Jonathan Kalan is a 37-year-old photojournalist-turned-entrepreneur who built his career reporting from the front lines of revolutions, refugee crises, and emerging tech scenes across Africa and the Middle East. (jonathankalan.com)
Publishing in outlets like The New York Times and The Atlantic, he covered the sharp edges of globalization—until the stress, financial instability, and nonstop travel burned him out. Tired of chasing deadlines and scraping by on freelance checks, he walked away from journalism without a clear plan, except that he wanted more control over his life.
That decision led to Unsettled, a company offering travel experiences designed for professionals who weren’t ready to settle into a single career, city, or routine. Jonathan describes the chaotic early days of launching the business—testing ideas in borrowed villas, running trips on razor-thin margins, and figuring out how to sell something as intangible as “structured uncertainty.” The demand was immediate, and Unsettled quickly expanded to destinations across Latin America, Europe, and Southeast Asia, attracting mid-career professionals looking for something between a vacation and a career change.
But growth didn’t mean stability. Jonathan talks about the financial rollercoaster of running a business dependent on global travel, how the pandemic nearly destroyed everything overnight, and the brutal decisions he and his co-founder had to make to keep Unsettled alive. He breaks down the economics of the business—why they never took venture capital, how they priced trips to be profitable but accessible, and what it took to rebuild after their revenue went to zero in 2020.
These days, Jonathan works as a startup consultant, helping founders navigate early-stage growth, branding, and business strategy. He shares how his experience building Unsettled shaped his approach to entrepreneurship, why he’s skeptical of venture-backed business models, and the biggest mistakes he sees new founders make. We also get into the time he nearly bought a failing surf lodge in Nicaragua, the strangest place he’s ever worked from, why “hustle culture is bullshit,” and our shared experience of cycling the Carretera Austral in Patagonia.
Full transcript: dirtbagrich.com/jonathan
Recorded in December 2024.
Transcript
This is an AI-generated transcript. Typos and mistakes exist!
Blake Boles 00:00
Jonathan Kalan, welcome to Dirtbag Rich.
Jonathan Kalan 00:03
Thanks so much Blake, great to be here.
Blake Boles 00:06
Tell me about your life as a dirtbag photojournalist.
Jonathan Kalan 00:12
So my life as a dirtbag photojournal as well, I would say it happened partially intentionally and partially through serendipity. So I graduated college in what, 2010 in Santa Barbara and I ended up working in LA for a year to start up and realized very quickly that while I loved the sort of uncertainty and chaos of startup life, sitting at a desk for 12 hours a day was not my style.You know, I had experience with some photojournalism in college, I was, I guess, fortunate and unfortunate is the way to put it, enough to be living in Santa Barbara when we had some pretty intense wildfires. And so I was up there in the mountains shooting, taking risks and the adrenaline, the excitement, that idea of just capturing this incredible image that few people would dare to go capture was addictive, incredibly addictive. And so when I was thinking about kind of what I was gonna do to let’s say, unchain myself from that desk, I had a lot of big ideas, a lot of big questions, you know, the cliche of maybe I’ll just buy a motorcycle and drive across South America. When one day I was wandering around a neighborhood of LA that I wasn’t normally in, and there was a sign that said, moving to Africa, selling everything. And I was like, huh, that’s cool, I’m curious, let me go check it out. So I ended up going and talking with a woman, she was starting an organization in Africa, there was a social enterprise that was designed to, you know, help orphan kids, it was a boarding school for orphan kids that was supposed to have micro businesses that would help fund the school run by students. So anyways, long story short, within a month I had sold all of my things and hopped on a one way ticket to Tanzania to first climb Kilimanjaro as a photographer for a fundraising climb they were doing. And second to help work with this organization on business development. So in the back of my head, I said, this is gonna be an incredible opportunity to sort of see if I can pursue this idea of being a photojournalist. And that sort of crazy serendipitous moment decision ended up turning into about four years of becoming a full-time photojournalist and journalist across East Africa and the Middle East.And, you know, it was something where I literally went with almost no plan. I mean, I had a roof over my head in Tanzania and I had a so-called job that I wasn’t getting paid for, but it gave me the ability to, whenever I wanted to go off and travel East Africa and to just explore ideas, themes, concepts that were interesting to me. And at that point, I was really interested in this idea of, you know, how can businesses be a force for good and how can I document various projects like solar, water, energy, agriculture and businesses that were really, we call sort of social enterprises, trying to make money and do good. And so I found that a project doing that built out this career as a photojournalist doing that and then slowly tumbled into sort of more mainstream photography and journalism. And the rest is a pretty wild history.
Blake Boles 03:41
If we’re going to get to the rest, you said you had a so-called job, were you getting paid and if not, how were you paying the bills while you were living in Africa in the middle East?
Jonathan Kalan 03:51
Yeah, so I went with about $5,000 in savings and I stretched that $5,000 pretty much for an entire year until I started getting paid. So the organization I was working with, they said, listen, we’ll give you a place to stay. And that’s it.So I had a roof over my head. It was a one bedroom house in sort of a very low income neighborhood in Dar es Salaam, where sort of all the expats and the diplomats and those types of people live. We had four people sharing one bedroom, all my colleagues, all women, and no running water. So I had a roof over my head. I wasn’t getting paid, but I had enough to survive. And so for me, that was enough. For me, I said, great, I’m here. I want to take this risk. I want to take this opportunity. I want to sort of prove myself. And I think at the end of the day, there was always a sort of fallback where if the photojournalism and that sort of pursuit didn’t work out, I could always say, oh yeah, I went to Tanzania as the director of business development for this small social enterprise. So there was kind of this backup plan in a sense, but it was really up to me to kind of prove myself and move in that direction. And it took about a year. I think I ended up with maybe like 500 bucks left in my account by the end of that first year. I smelled like rice and beans because that’s mostly what I ate. But at the end of that first year, I started to find publications and outlets that would actually pay me and begin to sort of move in the direction of actually making money and being able to do what I loved.
Blake Boles 05:31
And who were these people who started paying you for photography? And what kind of photography were you doing?
