The Man Who Seems to Have it All

Travel, money, internet fame—does Nomadic Matt have it all? Matt Kepnes opens up on travel blogging, dealing with bad press, and whether or not he has it all…

Matt Kepnes’ story is fascinating. If you don’t yet know who he is, I’ll give you a brief introduction:

After finishing his MBA, Matt decided to spend some time seeing the world. Eighteen months later, after returning home to Boston, Matt found himself uninspired at the prospect of returning to his office job. Travel, or working in a nondescript office lit by flickering fluorescent lights and decorated with condescending inspirational posters of kittens overcoming challenge? Hmm. That’s a tough one.

Matt picked travel, and he started a blog to get into travel writing.

This was back in 2008, when dinosaurs roamed the internet and only a tiny number of bloggers had predicted that it would one day become possible to earn a living from this obscure hobby.

Matt was one of them.

Flash forward to 2013: Matt is now earning six figures from his self-made career, while thousands of other digital nomads are working overtime, hoping to mimic his success. While his ex-MBA-classmates sit in cubes and answer to The Man, Nomadic Matt is answering to nobody as he jets off to exotic destinations to roll around on Penthouse waterbeds blanketed with $100 bills.

(Okay, maybe I imagined that last part. I think he’s more likely to be found in cheap hostels, writing up budget-savvy travel advice for his massive readership of 200K per month.)

On top of this, Matt has just become a Penguin-published author with his book, How to Travel the World on $50 a Day.

It seems that this man has it all.

But is that the case? I harassed him over email to find out.

Okay, so you finish your M.B.A., but instead of getting a steady job, you take off traveling. Permanently. Your parents and friends must have thought you were throwing away your life? What did your MBA peers think of your plan? How did people react?

I didn’t know anyone in my program. It was a part time program. My parents didn’t want me to leave and tried to talk me out of it. My dad kept showing me job openings. Eventually, they sort of dropped the subject in hopes I would change my mind. I didn’t. My friends didn’t really react much. They were mostly like “oh that’s cool.” … I don’t really remember anyone trying to talk me out of it.

I talk a lot about naysayers on my blog (or ‘assholes,’ as I call them.) Did you get many naysayers? If so, how did you deal with that?

You develop a thick skin. There will always be trolls on the Internet. In some cases, I’ll take their hate and turn it into a good blog post that inspires others to ignore the haters. In many cases, I’ll reply back with a polite but backhanded attack. For the most part, I just ignore it. They are just a fact of life.

Can your achievements be repeated given that when you started, there was only about 10 people doing the same thing, and now there are several thousand?

Yes, they can. To say they can’t is to say that no one can ever open a new restaurant again because there are already so many that exist. If you have a good idea, you can make it work. You need a unique story or angle that hasn’t been done to death. Stand out from the crowd and it doesn’t matter how big the crowd is. People will notice you.

Can you take us though the early stages of inventing your career? When did you know you had something? Did you have a strong vision, or did it morph and take form once you began?

I’ve never really heard that I invented my career before. I like that phrasing. In the beginning, I had no idea what I was doing – I had no plan, no vision, no idea. I was just kind of rolling with what was given to me. I just reacted to events. It didn’t really morph into something with a plan until late 2009, early 2010. It was then I realized I could do something more with the site and started to develop a strategy on how to succeed.

Did you have moments of self-doubt?

All the time. Still do. I think every successful person does.

Did any other bloggers, writers, or entrepreneurs inspire you? Do you have mentors?

Lots. Folks like Tim Ferriss, Ramit Sethi, Chris Guillebeau among others all inspired me to get better at what I do. I get a lot of good feedback from the blogging community – Ramit, Chris, plus folks like Derek Halpern, Corbett Barr, among others. These guys are very good at what they do and very helpful in giving advice. We bat a lot of ideas around.

What’s the worst criticism you’ve ever received? How did you cope with it?

Ramit Sethi from I’ll teach you to be rich just laced into me one day over drinks about my lack of a plan, strategy, and more marketing. It was like 45 minutes of why I suck. It was the best experience ever. I learned a lot and was able to rethink how I planned everything. Too many times travel bloggers take criticism personally when really, most of the time it’s helpful advice. If someone is taking the time to tell you how to get better, even if it’s not in the nicest of tones, listen. They really do care.

