Matt Bowles:   Hey everybody, it’s Matt Bowles and my guest today is Ali Greene. She is an expert in organizational behavior, human resources, and people operations. For the last decade, her passion and focus has been on the future of work as more companies are opting for nontraditional work environments. She has consulted on people ops for companies ranging in size from early-stage startups to 200 plus employees. She’s currently the director of people ops at DuckDuckGo where she oversees the overall employee experience and is responsible for intentionally crafting how business and operational decisions impact a company culture as an internationally distributed company. At DuckDuckGo, she implemented a new hiring process strategy that helped the company grow over 80% in two years with a focus on gender diversity. She has also been a digital nomad since 2016 and has been to 30 different countries. She is passionate about learning through travel and the impact of remote work on nomadic communities, personal relationships, communities, and society at large. On a personal level, she is obsessed with seeing street art around the world. She helped paint a mural in South Philadelphia, and she was once a member of an ax throwing league. Ali G., welcome to the show.

Ali Greene:   Hi. Thanks for having me.

Matt: Awesome to be here with you. Let’s set the scene for people. You and I are currently in Nairobi, Kenya, and we are drinking a bottle of Pinotage from Stellenbosch in South Africa.

Ali: Well, if you’re going be in Africa and drinking wine it better be from South Africa.

Matt: Indeed the preeminent wine region of the continent for sure and Stellenbosch, their reputation precedes that particular region, and this is a particularly nice Pinotage. I feel like this is the best one we’ve had.

Ali: Yeah, I think we pause for a sip now. Right?

Matt: Yeah, I think we pause for a sip or I’ll talk and you take a sip, and then while you’re talking, I’ll take a sip.

Ali: Cheers.

Matt: Cheers to you. You and I have been here in Nairobi for a month, which has been totally amazing. It’s my first time. I’ve been to South Africa, and I’ve been to North Africa, but this is literally my first time in between. We have been on safaris, and it’s just been, for me, a really special month.

Ali: Yeah. It’s been awesome to be here. I think one of the things about traveling and working remotely is sometimes even though you’ve seen so many places, it’s nice to get out of your comfort zone. I am one that shies away from big cities, and Nairobi is the biggest city you can get in Kenya. So coming here thinking I would hate it and then really turning my opinion around in a month and sad to be leaving this weekend has been incredible. Part of the reason I like to travel is I’m constantly surprised and constantly learning things about my likes and dislikes.

Matt: It’s been really amazing. I have been really touched and moved by a lot of the people that I’ve met here and the interactions that I’ve had here and it’s just been incredible not to mention the connection with animals and nature. We went on a safari to Masai Mara, which is one of the preeminent places to do a safari anywhere in Africa and it was, for me, just a really special experience. I had never done a safari before. So, it was my first time being that close to those kinds of animals in the wild and just literally seeing from the porch of our bungalow elephants, wild elephants just roll up and just start eating branches off the trees like right from the porch of our bungalow. That was unbelievable to me.

Ali: They were upset they weren’t invited to our dinner.

Matt: I guess they were but totally amazing and then seeing the lions, and then buffalo, and all of that kind of stuff was just a really special thing so all in all an amazing month for sure. Now, you and I also though, just to contextualize for people, have known each other for probably a little over six months now. We initially met in Da Nang, Vietnam earlier in the year.

Ali: Yep, that was a pretty cool experience too because I remember thinking when we were meeting up again here in Nairobi that we probably only had about three deep conversations in the month that we were in Vietnam together and so this month just looping back up is one of the awesome things about nomad communities.

Matt: It’s been amazing and I know you found out about this because you were in Da Nang and you were like, what are you doing for the rest of the year? I was like I’m going to Nairobi, Kenya, and you were like, oh really. Can I get the details on that?

Ali: Yeah, thanks for letting me tag along.

Matt: Again, that’s one of the really cool things about world travel and meeting people, and all that good stuff. Amazing. Let’s start with your story. I have to begin with this ax throwing thing. Tell me what an ax throwing league is, where that came about, and maybe start a little about where you grew up, and then how you got involved in this thing.

Ali: My involvement in joining an ax throwing league I think is really symbolic of my life in general. When I first started out being nomadic, I started to test the waters of time inside and outside of the US. I would go and I would have these amazing travel experiences six months of the year and then I would move back to Philadelphia, which is where I was based the last time I had a proper lease or a home anywhere. But I found pretty quickly returning back to my normal life left me very uninspired. So there are a few things that I did to keep the momentum and of fun, and excitement, and adventure that happens when you’re traveling in my stable environment. One was dying my hair. So, I’ve had crazy hair colors, blue, pink, purple, etcetera, and the other was every time I would return to the United States, I picked up a new hobby. If I could one day in the future, I’d love to consider myself a professional hobbyist and just live a life of leisure and always be diving into weird, cool, new things and ax throwing just happened to be one of the things. When I was going back for a summer in Philadelphia, that came onto my radar and I was part of the inaugural league. There had never been a league in ax throwing in Philadelphia before, and I was like if I can be the first person to do this, and this thing is super weird, then of course I want to do it. Basically, it’s like darts but with an ax.

Matt: So how does it work, you have a target, like an archery-type situation but you’re wielding axes and throwing the axes at the target?

Ali: Yeah. There’re two size axes. You have your basic hatchet and that’s what you do for normal play, and there’re targets similar to archery or darts where the closer you are to the bullseye, the more points you get. In ax throwing there’re also targets kind of off to the side that are harder to hit and more points and so that my game was always trying to get those hard to hit bullseyes instead of the regular ones. So, you play with the hatchet, two handed overhead swing and throw and in the case of a tiebreaker, they bring out the full ax, long handle, really heavy, and it’s still over the head maybe this time, close your eyes and hope for the best and throw. But it’s pretty fun and it’s definitely like a cool interesting hobby to have learned.  

Matt: That is amazing. Can you talk a little bit about how you decided to get into the digital nomad lifestyle and maybe a little bit about your background, upbringing, and then what sort of led you to make that decision for yourself?

Ali: Yeah. Not to be too therapy session on everybody here, but the more that I travel, the more I pinpoint the origin story of me being nomadic to my middle school years. I was born in Michigan and grew up in South Florida. When I was in South Florida, I actually ended up going to four different middle schools in the span of three years. The reason for this was one, because of how public schools are structured there where you have elementary school in some cases up to grade four and for some cases it goes up to grade five or six. So, it really varies there. I went to three different schools while I was in Florida. One of them was a math and science school. Then I went to a normal public school and halfway through my eighth grade, in the winter, my parents were like oh hey, we’re going to move back to Michigan now. That was middle school No. 4, and it’s one of those things where looking back, you realize that that led me to believe that change was always going to be a constant in my life and the situations and the new surroundings and learning how to be adaptable was something that I had to learn by doing in the really formative years of my life. I didn’t quite notice the trend there until after university and once I graduated, I did this thing where I thought I was going to be really successful and live this glamorous life so of course I moved to New York City, but I was getting paid in bagels in an internship and I couldn’t afford an apartment anywhere so I just sublet hopping around time and not putting down roots in any one apartment. That turned into a year of life in New York and then I moved to DC for another job opportunity. That was the first time in my adult like, and probably my life anytime, when I consciously tried to make the decision to put down roots. I decorated this apartment and it had this nice exposed brick wall and a kitchen that I would pretend was like a TV studio kitchen and it felt really adult and [inaudible] [00:11:12]. I lived there for a year and a half in that apartment and then was like, oh wait. Is this what I want? I don’t know if this is what I want. So, another year and a half later I moved, sold all my Ikea furniture and moved back to New York, rebought a bunch of furniture, and was like nope, this is the place. This is the place I’m going to put down roots. I swear between my life in DC, New York, and Philadelphia, I’ve put together and then sold the same Ikea dresser three times. It got to this point where like if you keep doing the same thing and expect different results, then maybe you’re crazy. So, I had to take a deep look at myself and be like, maybe you aren’t supposed to live this traditional life. Maybe living this life is crazy for you. You’ve never tried not having a place, and not putting down roots, and not building that Ikea dresser. That’s when I decided that maybe a nomadic life was for me.

Matt: You know, that’s really interesting that you say that because I as well moved around a bit growing up and so a lot of times when people are like where you are from, that’s always a tough question for me to answer because I’ve never lived anywhere my entire life for longer than seven years. That’s my longest stretch, and so I just pick one of the seven year spots. I usually pick the last spot that I lived for seven years, which was LA and I say LA; but I also lived in DC for seven years and went to grad school there and had an amazing experience there. I also went to middle school and high school in Buffalo, New York and I lived there for seven year and had a great experience there. So, I have a lot of different connections and different roots and I agree with you, that I think moving around growing up and developing those skills, as hard as they sometimes seem at the time when you’re a kid, and you don’t want to leave your friends and you have this sort of stability. But kind of being forced by forces more powerful by you, like your parents’ job change or whatever, and going to a new place and realizing, you know what, there’s also cool people here, and I personally have the skills to make friends and to establish myself here and to develop a nice experience which is different from my old experience, but it’s different in really cool ways. So, when you develop that confidence growing up, I think gives you also a little bit more confidence to be able to travel, and to know that you can go to new places, and experience new things, and you’re going be okay, and you’re going figure it out, and you can make new friends, and all that kind of stuff. So, I have a similar experience and a number of people that I’ve talked to who are nomading also kind thing, moved around a lot. So, I agree. I think that has a lot to do with it.

