HTS Podcast 3 with Chris Guillebeau


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Welcome to the third episode of the Hack The System show!

You should subscribe to this show on iTunes.

The Hack The System Podcast is your access to interviews with the world’s foremost experts on blogging, lifestyle design, traveling, and life/system hacking. In short–you’re going to learn how to kick ass.

In this episode, I sit down with Chris of The Art of Non Conformity. Chris has been one of the five most influential bloggers in my life. He made a goal to visit every country in the world by the age of 35—and he’s en route to achieve it, having visited already 180/193. Meanwhile, he runs one of the most sophisticated online businesses I’ve seen. His most recent product, How to Write, Sell, and Publish Your Own Book, is the most comprehensive resource for publishing your own book that I’ve ever seen (and this is coming from someone who’s written 6 published books). You might have seen my recent review, How to Hack Writing Your Own Book.

Chris has been a huge inspiration for me, and you’re going to learn a ton of info from him. Below, you’ll see a list of things to listen out for–and a full transcript of the conversation.

Transcript of the Podcast Episode


Don’t forget to subscribe to this show on iTunes.Maneesh: Hey guys this is Maneesh Sethi, your number one digital nomad coming at you live today from Portland, Oregon and I’m here with one of my, basically, heroes. This is Chris Guillebeau from the Art of Non-Conformity and I’ve been following Chris ever since you launched your first manifesto and I remember reading through it and being, I’d just started travelling at this point, and I remember reading through it and being , this is exactly who I want to be, I want to be able to build a tribe and also design an ebook, that’s this pretty. And I think I really started getting into your stuff when you started doing your frequent flyer challenge and so Chris, do you want to go ahead and introduce yourself to my readers? Most of them know you but..Chris: No, that’s great you’re a hero of mine as well and I love what you’re doing in traveling around the world and doing all of those pushups on tops of elephants so it’s inspiring to me as well. So I produce the blog “The Art of Non-Conformity” and a book and a couple of related businesses. I’ve been travelling for about 10 years, I lived overseas in West Africa for about 4 of those years, I was volunteering for a medical charity, that kind of gave me my start in a lot of different things. After I moved back to the States, I did a useless Graduate school program and decided that I wanted to be a writer and so that’s when I wrote the manifesto and that’s when I started publishing on the blog and travelling and doing everything that I’m doing now.

Maneesh: So Chris you had this idea of approaching and reaching every single country before you turn 35 right, when did you have that goal, when did you decide that that was what you wanted to do?

Chris: Yeah, I think I’ve been travelling to maybe about 50 countries or so and I was just on a train once so I counted up, hey where have I been, listed all that stuff out and maybe I was 25 or 26 years old then and I was like, it would be really great to go to a hundred countries. I wanted to make that my goal. And so I started thinking what does that look like, what is that going to cost, what’s the time investment, how long will it take and I started working towards that and then I realized that in some ways a hundred countries is kind of an easy goal because you can pick and choose, which countries you go to, you can avoid the hard ones. And so I was getting closer to a hundred a lot sooner than I expected. And so that’s when I thought why not go to every country in the world and I tend to believe that a good goal always has a deadline, otherwise it’s just a dream and so I was , let’s see , I was 30 years old then, let’s say 5 years , it’s about time I’m 35 I want to visit every country in the world. So that’s how it came about.

Maneesh: And so which countries are left then, what are the most difficult ones you’ve got left on your trip.

Chris: Well I’ve been doing a lot of travelling over the past few years and I only have about nineteen, in fact exactly nineteen countries left so, I just came back from Cuba..

Maneesh: Shhh…[laughing]

Chris: Right, exactly. Even though I’m an American, it’s all good. No, nineteen countries left, probably at least half are still in Africa. I’ve been travelling in Africa for years but there’s fifty-two countries there so it takes a while. Also a few of the “stans”, I think I still have Takejistan and Turkmenistan, a number of countries in South Pacific that are just hard to get to, limited flight schedules and then I ‘m saving Norway for the final country. I’d hope you’ll come along.

Maneesh: Definitely, I was actually going to mention that Norway, I’ve been there at least three times every year for the last, three or four years and we’ll have a lot to talk about Norway, I think.

Chris: Awesome.

Maneesh: But what has been the most difficult country so far for you to go to?

Chris: Yeah that’s interesting. I’m trying to think of what the most specifically difficult one was. A lot of times now I’ve ran into issues with visas, that’s honestly my biggest challenge more than anything else is I have two passports but with that I’m always constantly sending it back and forth to Washington DC or somewhere and it’s like being stuck for weeks and weeks. Saudi Arabia denied me at first and I went anyway, it turned out alright. Pakistan, I also showed up without a visa and it ended up being ok. But there’ve been a lot of touch and go moments where I cannot be sure whether it would come through but then I kind of just go for it because I realize if I don’t then I’ll miss the deadline so, so far so good.

Maneesh: What about , the islands, have you ever had a situation where there’re no planes coming into a place, where you had to get there by boat?

Chris: Have I ever been in a situation where there are no planes. There’s usually a plane somewhere, to be a country you have to have an airline and a beer. Every country in the world has a national beer and some kind of national airline even if it’s not operational. There’s some way to get there so I don’t think I’ve ever been “stuck” stuck. I was in Afghanistan and my flight was cancelled and delayed for four or five days, I wasn’t too excited about that. But then , I found another way out and I made every mistake, I’ve bought tickets multiple times, I’ve showed up at the wrong day or the wrong airports and lost things or whatever hardships but I mean, mostly everything works out.

Maneesh: Yeah, it always works out.

