Brian Kidwell – Alert! Cheap Flights from a Digital Nomad – Opt Out

Brian Kidwell – Alert! Cheap Flights from a Digital Nomad

2 years ago · 1:15

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What’s the biggest expense most people face when they want to travel?The answer is the cost of your flight. Whether you’re a single nomad ready to backpack Europe or Southeast Asia, or a family of 5 trying to do more than take another boring trip to Florida, travel plans live and die by booking your flights. You want them cheap. You want a deal. And you have to lock them down before you can start fantasizing about all the fun that lies ahead.

Our guest is Brian Kidwell. Officially, he’s the co-founder of ScottsCheapFlights, a business that emails the best international flight deals of the moment to a list of over 1 million loyal subscribers.

Brian’s “opt out” story isn’t hard to figure out. He runs a company with a remote team that spends their days finding mistake fares and unpublished sales from airlines. Over the course of the last few years, he’s grown the business from locations that include his parents house, to co-working spaces in Bali, Thaliand, South America, and now, from Austin, Texas. You can bet it won’t be long before the right cheap flight deal sends him packing for another adventure.  Listen now to Brian’s story.

Highlights from Episode 13 with Brian . . .

Telling us about how ScottsCheapFlights works, and the best deal he ever got off the service . . . 
“My best mistake fare was a 165 dollar flight round-trip from Tai Pei to Sacramento. That was insane. I didn’t even take the other leg back ’cause I didn’t want to go back to Tai Pei, I just wanted to get back for the holidays. Most of the flights are unpublished sales so the airlines will either be competing with each other or trying to gain market share in a certain hub so they’ll drop their prices. Another airline will see that, they’ll drop their prices. It’s just all around good for consumers. Their not sending this out to their customers and so what we do is we have a team of people that all they do is search for cheap flights every day.”

On the value of having what we call “The Audacity to Reach Out” . . .“It’s funny, I was thinking about this recently. The biggest points in my career or life or business side, have all come from cold emails. In college, I emailed a random professor and that got me involved in an entrepreneurship organization. Then, I was following this guy’s blog. I saw him up in San Diego and I emailed him and he had been a great mentor for me. Then, I get back from traveling and I email this guy and just say, “Hey can I interview you” … The thing that I’d always do when I cold email people is figure out how I can provide value. I try to find the angle on what they’re doing and figure out what I have to offer to make them interested.

How they’ve grown’s email list by doing social giveaways  . . . 
“What we do … If you think about a giveaway, most giveaways, you sign up for something and you hope that you win. There’s no incentive to tell your friends because if you tell your friends then your chances of winning just go down. There’s something called a viral giveaway and what these do is you will get one entry for entering the giveaway. If you refer your friend, we’ll give you ten entries. It incentivizes you to go tell other people and that’s how you collect more email addresses. You get more people about the giveaway and then they’re opting in to your email subscription..”

Explaining how he didn’t really have a plan to get into a travel business, let alone become a co-founder of  . . . 
“You guys kind of hit it on the head there. When I got back from Europe, my parents asked me what I was going to do. My whole time in Europe I was like, “Ya know, I’m going to go out there. I’m going to think about what I want to do and I’m going to come back with a plan.” On the plane back I was like, “I have no idea what the hell I’m going to do.” So, my parents asked me that question and the best response I could come up with was, “I’m going to get a business off the ground and I’m going to move to Southeast Asia next year.”


Nate Broughton: 00:00:02 This episode of the Opt Out Life podcast from the Opt Out Media Network was recorded here in San Diego as the Opt Out Life story of Brian Kidwell.
Speaker 2: 00:00:14 Welcome to the Opt Out Life podcast. The no BS guide to living the modern good life. Hosted by the subversive millionaires Dana Robinson and Nate Broughton. The Opt Out Life podcast explains how creative hustlers are turning side-gigs into real income and taking back control of their time. From their studio in sunny San Diego the Opt Out Life welcomes guests who are solopreneurs, entrepreneurs, travelers and creatives who are proof that you can choose a lifestyle over money but still make money too. If you feel like you’ve been chasing your tail, running the rat race, or stuck in a system that’s rigged against you, we’d like to offer you an alternative, here on the Opt Out Life podcast.
Dana Robinson: 00:00:56 What’s the biggest expense most people face when they want to travel? The answer is the cost of your flight. Whether you’re a single nomad ready to backpack Europe or Southeast Asia or a family of five trying to do more than take another boring trip to Florida. Travel plans live and die by booking your flights. You want them cheap. You want a deal and you have to lock them down before you can start fantasizing about all the fun that lies ahead.
Nate Broughton: 00:01:20 Our guest is Brian Kidwell. Officially he’s the co-founder of ScottsCheapFlights. A business that emails the best international flight deals of the moment to a list of over one million loyal subscribers. Brian’s Opt Out story isn’t hard to figure out. He runs a company with a remote team that spends their days finding the stake fares and unpublished sales from airlines. Over the course of the last few years, he’s grown the business from locations that include his parents house to co-working spaces in Bali, Thailand, South America and now from Austin, Texas. You can bet it won’t be long before the right cheap deal sets him packing for another adventure.
Dana Robinson: 00:01:54 What’s cool about Brian is his business is a crystal clear reflection of who he is as a person. A 25 year old struck with wanderlust who has an impeccable combination of entrepreneurial hustle and a willingness to chase experience. As you’ll hear this didn’t happen by accident. No one his age or for that matter, no one at any age, gets this handed to them. Listen for how he went from being a digital nomad with his own small projects to a full partner in this widely successful travel service. And by the way, why isn’t it BriansCheapFlights? As you’d expect, there’s a story there.
Nate Broughton: 00:02:29 So make sure your seat backs and tray tables are in their full upright position and that your seat belt is correctly fastened. We’re cleared for take off. Thanks for choosing Opt Out Air.
Nate Broughton: 00:02:42 Dana is here, he’s smiling and looking pretty. We have Mango Even Keel session IPA from our not sponsor Ballast Point and our guest today is Brian Kidwell from Welcome.
Brian Kidwell: 00:02:57 Thanks for having me guys.
Nate Broughton: 00:02:58 If you do not know what is you are weird because there are over a million people on their email list and you’re going to be happy that you get to hear this story. Not only of what it is as a business but what it is as a service because if you like the opt out life, you need to be on ScottsCheapFlights. Good advert there.