Ali: Yeah. It’s funny too. Sometimes I try to have this internal argument with myself about why people nomad and it’s this nature for nurture argument. I know for me, definitely moving around that much and changing my environment and situations played a role in this. But not that I’ve been doing it for a few years, I get a question a lot from people that are what do you love about traveling or how exciting is it that you travel, and sometimes I sit back and I’m like, well, I don’t know if I actually love it or that it’s exciting. But one thing I do know 100% for sure is that it feels really natural to me, and if you think about, I have no degree in science, but human evolution, there were groups of people that lived nomadic lives that found food and shelter and there were groups of people that put down roots and built communities. I wonder how much of that transcends to 2018 now that we have technology in place to let us live this lifestyle that might be more natural for some humans.

Matt: Actually, maybe you can talk a little bit about that because one of things that is amazing to me to think on is I left the US and began nomading full time in 2013. In 2013, when I began doing that, I was thinking to myself, oh my goodness, how amazing it is that we have Airbnb because Airbnb allows me to go think about any place in the world, any country, anything in the world, and book a nice apartment for exactly the number of days that I want. It can be for a couple months or whatever. Now, prior to that, you’d either have to get a hotel or you’d have to around with a real estate broker and find an apartment and a short time furnished apartment, good luck in some cities doing that. So I was like, wow, Airbnb is there, Uber is here. I can get around cities. I can fly around. I can have places to stay. Isn’t this amazing? Ten years ago, you’d never be able to travel this and lo and behold, since 2013, the evolution of the nomad ecosystem between then and now has just been this extraordinary proliferation of companies coming into this space and trying to cater to the evolution of this lifestyle. I know that you are really immersed in a lot of other different options and lifestyle infrastructure choices that are out there for nomads so maybe you can talk a little bit about that, you can start out with that here, for people that are either thinking about the lifestyle and thinking about getting into it, or maybe people that are already there. What does that look that? What are the choices for people that want to travel and work while their traveling and have this be kind of a longer term lifestyle choice?

Ali: I think the evolution of the different communities that exist is really a case of nothing is actually new. Things are just new again and so what technology has enabled for this lifestyle is to find different outlets more easily that will help set you up for success. So, if you need community, and you have this need for affiliation with others, previous that could be pretty isolating going to a new city, forget about digital nomadism for a second, but just like moving to a new city or traveling to a new city, how did you interact with the people and the community there. Then you have things like meetup.com and Facebook groups and things like that that connect you at a social level. I think those are still great outlets to tap into as a digital nomad but then as you said, there’s now, I don’t know if it’s a movement, or a culture, or a community, or an industry, but all these things that are now supporting people specifically that are dedicated to working while traveling. That’s quite different than other groups of persistent travelers, backpackers I’ll use as an example because I did backpack for quite a bit of my life in my 20’s while I wasn’t working and now I’ve experienced this life while working. When I first started out, I only knew that backpacker community. Social aspects in life are very important to me. So when I first started doing my digital nomad life, I would seek out hostels that had private rooms, and I felt like that would be the best of both worlds because I could go to sleep early if I knew I had to work up for a work call the next day. I had enough privacy to focus on my job, but I still tapped into this social environment. The problem I found there is the culture is a little bit different. When you’re joining a hostel, you’re meeting people that don’t have necessarily the same level of responsibility as you do and there’ll be all this temptation for really fun things going on or people will be more fluid and in and out of the hostel. That was my first year of nomading. Over the past three years, I’ve seen the landscape of this totally change. I’ve stayed in co-living places, which someone recently told me they think is just a term for working from home in an apartment with roommates, which is true but it’s so much more than that because it’s about being really intentional about connecting people that share similar life values and also similar flexibility in their work and creating an environment that, of course, has the best WiFi available to you in a city, and a place to sleep, and shower, etcetera, your basic life amenities. But what I think is really special about these co-living places is that they’re connecting people to each other in a social way but also connecting people to each other to support the goals of whatever it is they’re working on whether it’s through Mastermind sessions or skill sharing and just the amount of learning you can do as a human while staying in these places is beneficial for you and whatever type of work or business you’re trying to grow. So those places are really special to me, and what I love about them is that you start to see people return back. So, the community grows and networks, and you’re meeting people that’ve been three, four times, and you’ve been there three or four times and maybe your paths have grossed and maybe they haven’t but you all start to know each other in a digital way than in a real life way. Then the people that run these spaces are usually tapped into the local community so you get the benefit of both worlds. You get to travel and you get all this newness, but you also get local expertise.

Matt: That’s awesome and you’re going back to one of your favorite ones next month, right? Do you want to talk about where that is and why you love it?

Ali: Yeah. I’m going back to a place called Sun and Co. in Javea, Spain for their third anniversary. I’ll be there in two week, and what I really love about them is first of all it’s in a place in Spain that you would not necessarily choose to go to. It’s not Madrid. It’s not Barcelona. It’s this really cute charming town about two hours away from Valencia on the coast. They have farmer’s markets on Tuesdays where I’ve stumbled through my terrible Spanish to order cheese and olives. You just get to be immersed in Spain. I’m obsessed with the town, but there’s from what I can tell nothing too special about it. The weather’s great. It’s right by the ocean. There’s good hiking. There are enough restaurants where you can get out of the house. But what’s really special about is the way that the leaders of that community engage people to have a more meaningful connection right from the get go. So, the first thing you do in that environment is have a family meeting where everyone talks about, both professionally and personally, what they’re hoping to get out of their experience there and as a community, you decide how you’re going to support each other throughout the week whether it’s encouraging people to wake up early for a morning hike and then having coffee and watching the sunrise or teaching people, and this is something I did last time I stayed there, a lunch and learn session on productivity and time management.So you get really, again, all this support holistically in your life where when you’re not traveling and working remotely, you get it in a very fragmented way. You get the social support and emotional support, you get professional coaching and informal growth through others so it’s just a really cool experience to be a part of and I think it’s great for people both that have never traveled and worked before because you can watch other people do it and you have sort of a formal structure and all the logistics are taking care of for you. I personally love logistics so that’s not the motivation for me to go there, and I’ve been doing this now for three years and I’ve traveled alone, I’ve traveled with groups, I’ve gone to co-living places and for me the most special thing is having this outlet to constantly learn from others and create deep, hopefully, long-lasting connections with other people in what could be considered a very transient type of life.

Matt: Yeah and I think there’re a couple different formats too for the establishment of community in terms of the nomading. One is the sort of fixed co-living places, which as you said people can return there and they can stay for as long as they want, and sometimes people will stay for extended periods or they’ll come back a number of times as you have with Sun and Co. for example. And then the other major model that’s out there now, which you and I have also experienced together, which is actually what we’re doing now, is these companies that have set up basically these sort of roving communities where you can actually move from city to city, country to country, continent to continent, with the same community of people over a period of time. So you’re retaining the consistency of community and of the ability to build those relationships and stay with the same people, but you’re actually moving and roving as a community. The companies that sponsor these types of experiences are setting up the accommodations and the co-working space access so you have the ability to work in an office with 24/7 access and WiFi and everything else in these different places and you’re able to go to experience different places instead of staying in one place. We mentioned that you and I met in Vietnam and that was in a program called Hacker Paradise which uses that model and we’re now in Nairobi with a company called Wanderist Life which also uses that model. They’re in a single place for, depending on which of their programs you use, Wondrous Life is in a single place for anywhere from one month to three months at a time. Then they go to another place. Hacker Paradise is usually in one place for about six weeks at a time and then they go to another place. You can go to a lot of these programs for a shorter period, like a month, or you can buy a 3, 6, 9, 12 month package with them and go for a more extended period of time. So, there are a lot of different options in terms of lifestyle structure and different people can customize to what their preferences are.

Ali: Yeah and I love that because you really are seeing different people have different travel styles. One of the things that kind of shocked me about this life when I first started out, and looking back it was pretty naïve, but I just assumed that everybody that was as passionate as I am about traveling, and working remotely, and living this life would then have all the same values and interests that I have. What I’ve learned, obviously, is that everybody’s human and everybody’s different and so what’s really cool about the growth of this type of lifestyle is there are so many ways to get support that can match your different needs and you’ll start learning about how certain nomads are different than others in their value systems, needs, and interests. I think you and I are a little bit of an example of this. I think you proactively seek out as many of these communities as possible and you really go through these experiences and dive in wholeheartedly. For me, that’s not really my approach. My approach is I really like to strike up not having consistency, and so I like to weave in and out of programs that are more formalized like the ones you mentioned where I can go to a place I would never have considered going to alone and immediately have this support system and be able to really push outside my comfort zone like what I’m doing in Nairobi and also in Vietnam. Then I like to retreat and take some time along and just really focus deeply on my work and check in with myself and create space to just be alone. Then what’s been awesome now about being a digital nomad and going through programs like this and living in cities alone is informally, I now have real life friends that are digital nomad friends where I create my own meetups and there’re levels of informality and formality in the ones that I create for myself and my friends to make sure that even though I’m from a different country than someone or even though I only met someone briefly through a travel program, if I want to invest in them as a person and build our relationship that there’re outlets to do that throughout a given year.