Jonathan Kalan 05:38
So yeah, so it started out with this project that I founded called the BOP project, which is sort of the base of the base of the pyramid project based at the economic period pyramid, which was this sort of concept I talked about earlier around how is business sort of a force for good. And I went around and documented about say about 20 or 25 different social businesses, social enterprises across East Africa from Rwanda, Kenya, Tanzania, Uganda, and built this portfolio and became sort of a, I wouldn’t say an expert, but there’s, there’s very few people documenting what I was documenting. And so it was at this time where the media was starting to turn its attention to positive narratives from Africa. Right. You know, we tend to hear about war and famine and all of the bad things. And I was out there really showing, Hey, like that’s not the full story, right? There’s other things going on here. And so I think I, I hit this sort of wave of interest at the right time.And I remember the first, excuse me, the first publication was a blog called next billion out of, I think it’s university in Michigan. And they just gave me a platform so I could post and write and share the stories that I was covering in a non-commercial way. It was free. And then one day one of those blogs was picked up by Christian Science Monitor. And they didn’t pay me for it, but all of a sudden I could say, Hey, like I’m publishing a relatively known newspaper. And from there it made it a bit easier to start pitching Christian Science Monitor to pay. And then kind of kept going on from there until eventually, I think I was 23, maybe I ended up meeting somebody from the BBC and started writing a column for the BBC futures called matter of life and tech. And it was, again, sort of covering the photos and stories, really interesting technologies across the region that were really life-changing for a lot of people. And I think I was the youngest columnist for BBC. They didn’t know how old I was. And when they found out later, they’re like, man, we never would have hired you. But sort of the advantage of being somewhere where you only work virtually with people.
Blake Boles 07:54
Yeah, so what was the economics of your life in your mid 20s as you were slowly piecing together this photojournalism career?
Jonathan Kalan 08:03
Yeah, so it it varied. It varied a lot. You know, there were some months where I made, you know, $200. There was some months when I made $3,000. Right. And, you know, even when I moved from Tanzania to Nairobi, I kind of got my own place. This was before the living in a closet. This was when I actually paid a moderate amount of rent. I think it was maybe two or 300 bucks a month. You know, it varied, but I was always able to sort of get by.You know, I think that’s sort of the advantage of going somewhere that nobody else is and doing something that nobody else is, is that, you know, you’re really able to sort of live in your own way. And it was stressful, but I loved it.I mean, I was thrilled. I mean, I got to literally travel, you know, all the time, all over the region and get paid for it, even modestly. So, you know, I would, I would pursue the photojournalism part was really the passion. And that’s a lot more unpredictable in terms of income, you know, you might get a gig that is, you know, pays you $500 for a shot or an article, you might get a gig that pays you $1,000, but most of it’s pretty low.I would supplement that by doing photography for nonprofits and doing writing for maybe development publications, and those will pay a lot more. And it wasn’t so far outside of the scope of things I enjoyed. I mean, I still loved writing and shooting about those topics, even if it wasn’t mainstream media. But, you know, it was it was weird where I was I was not saving probably at least until the, I don’t know, maybe second or third year. And I remember distinctly there was a time in Nairobi where I was hanging out with friends having dinner and all the matathus, which are sort of public transportation, it was a little bit too safe because it was, I think, like one or two in the morning. And I had to pay $20 or the equivalent of $20 to get a taxi back to where I was going. And I remember literally crying because I was so frustrated and so angry that I had to pay $20 as opposed to $2 to get back home. And it was just sort of, that was sort of the, I don’t know, it was, it was, it was an interesting, it was an interesting time.But I didn’t, I didn’t regret it. I didn’t feel like I was missing out on something. It was just, it was a choice. And I was happy with that choice, even if at times it, it limited my ability to do some things I wanted to do or, you know, take a cab home.
Blake Boles 10:19
A few years ago I got stuck at Las Vegas airport late at night and take it to my friend’s house. I needed to take a taxi ride that was I believe 12 minutes and cost $75 and I felt like crying.Yeah, yeah, it still hurts, it still hurts. Let’s go back a little bit and talk about your earlier life, your upbringing and those college years, kind of everything before you discovered your passion for photography in the burning hills above Santa Barbara because I know you had a bit of a less conventional childhood. Talk about that.
Jonathan Kalan 10:56
Yeah, I would say I had a pretty conventional childhood in some ways, you know, I grew up in a small town in Connecticut, you know, my parents were, you know, well upper middle class, they were very well off and, and, you know, I had the luxury of being able to go to private school, even if I got, you know, kicked out once in high school.
Blake Boles 11:18
What’d you get kicked out for? You can’t just leave me hanging.
Jonathan Kalan 11:22
So I went to boarding school for a year and I got kicked out for drinking and it was unfortunate because they actually sent me up, they actually told all the, I guess it was like the prefects or the student kind of advisor people, they said, we want you to get this kid kicked out this weekend and they just so happened to catch me drinking. It was because I was a little punk, I was in punk bands and even though I wore a jacket and tied to the school on the weekends, I would wear the camo vest with the spikes and studs and I don’t think that was a good look for a Connecticut boarding school. So yeah, one time policy that kicked me out, greatest thing that ever happened to me, I went back to the public school where I grew up and have lifelong friends from that high school.But it was unconventional in the sense of my family. So my parents were very adventurous. They had incredible lives. They lived all over the world. I grew up on stories of my parents telling me when they hitchhiked through the Congo in the seventies and were in Uganda at the rise of Idi Amin and had to sort of flee back to Kenya before things got too crazy. And growing up, they would take an unconventional path to travel. You know, they wouldn’t spend money on cars and new TVs and all of that. They would spend money on travel. It’s what they valued. So, you know, I think one of my earliest memories is at the age of I think it was five or six. I remember being in the highlands of Erie and Jai and Papua New Guinea and literally just being thrown on the shoulders of some, you know, pretty much fully naked woman with bones in her noses and beads all over and being carried away into a small hut, dropped on the floor. And then this other woman rubbing my head and rubbing her belly. And it was because I had really blond hair and that was apparently good luck and she was pregnant. So, you know, those kind of experiences at a young age and traveling the places that were really off the beaten path, I think gave me a sense of perspective, a sense of appreciation for the world. And it made me feel like I never really fit in where I was growing up. And I think my parents, you know, they they felt the same way. And we just lived a rather unconventional life in a conventional place.