Brian Kidwell: 00:03:19 I liked it. I liked it a lot.
Dana Robinson: 00:03:21 It’s Friday eve and it’s in the late afternoon which means, as my wife says, it’s four o’clock somewhere.
Nate Broughton: 00:03:29 There it is. Leftover from the Chris Hedgecock episode. Beers, cheers.
Dana Robinson: 00:03:34 Cheers, gentlemen.
Nate Broughton: 00:03:37 We feel like the episodes go better when we drink so, here we go.
Dana Robinson: 00:03:43 Very even keel.
Nate Broughton: 00:03:45 Yes, I’m excited because we are going to get to talk a lot about travel because ScottsCheapFlights, if you haven’t deduced yet, is about travel. It is an email subscription and an email service that delivers via email, cheap flights to its subscribers. I don’t know how many times I can say flight and subscribers and what it does but I just danced around that. That’s what it does and I love it. I love it as a business and I love the topic of travel. Today’s going to be a travel, travel episode. Let’s chat.
Nate Broughton: 00:04:16 Brian tell, since I just did a shitty job explaining ScottsCheapFlights and stumbled over my words, why don’t you tell us what ScottsCheapFlights is and then we’ll get a little deeper into your story and why it’s so cool.
Brian Kidwell: 00:04:29 Sure, absolutely. ScottsCheapFlights is a freemium subscription service that sends out cheap flight deals. We have two tiers of subscribers. We have the people that pay us money and get a better service. Then, we have the people that sign up for free and get a great service at cheap flight. We send them all out via email. You can sign up, choose your departures regions as a free subscriber and just save a ton of money on flights. Everything’s international, 600 dollars to Australia.
Nate Broughton: 00:05:04 600 to Australia, 200 to Paris, 500 to Shanghai.
Brian Kidwell: 00:05:09 There pretty ridiculous. We have mistake fares air fares. That’s when airlines make mistakes and we catch it and we send it out to our subscribers. The ones that are always looking at their email and want to travel will book those flights. I just got one 533 dollars from LAX to New Zealand non-stop and then we sent out one for 333 a week after. I was still happy about my 533 dollar one but …
Dana Robinson: 00:05:36 That’s crazy.
Brian Kidwell: 00:05:37 Yeah it’s nuts.
Dana Robinson: 00:05:38 Is it mistake fares most of the time or is it …
Brian Kidwell: 00:05:41 The mistake fares are rare. Those are the good ones. My best mistake fare was a 165 dollar flight round-trip from Tai Pei to Sacramento. That was insane. I didn’t even take the other leg back ’cause I didn’t want to go back to Tai Pei, I just wanted to get back for the holidays. Most of the flights are unpublished sales so the airlines will either be competing with each other or trying to gain market share in a certain hub so they’ll drop their prices. Another airline will see that, they’ll drop their prices. It’s just all around good for consumers. Their not sending this out to their customers and so what we do is we have a team of people that all they do is search for cheap flights every day.
Brian Kidwell: 00:06:23 When we find particularly good ones … We’re taking everything in to account. Is this a good airline? Are you going to have to pay extra for bag fees? Are there stops? We take all this into consideration when we’re sending out deals. We take the hard work out of finding a cheap flight and make vacations a lot easier to go enjoy.
Nate Broughton: 00:06:43 It’s such a beautiful thing for so many reasons. It’s a very simple business as he just described. It’s taking advantage of an inefficiency that’s there. It’s a very compelling offer I think, for people to get on the list. Who would be annoyed by cheap airfare options? We’ve talked a bit about travel both here on the podcast and on our upcoming blueprint course about how travel often starts with the flight. If you get the flight, now you can figure out the rest. It’s often the biggest expense. Especially internationally, it can be. It’s the genesis of any trip so if you’ve got the wanderlust bug or if you’re someone who knows they want to take a vacation sometimes this year. Maybe in the summer to a general region with your family. This service will just dump them right into your inbox and if you act quick you can save, sometimes 80 percent off the fare.
Brian Kidwell: 00:07:33 Yeah, its nuts. Most of the flights … These aren’t last minute flights. Most of them are two to six months out. If you’re traveling anytime in the next year and you’re just wondering what’s out there. It really helps to be flexible and say, okay I want to travel, I don’t know where exactly but I have a list of places that I want to go and the chances are we’re going to send a deal to one of those places on your list. Just being flexible with when you’re going as well. If you have a job and two weeks vacation it becomes a little bit more challenging but it’s still fun.
Nate Broughton: 00:08:04 If you’re one of those that are still opted in, you’ll be a better user of ScottsCheapFlights, is you opt out. Still, I think anyone can take advantage of the service. You mentioned there’s a free version, there’s also a paid premium model. How much does it cost to get the paid service?
Brian Kidwell: 00:08:20 Right now, it’s 39 dollars a year.
Nate Broughton: 00:08:22 Right, so that’s … I mean that’s a joke.
Brian Kidwell: 00:08:24 You’re going to save five or six hundred dollars on a flight if you have a family, if you have a girlfriend or husband or whatever, the savings add up very quickly. 10, 15 x savings on the flight prices if you just book one flight. That’s what we tell people, “Yeah, if you book a flight in the next fifteen years, it’ll pay for itself so you’re good there.”
Dana Robinson: 00:08:45 Alright Nate let’s break in. I’ve got a couple things and to use a euphemism that might apply to travel let’s unpack …
Nate Broughton: 00:08:52 Unpack.
Dana Robinson: 00:08:53 Let’s unpack these couple of things. What we’ve been talking about I think, gives us two cool things to talk about. One is the business itself. So many people are looking for how to set up their own side gig. How to make money online and so our guests are great models for how do you do that. How do you get your side-gig and do something cool to make money, but we’re also getting all this great travel advice too. Let’s just start with the business of the business. I’m fascinated by a couple of things here. One is they’re hand curating this information. This is not just an automated algorithm that’s out there grabbing information and pumping it into daily emails.
Nate Broughton: 00:09:30 Yeah you would sort of expect it would graduate to that point ’cause this business has been around for a while. It’s cool to hear him tell us a little bit about the mechanics. How they have staff and how they’re hand picking these things. Not only had finding them which is a skill unto itself, but also curating them for their audience. I think it’s cool to hear him talk about that ’cause it gets further in the story as we hear him talk more about how they are really managing this as a membership. They are caring about the people who get these emails. This isn’t just some bot that spitting out, oh there’s a cheap fare to Tai Pei right now. That speaks to the longevity of the business and why it’s had success so far.