Matt: Can you talk a little bit more about that in terms of what you did in Servia and what you’re going to do in Mexico City and just some of the details about these initiatives that you’re involved with?

Ali: Yeah. The initiative I led with a few friends in Servia came out of kind of like one of those classic funny stories where I was celebrating Christmas in Finland in this snowy cabin, except global warming there wasn’t that much snow but for the sake of the story it was snowing a lot because I think that sounds more scenic and festive, but a friend and I decided every day we were going to go for a walk. This is one of those friends where we would just have these intense conversations that would turn into these hypothetical stories and games and we played a version of if you were stuck on an island with someone who would you want to be stuck on an island with. We talked about all the people we had in common which was a pretty small list because we had just met a few months before, and through that conversation, we were like, wait, we actually would like to be, not stuck, but chose to be in a place with these people again and can we do that. What would that like if we organized something or least became a catalyst for people to get together, would they want to? So, what started off as just sort of a joke turned into, wait, these people are really interesting. They have a lot of great things to say. We share similar perspectives on some topics but completely disagree on others, and how cool would it be to spend time with them and really dig into topics that we feel passionate about because while I love that digital nomads are really free spirited and adventurous, and they’re the first people I think that will raise their hand and be like I’m in for karaoke, or cliff diving, or partying, or anything cool because digital nomads are cool people, sometimes what you miss is like sitting on your sofa with a glass of wine and having a really geeked out conversation about societal norms or have like a really interesting conversation on the dynamics of relationships in life. So, we decided to invite a few friends, and friends of friends, to get together specifically to have deep and meaningful conversations on a regular basis while co-working and living in the same city. So, that’s what we did in Serbia. We had about 12 people come, and we’re going to do another informal gathering of friends and friends of friends that just want to have really interesting conversations over the course of a month. Maybe we’ll also cliff dive or something, but probably not.

Matt: Yeah, I think it’s amazing about the way that you can curate intentional communities to have meaningful experiences with select communities of people. That, I think, it amazing because as you travel around and you connect with all these people, there’s different types of peripheral similarities that you all have. Like you all are making choice to be in this place, in this context, in the same program or whatever it is, for the same period of time. So, there’s some commonality that led you all to this decision. But within that group, there’s a lot of diversity usually of people, different types of people, and all that kind of stuff.  So then to be able to curate specific, niche, intentional communities that want to come together to connect on a specific level and since you’re all nomads anyways, you’re like let’s go pick a cool epic location and factor in some cool experiences but then also have these deep connections and discussions about these other things. I think that’s pretty amazing.

Ali: Yeah and for me there’s a time and place everything. I don’t think I could have that level of conversation every day. I think my brain would explode. Sometimes I really do just want to let loose and test my vocal range in karaoke, which I know you will not appreciate as much.  Or go for a hike, or go wine tasting in Cape Town. What I also love about this lifestyle is the diversity of people you meet but also the diversity of experiences you can choose for yourself. I feel like for the first time, probably in my life, I have complete control over where I’m spending time and why, who I’m investing in and why, and how open I’m letting myself be to new people and new experiences, and learning from them.  Whereas if I had just lived in one city or a few cities my whole life, a lot of that would be based off of that would be based off of circumstance. So, this life for me just shows so much proactiveness about pushing your limits and pushing your boundaries and learning about yourself and cultivating self-awareness, and a lot of that comes from the mirrors of the people and places you choose to be around.

Matt: Totally agree, and the ability to control that, as you said, is really the key, right?  Empowering yourself with the options to choose location independence, where you go, but then specifically the types of people that you spend time around and the type of environment that you create for yourself and what you’re doing with your spare time in addition to your work time, and how you’re doing that and choosing places where you can really engage in things that are meaningful to you outside of work and then to engage in people. That’s kind of amazing, right? That’s one of the aspects of digital nomadism and the ability to control your own environment that is really extraordinary. It’s not just place. It’s also people and it’s also experience.

Ali: Yeah. I think 100%.  Having control over your own life I think is what most people strive to, and I do recognize that there is some privilege in being able to have that control through the means of digital nomad life. But I think that it just really speaks to human motivation and happiness and if you’re the person that’s in control of the surroundings you put yourself in and you’re unhappy, then you have the control to change it as well. I just think that’s really powerful in terms of holistically, not just professional, not just personal, but holistically how you choose to live your life is every decision you make is a proactive intentional decision.  

Matt: Definitely. Let’s talk a little bit about what you enjoy doing and as you select the places that you go, and maybe talk a little bit about how you structure your lifestyle right now. Over the last couple of years in your digital nomad lifestyle, how have you chosen to structure your travel? How fast or slow do you travel? How do you choose your locations?

Ali: Those are really good questions. This is something I’ve been really interested in lately because I like to take check on myself every few months and start to create space for more self-awareness. It had been a while and someone asked me this question and I didn’t have an answer. So, then I started asking all my friends. I have a friend who chooses locations based off of movies and books that are really inspiring to her, and I just think that’s pretty awesome. Then I realized for me, I had been choosing places I think based around people more often than I thought, which was really eye-opening to me. Why I’m glad I made this realization is because digital nomadism is such an independent lifestyle to know that my decisions were based off of when I needed time to spend with people and when I needed time alone to recharge was an interesting thing to learn about. So, definitely I like to keep myself open when I’m traveling. If I meet really amazing people that I want to spend time with, I want to leave my schedule open enough to spend time with those people in different people and that’s something I’ve done over the past year. I see the same people now every few months and that feels really good and it feels like we’re starting to develop very deep friendships. This is something I had to get over too a little bit when I thought I’m going to live this digital nomad life, for me it also meant not going back home that often, but also I choose to go back to the United States when there’s something really meaningful going on in somebody else’s life and I want to show up and be there for them. So, I’m going home in a few weeks to the US because a good friend of mine is getting married. My nephew is five and wants to dress up for Halloween.So again for me, this lifestyle is all about being able to invest of people. Outside of that, I tend to travel a lot slower now than I did the first year I traveled. My preference would be to stay in one place for about three months although giving myself an easy out if needed. I tend to skew more towards smaller cities or bigger towns, things with access to my hobbies and interests. So, I’ll only want to be in a big city if their start art’s awesome. Other than that I need to be by water, and hiking, and bike riding, and opportunities to get away from my laptop and get away from work and be in fresh air to detox.

Matt: Let’s use that to talk a little bit about our shared passion for street art. Can you talk a little bit about what it is that you love about street are, why you’re so passionate about it, and share a little bit about that?

Ali: Yeah, definitely. There’re so many things I love about street art. I think at its core, its evolution as this alternative breaking the rules, sort of I do what I want to show my independence, culture is something that really speaks to me. The only time I’ve ever gotten in trouble in my life, I love this story, I was in high school. We weren’t allowed to drink juice boxes in the hallway because the high school was fancy and there was nice carpet. I was a straight A student. I was really involved in my high school. I worked at our school store. I took AP classes. I was a good kid. I was the good innocent kid. I followed all of the rules. I remember one day I was going from my independent study hour to another class, and I was really thirsty and I was drinking an orange juice in the hallway. The principal comes up and he’s like you aren’t allowed to drink this juice in the hallway. I just kind of sat there and was like I’m being respectful of the school. In my mind at the time, I was an adult. I’m not going to spill it. I’m just trying to get from one class to another and drink something. I was thirsty. So, I go and I throw it away. I was like okay, no problem. I need to get to class now, and I thought that was going to be the end of the story. The principal was like you can’t just throw it away. You broke a rule. You need detention or something. So, I got sent to the principal’s office and I was like, this is so silly. There’re people cutting classes. There’re people doing other things that I won’t mention that go on when you’re a teenager and I’m just drinking a juice box. Tying this back to why I like street art, it was like there was this establishment and this rule that I didn’t believe was right and I just wanted to express myself and take care of myself. What I love about street art is this thing that started out to be really rebellious has blossomed into this really beautiful thing that’s actually helping communities. So these people that used to be seen as the trash of communities because they are tagging and graffiting the wall, are people that are just finding ways to express themselves and to share passion around an art form that’s really beautiful and really difficult to create. All these intricacies on how you get recognition and respect as a street artist up to a point where now corporations and government are paying people to make these beautiful murals on something that used to get people in trouble is something I really identify with because I think that if you’re breaking a rule for the better good then you should break that rule sometimes. If you’re turning a place that used to be dangerous and dirty, and scary, and you’re putting up beautiful things for people to look at, not only are you transforming physical space but you’re transforming how the community interacts with each other there and you’re bringing accessible art to everybody. I just get really excited about that.

Matt: Can you talk about our first street art experience together in Vietnam?