Blake Boles 13:41
Hmm. Yeah. Connecticut. I could see, I could see a slight conflict there. And then your, your time in, in Santa Barbara, you, you told me that you went there because you wanted to surf.
Jonathan Kalan 13:54
Yeah, so I was born in Connecticut, but I feel like I was meant to be in California. You know, part of it was I’ve always I’ve always had this search for perspective. I think if there’s a through line through all of my work as a journalist, as an entrepreneur, you know, whether it’s, you know, interviewing entrepreneurs while a revolution is going on in the streets of Cairo or whether it’s, you know, running into, you know, a terrorist attack in Kenya or building a company. I’ve just always had this desire to understand how people view the world differently, how we experience the world differently.And, you know, for me, when I went to college, it was, well, where’s the furthest place I can go from Santa Barbara? Sorry, from Connecticut. And I applied to college in Canada. They never got back to me. Santa Barbara seemed like a great second bet. And so I moved out to California, I learned how to surf, became a surf bum, became a, you know, a dirty hippie. I was the guy who was skateboarding a class barefoot with a rug on a skateboard and, you know, living a good life. I had a brief interruption of that when I spent a year abroad studying in India, which was, again, pretty much the exact opposite of Santa Barbara. I lived in New Delhi for about seven months and then spent about three months in Nepal. And I was very grateful to come back to the sort of beauty of Santa Barbara after that.
Blake Boles 15:16
And you were able to get through college without having any student loan debt, right?
Jonathan Kalan 15:23
Yeah, and I think that’s a really, you know, we talk about sort of this idea of dirtbag rich and opportunity and fulfilling your passion and sort of being able to live your dreams. I think the greatest gift that I had and the greatest enabler for me to make my own decisions and live my own life and really take risk after college, you know, moving to East Africa with $5,000 in your bank account, probably isn’t a smart move if you have $100,000 in student loans. And I was really fortunate in that I was able to graduate college debt free. And that gave me a world of opportunity. It was an incredible gift that I think not many people have.And it allowed my risk tolerance to be a lot higher, because all I had to do was survive. All I had to do was make enough to be able to get by each day, you know, at least in my 20s, I figured once I get my 30s, I’ll figure out how to save and you know, we’ll go from there. But at that point, it was it was really just survival. And I was able to do that without that burden of debt. And I think it really influenced my choices, my ability, my path, the ability to follow my purpose. And not to say you can do that. You can’t do that, you know, without without, you know, having debt from college, but it is a huge leg up.
Blake Boles 16:40
I also received that leg up and yeah, in retrospect, being able to really play an experiment in your early to mid twenties is, is really quite crucial. Like these are the years of like maximum possible risks taking. And that can just branch that can fork your life path into this totally different direction that if you really had to focus on just paying off debt and interest and essentially optimizing for security at that point, it could take you down to this other fork that, um, yeah, would totally be less adventurous.
Jonathan Kalan 17:18
Totally. And that’s a path a lot of my friends had to take, you know, when they graduated, they had to get good jobs. And then, you know, they worked their way up the ladder, and then by 26, 27, they end up, you know, meeting their partner. And, and I think that, that sense of their ability to change everything, to shake everything up, they have too much that has been, there’s too much stability, and they’re too entrenched in society, and they’re too entrenched in, in the world that they live in, that it becomes way harder to just step back.Whereas, you know, if you, if you step out of the rat race, if you step out of the system in the beginning, I think it becomes a little bit harder to reintegrate later on in life. But, you know, you’re, you’re, you’re just able to do so much more, and you have the flexibility and the creativity and the and the drive. And yeah, it’s really, it’s interesting. I mean, you, one of the things I see in the company that I ran, so I ran a company called Unsettle that was an adventure travel company for entrepreneurs, creative professionals. And we started doing sort of one month co-working retreats and sabbaticals. And our biggest audience was, you know, people who were, I’d say 35 to 45, who had lived the conventional life, and then just, just broke down with it, they couldn’t handle it anymore, they needed a break, they needed to shake up, they burnt out. And all of a sudden, these are the people who are seeking those experiences. And it’s incredible that they were able to do that and really change their life at that age.But it’s because, you know, they had just climbed their way up the ladder and live this very somewhat conventional life for all of their 20s and early 30s. And, you know, hit that point where it was just too much. And so I found it interesting that I’ve lived sort of the opposite where I had all those experiences and kind of now, at 37, I’m sort of shifting into a slightly more conventional life.
Blake Boles 19:10
Hmm, but you did flirt with some burnout and some disillusionment. I want you to talk about when you achieved your life goal as a photojournalist.
Jonathan Kalan 19:20
Yeah. So, so kind of when we left off on the photojournalism part, I was, I was writing for BBC and, you know, I was getting paid relatively well, which for me was, you know, 1200 bucks, 1500 bucks a month, which at the time I was living in a three by seven foot kitchen cupboard under the stairs of a friend’s house for 50 bucks a month.So my expenses were very low. So I was able to save and, and, you know, I, it was a life dream, I think, for many photojournalists and really many photographers to get a front page in the New York Times. For me, it was sort of this life goal that I thought, you know, maybe I’d achieve, I don’t know when, but certainly not at 26. And through a serendipitous set of connections and hustle. And I ended up having the opportunity to photograph with Jeffrey Gettleman of the New York Times, a sort of conflict that was happening in the east of Kenya. It was a, you know, just before the Kenyan elections in 2013. And if anybody knows anything about Kenya, they had really violent elections in the four years before that. So there was a lot of sort of people were very tense. People were very concerned. We didn’t know what was going to happen. And so I went with the New York Times to shoot this conflict in the Eastern of Kenya that was really, you know, I won’t get too much into it, but it was really rooted in, in age old conflict between a group of sort of nomadic pastoral nomadic herders and sort of farmers and pastoralists. I guess is the best way to put it two different tribes in this region. And so what ended up happening is I ended up with a front page photo on the New York Times, kind of A1 front and center, you know, it was a really stark and difficult photo. It was of a, I believe she was like a seven month year old girl with a machete hack to the back of her neck. And it was in the hospital and it showed this sort of big scar on the back of her neck. And, you know, it was jarring. And, you know, it was a result of this conflict that was happening. And it, it was incredible. Like I won, I won. I mean, I had a front page for the New York Times at 26. Like life goal unlocked. Like, wow. On the other hand, what really jarred me was I had spent, you know, the previous sort of three or four years really championing this narrative against how the mainstream media portrayed Africa and against this idea of, you know, Africa is just war and famine and violence and all of this and that there’s this really beautiful side of creativity, of entrepreneurship, of, of technology. And the headline of the piece that ran with my photo was neighbors kill neighbors as Kenya’s election looms. And I was really upset because the article basically took this small conflict in a region that had been going on for a long time and made it seem like it was all of Kenya and that people were killing each other before the election. And there was just such a moral conflict of this is what happens in the media and even the New York Times, you know, even a very large, reputable, incredible organization. You know, the photo didn’t lie.