Dana Robinson: 00:10:07 Yeah. I think of a lot of the past of say, internet flash in the pan. There was a time when you could just put a bunch of content on a blog. You could even auto algorithmically post to blogs. Those businesses might make a little bit of money in the short term and we’ve known some people that have done that, but they don’t have longevity. I think that hand curation here, is what people really want and they’re willing to pay for that. It’s created a business that’s standing the test of time in the face of stiff competition.
Nate Broughton: 00:10:36 Potential technological advances that from the outside looking in, you think that this thing could get beat or removed in an instant and as you learn more about it you understand that there’s actually more there.
Dana Robinson: 00:10:46 Yeah. I’m also amazed, business wise, that they can sell this thing for a little over three buck a month. I don’t know of any subscription based service that has that compelling of an offer. I guess it’s just volume. If you get this kind of scale, you get a million users, then your premium subscription plan can be pretty damn cheap.
Nate Broughton: 00:11:05 Yeah and it’s a compelling offer though. I think he gives the example of, if you buy a flight over the next 15 years the subscription is going to pay for itself because we are talking about savings of hundreds and hundreds dollars on most of these thing. I don’t think it’s that much of a leap for someone to really pay for this at that rate. It’s almost like both sides are doing well in this scenario.
Dana Robinson: 00:11:27 Right. I think it’s a cool lesson for the side-giggers and entrepreneurs, you could have a pretty compelling business if you price is right. People can do that math and you could sell that but I think it sells itself. It doesn’t seem to me that you need to explain to people that you pay 39 dollars for a year and you’ll obviously only need to book one flight and you’ll have made money back.
Nate Broughton: 00:11:52 Yeah. The simplicity that surrounds this business, both in what it does and also in the perceived value and the real value that can come along with paying for the paid side of it, is one of the things that I just love so much about it. Let’s talk a little bit about the travel side, while we’re breaking in here too. We’re illustrating to folks that they should be looking out for these things. You want to opt out. You want to travel a lot. Even if you are just an average travel, there is almost no reason you could give me to not be on ScottsCheapFlights list. If you’re going to travel it always starts with the flight and why not spend half on the flight that you were thinking you might have to spend. It could be the genesis for more travel. There’s just no argument that you could give me to not be on this list.
Dana Robinson: 00:12:34 Right and I think a lot of people don’t realize that there’s this kind of list out there. If you’ve booked with Orbitz or some of the big programmers that are all tapped into saver, certainly you can get alerts and those are useful. That’s a travel hack for sure, but a lot of people didn’t know you could get alerted to mistake fares. Literally just see a mistake fare, book it fast and then figure out that you’re going to take this cool trip that you spontaneously bought because the airlines have to honor the price when they’re up. I think it’s cool to learn that there’s even deeper travel hacks than just monitoring the systems for when prices might hit a low.
Nate Broughton: 00:13:09 I love it. We’ve talked a little bit about the business itself, let’s hear how Brian got involved in this business in the first place because it is an amazing story.
Dana Robinson: 00:13:16 How’d you end up in the business?
Brian Kidwell: 00:13:18 I used to live in San Diego. I got into commercial real estate for a bit. I kind of felt stuck and I ended up selling everything and I just wanted to travel so that’s what I did. I sold everything here in San Diego. I went and back-packed Europe and when I was looking for a flight, needed a cheap flight ’cause I was broke. I bought an ebook on how to find cheap flights on Amazon and that was written by my now business partner, Scott. I didn’t know him at the time either.
Brian Kidwell: 00:13:47 I came back and I was working on starting up a couple of websites of my own, a few different businesses. Getting something off the ground. I emailed him and we kept in touch over time. Eventually we realized that we had complimentary skill sets and decided to sign a profit sharing agreement and say let’s see if we can do something here. That profit sharing agreement turned into a legitimate business. We have about 30 team members around the globe. Sending out deals 24/7 to people all over the world.
Brian Kidwell: 00:14:20 It’s funny, Scott and I didn’t meet for the first year of working together. I was in Thailand and Vietnam getting this business off the ground and he was in Colorado. We would just Google chat in the mornings and evenings and then work all day. We didn’t really talk on the phone much. It was a very interesting way to get into a business partnership with somebody that I had never met before.
Nate Broughton: 00:14:41 Yeah, you kind of jumped the shark on me there ’cause I knew that story and I think we should celebrate it a bit because it follows some of the things that we preach on the Opt Out Life. You just described, not only that you made your own opt out, where you were like, I’m going to sell everything here. I wasn’t happy and you went to travel the world. That actually led you to find this business which is kind of cool, indirectly. Even more interestingly than that, you just started chatting with this guy online and it’s become this career. What was the first email message you sent out to him?
Brian Kidwell: 00:15:11 It’s funny, I was thinking about this recently. The biggest points in my career or life or business side, have all come from cold emails. In college, I emailed a random professor and that got me involved in an entrepreneurship organization. Then, I was following this guy’s blog. I saw him up in San Diego and I emailed him and he had been a great mentor for me. Then, I get back from traveling and I email this guy and just say, “Hey can I interview you” … The thing that I’d always do when I cold email people is figure out how I can provide value. I try to find the angle on what they’re doing and figure out what I have to offer to make them interested.
Brian Kidwell: 00:15:54 For Scott, he had literally … Going back to the beginning this was for his friends and family. He was sending out emails to his friends and family to let them know about heap flights. It got over the 2,000 mail ship subscriber limit and he didn’t want to pay for that. It had just blown up on some Business Insider article or something so he got a bunch of random internet strangers on his email list. He didn’t want to pay mail ship to send out emails so he started charging two dollars a month. I was on his email list at the time ’cause I bought his ebook. I just simply asked him, “Hey, can I buy a couple subscriptions and give them away to the audience that I was building at the time.”
Brian Kidwell: 00:16:32 He was interested, so we interviewed and one thing led to another and he was asking me for my help. I was just trying to figure out how can we get this thing off the ground. I thought it was cool at the time too. He was just starting out, looking for some marketing opportunities.
Nate Broughton: 00:16:45 What was it about you that was maybe a little bit different? Why do you think you guys were able to develop a relationship. I love what you said about researching the person, the situation and thinking about what you can offer that’s going to make you stand out from the noise that is hitting his inbox. What was compelling, do you think, about you as a person or maybe you guys just kind of hit it off ’cause you shared interests? What was it?
