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Ep: 187: How this digital nomad earns passive income on Amazon with Riley Bennett

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In this week’s episode, I speak with Riley Bennett who is the founder of Livin’ That Life, where he documents his journey as a digital nomad. 

He has been running a successful Amazon selling business for over 5 years while living in South East Asia and traveling the world. 

Listen on to find out how Riley has been able to share his experiences creating passive income on Amazon and knowledge to help others make their dreams into reality.

Listen Below:


Ep: 186: How this entrepreneur created a successful e-commerce biz from her passions with Monique Davis

Ep: 185: How this digital nomad creates income as a remote audio engineer with Ben Smith

Ep: 184: How this entrepreneur left a Fortune 500 to becoming a professional online marketer with Mariela De La Mora



Hey everyone! Thank you so much for being here. I am really excited about my guest today. Hey Riley, how are you? 


I’m doing great. Just chilling here in Bangkok. Living that life you know.


Sounds like a great time. So Riley, can you tell us about you and why you live an offbeat life? 


Yeah. I’ve been off the beaten path since 2015. I came out here to Thailand to an e-commerce conference and Chiang Mai in October 2014 and got into selling on Amazon at that time. It started going well and basically never went back. 


Why did you decide to go all the way to Asia to go to a conference?


Basically, we found it on YouTube. We found Johnny FD’s podcasts/ YouTube channel and he announced his putting on a conference in Chiang Mai, Thailand. And so we were like, “Oh, we want to be digital nomads so let’s go to the conference and figure it out.” 

And so we went and are still here. 


That’s hilarious. I actually just interviewed Johnny like 2 weeks ago.




It’s so crazy that you guys know each other. It’s such a small world in so many ways, right?


Yeah. I actually just hit him up yesterday and we’re doing a podcast on my podcast next week. 


That’s great. It’s really interesting how you got to where you are because of Johnny and his story is so incredible too. So that’s so fun that you guys will be able to collaborate in that sense.


Yeah. Small digital nomad world you know.


So after going to the conference, how did you actually prepare for this lifestyle? Because I’m sure it was a lot of information that you were taking in, how did you take that and actually make it into a reality? 


Well, yeah. The first step of being a digital nomad is getting your money online, having an online business. What Johnny does and what he was doing is dropshipping, high-ticket dropshipping specifically.

So we started doing that, got his course and everything, and started working on that. Worked on that for about six months before the conference, before we blasted off to Chiang Mai and wasn’t really making money yet. 

But when we got to Chiang Mai, we met a couple of guys who we’re selling on Amazon. And they’re doing really well and so we’re a bit frustrated with dropshipping, “Let’s try the Amazon thing.” And so launched a couple of products and ended up taking off.

So, the big picture, you just gotta keep chugging and follow what’s working out there. Keep working, keep trying different things, and eventually, something will catch on. 


When you were looking at dropshipping and you actually did it for six months, what were the things that didn’t work out for you and made you decide to go in a different direction?


Well, looking back, basically, we were not doing some of the most obvious things, number one: Facebook retargeting. We were doing zero Facebook retargeting which, looking back, is the stupidest thing. And number two: we weren’t doing any email remarketing. So we were not collecting emails from visitors to our site. We were not dripping emails, obviously, to them. 

And so when you’re not doing any retargeting, you’re not going to get very many sales. Looking back, it’s pretty 20/20 why it wasn’t profitable for us. 


And why did you think that it was going to work out with Amazon FBA? What made you decide to do that, instead? 


Basically, we met a couple of guys they’re actually younger than us at the time. We were like 25, they were like 21 and somewhat 19 actually. And I don’t know, they were just crushing it with Amazon and seem to be doing really well and we are kind of ready to pivot into that.

And we just decided to make the pivot and go to Amazon. 


It’s always so cool to see somebody doing it really well and sometimes you got really excited about that, too. So, how did you make Amazon work when you couldn’t do it with dropshipping? What made that really click for you and your partner? 


Well, every business model is different. One is not necessarily better than the other. It’s just as you move on in life, you get better and you learn from your mistakes. 

So we launched one product and that was not the one that took that hit and caught on and lost the next one. Learn from that product and ended up catching on. And that product is still selling five years later. So, ended up doing really well and then just kept launching products on there from then.

Not every product is going to be a home run but, like a business, you just keep launching things, learn from the previous one and try to increase your chances of success. 