Jonathan Kalan 22:52
It was real. But the way it was portrayed and angled made me feel ashamed, you know, for all of the relationships and friends in Nairobi and all of the experiences that I’ve had in the stories that I was trying to tell.And so I kind of reached this point where it was like, well, is this the industry I want to be in? You know, is this where I’m going to have the most impact? Is this where, you know, I’m going to thrive as somebody who is very optimistic and really loves to show, really loves to inspire people, let’s say. And that was sort of the beginning of the end for me of photojournalism. Immediately after that, go ahead.
Blake Boles 23:35
You said that when you looked 10 years down the line at other people who stuck around photo journalism, you didn’t really like what you saw.
Jonathan Kalan 23:43
No, no. And, you know, there’s, like I said, there’s happy dirtbags and there’s unhappy dirtbags. And a lot of photojournalists and journalists, I think fit into the unhappy. I mean, I was 26 and sort of at the pinnacle of my career, you know, I was photographing for the New York Times, I was writing for the Atlantic and foreign policy, I had my photos and papers all over the world. And when I looked at everybody who was, you know, 36, 46, their lives were not, they’re not that great. They were wonderful in some aspects. I mean, the highs and lows of journalism, just like, you know, adventure and climbing and everything, I mean, they’re, they’re extremes, you know, they’re euphoric, and they’re highly depressing. And I think when you spend that long as a foreign correspondent or a foreign photojournalist, you just can’t avoid the things that you encounter, you can’t, it’s, it changes you, it shades you in terms of your perception of humanity. And I think a lot of people that I encountered in that space, and again, this is more, I think they’re really kind of stereotypical rugged photojournalists and journalists and foreign correspondents. They’re depressed, they’re alcoholic, they’re divorced, like, there’s just a lot of things that come with the baggage of experiencing some of the worst of humanity, while you still experience some of the best of humanity.And so, so I looked down that road and said, I don’t, I don’t want that, right? I love this life, you know, I love the process of being a photojournalist, I love that idea of going out and exploring and meeting new people and, and discovering things and contextualizing them and sharing them with millions of people to help them see the world differently. But the industry itself and what it does to you is challenging. And, you know, that really only furthered when after, after I covered, after I had the photo in the New York Times, I ended up in the revolution, the second part of the revolution in Egypt. And then I ended up in a terrorist attack in Nairobi, both very, you know, very tragic, extreme, intense, and dangerous circumstances. And kind of all that happening within the span of about a year, I just said, you know what, like this, this is, I love this, but this is, this is not my path.
Blake Boles 26:01
And this is when you re-entered startup culture.
Jonathan Kalan 26:06
Yeah. It took a while.It took about a year for me to wander aimlessly around various places to figure out what I wanted to do next. I tasted the thrill of entrepreneurialism before. A lot of the early work I was doing as a journalist and photographer was covering startups and so I always knew that it was something I’d probably enter into. I just didn’t know kind of when and how.
Blake Boles 26:33
So what was your entry point back into this this culture?
Jonathan Kalan 26:39
So I spent about a year kind of trying to process and really process those experiences and understand, you know, what, what was I capable of? Like, what was I qualified for? First of all, you know, I think one of the things when you come out of living a life like that and you know, you said like, well, what am I good at? You know, yes, I can write. Yes, I can take photos, but like, I don’t want to be hired for that. So how do I make this transition?How do I shift into something? And I, one of the things that I, I did a lot of self work, I did a lot of just kind of self study. And I came out the other end and saying, okay, did I mention this before? What drives me is not so much a purpose. It’s a, it’s a process, right? Like that process of discovering things, contextualizing them and sharing them with others to inspire them. So that led me to a mutual friend ended up connecting with a sort of fellow entrepreneur. We started to build a small media company in Washington, DC, that was going to cover a lot of the same stuff that I was covering in East Africa, but without having to travel. And then about two or three months into that, I, through another connection, ended up with this opportunity to co-found a kind of media technology company in San Francisco. And so it was like the allure of the San Francisco kind of VC startup treadmill. And I said, you know what, like in 26, 27, there’s a time to give this a shot. Let’s try it now.And so I moved to San Francisco and we built this really incredible platform that, you know, in short gave historical context to breaking news. It was called timeline and it was a really exciting company, really well-funded. So for the first time I got paid like really well. I went from making what, like maybe $20,000 a year, $25,000 a year, all of a sudden making $120,000 a year. And which, you know, living in San Francisco and living in Kenya, it was almost the equivalent of cost of living at that purchase. Yeah, exactly. But it was incredible, you know, and I loved it. And I worked myself to death. And, you know, after about a year and a half, I realized I was not qualified as a manager very well. I was a great entrepreneur and creator and builder, but I was not a great manager. And I had a lot of, I had no experience working in a company, you know, I’d been on my own for so many years that I really didn’t know how to, I think, manage others, not necessarily work with others, but I was so independent that I got in my own way and ended up basically getting kicked out of the company, which felt like a huge failure for me. Looking back, it was a great thing.Looking back, I think I really actually would have burned myself out even worse if I had tried to stay. And it was the greatest thing that happened because about two months later, I ended up co-founding a company that was really driven by my own sort of sense of purpose, my values, and what I believe the world needed and was really deeply rooted, I think, in a lot of the experiences I’d had growing up and as a journalist.