Brian Kidwell: 00:17:09 I think it’s ’cause I had traction with some of the other stuff I was working on. He saw that I knew what I was doing. I had experience in marketing. I could build websites. I wasn’t an expert in any of this but I had the skill sets that he was lacking. He’s damn good at finding cheap flights and talking to the media and all this stuff but he didn’t have someone to build him a website or do the marketing side of things. It worked out perfectly. I was not looking for this, I had clients, I had my own companies at the time and he asked me if we wanted to sign an agreement to sell a two dollar a month service. I was like, “Yeah, this isn’t going to be anything serious. I was like, sure dude whatever, let’s do this.” It turned into something way more than that. I think that just comes down to a lot of luck and good decisions we made along the way.
Dana Robinson: 00:17:57 What was the business you were doing when you first met him? You said you were trying to build a platform and wanted to give some subscriptions to your own audience.
Brian Kidwell: 00:18:05 I had a few different businesses that I was trying to start off. Some of them more successful than others. I noticed two things when I was traveling. One, people want to save money and two, people want a community. I was trying to build a community of travelers and basically offer them discounts on different travel related items, was the long term vision. Scott saw that and I was growing an Instagram account pretty quickly. I was building out the website. It all looked good and it had traction. I ended up shutting all that down a few months into working with Scott because we were able to move that a lot faster than what I was doing.
Nate Broughton: 00:18:45 You have some hard tactical skills in online marketing, digital advertising, how did you develop those? If we take a step back, you were a college student. You’re entrepreneurial, President of the Entrepreneurs Society, which is a great program that we’re going to plug again at San Diego State. I don’t know how many guests were going to have that went through that program but it is very impressive. The instructive lesson that we pulled out of it is, if you’re young and you’re in college you need to look for things like that to become a part of because that is worth a hundred times more than your degree is worth. It’s cool to talk to another person who was involved in that group and see them successful at a very young age. Your age is 27?
Brian Kidwell: 00:19:27 25.
Nate Broughton: 00:19:27 25 okay. Beating Alex Martinez for the youngest, alright. How did you develop those technical skills? Were you just screwing around on your own? It’s not usually something that you do learn in school so I think it probably had to come from curiosity and testing things out.
Brian Kidwell: 00:19:43 Yeah for sure. I’ve always had the entrepreneurial bug or what ever you want to call it. I was constantly trying to start my own business throughout college. I realized that I didn’t have the skills so freshman year of college I was doing internships for SCO. Basically anything I could get my hands on and I found people that would refer me to other internship opportunities. Eventually that turned into client work. I go from making ten dollars an hour as an intern or interning for free to charging clients thirty dollars an hour in college. You learn a lot just going along. Your clients ask if you could do something and you’re like, “Yeah I can do that” and then you go figure out how to do that or find someone that knows how to do that and get their help. A lot of it was that and then the other side of it was … I don’t know how to do everything.
Brian Kidwell: 00:20:33 I’m not an expert in marketing or website design or anything like that but if you’re bootstrapping a company and you don’t have money to go pay a developer or a designer or anything like that, you gotta figure something out. That’s what I did. I’d go look at other websites that I thought were conversion optimized, had good design or anything like that. I would take those principles and figure out how to build that in word press. There’s no play book or course or anything that would teach me everything I need to know for this. It just came down to figuring out what the issue was that needed to be solved and then googling it. Someone’s solved your issue before. You just got to figure it out.
Nate Broughton: 00:21:15 Well if you’ve listened to this podcast at all, you know that the last ten minutes of Brian telling us how he’s found opportunity and how that opportunity has led to ScottsCheapFlights is something that we love. It follows so many of the tenants and ideas that we have and that we try to bring out in these stories. It was almost like we gave him a script. This kid is 25 years old, he like some of our previous guests who were young he was very thoughtful. Maybe not on purpose, maybe he just came out this way. He comes out of the Entrepreneur Society at San Diego State. He’s reaching out to people while he’s there who think can be mentors. He’s reaching out to people in the business community and asking for internships.
Nate Broughton: 00:21:58 There is this hustle there and what we call the audacity to reach out that is … He says has really been every opportunity that has come to him in his life has been from a cold email to someone that he’s interested in. Listen to what he says about that approach. He doesn’t just send it off and ask for something, he spends extra time and tries to figure out what value he can provide to that recipient. This is something we talk a lot about in out upcoming blueprint course actually because it’s something that I would argue has been the biggest point of success in my life too. The audacity to reach out. I love that Brian gives us this story.
Nate Broughton: 00:22:33 He is a partner in ScottsCheapFlights simply because he was building his own business in the travel space and came across ScottsCheapFlights and sent an email to Scott to open up a conversation. It just was dumb luck really. He straight up say, “I was not looking for this and I didn’t think it was going to become that big of thing.” A relationship was born and now there’s an extremely successful business here for a very young person.
Dana Robinson: 00:22:57 I think part of the audacity to reach out is you’ve got to have some ambition to do something in a way that’s maybe not entirely selfish. Here Brian’s doing something and it’s bold to just reach out to the owner of the successful site and say, “Hey, I want to buy some of your seats so that I can give those away as a promo.” Make the introduction. What a lot of our listeners may not realize is just how desperate successful entrepreneurs are to find other ambitious people to come a long beside them. Here you’ve got Scott, he’s kind of killing it accidentally and he’s a little bit ambivalent about it. It’s got too much traffic and he needs somebody to come along side and pour some ambition in to his project.
Dana Robinson: 00:23:45 This has repeated itself in my life and I know in so many other people’s lives. Even for people that have come to work for me. The best people in my life have been people that showed up and said, “I would like to work for you.” In some cases for free. They pour their ambition into my venture because I’m exhausted sometimes. I’m going in ten different directions and so I think it’s a great lesson, that reaching out and being ready, willing and able to pour that ambition into someone’s venture, can lead to something amazing.
Dana Robinson: 00:24:14 There’s another sort of related theme that I’m not sure has come up to the forefront of our podcast and that’s serendipity. What’s really fun about reaching out and just being willing to have conversation and to just take a chance is that serendipity happens. It’s just cool shit happens, when you do this. Friendships happen. That’s how you and I met, Nate, from a serendipitous meeting that was from you reaching out to someone who was reaching out to me and then we end up connected. We end up business partners, life long friends, godfather to one of your little rugrats.
Nate Broughton: 00:24:55 They call them groms in this town.