Chris: It always works out you know that from travelling, right?

Maneesh: Exactly. But have you ever had a situation like when you go to countries you spend just a few days in most countries, right?

Chris: Yeah it depends because I’ve been doing this for a while; some places I’ve spent quite a lot of time but in some other places it’s just a few days, it just depends.

Maneesh: Ok and which country have you found to be your favorite one, the one you’d go back to?

Chris: I’ve got a lot of favorites, I really like South Africa, I lived there for a few months back in the day and, what else do I like, I like Lithuania, Macedonia, some [inaudible 5:21] countries in Eastern Europe, other parts of the world, I like Hong Kong I go back there quite a bit.

Maneesh: You kind of have to go through it to get to other countries.

Chris: Excatly. What about you what are your favorites?

Maneesh: I tend to like Argentina as my favorite.

Chris: Yeah, of course.

Maneesh: Italy, I lived in for a while and I really like Norway so..

Chris: Ok.

Maneesh: I think you’re going to enjoy that a lot.

Chris: Excited

Maneesh: Have you spent time in India as well?

Chris: I have yeah.

Maneesh: Where were you?

Chris: I went to Mumbai and then I travelled around the country by train so I went to Hyderabad and then I went up to Calcutta and then I was supposed to go from Calcutta to Dacca, Bangladesh and but I had a visa problem there. India gave me a journalist visa when I went, which I learned you never say you are a writer when you’re [inaudible ]going to a country and applying because they’ll give you a more limited visa so I had to go back to Bangladesh later but yeah I had a great time in India.

Maneesh: So you mentioned that you have two passports, those are both from the US, right?

Chris: Right.

Maneesh: I’d actually always wondered about this because I don’t have a dual passport in the sense that the two American passport that you can flip back and forth but do you think you can possibly go to Europe with one passport and then leave for a week and then come back and switch the dual passports and continuously stay in Europe for more than three months at a time?

Chris: Oh interesting. Ok I see what you’re suggesting.

Maneesh: Because I keep getting kicked out of Europe and I was wondering if you can do that.

Chris: Oh, I see. You probably couldn’t legally do it. Would it work? I don’t know. It might.

Maneesh: I’ve always wondered..

Chris: Its probably like going to Cuba, you’re not supposed to do that but I was just there last weekend. All is well.

Maneesh: I’ve always wondered about the scanning right because they scan it but does it remember, is it just reading your passport or they actually write something to their notes?

Chris: There is a record, now every time you get your passport scanned there is a record.

Maneesh: Ok.

Chris: And you can actually request that record. You can file a Freedom of Information Act request and you can see all the data on your passport which is really fascinating and so I did that. I sent it off and it was thirteen dollars or something. You get this huge printout of every time you entered the country or exited and it also has all your flight details which is kind of weird, I didn’t realize that your flight details go in that same data.

Maneesh: Where or how do you file a Freedom of Information Act request?

Chris: I forget the information off hand but if you just Google, file for Freedom of Information Act request for your passport history, you’ll find that.

Maneesh: Perfect. So these kind of strategies I love talking with you and with some of the guys that I’ve also done interviews with about kind of taking advantage of the system, we’re trying to find ways to get around what most people would do when they want to achieve a goal and so, for example, when most people think about travel, they think how much it costs or how expensive tickets are when really, ever since I’ve been reading your blog I haven’t paid for tickets.

Chris: Right, awesome, that’s great.

Maneesh: Yeah, I don’t think you’ve had me on your frequent flyer challenge list but I have five hundred k miles.

Chris: Five hundred thousand miles, dude, that’s awesome .

Maneesh: That I get from your advice.

Chris: That’s incredible, that’s great dude.

Maneesh: So can you talk a little bit about frequent flyer miles, how many have you accrued so far?

Chris: Ok, how many have I accrued so far. Usually I go through about a million a year so it’s like a constant cycle of earning miles and then redeeming them for trips just like you’ve done. Probably the most critical point is that most frequent flyer miles are not actually earned through flying so even though I’m earning a million a year probably two hundred thousand of those are through flying so it’s a lot of flying but still, the vast majority of those miles are earned in other ways. So these days, there’s an incredible number of promotions especially through credit card bonuses, if you have good credit and you’ve been responsible, you’re going to apply for a credit card, these days the average sign up bonus is at least fifty thousand points, which is great that’s two frequent flyer tickets to anywhere in North America or of course, you can put those miles to better use flying overseas. Lots of other different registration bonuses the, whole world of travel hacking, what I call it is basically using frequent flyer miles to your advantage, to work the system exactly as you said.

Maneesh: Exactly. Have you found any deals that are currently that are the best? What would you recommend for somebody signing up today, what should they do?

Chris: What they should do today? Well I think probably the first thing is just to familiarize themselves with some of the terminology and in what’s going on, we just finished the US airways grand slam promo which is this kind of promotion that comes out every year, you accrue hits through certain activity and then that translates to miles so that’s closed now but it comes around again every year and there’s a few things like that. As I mentioned, credit cards, a couple of different cards that you can apply for right now, the Chase sapphire card is a good one that has a fifty thousand point bonus.

Maneesh: Is that with a specific airline?

Chris: No, it’s not and the good thing about that one is that it can be transferred to a number of different airlines or hotels as well.

Maneesh: Ok.

Chris: That’s good. I also like some Amex cards, also, Amex business cards does the same kind of thing where it can transfer to different airlines, Starwood preferred guest cards, Citibank American Advantage card, you can get a Visa and a Mastercard and another thing most people don’t realize is that even if they don’t have a business, they can apply for a business credit card. You just apply for it in your name with your social and if you’re accepted for the consumer card, you’ll most likely be accepted for the business card as well [inaudible 09:58] doubles your miles. You probably do that.