Blake Boles 30:03
This brings us back to Unsettled which you started in your late 20s and I feel like where you and I have a lot of overlap in our in our sort of mission here and also just a lot of the people I’ve interviewed on this podcast their number one challenge is community and friends and feeling feeling settled so to speak feeling like they’re rooted somewhere and you know people who have all this freedom it’s just hard to to find other people who have all this freedom and want to stick around with each other for a while so is this related to the what problem were you solving with Unsettled?
Jonathan Kalan 30:39
Exactly that, you nailed it. So, you know, around 2000, what, 2015, 16, you know, sort of the rise of remote work, the rise of the consultant, the rise of the solopreneur, you know, there was just this massive tidal wave of so many people like yourself and probably many people that you’ve spoken with who, you know, could work independently, could work from anywhere, and wanted to make that choice to work from anywhere. I mean, if you could work from a, you know, a high rise in New York City or a bungalow in Bali, like which one are you going to choose? And so a lot of people were making that choice to head off and explore and live, let’s say, the digital nomad lifestyle, but community is really hard to find when you’re moving.And so our thesis was, you know, how can we live anywhere and still have community and still have that sense of people who are challenging us to be better, people who are teaching us new things, people who are inspiring us. And we ended up building a company called Unsettled based off of that premise with this idea that like being unsettled is not a bad thing. You know, a lot of times people hear that word, especially Brits for some reason, I don’t know why, they’re very uncomfortable with the word unsettled. Americans are a little more so. But we built Unsettled on this premise that like it’s okay to be unsettled. There’s certain points in your life where you want to be unsettled, where you want to shake things up, where you want to really experience things differently. And the whole idea of the company from the beginning, it was, you know, live anywhere one month at a time with a new community of people in a new place, in a new environment, like reset your routine. So we started organizing the first co-working, co-living retreats in the world, I think.I mean, it was us and this one other company called Hackers Paradise, which were good friends of ours. And we just started running, you know, like 30 days in Bali, 30 people, complete strangers from all over the world, usually 15 to 16 different countries who were all there to, you know, some work remotely, some who are on sabbatical and just looking to connect with new people and sort of have new experiences. And we found that these things were just incredibly transformational, because at what point in your life, aside from, you know, college or study abroad, as an adult, do you really get the chance to go out and like push your boundaries and bond with a group of people that you’ve never met before and just do things completely differently? So we built the company, a crazy journey up and down, you know, from zero employees to 25 employees, to, you know, no money, to, you know, fundraising and raising, you know, half a million dollars and every mistake you could make, we didn’t make all of them, but you know, good amount. And, but in the process, just built this incredible community of over probably now 4,000 people from, you know, 70 or 80 countries who have lived unsettled and had these experiences. And, you know, it was rooted in this idea of just embracing the unknown, embracing new perspectives and new ideas.
Jonathan Kalan 33:36
And a lot of people who went out and settled completely changed their life trajectory as a result and sort of living lives more aligned with their purpose and aligned with their passion. And, you know, we had a lot of workshops and programming that we designed to really sort of help them find that path.And on the back end, we also ran adventure trips. So my passion is sailing, my co-founder’s passion is sailing. And so we also were running kind of week-long sailing trips for our alumni and keeping that adventurous spirit up. And so, yeah, it was it was incredible. But, you know, as with all good things after about six years, I also, you know, burnt out of that pretty badly.
Blake Boles 34:17
What led to that burnout?
Jonathan Kalan 34:21
I think a couple of things. I mean, one was there was, you know, I was entering my sort of mid thirties and. You know, there was some months where I was paying myself $2,000 a month. Some months I was paying myself $4,000 a month. And it was from a financial standpoint, unsustainable.Um, you know, it was, I was living the life of my dreams again, you know, just like, uh, as a photojournalist and everybody who kind of looked at me and said, wow, you’re, you’re living the dream. I mean, you’re getting paid to literally take other people traveling around the world and have these incredible adventures. And yeah, that’s, that’s incredible. But, um, you know, running your own business, always stressing. It’s not a very profitable business. Uh, um, it’s a great lifestyle business, but we had built it in a way because we took a, uh, you know, venture, not venture capital, but angel capital, which is sort of funding from people who have money to invest in smaller, uh, startups, hoping that they grow. We had expectations to grow, you know, beyond a certain threshold and either sell the company or be profitable enough to, to give dividends to our investors. And we just couldn’t find that path. You know, we, we made, you know, we were running maybe at some point, 70, 80 trips a year, like three to four or five each month. And, and we just couldn’t hit that point. And I realized at the end, like, we’re not going to hit that point. At least the combination of my co-founder and I, you know, he was very lifestyle business oriented. I kind of wanted to push it and grow it, but we couldn’t figure out how. And around the same time as all this was happening, obviously COVID, uh, through a major wrench in our plans as a travel company, we survived pretty well in the first, you know, year, year and a half of COVID, cause we had done really, uh, powerful things on the, on the virtual side of our programming.But I was just, I was reaching that point and about six months before COVID, I had happened to meet my now wife on one of our sailing trips. So I was her captain. She was a client. Um, I know there’s rules against that, but when it’s your company, you can sometimes do whatever you want. And then, and the new policy is, you know, you can date a client if you marry them. So that’s, that’s the new hard and fast rule. I think so. I mean, we’ll see, we’ll see. I don’t know if my co-founder is abiding by that rule, but, um, we’ll see. And no, so, so yeah, I met my, I met my now wife. We sort of fell instantly in love, um, pretty easy to do on a sailboat for a week in the middle of the Virgin islands. And it was just ready for, I was just ready for change. So it was a long and hard process. It took maybe honestly two and a half, three years. I, I hate really bad depression. I was exhausted, fatigued. I mean, I feel like honestly, it’s only been the past maybe six months, uh, that I feel like I’ve really honestly began to recover from, from all of that.
Jonathan Kalan 37:22
But, uh, in the end, it was a really, it was needed. I needed to let go.I needed to learn the lessons of what it’s like to build a company and put 150% of your soul into it and let it go. Um, and, and that I did, and it’s still, it’s still going. Untitled is still running, still running trips. It’s a smaller business now, but it’s, it’s a great business. And my co-founder is really happy and, you know, really happy for, for him and the company, but, um, letting go of your baby is not easy.