You got a bunch of bad press from your piece about Vietnam. How did you feel about that? Do you think that exposure ultimately benefited you?

The world is a giant place and you can’t expect to like 100% of it. I didn’t like Vietnam. I had a bad trip there. It happens. My point was that with such a big world, why would I go back to a place I felt mistreated in when there is so many new places to see? With those kind of articles, people read what they want to read and for the naysayers, they read “I hate Vietnamese people.” When someone says “I didn’t like France” I don’t think “You racist French hater!”

In the end, I got a lot of buzz out of it and you know what they say, all press is good press.

What do you consider to be your greatest accomplishment?

Creating a website people actual read, respect, and use. It’s amazing knowing that people listen. Sometimes it’s hard to believe. You think to yourself “Really? You read my site?? You liked it?” It’s humbling.

Your book How to Travel the World on $50 a Day was originally a successful self-published e-book, but you decided to sell the rights to Penguin. Self-publishing is said to be the future of publishing, but your actions don’t align with this rumor. Take us through your decision to self-publish. 

Self-publishing is great. You get 100% of the profits and if you are a big name or are selling your books for 99 cents, you can be pretty successful at it. But eventually you hit a wall and since I wasn’t in the Amazon store, there was a limit to what I could do. A traditional publisher gives you access to media you can only dream about and a print book gives you credibility that can’t come with self-publishing and not every one wants to buy an ebook. Some people still like paper. I don’t regret the decision at all.

Do you have any thoughts on the future of publishing?

Not much. I don’t really think about it but if I had to think about it I would say more first time authors will come from blogs and ebooks are only going to get bigger.

Do you have any advice for the bloggers out there who wish to get a publishing deal?

Torre, you’ll likely agree that having a built-in audience is key. Publishers know that no matter what, you’re going to sell some books for them and there will be built-in word of mouth. If you want to pitch a deal, build up an audience. You’ll have an easier time convincing a publisher to take a chance on you.

A lot of people idealize the traveler’s lifestyle. From the outside, it could seem like you have it all. Is your life as glamorous as it seems? Is there anything you idealize? Is the grass greener elsewhere for you?

The grass is always greener somewhere. I wouldn’t say my life is glamorous. I wish I was around in one place more so I could have steady friendships and relationships, as well as get to a gym more. Even with moving to NYC, I’m only there about ½ the month. Yes, I get to travel a lot but a lot of the times I’m working. I’m not just hanging out at a bar relaxing.

Do you have any regrets? 

I never studied abroad. I was young and naïve and that was a mistake. More recently, I left a girl in Asia. I should have stayed. Leaving effectively ended our relationship. That’s a big regret.

If you could give one piece of advice to the whippersnapper who started nomadicmatt.com in 2008, what would it be?

Put a giant subscribe box on the front of your website for everyone to see so people actually follow your site. I lost thousands of readers by making it hard to find the button to subscribe to my site.

What happens when you’re done with being nomadic, Matt?

The rapture.

And lastly, because it’s the subject of my blog, what’s your greatest fear?

Heights. I hate heights. I’m always afraid I’m going to fall off something or come crashing down and hit the earth. God put us on the ground because our feet are supposed to be planted on the earth – not high in the sky! So yes, in case you were wondering, I am also a really nervous flier.

If you have any more questions for Matt, ask him in the comment section below. 

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Matt has turned his last seven years of backpacking and blogging into a resource packed with tips, called How to Travel the World on $50 a Day. According to Matt, you don’t have to be disgustingly rich to see the world.

If you’re plotting out your own grand adventure on a shoestring budget, buy it for yourself, or gift it to an intrepid pal here.

Torre DeRoche

Torre DeRoche is the author of two travel memoirs, Love with a Chance of Drowning (2013) and The Worrier’s Guide to the End of the World (due out September 2017). She has written for The Atlantic, The Guardian Travel, The Sydney Morning Herald, Emirates, and two Lonely Planet anthologies.