Adventures with Cyrus “Scooter” Anderson: Seven Summits and Beyond

Guest Bio:

Cyrus Anderson

“Scooter” Anderson grew up near Jackson Hole, Wyoming, deeply immersed in wilderness, often living in a sheep wagon or teepee, fostering an early connection to the natural world. His career path included economics, finance, and diplomacy before he chose extensive global travel and exploration via motorcycle and mountaineering. His ambitious “2 Wheels 7 Summits” project sought to link the Seven Summits by motorcycle, showcasing his preference for lightweight dual-sport bikes, like the Husaberg FE 570, on difficult, unconventional routes. Today, his focus is on fatherhood and exploring the intersections of adventure, resilience, health, and nature.

Scott Brady

Scott is the executive publisher and co-founder of Expedition Portal and Overland Journal and is often credited with popularizing overlanding in North America. His travels by 4WD and adventure motorcycle span all seven continents and include three circumnavigations of the globe. His polar expeditions include two vehicle crossings of Antarctica and the first long-axis crossing of Greenland. @scott.a.brady

Year Two of The Big Thing Is On!

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Transcription:

Scott Brady: [00:00:00] Welcome to the Overland Journal Podcast. I’m your host, Scott Brady, and I am here with Cyrus “Scooter” Anderson. Longtime friend. This is awesome to have you on the podcast with me today. I mean, we have known each other, it’s gotta be close to 20 years now.

Cyrus: Yep. OR show, he just, uh, so fortunately found a motorcycle that was identical

Scott Brady: to mine.

Yeah. Yeah, that’s right. We had a, we had a mutual love for KTMs at the time. And, uh, just for the audience, one of the things that I have always so enjoyed about you is that you have found a way to dive in professionally for a chunk of time, and then you exit out of whatever it is that’s of interest to you at that point in time, and then you go off and you see the world.

And you’ve done some incredible adventures. Maybe we’ll just kinda kick it off with what do you think was w- your most ambitious of all of your, of all of your trips? Just to [00:01:00] give the, the context. ‘Cause you had, like, that seven continent- Yeah … seven summit idea. Like, let’s talk about … Oh, and then let’s introduce your son here.

Cyrus: Who are you?

Cyrus son: Cyrus.

Scott Brady: Hey, Cyrus. Thanks for being on the podcast, buddy. Welcome. You, you enjoying, uh, doing a road trip with your dad?

Cyrus son: Yeah.

Scott Brady: That’s n-

Cyrus son: Yeah. Um, last night, uh, I ate so much that my tummy was so big-

Scott Brady: Yeah …

Cyrus son: that I had to stay up till, like, 1:00.

Scott Brady: Yeah, that’s me mo- most days, buddy.

Cyrus: And don’t forget, you wanted to just go camp in the middle of nowhere last night when you had a nice place to be.

Scott Brady: He’s got it- Then we went

Cyrus: on the side by side … in his blood.

Scott Brady: Do you know how cool your dad is, by the way? No? Thumbs down. I don’t know. It’s pretty … It, I, I get it, man. At your age, it’s pretty hard to know how cool your dad is, but your dad is really cool. He’s done a lot of travel around the world. And- Just a bag of bones.

What

Cyrus: movie did you [00:02:00] steal that from? Talladega Nights, huh? “Kip, you

Scott Brady: ain’t nothing but

Cyrus: a bag bones.”

Scott Brady: You know, we’re all just a bag of bones. Trying to make it work, huh? So tell me, tell me about your favorite trip. Where’s your favorite adventure been?

Cyrus son: This one.

Scott Brady: This one? Yeah? And, and if I remember, you’ve already been to South America.

Where else have you been in the world?

Cyrus: Hey, you lived in Taiwan. Yeah. We had a Delica van. India.

Scott Brady: Oh, nice. In India? Nice.

Cyrus: Well, we’re about to go to Canada this summer.

Cyrus son: Yeah.

Cyrus: So it’s, uh … Yeah, we’ve had some good little runs. It’s been a lot of domestic stuff. Tell ’em about, like, last summer when we went down the river in Idaho, and then you, you hitchhiked our way back up with a jet boat.

Cyrus son: Yeah. Tell them that. That was, like, half a million dollars.

Scott Brady: Quite a suite. That, that’s, that is a pretty sweet jet boat. It was rad than hell. Well, do you, do you have some advice for people that are getting started in travel? What, what advice would you give to, to people about traveling?

Cyrus son: [00:03:00] Never- Ever give up

Scott Brady: Never, ever give up.

That’s a good one. That’s a good one You’re

Cyrus son: always chasing dreams

Scott Brady: There you go. Do you feel like you’re chasing your dreams, buddy?

Cyrus son: Not yet

Scott Brady: Yeah, you’re going to though. I can see it in your eyes. You’ll- You’re

Cyrus: living your dreams

Scott Brady: Oh,

Cyrus son: no, I’m

Scott Brady: not.

Oh, that’s cool. And what would you have in the building?

A horse?

Cyrus son: A cars.

Scott Brady: Cars, got it. Okay, no horses, cars. With

Cyrus son: lots of horsepower.

Scott Brady: Yeah, okay, that makes sense. I could see one… I mean, I think that’s pretty much everybody… most of the people that I know, their dream is to have a building with lots of cars with lots of horsepower.

Cyrus: He is all about horsepower.

Speed, baby. Yeah, he wants to go fast. What do you think, Sy? Do you have any other adventures you wanna share? [00:04:00] How about snow cave camping? How about boats?

Cyrus son: Can I do a shout-out to bo- two people?

Scott Brady: Yeah, you should do a shout-out.

Cyrus son: Sure. A shout-out to my dad and mom.