Blake Boles 37:53
Yeah, I have a little bit of experience in this department, Jonathan, but I’ve run my adventure trips only once or twice a year since it started in 2008 and never had angel money or any outside investment. And the pay that you described paying yourself is pretty much ballpark what I’ve paid myself since, you know, a few years after the first growth phase. And so I had no one breathing down my neck and I had no co-founder and I was able to just like decide each year, is it something that still feels like a good deal to me? And I’ve been able to continuously say yes to that, although it may not be too much longer either.So I vibe in summary and it seems like, you know, life is this, is this ping ponging between different intense gigs. I can see why you have this startup energy. It’s like you want to like go in and rapidly make something happen and take chances. And then like, as soon as it slows down or as soon as you start burning out, it’s like you then kind of ping pong over to the other side of the work world and you find a different but similarly intense opportunity. Am I describing you accurately?
Jonathan Kalan 39:19
100%. Yeah, and it’s something I’ve, I’ve learned about myself pretty recently, you know, the past, you know, three years, I think has been an insane period of just personal growth. And, you know, on all aspects, let’s say from, you know, two weeks in the jungles of Peru to, you know, therapy to everything. And I think, you know, that process was needed for me coming out of living such an intense lifestyle where it was that ping pong. And it was always, you know, I always gave 110%, 150%, you know, dive full on into things. And cool, that’s great. You know, in your 20s, like you can do that. But I think as you get older, it takes a toll, it takes a toll on your body, it takes a toll on your mind, and you have to learn balance.And that sense of balance, that sense of, okay, I can, I can give something 100%. I don’t have to give it 150% all the time, you know, sometimes you can give it 20%. Sometimes, you know, and, and I really had to sort of evaluate my work, my life, that balance, because I, you know, I was a super workaholic. And in part, because I loved what I did, like, I was just so I mean, I, like, I wanted to go out and photograph all the time, I wanted to build our company, I wanted to find more, you know, clients to go on incredible trips with. And so, you know, that that drive to build, to create, to add value to society is deep within me and has always driven me. But at some point, you know, you have to take care of yourself. And while those things certainly fulfill you, and they did fulfill me, that idea of just slowing down and pausing and resting and, and sort of not always being on the, on the edge of risk, because like our nervous systems, I mean, entrepreneurship is risk every day, if you don’t know if you’re going to be able to support your company and support 25 people, or as a journalist, if you don’t know if you’re going to be able to feed yourself, or you don’t know if you’re going to be able to be in a, you know, survive a dangerous situation, like you’re just, it’s that same pressure on your on your system.And I think, kind of stepping back from that, I really tried to learn how to release and relax and the past two companies I’ve worked for where I sort of come in at a very early stage, they weren’t my companies. So I had to learn how to treat them as not my companies, which, you know, takes a bit of time to not have that sort of entrepreneurial drive to own everything and fix everything. But the last two companies I’ve come in and really helped them in that early stage. And then let you know, the last one, I was able to let go kind of after they got to that stage and feel really good about it. And then this one, I’m taking a little bit more of a gradual approach. And I may not let go, I may stay with them for longer than I anticipated, because I really enjoy working with them.
Jonathan Kalan 42:11
But I’ve learned how to balance, I’ve learned how to, you know, turn the computer off at six o’clock or seven o’clock, I learned how to take days of rest. And so I’m trying to avoid that ping pong or at least having that ping pong, you know, cross the Grand Canyon and maybe more to, you know, the size of a ping pong table.So it’s not so extreme.
Blake Boles 42:32
Well, we’re just going to breeze right past the fact that you went to do some work on wall street for a while after leaving unsettled, but that’s not exactly known for its work-life balance. Um, but I just want to fast forward to like your, your reality right now.So you’re a startup consultant and that can mean many different things. Like what’s your specific superpower in this startup world? What do you offer that, that, that these people can’t find elsewhere easily? Yeah.
Jonathan Kalan 42:59
I love building brands. I love building community. I love getting people to fall in love with an idea, a product, or concept, and that’s something I’ve always done, you know, and that’s something I felt like I did really well and unsettled is just build this brand that people would see unsettled and go, oh, yeah, like that clicks, I get it. Um, and so what I’ve discovered my superpower is, is really this idea of how do you, how do you build a very, um, strong brand message, um, and communication strategy for an early stage company, one that is probably pre-product or early product or, you know, just kind of pre revenue, early revenue, which is typically seed stage. And helping them form that brand, that identity, and most importantly, that community.And that’s manifested itself in transforming, let’s say, a community of supporters into crowdfunding, into pre-orders. So it’s just, it’s really like this kind of zero to one, zero to two stage of a startup and covering everything from marketing, brand communications, customer experience, pre-orders, crowdfunding, like all this idea of how do you turn community into customers and also customers into community. Which ties together my community working on settle, which ties back to my kind of journalism work of storytelling. It sort of brings a lot of my, my passions together. And as soon as it hits that point of, okay, it becomes, you know, optimizing performance marketing or, you know, routine customer service. Like that’s the point where I go, cool, not my thing. I’m not an operator.I’m a builder. And, um, recognizing that that’s the point that is sort of my limit. Um, whereas in the past, I’d normally go past that because, you know, my, my self-worth was often very tied to my work and very tied to what I was doing. And now I can say, no, no, I feel very comfortable in what I’m able to add at this certain stage. And I’m very comfortable saying, great, you guys can move forward. Now I’ve, I’ve, I’ve built things to this sort of level of stability. Um, and I can let go. So that’s where I feel like I found my sort of groove for now. Um, who knows where it’ll be in five or 10 years, but, um, yeah.
Blake Boles 45:14
Yeah, seriously. So you you come in, you kind of build the fire, you position the kindling underneath, you knock some some rocks together, throw the spark under there, blow on it. It gets going and you’re like, peace, I’m out of here.Someone else can tend the fire. Exactly, that’s a great
Jonathan Kalan 45:33
It’s a great way of putting it.
Blake Boles 45:34
How do you balance time, money, and purpose in your current situation? How much do you work for money? How much free time do you actually enjoy?And do you feel like you’re really doing something purposeful and meaningful when you’re playing this fire starter role with early stage startups?
