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Ep. 236: How this amateur traveler turned into an award winning globetrotter with Chris Christensen

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In this episode, I speak with Chris who is the host of the Amateur Traveler which is an award-winning online travel show that focuses primarily on travel destinations. 

He has worked for years in technology startups in Silicon Valley and was formerly the Director of Engineering for TripAdvisor and ran online communities and events for companies including eBay, HBO, TV Guide, Expedia, Marriott, A&E, and so much more. 

Listen on to find out how Chris balances silicon valley and traveling.

Listen Below:

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Transcription:

Debbie:

Hey everyone. Thank you so much for being here. I am really excited to speak with my guest today. I’m here with Chris. 

Hey, Chris, how are you? 

Chris:

I’m good. Thanks

Debbie:

Thank you so much for joining us. Can you tell us about you and why you live an offbeat life? 

Chris:

Well, that’s an interesting question. We were just debating whether I live an offbeat life with me less sure than you are. 

So, I am a little older than your average listener, I think. I have a couple of millennial kids, just to put me in the right generation here. I’ve worked in tech for a long time since Reagan was President. And I work my way up the corporate ladder, and I work my way down and off the corporate ladder. And then come back at various times. 

So I worked in high-tech, worked in Silicon Valley. I’ve worked about 18 years for venture-backed startups and worked for big companies and things like that. Worked my way up to be VP of engineering and then, like, worked my way to be Director of engineering for TripAdvisor and then left.

And have been working my way down the corporate ladder ever since then so I could find more time for travel including about 6 years as a part-time programmer, a bit part-time contractor working about a third of the time. 

And then I also have a travel blog and podcast which is one of the reasons I had some opportunities to travel that I wanted to be able to say yes to which has led to some of my career choices. And I’ve had that for 16 years now. 

Debbie:

I’m just laughing because it’s funny when Chris says that he doesn’t know if he lives an offbeat life and he just mentioned to us some of the things that he’s done. And I’m pretty sure you haven’t even dug deep into really everything that you’ve done yet. And I’m like, “Oh my gosh, Chris, this is incredible.” 

And I also love the fact that you say, you worked your way down the corporate ladder. Can you explain that a little bit more to us and what that actually means?

Chris:

Sure.

So, for instance, I’m working again full time right now here for the last couple of years at a bootstrap startup company but I’m working as an individual contributor. And my boss is somebody who reported to me for 13 years. I was his boss as the EVP of engineering and operations for a startup company, here in the valley. 

Had that work with a lot of major brands doing community-based products. I followed him to TripAdvisor. We’re both directors of engineering over there. I took over a group that he used to manage, which was flights. And why he brought me in is we’ve had a similar managerial style. 

I worked there for a while and then decided I wanted to work on a product that I had created, which was called Blogger Bridge, which was to help connect bloggers and other companies. And I wanted to have more time to do that so I left that company and went to work at a small startup company for about 18 months as a direct contributor. 

So I left management and went back to work as an engineer mainly to learn some skills so I could do my own startup. I learned new technology, for instance, I got paid by somebody else to learn that. 

And so I was working at 1 startup during the day and I was working on my own startup at night and then, of course, podcasting all the while at the same time. So I was working about three jobs at that point, left that, and then went into contracting. 

I basically started doing software contracts. Many of them for the same person I’m working for now. I spent three years working as a contractor back at TripAdvisor, including in the same group that I used to manage as a day-to-day contributor part-time. 

And they force you as a contractor. To prove you’re a contractor, you have to take time off. You have to take off, I think, for 4 to 6 weeks a year in a row. 

Debbie:

Oh, wow.

Chris:

You have to have a block that you leave, which is perfect for me. As somebody who was getting offered trips, I could take that when I wanted. So I would often take that around TBEX, the Travel blog exchange conference, which is one of the largest travel blogging conferences, would be in Manila or something like that. Or I would have some press trip to wherever.

And I would kind of back those up back-to-back and take that block as a traveling block but then also take other times off during the year where I wasn’t working even halftime. But as a software contractor, you can make a living that way. 

And I was making less money than I was a Director of Engineering but I’m traveling more and I was happy. 

Debbie:

Well, you definitely did the opposite of what most people tell you to do, right? They tell you to work up the ladder, not work your way up. 