Scott Brady: There we

Cyrus: go. For

Cyrus son: being the best mom and dad ever.

Oh.

Cyrus: I

Scott Brady: love that. We

Cyrus: love you, bud. We’re proud of you.

Scott Brady: I love that. Well, I think that’s, I think it’s pretty cool that you’re on a road trip with your dad.

Cyrus son: Yeah, and if my mom was here too, that would

Scott Brady: be- Yeah, that would be pretty- We could all do it … uh, be pretty awesome. You guys could all do it together.

Cyrus: I’ll tell you, he, uh, he, he, when he was born in Argentina, he got dual citizenship, right?

So he has a tie to there, and he was on the front of a motorbike one of the first times with me, just buzzing around and about, and he says, “Keep going. Keep going,” very end of it. He’d already planned out a 14-day motorbike trip with Mom and Dad- … through Argentina, and where we were gonna go.

Cyrus son: I didn’t plan

Cyrus: that.

Well, anyway. [00:05:00] You don’t think so?

Cyrus son: I did not plan that.

Cyrus: Okay, I guess you didn’t plan it out. What did you plan

Cyrus son: out? Nothing.

Cyrus: Okay, never mind. I guess it

Cyrus son: was all a figment of my imagination.

Scott Brady: You didn’t tell me I had

Cyrus son: to plan out something. Yeah.

Scott Brady: I’m not trash, idiot.

Cyrus: Okay.

Scott Brady: Good job, buddy.

Cyrus: Yeah, nice work, bud. Thanks for saying hi, and you can say hi longer.

He was asking some j- I don’t know if you know about some of the trips Dad’s been on that you see photos. You always wanna go to our, um, adventures, and there were also adventures I did before you came along. Can you believe that? Can you believe that? Scott was asking about one of them

Cyrus son: If you slow Go faster

Scott Brady: There you go.

That’s good advice.

Cyrus: We’ve now watched Talladega Nights, I

Scott Brady: bet 15 times. It, it- Yeah … there’s some evidence to that. Okay. Does that sound pretty good?

Cyrus son: Yeah.

Scott Brady: [00:06:00] Yeah.

Cyrus: Are you the first kid on the Overland Journal podcast do you

Scott Brady: think? He’s one of the first. Okay, man. We’ve only, we’ve only had a couple- Okay … a couple kids on.

We need to have more for sure, ’cause kids know a lot more than-

Cyrus: Imagination, what we forget,

Scott Brady: right? Yeah. I know. And yeah, I mean, like what a, what a great reminder of, like to him, the trip that he’s on is the best trip he’s ever done. And that- Absolutely … how many times have I screwed that up? Where either- Right

I’m thinking about a trip that I did years ago, or I’m already imagining the next trip that I’m gonna go on and not- Yes … being present- Yep … in the one that I’m currently enjoying should be enjoying. So, uh, good, uh, good reminder there for sure. It

Cyrus: really is. And, uh, I’m excited to see it continue rolling on.

I’m curious what direction you’ll send us out of here even. Yeah,

Scott Brady: there’s lots of places to go.

Cyrus: We’ve already done kind of the trains, planes, automobiles getting here, right? Out of Seattle, onto the plane. It was literally a $44 ticket straight into here, right? Amazing. So we just kind of red-eyed nighttime and, um, I forgot [00:07:00] our gazetteer books of course.

So I’m gonna hit those up, grab what I can, and then we’re, we will just see, right? It’s, it’s whatever you’re led to. Yeah. We’ve got a number of friends and places, and those places we don’t know yet, and that’s the element that I guess we’re going

Scott Brady: for. Well, and it, and it seems like it’s about time together.

So it really- It is … doesn’t matter where you end up, so just having- Oh, yeah … having’ a little adventure together. But, well, let’s dig- Yes … one- let’s dig in a little bit into- Sure … you know, what, what kicked you off on that kind of seven continents, seven summits idea? Sure. ‘Cause that was, I mean, that was… I remember that being so inspiring to me of like, wow, you’re right you should dream big.

You should dream as big as you can. And how far did you get into that project and- Sure … what did you experience along the way?

Cyrus: Uh, it was around the time I met you that I was a year out from conceiving the idea.

Scott Brady: Yeah.

Cyrus: Um, it was originally when I’d resigned from A.G. Edwards and was 80-hour [00:08:00] weeks into iBanking, had a transition in life going in terms of, uh, you know, partner from Europe who’d, who’d gone back home and I was thinking, “Well, what is it I wanna do?”

Scott Brady: Yeah.

Cyrus: And I strapped a old low backpack I’d gotten when I was about 13 years old, it was already starting to get crusty- … on a number of different bikes, and, um, ended up through the Americas, Africa, you know, everything from KLRs to XR600 was an amazing bike that, that, uh, needed some valve work toward the end because of some foolish decisions on oil changes- Sure

in Bolivia. Um- and then, you know, again, like the tried and true in Africa, things like that. And, um, along the way on that XR, I ended up around the base of Aconcagua. I had a killer Feathered Friends bag that I had gotten on a pro deal years before running this outdoor program at s- university I went to.

And I said, “Hey, with a good bag, you can kinda do what you [00:09:00] need,” right? “Let’s just see here. We’ll, we’ll make the gamble, and I bet I’ll figure this out.” Because I didn’t have the best tent, and, uh, anyway, I, um, make it to where I purchased half a mule of food, right? Like medio mula, and, um, roll into base camp first night, there’s a Taiwanese guy.

He’s going to climb the Seven Summits for a company called Ottunas that he called the Coleman of Taiwan,

Scott Brady: right? Okay.

