A ‘Digital Nomad’ is someone who works from their laptop and chooses to travel for fun, and/or because the cost of living is much cheaper in other countries. This way, they bootstrap more money into their online business while having an exotic lifestyle.

It all started in 2014 when Riley and his business partner Parker, came to Chiang Mai, Thailand, to an eCommerce conference. It was around this time, they decided to go deep into Amazon selling and build a business. 

After all, that was the dream “to be able to travel the world and be a digital nomad”. And after you start making consistent money online… why go back? 

Riley spent 5.5 years traveling south-east Asia, from Chiang Mai, to Bangkok, to Bali to Saigon, Vietnam. With a dream to travel the world, his little trip to Asia is only the beginning. 

Starting a nomadic lifestyle 

One of the worst situations Riley ever encountered was at the beginning of his new life; Riley and Parker almost ran out of money. They were so close to being broke and having to move back home. Which meant going back to ‘real jobs’, saving up money to build their dream life and business (again). 

In 2015, Riley’s first Amazon private label product (a $2000 investment) was canceled by the supplier. The entire factory was shut down due to a patent issue. Some American company came in and shut down all the companies that were making this specific type of product. Even though Riley’s was different, they had added some specific physical features, the whole operation came to a halt. 

They eventually got 80% of the $2,000 back. But they faced an even bigger problem, with almost no money and rent due soon, what were they going to do? 

It was during January/February 2015 and Chinese New Year was around the corner. They had to pull the trigger on something to flip the money they had on hand. So Riley and Parker invested all they had into one product (without taking any samples). 

And fortunately that gamble “caught fire” and started to bring a profit of $100 a day, within a month of its launching. Later on, they ended up making a 2.0 version of the product, which was even better and that product is still selling today, making over $2,000 profit a month, 5 years later. 

Like any business, it takes a combination of a good idea, execution, strategy, and a little bit of luck in there... And a little hail mary faith.

Riley Bennet

The Eventuality Mindset – An Entrepreneur’s Right Of Passage 

What Riley has seen when out in the world, talking to so many solopreneurs and entrepreneurs, is that you have to try many different things before you find that one thing that works. Especially with Amazon Riley always tells people “if everything goes according to your timeline …. somethings wrong, 100%.”

It’s normal for there to be a huge roadblock, like your account gets suspended or flagged for “Being Poisonous” when your brand has nothing to do with anything poisonous. It’s always going to be these unexpected things. If you’re going to be an entrepreneur and go independent “just pencil in the unexpected” into your timeline.  

With life, Riley agrees that a lot of things are completely random; sometimes you get lucky and things are relatively smooth, and sometimes obstacles keep hitting you over and over again. But in the end, it’s the resilience to keep trying that sets apart those who are successful from those who aren’t.

It’s not a matter of IF I’m success and breakthrough but WHEN. 

Riley Bennet

In business, there’s a common saying which states that “only 5% of what you make gets 90% of the result” – The 90:5:5 Principle. You have to keep shooting your shot until something finally sticks. Looking back, Riley always had the “eventuality” mindset, without even knowing it. That’s what helped him persevere to achieve the success of digital nomadic life. 

Building a Global YouTube Channel 

Riley’s Youtube journey and motivation 

Riley has always been a creative person, even in middle school. With an MP3 player, he would record things at school, go onto GarageBand (a line digital audio workstations that allow users to create music or podcasts). And splice together different pieces of audio and make these little mixtapes – he would record fights arguments, funny little skits, etc. It was like a comedy mixtape, that he would hand out the CDs, selling them for $5 each. 

He’s always been a person that documents, creates, and records. So when he came out to Chiang Mai, he was doing daily Snapchat vlogs to document his new life. Soon he was labeled “the guy living in Thailand”, as his following gradually increased. 

Later that year, when Riley came back home for his yearly visit, he realized that he’d been documenting so many memories on his phone. But what he really should have been doing is documenting them all in HD, so he ordered a vlog camera for $600. 

That Camera changed his life. When he returned to Asia he started documenting via vlogs. With one edit per week, his digital nomad life in Saigon started attracting a healthy following (now totaling to above 54.6K subscribers). 

