Run a startup, travel the world, defy convention: Q&A with Chris Guillebeau

[Here’s a Q&A I originally posted on Memeburn]

Building a startup on-the-go while you travel the world may seem unlikely. The status quo would have us believe it borders on the impossible. Thing is, Chris Guillebeau has done just that. Oh and he also writes books and evangelically spreads his unconventional ideas on entrepreneurship and startup communities.

The word “unconventional” is actually a pretty accurate description of Guillebeau. The American entrepreneur reckons you can build a startup for less than US$100 and even wrote a book explaining how. His popular blog, The Art of Non-Conformity, focuses on travel and personal development topics and meshes with his personal mission of helping people live life by their own rules using a “non-conformist” lifestyle.

We caught up with him during his travels and talked about his insights on building a startup, how he uses technology and where he thinks the next “big thing” in tech will come from.

MB: Building a startup while office-bound is hard enough, how do you build both a startup and a community as you travel the world?

CG: I’ve never separated travel from my work. For 10 years I’ve been actively travelling to 20+ countries a year, and for the same time I’ve been building online projects. I think it helps that I enjoy what I do. I don’t feel like I’m struggling because I’m motivated to keep working away.

MB: You are constantly building ‘Unconventional Products For World Domination’ and send blog updates, sometimes in airports, from the world. What are the top three things that go into building a new product?


  1. Understand what people really want. (It’s not always what they say they want.)
  2. Create a highly compelling offer. The offer is at least as important than the product or service itself, and most people save it for last. Don’t save it; design your whole structure around the offer.
  3. Ensure good follow-up and over-deliver whenever possible. Your customers will stay with you for life if you keep helping them.

MB: You recently released a book to help writers get their books published. What doesn’t the world know about self-publishing?

CG: The world doesn’t know that the break between self-publishing and traditional publishing is overstated. You can self-publish and traditionally publish. For me, I love both options.

MB: Can cheap, democratised technology overcome barriers in entrepreneurship?

CG: Sure, and we see that especially in Africa. In the future I think we’ll have more and more African entrepreneurs accessing a global marketplace instead of just buying and selling within Africa.

MB: In 2011, you embarked on your ‘Unconventional Book Tour’ which involved your blog readers. What three lessons can you share from that tour and rallying your audience as part of a cause for common interest?

CG: The book tour is continuing now and I hope to visit South Africa at some point. (I’ve been many times as a traveller, but never as an author on tour). Among other things, I learned that meeting readers is an excellent source of inspiration. After a meetup, I go away thinking about the people I heard from, many of whom are living remarkable lives of their own. It helps me to serve them better when I know who they are.

MB: What’s the most challenging tech situation you’ve ever found yourself in?

CG: I’m constantly searching for Wi-Fi access everywhere I go. Surprisingly, some poor countries have better access than some rich countries. It just depends on the country and even the specific area.

MB: What’s your latest book, The $100 Startup about?

CG: Two things. First, it’s the story of 70 “unexpected entrepreneurs” from all over the world who started businesses by using small amounts of money and the skills they already had. Second, it’s a blueprint for readers to do the same. The goal is to inspire a revolution of freedom, as more and more people choose self-employment over traditional jobs.

MB: What has changed for you since you built your first startup, which inspired you to write a book to educate entrepreneurs?

CG: I’ve learned to become more strategic. In the early days, I was primarily concerned with getting by and paying the bills. This was better than working a regular job, of course, but I wasn’t really building anything of real value. These days I feel focused on a clear goal, so it’s a lot easier.

MB: Where do you think the next big tech innovator will come from?

CG: I’m less interested in innovation and more interested in usefulness. Most of us aren’t going to make the next iPhone, but we can all make something that improves people’s lives. To me, that’s what entrepreneurship is all about.

The Kindle version of The $100 Startup is already available for sale.


Start And Build A Community – Q & A with Chris Guillebeau

Photo by: Chris Guillebeau

Do you want to change the world, but struggle to differentiate yourself enough?

Organizing a community lets people know whether they belong there or not. Whether it’s for them or not. With the right people, you are able to focus instead of wasting your time and energy on everybody else – who is not meant to be part of that community.

Author, world traveler and change agent – Chris Guillebeau is our first guest this month. He took a moment from planning his book tour – to let me know what inspires him and how he built his global community.

Q & A with Chris Guillebeau

Q : What is the Art Of Non-Conformity?

Chris : AONC is a blog, a book, a business, and a community—mostly the latter. I started the project in 2008 as a way to spread unconventional ideas and help people find a way to achieve big goals.

Q : While developing products and travelling the world, how do you maintain focus on building your business and “making a living”?

