The Most Interesting People in San Diego

The Most Interesting People in San Diego

I spent six weeks in San Diego in late 2016. As I mentioned in a previous post, I met few new people and most of my social interactions were with people I already knew. One was an old friend of a friend. Another was a guy I only knew from the internet before. Turns out, him and his wife are the most interesting people in San Diego. It’s kind of funny. I only really met about 10 people around San Diego. And most of them are really interesting. Yeah, It’s absurd to declare I know the most interesting people in San Diego when I only know 10 of them. But hey, some “how to blog” thing I read said to make compelling titles. And I may still be right anyways. I’ll tell you about a good deal of those 10 people here.

The Most Interesting People in San Diego

Craig – the Video Guy

Craig is an old friend of some of my other close friends. We never lived in the same city but we saw each other once or twice a year for many years. He’s a videographer and has had a number of interesting jobs in the field. He also made this short film called A Server Life a few years ago which you particularly enjoy if you’ve worked in the service industry. Or if you prefer the more real/natural world, here’s this video he recorded of when a huge whale carcass washed up on the coast near where he lives.

His current day job is recording what I understand to be court depositions. He gets to listen in on witness accounts of what happened in a variety of cases. A pervious job was a private eye. Yeah, a private detective. Like the guys who tail somebody recording their whereabouts and filming them. He had some really funny stories from that. One was about a mentally unstable and violent guy he was supposed to follow. He asked the company he got worked for some questions to get a better idea what he was getting into  (like, “hey, is this guy going to try to kill me if he notices me?”) and if I can remember right, they just said “ahhh, I don’t know..  just go ahead and do it, you’ll probably be fine”

Because of the subject’s mental instability, he was already super paranoid about being followed and monitored (even before Craig started monitoring him). He’d do crazy stuff like leave his house at 5am to go to a 10am doctor’s appointment that’s only a 15 minute drive away. So of course, since he was so paranoid about it, the guy eventually noticed Craig monitoring him. Craig survived though.

When I got to town, Craig said “Let’s meet and [have a drink], I want to talk business”. That “business” was making a video about me living in the van. So we spent a few days working on that, shooting various clips of driving the van, doing stuff inside it, and some interview parts with me talking. I felt like I was being way too boring, so I hope he’ll be able to make me and the video look cool with editing magic.

San Diego
We shot a bit of video here

Funny moments with Craig – free stuff just appearing!

On our first day out shooting, we went to a little area of dirt overlooking a beach and sort of a swamp.  While Craig was setting up his camera and the shots, I walked around to move trash that was probably in the shots. One of those trash Items happened to be a 6 pack of tall beer cans, with four unopened cans remaining.  The cans were undamaged so I took the 6-pack over to Craig to see if he wanted it. He did, and said that it’s a fancy beer. $15 for a 6 pack.

The third location we went to was near a Library. We found a parking spot in the Library and started walking over. As we walked past the front entrance, there was a rack of books and magazines with a “free” sign on it. One book stood out to me right away. It was about serial killers. We had just been discussing them last night because Craig’s girlfriend has a sort of fascination with them. So I grabbed that book to give to her. We took another book, and about 10 magazines that my Craig likes. Score!

The Most Interesting People in San Diego
One of the Encinitas beaches. We shot a some video here

Funny Moments with Craig – Trash Endemic of the Rich

Ok, this one’s not exactly funny. One evening we did some shooting near the beach pictures above. While driving back towards my Craig’s house, we went down a road with beachfront houses. Craig noticed some trash cans out on the street and said “oh yeah, this street is a dumpster diving goldmine”. He listed a number of nice things he’s found here left out for trash by their owners. Furniture, electronics, etc. After passing 10 or so houses, a trend was apparent. These people throw a lot away. Every house had multiple cans out. Some had SIX or SEVEN! I thought maybe this trash pickup is infrequent.  Surely, with this much trash, it must only be collected once a month. Or every other week? I asked Craig. He said it’s picked up twice per week. TWICE PER WEEK!

By my quick calculations, these households are throwing away somewhere between one and four THOUSAND pounds per month.

Craig’s cousin – Angela – The Hiker

Craig’s cousin is cool. He made about her hiking Mt. Kilimanjaro. We went on a couple hikes with her.

We went on a short hike to “Mushroom Caves” one day:

The Most Interesting People in San Diego

We snaked through some really narrow paths. Extra narrow, at one point, because we took a wrong turn. The picture below is shot from inside the “Mushroom Cave”. I don’t know whether the entire cave was carved out, or if some/most of it was natural. Now there’s all kinds of stuff people have carved into it. The carvings are pretty ugly, but someone did at least carve out some nice seats in there.