Maneesh: Yeah many, many times.

Chris: You can explain this probably much better than me.

Maneesh: So Chris, you’re on this travel hiking cartel which is probably one of my favorite subscription service and this travel hiking cartel is basically a service which sends you an email every time there’s a new credit card offer or there’s a new promotion that will help you earn miles and I was always impressed because you don’t use affiliate links. If you were using affiliate links on those credit cards you would have billions and billions of miles by now.

Chris: Right and probably a lot of money as well because they pay out quite a bit of money yeah I just I don’t obviously have a problem with the affiliate stuff, I just chose that my business model for that I wanted to have a subscription service and I know some other people who do it differently. They have a blog, they don’t charge for the content but then they do run that affiliate so there’s just different ways of doing it.

Maneesh: I remember my brother Rameef, my brother Rameef who was friends with Chris also, he sent out an affiliate link for Starwoods card which is one of the best cards we’re going to use for and I think overnight he earned a million miles or something.

Chris: More than that, he told me, I just asked him about it when I was in New York, I was freaking out, yeah.

Maneesh: I remember he was laughing because he mentioned something about you not having gold status or something.

Chris: All he has is gold status, the platinum status is much higher so gold status they pretty much give to everyone whereas platinum status, you either have to earn it the hard way which I would never do or I’d got a status match so basically I had a higher status with Hilton then I asked them to match it, they gave me that status so what’s funny is that Rameef has so many more Starwood points than me, I think I had eighty thousand which I thought was a lot and then he said he has two million or something from one email but he has this massive influx of points but yet he doesn’t get the same upgrades and free breakfasts and free internet and stuff that I get even though I never pay to stay in Starwood hotels. But still, two million points is pretty good for me.

Maneesh: It’s pretty good and my brother’s great. He flew me, we were having a family cruise going out of New York and he bought me a ticket with this Starwood points, he’s very nice but then he makes me so angry sometimes because he was just like, “Yo I just spent thirty thousand miles in upgrading to an emergency seat row.” I’m like, “NO!”.

Chris: Yeah, poor evaluation I think his thinking is: when he has that many miles he just doesn’t care, right, but if you had a more reasonable amount of miles,like five hundred thousand which is still huge, then you want to be more careful about your evaluation.

Maneesh: And so what airlines do you tend to use the most?

Chris: Well a lot of it depends on availability and where I’m going and these days it’s kind of tricky because I only have less than twenty countries left so I have do a lot of repositioning and things but maybe in other questions like what airlines are the best and how can you put these miles to good use so generally, the US airlines are the worst, European airlines is maybe a little bit better, Swiss Air is nice I like them but then the Asian airlines especially Singapore Airlines, Cathay Pacific, Japan Airlines, those are my favorites.

Maneesh: What about the alliances though, which one do you prefer?

Chris: Oh sure, so I’m usually in One World these days because I have my highest status in American but then I also have a lot of Starlines miles too so either one where there’s Starlines.

Maneesh: Yeah, I noticed a big downside to Starlines is you can’t do one ways usually, just with United , right?

Chris: Yeah exactly and availability seems to be more difficult these days with Starlines.

Maneesh: I’ve been trying to route some flights into Africa, inter-Africa, from Nairobi to Cape Town or something like that. Have you ever done anything like that, flying one way or round trip that way?

Chris: Yeah sometimes you may have just to get the round trip reward and keep it open for a year and maybe use the other segment..

Maneesh: I think One World maybe doesn’t have very much availability or something in Africa.

Chris: That’s correct. One World just has Comair which is based in South Africa it’s a British Airways subsidiary there so definitely Starlines has more coverage and also even Skyteam with Kenya Airways.

Maneesh: Ok. It’s not Skyteam though..

Chris: You get Sky pesos which is what they call their currency, it’s called Sky miles actually but it’s a devalue so it’s called Sky pesos.

Maneesh: I have all these guys..

Chris: Sky rupees or something you know what I mean?

Maneesh: Sky rupees..

Chris: It’s a good term.

Maneesh: Sky Icelandic cronities [inaudble ]

Chris: Right, right.

Maneesh: So with your travel hiking cartel, it seems like it exploded recently when you got a media mention, right? You had to know like fifteen hundred new subscribers or something..

Chris: It was a huge number, it was a big thing, it was like a thousand or something in a couple of days and that came from, I think there was an MPR story, there was cover and it got picked up by yahoo and some other sources and the funny thing about that is I didn’t pitch for that and I had no idea it was even coming out. I was actually travelling in Africa, in Madagascar and I went to bed over on that time zone and I woke up in the morning and there was this huge influx of activity, new subscribers and email and everybody was like, “Hey, I heard you on MPR” and I was “ I wasn’t even on MPR” but apparently I was so that was nice.

Maneesh: That’s pretty cool.

Chris: It’s for me two million [inaudible 14:30] points or something.

Maneesh: But when you suddenly got this huge influx, did that more than double or triple your subscriber base? Or was it just sort of a percentage growth?

Chris: No, It was quite significant, I think we were maybe about 2500 subscribers then and then a thousand increase and I guess the thing I was curious about is how many of them will stick because a lot of these people, I don’t have a relationship with them, they just heard this on the radio and it’s been more than I expected, I expected a huge, huge drop-off and there was a drop-off but I would say that was several months ago and at least half of them are still here so..

Maneesh: Wow.

Chris: That s good.

Maneesh: Half of them stayed.