Cyrus: And he, he’s on that journey. He starts scoffing at me. “Look at your equipment. How do you think you’re gonna make it to the top of this mountain with good sleeping bag, but three-season tent and no summit jacket?”

Scott Brady: Yeah.

Cyrus: And I looked at him, and I’m not a big guy, but he’s… Well, actually, now that I think about it, he’s probably about as tall as I am. But I gave him this kind of like, “Okay, skinny guy- Yeah … how are you getting all that gear up the mountain?”

Scott Brady: Yeah.

Cyrus: And we teamed up, and I helped him get stuff up to some of the higher camps shared resources.

I found a jacket and made it to the summit of that mountain with [00:10:00] him. And he made a really cool article in a Taiwanese climbing magazine that was, “I met this American. He says he’s gonna climb this, but how’s he gonna make it?” And I guess my response was, “Because I’m cute.”

Scott Brady: And

Cyrus: he made that the theme of the beginning and end of his article.

Yeah. It came together really nice, right? Tai- Taiwanese people later, we went and, uh, when Sy was nearly a year old, his, the family, we went and spent the winter in Hualien City, Taiwan. I call it Hawaii, New Zealand, China, and Japan gave birth to a baby island, right?

Scott Brady: Wow.

Cyrus: It, when you had the revolution, all these people who head there that have a very interesting philosophy on how life can be lived.

Mm. I think there’s a really interesting respect for autonomy, for, uh, certain things that I value. And anyway so we climbed that mountain, and he told me, “Well, what, you, what, come up with something fun. You love this stuff.” And I said- Yeah … “Well, has anybody tried to ride all dirt between the highest point of every continent in an inter-year [00:11:00] adventure?”

And, uh, that’s where I suppose it was conceived. And, uh, you were honestly a very large inspiration in keeping it going, right? That, you know, the budget was huge. Yeah. Um, the push to continue, but also so huge that you gotta have the right sponsors and different things. Mm. Um, so at the time, I was, uh, jumping on a lot of, uh, 525s.

And, and I had gone to look into pit crewing and spending some time with friends at, with Rally Pan America, the only American team that was doing Dakar when- Yeah … it was what I viewed as Dakar, right? Sure. Like real Africa. And I built that bike out where it had more sustainability for long-term travel,

Scott Brady: Yeah, I remember you upped the oil volume and stuff like that.

Yes. Yeah.

Cyrus: And that actually was the 570, so I stepped then next to this 570 motor that, of course, now we know is legendary in terms of thousand hours, don’t even check the valves.

Scott Brady: Hmm.

Cyrus: And with the oil capacity thing you’re [00:12:00] mentioning it doubled the oil capacity, I believe nearly, through the frame rails, and I consulted with a lubrication sp- uh, consultant who did things for Honda and KTM out of California.

And I was curious about some of the, the, how, how the loop of oil was actually circulating appropriately. Hmm. But it did help, and it also… It’s one of those things with any vehicle. Why not tap a area that you could dump three, four liters of oil

Scott Brady: in-

Cyrus: Mm-hmm … if something goes down, and you could always drain it later.

Scott Brady: Yeah.

Cyrus: Sure. So it gives you options. But yeah, so I, uh, I started building that bike out and had access to a pretty good machine shop at a friend’s Telemark binding company, a CNC machine and lathes. Yeah. And I modified some things, integrated it, and a lot of it came into that article that I’d love to make accessible again- Yeah.

Yeah … one day. Sure.

Scott Brady: That

Cyrus: I thought toget- came together really well.

Scott Brady: That was a great one.

Cyrus: Yeah. That, that was wonderful. And I had gone up t- to Alaska actually on four wheels and kind of a combo of four wheels and two wheels a [00:13:00] overbuilt 7.3 Powerstroke van that I think it weighed, like, 15, 14,000 pounds- A lot of them do

Scott Brady: in the front. A lot of them do.

Cyrus: Oh my God, it was burning rubber, but that thing was fun. It had the front and rear winches and front and rear lockers. Yeah. Sure. It was great. And, uh, I anyway ended up trying to integrate that part of the trip as, like, the beginning of then heading south and back to South America.

And around that time, it was the fall after I met you, I also had a head-on collision with a I won’t name the company, but a major carrier.

Scott Brady: Oh.

Cyrus: Their big vehicle on the highway. Yeah, sure. They weren’t watching. And, um, I tore some rhomboids in my back, and it took me about a year to get back on board with certain adventures.

Scott Brady: Sure.

Cyrus: And later guided a friend up Aconcagua, and we got stuck in a storm for a number of days. And I… So I was doing different sections of that trip, one of which I took the Husaberg 570. Safari had hooked me up with some [00:14:00] big tank systems. Mm-hmm. That was at, like, 8.1 gallons on four separate tanks.

Scott Brady: Wow.

Cyrus: The integrated oil system you know, some, some really cool things. And I went south that trip only into the center of Central America and had a very interesting trip back up in that my timing was that, “Okay, go home on this trip, come back.” And I wasn’t permitted to leave what became international space for five days with the bike- Hmm

as they, I had some very interesting extortion occurring with- Hmm … abogados, the attorneys- Yeah, sure … of the border that wanted some payouts. And anyway yeah, that trip, over time it, it fizzled. Yeah. But the ambition was there. Yeah. Um, and it’s not to say it couldn’t be completed, you

Scott Brady: know? But one of the, one of the mount- one of the most incredible mountains in the world, I, I did not climb at Aconcagua, but I do remember driving over the Andes, and there’s that one road that you can take between Argentina and Chile where you can see the summit if- [00:15:00] Yes

the, if the conditions are right. And I just remember seeing that, and I’m like, “That has got to be one of the most beautiful mountains on the planet.” Yes. And it is known to be one of the most beautiful of the seven summits. Uh, just, you know, it’s like that perfectly shaped peak,

Cyrus: it is. And imagine being up, even spending days acclimatizing at, say, s- 18,000 feet roughly, where summits roughly right under 23, right? And you’re looking down at the globe.