Chris:

I did that first.

Debbie:

Worked your way up and then go back down again. But you have a really interesting mentality throughout all of this because you were learning, you did this to learn, to do something that you wanted for yourself. 

So when you worked your way up and then went back down again, what was that like? Was it something that you knew you needed to do? Was there kind of preparation for that? What did your family think about it? Did they think you were crazy? 

Chris:

Well, my kids don’t worry about me anymore and my wife doesn’t really worry. 

So I went to my first startup company when my wife was eight months pregnant with our second child.

Debbie:

Oh, wow.

Chris:

The theory being, “Hey, why don’t go sleep anyway?” But I left HP, which was the company I was at at the time and the main reason I went at that time was that my boss had gone to a start with somebody who had three successful startups.

And the person who was the head of engineering had been behind the Atari ST and the Commodore 64, which if you look up your history books, were fairly significant figures – for those of you who weren’t around at the time.

And so it was an opportunity that wasn’t going to happen that often. And so I left there and it was a spectacularly unsuccessful startup. We burned through about forty million dollars in about 3 years and I was laid off, I was unemployed. And the people who were laid off the day I was were the happy people.

The ones who were staying were the ones who were going to be arguing about where the deckchairs should go on the Titanic. I mean, the company was done the day that I was walking out the door – not just because it was me.

And I’ve interviewed for two weeks and had seven job offers. So where I work in a field that is Silicon Valley, we are not risk-averse as a rule in the valley. And I was working with somebody at that company, for instance, he had been at 12 startups by the time we started day one, I think, and 11 of those had gone out of business.

And so once you learn that you can get a job again, then it allows you to take more risks. And that’s one of the reasons I’ve gone to a couple of other startups, 4 startups full-time since then plus contracting and some other startups. 

So they weren’t particularly worried about it, I would say.

Debbie:

Well, being that risk-averse, it really prepares you for so many different things because you don’t know whether that company is going to succeed or not. And you talked about all that money in just a few years – that’s crazy to me. That’s mind-boggling for most people but it’s really you living so many different lives in a span of a decade or a little bit over a decade. 

And you have all of these experiences. That’s why you’re so employable, right? Or you can create your own business because of all of these things that you got from that and then you added on podcasting and blogging. And I would say that you’re definitely an OG in both of those platforms. 

So, tell us about that, Chris, when did you start? Like, 16 some-odd years ago when nobody even heard of it?

Chris:

I started blogging actually in 2004 and podcasting in 2005. For those of you who don’t remember podcasting in 2005, I actually started podcasting a little bit before Apple added podcasts to iTunes.

Still very unknown at the time and it had started a little less than a year before I got started. So the funny thing is, and listeners will laugh at this, I thought I was late to the party. I think about that every time and say, “Well, is it too late to start a podcast?” Like, I thought I was late then and you are and I was but you have different advantages and disadvantages typically when you start.

When I started it was harder to get people to listen because there just weren’t that many people listening to podcasts. It was very unknown at the time. You spent a lot of years, not just months, basically explaining what a podcast was. And also the technology was just not there yet. 

When I originally hosted my podcast, I was doing it on a computer in my backroom. An old Mac that I had sitting around that I turned into a server. And the first time that iTunes promoted amateur travelers, that thing did all but catch fire. Basically could not keep up with that demand and it went down.

I’m sure there were only hundreds of downloads for that particular episode which is less than I get now. Now, I get a couple of million downloads a year, somewhere in that range. 

So, it has changed a lot since then. But, I got into podcasting ’cause I started listening to podcasts ’cause the first podcasts were tech podcasts. I was watching a tech TV show Call for Help. It was out of the Bay Area then it moved to Canada and they got shut down and turned into a podcast. The podcast is called This Week in Tech. 

And I started listening to them and I liked the format. It’s certainly better than talk radio or something like that. It was another audio format. And for me, it is better than music. And so then I started listening to other podcasts that were out there and thought, “I gotta do my own podcast.”

I didn’t know what to do at first. I thought about doing a tech podcast but it probably would have been a Mac podcast because I was a Mac guy. The first computer that I owned was an Apple II and the second one was a Mac plus. And I worked for Apple for four years after my first startup and before my second startup.

And then I thought about that but there was already an Apple show out. There was already a Mac show out there and why would you need to? Now, of course, there’s far more than two. 