Yeah. And we’re going to talk more about this with our extended interview with you, Riley, because we’re going to dig deeper into Amazon FBA and how our listeners can maybe dig into it too and start it. So that’s going to be really exciting. 

So when you finally had that moment, when you knew you were going to leave your life in the United States and move full-time to Asia and do this online business, do Amazon, do all of these different types of remote work, did you ever have a what now moment and what was that like?


A what now moment – great question No, not that comes to mind, our goal from the very beginning was to travel the world. For many of us, as Millennials and people of all ages, the dream is to travel the world.

And so through that, that’s how we found Johnny’s Travel Like A Boss. And then, it became very clear that having my business is the ticket to be able to travel whenever you want. 

So after we started making consistent income for my Amazon store, we’re not wondering “what now”, we’re just like, “Okay, finally now we can earn our living from wherever and we’re just free to live wherever.”

And we stayed based out here in Asia because that’s where the conference was. So obviously that’s where we met our initial batch of dozens and dozens of digital nomad friends at that conference. 

So we stayed in Chiang Mai and met tons of people. And then what’s the next place you go when you get bored of Chiang Mai? Go to Bangkok, meet a bunch more friends here, and then go to Bali.

So, Southeast Asia,  that’s kind of where we met our friend group. And yes, I just have been based out here continuing to add more products and try to grow our business. 


What’s happening right now with the lockdown and coronavirus is a really interesting time for everybody, obviously. But it’s even more interesting for someone like you, Riley, who is able to make money online and it doesn’t really affect you much.

And it’s so funny because, before this, a lot of people are still questioning, probably, your lifestyle. I don’t know about you but it definitely has happened to me. And now that this whole thing has happened there like, “Okay, what you’re doing is actually sustainable and it’s not that bad.” 

Do you feel like you’ve been validated somehow or there have been more people coming up to you and be like, “How do I do this? I need to be able to do this too.”?


Yeah. I would say there’s definitely a little bit of that. When Corona hit and people might have lost their job, I think it definitely kicked a lot of people in action towards starting their own business that they own. ‘Cause if you’re your boss then you can’t get fired   

So with the whole coronavirus thing, every business got affected differently. Some products that are available for purchase online, which is everything, skyrocketed because it made sense. So things that you can use in the homemade sense. Other products such as fashion and stuff took a big hit.

My particular store is iPhone accessories – most of my products are. So they took about a 40% hit but at least it was still selling. At least unlike some businesses which had to completely close. 

So, yeah. We’re still in business so we’re lucky. 


When something like this happens, like a crisis happens, and honestly, nobody knew this was going to come out right? It was just out of nowhere and then all of a sudden everybody’s in lockdown and a lot of people are in a panic, no one can really work. 

How did you really prepare for it or did you even? Because like I said, everyone was kind of blindsided.


Well, yeah. I guess there’s really no preparation for it. Just like a reaction to it and I guess there was not really much we could do other than if you’re in the e-commerce space what you can do is pivot your product lines to fit the current situation. Come out with some product that would fit people’s needs and.

Actually, we did that. I have forgotten about this: I actually made a whole new video for one of our iPhone accessories geared towards how you can use it at home. So I reached out or had my VA reach out to a bunch of the Instagram people and film clips of them using our product at home. And then I added a little video together for that. 

So yeah, we just kind of took what was happening. Try to do what you can do to make your business the best in the current situation.


Have you made any other changes with your business or maybe even a business model that will kind of protect you from something like this in the future?


With the Amazon business model, nothing has changed. We’re continuing to launch and come out with new products – same as before. But I think, overall, the big picture is diversifying your income. 

I think a lot of people are kind of going to get a kick in the butt towards going forward with diversifying your income and any entrepreneur knows that. How you create wealth is you create multiple streams of income, not just one.

So I’ve had multiple streams of income although not to the level of my liking. So I have my Amazon business which is my main income. I also have my YouTube channel/podcast, which is another side income, smaller than I would like and then, I also have my Amazon marketing agency where we launch products for other brands on Amazon. 

And so I’ve been working on those: my YouTube channel for five years and my agency for like a year and a half. But I think yeah, it’s just a wake-up call for any entrepreneur. Hey, if you don’t have a diversified stream of income, you better get on that ‘cause you never know what’s going to happen.

If something happens with China and your Amazon business gets shut off, then you have other streams of income to keep you afloat, to keep you going. And the same goes for the other businesses, you never know what’s going to happen. 