Chris: Approximately.

Maneesh: That’s amazing.

Chris: Actually I do very poor tracking and matrix and statistics and things like that but from what I can tell about half are there .

Maneesh: You keep it steady. So how many subscribers do you have now then?

Chris: Its right about 2500, it’s always some people are coming in some people are leaving I want to make sure I hold the line at 2000 – 2500, I feel like that’s a pretty sustainable business, I’d like to keep it there.

Maneesh: Yeah that’s a pretty high number too at 15 bucks a month that’s pretty amazing. So you have several products actually, you have the empire building kit, you have the travel hiking cartel, I’ve been checking out the empire building kit and a few other products they’re awesome, the content and quality are really good.

Chris: Thanks.

Maneesh: But I was wondering form a financial perspective, which one tends to do the best for you?

Chris: Ok probably, the empire building kit that you mentioned and also I did a product a few years ago called the “Uncomissioned Guide to Art and Money”, it’s an information guide for artists, to help artists become more familiar with actually making money because a lot of artists are really good, they’re art but they’re not so good with the business side of it so that a pretty interesting product because it wasn’t a huge launch or anything but it consistently sells. I do absolutely nothing at the market but it’s there so I kind of like that because I think, in this business you can often become launch dependant or dependant on media stuff which we have no real control over so I really like having things which just have a life of their own so one of those would be up there.

Maneesh: Ok and so when you launch a new product, how do you research what you’re going to launch because you have 4 or 5 of your own products plus you have products that other people have written that are on your site?

Chris: Yeah, co-developed kind of.

Maneesh: How do you decide what you’re going to write about?

Chris: Sure. I don’t know if research is the right word because I don’t really do much really in terms of..I like market research and survey groups. I’ve done some of that in the past, these days I have a pretty broad community and so I would say probably the main thing I do is listen to my community and I try to pay attention to what they’re asking about and I always encourage people, if you’re starting a new blog or if you plan to develop plans or services, listen to the questions that you’re being asked and pay attention to if you’re being asked the same questions over and over that means people perceive you as an authority on this topic and it also shows you that they have a need to learn something and so in my case it was always about travel and self-employment, how do you travel around the world and how do you pay for this and how if you never had a job. How can I learn to develop things online so everything I developed is in those two tracks but that pretty broad so then I get more specific, I get more specific based on what I’m motivated by to be honest, if I’m really excited to do something that’s what I develop.

Maneesh: Its true and it seems you really love frequent flyer miles and you do love having world domination and building empires. I love the names you use for items. JD was mentioning, JD Roth we just interviewed, was mentioning that you were doing a meeting for the world domination summit I was like, “World Domination Summit “.

Chris: Right well World Domination Summit is a good example for a name that’s polarizing because a lot of people hearing are “wow that’s awesome” and then there are some people that hear it and say “that’s stupid”, that’s fine, that’s great so it’s not for them but I like to be interesting and it’s a crowded world that we live in and everyday you’re getting thousands of messages and you want to stand out so that’s why “Empire Building Kit”, “Travel Hiking Cartel”,“World Domination Summit”, whatever.

Maneesh: The World Domination Summit is, well you talk about that what is exactly the World Domination Summit?

Chris: It’s a gathering if interesting people. I went on a book tour, I went to all 50 states and the thing that I learned out of that experience is just how interesting not only my community but also awesome people all over the place, how interesting and amazing they can be and the funnest thing is gathering them together and exchanging ideas. And so I thought what if we could do this not just in Ohio or wherever but with people all over the world and so last year we did it for the first time and we had about 500 people from 13 countries so we had entrepreneurs, we had lots of digital nomads, we had artists students, travelers just kind of fun people so we bring them together, we do some presentations, we have some main stage talks, we also have lots of workshops, breakout session and then the other part of it is just kind of providing a space for possibility, seeing what happens.

Maneesh: How does it feel to be the king for a 3 day period?

Chris: I don’t think about myself that way.

Maneesh: Yeah.

Chris: It’s funny. If everything goes well the you’re the king but if something goes wrong, you’re the jester or something so that’s what I’m thinking of.

Maneesh: I remember I went to a conference in Finland, it was a persuasive technology conference and this guy BJ Fog who invented this topic and I went there and every conversation by every group I had threw in the word BJ Fog at some point and BJ was like, yeah I love it it’s great except I get to be famous for these 3 days and I disappear and nobody ever recognizes me again.

Chris: Right exactly after that. I think there was Maggie Mason, this blogger, she coined the phrase “famous among dozens” and that’s how I feel as a blogger I feel like people are that way, there are certain people who know you and you’re well known in this very small circle but you walk down the street it’s not hey maneesh or hey chris you’re not really a celebrity.

Maneesh: The first time I ever felt that way was actually in New York when you were doing the first stage of your book tour, I went to the after party where you’re at and 2 people recognized me from my you tube video and that would never happen ever, that was a self selected group of people who follow [inaudible 20:34].

Chris: Right exactly so it’s a weird thing you’re well known among your people but not elsewhere.

Maneesh: I know.

Chris: So you can’t get it let to your head too much.

Maneesh: I definitely can’t. So I think a lot of the people are really, really interested in figuring out how you go from nothing, just staring to building a blog and I remember your strategy was amazing and I was kind of modeling my launch strategy after which is build 3 months of content, I remember you saying have 3 months prepared and ready to go before you do anything and then throwing out an ebook and then doing an explosive launch like that. How would you recommend to somebody who’s just getting started, a digital nomad or a new blogger to build their first platform to build their piece?