I thought about doing a religious show which actually did start, The Bible Study podcast about a year later than that but we had some friends over for a Memorial Day picnic and all the best stories were travel stories so I thought, “I’m going to do a story about my travels,” which was a really stupid idea as it turned out because I was still working full-time. 

That was actually when I was at Live World which was the community company that I mentioned. I was an EVP of engineering and operations, traveling four weeks a year and podcasting 48 weeks a year, and that math does not work. 

So it very quickly turned into an interview show and I’ve found out I really love talking to people about their travels, love to talk about places I’ve never been to, some of which I have gotten 2 cents on starting to show. 

I’ve done a lot of traveling because of the show, so that has been a real added bonus from there. Got invited to the Obama White House because I was a travel podcaster, got to be a paparazzi for a day for the pope in the Kingdom of Jordan because I was a podcaster. 

So it led to some interesting and surprising things. They use amateur travelers to teach English as a second language at Oxford University and a test for English proficiency, one should say that carefully, for the Thailand foreign ministry. 

So it’s been an interesting ride. 

Debbie:

Well, this is something that most people don’t think about when they think of podcasting. And it’s so interesting too how you thought you were late to the game and now over a decade later and all of these things have happened to you because of the work that you did on this platform. 

Did you ever think you would get to this point where you would be, like, with the President, like traveling…?

Chris:

No. To the White House. The President was not there, just to be clear.

Debbie:

He lives there so it’s okay.

Chris:

The National Security Adviser was there and the director of the Peace Corps was there ’cause they were trying to encourage people to study abroad. And I did get a chance to interview the head of the Peace Corps who was a fascinating person. It’s still an episode of Amateur Traveler about that. But no, the president was not there. 

Debbie:

You were at his house so that’s the closest, right? That’s good enough.

Chris:

And then, the actual meetings were off in some office building, the federal office building, which looks like the oldest building you had on campus in college. As long as you went to the campus, in an Olds College on the East Coast. Not at all a fancy place.

Debbie:

You’ve done a lot of different things and I do agree with you in terms of when you are interviewing all of these people. And I’m sure you’ve interviewed hundreds and hundreds of people already throughout over a decade of doing this already and you do learn so much, right? And you make so much friendship from these connections that you have.

Chris:

Oh, yeah.

Debbie:

I’m pretty sure you have all of these people in mind, what has been something that really stood out to you? Maybe you’ve learned a lot or you’ve made really good friendships from these interviews that you’ve had with your show.

Chris:

Well, the friendships truly stand out and a lot of those got started in the podcast and then got cemented in the real world with conversations with people when I met them, especially at the travel blogging conferences. 

The TBEX conference, I’ve been to all but one, where I met some of the people that I met online for the first time. I think of Craig and Linda from the Indie Travel Podcast, they have podfaded that show but are still friends with them, or Gary Arndts from Everything Everywhere. A lot of people that I’ve gotten to know that way but I think of the stories.

So for me, the medium is about storytelling and I think of the best stories that were told, I think, for instance, of a couple who were from Canada and they biked across Iran – something I couldn’t do as a US citizen ‘cause you need a little more supervision if you travel to the country of Iran. But they were trying to get across the hospitality of the people they met. 

Then they told the story: they stopped to use a payphone because they were going to call ahead to some of the embassies ’cause they were biking across Central Asia next. And the payphones are apparently notoriously unreliable in Iran and so someone stopped, some stranger saw them at the payphone and said, “The payphones don’t work that well, would you like to use my cell phone?” 

And then somebody else stopped, and then somebody else stopped, and then somebody else stopped, and they sent me a picture of five different people on five different cell phones calling the embassies, just trying to help some stranger that they had run into. 

And so those are the kind of stories that I remember and cherish from the times that we’ve done this. And then I think of the trips that we talked about and then I was able later to do Zora O’Neill who’s a travel writer, has been on the show, I think, three times.

The first time she came on, she talked about the Yucatan Peninsula and she talked about Chichen Itzá in Cancun and all of those places but she also talked about the Ruta Puuc which is this smaller area of Mayan Ruins near Marietta. 

And she described it and it sounded so cool that we did it years later and we’re able to go down and we went to Marietta on Sunday as she recommended when there was the fiesta in the town square and ate $1 street tacos, which I think is still the best meal I’ve ever had in Mexico. 