Dana Robinson: 00:24:56 Groms that’s right. Future groms. We’ll be teaching them to surf in another year or two. Serendipity is just a beautiful aspect of the audacity to reach out.
Nate Broughton: 00:25:06 Yeah. It was the reason I wanted to have Brian on this podcast. It’s such a compelling and cool business but I knew the story behind how this all happened. If there’s any story that can show you the value of it, it’s this. It’s two young guys playing around with travel, that connect via email and don’t even meet for an entire year after they become business partners. That’s pretty rare so I wanted to get that out there and hopefully we’ve not only illustrated it by hearing it directly from Brian but keying in on the most important parts of it as they relate to the Opt Out Life here. So let’s hear some more.
Nate Broughton: 00:25:41 That was our first Zapier shout out. Took 13 episodes to shout at to my boys at Zapier.
Brian Kidwell: 00:25:47 Yeah our company would not run without Zapier.
Nate Broughton: 00:25:50 I was there the night it was founded. At a start-up weekend. I was a little too drunk to realize I should invest in it. Shout out not only to Zapier but all of my friends who invested in it.
Brian Kidwell: 00:26:01 We all make mistakes.
Nate Broughton: 00:26:05 That’s actually become a social credibility piece. “Yeah, I know those dudes, they used to work for me.” “They used to work for you, holy shit.” They’ve long surpassed me.
Brian Kidwell: 00:26:14 Great business though.
Nate Broughton: 00:26:15 Yes. Great business. Everyone loves it. The reason that the ScottsCheapFlights situation happened was because of a few things. You were already playing around and developing a skill set. You were interested in travel and because you had the audacity to reach out. Those things were not deliberate towards creating this opportunity and now this business that your co-owner of. It’s cool to see the product of having that attitude, curiosity and that willingness to just do it, pay off. At such a young age too. In the coolest fucking business of all time by the way. I don’t think I’ve been able to talk about this enough.
Nate Broughton: 00:26:52 We’ve talked about why ScottsCheapFlights is great for the user. We’ve talked a bit about what it is and how it works. Imagine you are the owner of this business. It’s travel related so your talking about travel all day long. You’re looking at flights. You’re finding flights. Your community is about travel. Everybody loves travel. Your delivery mechanism, your product is emails. Which is a one to one communication between you and an end user.
Dana Robinson: 00:27:19 With people that want to receive the email.
Nate Broughton: 00:27:21 Yeah, they’re begging for these emails. Every one you send, they open. Open rates have to be crazy. There’s this element to it that it’s like the lottery, in that if you get off the list, if you don’t pay attention you’re going to miss that one flight that saves you 600 bucks.
Dana Robinson: 00:27:34 FOMO.
Nate Broughton: 00:27:34 FOMO.
Brian Kidwell: 00:27:35 I love the FOMO.
Nate Broughton: 00:27:36 Beautiful. It can be used around the world, international. Do you guys have people all over the world using it now? Are you doing flight … Wasn’t it just domestic when you started?
Brian Kidwell: 00:27:45 No. It’s always just been international flights but only in the US when we started. We did too good of a job explaining that people because people still think it’s only in the US but we sent deals from everywhere except Africa, which we’re going to be launching this year. Then we’ll be completely worldwide.
Nate Broughton: 00:28:05 There are some potential technical hurdles or industry things that could make it harder to kind the deals, I guess. The longevity of the business already to date I think has proven that it’s got some sustainability even if you could have hypothesized that the airlines aren’t going to do that anymore or Google’s going to come out with a tool that’s going to make it go away. It doesn’t even necessarily matter because you have so many people on an email list. You’ve got a community now. That can’t be taken away from you no matter what.
Brian Kidwell: 00:28:33 Right. That was something that Scott and I early on, we didn’t know if it was going to be shut down tomorrow. We were just, we’re still kinda like this, we’re just excited that it’s still around and we’re trying to improve it every day. The longer it’s in existence the more confident we are that it will continue to be in existence as we move forward. There’s other companies that have been around for 10, 15 years that do something similar. Not the exact same model but heap flights aren’t going away and people like to travel and they’re going to continue to want to save money. I think the longevity of the business is definitely sound. I’m sure there’s going to be issues down the road.
Nate Broughton: 00:29:15 It’s a business.
Brian Kidwell: 00:29:16 Yeah exactly.
Dana Robinson: 00:29:18 There’s a common business myth that in order to make it big in business you have to have an idea that totally novel. No one’s done it before. Reality is a flourishing market is a good sign. When you notice that there’s banks across the street from each other. Gas stations caddy corner to each other. Starbucks competing with Starbucks across the corner. The fact is that there were already players sending emails with cheap flights and there are new ones since, and here you are. You’re sustaining that.
Brian Kidwell: 00:29:52 Yeah. I wish I knew that early on in my entrepreneurial endeavors ’cause I’d always think it was about the idea. I’d wait for a good idea or I’d try to think of a fantastic new idea that no one’s ever done before and that’s BS. Go look at what people are already paying for or they’re not paying for, figure out what people are excited about and come up with something unique. A new brand or a new business model around it. It doesn’t have to be something that’s never been done before. Quite frankly, you’ll probably have more success if you figure out what has been done before and just do that differently.
Dana Robinson: 00:30:28 Maybe you can talk a little bit about the business that you shuttered. You had a business that you were starting. Was that a business that was just too novel, that would take too long to get market adoption and you then enter a market, cheap flight communications that’s flourishing even with competitors.
Brian Kidwell: 00:30:45 I think that building a community is one of the most difficult things that you can do from scratch. That’s what I was trying to do. Would it have worked. I think so. It had traction. There were people there, they were excited about it but when you have opportunities and you’re trying all these different things. At a certain point, your times getting pulled in all these different directions, you just gotta cut out whatever you can. For me, that was cutting out this Java community piece and focusing 100 percent on the cheap flights stuff. I think it paid off but I’m not sure the idea was necessarily novel, I just think that building a community is very difficult to do, to do right. Especially to do quickly. That stuff takes time.
Nate Broughton: 00:31:31 Were trying to build a community here at the Opt Out Life, so I want to learn a little bit more from your story. What were a few of the things that happened that really jump started you guys. That got the email list growing rather than a community? Was is stuff on Reddit? What were some of the success you found early on? As you said, whether it’s a community or an email list it’s a noisy world out there. How did you guys get over that hump early on?
