’s really, but you really have to be paying attention. Luckily we’ve trained our staff to do it at this point of time. So they’re very good at it and are very, stars are stellar. Like they are so conscious about the environment. They are all vegetarian. They’re very, you know, almost like they, they sometimes put pressure on us like the other day.

Ash: 37:48 Um, so we started avocado toast cause you know, that’s what hipsters love and that’s where the money’s at, right? But our, uh, our barista who prepares the toast as well was like really upset. And I, you know, so managing people is sometimes a challenge because you’ll see that they’re upset, you don’t know what they’re upset about and you’re trying to get to the bottom of it. And I’m like, Oh, what happened? Or you’re having a bad day, are you okay? You know, can we do something to help? And she was like, no. And then, then she started talking about the avocados and she said, I hate ordering these avocados. And I was like, why? And she said, cause I saw that there’s a mafia in Mexico that’s forcing farmers to grow up. And I was like, I could ever imagine that somebody in our cafe would be upset about that issues of all the issues that come up.

Ash: 38:31 This is one of them. But then I just looked at the avocados and I was like the carefully try and research where they’re from. And then I told her, now these are from Spain so you don’t have to worry about that. And then she was like, okay, that’s good. So it’s a lot of different things that come up and you just cannot imagine every day is different. Every day something new comes up, you just don’t know what’s going to happen. Let’s kind of go though, like in terms of a departure from a software based business, uh, I too have thought about like just a physical, in-person, lots of face to face and just, yeah, people are into business. Yeah, it’s a really cool experience for me. I’ve been learning so much. Every day I learned something new and it’s just so hands on compared to just sitting at a computer and typing that I feel I kind of feel healthier in my body as well because I’m moving around all day long.

Ash: 39:14 I’m not like behind the counter but not always. Sometimes I do help out behind the counter, but just because I’m moving around, looking at things, talking to people, talking to customers, doing other stuff, it’s just a kind of more, it’s a different approach to at least how I used to live before. At least my posture is better. I feel like I’m a bit taller even, I don’t know cause I’m not hunched over a keyboard I guess little firsthand, it’s really timely. You mentioned that. Um, I have recently learned that I have a [inaudible] herniation in my vertebrae, likely just because it’s 25 years hunched over your computer. Every job I’ve ever had has been computer-based. Um, so it’s really like I’m very much all about solving this and like mixing in more healthy like less computer time or just moving around time. Yeah, exactly. I was trying to be conscious about it the last few years that I was working with computers.

Ash: 40:03 But for some reason, once I started looking at this screen, I lose sense of time. Like I just can’t track what’s going on. I just, once I’m absorbed in it, I’m just into it. Yeah. It just sucks me. And so now with the cafe I’m kind of moving around all the time and you know, dealing with people, drinking a lot of good coffee too. I enjoy that. So that’s good. But um, I have, I have, so I don’t drink coffee and it’s one, it’s the thing that I constantly wonder if I should try to like get into it because I feel like it’s such a, you know, like the people that drink coffee have, it’s such a cool culture around it. Yeah. It’s quite a, I think it’s, people really love their coffee and we get, because we are a specialty coffee shop that’s under challenges to, you know, keep our customers happy.

Ash: 40:43 They are very picky. Coffee shop customers are known to be the most picky consumers out there. Another thing I learned in the last three months. So you know, these are all things that I didn’t know, but if you don’t get their coffee right, they’re going to leave you a bad review immediately. So in what they consider, right, quote unquote, right, right. Like we were talking like Portugal seems to like kind of a more burnt uh, air on that side of the coffee versus like how an American likes coffee. So what’s right for one group of people may not be not be another. And that’s where I think our staff is training your staff to really remember people’s names, to really remember their preferences to, you know, we really have to keep telling them, okay, you got to remember what this person likes. And they are very good at it.

Ash: 41:23 Actually. I’m really grateful to them because they work really hard behind the counter so I don’t have to, and I’m always very grateful to them for that, but they’re fantastic remembering what the customers want and what they’re like. They know immediately, like they’ll see a customer, they’ll be like your usual and they’ll just do it. And that’s just, it makes a customer’s experience so much better when they’re just like, okay, people here know me and care about me. Oh, that’s what makes it your coffee shop versus a coffee shop. I’m going to go to my coffee shop. Exactly. Got to keep them coming back that way. And I think the thing is we talk very passionately about our coffee. So we always tell our customers that this is going to be different from what you’re used to having, you know, at a Portuguese cafe. So we do specialty coffee over here.