Scott Brady: Yeah.

Cyrus: At a level. And those sunsets are something that’s such magic.

Scott Brady: Yeah.

Cyrus: And, and I’ve never witnessed, uh, something like what is up there at the r- the right day, the right time.

Mm. You’re just in the biggest, puffiest jacket.

Scott Brady: Yeah.

Cyrus: And, uh, yeah, those, those mountains are magical. And, just that, that combination of things, and I don’t know if you had seen, it was actually around the time I had gone for the second trip on Aconcagua, they did take the Husaberg 570 to the highest point that a [00:16:00] motorcycle has made it-

Scott Brady: Ah

Cyrus: on a little expedition. I’ve spoken with a number of them, and we were talking about trying to get some fuel-injected bikes higher than the current world record.

Scott Brady: Right.

Cyrus: Of course that-

Scott Brady: And, and did they, did they go high on there’s those, uh, volcanoes in somewhere in South America that they use to do those high altitude-

Cyrus: Yeah.

They did actually one of the peaks very close to Aconcagua, but those volcanoes you’re talking about when I came through on the XR600 I definitely had some vinegar in me. I was 26, 27- Sure … overworked, passionate about, you know, transition in life and where you are, right? And I took that XR as far as that jet would permit.

Hmm. The higher altitude jet. Yeah. And my guess is it was close to- 18 and a half? I don’t know

Scott Brady: That’s very high. Yeah

Cyrus: And that became a really painful experience in the sense that I ate alpaca meat in the nearby village. They- Mm. It was off-season, and they permitted me to, um, go with a radio and actually lent [00:17:00] me the hard boots I needed and the crampons alone, but there was one check-in- Mm

with a radio. And at the time, my Spanish had not advanced as, as, m- has in recent years, and I didn’t want to make them worried, but I… That rotten alpaca meat-

Scott Brady: Yeah …

Cyrus: gave me some serious squirts on the mountain.

Scott Brady: Oh, no. Oh, man. And I was

Cyrus: leaving what looked like there was some sort of cow that had

Scott Brady: died up there.

They would’ve found you.

Cyrus: They, they would’ve found me. Exact- I never thought of it that way. Yeah. They would’ve, and that summit was right at 22, and I remember hitting 21, and I was getting a mix of cerebral and pulmonary edema, which I’d had minor versions of at different times- Mm … and once helped off of, uh, the Grand Teton, because I was a little too ambitious leaving sea level.

Scott Brady: Yeah.

Cyrus: And had friends that weren’t. And, you know, the most painful of the two is cerebral-

Scott Brady: Yeah …

Cyrus: of course because your skull is expanding, and you- Mm … can hear crackling. Anyway I got down lower, and, and it felt like, uh… You ever see the movie Touching the Void?

Scott Brady: Oh, yeah, yeah.

Cyrus: Completely. It was a little like [00:18:00] that in the tent, because I got back, energy was low.

Somehow loaded the motorbike and got down and out of there, and, um, yeah. The village, though, returning, there still wasn’t good meat.

Scott Brady: Yeah.

Cyrus: You know, good food in general. And I had to load up again. And yeah, Bolivia at that time was one of the more, um, chaotic countries I’d spent time in.

Scott Brady: Yeah, it’s still fairly chaotic.

Yeah. Difficult to get fuel and all kinds of stuff. Maybe not so bad on a bike. They probably take some- You know, some care of motorcyclists that come through. But people that are driving through in a truck, you can… It can be hard to get fuel in that country.

Cyrus: Yes, and good quality products for the- Yeah

like, like I said, that’s where the oil change, I thought, change oil and remember, you know, you’re putting, you could be putting in something that doesn’t have the right tolerances- Right … and additives. And who knows, you know, if it’s what led to, in Southern Argentina, I mean, I had to sell it for close to nothing.

Scott Brady: Yeah.

Cyrus: But got something out of it, and we had a rental car and jetted back north again. Yeah. And, you know, you start out in Africa next on something new.

Scott Brady: [00:19:00] Amazing. Well, let- let’s, uh, we’ll take a little pause on that story- Sure … ’cause we’re gonna, we’ll continue with Africa in a minute. But one of the things I think is that people would find interesting and, and can learn from is, you know, talk a little bit about how you set yourself up professionally because you did M&A work, uh, mergers and acquisitions, you were helping, uh, family offices with acquisitions, you were working in banking.

Uh, I mean, I’m, probably got some of that wrong. But let’s talk through a little bit about how did you set things up? Like, how did you first realize like, “Oh, that could work for me,” and then how did you set things up to be able to work for a couple years and then literally go travel the world for- Sure … a few more years?

How did you set that up?

Cyrus: At some level I’d say spreadsheets, gi- Yeah … as a geek, right? Y- you can make great projections on, many things. Numbers don’t lie, right? And I’d say though, uh, one of the bigger takeaways from being someone who studied economics is, uh, the key term marginal propensity to consume I always [00:20:00] looked at it like I’m not in this to break even.

How am I going to create time and freedom? Mm. And, I’ve experimented very broadly with it in terms of, uh, in recent years I was able to find a very interesting inaccessible piece of land that, uh, taxation is almost nothing. Mm. Those sorts of things sell for pennies on the dollar, and I just look at everything in terms of the arbitrage opportunity.

