Introduction

Here is the short story of my 150-kilometer trek from Portugal to Santiago de Compostela, Spain. Over 200,000 people hike each year on this pilgrimage. In the olden days when people were still stoned, this used to be a Christian pilgrimage to visit the grisly bones of Saint James. Nowadays many people make the hike and it’s no longer purely religious, although many people are still stoned.

Either way, it’s certainly a spiritual journey.

Wanna see the other Walk n’ Talks? Here they are!

1) Hugh Howey on World Building
2) Aaron Lammer on Crypto
3) Matt Mullenweg on WordPress and more

In terms of religious hikes, it doesn’t really compare in numbers to that of Mecca, where 15 million people walk each year. That walk mostly originates from Jeddah and clocks in at around 70 km. Either way, this epic Santiago hike I did has multiple routes. The full route is over 1200 km from France or a lighter version from Portugal at around 200 km. Mine was just 150 because we started right at the border in Tui, Spain. It’s also shorter because we are all kinda lazy and get the point after 150km.

I’ve decided to tell a multi-part story via conversations I had with my nine other walkers. This event was put together by Kevin Kelly and Craig Mod who have completed a few of these sorts of walks around the world. The idea is a bit of a “Walk n’ Talk” where we mostly philosophize about the world, make jokes, and engage in a stimulating amount of mutual mental masturbation. Everyone on this adventure was from different walks of life. We had everything from tech magnates to authors to photographers to entrepreneurs to DNA researchers, and well, you name it.

It was great, for me personally, to establish deep connections with each and every member of our hiking tribe. At least, I think I did! 🙂

Below is one of many 360 videos (link to subscribe to my YouTube channel) I made while on this hike. I’ll post them a bit out of order. I talked to Kevin about several disparate topics in different videos including AI, an enormous underground clock he is working on that lasts 10,000 years, a series of bottom-up libraries that are being built in a Nevada desert, Burning Man, and last, something that sounds a bit macabre: Death.

By the way, I know a lot of geeks like me watch this, and you may want to know what equipment I use. Here are the kit links for my Insta 360 camera and the Zoom h1n recorder use for audio – also follow this link to see all my gear.

The overall idea was that we spend most of the day discussing philosophy, science, and other erudite matters. Each night at dinner we had a different discussion. World governance, urbanization, religion, and relationships just to name a few. We would record about three hours of these blatherings and they’re putting together all the transcripts now.

Anyway, that was the texture of the seven-day hike. I’ll get started with an overall paintbrush stroke of the trip then get into Story #1 with Kevin Kelly. In the next one, I’ll talk about my discussions with Hugh Howey, whom you may recognize as the author of Wool and the Silo series of books. I’m starting with those two because I knew a lot about them either in person or via their work before the trip. After, that, I’ll share stories from some of the other ne’er-do-wells that joined us.

We started on the edge of Portugal, and you’ll see a bridge below that links northern Portugal and Spain.

This mini-bridge walk was technically before the whole hike even started after our motley crew assembled for an introductory dinner.

After dinner, I walked across this bridge around midnight with Matt Mullenweg, the founder of WordPress and current CEO of Automattic. In a short time, we talked about a bit of everything from him changing my life by founding WordPress (my blog at www.StuckInCustoms.com) to doing recreational drugs at Burning Man. But I’ll save more of that for the Matt Mullenweg story day!

It was sort of unusual being thrown into a group of ten people who you don’t really know. I remember one of our fellow walkers, Chris Barclay said on the final night that he felt a bit intimidated in the beginning. You know, trying to figure out who the cool kids were and trying not to make a fool of one’s self. That’s a universal feeling everyone has when entering a new group. As we paired off in organic one-on-one situations, as I did on this first night with Matt, everyone could see there was nothing to worry about and this was a very cool, non-judgmental group. In a very short time, all that self-doubt disappeared like fog in the morning.

Above you see one of our typical mornings. We would often pair-up, but not always, and talk about a wide myriad of subjects. It made the countless hours of walking go by extremely quickly. I was so busy listening to other people that I barely even realized that 20km had already flown by.

Not to skip ahead to the END of the story, but the photo above is where the journey ended 150km later, in Santiago de Compostela. The town itself was beautiful and the energy was palpable. I think, because so many people reach here every year in such a euphoric state, that it suffuses the town with positivity.

I’ll talk more about little things along the adventure here and there as I talk about each individual person… but, first, let’s start with the guy that invited me, and one of my only intellectual heroes: Kevin Kelly!

Part One: Walking & Talking with Kevin Kelly

I only have a handful of heroes, and not many are alive! You all may have already read my story about another living hero, Hans Zimmer, but now this is my story of Kevin Kelly.

Kevin is best described (if possible) as a philosopher that ties together technology, history, and futurism into a central theme of optimism.

When I saw his first TED talk (now he has about four), it had a tremendous impact on how I approached life, the blog, my work, photography, and more. Even though Kevin himself is an accomplished photographer with countless crazy stories about traveling all around the east, most of the information he synthesizes is from a plethora of other subjects.

What exactly did Kevin affect during my “formative blog years”? Even though he didn’t specifically speak to this, it confirmed my instincts to make almost everything free. I would upload full-rez photos every day to the blog. I would not use watermarks. I used Creative Commons Noncommercial as a means to drive traffic back to the site. I gave 110% to the very few early fans that seemed to enjoy the work. Kevin has a great essay called 1,000 true fans that really resonated with me very early in my arc.

I went on to read his books and watch more tech talks. He has a wonderful take on “What Technology Wants” and he sort of frames it in the way that tech, itself, grows in a not dissimilar path to other genus/species. Here is one of his TED talks about what technology wants.