And watching the people dancing the traditional dances, and then headed down to a cave where we were seeing 10000-year old cave art. 

Debbie:

How many places would you say you’ve actually visited because you were inspired by your interviews?

Chris:

Oh, gosh. So it’s hard to know now. 

I think I counted one time that when I started the show, I had been to 20 countries. And now I’ve been to maybe a dozen. I hadn’t been all that many actually, when I started the show, and then  now, I have not been to Antarctica and the other six continents and I have been to 60 to 80 countries depending on how you count

 So I’ve been to a number of different places now and quite a few of those were places that I really wanted to get to after we talked about them. But some were also opportunities when the tourism board for Jordan calls you up and says, “Would you like to come? And we’ll pay for everything and we’ll give you a guide and a driver to drive you around Jordan for 10 days.” You’ll say, “Yes.” 

And that’s one of the reasons that I was working my way into part-time work and planned to do that again. It turns out that two years ago wasn’t a bad time to get a full-time job because I’ve been working full-time through this time of year where it’s a little more difficult to travel. But you don’t plan to go back to part-time work so I can say yes to various things. 

I did have to turn down a trip in 2019 to Greenland and you hate to say that.

Debbie:

Yeah.

So with everything that’s happening the last, almost, 2 years now with the pandemic, how has that changed your content in what you’re doing with your podcast and your blog? 

Chris:

It hasn’t, which is a challenge.

And there were definitely a few voices that said it should. There was definitely one person who left a one-star review. Life is Amateur Traveler but let’s face it, travel is dead because of the Chinese-started virus. I think it was something like that. 

Debbie:

Oh, my gosh.

Chris:

It’s like, “Okay, you don’t miss all the lefters who stopped listening,” Let’s just say that. But I’ve heard  many more things that would say, “Thank you so much for continuing to talk about travel because we’re still dreaming of travel.” Even last year when people we’re not wanting to get on the plane.

I didn’t get on a plane at all until I was vaccinated this year. I’ve got a couple of international trips now this year in between peaks of the pandemic. And we’ll probably do more but didn’t want to get on a plane.

But we kept talking about travel. The only thing that’s changed with Amateur Traveler is they used to say that, “I’d like to talk to you if you’ve been there within the last year.” We’ve relaxed that a bit in, like, 2 years but we’re talking to people who are still on the road.

We’re in New Zealand when it locked down. And so have spent the time exploring New Zealand or think this week, we’re talking to somebody who returned to Ireland. He was working in the US and then the pandemic came and, spent basically the pandemic time exploring his own country and didn’t know it that well. 

And so there are still people who are on the road. There are still people who have stories to tell, and I’m still dreaming about travel when we were young. I suspect a few of them may be as well. 

So that hasn’t changed as much. The big difference is for the blog. I tend to blog about things that I’m doing. So, I have done some older articles. When I started blogging, we were writing a lot shorter and smaller articles. And so most of those have come back off the blog, or I would put up trip journals. Trip journals really weren’t written for anybody else, they were written for me.

And so, I’m taking some of those and turning those into articles and doing some research to make sure they were still current and things like that. 

But then I’ve also just focused more on California, which is where I live. And so, my California travel blog, CaliforniaTravelMedia.com, has actually grown during the pandemic because a lot of people, like me, didn’t want to get on a plane. And so, if we were traveling, we were just traveling within the state. 

And we have one-tenth of all the people in the US who live in the state. So that is still a fair number of people. And you see go up and down with the news about the pandemic so the traffic that day that we started locking down, most travel blogs lost about half their traffic overnight. 

Debbie:

Yeah. Absolutely.

Chris:

The podcast is less so. The number of listeners per episode, I will get 11,000, 12,000 listeners within the first month, 15,000 by about three months. That hasn’t really changed that much. The numbers have gone down but they’ve gone down because that was for the new episodes. It’s the older episodes that aren’t getting as many listens because people will come back and listen to that show before they go and when they’re not going, they don’t download.

Last year was still the third biggest year ever for Amateur Traveler as a podcast. So the podcast tends to be harder to grow and more sticky once you have grown that audience. So that’s kind of the good news, bad news with that. 