Ash: 42:06 It might have a different type of taste profile and you know, this is how you should really make coffee. Uh, and it’s very interesting because also when we rebranded the cafe, we went through this, these questions as, as the founding team, we were like, how do we place ourselves as a brand? And it was very interesting because, uh, we did this Google branding sprint that’s available for free online if you want to look it up. And you can actually, it takes you through all these different steps and questions that help you position your brand relative to other brands in the same space. And it also helps you like with decide whether you want to be authoritative but they want to be playful or boring or serious or you know, all those different things about your brand. And so when we did this, these types of conversations uncovered a lot of, um, you know, preferences amongst the founders and how we wanted to position this brand.

Ash: 42:58 And one of the things was that we wanted to be a little bit authoritative about, you know, what we’re selling so that we can educate our customers, right? So because of that, we tell our customers that, you know, this is good coffee and you know, this is what it is supposed to taste. Like, tell us what you think. And most of the times, 90% of the times they’re like, Oh yeah, this is really tasty. So I think getting clear on those, on that brand like you, like what are the core values of this coffee shop and what do the founders want it to be. And then permeating that and making sure that the employees understand that that’s like so critical, so important and we got so much value out of it and it’s just a free thing you can find online. And it’s incredible how we were able to figure out, you know, the good news is that we were all pretty much in sync about it.

Ash: 43:44 So that was great. We pretty much chose the same things on all the questions that were there. Um, and but what’s really great is that we got confirmation of what our values are, you know, sustainability, caring about the environment, caring about customers, caring about the experience, caring about coffee, all of those things. So I think it was really useful for us to do that. Very cool. I will link to that in the show notes. So if people listening want to go through that, it’s a, we are going through a bit of this ourselves right now with Pagely the company that I work at, um, basically auditing our existing messaging and brand and all this stuff. So, uh, I’ll, I’ll probably get our team to go through it as well. Yeah, it would probably be really, it’s a, it’s, it was designed by Google ventures for the companies that they invest in. So it’s available on I think the Google ventures website. I’ll probably find it over there. Very cool. Well actually I know you got to get back. You just hired someone so you gotta go train.

Sean Tierney: 44:32 But there’s one last part of this interview that I’m going to run you through. It’s called the breakdown. So are you ready for the breakdown?

Ash: 44:38 I’m sure. I don’t know what it is, but let’s do it. Okay.

Sean Tierney: 44:44 What is one book that has profoundly affected you?

Ash: 44:48 Well, recently I read this book called the untethered soul and it’s about, it’s mostly about spirituality and the self. And I was going through a rough patch like earlier this year because of a breakup and stuff like that and I was kind of trying to figure out, you know where I stand and this book really helped me understand to be more accepting of things that come your way. And it was really strange because to be honest, I realized that most of my life was lived that way. Like things just came to me and I just wrote that, you know, wave and something else cool happen and something else really cool happened and you know, yeah, I think it, I think acceptance was basically the message that I got out of it. But this book really breaks it down beautifully for you. Like you just, it kind of just makes sense.

Sean Tierney: 45:32 Yeah. Michael singer, I 100% agree. I read, I actually heard his interview with Anthony Robbins on his podcast and just phenomenal interview. I’ll link that as well in the show notes, but that got me to read the book and 100% agree. It’s a, it’s a game changer for sure. Definitely. What about, what is one person you would love to have dinner with? Can be living or dead.

Ash: 45:52 Huh? Interesting. I mean there’s so many, how do you pick one? This is like, Oh my goodness, the Vinci, you know, that guy was the, he was thinking like, you know, in a different way for his time. He was doing all kinds of stuff. He was just, you know, really out there and of course persecuted for it. But you know, I mean we talk about, you know, abstract thinking and out of the box thinking and design thinking and all of these things and that guy did all of it at once. You know, he was able to do all of those things at once. That’s genius. Yeah.