Chris: Oh great question I think we can say something about each of those points so first thing about building up the content. I think I may have done almost 6 months though I didn’t actually use all if it, so probably more like 3 months as you say. My concern was, I studied a lot of bloggers and I can see what went well and what didn’t go well and I saw lot of people start well but then they just kind of just drop off and you can see this loss in motivation and they’ve been missing their schedule and so for me and also, I was worried about myself. I was worried I’m going to start posting and then I’m going to just stop and lose my motivation so I wanted to have that backlog. I wanted to let me see if I can become comfortable as a writer and build up this backlog of content and then when I launch it, I’ve got it. I want to keep writing new stuff but if something goes wrong one day or I don’t have my post at least I can pull something from there. So that was important for me. The ebook or the manifesto was important in creating what Chris Garett calls flagship content so that pretty much means if I go to your blog, I don’t know you, what are you all about, what’s the big thing about Maneesh how can I learn that so for me, that was the first manifesto which was a brief guide to world domination and then I would say that probably the single most important strategy for me, besides the consistency and just sticking with it and discipline, whatever, the single most important thing was just treating my readers , not only like real people but treating them like important people and I always tell people, they’re trying to figure out what should I do with my blog, how can I attract traffic or subscribers, look if you’ve got 5 readers, treat those 5 people the most important people in the world, because they are. They’re reading your blog. They could be your best friend, your grandma or something like that but just treat them, try to understand what are they about, what do they look to you for and think about why they should care. Start asking them to help like hey, I wrote this post, can you spread it? Hey I might create this product what do you think? What do you want to know about and then just kind of keep that up as you get to 5 to 50 to 500 people who join your email list and give them a little note: Hey thanks for reading, dude, you’re awesome and I think overtime cumulatively, small things really matter I mean I did that for the first 10 thousand people who joined my email list. I wrote them a personal note so it’s a little bit of copy and paste going on but nevertheless it’s still coming from me. And so it’s not like I think each one of those connections is amazing or magical or that they’re really impressed but over time you really are building relationships with people.

Maneesh: It is interesting to watch the difference between, I used to have lots of subscribers and I would never send them any real content, just being auto-responding the series. Since I’ve re-launched it and a little bit before that, I would start to actually try to connect and you just feel better about yourself first

Chris: You do, right.

Maneesh: And then they treat you better, they are actually people, they’re not just a number or an email address. They less like they don’t subscribe or they’re more likely to contact you, but how do you deal with email overload for example? You must be getting a lot of requests or stuff from readers.

Chris: I get a lot of email but I consider it a part of my work, it’s what I do and also I don’t think of email as I don’t know some sort of undesirable technology. I don’t think of it as an email message, it’s a person who’s sending me that message, right. If they took the time to do it then surely I can take the time to reply and I think that people always say that that’s not scalable but if I write Seth Gordon he’s going to write me back, you know? There’s a lot of people if I write, they’ll write me back and so I guess I just see it as an important thing I mean you do learn to get faster ,you do learn to do things in batches, there’s a lot sort of hacks and tricks but I think the more important thing is to think about the relationships.

Maneesh: Ok. And so when your blog was first starting, when you launched your first manifesto, for example, do you recall how many subscribers you grew from the day before you launched to a month after you launched?

Chris: Not sure if I recall in terms of the subscriber numbers but I remember right around that summer was when the subscribers went to 3 thousand to 5 thousand and in that range, I noticed a lot of things happened in that range. That was the range where I first believed I can actually do this, I can actually make a living from it which was not even my goal in the beginning. In the beginning, I just wanted to write. I did want to write a book but I had no idea about creating non-commissional guides or empire building or any of that stuff so it was right about that time when I realized that this was actually a community that could sustain itself and go on to do whatever it is I want to do so, I remember the downloads were over about 6 months, were like a hundred thousand downloads but that does not always mean something, that could just be people downloading and they never connect with you.

Maneesh: Yeah so when you create an ebook, the first part is you build an awesome ebook, that’s the most important part but then how did you promote it to actually get people to download it?

Chris: Well I tried to make a big deal out of it. I said first of all I kind ofstarted with the community so your building up this community, like I said it was 3-5 thousand but before that it was maybe 1500 or something so all those people I would tell them in advance. So I was, hey I wrote this thing and its completely non-commercial and it’s kind of like my world view and what I have to do with the art of non-conformity and it’s coming next week, I try to give them a little heads up.

Maneesh: This is just to your subscribers, really.

Chris: Yeah just a few subscribers, it’s coming and if you like it I would love it you spread the word. Then I did do some direct pitches as well, I did write to people, once it came out, I wrote to a lot of different bloggers. You mentioned JD Roth, he was a friend of mine by then so I sent it to him and I said, hey read this and if you find this worthy of attention, I’d appreciate it if you put it out there and he did and a lot of people did so that kind of helps and it kind of spirals from there.

Maneesh: Did you get guest blog posts or was it just pitched for [inaudible 26:39].

Chris: I think I did a few gust posts, yeah I do think it’s a good strategy if you have a relationship with an established blogger and if they do take guest posts and you’re familiar with the format it can definitely help, sure.

Maneesh: Interesting, it’s really an interesting thing because there’s a big difference between a zero and a hundred subscribers but between a hundred and a thousand it’s like basically the same thing it’s just a linear growth.

Chris: Sure.

Maneesh: But the difference between 0 and a hundred and a thousand to 10thousand is huge and so it seems one of the big jumps in your business was the ebook. What other huge changes were the big triggers that really affected it?

Chris: Sure, manifesto was a big thing, having an actual print book was a big thing.

Maneesh: Was that a big thing?