Mm. And getting positioned, though, I’d say for, for what my life ultimately has been able to become took keeping that low marginal propensity to sum- to consume, and to have the diligence to see through your opportunity cost of, is it buy this, uh, burger when, you know, I can very easily… And I mean, in, in recent years I got a little tired of it, but hey, roadkill deer even, right?

Yeah.

Scott Brady: Sure.

Cyrus: You learn, um, you learn what’s there that often is even better, right? It’s about [00:21:00] letting things find you-

Scott Brady: Mm …

Cyrus: as opposed to finding them yourself. And, and I find that in the chaos of the modern world with as much as we make things, um, really rapid fire, you don’t have the abil- like, most people are inefficiently entering spaces where they’re not allowing for the wu-wei, let’s just call it, right?

Yeah. Sure. Where, Those opportunities are sitting there in front of you, and every day you can almost reset your life if you allow yourself to take one brownie in motion move, one random move- … that leads to that day having that intersection, and I’d say intersectionality except for it almost becomes political using the term now.

Hmm. But, like, where are you gonna have that intersection that’s gonna lead to new things every day? And I’d say that really, yeah, it just comes down to having the diligence to be around your- y- look around yourself and say, “What do I care about, and how can I allocate every, um, m- ounce of resource into something that’s gonna bring me the greatest joy and [00:22:00] utility,” I suppose- Hmm

right, is the geeky economist element. And, yeah. Yeah,

Scott Brady: and I watched you do that. I mean, I you know, I remember, you know, y- to your point, you know, I’m not gonna spend money at this restaurant ’cause that could be two days of travel. Yeah. Legit. Um, I’m going to ride a motorcycle that I bought used, and I did minimal modifications.

Maybe I got some sponsorship because by not spending 80 grand on a four-wheel drive, I can travel for two years. And I, I watched you, you do that time and time again, where you’re, you were so… And m- maybe purity is a part of it, and I, and I think that it, that human beings can do that. They can stay, they can stay very pure to a value or to a goal if they just get over the ego a little bit, where it’s like, “I don’t have to have that fancy thing,” or, “I don’t have to spend that extra money on something that might signal something to the world, but it actually stands directly in the way of me achieving what I really want to experience in life.”

You know, you talked about th- [00:23:00] that intersection of values that you experienced when you were in Taiwan. Why don’t we dig into that a little bit? What are you finding after so many years of y- I wouldn’t call you an ascetic, but you’re definitely, you’re willing to be minimalist. You’re willing to dig into some roadkill deer in order to provide the protein that you need to save yourself a ton of money.

So w- talk a little bit about those intersections of values, how your experiences reinforce those values, and how you i- implement them in your life today.

Cyrus: Sure. The, the adventure that has come from, I think that in answering your question, I bring up that in the middle of many travels, I started having some very interesting phenomena in terms of autoimmunity that resulted in, you know, at times being fully on cripple crutches where joints don’t wanna move.

Hmm. Inflammation from the inside’s like a little nuclear bomb, right? That slowed me down [00:24:00] to a level that I could appreciate things even at the next level. Mm. That at times, I mean, I don’t know, I keep my cripple crutches pretty handy at times. Mm. Sometimes I’m great, sometimes I’m not.

Scott Brady: Mm.

Cyrus: And, um, I’d say that, uh, there has been an interesting walk into being someone who, you know…

I, I had an interesting upbringing in Jackson Hole, where my mother came from a good family but was orphaned, call it good family. And met my dad in her early 20s to buy one thing that was meaningful, which was a place to raise children.

Scott Brady: Mm.

Cyrus: In a beautiful place where they had a little farm, and I witnessed my mother’s health drop off.

And I was always very motivated to hustle and, you know, work hard. And I sort of witnessed my dad be that guy who did whatever he had to do. And I saw the trade-off. One of the harder things was being a 13, 14-year-old kid who’d been working for years for his black belt- … in taekwondo.

Scott Brady: Yeah.

Cyrus: The [00:25:00] night that the testing was coming through, it was 100 bucks for the testing. You know you’re gonna get it. Or 100 bucks is actually gonna lead to some cool things our family can use.

Scott Brady: Yeah,

Cyrus: sure. And I made that decision. And I think it’s, if you fast-forward into life, I’ve… At times where… I, I try never to have any regret.

You, you… The worst thing you can do is carry regret. But, um, I try to end up in a position that if I can look forward, what’s gonna give me the most utility, like I mentioned. So- Yeah, those trade-offs. Like, what do you value and what is your greatest dream?

Scott Brady: Hmm.

Cyrus: So if, in the case of two wheels, seven summits, that was a huge dream.

Scott Brady: Mm-hmm.

Cyrus: Or was it simply that I allowed myself, by the time that I’d been working hard for a while, to say, “A year or 20 grand, whatever comes first.” And I wasn’t that efficient at the time, but I mean, I was certainly so damn cheap that I remember being in Mendoza, Argentina, and I [00:26:00] wouldn’t use shaving cream, and I was shaving my face without cream and burning it.

Scott Brady: Yeah.

Cyrus: You know, because I’m, I, I’m just trying to cut every corner that I stinking can.

Scott Brady: Yeah.

Cyrus: And, and in retrospect, you know, like, what are you doing? But I’ve had a really fun process of having a chunk of land that I had to cut my way into that has gravity-feed springs. And that you’re having all of your adventures and your experiences, but you’re removing yourself from, let’s say even though there’s a big power line in some proximity, how about a minor solar system?

Hmm. And let’s see the way we can integrate an old ARB fridge with no battery- Hmm … a ton of old sleeping bags around it- Mm … and you’re gonna have it oscillate up and down slightly, but stay right on frozen all the time- Hmm … with no battery. Just tinkering.