Brian Kidwell: 00:31:55 I think early on … It started off as something for Scott’s friends and family. Then he took a trip around the world for free because he paid for it with his airline miles. He had a friend that was working at Business Insider, I believe, and they ended up publishing a post about Scott going on this crazy trip. That ended up sending him over the mail ship limit of 2,000 subscribers.
Brian Kidwell: 00:32:18 After that, we had to be more purposeful about growth and so Reddit was definitely a piece of that. It still is. Reddit is a fantastic community of people. You gotta be careful but if you basically be a Redditer and speak to them like you would with your friends and provide value then you’ll be successful. That’s what we did. Scot would go on there, we would go on there, and ask people like, “Hey, do you have any questions about finding cheap flights.” Of course people do, they’re looking to go on vacation and so they would ask us those questions. Scott would go out and find information or find cheap flights right there on the spot and help people travel.
Brian Kidwell: 00:33:05 We just blow up on Reddit and we get a ton of subscribers early on. The nice thing about that is that just sparked the word of mouth. People were excited about it. They just found out about this guy with a cute dog sending out cheap flights and now they’re telling their friends.
Nate Broughton: 00:33:23 Dana, I did not know this point actually. I said that I’ve known the story of ScottsCheapFlights. That’s why I wanted to have Brian on here ’cause it’s a cool story for a few different reasons as we’ve talked about with our break-ins here but I did not know that they have grown this thing 100 percent organically. An email list with over one million subscribers. That’s right one million without buying ads on Facebook, Instagram or running anything more than just basic promo giveaways with other partners and hoping on Reddit and telling their story. I’m almost taken aback by that. I can’t believe it’s true and it’s I don’t know dude. I don’t know what to say other than kudos to Brian and imagine if they added a little fuel to the fire, how big this thing could be. It’s also kind of cool because they’re happy ding what they’re doing and they’re growing at the right pace.
Dana Robinson: 00:34:10 I guess for those that don’t understand marketing, let me put it into perspective as the non-marketing co-host. Typically, what you’d want to figure out is what’s the lifetime value of your customer. So you’d say, “Well we’re going to have this customer for three years as a premium subscriber. They’re worth 120 dollars or 117 dollars, some number like that. Then you would determine how much you can spend to acquire that customer. You might spend 100 dollars to acquire that customer. If that’s the case, you might spend 100 million dollars to acquire the customer base that they have.
Nate Broughton: 00:34:42 To acquire 27 million in profit if I’m doing my math correctly. Or 17 million right. Either way, lot of millions.
Dana Robinson: 00:34:53 Now certainly, there million subscribers aren’t all paying 40 bucks a year but you still … The listeners, entrepreneurs, side-giggers that are thinking about business, this is how you figure out your business plan. You back into it by determining the lifetime value of your customer and what it’s going to cost you to acquire a customer. Imagine having a million customers that you acquired for zero and that’s really cool. How do you think they do it Nate? There’s something very genuine about their product.
Nate Broughton: 00:35:23 I think it starts with the name, ScottsCheapFlights. It’s from a dude named Scott.
Dana Robinson: 00:35:28 It’s like McDonald’s. This is why Ray Crock just loved that name.
Nate Broughton: 00:35:32 Scott’s a guy who is out there fighting the good fight for all the travelers out there.
Dana Robinson: 00:35:37 With a dog.
Nate Broughton: 00:35:38 With a dog next to him and he’s still doing this manually. Airlines are generally perceived as evil, especially these days and it’s finding those cheap fares. He’s the Robin Hood. I think that persona plays well and there’s a huge world of travelers and potential travelers online. It makes sense that they could find places where those people hang out and come in and tell that story. It goes back to the beginning. Who doesn’t want a cheap flight offer. Especially when it’s brought to you by a guy with a dog, who’s actually also taking the time to curate this list a little bit and not just blast you with a Google alert or something like that. There’s more to it. There’s a bit of a voice and a story. I think it was not necessarily intentional but their riding a wave that is incredibly powerful. Especially without advertising dollars behind it.
Dana Robinson: 00:36:29 I think it’s really instructive as well. He was able to tap in to a community like Reddit. This is dangerous for somebody who’s not willing to be genuine. The communities that have that many active users in each sub are going to filet you if they don’t feel that you’re genuine in what you’re offering. It’s a pretty cool story. Great lesson in finding community organic growth but one that you have to have that perfect formula.
Nate Broughton: 00:36:57 Alright let’s talk about a giveaway ’cause I need to come up with one for Opt Out Life. It’s about time for us to get real and start getting people’s emails. Giving you all these great podcasts. I want your email.
Dana Robinson: 00:37:08 What can we give away?
Nate Broughton: 00:37:09 Yeah, what can we give away? What did you guys do and maybe we can borrow from that story and come up with an idea?
Brian Kidwell: 00:37:14 What we do … If you think about a giveaway, most giveaways, you sign up for something and you hope that you win. There’s no incentive to tell your friends because if you tell your friends then your chances of winning just go down. There’s something called a viral giveaway and what these do is you will get one entry for entering the giveaway. If you refer your friend, we’ll give you ten entries. It incentivizes you to go tell other people and that’s how you collect more email addresses. You get more people about the giveaway and then they’re opting in to your email subscription.
Brian Kidwell: 00:37:51 Early on what we would do is giveaway two free flights. The first time we did it, we didn’t have money so we used Scott’s air miles. We just give away two flights to wherever somebody wanted in Europe, Hawaii, South America, something like that and people loved it. People would sign up, they’d share it with their friends and it was very, very simple. We would combine that with going on Reddit and doing an AMA. That’s how it really sparked the growth early on. Now we’re doing full on giveaways like 4500 dollar giveaway packages that are sponsored by tourism boards or major companies. We’re not even paying for the packages anymore and the trips are frickin’ awesome now. People are super stoked on it.
Brian Kidwell: 00:38:37 The thing about viral giveaways though, if you get technical and talk about a viral co-efficient, it’s not actually viral but you do see 30 percent of new subscribers. People who you’ve never interacted with before. It’s a nice boost but don’t expect it to double your email list or anything like that.
Nate Broughton: 00:38:57 We’ve kind of brainstormed somewhat similar. You get ten extra points, votes, entries whatever and then you get a few more for liking us on Instagram, et cetera.