Sean Tierney: 46:25 Who a corollary to that, do you think there’s a DaVinci of our day who’s under represented who

Ash: 46:30 underrepresented? I mean I find it hard to imagine like there’s so many. I think now we suffer from information overload so it’s really difficult to narrow down like one person who might be that way. Of course you have like game changers and paradigm shifters, like Elon Musk or bill Gates with his charity initiatives and even stuff like the giving pledge that bill Gates and Warren buffet are in. And you know, those things were never are unprecedented. You know, they never happen before in, in at least recorded history. So those are pretty big game changers but still DaVinci seems like he was a man with few resources but great ideas and a lot of outputs. So I, I don’t know if you have somebody like that right now, uh, what is one tool or hack that saves you time, money or headaches, tools? There are plenty. Um, I, you know, I, I went through phase where I was into a lot of productivity enhancement and you know, finding ways to be more productive and stuff.

Ash: 47:28 I did that for while I tried all kinds of different tools, but ultimately I realized that discipline is the best tool and it’s free. And so I was like, you know, discipline routine and just forming a good habit is, it’s, you cannot replace that. It’s just, and so I decided to, I’m a morning person, so I’ve been, so I bought a coffee shop. Now I wake up every morning and it’s great. So I do things in the morning and it’s great. And I think there’s a lot that could be said about, you know, uh, enhancing productivity. I’ve, I’ve done a few like simple techniques, like being really focused through meditation and stuff like that. And that really helps me also free. I’m a fan of free tools. Is there any form of meditation or how did you learn the skill? So I kind of got on the meditation bandwagon at about the same time as Headspace came out.

Ash: 48:20 I did that for a bit and, but I couldn’t really stick with it because that guy, Andy, his voice would irritate me after awhile and I just was like, I liked it initially. I loved his voice for like 20 hours of it, but then I was like, okay, like I can’t do this anymore for some. But that was the first version of the app. So maybe they changed that. I don’t know if it changed multiple speakers. Yeah. But I, I can sit and meditate quietly now cause I trained for that. And also there’s this Isha cria form of meditation, which I really enjoy. Uh, you tell me what it is. Only two. Yeah, it’s like a, it’s like a specific school of meditative practice and yoga practices and stuff like that. I came across it also in one of Michael singer’s books. I think the surrender experiment is where he talks about this form of meditation and that’s how I got into it. And that really helps me improve my focus. So usually before a comedy show, I do that and then I’m just in zone. Yeah. That’s awesome. All I will lead to that and surrender experiment is actually on my list. Uh, I want to read that one next. That’s a good one. Um, okay. Here’s the tough one. What important truth. Do very few people agree with you on?

Ash: 49:30 I think I, so it follows from my experience in the last couple of years and also with, you know, I think a lot of people think about controlling outcomes. Like a lot of, a lot of people are all about, you know, controlling how they live their lives and they want to customize everything they want to make. Really. They want to make the right choice all the time. But this leads to a lot of, you know, decision fatigue. You’re always trying to figure out what’s the choice that maximizes my happiness or whatever your end value is that you want to maximize. Whether it’s money, happiness, love, fame, whatever it is. And I think I just started living in a way right now where I just kind of take each day as it comes and accept whatever happens and I’m really happy these days. So I think that’s something that really changed was the game changer for me.

Ash: 50:19 I’m not so good at explaining it to people, so everybody always disagrees with me on it. But that’s what it sounds like very much the message of like surrender experiment. Exactly. Yeah, exactly. So that’s how I’m trying to live my life. I wasn’t a stoicism a lot as well, which kind of says the same thing. It talks about, about circle of control and all these things, but somehow when I read these books and the message just rang true to me through them and I just was like, I’m going to try and live this way. Let’s see what happens. And I’ve been doing it for like a couple of years now and it’s really helped me live better. And that was the cafe as well. The cafe just showed up on my doorstep literally up for sale. My favorite coffee shop. Let’s do it, you know, and here we are right now.