Chris: It was. These days there’s a huge of focus on digital content and of course I love digital content that’s what I spend my time doing but no, the print book was really great and I also was doing a book tour which was great. I go to these places and not everybody reads blogs out there, not everybody watches podcasts, so the print book was good, the development of the business was good. Travel Quest definitely helped, a lot of different people were interested, watch Chris try to get to every country in the world but there’s so many things I could’ve done better. I’m thinking this list that I’m reciting and there’s so many things I could’ve done better so really the main thing I think was just getting started and putting out those posts, two days a week and being around being around on twitter, responding to email, trying to be a nice guy.

Maneesh: I was always interested by how you have this habit of a thousand words per day, right. Do you keep that up still?

Chris: Yeah.

Maneesh: A thousand words a day. How do you specifically write tactically, do you just go out in the morning every morning and write or is it like whenever you feel like it during the day?

Chris: Yeah, it’s not at all based on the time, it’s based strictly on the deliverable. So basically I wanted to be a writer, I needed to discipline myself somehow and so I created this deliverable of a thousand words a day. So I’m going to write a thousand wordsa day, there’s lots of other stuff that’s going to be happening in my life but no matter what, this is going to get done, 6 days a week. It’s like exercise, you can miss a day and you’ll going to be ok but if you miss a couple of days, you’ll start feeling bad and so I just created this habit so it’s not at all based on time because I’m always travelling around the world doing lots of stuff so it’s not like get up at this time and get an egg timer or whatever but for me it’s a hundred percent about the deliverable.

Maneesh: Absolutely focus on output [inaudible 28:55]

Chris: Yeah, exactly.

Maneesh: And then yeah, you also said exercise, you also run a lot, right?

Chris: I don’t know if I run as much as you..

Maneesh: Not anymore. I used to run

Chris: [inaudible 29:04]

Maneesh: We’ll race on camera one day.

Chris: You’ll beat me I’m sure. I do a long run every Sunday when I’m home so that for me right now is between 8 and 15 miles but I couldn’t do much more than that and then the rest of the week I’d run 15 times a week and I do yoga and I go to the gym but it’s not so great.

Maneesh: Its tough especially with exercise and blogging, there’s so many things that you’re got to do and blogging takes over your world. I was remarking to JD, I just want to write, all I want to do is write and that’s 20% of the time because 80% of the time is editing and dealing with Word Press or whatever. How do you fit everything in your life and still build a business as successfully as you can?

Chris: Well, you have to make time for what’s important to you.

Maneesh: You’re married too so..

Chris: I am that’s right so I was also travelling a lot so when I come home I want to make sure I spend time with Jolie and catch up with her but I would say you make time for what’s important to you and there’s all kinds of things that can crowd out those important things and then you give a day, there’s all kinds of things that you can do. That’s why you have to have this kind of deliverable whether its writing, if you want to exercise, you want to be healthy you have to be like, ok I’m busy, but everybody’s busy . I still have to go to the gym or I still have to swim or whatever they say or [inaudible 30:14].

Maneesh: And it’s cool, it’s fun to watch the difference in the quality of things that happen over time because the more you run, the better you get. I remember reading your first two months of blogging..

Chris: Yeah, it sucks

Maneesh: This is not good.

Chris: I know, no, you’re right dude, its fine. Here’s a very good point and I’m glad you brought this up, every one of your readers or viewers should know this when you’re trying to start a new blog, you should pick a few people that you admire, that you respect what they’ve done. You should go back and read the very beginnings of their blog because a blog is a perfect archive, literally, in that you can exactly see what that person had done, you can see their whole growth and transformation, you can see the mistakes they’ve made, most likely. You can see how they recovered, you can see when they made certain choices and so it’s exactly right, in the beginning I wanted to be a writer and maybe some of it was alright but then other pieces could be definitely a lot better so hopefully every time it gets better.

Maneesh: It’s true, I’m sure that the more that you’ve learned, the more that you’ve written, the more that you’ve grown. You’ve seen what sorts of patterns tends to be successful in different blog posts and which ones tend not to be successful. I was talking to JD Roth about this and he was mentioning the story.

Chris: Yeah.

Maneesh: But what have you found to be the biggest, the best thing you can do for your articles you really want to grow?

Chris: Well, whatever JD said about the story, I’m sure I would’ve also put that at the top. I would say a lot of bloggers make a lot of assumptions and they just assume that their readers have the same history that they do, the same experiences or background, they kind of gloss over things and we just tend to do that naturally in conversations because we talk to people that we have things in common with. If we go somewhere else we might feel compelled to explain more. So I always encourage bloggers explain more. Don’t assume anything, if you’re trying to make a point, think about the objections for that point. You don’t have to respond to them directly but try to acknowledge them somehow, try to weave that in. The more you can kind of delineate things, the more helpful it can be.

Maneesh: Ok and what kind of genre of posts have been your most successful posts?

Chris: This all depends on how you define success.

Maneesh: Let’s say, views or email subscribes, or people or new growth or new visitors.

Chris: Sure, again I’m terrible at tracking and keeping up with things, I really am so mostly it’s more of observations in the general sense I mean of course I see comments and things but comments can also be an important [inaudible 32:29] of engagement because not everybody comments or most people don’t comment so I would say generally, the posts in which I’m sharing something about myself or something personal or some kind of life experience or story that I’ve had but then hopefully finding a way to connect that to a broader principle that somehow relates to the readers, not in a condescending way but hopefully in a self depreciating way or humorous way that will then give people some kind of encouragement for something. And so I guess, I was thinking more of success, I mean, I definitely want page views, I want subscribers, that’s great nothing wrong with that but what I really enjoy the most are email from people who write in and say they connected with something on a personal level and they’ve been struggling with something or they didn’t know what to do about a certain thing and then they read that and that gave them the motivation or kick in the ass or whatever it was to go and do that so that, to me is success.