Ali: I can. This is one of my favorite days in Vietnam. There is a town maybe two hours from Da Nang where we were living that literally used to have nothing. It was a fishing village, and it got overshadowed quite quickly by other small towns in the area, Hoi An to be very specific, that was getting a lot of attention in tourism. So, this fishing village didn’t really have anything to connect the community with each other and also just to bring in other eyes and visitors to the outskirts of what was starting to become a really tourist driven destination. So they created a partnership with, I don’t know if this is true, but I think South Korea. In another Asian country, they created a partnership with them and brought in artists who create murals all throughout this small fishing village to beautify it and to make it a place where despite your poverty level and despite the change of the other cities around you to stake a claim that they had something beautiful show and that art belonged to everybody. So, we took a two hour cab ride to get there. I think we only spent maybe an hour walking around. I have probably 150 pictures of just these amazing, beautiful and different artistic styles of murals in this town that otherwise would have no reason to bring two Americans to and just tapping into that community and going to a restaurant afterwards and waiting for things to show up and eating them and trying to communicate with the owners. That for me is what travel’s all about, putting yourself in these situations where you’re problem solving and you’re seeing something new, and you’re off the beaten path, and you’re connecting with people even if you don’t speak the same language.

Matt: Yeah. It’s interesting the history, and you kind of eluded a little bit to the origin of street art and the graffiti movement, and I resonate a lot with it as well because graffiti art is one of the four pillars of hip hop culture, which initially emanated out of the South Bronx as part of that movement, and it was certainly illicit. That was the fundamental nature of graffiti was that it was not legal. It was not authorized and one of the ways that that evolved that I actually appreciate is the ongoing nature of graffiti art in a number of places. One of the most prominent ones where you and I have both been is in Bogota, Columbia. One of the amazing things about Bogota is that they estimate that there are 7500 active street artists in Bogota and it is definitely, without question, the top three street art cities in South America. Those three probably Sao Paulo, Valparaiso, Chile, and Bogota compete for the top three but certainly, it’s in the top three. One of the things that I appreciate, particularly in a city like that, when you go to the old city in Candelaria, and you look at the street art that emanates from the original nature of street art, is that it is a way for people to express a counter-hegemonic narrative through art. It’s a lot of communication, and rhetoric, and expressing of social and political views from marginalized positions in society that don’t necessarily get mainstream representation. It’s a medium to communicate, often times antiestablishment or counter-hegemonic narratives of some kind, and so they can be relating to the indigenous struggles, relating to women’s struggles, relating to various different anticolonial struggles by communities of color. In Bogota it was amazing to me to go around in Candelaria and see oftentimes the connection between different marginalized groups that would collaborate on the street art projects. There was literally like a punk rock person in the same mural with sort of an indigenous or just different kind of marginalized groups that are not mainstream social groups coming together to express their narrative, and their experience, and their social and political views through a medium that is not sanctioned by the government or is not sanctioned by corporations. Now what ultimately happens, as you mentioned, is that streets artists are so talented, like raw talent. It’s just like any kind of artist like a rapper or somebody who is just has this like incredible raw talent and eventually of course they get hired by a corporation to do their art. Sometimes somebody will commission a mural and be like that artist is insanely talented. Look at all their graffiti pieces. I want to pay you to do this big mural on the front of my store and that kind of stuff. So a lot of people are starting to get into that as well.

Ali: A word that stuck out to me that you just mentioned is expression, and I think this type of art as a means of expression is incredibly important and I think in whatever format the expression is taking whether it’s sanctioned by corporations or the government or done more sort of the in the dirty roots of how graffiti started maybe, there’s a place for all of it. I think that’s really special too and I think you’re seeing a lot of respect with street artists, and graffiti, and taggers, and certain communities where they know what boundaries to push and what boundaries not to push and just the evolution of how all of these different types of art can live in urban environments together is quite interesting. I think I really put the pieces together on this in Barcelona. So, I do a street art tour in every city that offers one. It’s like the first think I like to do outside of finding good coffee and strong WiFi. In Barcelona at my street art tour, two things that were really interesting happened. One is we saw a community garden that had painted murals for an incident where there was a death of a member of the community. What happened there is the police broke up a brawl and through the police force trying to stop the brawl, someone had died. The community felt like they were being silenced and so they built this memorial garden and put up street art to talk about this event and to remember the person in the community that passed away. Over time other street artists came to that garden and painted similar expressions of crime that had had happened around the world. So, for me, going there I learned about a few different incidences throughout the world, not just in Spain, but also things that happened in South America that I had no idea about, and it sparked me to educate myself. So, if there had not been a mural and if there had not been graffiti then I would have just wondered around Barcelona and maybe had some sangria but instead, I learned really interesting things about humanity that had happened in the past and current events that I had no idea otherwise. So, I think just using art as a format to express, as you mentioned, injustices or political beliefs and things like that, really give an opportunity for people to educate themselves. Then the other quick story is while we were walking around Barcelona, there is a street artist that’s getting a lot more attention lately and he’s 12 years old, like 12 years old, and that’s just so cool that despite your age, you can jump into this field and our tour guide said if that street artist keeps it up as a 12-year-old, he will transcend into the type of street artist that people are paying big money to have commissioned and sanctioned murals by and earn a living and have this cool career of expressionism. Most 12 year olds don’t get told you can be a street artist one day and I just thought that was really…

Matt: It’s amazing and in Barcelona in fact, a lot of these street artists are negotiating, right, because the tension is are you “selling out” or are you being coopted if a corporation or the government is paying you or even just legally allowing you and providing your paints to just paint somewhere. Is that a sellout thing? So, one of the negotiation dynamics that’s going on in Barcelona and other places is if a business wants to pay you because you’re just like an incredible street artist, to do the piece on the front of their building, some of the street artists are saying yes I’ll do it. I’ll take your money and I’ll do a piece, but I get to choose what the piece is. You don’t get to tell me what to paint. So, as long as you have a piece by this artist on your front, they’re going to control their freedom of express and paint whatever the heck they want and that’s the negotiation. It is really interesting to see how this is evolving.

Ali: Yeah and as someone has a little bit of that don’t tell me what to do attitude, cue my high school story again, I love that. Don’t tell people what to do. Let their art speak for themselves. Let them express themselves. If people are respecting humanity, don’t hold them back.

Matt: Yeah and I was in Sao Paula, Brazil, last year which also is a contender for a top art city in South America, for sure epic amazing. But one of the things that happened there was that the police did a sweep, and they intentionally targeted and arrested the top street artist in the city and literally threw them in jail. There was all this outrage, like you are insane. How could you possibly do this and all this outrage but the street artist did is he negotiated from inside prison with the government. They negotiated to have what is now known as an open air museum where they would be a allowed to have a segment of the city where street artists could have total freedom of expression to do their works in this designated area and so that was one of the negotiations. So now the government allows this place. It’s in northern Sao Paulo. It’s incredible. You should go see it if anybody goes to Sao Paulo, but it’s a place where street artists can do their work and they’re allowed to do it by the government. That’s again some of the way that this stuff is negotiated, but that’s always a very interesting questions. That’s one of the first ones I ask when I do a tour in the city, what’s legal? What’s not legal? What’s commissioned? What’s not commissioned? Make sure when you’re showing us the different pieces, I’m interested to know which ones are legally allowed and which ones aren’t so that I can interpret the works in different ways and then I’ll go in for those questions. You know?

Ali: Yeah and now I might have a new place to add to my bucket list.

Matt: Yeah, Sao Paula for sure. Yes, for sure. It is amazing and it’s definitely, I think, a transformative element as you mentioned is the other term that you used that I think it is really significant because there are a lot of communities. When you were in Columbia, did you go to Medellin? Did you see Comuna 13 and what they’ve done with street art?

Ali: Yeah. It’s one of the more incredible stories of street art in my mind and just how art and taking pride in where you live and beautifying it and having a place to express yourself can totally turn around a whole entire community and their livelihood. It was such a cool story.

Matt: Yeah, it’s amazing. For people that don’t know, there was a community in Medellin. One of the things that happened, and depending on who tells you the story about the community, you’ll get different pieces of this narrative, but basically what happened is the community was accused of harboring political rebels. The government, which was a really ruthless authoritarian regime at the time, probably about 15 years ago.  This was backed by the United States government, in fact, and US tax dollars. What they did is they came in and they just basically did a massacre of the civilian community there, claimed that they were harboring rebels and they were literally shooting civilians from helicopters. It was a horrible massacre. What happened was, the community, when they rebuilt themselves, they rebuilt themselves on the pillars of hip-hop culture, a centerpiece of which was street art. So, the community was able to paint murals of everything ranging from things that reminded them of their place where they came from or things that made them happy. So sometimes you’d see pictures of animals or pictures of wilderness stuff and paintings like that, but then you’ll also see, again it was founded on the pillars of hip-hop culture and so there’s a hip hop community center at the base of the community where they literally teach kids the art forms of break dancing, DJ’ing, MC’ing and graffiti arts starting at the age of five. There’s a mural of Rakim in the middle of the community. There’s this whole hip-hop component to it as well, and it was basically like the community taking control of their environment and putting the art up on the wall that inspired them and then being able socialize the youth in that community into art forms that would allow them to have that freedom of expression and take control of their community. It’s an amazing inspiring place to go. So, if you’re ever in Medellin, Communa 13 is incredible.  All right, so with that, let me ask you one more macro question about the digital nomad movement and then I want to move into a little bit about your professional expertise and start talking about people ops. Maybe this is even a transitionary question, but how do you see the impact of digital nomadism on personal relationships, and communities, and society at large in the traditional sense? What is transforming here?