The Most Interesting People in San Diego


Jared – The Podcast Guy

I was out with Craig one night. We met some of his friends at a bar to hang out and watch UFC fights. While there, Craig told a guy  (Jared) about me being retired, living in the van, and traveling. Earlier, I’d overheard Jared telling another guy about a project he was working on. Some stuff about how people don’t go after their dreams because they let their fear of failure get in the way. Jared talked to me a bit and asked me if I’d be on his podcast. Sure, what the hell. I’m keeping this brief because I’ll likely make a full blog post about it. Hint: there’s already a link the podcast near the bottom of my front page. 


Rich and Amanda – The Most Interesting People in San Diego

I knew Rich from a forum on the Internet. This was the first time we met in person. Rich and his Wife Amanda met me for tea/coffee in Balboa Park – in the same area pictured below. They brought a thermos with hot water, cups, etc. We had some great discussion. I showed them the van. Rich showed me the building they manage, which has a secret lair. Seriously.

The Most Interesting People in San Diego
(I started building this website while in San Diego)

Rich and his wife have designed an interesting life. Starting 20 or so years ago, they saved up some money, quit their jobs and went on a HUGE adventure. Then they came back to San Diego, got new jobs, and saved up again. Then, another HUGE adventure. And again. They take partial retirements every few years. And they’re also building up for a full retirement later.

Their travels and adventures are extensive. Their first trip, essentially their honeymoon, was taking a VW Bus (a camper), south into Mexico. And further south through Central America. And all the way to the southern tip of South America. Then back up through Brazil. Then they shipped the Bus over to Africa or Europe and continued! They wrote a book about this big first trip. If you like this kind of travel, or big adventures shared by daring, optimistic, and funny people, read it. I promise you’ll like it.

That was just their first trip. They also went bicycle touring through Southeast Asia, rode a motorcycle through India, went to Mt. Everest, and more! Their lives are so  inspiring that an insurance company made a commercial about them:

(After their commercial, another commercial with a different guy starts at1:50. I was confused by that the first time I watched it)

It felt like a privilege talking to a guy who has spent much of his life doing awesome things and learning about life and people instead of learning about TPS reports. He has friends who are super rich, and friends from Tijuana who are probably quite poor.  He is really really good at identifying interesting people, and at getting them (and normal people) to tell him their interesting stories. He asks them another question as soon as they finish answering the last, and doesn’t leave pauses where the conversation can lull or stop. And is very interested in the person / their story. 

Amanda grew up in Mexico. She came across the border every day to go to College in San Diego. Crossing the boarder into the U.S. is crazy. There’s a ton of traffic and it can take hours to get through. She waited in that line every day to go to school. You have to really want something to be willing to do that.

Their book tells about a discussion they had one evening. (forgive my poor telling of this from memory, It’s told much better in the book).  They were both having a “there’s got to be more to life than this” realization. They sort of decided to do something adventurous but didn’t have any clear decisions made. The next day Amanda came home from work with a stack of papers. She started rattling off things. Ok, we’re gonna need [this] and we’re gonna need [that], and it will probably take about [this many] weeks to get [such and such]. Rich was like “huh? whoah. what? What’s all this?”. And she says. “Mexico. We need to go to Mexico! On an adventure. I started planning today.”

Pretty soon they’d saved up money, quit their jobs, outfitted a Volkswagen with clothes food, and a bunch of random spare parts. They crossed the border to kick off a honeymoon that lasted years.


I went along with Rich to a swap meet. I bought three pairs of really nice wool socks for $2.00,  and some hiking pants for a few dollars. Rich bought about 16 things. One of his hobbies is buying outdoor gear cheaply at places like this (places where the goods are just one short step away from a landfill) and selling them to people who will make good use of them. The flow of goods is interesting:

  • People donate to Goodwill, and companies offload excess products.
  • Goodwill takes excess stuff to sell in lots in Mexico
  • Those Mexicans come back across the border to sell that stuff at the swap meets
  • Rich buys the good outdoor gear from them
  • He knows many of them. They set aside stuff for him because he pays a little extra
  • Rich re-sells the stuff, mostly on Ebay, to people who are likely to make good use of it.

(There are other material sources than Goodwill. Like garage sales where at the end the seller just wants everything gone. And companies that get rid of excess inventory (new/unused items))

We went for three bike rides together. The first one, we rode to and took the ferry to Coronado Island. Coronado is a small island just barely off the coast. About half the island is used by the military. The other half is nice houses and fancy places. We worked out at a park that had the appropriate structures. The second bike ride we went on was in Balboa park on some mountain bike single track. It’s good riding in there. I crashed! And got a flat. And another flat later. oh, man! Our third ride was over to Mission Bay Park. There was a steep, long hill on the way back. Rich lead up the hill and went fast. I could just barely keep up. At a couple points, I didn’t think I’d be able to hang on with him. But I did, and as we got to the crest of the hill, I rode up alongside him and said “That’s a nice hill. Good warm up. Can we go back down and come up again, and go fast this time?” 😀

The Most Interesting People in San Diego



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