He was legitimately interested in the culture, street food, and the digital nomad lifestyle. It was the first year of living his dream life after all. Motivation came from just documenting his memories as something to look back at in the future and be like “THAT was fun.” 

As quoted by Tim Ferris ‘I was scratching my own itch’

Riley Bennet

Rileys YouTube Inspiration

From his teenagehood, Riley was a huge fan of travel vloggers like CaseyNeistat, one one of the biggest vloggers today (12.1M subscriber). Just the way that he films, edits and produces content as a creative person; encouraged Riley to try and emulate Casey’s content in his own traveling adventures. 

A few other travel vloggers that influenced Riley’s nomad travel vlogs: 

• PassportHeavy – Riley has been following the channel for over 7year now. 
• Louis Cole, or FunForLouis, is a daily travel blogger, with a high record of vlogging for 900 days in a row. Riley used to follow him and his adventures while he constantly traveled the world. 

After about a year of launching his travel vlog, Riley began receiving questions from his viewers: How are you doing this? How are you traveling constantly?  

He’d constantly reply with the response, “I sell on amazon” or “I have a private labeling thing.” Soon those responses led to new questions. So he wrote this an entire blog post on his website – How we make money while traveling. 

Following that, his viewers started asking for mentorship – “can I buy your course”. That led to the decision of Riley and Peter making their very own Private label course in 2016. This step eventually branched out to interviewing other digital nomads on how they make money online and their different business models. 

With YouTube, Riley has always taken a personal direction, he had no intention to grow it into a brand. But while addressing many of his viewers’ requests, it evolved into a “one-stop-shop” for anybody who wants to know about living a digital nomad life.

To those who want to start a YouTube Channel 

“Create the content you are interested in”, that has been the big takeaway from his YouTube Channel. Livin That Life is Riley’s interest in video format. In the beginning, it was scratching an itch, so he did not go into YouTube thinking of it as a brand, it was just “put out content that you’d genuinely interested in and if you’re interested in it other people will be too.” 

Like any business, there’s no one set way to make a YouTube channel. There’s the way of Riley: Content that you, yourself, would like. And there’s the way of business:  A scheduled a content plan, along with a funding plan. 

The path you choose with your channel is entirely your own. But Riley advises to put up real content and if your audience is asking for something then just do it.  

Stress Management 

Tim Ferris’s 4-hour workweek 

Riley has been using Tim’s 4 hour work week, looking at everything as situations that are positively stressful and exciting. Being an entrepreneur and building a brand tends to be quite stressful. For example, the current pandemic we face, where sales are down by 50%, is an exciting stressful time, like everything in life. 

However, it’s important to remember it’s always “mind over matter”. You can either look at it as “poor me”, “this is a horrible situation. I’m gonna be in a horrible mood”. Or you can look at it as “here’s a huge challenge, that going to help me to be more. Provide more products or services, to create different streams of income to balance it out.” 

When a roadblock or an obstacle comes your way, your mind should go: How can we capitalize on this situation and flip it and come out better than before? It’s how you look at the situation, your mindset that makes a difference between your success or your failure. 

The challenges and roadblocks are what we signed up when we decided to become an entrepreneur. Reiley believes that if you really wanna be an entrepreneur, it’s important to be excited when the roller coaster goes down, after all, “we signed up for these challenges.”  

The First Step to Become a Digital Nomad 

What worked for Riley was buying a ticket, 6 months in advance, to a conference in South Asia, in 2014. That put it on the calendar, that that’s when his life was going to start. 

You can do the same, there’s a nomad summit every January in Chiang Mai, Thailand,  another in Bali every June.  

“Look at the calendar, buy that ticket, put your money where your mouth is, cause and that gives you an opportunity to meet 100 other like-minded people instantly.” That first step will help you build the path forward. 

It feels so much more of a reality and possibility to meet and see people who are “Livin That Life.”

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Connect With Riley: 

• Podcast: Livin That Life – Digital Nomad Podcast
• Blog – Livin That Life
• Instagram – livinthatlifetv

Alright, guys, that’s it for now!

Now we’d like to hear from you… What, from our talk stuck with you?

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