Ali: Oh, there’re so many things that are transforming here. I think really when it comes down to relationships around digital nomads, I’ve found that you meet a lot of people who are extremely independent and really just satisfied with life on their own. There is this weird stigma, and I haven’t explored too much how true it is. I only have initial reactions to it that people that are digital nomads are so comfortable with this independence that two things happen. One is they seek out really transient relationships and they have people that are fun for now and they dive in and out of communities, and the other is that people experience bouts of isolation and loneliness as a digital nomad. Now that I’ve been doing this for three years and I mentioned one of the things that I do when I travel is to let myself be open to traveling based off of people I meet. I feel like I’ve experienced both of these things but a little bit stuck in between the two. What I mean by that, just to elaborate, is I say very openly in my life right now that the most important thing that I could have is deep and meaningful relationships with others. While yes, I do mean that in a romantic way, but I also mean that in a friendship way. I also mean that in really connecting and getting to know people that do interesting work that I want to support and figure out why their passionate about it. I don’t want to know what you did in the last country you went to and what country you’re going to next. The superficial conversations that you tend to repeat as a digital nomad because they’re icebreakers, they’re interesting and I love learning that about people, but I crave this deeper more intense conversation. So, what I think is really cool about the digital nomad life also with means of technology, is that you can open yourself up to really experience things with lots of different people and flow in and out of periods of isolation and loneliness, and then seek out not just in-person relationships but these virtual relationships that are being built over time. Transitioning this into people operations is one of the things I think about more deeply at a professional level, not just a personal level, in terms of if I am working for a company that has people as far as California to Uruguay, France, and Japan, how are those people actually getting to know each other and building a level of trust because they’re not seeing each other in person? The basic dynamics of relationship building is true whether it’s personal, platonic, family, romantic, professional. You need to be, again this is a word I’m going to use a lot in this podcast, I’m going to have to remove it from my vocabulary, but intentional. You really have to be intentional about how you’re communicating, why you’re communicating, and what you’re communicating to build relationships and seek out connection proactively if you’re going to succeed in being a digital nomad.

Matt: Maybe at this point you could talk about the distinction between digital nomadism and remote work because I think those two things are increasingly conflated, and maybe you could sort of disaggregate them and talk about what the differences are.

Ali: Yeah. I’m really glad you pointed that out because actually everything I just said is true for remote workers as well, and I will now explain the difference. I think do people confuse, oh, you work remotely with, oh, you’re traveling the world or have a laptop on the beach or kicking it in Thailand, which I’ve never been to, by the way. But remote work is a lot more than that. It’s really just about, again, this idea of having control and having flexibility, about approaching work in an environment that you are happiest, holistically in your life, in a way where you can work when you’re most productive and utilize technology to help you succeed. So when I think about remote work, I think about it really as this umbrella to being anybody who creates their career or their means of financial support in a way that relies on technology but gives them the freedom to do it anywhere. Then a small subset of that is digital nomadism, which yes are people that are traveling the world and working and moving around to different countries but even within that, I think there are a lot of variations of that. I’ve lived two variations so far, which is where I did extended periods of time outside the US, and then extended periods of time in the US and found balance. Now I travel fulltime staying in places one to three months at a time. When I think about my professional life, I’m pretty unique. I work for DuckDuckGo. There’re 55ish people right now that work there. I’m the only digital nomad and everybody else lives these incredibly fulfilling lives that are very different from each other, but aren’t living out of suitcases and going on safaris on their weekend trips. They’re people that didn’t want to live and deal with commutes and prices of cost of living in San Francisco and the hustle of New York City. They just wanted to be with their families in a town close to their friends but still challenge themselves in a field that’s really competitive such as software development and live just a better life for their interests. So we have people like that live in small towns in the US. We have someone who lives in Saskatchewan in Canada. It allows people to really create the perfect life for them.

Matt: Yeah. I think that’s important and a lot times when people ask me about things and stuff that I do. I explain that I’m not trying to tell people that everyone should do what I do but I do have the position, and what I explain to people, is that location dependence is inherently valuable because it empowers you and gives you the choice. People will oftentimes ask me is your travel pace too fast? Are you ever going to “settle down” or what if you have kids, or if you do this, if you do that? I was like listen, for me it’s not about any of the specifics of the lifestyle elements that I’m choosing at the moment. It’s about the freedom to choose them. So, next year, I might choose something different. I might choose to travel slower or travel faster or, if I want to stay in place for an entire year, or five years, or whatever, I have the choice to do all of those things. So, it’s the feeling, for me, of the empowerment of having the choice to choose your location. You can move wherever you want. If I want to go and spend a month or two months with my family for the holidays, I can do that and I have no restrictions upon me. So, I think it’s really about removing geographic restrictions, creating the location dependence for you to make the choice, and then each person can make a different choice that suits them, and those choices may change at various phases of their life.

Ali: Yeah and I think too, not just at a personal level and not just at a community level, but also at a society level, remote work is really important because what it’s doing is it’s allowing people to have more freedom and flexibility to get things done that impact how governments are spending money to take care of their society. If you think about things like women’s health, if you don’t have the freedom and flexibility to remote remotely and maybe you have a job or you’re working two jobs to support a family, to find time to take a day off and potentially lose pay to go see a doctor, go fill prescriptions, to take control over your health as a female is a challenge that a lot of people have in certain environments.  Whereas if they have remove work and flexibility, they can schedule those appointments not just during the hours of 9:00 to 5:00 when they’re supposed to be at work. They can go at 4:00 p.m. and that means they’re working until 8:00 p.m. and it just allows them more access to things. I think that’s incredibly important. We’ve created this rigid society where literally everything gets done between the hours of 9:00 to 5:00. If you need to go to a bank, you probably had to do it during your lunch break because after work the bank’s closed. If you need to go grocery shopping or pick up dry cleaning, everybody in a lot of places is doing that at the exact same time and then that has wear and tear on public transportation, how you’re thinking about cost of fuel and the bus lines, and the streets, and the people who are working to do those jobs. Literally, remote work has potential to change every decision we make in a society.

Matt: Yeah, totally agree. One of the things that I think is interesting about you and that I want to ask about you is that a lot of people have the impression that digital nomads, or perhaps even remote workers in general, are people that maybe are computer programmers and just get assigned tasks that they have to go do and then submit, or they’re freelancers that do maybe social media marketing, and they can do it on their own time and they have a couple clients and they’re sort of a freelancer, or I think there are stereotypes of the sorts of job categories that can be digital nomad conducive. You are a fulltime, salaried, W2 employee, and you are also a senior-level leadership position at a 55+ person company, and you execute your responsibilities throughout all different time zones. You and I have been in Asia together, as you mentioned, in Vietnam. You and I are now in Africa together in Kenya. You are going to Europe next week as you mentioned. You’ll be in the United States later on. Can you talk a little bit about your responsibilities at DuckDuckGo and how you execute a fulltime senior-level position from these different time zones and in a digital nomad lifestyle?

Ali: Yeah, definitely. I also think the interesting thing is when I tell people I work in people operations, and if they don’t know what people operations is I tell them I work in HR. That’s when people really get confused that I can do it remotely because the basis of my job is interacting with other humans and so how do you really do that behind a computer screen. I think it’s quite common for people again like developers, people imagine dark room, music blaring, coding, and for me the type of responsibilities I take on is quite different. So, overarching I think really deeply, and recommend, and propose ways for our company to make decisions that will make the employee experience better for everybody that we employee. What that actually means day to day is that I am thinking through the strategy, and the decisions, and the types of operational projects we’re doing and I think through how that impacts communication, how that impacts people’s abilities to learn and grow professionally, what the impact is for culture and are people actually being effective and efficient in their jobs. Projects that I’ve worked on in the past are hiring strategy and helping hiring managers learn how to hire people remotely and think through what the needs are, thinking through professional feedback and how we handle promotions when you can’t see physically if somebody’s working or not working. How do you evaluate someone else’s success and give them useful feedback and determine if they’re ready for new responsibilities if you’re not interacting with them face to face. One of the things I love about people operations right now in this space is I studied organizational behavior in an academic setting and all of the case studies when I was in the university had examples of companies that were together in one office building and so a lot of solutions that you think through when you think of things like conflict resolution, or team building, trust building, brainstorming, all of the best practices that existed over the past 10 years resulted in in-person work, brainstorming with post it notes up on the board, conflict resolution by going out and having a coffee, talking through your issues with someone. In order to do those things remotely, we’re reinventing what best practices are. So, thinking through if someone has a conflict at work or there’s a misunderstanding or a miscommunication, how do they sink up especially if there’s a seven or eight hour time difference between that miscommunication happening. So, I think those things are just really interesting and companies such as DuckDuckGo, and other companies that are remote, first or remote only, are changing the way that we approach these really human problems in business.

Matt: Okay. So, can you speak to some of the solutions that you have developed for these issues that you’ve posed?