So yeah. The mission is still the same. It’s still: create multiple streams of income, build wealth, and build security through different forms of income. 

There are so many lessons that we have all learned from this whether it’s good or bad but its always great to take a look at it. What you’re doing Riley is making something bigger from this and learning a lesson from it and taking it positively.

And honestly, that’s all we can do otherwise, we’re just going to be curled up under a rock or something.


Yeah, exactly. That’s what I’m saying. All we can do with corona is just learn from it and come out the other end stronger.


Yeah. Now, what has been the biggest setback that you have encountered so far as an entrepreneur and how did you handle it?


Probably the biggest setback/challenge was just getting off the ground in the beginning. We had our dropshipping stores when we came to the conference in Chiang Mai, Thailand and weren’t making money. So we’re like, “Crap!”.  ,

We had only like 8K saved up from our corporate jobs. I did door-to-door sales, corporate sales for Comcast. So I came out and my bank account started to go down we’re like, “Oh crap! We need to flip this money to keep living out here and Chiang Mai.”

For the first product that we wanted to go for, we placed a test order with the supplier, and actually after we placed the order there was a patent issue. Some companies in America went after all the Alibaba suppliers to stop making this type of thing.

So we got a message from the supplier saying, “Sorry we took a big loss with this one. We had to cancel the order and had to destroy all the products.” And so we were like, “Oh no!” End up getting 80% of our money back but it came down to the wire,  quickly pivoted into the next thing and that product ended up taking off which saved us.

Yeah, the biggest kind of hurdle was just trying to figure out that first business model/product that was going to take off and kind of be your base to move forward. 


It’s so interesting how we see someone like you, Riley, who’s successful with their online business. You have this huge community now and we often don’t realize how many obstacles that you had to go through to get to this point. I think oftentimes you just see the great part of it. 

We see you on YouTube, on social media and we’re like, “Yeah, great. How can I get there?” Like you said, the first part is always the hardest and also motivating yourself when you’re faced with all of these different types of obstacles. 

Riley, how did you get over that? Because a lot of times it’s the fear of failure, for most people, is not a pretty thing, how did you keep going even though you failed and just kept pivoting and doing it? 


I think it’s just perspective – number one. So I would consider having a nine-to-five job for your life being a huge failure – that’s the biggest failure. The biggest failure is to not pursue your dreams and be thinking about, “What if I went for my dreams? What if I went towards starting my own business?”

Basically, you got to follow your dream in life, you only got one life. People who have that mindset don’t care how many times it’s going to take to try to follow your dreams. It’s like that’s the only point of life: follow your dreams. 

So looking back, this is all 2020. I had that mindset from the get-go. Didn’t really realize it but it’s that mindset. It’s just like if it’s going to happen, it’s just a matter of time when is going to happen.

So that’s one thing and then the other thing is my situation was very relatively easy because I was only two years out of college, didn’t have a “serious job”, didn’t have a mortgage or family or anything like that. So it was very easy for me to bounce out to Thailand and say, “Alright, let’s give this a go full-time. 

So there’s that and then the other thing is I came out with my best friend Parker at the same time. So I had a business partner from the very beginning, grew up with him my whole life and we’re like, “Yeah dude. Let’s go for this thing. Let’s make the 4-hour workweek. Let’s make that our project and let’s just do it.” 

And so we were hand in hand doing this together which made it a lot easier. When you do it alone it can be a lot scarier. So I made it just that much easier for us to do this together, make this decision together, to jump in full time, to pursue our dream of being digital nomads. Be out there and do exactly what Johnny is doing. 

It just really resonated with us as well as other digital nomads most notably Jubril Agoro of PassportHeavy was our other top two influencer. Just watching YouTube videos and just play, “Okay, if these guys can do it then why can’t we do it?” 

So that just became clear to us and yeah, went for it, kept trying, and got lucky. With everything in life, it takes a little bit of luck but you keep trying to get luckier. 


That’s why I love all of these different types of information out there whether on YouTube, blogs, or podcasts because seeing somebody actually make this work and make it sustainable is such a huge motivation for all of us.

It can happen and you’re right, if they can do it why can’t you? That’s why I love talking to somebody like you, Riley, who really made this into a lifestyle in what they can really do.

Now, let’s go back to when you talked about your partnership, right? I’ve had people on the show that are doing it solo and some with partners, what has been a huge thing for you? Because it could go either way, right?