Maneesh: That’s true. It’s cool when you hear a story from one of your readers about how you really influenced their life..

Chris: I’m sure you’re going to start getting a lot of these as well.

Maneesh: I got my first one from a course I sell online and someone said I watched your course and finally I just launched my first product, now I can quit my job and I’m just making enough money to survive, and I’m like yeah..

Chris: Yeah that’s fantastic.

Maneesh: Yeah it’s a good feeling.

Chris: I have a little ever note file, when I get email like that I put them in there , they’re not public, they’re just for me but I go and look at them because then if you get somebody who writes in and says you’re an asshole, you can go and read this ever note file so that’s very helpful.

Maneesh: It’s funny because you’re completely the opposite of my brother who has only a “kooks” folder.

Chris: Yeah, he told me that and I thought, for me that’s weird because I’d never do that. I don’t want to forget those things.

Maneesh: He got a folder for just crazy people who email him. Sometimes you get crazies I’m sure.

Chris: Yeah, of course but I usually just delete or something, than save them in file.

Maneesh: So I’m interested in knowing a little bit about your travel stories, what are some of the craziest or most interesting stories that you had while traveling in some of these third world countries.

Chris: Yeah the funny thing is for me, I started traveling in West Africa. My wife and I moved to Sierra Leone in 2002, at the time that was the poorest country in the world and we were there for a year. We were in Liberia next door to Sierra Leone for a year and then several other West African countries for the next 2 years and it was like, I was basically starting at the bottom in terms of travel experience and hardships and corruption and bribes and things like that and so after that it’s just got a lot easier. I thought that was normal. I set my travel goal after I’d done ten to fifteen countries there and it would be like overcrowded ferries and I would take flights, all those countries in West Africa, about half of them are former British colonies and half are former French colonies, but none of them get along. So if you’re flying between two countries that are next to each other, you have to fly 2 to 3 intermediate countries en route. It takes 2 days, 48 hours to get to this short distance and I thought that’s how it worked everywhere and then I started traveling to elsewhere around the world, in Southeast Asia or Latin America, I’m like, this is easy, this is like, what’s the problem here? So that’s like my formative time came during those experiences bu I think back and I would’nt trade them for anything, it was great that I got to do that.

Maneesh: I always laugh when people get afraid of traveling to other countries because you’ve been to the scariest countries and you’re goint to central African republic, that’s not very safe compared to Europe. When I was flying to Italy, my mom was like, you’re going to get murdered by the mafia there.

Chris: Yeah well , as you know, there’s very few places in the world that are generally unsafe. There are some but there are 193 countries in the world , the list of really unsafe countries are 5 to10, so the vast, vast majority of people that are watching this or travelling are not going to places inherently unsafe. What I think some people do when they start traveling is they forget basic safety stuff. I don’t know if you’ve noticed this but lots of places I’ve gone, I meet with other Americans or Europeans and we go o this mini-bus or taxi or something and no one wears their seatbelts and I’m like why do you do that, if you were at home wouldn’t you be be wearing your seatbelt? So obviously, travel the world, wear your seatbelt, be cautious but that doesn’t need to limit your adventure or your sense of exploration or anything.

Maneesh: But have you ever had any issues with peer pressure, for example your wife or your family, have they ever been wondering why you’re doing what you’re doing, being not supportive in any way?

Chris: I think my family’s gotten used to it over time because the not-having-a-job thing, I’m 33 now and for a while they were like what’s going on Chris, but then I think after a while they got used to it. The travel stuff, when we lived overseas for four years and I started traveling independently almost after that and then with Jolie we talked about, ok, what are we each comfortable with, the amount of time I’m away or whatever, so that’s been fine and in the beginning my dad would call Jolie and she would say, oh Chris is in Vietnam and he’s like, what is he doing in Vietnam? Oh my gosh, and this is 5 years ago now, and now it’s like I get email from him and he was like, I don’t know what continent you’re on but I hope everything’s going ok so I think your family tends to get used to things, there were times, I think they get mostly afraid that you’re going to be a different person. They’re afraid you’re not going to come back to them, you’re not going to want to be involved in their life or whatever but then you go away and then you have this adventure and you come back and you’re like hey, everything’s cool, I think they get used to it.

Maneesh: I get this situation lot with my Indian parents it was like, I don’t know why, what I have done wrong as a mother.

Chris: That’s funny.

Maneesh: You know that Paul [inaudible 37:46] down the the street is now working in the same building as his dad and it’s good to know that some children still love their parents I’m like..

Chris: I think for me, it gets a little bit like that too, [inaudible 37:54]he’s built this very successful business so..

Maneesh: Now that he’s on tv, she’s like, finally you’re successful..

Chris: Right. Maybe you’ll become a doctor and she’ll be really, really happy.

Maneesh: I know that’s the funniest thing Indian parents, at least you don’t have that situation to deal with.

Chris: No, I don’t have that problem, no.

Maneesh: But yeah, so what’s next for you then like, once you finish the countries? I think I remember your wrote a post about this.