But again, we saw the number starting to rise and then the delta spike came around and they dropped again. I lost about a third of the traffic for the California blog here in the last two months. It’ll come back, we’re starting to see the numbers trend down and the numbers will come up again as more people are searching for travel.

But it is what it is right now. It’s a good time not to be trying to make your living as a travel writer, travel PR person, travel bloggers. In the travel industry, it’s tough and it’s been kind of nice for somebody like me who’s been doing this for 16 years but makes his living as a software engineer. 

I don’t make my living as a travel writer and it’s harder.  It’s a whole lot easier to make your living as a software engineer.

Debbie:

Yeah. And you could, though. You could technically just leave all of the techs behind and do this the whole time.

Chris:

I could but I’ll have to leave my wife behind as she did not want to get on the road. 

Debbie:

Your wife would be like, “No, thanks.”

Chris:

I’m rather fond of her. We’ll be together for 40 years coming up here in November. So, we were married when I was too young to participate if we’d had a test of the weddings. 

So at this point, I don’t really want to leave her behind even when she’s planning on retiring in a couple of years. And at that point, I think we’ll, “Hey, I work remotely now. My company has no headquarters.” 

And so we have one person who’s working from the south of France normally although this week, he’s in San Diego because he wanted to go to San Diego – he’s all over the place. And one who’s in Portland, I’m in San Jose, three people are in Boston, one is in Guadalajara, and that’s it. We’re just really seven people.

So I could work from anywhere as far as the company is concerned. We just have to work out time zones and things like that but I’m not sure that my wife is going to be ready to go on the road full time. So we’ll just have to see what she’s interested in. 

Debbie:

Yeah.

Chris:

She’s like, “What would I do while you’re doing that?”

Debbie:

That’s true. She’s like, “What? Am I going to get bored? I don’t know.” But that’s good, you’re very caring in that sense. I’ve heard people say, “No, thanks. I’m going to do this on my own. Bye!”

Chris:

Well, she does let me go to places she doesn’t want to go to on her own. So the first time I went to Thailand, I was at a conference in Thailand, I think the first time I was there. 

And she didn’t want to come, I was really surprised, “I don’t understand why you don’t want to come. I feel like you got the wrong impression of Thailand. What are you picturing?” And she said, “I’m picturing it’s going to be hot, humid, and chaotic.” I’m like, “Oh, yeah. There will be those things. You’re right.”

There are some places that don’t make her list that make mine although we’ve grown her comfort zone over the years. She has now gone to places where you can’t drink the water. She has now camped in Africa and camping itself is not one of her big favorite things to do but she said she would do it once. 

And as we were on this Overland Safari with the people from Amateur Travel and listeners of the show, she started talking, “Well, next time we come.”

Debbie:

Oh, that’s nice.

Chris:

I might have changed and mixed a little and stayed with some but her comfort zone is growing.

Debbie:

She at least tries it, right?

Chris:

Sometimes.

Debbie:

You’re getting her out of her comfort zone, which is nice and she’s at least willing to try some things and she’s not opposed to everything, which would be a nightmare if this is something that you really love to do. But I love that you guys are willing to give each other something and take something too. 

So, Chris, let’s fast forward to about 20, 30 years from now, and you’re looking back at your life…

Chris:

You’ll have to speak up. If I’m 30 years older I’ll have a hard time hearing. When I talk about the age of my father, I’ll know what 30 years from now would look like.

Debbie:

You’ll need your hearing aid for everything right? 

Chris:

Yeah. Well…

Debbie:

What legacy would you like to leave and what do you want to be remembered for?

Chris:

It’s really hard because, unless you’ve written a great American novel or something like that, I don’t know that podcast will be long-lasting. People will still be remembering what we do now in 30 years. 

So I think I’m more likely to be remembered by friends and family. And I basically just want to be remembered as somebody who made their life better to hang around here than not. We want to be somebody who is leaving a positive imprint on the world whether that be sustainable travel or just fun to be around. There’s a gamut of things there.

Debbie:

Yeah. And that’s a lot to unpack with your life so far, Chris, ’cause you’ve literally done pretty much everything that you wanted to do. 

Chris:

No, no. There are lots to do.

Debbie:

So what other things are you planning with your life? ‘Cause I’m like, “Oh my gosh, you’ve lived, like, a hundred lives already.”