You could have the best intention and you can have this great partnership but it could also go south. So how do you make this partnership really work for you? 


Yeah. Like you said, there’s no one way to do it. There’s no one way to eat an Oreo so to speak. I guess you just got to follow your instincts as far as if you want to do it with a potential business partner or do it alone.

It was very easy for me so I’m not an expert on that because it was my best friend that I’d grown up with since the playground so the trust was obviously there. Every business model is different so I can’t make a general statement on whether you should do it alone or not. 

What I’ve learned from living most of last year in Bali is just follow your heart, listen to your heart, and usually, it will lead you in the right direction. 


When you first started your business and you were off to Asia, how much money did you actually save and how were you able to make it last? 


I remember I quit my job and I had 8K saved and that we’re like, “Okay, that can get us 6 months in Chiang Mai.” So in Chiang Mai, you can live on a thousand bucks a month for a nice balanced life.

At about month 5, that’s when our Amazon products started selling and profiting around 1K a month. It went to 2k a month, enough for Parker and us to split to cover our living expenses. So just in the nick of time, Amazon started depositing those payouts that can keep us out there. 


That’s the best, right? When you can actually live off your business. I think there’s no better feeling than that ‘cause you’re like, “Oh my God, I can’t believe this worked.”


Yeah. Especially something as passive as e-commerce and Amazon in particular where it’s just when your listing is there, it just gets traffic and people just buy while you’re sleeping. And so yeah, no better feeling than passive income, just money getting deposited into your account. 

That’s why folks like me and you can’t stop shutting up about it because once you go to passive income you’re like, “Okay, I’m never trading my time for money again.”


Yeah. Like you said, you don’t have to constantly look for it. You’re chasing. It’s just coming to you which is the best thing. You feel like celebrating every time you see another sale you’re like, “Yes!” 


Yeah. Every time. It’s almost surreal. Compared to a job, you got to go into the work every single week for that paycheck, for that week or whatever. And then once you start a business, it’s just running and the checks just come, money just appears in my bank account.

So you do the work once and then the money keeps coming and it’s so clear for folks like you and, obviously, for most listeners here. 


Yeah. It’s like magic, beautiful magic. 


Magic money.


Yeah. You’re like, “Yes! That’s awesome.”

What are some of the best ways to start your business and make your tasks easier? 


Oh gosh, do you mean like productivity things or what?


Anything that really helped you out to make your business a lot better stronger and really helped you pivot to where you are right now. 


Well, I think first of all YouTube you to change my life basically. Sounds corny but the first step of that was unsubscribing from cable TV. So when Parker and I moved into an apartment together after college, I worked for Comcast the cable company so I could have signed us up for the cable package and I would have gotten the commission for it, I remember I made the decision. 

I was like, “No cable TV. We’ll just do Wi-Fi and plug in the Apple TV or whatever.” And so because of that, we started watching only YouTube and from there just went down wormholes, about things we’re passionate about like travel and stuff. That led me all the way here six-seven years ago. 

So yeah turning off the TV was actually one of the life hacks that I spoke about at Johnny’s Nomad Summit. It came full circle and he invited me to speak at his Summit in 2017. 

So that’s one of my biggest things: turn off the TV and listen to podcasts of course as well. It goes hand-in-hand, there’s a lot of podcasts on YouTube as well. For people listening to this, they already know that. 

I told my parents about this too and they finally just did it actually last month. They cut the cord, canceled their TV, and just onto steaming. And so I think that was a big life hack. 


It’s like entertainment that actually changes your life. Isn’t that awesome?


Yeah. The good kind.


Let’s fast forward to 40 to 50 years from now and you’re looking back at your life. What legacy would you like to leave and what do you want to be remembered for? 


That’s a good one. My whole vision: I just want to increase the net happiness of the world. Not sure exactly how that’s going to be, how I’m going to do that. But all I know is, so far, I’ve already been… 

Oof! That was a chaching from my Shopify store.


Yes. Love that. 


Yeah. We have our own Shopify store now for some of our best-selling products, just kind of getting into it. 


That’s awesome.


But yeah, I do know that so far in my life. I’ve been very blessed to have been able to help hundreds and hundreds of people get towards where they want to go specifically. I’ve been able to help hundreds of people start their own online businesses which I think is one of the most valuable things you can give to someone.