Jonathan Kalan 45:53
Yeah, so I think I’m very particular about the kinds of companies that I work for, Wall Street being that exception with that brief little sabbatical that I had, which I wasn’t on while I was still working remotely and I was a consultant, so I was not in the fire. But where. Where I where I balances is, you know, the last company I worked with kind of in this capacity was building a smart bird feeder, which basically means it’s a bird feeder with a camera that takes photos and videos of the birds in your backyard and send them to your phone and for me, like, that’s a beautiful way of connecting people to nature in their own backyard. It’s a great way of teaching people about biodiversity, about nature, like, I’d much rather get a notification of a bird than, you know, my Twitter or Facebook or whatever else. So I was passing by and I was like, well, that’s a great way of connecting people to nature. I was passionate about that because it was just connecting people to nature and I got paid really well for that job. I ended up being full time with them for about a year, but I kind of burnt myself out. You know, I was working at six o’clock in the morning because most of the team was in Slovenia and I was in Mexico City. So I had calls from six a.m. to, you know, noon. And by the end of that, I was just I was done. I was toasted. I couldn’t go out. I couldn’t experience my life here in the same way. And so after a year, I said, great, like I made good money, but I was not feeling good.I was not feeling healthy. I was exhausted. And they had also reached a point where, you know, they I felt like they didn’t need me in the same way. They had already started to ship the product and they were kind of moving into more scaling. The fire was burning. Fire was burning. Fire was burning. And I and I found that it was a good time to step out. So I did. And the next opportunity I took, I decidedly only wanted to work halftime for the first year. And I said, look, this is how much money I need to feel like I’m being taken care of. It’s not enough for me to save, but it’s enough for me to live my life for me and my partner in a sustainable way, not in the long term, but let’s say a year or two and live our lives in Mexico City. And I intentionally said I only want to work about 50% of the time because I don’t want to burn myself out. I don’t want to get over involved. I want to try to curb those tendencies to kind of get my tentacles and everything and fix all the problems. And I stuck to that. And it was really, really healthy for that for that first year. And the company had been wildly passionate about it. Say we’re building an AI powered mobility device for the blind and low vision communities. So you can think of it as like a self-driving stick in a way for people who are blind or low vision using the same kind of technology as self-driving cars. And so it gives people who are blind the ability to actually move independently and many times for the first time in their life because 97% of people who are blind or low vision don’t use canes or dogs.
Jonathan Kalan 48:54
There’s very few dogs available for people. And just the technology is really not nobody’s developed it for this community. And our founder is blind himself. And it’s just an incredible project and incredible company.And so I’m excited because I’m learning about a whole new perspective of people who navigate and live in the world without sight. And I actually just recently, about a month ago, switched to full time. And I felt like I had done the halftime for a year and kind of found that balance and found that rhythm and found that I could prevent myself from going too deep and take my time. And now I feel like, okay, I can go to full time and not stress out about it. I can get paid what I feel like I need to be more than comfortable. And then I’m doing something I’m passionate about. So really, for the first time in a very long time, I kind of feel like I’m nailing all three. I don’t want to jinx it. But I do feel in a really good place with that.But again, it’s 37 years of learning and experimentation to get there and nothing’s forever. So this could last a month, a year, 10 years, and you don’t know.
Blake Boles 50:12
I guess I’m curious if you really feel like you can push down on the gas pedal and then hit the brakes when you need to with your current work, or is it more like a certain opportunity presents itself, it’s either full-time or nothing, and even if you’re not really feeling it, you’re like, well, this is a better opportunity than doing nothing else. How much real flexibility do you have in this position as a startup consultant?
Jonathan Kalan 50:38
Yeah. I think it’s, it’s always, it’s always negotiable. Honestly. I mean, that’s what it comes down to is you set the boundaries, you set the ground rules, you know, you, you know, how you work best. And some people that takes, that takes time to figure out, you know, what, what does it mean to work at your best? Are you, do you work best in the morning and the afternoon at the night? Do you prefer that you need a two hour nap in the middle of day, which I’ve gotten in the habit of doing like everybody, if you don’t know your, how you work at your best, I encourage everybody to take some time to figure it out.And then it’s a conversation with whoever you’re working with saying, you know, I went into that job saying, listen, you know, I’ve got, I’ve got some health issues. I’ve had, you know, a number of surgeries in the past couple of years, mostly just like my body chronic pain from the life I’ve lived. So I’ve had, you know, hip surgery and neck surgery, shoulder surgery. And I really wanted time and space to recover and not stress myself out and not burn myself out. And I was very honest and transparent with the CEO. And I was like, listen, I want to be half time and I want to be flexible, which means I’m going to set my own, you know, I know what I need to get done. I’m going to be clear about what I need to get done and I’m going to get that done on my own time, but I’m going to be a collaborative member of the team. You know, like I will be online almost every day. I don’t want to take a lot of calls because I don’t want to, you know, have to have a, be tied to the desk all day. And so it worked out really well. It’s just being transparent. And, and even now that I’m, you know, so-called sort of full time working with them, uh, as a consultant, they know, you know, that, that there’s times that I’m going to be unavailable. There’s, and that’s okay. Um, and I think you just have to be open about it and transparent. And don’t think that just because what a company or, or employers says has to be the way that it is, you know, if they value you, um, you can find that flexibility and just, just be open and honest.
Blake Boles 52:33
I agree and you’ve also told me that you think hustle culture is bullshit and that it really does not address the question of what is enough and when is enough enough and that you believe you can have a small business and still have a great life.It sounds like you believe these things in spirit and you’ve also struggled to act to live these values in your own life because you like hustling and you’re good at it and you get rewarded for it both financially and socially and it just makes you feel like you’re alive so talk a little bit about this tension you know kind of looking at the excesses of hustle culture and saying I don’t want that I don’t want to be burnt out again and then also being energized by it at the same time.