Ali: Yes. I’ll start with hiring because that seems to be one that’s really quite interesting for people and I think a lot of entrepreneurs eventually are going to hire people hopefully if their company’s doing well and growing out their team. I think the decisions you need to make and the approach you take to hiring when you’re dealing in a remote environment is quite different. I think advice that I would have in terms of hiring specifically and how you do that remotely is a few things. One is if you’re a company of one or two, it’s just you and a cofounder, starting to think through what your organizational structure is going to be and why is the forefront to hiring. So, are you going to hire remotely? Some of the benefits of that is access to talent regardless of a geographical area, getting the best people for the job and the role without the limitation of them coming into an office or them only being able to work certain hours is a great corporate benefit. I’m going to speak from the business standpoint right now because I think everyone knows a little bit about personally why this is so important to me but the access to talent, the flexibility around time zones and when you’re working on projects is incredibly important for a company.The downsides for some companies is remote work is really challenging and to build out a remote company takes a lot of proactive though. So, when you’re thinking through what you want your company culture and environment to look like, if you’re going to hire people that excel in spontaneous conversation or in-person brainstorms, people that really get motivated by the social aspects of work, then creating a remote environment might not be right for you. But if you think that having the best talent out there and putting in the effort to let people live their lives in a remote way is important., the next step I would recommend is thinking really deeply about the skillset, the behaviors, and the type of responsibilities that people need to have in order to do a job successfully and craft your entire hiring process around those things. It becomes less so, and I hate this, there used to be a thing that people talked about when they talk about hiring that’s like would you like to go and have a beer with this person. That makes a terrible coworker. I want to have a beer with lots of people but I don’t trust them if I’m not going to check in with them between the hours of 9:00 to 5:00 that they’re going to put in the effort to do kick ass work. I want to work with people that are going to push me to be the most intelligent person that I can be, the most hard working person I can be, and really feel passionate about the product that we’re creating. So I don’t necessarily have to have similar interests as those people but I do need to be interested in them and want to build a trusting relationship with them. So what I recommend with remote hiring is give people a chance to let their behavior speak for itself. So what we do with DuckDuckGo very tactically is we pay people to go through our interview process because we know it’s an investment. We want to see what their work can do and let the work speak for itself not the quality of their interviewing or how charismatic they are on a video call. Through these paid projects, it does two things that I think are really important for remote work to work. One is it lets us make a very objective decision on if that person can accomplish work without a manager checking in with them over their shoulder on the computer. Can we just give them an assignment and trust that they’ll do it or have enough self-awareness that if they can’t do it, seek out help. The second thing is, and I think this is equally if not more important, hiring should always be a two-way decision. You’re going to invest in an employee and an employee is going to invest in you as a company. So, by giving people real projects to work on and paying them for their effort, it gives the candidate more control to decide this is work that’s really inspiring to me. I love these projects. These challenges are interesting, and I’m going to learn, and I’m going to be really motivated to join this company and help them succeed. I make this example sometimes. If you’re interviewing for a company and you go into their office – before I worked remotely the No. 1 piece of advice I’d give someone looking for a job is when you walk into the office are people smiling at their computers. Are people talking to each other in the kitchen? If you go into the bathroom and sit in a bathroom stall, are you going to hear people gossip and complain about their manager and about work that’s going on or are people excited. You can’t do that in a remote environment. We do our calls on Zoom and it’s a video call but what we can do is give people an opportunity to join team meetings and to come and interact with people before a hiring decision is made. So, that’s the equivalent of sitting in the bathroom stall is come and participate in our company and we’ll pay you for your time and then at the end of the day we’ll both make a decision on if this is a good fit.

Matt: Awesome. That’s really good advice. Let me just ask you the distinction. I know you’ve worked with early stage startups, and I know you’ve worked with large corporations with 200 plus people. DuckDuckGo your current employer is kind of in the middle there. How should companies, business founder, entrepreneurs, or even executives think about people operations at those different stages? I feel like HR and people operations are some of the most overlooked aspects of a business. I really feel like they are.  

Ali: I really appreciate you saying that. It makes me feel good. I’m sitting up more straight in my chair now. First of all, I’d also like to distinguish HR responsibilities from people operations responsibilities. It’s quite normal for a company under 100 people to outsource their HR tasks in terms of payroll, benefit administration, things of that nature, and I think that’s totally valid. If there’re companies that can do administrative tasks for you and free yup your time to think more strategically, that could be a really good option for you as a company. One of things that I think is important in terms of people operations that is quite different than administering health benefits for example is again thinking through how are operational decisions going to impact the people and the culture at work. I think that’s something that should be thought about from day one of the organization. As soon as you’re not a solo person, leading your own charge, any decision you make is going to impact the livelihood, the motivation, and the growth of another person and investing in that person properly will help your bottom line as a business. Maybe it’s not a fulltime people operations person on staff like I’m lucky enough to have right now, maybe it’s just seeking out communities where these people are consulting and getting advice to help shape everything that you do in terms of how are we going to handle when conflict arises? How are we going to handle people that outgrow their role and start getting demotivated by routine tasks that used to be challenging and no longer are? What type of company do we want to be in terms of culture, which is a buzz word? What I really mean there is how are decisions getting made? Are decisions always going to be collaborative decisions? Do you need buy in from certain stakeholders? How do those stakeholders know how to make decisions? If they don’t know, how do we teach them? All of those questions are types of things that having a people operations person could help answer at least from the perspective of what is this impact going to be on Matt, for example, as an employee of this company because what I think happens oftentimes is you make the business decision first and you don’t think about the impact on the person. So, at the very least having a designated person to play devil’s advocate and ask the questions about what does this mean for me? What type of change is this going to be and why? How is this impacting our culture? What types of things do we want to infuse in our culture from the get go and being really proactive about it will help you more seamlessly grow from one to five people to fifty people, to hundreds, to thousands of people.

Matt: Can you talk a little more specifically about company culture? You mentioned it’s sort of a buzz word. I think it is as well, but can you talk about what is company culture? How important is it, and how should a business founder or executive be intentionally about architecting one?

Ali: Yeah. I almost wish I could change the term company culture to expectation setting. That’s really all it is just to simplify things. I think when you think through company culture, it’s when somebody’s joining this community, and a company is a community, how are people expected to behave? What are the norms? What is going to be appropriate and not appropriate, and how do you create that legacy so it’s happening without control? So really thinking through examples of that one thing that while I think company culture is a buzz word, another thing that people who do it well really get right is thinking through what their company values are and what behaviors they’re going to reward from independent contributors and leaders in the organization. I think if you can figure that out and do it through buy in of other people in the organization and get the first the perspectives on that, it’s something that you can really ingrain  as a way to make decisions. For DuckDuckGo, we have a few company values. The ones that I really appreciate as a remote worker is validate direction, and build trust, and question assumptions. Everything we do, kind of goes back to if someone’s going to be successful in this environment, they need to at least be able to do those three things. Just to break them down really quickly, building trust is extremely difficult to do in a remote environment. It’s really easy when you’re going through something whether it’s personal or profession to turn off your computer and escape and not be present in your work community. So, I think you really need to learn about the people you’re working with in a way that will help you build trust faster. So, things that we do at DuckDuckGo, one is every new person coming in has three questions that they get asked about who are you? Give us the basics about you, and give us a few things that you’re interested in or ideas you have for DuckDuckGo as conversation starters so people can feel free to reach out and make you feel more welcome. We do neighbor’s calls which is when on a weekly basis you get paired up with three or four people that you usually don’t work with. It’s never your manager. It’s usually not someone on your same functional team. It’s just an opportunity to get to know each other. Sometimes people talk about personal things. Sometimes they talk about cool projects their working on. It’s the equivalent of a company happy hour or a watercooler chat but because it’s remote, the video is on. You have to be there. You have to be present, and people start to really get past the awkwardness and dive into really meaningful things right away because that’s the point of them joining the call. We do things like that to build trust in the organization. We also have something I love. Every Thursday, our CEO posts a question. Sometimes it’s serious and sometimes it’s silly, and it’s just a way to get to know each other in the company. They get posted on Thursdays. Some threads are still going on Mondays and people now upload pictures, and it’s like things from what does your desk look like to what’s your normal lunch routine to if you could change one thing about our product, what would you change and why? So it runs the gamut of getting to know each other at the personal and professional level. I think all of those things we’ve done in a really intentional way and I’ve spaced them out on a cadence where their different but repeatable in order to build the trust. The other two I mentioned, question assumptions, I think this is another really important one because when you’re working remotely, you have less opportunity to bounce things off someone else in an organic way. You either have to set up a meeting to brainstorm and you have to have self-awareness that you need a brainstorm meeting, or you’re going to finish something and it’s not going to be great and people are going to come and give you feedback. The value of questioning assumptions is really cool because it just let’s people pop in into anything that interests them in the entire company and ask questions about what’s going on and why. We approach it from something called the most respectful interpretation, because sometimes questions especially when you’re dealing with remote work and it’s written down, and you’re not getting the tone, and the intonation, and the facial expressions, and the genuine curiosity that you see in people. I’m sure everyone I’m sure can probably relate to that text message that really pissed them off and they’re like why did I get this text message? The same thing can happen in business where you’re like why am I getting this email? But it’s usually people are busy and people are trying to finish up their work, and go do cool things, and spend time with their families, and spend time with their friends that they’re just responding to things. So, having a place where you think through what did this person mean and what’s the most respectful way that I can interpret it, not this person is out to get me, can make question asking in business really fruitful because you’re tackling the most challenging business problems, not personal relationships. I think that one is a core value of the company. The third validating direction, especially when you’re working remotely and you’re kind of on your own island with your computer get worked on, if you don’t know what’s the right decision and why you can easily go down a rabbit hole and waste time working on the wrong thing. I think when we think through company culture, already you’ve seen, by knowing what your values are you can then initiate certain activities that help you foster those values and make sure their easy to obtain. And then going back to hiring, you can actually objectively test for those values. When we give projects to people, we want to see not only what are you going to do, but explain to us why you’re doing it. That’s validating direction. We’re going to give people instructions and we’re going to trust that if they need help or if they have questions that they’re going to come back to us. We don’t enforce any sort of come and show us your work. You’re an adult. Get things done. We’re going to trust you. If you say you’re going to get it to us by Tuesday, you should get it to use by Tuesday. If you say you’re going to get it to us by Thursday, get it to us by Thursday. It’s all about expectation setting, and by reframing culture into values and activities, it makes it a lot more tangible for decision makers and for leaders in an organization.