It’s like the old saying: you can give someone fish – that’s good but if you teach them how to fish then they can eat for life. So teaching someone how to start, run, and grow their own online business. That’s just like a ticket to freedom, a ticket to not needing a job, to be able to produce your own independent money AKA energy.

And yeah, I want to be, I guess, remembered for kicking people in the ass to get to do what they want in life, to pursue their dreams, and inspire people to just do what they want. Traveling the world is something that pretty much all of us have in common that we all want to do. It’s just when are we going to be able to do that? 

And so far I’ve already been able to open a lot of advice through my travel blogs and YouTube channel about what is possible if you have an online business. You can travel the world now in your twenties, in your 30s, don’t have to wait until you’re like ”retired” until your parents age to get free and go sail around the world.  

You can do that now just leverage the magical tools that we have called the internet and these apps, platforms, and stuff. Lucky to have already made a little impact in the world and that’s just me passing it on from those who passed it to me. 

So Tim Ferriss and the 4-Hour Work Week, that book is coined as the digital nomad Bible, that was released in 2007. And then that was one of the first books of its kind: writing about running an online business while traveling the world and then that inspired people like Johnny and Jubril who, through their content, inspired me and inspired other people from there, 

So, yeah. I guess that’s my answer there. 


That’s a really great legacy to leave and you’re obviously doing it right now. And it’s just going to continue to grow in the coming years. So that’s going to be amazing to see from you, Riley. So that’s awesome. 

Are you working on anything currently that is really exciting to you?


Oh, yeah. A lot of exciting things. Like I said, I run 3 online businesses. So I have my physical product business, I have my Amazon marketing agency, and then I have my YouTube channel. But kind of tied right into my YouTube channel has been my Amazon courses. 

So the story of that is after 1 year of doing vlogs, travel vlogs, the most common question I get unsurprisingly was, “Okay Riley, you’re living that life, how do we do what you do?  What is this Amazon thing, how do I do this too?”

And so after another year of just answering comments, questions, and stuff I’m like, “Okay. I’m getting so many of the same questions about what this Amazon thing is all about, I got to record my answers, obviously, I’m a video guy.

So recorded tons of videos, dozens of videos, and put them into an Amazon course. Launched that in 2016, following by the book: whatever your audience asks for, deliver a product or service to serve your audience – basic business stuff. 

And so I launched in 2016 and then kind of got a little lazy after that until when corona hit actually. I was actually planning on updating the course for 2020 anyway, but during corona, when that hit, I was like, “Okay, I got to do this now.”

So during corona, I’ve been filming tons and tons of new videos, updating my complete Amazon course to reflect everything I’ve learned over the past four years. All the updates, tips, tricks, strategies, all that. So I’m really excited about that. 

And I have a new partner in that business and we have reframed it from just a normal video course into a 90-day challenge. So very exciting. It’s basically a 12-week program where we help people launch a product on Amazon even if they have no idea what they want to sell yet.

We’ll help you go through the research process: looking around the internet, looking for trending things, how to come up with a differentiating idea, look for a supplier and negotiate with them, get something penciled up, and how to create a really awesome physical product.

So yeah, that’s what I’m working on now. Round one has already been going on for the past month-and-a-half and round two is opening up soon. It’s called 90-day FBA. So that’s my new business.


That’s really exciting and such a great resource for people to go to because a lot of times it’s such a headache to search all of that stuff online. So I’m always happy to see people like you, Riley, who just make it all in one package and so much easier for all of us.

Now, if our listeners want to know more about you, where can they find you? 


Oh, yeah. Well, I guess my main thing is my YouTube channel called Livin That Life. So And my second main thing I guess is my Instagram @livinthatlifetv. 

And also I have a website. I haven’t been posting many blogs on my website but LivinThat is where you can find my websites, more about me. I also have a resources page: LivinThat actually where I’ve been compiling all my favorite apps, tools, resources. 

So to go along with your question about that, I’ve been just compiling them on that one page. 

So yeah, that’s where you can find me.


Perfect. Thank you so much, Riley, for being here with us and sharing all of this. We really appreciate you. 


You are welcome. That was my pleasure. That was fun.

Listen to Riley’s extended interview where he shares how to start an online business using Amazon FBA.

What you’ll find:

In this episode, Riley shares his kept secret on how you can utilize Amazon FBA to launch your online business.

Follow Riley:

Show Credits:

Audio Engineer: Ben Smith

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