Brian Kidwell: 00:39:05 We’ve tried out a few different products. We’ve used Viper, we’ve used King Sumo and now we’re using Gleam. We’ll reward people for all kinds of stuff. Go check us out on Facebook or go look at our Facebook community or go follow us on Twitter. We started a Spotify channel just because we could and now we have like 12,000 followers on Spotify because we put it into our giveaway thing. It’s just another way to connect with the brand wherever your audience is and hang out with them and make them more excited about what you’re doing.
Nate Broughton: 00:39:35 Have you ever done a co-marketing thing with someone else who had a list. Where you went to them and we’re like, let’s do this together. We’re at the bottom of the heap here with Opt Out Life Currently, so I’m curious … I’ve been asking some of my blogger friends with lists, some of my friends who have course businesses, what’s a compelling offer to take to someone or is that really even a way to go?
Brian Kidwell: 00:39:55 There is a tool called Dojo Mojo. That is a giveaway tool. Essentially what you do, is you reach out to other brands and together you put on a giveaway. Every single person that enters that giveaway, their email will be distributed to all of the brands that are involved. So as a business, it is very helpful. As a subscriber, you’re kind of annoyed because you just got signed up for five email lists that you may have not wanted to be involved with. We stopped doing that because we would bring like 80,000 subscribers to a giveaway and some of the partners would bring 10,000 and it just wasn’t worth it to us to do that to our subscribers anymore. We didn’t feel very good about it so we stopped that very soon after starting it.
Nate Broughton: 00:40:44 Yeah that makes sense. Low quality subscribers and not a tit for tat scenario.
Brian Kidwell: 00:40:49 That’s thing too, a lot of the people that enter the giveaways, their not going to have the same LTD or their not going to be as excited about your product as the people that heard about you from their friend. If they are and then they tell their friends, then that’s where the real value is. Just spreading that word of mouth any way that you can is what we found helpful with the giveaways. Our current subscribers love it. It’s a free trip. It’s great.
Nate Broughton: 00:41:12 One thing that I’m curious about with you is you’re in the travel space, you have a huge audience, I’m going to call it an audience, you’ve got great reach with travelers. We’ve talked about conceptually there being threats to the business that you, I’m sure come up with many and nothing’s happened yet. The longer you’re around the longer you’re probably going to be around. You know what you do.
Nate Broughton: 00:41:32 I look at someone like the Points Guy or a TV personality like Anthony Bourdain, they’re brands in the travel space and they put out a lot of content. They invest in creating this whole world of travel. Have you guys done anything to become like a travel channel, so to speak? You’ve got the reach. You could send an email out and it would touch every part of the globe. You could get your guy in Bangkok, your guy in Sydney, whatever. It’d be an administrative hassle but there’s the potential there to ignite something that would change your business to the point where you’ve got more of an asset, I think. If you got all this content or guides or whatever. Is that something you guys have talked about? Do you see it as an opportunity, a hassle, I don’t know?
Brian Kidwell: 00:42:20 It’s a massive opportunity and something that we have talked about and thought about a lot. Have not executed on yet simply because we have other priorities right now. We’re just trying to knock those off the list but that’s coming up very soon. We do want to publish content. We want to do it in a unique way. The Trip Advisor’s of the world are great for finding out things that are common and popular to do. That are highly rated and that’s very helpful but as a traveler, the more you travel, you don’t necessarily want the same experience as everybody else.
Brian Kidwell: 00:42:55 For us that’s asking the question of, what’s the one thing that you did in Barcelona that really made your trip that you haven’t found other people talking about. That’s the kind of information that we try to provide to our subscribers in the emails of the travel tips section. We just say, “Hey, if you’re going to go here, you should check this out.” It’s those unique pieces of information that, yeah maybe we’re not making commission on a tour but that’s fine for us because we have a subscription model. We want to provide value to our subscribers any way we can and it’s those unique experiences that I think will do it.
Nate Broughton: 00:43:31 As we tend to do sometimes Dana, we are nerding out a bit with our guest on the topic of choice today. It’s not wine, it’s travel. I think there’s a greater swath of people that are into travel and probably don’t mind us talking about not only the mechanics of what happens at ScottsCheapFlights but some of the fancier ideas of becoming a content distributor and guide maker. Brian’s telling us about how ScottsCheapFlights could potentially someday produce special guides that only highlight that one thing that happened on the trip that you never forget. That’s compelling and I hope they do that. We’re big fans of travel.
Nate Broughton: 00:44:08 I know that you and I have been working pretty hard on something called the Opt Out Life blueprint, which is going to be our first product, our first course. Brought to you by the Opt Out Life. There’s a big section in there, several of them actually about travel hacks. Our best travel stories where we’re not only inspiring people to travel because I think it’s an important component of living the Opt Out Life but also just living a life that’s full of experience and an understanding of what’s out there. We want to encourage people to travel but also in the blueprint we want to give them some tip, tricks and hacks. Some instruction on how we’ve done it and hopefully save some people some time and money as they head out there to do it.
Dana Robinson: 00:44:48 This is actually sort of a commercial break in isn’t it. We’ll work on some actual commercials with some sexy music. The Opt Out blueprint is coming soon. We’ve got a link on the website to get on the list so that you know when it comes out. We’re going to charge something for it but we think we’re going to have, at this point, about 14 hours of audio slides, video content and a bunch of cool resources. A big section of that is dedicated to travel so hopefully it’s something that our users want.
Nate Broughton: 00:45:16 I think they’ll enjoy it. It’s an extension of the podcast which is an extension of the book. Dana’s book is out now on Amazon.
Dana Robinson: 00:45:22 Double commercial.
Nate Broughton: 00:45:23 Double commercial. That book Opt Out, we finally have something to give you. Seriously the Opt Out book was a genesis for all of this and it starts with a travel story. Dana’s travel story to Bali and that’s also part of the Opt Out blueprint. Also on there is how I travel with kids which I get asked all the time. Thank you for allowing us to do a little self promotion at this point on this travel episode. Head on over to, get on our email list, we’ll let you know when the blueprint drops, like Jay-Z.
Nate Broughton: 00:45:52 I know a friend who had a travel community, it’s called BootsnAll. We should interview them by the way. I think they eventually kind of pivoted to having a round the world flight booking engine of some type. Is that an opportunity for you guys? Where the flights end up getting booked through you or does that not actually work with the model at all?