I first met Kevin about seven years ago when Thomas Hawk and I did that mammoth ~500 person photo walk in San Francisco. Kevin came up to introduce himself to me. I was like, “WHHAAAAAT! Kevin you don’t need to introduce yourself! I’m a mega fan!” And I was. I was just about as close as one can get to being a stalker without crossing the creepy line.

Since that time, we’ve been together on many occasions. We met in San Francisco and he even invited me over to his home in Pacifica, a Valhalla of sorts for me. That is when I first met his wife Gia-Miin, who also joined us on this walk.

Last year he invited me to go eagle hunting in Mongolia with Tim Ferriss. I wanted to go, but it was right after Burning Man, and my wife would have killed me for being gone so long. So this year, when he invited me on the Santiago hike, I agreed! I had no idea what I was getting into, but I generally say yes to adventures then figure everything out later.

The whole week was such a treat for me and I was honored to hang out with Kevin. I felt like a little kid around him, asking 1,000 questions. I was trying not to be annoying… well, at least that was my goal. By the way, I am not really an “interviewer” or anything. I’m just a curious guy.

I came up with this plan to ask Kevin a different question every day and record it. I wrote down six questions beforehand, but I changed most of them as the week went on. For example, I never thought about talking to him about death until I was having a one-on-one with Hugh Howey and we came up with an idea on how to divvy up Kelly upon his exit from the mortal coil. It was of course influenced by this stimulating walk he encouraged all of us to undertake. All that talk began as a side-conversation after Hugh told me he planned on killing himself at 40. That’s another video I’ll post. I mean, the video of the discussion, not the actual suicide.

After I got to know the other walkers, I decided to take this idea to many of them too. So now I have many of these 360 videos with most of the walkers. Time and data didn’t allow me to record all 100+ hours of our time together, so I kind of picked randomly. Once again, Kevin inspires me intentionally or unintentionally to try new things and just be authentic in your awkwardness. I mean that in the nicest way, of course. I can tell that Kevin is an introvert, like so many of us. This comes across in his speaking style, a style that is uniquely his own. He’s so authentic and real that he both believable and endearing. I am sure this comes with something else he encompasses, being comfortable in his own skin. So many people aren’t, and he also got me started on that path about ten years ago.

One thing we share in common is that we have spent a tremendous amount of time in the east (China, SE Asia, Japan etc) with local cultures and taking photos. It’s made us both very attentive and present, I believe. When you’re talking to him and vice-versa, it’s like you’re the only two people in the world. I’m lucky I didn’t fall into a river or fall off a cliff while we were talking because it was so engrossing. He’s adopted somewhat of an eastern philosophy that seems to inform all of his thoughts and actions.

It’s impossible to summarize our 20+ hours of one-on-one conversations. Impossible. But you’ll see a few highlights as we release videos.

I think his books and TED talks have influenced me so much that sometimes I don’t know where he begins and my brain ends. We were making obscure references to books, authors, tech, etc… at some point, I mentioned one of my favorite quotes. I asked him if it was Feynman that said it, and Kevin said, “Wait a minute, I said that!” I was laughing so much and apologized… I’m getting old.

See more of Kevin’s quotes here

Along the way, after we stopped in a town for the afternoon, Kevin and I went off on our own little adventure to record an episode of his “Cool Tools” podcast. He interviewed me then we walked around the park a bit after the recording. He turned to me and said something nice. “Trey, you surprise me!” I didn’t know what to say.

One thing that I’ve noticed about Kevin that is not initially expected is how silly he is. He laughs a lot and says funny things. He is also very quick to laugh at jokes the rest of us make. It’s a wonderful thing because so many intellectuals can be so boring and self-serious.

My degree was in Computer Science and Math, so I’ve always been interested in tech and the future. This is a very strange time with the acceleration of everything from AI to Robots. I try to figure out where it’s going, but I get a lot of guidance (and optimism) from Kevin’s bullish outlook on these matters. See more about what he thinks about the future of AI in his TED Talk on AI or his latest book The Inevitable.

Of course, another typical question that comes up among geeks is: “Are we living in a simulation?” This question has been officially banned from Elon Musk’s hot tub conversations (for real) because Musk sees it as a “circular argument”. Kevin is a bit more practical with it, indicating it doesn’t really matter. He says the important thing is that we have a tangible effect on everything and everyone around us. That’s a pretty cool stance and helps get the mind out of that circular argument.

Kevin’s super-IQ wife joined us on the walk too, Gia-Miin. She was the only female on the walk, so she was able to keep things fairly classy. You don’t want 10 guys together for a long period of time or else it can spiral down to nonstop tales of ribaldry. Anyway, Gia-Miin works at 23 and Me as a genetics researcher in the cancer area. She told me all about it one afternoon. I could immediately tell I was out of my depth when we started comparing the progress of genetic therapy and whether that would outpace tech innovation when it actually comes to helping humans get better. But they’re doing all sorts of amazing things over there, and it looks like they are going to figure out a lot of the “bad code” that makes humans have bugs.

Kevin and Gia-Miin have a really interesting origin story to their relationship. I won’t tell the long version, but it really seems to work and they are best friends. How wonderful! I know their daughter Ting from a few times when we have been at the E.G. Conference together. I need to send her a note that says, “Hey, Ting, you know… your parents are kinda weird.” I can’t wait to see her response. But, of course, I mean weird in the best possible way.

I’ll end the story of Kevin on the final night’s dinner after we all finally arrived in Santiago de Compostela. We again had a round-table discussion. At the end of dinner, everyone was a little bit teary. Kevin turned his chair to me as we were all getting up to leave. He put his hand on my knee and said, again, smiling “Trey, you know, you really surprise me.” Even getting more teary-eyed, I playfully pushed at his shoulder. “Hey man, that’s what friends do. They surprise each other.”