Matt: Can you talk a little bit about the gender diversity initiatives and the importance of female empowerment in the workspace?

Ali: Yes. This has been a hot topic, I think, ever since I’ve started to really pay attention to hiring. I think a lot of companies in the tech world especially and in the United States are really struggling to figure out why and how to make both work environments better for both genders but also to attract and promote, and retain females in their workspace. It’s something that’s been getting, I think, international attention. What’s really cool and interesting for me is when I first started working at DuckDuckGo, I was the third female that joined the company. I was the first person in any sort of leadership role and the first thing that I heard from them that fortunately did not have to come to me is we’re about to grow a lo,t and we don’t want to fall in this trap of not making this an inclusive place to work because everybody searchers for things on the internet so we need the everybody in order to make this product the best that it can be. In that lens, I was looking at gender diversity but it also comes down to all types of diversity in terms of if you’re product isn’t reflective of who your customer base is, how can you make the best product for them. Also, I think it makes it a more interesting and fun place to work when you have different perspectives and you can learn from people that are quite different. Going back to the gender diversity thing, it was really important for me to do a few things. One assess what does this work environment look like for women. I oftentimes found myself in this position where if something happened that was interesting to me, I had to stop and I had to be like is this interesting to me because I’m Ali and as a human I have strengths and weaknesses. Is this interesting to me because potentially this is an unconscious bias, and it’s something that women are experiencing, but not men or is this something that everybody’s experiencing but we’re just not talking about it enough? If we can bond over our struggles, again like building trust and building relationships in a remote work environment, it’s good to bond over your success but also your challenges. I went through a period of time where I was constantly taking inventory on things and checking in and making recommendations and thinking through what does it look like to work here from all types of diversity and then really promote and talk about the benefits of remote work especially for women in the workplace. I think some of things that don’t get talked enough about, not just at DuckDuckGo, this exists at DuckDuckGo, but just generally with remote work is if you have the freedom and flexibility to earn a living in a way that can bend to your lifestyle it means that people who potentially are single mothers who before had to choose between spending time raising their children, which I think by the way is the most incredibly important job in the world because you’re impacting the future of humans in the world.

Matt: Agreed.

Ali: That for me is just such an incredible task to have to live up and make sure that you’re inspiring and creating respectful humans with emotional intelligence that are curious and excited about the world that we’re living in and going to make positive change. That’s a whole other podcast. But how do you balance that with going into an office and earning a living with chores, and household duties, etcetera, etcetera. Remote work means that you can balance out picking your kids up from school, going to soccer games, cooking dinner, and going to conference calls throughout a 24 hour period of time not an 8 hour period between the hours of 9:00 to 5:00. I think once I really tapped into the benefits of remote work and how much DuckDuckGo supports those benefits, it really opens the door for us to have conversations with more woman about what this means for them. I’m using these benefits right now as someone who’s just traveling the world and doing all these really cool experiences, but I see a future for myself where I’m also raising kids and working remotely and baking cookies for a bake sale in between sending out contracts to hire really awesome people. I just think the evolution of remote work and putting things in place to help support that is really important. Other cool things that we do that I just want to mention because they make me super happy and really proud is we pay everybody at the level of the company the same thing regardless of if they’re male or female, regardless if they have a degree or don’t have a degree, regardless if they’re living in Vietnam or the United States. If they’re performing a job that is giving the company productive investment, we’re going to pay them for the work that they’re doing and all of that information is made transparent before you even accept a job. So you can know before you’re first interview this role pays this much, and this is what we expect of you in terms of your ability to create an output. So, there’s no need for negotiation and some of the unconscious bias that goes with negotiation. I’m really proud to be able to work for a company that has such a transparent pay scale and that existed before I even started, which I love. The other really cool project that I was able to work on over the past two and a half, almost three years, at DuckDuckGo was creating a parental leave policy that supports both men and women that are bringing new family members into their lives whether it be via adoption or biologically and having to research and adjust that policy based off of the needs of people in different countries was also really incredible to be able to think of as a company, what do we want to do for our people and not based off of what certain governments dictate. Obviously, there are certain countries that do it more liberal than us and certain countries that don’t do anything. So really taking tabs on what makes sense for us and why, and how do we create a supportive environment and why are the types of work I do to not only inspire the company from a gender diversity standpoint but just in general.  

Matt: Awesome. You mentioned earlier that you have done presentations on productivity and time management and that kind of stuff. I want to ask you, in general and also specifically, as you travel the world and find yourself in amazing places that have incredible street art, and beautiful hikes, and all sorts of awesome stuff to do and cool people to hang out with that you’re surrounding yourself with intentionally, and so forth, how do you create and optimize your productivity, your output, and manage and structure your time effectively?

Ali: I’ll start pretty broad, and then I’ll go into some unique details that I think I’ve really found that what works for me. When I present on productivity, the theory that I like to use the best is something that Franklin Covey came out with which is the Big Rocks Theory. Basically, people can find this on YouTube but the way that it goes is most people start their day and if your day is a glass jar or our bottle of wine that we’re drinking here, it’s finite. You can only put so much wine into this wine bottle. When people think about structuring their day, I think the first thing you need to thing about is I only have a limited amount of hours in a day especially if you’re one, not like me because I sleep like four hours a night, who gets a proper eight hours of sleep. That’s not even all full 24 hours that you’re trying to cram all this personal and professional stuff into. You have to realize that time is finite. Your resources to accomplish things in any given day or week are finite. One is have self-forgiveness first of all. People are really hard on themselves if they don’t get everything done when they say that they’re going to get it done and knowing when you should be hard on yourself and create some pressure and when you just need to let it go and take care of your mental and physical health. What Franklin Covey does is it has this analogy of big rocks where there’re big rocks, there’re stones, there’re pebbles, and there’s sand. They represent different things that have a certain level of urgency and importance throughout someone’s work day, work, week, work month, etcetera. What most people do is they put the sand in the bottle first. They do all those easy tasks. People can probably relate to waking up in the morning, having a cup of coffee, and responding to a billion emails and then all of a sudden it’s noon and what did you do today. That’s the wrong approach from a productivity standpoint. If it works for you and you’re getting everything done, and you don’t want to cry at night, good for you. I want to meet you. But the better approach that Franklin Covey teaches is figure out what are the big rocks. What are those super meaningful things in your life from a professional and a personal standpoint that are both important and urgent and create space in a mindful way to get things done first. Tactically what people do is they put blockers on their calendar to accomplish the rocks. They do those things first or they do those things when they know their most productive which creates a layer of self-awareness that needs to happen. Once those things are accomplished, once you’ve figured out your big rocks, make room for the stones, the pebble, and the sand. I think by having that approach and really prioritizing, and what I love about this is prioritizing holistically, all of the things you need to do in your life, you can really see how much you can accomplish and set expectations appropriately. When you think about it, everything that you do in life is either a thought, a conversation, or an action, which I think is really cool way to think about time management and most people only manage their time based off of actions, sometimes conversations if there’s a meeting involved. But to create also intentional space for you to think lets you be more creative and can speed up the tactical process of accomplishing work faster. I think that’s another piece of advice I have for people is think about when you’re going to think. Some people do that in the shower. Some people do that on treadmill. Some people do that while looking at awesome street art, but you need to carve out that time for yourself to be creative and be innovative.Personally, what that means for me, my favorite tactic, I’m just going to share one because it’s maybe the most unique and is only allowed because of my remote work and digital nomad life, but I’m one of those people that I read all of these articles about how routine is good for you. I hate routine. I do not want routine in my life. I want every day to be exciting and different. I want to be inspired by surroundings. So, one thing that I do is I think about what I want to accomplish in a very specific place. I will for example say I am going to go to this particular coffee shop that’s around the block and while I’m there, I’m going to write a proposal based off of the employee engagement results that I got in. Once I finish that task and finish my cup of coffee hopefully at the same time if I’m really killing it with time management, then I’ll be like okay, cool. I’m going to leave this place now. The time it takes me for me to go from that place to the next place, whether it’s walking or going for a bike ride to get to the next place, in some cities taking an Uber, allows me time to context switch, which I think is a really challenging skill for people in business is quickly switching from one activity to the next. What I love when I’m in cities where I’m walking or biking distance from another place is that it also gives me this burst of physical activity that kind of gives me stress reduction, and adrenalin, and makes me feel like I’m out doing something fun. Then when I get to my new location, I can sit down and I can process what happened over the past 20 minutes where I got to take a lovely break and I can say, now when I’m in this position in this location, I’m going to respond to all of my emails. I very much structure my day based off of activities I can accomplish in a certain place and how many times I can context switch to go to a new place to be re-inspired.