Ash: 50:58 So there you go. I love it man. All right, last question. So if you had a time machine to go back to your 20 year old Ash self and give yourself any bit of advice, what would you say? Uh, ironically I would say don’t know, mad for too long. Like I think, uh, it’s, I think I pushed the, I pushed it too hard for too long. I was too tied to being a nomad and I couldn’t give up that piece of myself to be honest. If I ever moved to Lisbon after three or four years of no matting, it would’ve been fine. Really. I didn’t need to go the extra two years. Yeah. So I’m glad you bring this up because we actually were, I wanted to talk about this notion you mentioned upstairs a little bit ago about like making your identity too closely coupled to nomadism and how dangerous that can be.

Ash: 51:45 Yeah, I mean I, the reason, I mean I was tired, I was lonely. I really wanted to have like a house and then, you know, just the general set of activities or routine that I could do every day for like a consistently long period. I wanted to have deeper friendships and connections with people, but because I was like, no, I’m this nomad. I have the freedom. Why should I give up my freedom? You know? The truth is that even if you go and start living in a place, as long as you stay location independent, you still have the freedom. You can still leave when you want. Yeah. But I think for me personally, it kind of shifted slowly over time. Like I moved here in 2017 and I still felt like I was a nomad and they needed to travel a lot and I did it.

Ash: 52:25 I spent almost six months away in 2017 in 2018 I perhaps spent four months away, but in 2019 I’ve pretty much been here the whole year saved for maybe one month or six weeks or something like that. So I’m more and more non-numeric. Like I wouldn’t even call myself a nomad at this point of time. So I think we’ll thankfully, because we need someone to run the Novak group. Yeah, exactly. Absolutely. I got, I gotta be here to run the group and to have all those events connecting fearful. But I think what I really learned was that I waited for too long to move here. I should’ve just moved here in 2015 or 2016 you know, and it would have been fine. Like I could’ve always become nomadic again and I can still do it. I mean, maybe not now when I have a cafe, maybe in a couple of years I’ve been stable, but you can still do it. So it’s not really you gotta you gotta be aware of what you need in that moment and not be too worried about how you see yourself or how people see you. You just have to know what you need and just do that because I think it’s really important to take care of yourself. I think that’s amazing advice. I think

Sean Tierney: 53:25 what’s ironic here is like I run a nomad podcast, so in some ways my identity is now coupled to this, but I don’t know, there’s a phrase that I like. It’s a strong opinions, loosely held. And so I reserve the right to change and say, Nope, I think I’ve gotten what I need. I don’t know about as I’m done for awhile. But yeah, I think that’s, that’s a very good advice and something that for whatever reason in this world, people seem to adopt the identity and then be unable to relinquish it. So

Ash: 53:54 I think that’s, uh, that’s the same with any big change in our lives. Right. And I think it’s just, um, also I think with nomadism, um, some of us sometimes feel like if we give it up, we fail somehow. And I don’t think you should feel that way because nobody says it’s forever. Like, you don’t have to do this for the rest of your life. You can do it for as long as you feel comfortable doing it, then stop doing it, then do it again. If you wanna you know, it’s all up to you. Independence means, yeah, you can be somewhere fixed and still be location independent. Exactly. And then just leave after a year or six months, once you’re feeling refreshed and energized and, you know, just do it again if you want to, but don’t push yourself to the point where you’re just kind of, you know, in a bad state of mind. Yeah. Yeah.

Sean Tierney: 54:38 Well, I think that’s amazing advice. Ash, I’ll let you go. I know you’ve got to get back to the coffee shop, but, uh, how can people connect with you on social media or find your coffee shop? Where do we send them?

Ash: 54:47 It’s Silva Lisboa on Instagram. Um, you can find me there, or a lesbian digital nomads or lesbian comedy. I’m all of those people, like all that stuff in the show notes. Ash, thank you so much for taking the time. Thanks a lot, Sean. I was pretty excited to be here. Cheers. Cheers.


Sean is host of Nomad Podcast, author of the Nomad Prep eCourse to help others successfully transition to the nomadic lifestyle. Sean is also founder of Problemattic, a global movement to mobilize knowledge workers for good. Read more from Sean on his personal blog or his business blog.

View all posts

Nomad Podcast is a series of conversations with nomads, founders and domain experts to help get more people unstuck through transitioning to a nomadic lifestyle. Add your email to get special access to private AMA sessions, pre-release products and other VIP shiz.