Digital Nomad Interview with Mike from Hobo With a Laptop

When I was living in Chiang Mai, Thailand I had the opportunity to meet with digital nomads Mike and his wife Oshin, from Hobo With A Laptop. I loved the site name and wanted to learn more, and lucky for me, Mike agreed to an interview.

He tells us how he feels about being called a digital nomad, staying healthy while being location-independent, and how he sustains a profitable business on the road.

After the interview check out his website here.

Mike and Oshin, the creators of hobo with a laptop

Thanks for doing this Mike! Let’s get right into it. How did the idea come about to start Hobo with a Laptop and why that name?

Mike: Initially, Hobo with a Laptop was a placeholder for ideas I thought might come to me down the road. I initially registered it on impulse, just in case I would ever create a blog about full-time travel, or alternative living like #vanlife or tiny house living.

Truth be told, I never want to be “that digital nomad” guy –I’ve got a lot of suit-wearing peers back home who’d skewer me for a perceived self-demotion, and more to offer than just being a guy who tells other people how to be that guy, so they can tell other people how to be that guy, and so it goes. It’s an echo chamber I didn’t want to be a part of.

Digital nomad blogs are often so much fluff, am I right? And don’t get me started on travel blogs –” We spent three hours in Tuscany on a layover! Here are the top 25 places to buy a hot dog”. Ever met a life coach under 20 years of age? I have, and I just don’t understand it.

After a couple of attempts at starting Hobo with a Laptop, I shelved it. Pulled it out when I published Digital Nomad Escape Plan to promote the book when it launched, then shelved it again.

hobo_laptop_logo_2017One of the first logos for Hobo with a Laptop

Years later, I started Copyrise; an influencer marketing-focused content production company –think SEO ‘content mill’ but with a little more class and a higher degree of quality, with a focus on the travel and tourism industry.

I was surrounded by successful travel bloggers for years, so I thought I’d leverage those relationships to everyone’s benefit. Hook them up with sponsors, free hotel stays, free gear, or fine dining for a do-follow backlink or an unbiased review (if that’s possible when everyone’s kissing your ass).

A few of those influencers got paid more than my wife and I did, and we did all the leg work. It sucked.

So, we did what any hot-blooded internet marketer with 2+ decades of experience would do –we reverse-engineered the shit out of everyone.

We learned from our friends in the industry, and with their help and support, Hobo became what it is today. We also took a particular interest in answering questions other bloggers charge to answer.

And then, of course, we added our spin on it. We did our best not to imitate. Instead of selling the digital nomad or travel blogger lifestyle, we showed people how to get started for free.

Hobo with a laptop gave as much value as we could without blowing any smoke up anywhere the sun didn’t shine. We avoided using words like “crushing it”, and “it’s easy”, and adding the word “lifestyle” to our products.

We rebooted sometime around May 2017 and were cash-positive within 2-3 months. By August Hobo with a Laptop was generating more income than Copyrise; we were getting more inquiries from new clients, and new revenue streams with affiliate links, and we made so many new friends in the industry, that it was worth it. No more business development? Yes, please!

space-logo.

I’ve shuttered Copyrise for now, unsure what to do with it. I like the logo so I want to revive it again in 2019 in some shape or form. But for now, we’re going to ride the Hobo train.

Now Hobo with a Laptop is mature, somewhat. It’s a resource to help anyone quit their job, make money online, and trade their higher cost of living for something more reasonable in today’s economic climate, while still making decent money.

Down the line, we’re going to circle back and put more focus on travel posts. After we finally brain-dump all we know into the best how-to content we can produce.

And the title? That came out of a bong in St. John, New Brunswick. There’s a Canadian film called Hobo with a Shotgun starring the original bad guy from the first Bladerunner. Hobo with a Shotgun was gloriously terrible. Grindhouse fans, take note!

Where was the first place you lived outside of Canada? How did you decide to go there?

I’ve been a nomad to some degree in my home country of Canada since I was 18 and I’m 36 currently. I’d moved around from West to East.

However, I only saw my first palm tree in the Spring of 2012 or 2013. By Autumn, I was on a flight to Thailand.

I took a trip to Florida with my then girlfriend and begged her —can we just not board our flight home? Can we do that?

Well, the answer was no. So we went home to Canada and started making plans for the big leap. In the end, she bought a car and I bought a plane ticket and the rest is history.

You have a bunch of posts about Chiang Mai, how much time have you spent there?

A few years, at least. We just got back from another visit (where we met you, you awesome human!).

Chiang Mai wasn’t my first destination, but it was the first place I met a sea of like-minded people.

I crashed and burned dozens of times. A bank card got eaten by a bank machine at a border town and took months to replace. I went through two laptops. I had to make friends I could trust, and fast, to turn my PayPal earnings into baht.

Earnings I made using a loaner computer at the TCDC or using Google Docs on my phone. As a copywriter, I wrote dozens of articles for an SEO company on my old iPhone 3GS to save up enough to buy a laptop. The horror.

Chiang Mai Hobo

Chiang Mai regimented me in ways I didn’t expect. It distilled me, made me stronger, better, faster, and, uh, kinda’ drunk all the time. (It takes a few years to get over the fact a giant beer is a buck fifty).