Scott Brady: Yeah.

Cyrus: And you find that really it’s nearly an illusion that we need certain things.

And this is of course my take, but the story always is that we need Big Brother to do something for us. Hmm. And, um, I personally sort of see this world [00:27:00] where the more we have agency, which is a word that you added earlier that I love that, that really describes what I think is going to keep humanity on a plane that will have, uh, a better outcome in the long term.

And-

Scott Brady: And it seems like it’s done that for you. It seems like- Yes … the agency that you’ve employed in your life, the fact that you’re like, “All right, I’m gonna dig in.” I remember one of the times you and I were catching up, you were on a private jet.

Cyrus: Probably.

Scott Brady: What… You were. Yeah. You were on a private jet, and you were going off to do some big deal, and you were crushing it.

You were in full consultant mode, and you were working for someone on big, on a big deal, and then the next time I talked to you, you were heading off to someplace crazy in the world- Yeah … on a $4,000 motorcycle. To me, it was v- it’s been very evident that you’ve chosen to have agency over the experiences that you have in life and how they change you.

And, and that’s, to me- I found it very inspiring. I [00:28:00] absolutely found it inspiring to see that, like, y- th- to watch you operate at really are two extremes, but your heart was really only on one of them, which is experiences. But you were willing to be like, “All right, I’m gonna go– I’m gonna dig really deep into the professional space, uh, to make enough money to go screw off for two years.”

Not a week goes by that someone doesn’t reach out to ask how they can help support the podcast. Uh, we are, uh, supported entirely by Overland Journal, the magazine. So when you become a subscriber to the Overland Journal print magazine, you get this beautiful book, uh, that comes in five times a year. It also gives you access to our digital archive, and it’s well over 100 pages of, of gorgeous images and detailed testing and adventures from around the globe.

So if you go to overlandjournal.com and you subscribe to the magazine, use the code OVERLANDPODCAST, and that’ll get you 20% off. It’s only available to our podcast listeners. We don’t [00:29:00] advertise it anywhere else. And then you help us to maintain that independent employee-owned journalism that we have been famous for.

So it allows us to conduct those tests without any advertorial. Another way you can help out too, I produced a book, uh, last year with Simon & Schuster called Overlanding 101. You can find it on Amazon or Barnes & Noble or even your local bookstore. And that encompasses my decades of travel around the world, all of my mistakes and failures and, and the lessons that I’ve learned in traveling around the globe.

Um, many of those, um, that you hear on the podcast have been distilled down into print form with great lists and beautiful imagery. Uh, so you can find that, uh, at your local bookstore, Overlanding 101. And thank you all for listening and for supporting us so much throughout these years.

Cyrus: It’s, it’s been one of the greatest liberties yeah, to have that.

And at times, you know, you, you wish that you dove deeper. You know, we just had a wonderful experience with [00:30:00] friends for a, a couple nights. They had us over by Arizona or by, uh, Phoenix. And at times you, you want those creature comforts more- Mm … right? Mm. And it’s that sacrifice though that wakes you up, makes you appreciate what you do have around you in contrast.

Scott Brady: Yep.

Cyrus: I think contrast is such a beautiful element, and, um, I’m glad I’ve been able to do what I’ve been able to. And, you know, in whatever way, even the next generation chooses- Mm-hmm … chooses that or not we’ll see. They’ve got… We, we just are sitting where the paradigm is changing so rapidly as AI integrates its way into our face, our lives.

Dad, do you know I’m the

Scott Brady: next generation? Yeah, you are the ne- You are the next generation … you are the next generation, buddy. Yes,

Cyrus: you are.

Scott Brady: Which is a good thing. We, we need, we need that. We… I, I think about my nephews, and I’m like, “These kids are awesome.” Oh. Like, they’re way more awesome than I was. Yeah. They’re way more, kind of aware of life and thoughtful of others, and there’s like a…

There’s a depth to them may- maybe because they’ve been able to learn so rapidly because of the availability of information and, and probably the [00:31:00] diversity of the people that they exchange time with. Uh, but, like, kids are just awesome, like, way more cool than I ever was.

Cyrus: I’ll take it all day long. Yeah.

That, being around a kid… i, I keep reminding my dad, who will hear this-

Scott Brady: Yeah …

Cyrus: you know, uh, let the kids be loud.

Scott Brady: Yeah.

Cyrus: Let them knock around, have their fun. And, like, I, I think there’s, uh, some sort of quote that may have religious context that’s just the closer you can be to a child at the end of your life, the closer you will be to some sort of a heaven or bliss.

Scott Brady: Sure.

Cyrus: And I strive for that. Yeah. I think that’s a very important element.

Scott Brady: Well, and we talked earlier today an interesting confluence of both of our lives that we only just, uh, found out this morning when we were catching up. But, you know, your, your dad is struggling with some health concerns, and, and my dad is…

In fact, they both had sounds like strokes about the same time, about a year and a half ago. How do you, um, how do you process that change, the fact, the reality that, [00:32:00] you know, you have your son that’s coming into life, and we have our parents? You know, I lost my mom years ago, and how has that informed- Yeah.

Cyrus: My mom. So that, that’s a really bitter sweet piece- How has that

Scott Brady: informed some of your decisions?

Cyrus: One thing I’m very happy that I did. In 2015, I was doing a lot of Asia, six months of the year, whatever it was, Himalayas, Southeast Asia, islands, wherever. And, uh, I was notified that two friends passed in the year.

Mm. A man who was a very inspirational element and mentor in my life, who had been the CEO of Columbia Star Pictures and Fox in the ’70s. Hmm. A v- very… I worked at a restaurant he had in Jackson Hole when I was a teenager, and he opened amazing doors for me. And I, the respect I hold for that man is immense, just the perspective.