Matt: I think that is an awesome piece of advice. You and I actually executed that today as we went to a coffee shop, and we just jammed for a two-hour power work session. Then we moved locations, and we went from a coffee shop to the co-working space, and then we jammed for another three-to-four-hour work session. Now we’re doing this podcast interview in yet a different specific location. So, I think that is a really awesome piece of advice because the other thing it does is it forces you to create goals within specific timeframes. It’s like, I’m going to spend to hours here and I’m going to try to jam and just crush all this stuff in two hours, and that’s the limit I’m going to give myself. It kind of forces you to work in blocks, as opposed to just sitting somewhere and be like I have 14 hours to do all this stuff. You know what I mean?

Ali: Yeah.

Matt: So, I think it works well.

Ali: And it gives you permission to take a break. Everybody needs a break in life. I don’t care who you are, how intelligent you are, how hardworking you are, everybody needs time to decompress from work and reset what they’re thinking about. For me, sometimes I’m like a little kid and everything has to be a fun game for me. So one thing that I’ve done to also to create awareness around time management strategy is, if I go to a coffee shop and I say I’m going to be at this coffee shop for two hours because I want to accomplish this task, if two hours goes by and I’m not done with the task, then I’ve failed at my game in terms of how I’m planning and structuring out my day. It makes me realize is there a reason why you procrastinated on this? Do you not have the right skills to accomplish this in two hours? Do you need to seek help? It gives you a chance to also create more self-awareness around your time management and your abilities.

Matt: Right, absolutely. Last question here and then I want to move onto the lightening round. Before we do that though, I want to ask your personal strategies for stress management, stress reduction, that kind of stuff for people that work in high intensity environments that’s basically a given that there’s going to be a high level of stress which may vary over time but it’s definitely going to be there. As someone that works in intense environments for sure, what have been your personal strategies for managing or reducing stress in your life?

Ali: This is a question I’m actually a little nervous to answer. I think that while I manage stress enough to be successful in my profession and travel the world, stress management is a topic that definitely impacts me a lot. I tend to run a little bit more anxious and a little bit more stressed out on a general basis. I think I’ve been joking with you, Matt, about this eye twitch that I’ve developed which maybe is from lack of sleep and maybe it’s from stress. So it definitely is something that I’m human and I deal with stress on a daily basis and I’m trying to improve upon it. So if anybody has better suggestions than the things I already do, I want to hear from them as well. But I’ll say a few things that come to mind. One is really figuring out ways where you can make yourself feel good and whether that’s emotionally tuning out to a bad reality TV show, which is one thing I do to reduce stress, or if it’s going to a yoga class, or going to a gym regardless of what city you’re in, or if it’s taking those quick 10 to 20 minute breaks in between locations. Knowing what’s going to quickly bring you back to your equilibrium as a human is really important to me. For me, I think it’s a few things. It’s definitely some sort of physical activity. Every weekend I like to get out into nature and hike and that’s my way to reduce stress. If I’m spending a whole weekend in a city, I better be seeing awesome street art because otherwise I’m going to be like a stressed out human being. I just need to reconnect with green space and fresh air and do something physically challenging. Throughout the week if I can do yoga or workout that is really important to me and helps ground me. While traveling, stress reduction that I do is trying to make my life as normal as possible not necessarily from a routine standpoint, but I love cooking. I love having people over for dinner. When I do that, it makes me feel good and the dancing around in the kitchen and chopping vegetables is something that I’m smiling right thinking about throwing a dinner party somewhere in the world. Let me know where you want me to go. That’s a stress reduction for me. I think finding the ways where you’re making yourself happy and creating time to make yourself happy is really important.

Matt: Awesome. Ali G., are you ready for the lightening round?

Ali Lightening round.

Matt: Let’s do it.

Ali Let’s do it.

Matt: All right. What is the top book that you would recommend that has greatly impacted your life?

Ali: The Giver.

Matt: By?

Ali: Lois Lowry.

Matt: What is the top app or productivity tool that you’re currently using that you would recommend?

Ali: Asana.  

Matt: Okay. What is your favorite podcast or blog that you’re reading or listening to right now?

Ali: I don’t know if this counts as a blog, but I read a lot when I’m traveling a website called The Culture Trip. It has a lot of inspiring lists of places to go and neighborhoods to check out and is a great way for a quick introduction to a city.

Matt: Awesome. What is your top three favorite travel destinations that you’ve ever been to that you would most love to go back to and recommend that other people definitely check out?

Ali: I’m glad you gave me three because I hate having favorites.

Matt: Give me three.

Ali: My three would be Cape Town, Argentina, and Lisbon.

Matt: Now you gave two cities and you gave an entire country.

Ali: Yes. It had to be that way.

Matt: Okay. Fair enough because the country of Argentina is enormous. It’s the eighth largest country in the world and there are a number of amazing things to do it in. So that’s fair.

Ali: I mean you have hiking, and nature, and camping in the Patagonia. You have wine in Mendoza, and you have street art and awesome urban lifestyles in Buenos Aires, and you have all of those three things in Cape Town and Lisbon so Argentina needed the whole country.

Matt: Fair enough and it has waterfalls in the north on the border.

Ali: Also beautiful.

Matt: Which are insane. Totally agree with that. I was skiing in Bariloche last year in the Andes Mountains which was just totally bonkers. So it’s an amazing country indeed. I lived there for about four months. So totally agree with that. Okay. What are your top bucket list destinations that you’ve never been to that you most want to go, the top of your list?

Ali: Top of my list.

Matt: Top three.

Ali: Okay good. I have four. Can I give four?

Matt: You can give four. I give you special permission to give four.

Ali: Iceland is top, top, top, No. 1, Morocco, Bolivia, and Turkey.

Matt: Good picks. Those are all very high on my recommendation list. Good for you.

Ali: Well, I’ll be hitting you up for the best places to go.

Matt: Hit me up when you want recs on those. Yeah, Bolivia is my top recommendation in South American sort of trips. It was just epic when we went there and I just did Morocco as I said for a month this year and Istanbul is one of my favorite cities in the whole world. Amazing picks. All right, last question now. You have Michigan roots.

Ali: I do have Michigan roots.

Matt: My business partner Valerie is from Michigan so I would be remiss if I didn’t close out with a final lightening round question and ask you what is your favorite Michigan based sports team?

Ali: The Red Wings.

Matt: Boom. The Detroit Red Wings represent. All right. Good answer. Awesome. Ali, thank you so much for being here. Let me ask you how people can find you. Maybe say a little bit about DuckDuckGo, about what you guys do, what you value proposition is, how can people can use the services of DuckDuckGo and then also for you personally how can be people follow you on social media and see your travel adventures and all that.

Ali: Okay, awesome. DuckDuckGo is an online privacy tool with its roots as a search engine and we don’t collect, store, transfer, sell any data about what you’re looking for online and so we truly believe that privacy is a right, and you can get information that is objective while staying anonymous. We’ve recently expanded our offerings so we’re not just a search engine anymore. We also have a mobile app and an extension, which is a tracker blocker. So when you leave the ecosystem of search and are perusing the web, you know who is collecting information on you and what they’re collecting. We’re also starting to think through really privacy and education and people not really understanding the benefits of why you don’t want everyone to know everything about you on the web.

Matt: How can people use those services?

Ali: You can make DuckDuckGo your default search engine in any browser by going to DuckDuckGo.com and following the instructions there and also downloading our mobile app both on android and iOS by searching for DuckDuckGo.

Matt: Awesome and then if people want to follow you personally on social media to see your epic travel adventures, and I can affirm that you are an amazing person to follow on social media because you do epic stuff, how do they find you?

Ali: I keep my Instagram page pretty active with things that are happening in my travel life and you can find me there on @seeingreene, which is S-E-E-I-N-G-R-E-E-N-E, so one G, an extra E at the end, got to keep people on their toes but it’s @seeingreene on Instagram. I’m also on Facebook, Ali Greene. There’s a picture of me with some awesome street art as my profile currently of course. So you can hit me up there as well.  

Matt: Amazing. Ali Greene, thank you so much for being here. It was a pleasure to have you on the show.

Ali: Thank you.

Matt: Good night everybody.  

[End of Audio]

Duration: 109 minutes