Chris:

Well, one thing, there’s a lot more travel than I’d like to do. And one of the things that’s different: so when you’re my age instead of your age, I have a friend who said he got to the point where he started reading a book, and if he didn’t like it 20 pages in, he would stop reading because he realized he only had so many books left. And I definitely see that with trips. 

I was in the Philippines five years ago, maybe, or it was longer ago than that, in the Batad Rice Terraces, which is a UNESCO world heritage site up in the north island and it nearly kicked my butt. 

You’re hiking up and down these rice terraces in the tropical heat and it was hard and I was not having a hard time as there were seven of us on this press trip and three of them didn’t do the second one. There were three who were faster than me, three who were slower than me, and me in the middle in the first one. 

And the second one that we hiked, I was the slow guy. I was the one that you were having to wait for. And that was one of those things that, “I’m glad I’m doing this now.” And definitely those kinds of trips that you can’t do when you’re 80, at least, most people aren’t going to be able to.

When you’re 80, you can do the Rhine River Cruise or something like that. There are trips that you can do. And when you’re ninety, we watched our parents not travel. My father was a frequent flyer. He was in the Hundred Thousand Mile Club, more than a million miles on United, for instance.

He knew the travel system so well that he visited me when I was in college on his employer’s dime because he found a way to make it cheaper for him to fly to Ohio via Upstate, New York for the weekend and save the company money so they didn’t mind him adding that on to it. 

He knew his way around the airline schedules, especially in that day and age which was shortly after deregulation. But now, getting up and walking to the dining room is a hard thing. And so there are only so many trips in my future. And so it’s one of the reasons why I didn’t want to do the traditional wait until you retire and then travel like my parent’s generation did.

‘Cause they traveled for about 4 years and then they didn’t have the money. And then pretty soon, they didn’t have the strength.

Debbie:

Yeah. It’s that mentality that you have to enjoy your life – after. When you’re retired.

Chris:

Yeah. I tried not to do that while at the same time, paying the mortgage and doing a fairly traditional life from some respects – I’m sitting in a room in my house. But it is a balancing act to try and figure out what you want and to live intentionally, I think, is really what I’m trying to do.

Debbie:

Yeah. That’s a really good point to all of this because there are different stages in your life. When you’re younger, you’re able to do things, like you mentioned, that you can’t do when you’re sixty or eighty years old. 

And I feel, like, there are different times for that and you really have to be able to appreciate it when you can because you are never going to get back that time again. And then when you’re 60, 70, 80, 90 years old, there’s going to be a lot of what-ifs: what if I had done this in my twenties or thirties or forties?

Chris:

And I remember hanging out in London, I mentioned Craig and Linda from the Indie Travel podcast when they were still podcasting, I think the first time we met in person was in London. It’s a little hard to remember if it was the first time because we’ve been listening to each other’s podcasts for a while so we knew each other. So, it’s hard to remember when we actually met in the real world 

I was working a full-time job and they were making more of the traditional nomadic lifestyle and teaching English along the way and things like that. Neither of us was quite happy with where we were in terms of the next of things because I wanted to travel more. I had the money to travel but not the time and they had the time but not the money. 

We sit somewhere in between. Somewhere between it seems like there’s a good mix. And for me, for the six years that I was doing it recently as a part-time worker, that actually was a pretty good mix. 

I’m not looking to be on the road twelve months a year but I was on the road about a third to a quarter of the year, somewhere in that range. And that let me stay married with a happy wife who could come with me on the trips that she wanted to. And then also get out and explore the world but also still be saving money for retirement when I can do it more full-time. 

So that was a good mix for me at that time. 

Debbie:

And it’s nice to understand where you really fit because everyone has their own way of living their life the way it fits them. So, in order for you to do that, you really have to go out there and try it, which way really works out for you. And once you find that, it feels so good. 

Thank you so much, Chris, for being here and joining us today. We really appreciate you. If our listeners want to know more about you, where can they find you?

Chris:

The spot is AmateurTaveler.com, everything is all linked from there. 

Debbie:

Perfect.

Thank you again, Chris. We really appreciate you being here and we can’t wait to listen to and read your travel adventures. 

Chris:

Thanks for having me.


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Show Credits:

Audio Engineer: Ben Smith

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