And a friend in a paraglider- … the same week. My only reaction was, “Call Dad. Dad- Yeah … I’m getting you a [00:33:00] ticket. I’m meeting you in North Vietnam.” The man had never left the country in his life.

Scott Brady: Yeah. Wow.

Cyrus: And, For him to show up on the plane and just be jazzed-

Scott Brady: Yeah …

Cyrus: ready to go, and he was still healthy enough.

It was that one moment- Yeah … that we had to get him on something big like that, for never knowing where life went, and of course, he shows up with a obsidian knives, and he’s like- … “Check out what I snuck through.” So proud of himself. But he went hard for about three, four days with me. We got great photos. We were out having, uh, you know, uh, s- uh-

Cyrus son: How old was

Cyrus: he?

He was 72 maybe, 70. Mm. Somewhere in there. He’s 82 now. And you know, having their local drinks and foods, and uh, he almost biffs it so hard. A silly move, but his athleticism is a, he- he’s kind of a pioneer of freestyle skiing, and he did this perfect move on the bike. I witnessed it. I was like, “No way would anyone else have been able to do that.”

Have pulled that off. And [00:34:00] not riding for 40 years, right? Yeah, sure. He just jumps on. And now to, to have the end of that and him tell me, “That was about my favorite experience I’ve ever had.”

Scott Brady: Yeah.

Cyrus: Even though I got to revisit with him after his stroke, I think he’s rewired some thoughts a little. Yeah. But he didn’t lose his memories.

Scott Brady: Mm.

Cyrus: Uh, and he didn’t lose his awareness. He’s just now slow and struggles to speak at times. And I’m just really happy- Yeah … uh, that we were able to do that, that that experience happened. And now in the midst of this energy that’s a child and his imagination and his lust for life, that reinvigorates in myself through his proximity and vice versa, I’m sure.

Scott Brady: Yeah.

Cyrus: Um, that is what life is about. Yeah. I look at it and I say, we have our relationships and our memories, and there are so many things that simply are not worth our energy to not partake in that have a darkness about them, and there are things that possess a light that is so bright and [00:35:00] lovely. I’d rather take that path than- Why

Scott Brady: do you think people keep taking the other path?

Why do you think people keep- Doing the things that they’re not, that they shouldn’t

Cyrus: I think the-

Scott Brady: Or they know, even they know they shouldn’t …

Cyrus: yeah. There’s a little bit around that hurt people hurt people- Yeah … that you just can’t help yourself because you’re caught in the thought that somehow them having fun will restrict your ability to enjoy.

And, uh, man, the more I can… I mean, I know being me, I’ve at times been a very bold element, and it doesn’t help me, and at times it does. But I would say that over time, most of the, most of those people that are choosing that path of like I go as far back to being a sixth grader and the kid that would go tattletale on all the fun you were having- Yeah

when there was a sub teacher, right? Like, why would were they doing that? And usually it, I think there’s something that is in themselves that they’re… Th- I think there’s probably jealousy at times- … uh, when you act in a way that you want to harm others. And I thought that’s what Psy was actually [00:36:00] bringing up there, was it’s something I said that I don’t know how it resonated with him, but it was it being people in the fast lane going slow.

And I said, “I don’t like being held up, and the last thing in this world I would ever wanna do is hold another person up- Yeah … from like achieving their ambitions- Yeah … and finding the joy and growth that is in their life.” Hmm. And one thing that I, I think I can say about those people who choose that is that I can almost thank them for creating a tangent which led to my own growth that maybe I never would have experienced in the path of life- Mm

that I’m in. ‘Cause we’re all on a different page here, and we all have different obstacles that we either create for ourselves, others create for us, or it’s something bigger than we could ever explain, but- Yeah, we learn a lot from each one of those things if we allow ourselves. I mean, recently I’ve been thinking a lot about that, you know, ’cause so much has changed in my life in the last couple years.

Scott Brady: And, you know, I was, I was, just thinking about the other day, you know, it’s like we gotta have, we gotta have some [00:37:00] purpose. We really do need to have something to chase a little bit. Yeah. We gotta have something that, that gets us up in the morning, gives a little, puts a little fire in the belly.

So I, I do realize, like, that I n- I know that I need that. I’m not saying that everybody needs that. But I know that I need that. I need that, that, I need to do hard things that gives me a lot of joy. Um, and then I, I think the one thing that I’ve really screwed up on in my life is I just haven’t had enough play.

From the outside it would… i’ve traveled so much, and I’ve done, I’ve had so many experiences, but they’ve always been, like, in the pursuit of the purpose.

Cyrus: The goal.

Scott Brady: The goal. Like, I’m very driven. But I, I did not stop and smell the roses much or at all in my life. You know, when I think about talking with others that are maybe starting off on the journey similar to what I started off on 20, 30 years ago, you know, there’s that, it’s such a cliche sh- cliche to say, you know, like, stop and smell the roses, but holy cow, there’s some truth to that.

Like, you know, finding, like you talked about earlier [00:38:00] about being at you know, at the top of, at Aconcagua and actually remembering that sunset that was happening. And that’s because you were intentional in that moment to stop and watch that unfold. So I don’t, I know that I haven’t had enough play and I haven’t had enough of those, that kind of joy in my life.

And then I absolutely agree with you about connection. It’s about the people that we know. And it’s so funny when you look back at that, like purpose and doing hard things and play and having fun and joy and connecting with others, none of that requires a lot of money. And that’s why you can see you know, someone in a village in Malawi, uh, that’s just got limitless joy.