The city and the people who ride on its back got me through.

I’ve helped people start businesses, and I’ve had friends slap me around and help me focus on just one idea. It’s really hard to settle on a single idea in Chiang Mai because you’re inspired by every person you meet and what they’re doing.

I love your infographic on how to save money in Chiang Mai like it’s not cheap enough! How did you find out that you can sleep in a temple? Did you have to do that?!

I was seeing a girl from LA who was going through an Eat Pray Love phase and she told me about it. I thought it was brilliant.

Never did it, but she did –of course, not out of financial obligation. She was far too smart to be caught empty-handed and as screwed up as I was.

It wasn’t easy for her though, I’ll tell you that. There are few creature comforts up there in that temple on Doi Suthep, no cell phones allowed, but they’ll feed you if you can cross your legs all day long and sleep on a board. Nerves of steel, she had.

As a digital nomad, is your blog your main source of income or do you have other projects going on?

We do have other projects. I’ve written a few book outlines I hope to turn into books one day, the first one still makes money because it’s “pay what you want” although I do encourage people to keep their money and save it for some Khao Soi.

We have other affiliate sites. I trade cryptocurrency. My lady loves helping fellow bloggers with Pinterest. We’re about to try our hand at a podcast. And we still take on clients we get from Hobo.

Financially speaking, I make a little more than I did back home. It’s nothing to boast about, but it’s a lot when you’re spending pesos in the Philippines or Baht in Chiang Mai and earning USD.

What has been the hardest struggle about living abroad and working remotely?

Getting really sick. Like ‘Am I dying?’ kind of sick. And being away from my lady for more than 3 months once. That was hell.

The money? I’ve probably lost a few years of my life and an inch off my hairline stressing over it. I’m almost entirely forehead now! To date, I’m on my fourth laptop. Not having a laptop sure is a buzzkill, but it wasn’t the worst part.

But I learned something. You cannot fail if you do not stop trying. And never lose faith in the universe, or in my case, God. He’s had my back with so many coincidences, big ones, that it just can’t be a coincidence anymore. At times, I feel like I walked into a room He just walked out of. Always one step behind Him.

I’d be eating my last bowl of rice with –and this happened twice, not once– I’d be eating that last bowl of rice, and I’d take a deep breath, and I’d use the last fifty baht I had in my pocket to buy a beer with that rice to maximize the enjoyment (and possibly the suffering and guilt that could have potentially followed).

I mean, I had no one to bail me out.

I was on my own. I’m in my thirties for crying out loud.

I couldn’t go home, there isn’t one back in Canada, my folks downsized years ago.

No one was waiting for me anywhere with open arms.

One of those times I turn around and Noah Kagan’s sitting a few tables over. Noah taco-eating Kagan! I didn’t talk to him or anything, because that’s not the miracle lol It just spices up the story. Would have been cool if he was my Bill Murray though; “Hey Mike, here’s some life advice and a taco”.

But I’d be sitting there slowly chewing almost regretting that ice-cold beer and on the verge of a good public ugly cry when a beautiful girl would walk up to me and say “I hear your name is Mike and you make websites”.

Twice, Gina!

Mike  (hobo with a laptop) and the King

In the end, both of them needed not one, but two websites. Wait. The second time it happened it was three websites. All of them are either for some resort or a tour company.

Have faith, the struggle diminishes. Thoughtfully and resourcefully act on that faith and let it guide you, and the struggle moves out of your apartment and steals your favorite sweater.

But you cannot fake faith. And when it does slap you around, and you do go hungry, well. Don’t blame God, blame yo’ own damn self. I’ve never gone hungry. I ate condiments for dinner once when I was 18, but that’s beside the point.

Gina: What advice would you give someone who wants to move abroad and work remotely?

  1. Read Hobo with a Laptop. If you’re new to the travel-forever, work remotely, digital nomad racket, I suggest you start here.
  2. Nothing is in your control. Especially in Asia or any place you don’t speak the language natively.
  3. Choose your risks wisely. And keep an eye on your health.
  4. Always try to see the best in people. If you start to get frustrated with all the things, it’s time to move on. I failed hard at that for a while. When my health took a dump, I became a keyboard Nazi and made an ass out of myself on numerous occasions. To anyone reading this who knows that side of me, please accept my apologies.
  5. Hire a virtual assistant as soon as possible, as soon as you have a plan and you’ve started exercising it. I hired my first VA when I was broke, starting out, and we doubled or tripled each other’s income in the first month we worked together. We’re married now.

I guess that about wraps it up.

Above all Gina, thanks for the great conversation when we met, and the opportunity to speak to your friends and followers. It’s people like you that make this whole thing worthwhile.

And uh, sorry for the potty mouth. 

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I hope you found some inspiration and truth in Mike’s interview. He lays it all out on the table, the good, the bad, and the realistic side of things.

I wish Mike and Oshin the best of travels!!

You can reach them through their Website and Facebook.

*All Images courtesy of Hobo With A Laptop

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Gina

Gina is the founder of Jet Set and Forget. She is a licensed tour guide and fitness professional who has traveled to over 15 countries since 2010. Gina left her position as a COO in 2023 to travel full time. She is on a mission to help people travel stress free!
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