Chris: I’ve just started to think about that. And to be perfectly honest, it frightens me a little bit. Not frightened that too strong of a word but it worries me because I don’t really know. The traveling is only one part of what I do, I want to keep writing books, I’m going to continue doing stuff for my community, I love that. I want to keep doing meet-ups everywhere, blah blah blah, but it’s true that the Travel Quest has been a big part of my whole identity and this project and all that and so it was actually a year or two ago when Jolie started asking me, she’s like, hey I want you to be thinking about what’s coming up next and I was like, oh I’ve got plenty of time and just a couple of months ago I was in Seoul , have you traveled in Seoul?

Maneesh: No, not yet.

Chris: Seoul for me was ok I don’t hate it, I don’t’ love it but when I was there last time, I started feeling sad, I was like, I don’t even have this feeling of close connection her e, but I realized I’m sad because I’m not going to be always doing this. I’m going to be doing something different so I don’t really know what’s next so I mean I’m going to be doing all this stuff and I feel I need to get some kind of a big quest or something to follow this one, I don’t know.

Maneesh: Yeah, I remember the big difference in what I had, before I had [inaudible 39:16] income started to come, before it was easy, it’s just like do whatever you needed to make money to survive and live. Now that you have enough income, like crap, what’s next?

Chris: Yeah, what do you do, right, exactly. So it’s very easy to focus on the things that are right in front of you, if that’s taken away then you have a problem of like, oh ok, my life. We’ll see.

Maneesh: Exactly. I do want to ask you about videoing your blog because you did video posts way back when and then you kind of stopped.

Chris: Yeah, because I suck at it basically so that’s why I stopped.

Maneesh: But did you find that viewers liked it or didn’t like it?

Chris: I felt that they liked it, I felt like I probably should’ve stucked with it and I think that’s something that I should probably get back to at some point.

Maneesh: Ok.

Chris: I mean, I do want to be a writer, I actually like writing, I don’t see writing as a means to an end. I like books, I like the blog and like the meetings, I feel that it is my y medium but for sure I think it’s good to mix it up, certainly.

Maneesh: Have you ever been interested in doing something besides writing, your blog would help promote something on tv or movies or maybe any kind of thing that your blog will take you towards?

Chris: You know, I’m up for anything but I feel I got a full plate with the blog and the books and the summit and everything but I’m always up for anything.

Maneesh: Cool. Well, Chris this has been a super interesting conversation, I’ve learned a ton from you. You guys should check out Chris’ stuff at×5. Interesting..

Chris: Yeah long story, don’t do that when you start a blog.

Maneesh: Yeah and oh, I do want to know a little bit , do you recommend going with chris guillabeau .com or would you have done art of non-conformity if you could go back to the past?

Chris: Well you know, having a name like Guillebeau is difficult. When I I met Seth Gordon, I said “Hey Seth I really respect your work. Can you give me some advice, like what’s one thing that I should do differently?” And the first thing he said was, “It’s too bad you can’t change your name.” And I said, “Ok give me something else because that’s done” so it depends on your name, right?

Maneesh: Yeah.

Chris: I going to have the art of nonconformity .com, it redirects. If I could do it over I might have done it differently but then it doesn’t really matter at this point, I mean you do something, you make a decision and then you live with it so it’s fine.

Maneesh: Yeah, i’ts because of you that I have

Chris: Maneesh is good though, that’s better than Guillabeau.

Maneesh: Definitely. Well thanks a lot Chris, really good to meet you again.

Chris: Dude, thank you so much, man.

Maneesh: Yeah, we’ll keep in touch and we’ll hopefully see all you guys at the World Domination Summit this June?

Chris: July.

Maneesh: This July, what are the dates?

Chris: July 6 through 8, 2012.

Maneesh: Perfect. Thanks guys, take it easy. Ciao.

Don’t forget to subscribe to this show on iTunes.


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A Summary Of This Episode

0:49 – Meet Chris!
2:28 – Traveling to every country in the world
3:26 – Most difficult traveling experience
5:09 – Favorite country
8:02 – Frequent flyer miles
10:07 – Travel Hacking Cartel
12:18 – Best Airlines
13:51 – Chris’s blog’s traffic explosion
15:36 – Most successful product
18:06 – The World Domination Summit
21:09 – Advice for getting started
23:50 – Email culture
27:09 – The biggest subscription triggers
29:35 – Time management
31:02 – You will improve
34:18 – Crazy traveling experiences
36:15 – Don’t be afraid to travel, just wear your seatbelt
39:27 – Video updates vs. writing


Mads Phikamphon April 23, 2012 at 2:05 am

How come you both care so much about Norway?


Tom March 17, 2012 at 2:54 am

Great video Maneesh, finding great frequent flyer mile incentives in the uk can be a bit tricky. I hope someone posts a gem of a deal like the ones you guys have over in the US.



Inhak March 13, 2012 at 10:42 pm

Hi Maneesh, could you tell me other 4 most influential bloggers? I enjoy reading writings from you, Tim Ferriss, Sean Ogle, and Colin Wright.


Li February 28, 2012 at 10:40 pm

interesting how Chris started off with a smaller goal of 100 countries, and then amped it up to 192 countries AND set a 5 year deadline. I don’t think most people would have the discipline to do that.


maneesh February 29, 2012 at 6:09 am

Traveling is a drug—once you start, you won’t stop.


Michelle February 28, 2012 at 8:27 pm

Really really liked this one. Good stuff, Maneesh. Haha definitely going to make it a point to get to Norway.


dan February 28, 2012 at 2:48 pm

Really enjoyed it. I’ve been trying to build up my miles and I now I realize I’m a complete amateur.


maneesh February 28, 2012 at 2:50 pm

Thanks man! Everyone has to start somewhere 🙂


Dilanka February 27, 2012 at 7:06 pm

Good stuff Chris & Maneesh. Loved the interview. Good to see you back.



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