They’re super happy ’cause they’re, you know, they’re challenged and they’re, they have purpose in their life and their family, and they’re connected with others and, you know, they’re having fun. They’re playing in the lake and throwing a, or playing soccer or whatever. It’s like, it’s really not that difficult, but boy, do we make it difficult sometimes.

Cyrus: Yeah, it’s 90% reaction. What, I was reminded of what you just said, the flowers, about two and a half months ago by a [00:39:00] very lovely woman in my life who I love so much, and she’s, she actually was the one ironically in thinking this, that she said, “Are you ever stopping to smell the flowers?” And, uh, that, um, end goal thing is actually a large component if I’ll ever get online for you a couple of those episodes.

It’s the, the why did you come to Japan-

Scott Brady: Yeah … the

Cyrus: Japanese show. One of their more bigger things that’s a theme, it’s a very well thought out show, has to do with why did you say, for example, I was pe- peddling a bicycle through Japan, that I picked up hitchhiking. I called it a mom bike. This thing had three gears, a basket on the front.

I had The Economist in the front and a, a big jacket sleeping bag. The jacket I got at some used store. Bicycle was given to me by a Peruvian Japanese guy, which was great, right? He’s this species- Amazing … and, uh, and they’re like, “What, you didn’t achieve your goal,” was the whole thing, ’cause I was just going home.

I was tired of… At the [00:40:00] time it was the rain. Sure. I couldn’t communicate, and- Right … I just kind of wanted to go home. Yeah. And they’re at the airport, and they’re like, “Why are you doing this?” And it was that same like, because I want to enjoy the journey. Yeah. And right now it may not be the… Like, I guess you gotta know, it’s almost, it’s similar to climbing a mountain.

At what point do you actually stop and see what the crystal ball says, and is it worth continuing? And it depends upon what your goals are. Yeah. At that juncture, my goal was, uh, I kinda wanna go back home to Jackson Hole, see some friends. Yep. Jump in a hot spring, even though there’s hot springs there.

Scott Brady: Yeah. And- Yeah, you wanted to change, change the scenery. Yeah. Yeah, absolutely. Exactly. So y- Yeah, no, that’s such an important one. Well, um, let’s talk a little bit about travel ethos and kinda how you prep for trips. You’ve done a lot– Most of your trips have been on lightweight motorcycles. Why do you choose lightweight motorcycles, and kinda how do you tend to set them up?

Cyrus: Yes. [00:41:00] So I’m a horsepower junkie. I like power to weight. KTM, Husaberg, Husqvarna just, they, nothing really competes, you know? Yeah, they

Scott Brady: dominate.

Cyrus: They dominate and I got on that train at a point in time. And there’s this motor that, uh, you know, the article I wrote for you guys. Later, you know, people see pretty clearly.

Thousand hours, don’t even check the valves. So going with something first that I look for what makes a sexy bike- First power and maybe equally longevity. But, you know, KLR, is that that sexy? I don’t think so. Yeah. So you need the balance. Yeah. It’s that, that hybrid component of both. And, um, I like something that I feel I could, uh, slide under a barbed wire fence.

I could probably push it through a river after I throw a plastic bag around the intake-

Scott Brady: Mm-hmm …

Cyrus: and, and have some help somewhere pushing it, you know, even nearby here, the Verde River- Yeah … multiple times, right, where you’re gonna have to turn back 100 miles, [00:42:00] or you could continue and hit some insane desert from here.

Something that feels agile, like it’s a rape ape under you and it is- Yeah … tearing. That is something to me that it keeps your lymph flowing.

Scott Brady: Yeah.

Cyrus: So yeah, I’d say that, uh, that kind of bike is huge in my world

Scott Brady: to have. Well, maybe we’ll just wrap it up with like- Yeah … w- how do you normally pack your gear- Yes

on the bike?

Cyrus: Okay. These days, I’m still using bags that, um, Pete always was offering me bags with his Mosko Moto’s, and I think- Great, great

Scott Brady: bags. Yeah … he’s done

Cyrus: the best thing. And s- talk about 950s, before he conce- when- as he was conceiving the ideas for the company, I met him at a gas station randomly in Mexico, and we camped for a night.

Awesome. He started telling me all about what he was gonna do.

Scott Brady: Yeah.

Cyrus: I’m like, “This guy seems like he’s on it.” I’d

Scott Brady: say- And he has been, man. He’s have a good, had a good run. I just got a bunch of his, uh… I’m gonna go test the new Aprilia Rally.

Cyrus: Okay.

Scott Brady: The Tuareg Rally- Yes … in Utah in, uh, next week. Awesome. Um, so he sent me all of his [00:43:00] Mosko- Great

his new adventure motorcycle- So exciting. Yeah … gear. So I’m, I’ve got one of his little Pico tank bags, and I got all of his jacket and pants and stuff like that. Sure. Man, it, it’s really great to see you. You too, Scott. I’m gl- I’m glad to see that you’re doing well, and we gotta stay in touch more than, texting each other every three years or so.

Yeah. I agree. We’re, we’re, we’re always in some random cool spot in the world, usually at the same time. Yeah. Um, you know, different parts of the world, but we’re always doing something fun together, and I’ve always wanted to have you on the podcast. And when you reached out that you were coming through Prescott, I’m like, “I gotta make that work,” ’cause I’m- Yeah

I’m around for one day. Yeah. And we were able to pull it off. So man, thank you so much for being on the podcast. Thanks

Cyrus: for having me, Scott. All

Scott Brady: right,

Cyrus: buddy. This has really been fun.

Scott Brady: Yeah, we’ll do it again. We thank you all for listening. We’ll talk to you next time. Wahoo! Awesome.

Cyrus: That’s great.

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