Chris : I don’t really focus on “making a living.” I do focus on work, but most of my work is free for everyone. I use a 90/10 model where 90% of my writing and events are free and 10% are paid.

Q : How would you define your product?

Chris : Let’s look at the overall goal: to help people live unconventional, remarkable lives. How that works varies. I have the blog and other hubs where I connect with readers. I have the Unconventional Guides business that consists of things like the Empire Building Kit and the Frequent Flyer Master guide.

Overall, I hope that all of these help people in a different ways, but with the same goal of creating individual freedom and inspiring action.

Q : Why did you decide on creating your own niche community?

Chris : I felt like I had helped a lot of people on a one-on-one basis over the years, but I had no broader platform. I turned 30 years old and in the process realized that I wanted to be a writer. So I started the site and went from there.

Q: Most entrepreneurs starting out want to satisfy everyone. We want to sell everything to everyone. How did you identify the people you wanted to organize into a community?

Chris : Correct, and that’s a big mistake. In my case I learned to target people on a psychographic basis as opposed to a demographic basis. I have readers of all ages, all backgrounds, from all over the world. What they have in common is a desire to change the world.

It’s interesting, because in the beginning when I connected with a literary agent and he was pitching my project to traditional publishers, some of them said, “People who want to change the world are not a target market” – which makes sense in a traditional, business-oriented context. But over time I’ve become more and more convinced that “people who want to change the world” is indeed my perfect audience. It’s also an audience that is motivated to take action, which is always good.

Q : What would you attribute as the single most important aspect of creating your community?

Chris : Consistency. A lot of bloggers start out strong and then fade off into the blogging sunset. If you can just keep going and building a strong platform, you end up outlasting people and it gets easier over time.

Q : In your manifesto: A Brief Guide To World Domination – you clearly state I should warn you now that this report is not for everyone. I have also realized that from your blog and the rest of your products. Doesn’t that separation of your audience from everyone else limit how much you can make and who you can reach?

Chris : No, for reasons you alluded to earlier—it’s always a mistake to target everyone. Better to be clear what you’re about and who your work is for. This also makes it much easier to build trust and authority among the group with which you choose to identify.

Q : Most of your content is free, while traditional business principle tells us to “sell” “sell” sell”. Where do you make your money?

Chris : I still make money, but the greater goal is influence. The money comes from and my book publisher—though much more of it comes from my own projects than the publishing arrangement. (I’m still a fan of writing books, but it’s true that there’s not much money in it.)

Q : You have become quite – in fact very influential online and off. What does it take to build such influence and become this outstanding?

Chris : Well, I’m not sure I’m outstanding. When I think of people who are outstanding, I don’t think of bloggers—I think of people who have truly sacrificed, like the aid workers I used to work with before I embraced the soft life as a world-traveling blogger.

But in terms of influence, it takes working towards something day-in, day-out for an extended period of time, often without much reward or attention in the beginning. I also decided I wanted to create real relationships with readers as much as possible. I answer all the emails and don’t outsource anything. I meet with readers wherever I go. I do blog interviews for sites that have 10 readers and podcast interviews for shows that are still getting off the ground.

Over time, I think those things have a real impact.

Q : Most entrepreneurs want to be different, but fear the unknown – the unexplored. How does one overcome that hurdle of distinguishing themselves and carving a niche?

Chris : Yes, I agree that fear is a very real obstacle. I think the key to overcoming it is:

a. acknowledging your fears, without trying to be “fearless” or pretend that fear doesn’t exist, and

b. not allow your fears to make your decisions for you.

Instead, ask yourself – what would I do if I wasn’t afraid, or if there were no limits? Then find a way to get closer to that, even if it’s a series of small steps at first.

Q : You are doing the Unconventional Book Tour soon, what inspired it?

Chris : These days a lot of people are saying that books are dead and book tours are ineffective. I like the idea of proving those ideas wrong—my contention is that people have been doing book promotion the wrong way, but that doesn’t mean that books are dead.

And I also like big goals, so when I decided to establish my own tour, I thought… why not make it as epic as possible? So I picked all 50 states instead of just the major cities. Then I added all 10 provinces in Canada, because I didn’t want to leave them out. Then I added an extra city in California, an extra city in Texas, Washington, D.C. – and came up with a 63-city self-funded, collectively-organized book tour. I hope to take it worldwide next year, but one thing at a time. 🙂

Q : As an entrepreneur and agent of change, what is the one most difficult challenge for you?

Chris: The fear and insecurity we mentioned earlier are continual challenges. I also have a hard time asking for help – I have a lot of people willing to help with things, but I don’t always know what to ask them to do.


While Chris is on the go and launching his new book, he also Tweets here and blogs at AONC. I recommend you follow him.