Jonathan Kalan 53:20
Oh, man, so many things, so many things come to mind with that. Like, I mean, I think number one, I’ll start with just general hustle culture. Like, hustle can be great. Like, hustle is how great companies are born. It’s how great things happen. You know, whether it’s a creative hustle, an entrepreneur, it doesn’t matter. Like, hustle is great. But I think what’s wrong is the narrative that hustle culture is essential to success. And the only way to succeed as a as an entrepreneur or freelancer is is 24 seven hustle. And I think that’s bullshit.And I think, you know, this idea of like, you have to give everything your heart and your soul and and and kind of all of your energy and time to build a billion dollar company that’s VC back. Like, that’s bullshit. There’s so many great medium sized companies. There’s so many great lifestyle companies. And I think for people who want to sort of set out on their own and have that flexibility in life, like you can make good money and and build something and make it purposeful and make it a size that works for you if you know what is enough for you. And I think that point around what is enough is a really important for question for people to ask themselves. You know, there’s a lot of entrepreneurs out there who like this idea of this narrative of I have to build a billion dollar company. But like when you ask them, be like, no, no, I’d be I’d be happy making, you know, I don’t know, four hundred thousand dollars a year and having equity and exiting at, you know, five million dollars. And like, yeah, that’s that’s enough. But for some reason, they’re driven to just go more and more and more. So I think defining what is enough is is really key.And for me, you know, I did hustle and I hustled not because of hustle culture, but because I just loved it. And I did it until my body couldn’t take it anymore. And like I said, like I just hit a point where I was depressed. I was chronically fatigued. Like I was just I couldn’t like I could barely work. And so like reaching that level of burnout, I think teaches you like, OK, so I I can’t do this all the time. Even though I love it, it doesn’t it doesn’t work. And it took it. It wasn’t my brain actively saying, oh, no, no, hustle culture is bad. It was my body physically telling me that like I could not. I could not keep up with the life that I was living. And, you know, I was on the road. We talk about living. I was, you know, I wasn’t in one place for more than two or three weeks at a time. For years and years and years. So I hit that point. And now I feel like I know what what’s enough, you know, for me, like at this point in life, let’s say if I’m making one hundred and sixty thousand dollars a year for me, that’s enough. You know, if I want to make three hundred thousand dollars a year, if I want to make five hundred thousand dollars a year, I would know that I would have to like double down on my hustle, like go full on.
Jonathan Kalan 56:10
And maybe at some point there’s a risk reward scenario where I could do that for a year if I feel like money is driving me. But but, you know, like if I make, let’s say one hundred sixty K, like I am saving plenty of money. I feel secure about my future. I feel I feel like that is enough.I can get by with sixty K. I can get by with eighty K and I can survive and that’s fine. That would be enough for me if I really wanted to work 20 percent of the time or 50 percent of the time. So I think it’s just kind of figuring out this equation of if you’re somebody who wants to take off for six months and adventure and explore and how much money do you need to do that? And so maybe you have to work really hard for three months or four months to do that. It’s a scale and it’s flexible, but it takes defining what enough is for you at this point and at a later point in life to be comfortable, you know, and my level of comfort ten years ago of living in a kitchen cupboard is different than my level of comfort now at 37, you’re living in a beautiful place in Mexico City with my partner, like different life stages.
Blake Boles 57:16
Seems like it really requires a certain level of being antisocial in the sense of just you know you can always find someone else who tells you you need to make more money or like you could be doing better or you could have a more incredible life and at some point you just need to say no to these people or say just no thank you that’s for you it’s not for me. A bit of a curmudgeon just a bit.Last thing I want to talk about Jonathan you your body is clearly still working to a good degree because you and I barely missed each other earlier in 2024 when we both rode bikes through Patagonia on the content of Australia and you were a bit further and I did that in January actually one of the first people I interviewed for this series Hannah Bowley was one of my writing partners and you did it a bit later and I believe you had a slightly colder experience than I did maybe you can just talk we can swap some notes about the riding bicycles on the car to Australia what was your experience like
Jonathan Kalan 58:21
Well, I think similar to you, we both wish that we had way bigger tires.
Blake Boles 58:26
Oh my gosh. Biggest regret, hands down.
Jonathan Kalan 58:30
My god, yeah, the ripio there, the gravel is horrible. So yeah, oh, man. So, you know, am I and this is kind of that, like, I don’t know, I never want to lose the adventure spirit, but I never want to lose that dirtbag feeling, you know, and I think I found a partner who is equally happy in a corporate boardroom, you know, advising a family office that she is, you know, barefoot on a beach or in a forest living in a hut, you know, and I think it’s very lucky to have found that right, like, we can live rich, we can live poor, we can adopt however we want to, and make that choice.And so, you know, I think we felt pretty itchy, we felt like, okay, we’re, you know, we’re settled into our place in Mexico, like we’ve kind of nested and found a home, let’s shake this up. And so literally a month before we went to the cartera, we, we didn’t know we were going to go, we had a friend who was like, Hey, you guys are both kind of in transition right now, you should, you should just go do something crazy. And I was like, well, I wanted to bike Patagonia. And so with basically a month of prep, we just got everything together, went down there. And it was, I mean, incredible. So yes, bigger tires would have been amazing road bike tires suck on gravel. It was we started off as 12 days of freezing rain. Delightful. Which, again, like, it was, it tricked us. The first day was stunning. It was like, Oh my God, this is amazing. And then just like downhill. So yeah, freezing rain. My, my wife accidentally left my dry bag open with all my clothes on the first night. So from, from day two, everything was soaked and just did not dry. And anyways, it was, I mean, but, but that journey was just incredible. So we had a couple days of really phenomenal weather that were worth all of it. And even the total type two fun, like even when I look back at being frozen and wet, I was like, there’s no place I would rather be absolutely no place I’d rather be than, you know, freezing in a tent in the middle of, of Chile and Patagonia.So yeah, it’s when we hit the snow at the end, because we made it all the way from Puerto del Thales to Punta Arenas. And on that journey, it was basically like blizzarding one evening. And we’re like, I think we’re good. I think we should turn back. And so we ended it there. But I do want to continue the rest. I want to go to Ushuaia. So if you’re, if you’re planning to continue that route, man, I’m in.
Blake Boles 01:01:07
Well, I think you are clearly someone who lives for intensity, Jonathan, but you also know how, how to call it quits when you need to call it quits. Yeah. Thanks so much for coming on the podcast.
Jonathan Kalan 01:01:20
Yeah, thank you so much Blake, it’s been a joy.