Brian Kidwell: 00:46:12 It could and we’ve definitely thought about it. I think the issue there is the cheapest flights are often on different OTA’s or Online Travel Agencies. The big ones are Orbitz and and places like those. Oh, for hotels but that’s just an example of an OTA. We could do that, but our concern if we were to do that would be that we weren’t always offering the cheapest flight and that we were trying to get them to book through us. For us, our customers are already paying us. The money you make on selling a flight is not that great and we’ve just decided it’s not worth it at this point in time, to go down that path. I mean, Google flights is great. The search is great, it has a lot of information and that’s how we find the flights. There’s other smaller OTA’s that offer better deals and we can send our subscribers there and they can book wherever they like and save the most money.
Nate Broughton: 00:47:12 I like how you guys are holding true to the core of what it is that you do and thinking about your subscriber experience and not chasing after these highfalutin entrepreneurial ideas. It’s not easy, especially at a young age, ’cause you don’t have all the failure experience that I have. Dana’s a whole nother decade beyond me. You don’t have as much stuff to look back on and you seem pretty wise about that stuff. I think you guys are going slow and being smart about making these decisions ’cause, I’m just the idiot here that’s acting like a fake investor saying why don’t you do this stuff. Anyone can propose that to you and these our ideas that someone that would try to acquire you would do and they would fail probably. It’s cool to hear you hold true to, this is what we do, we’ve been thinking about that.
Brian Kidwell: 00:47:53 There’s the balance. You want to grow but at the same time you don’t want to undermine your core business and there’s a lot of things that we could do to make a little extra cash. We have these flight companies emailing us trying to get us to put their links in our emails so that we can take a commission of it. We’ve always said no because we will be better off in the long run if our subscribers trust us and that we’re sending them to the best place for the actual deal. We’re missing out on making money but I think that’s very short term thinking. In the long run I think we’re going to be a more successful company by doing what’s in the best interest of our customers and subscribers.
Dana Robinson: 00:48:36 Yeah, I think it’s brilliant to just listen to this discussion because it’s a place where many entrepreneurs are dashed on the rocks of immaturity. There’s so many cool things you could do, you’ve got a million subscribers. How do you monetize that and it can ruin a business trying to expand or pivot or you lose your identity or you do that thing that looks like it’s going to make you an extra million dollars a month and then you ruin the underlying business that you’re in. There’s not very many entrepreneurs that can keep focused entirely on that core competency because it’s so easy to be dazzled by a shiny new toy of what you might be able to do next or what you can do with where you’re at now. Yet, there’s growth right.
Dana Robinson: 00:49:21 You do have to be stepping back and thinking, how do we continue on this path, leverage the strength we have. You do never know when some major event is gonna thrash you in some way as well. You talked about you’re pleasantly surprised you’re still in existence. We all sort of feel like that in some of our ventures. Nate and I refer to the Opt Out life, once you have some side-gigs and businesses going you sort of feel like how do I keep this charade going. You feel a little bit like that when you have a business that’s succeeding.
Dana Robinson: 00:49:53 You feel a little bit like when you’re a kid and you put on your dad’s jacket and pretend like you’re going to work. You feel a little inadequate. When you’re an adult and you have a business that working, it can be empowering for sure but it can also feel a little bit like imposter syndrome. Where you’re like I’m not entitled to this and when is it going to go away. When is mom going to take my toys and tell me it’s time to clean up and go to dinner.
Dana Robinson: 00:50:17 You’ve got to prepare for the possibility that your business takes a turn. The systems you’re using change, cut you out of their API, telezap your system, no more access. Having those plans for other strategies is still wise.
Nate Broughton: 00:50:35 The business itself, you mentioned you have 30 employees ish.
Brian Kidwell: 00:50:38 Ish yeah, we have like 30 … They’re not all employees but contractors, employees all around the world.
Nate Broughton: 00:50:43 That’s all entirely remote?
Brian Kidwell: 00:50:44 Everybody’s remote, yeah.
Nate Broughton: 00:50:45 How could it be anything else with ScottsCheapFlights. Tell me a little bit about your situation because you mentioned that you traveled for a year and then you came back and this kind of happened. I know that you’re currently living in Austin but you also spent more time abroad later in the story, right? You were in Bali, Thailand, Vietnam, what was that? That was while this was going on?
Brian Kidwell: 00:51:07 Yeah. That was when we were all getting it started. I lived at home with my parents for about nine months and I told them, you know when I got back from my backpacking trip, I was like, “Hey I’m going start a business or get a business off the ground. I’m going to move to Southeast Asia after that.” They didn’t understand it and I didn’t fully understand it either but it sounded like a good idea at the time. I knew Southeast Asia was cheap so I was like, this is the play. That’s what I did. I stayed at home for about nine months. Didn’t leave my room and worked way too much. Then, I moved to Southeast Asia. I was in Bali for two months.
Dana Robinson: 00:51:42 Is that where you started?
Brian Kidwell: 00:51:42 Yeah, I started in Bali. I got a cheap flight out there, 460 dollars from San Fran. Then I moved to Vietnam, I was in Ho Chi Minh City for three months. Love that place. Absolutely insane. The first month I didn’t like it and then …
Nate Broughton: 00:51:59 I was going to say, Vietnam was one that I had such high expectations for and I still have a bad taste in my mouth.
Brian Kidwell: 00:52:05 How long were you there for?
Nate Broughton: 00:52:06 Nine days.
Brian Kidwell: 00:52:07 Okay. Yeah it took awhile for me.
Nate Broughton: 00:52:09 You gotta get with the flow of it. It’s got a different movement to it. It’s a sea of bikes and I don’t know, I could see where it would take a while to get used to it.
Brian Kidwell: 00:52:18 Yeah. Then once you get it, you’re like, this place is great. The foods awesome and the motor bikes. You’re not afraid to cross the road anymore. It’s great.
Dana Robinson: 00:52:29 Talk a little but more about the mechanics. You went to Bali, talk about what you did in Bali, where you lived a little bit and move through some of the other places.
Brian Kidwell: 00:52:37 Sure. This was my first time living abroad in this way. When I was backpacking Europe I was doing the hostile thing which is great. Very fast paced. You meet a bunch of people. Now it was time to work so I would get Airbnb’s or go on Facebook groups for the local cities and find people that were renting places. I started in Bali and I went to Ubud first.
Dana Robinson: 00:53:04 It’s in the mountains.
Brian Kidwell: 00:53:04 That’s in the mountains, yeah. Really cool spot. Little town. They have a great co-working spot there called Hubud with an H so it’s like the city name but with an H in front of it. I just had a little place there. It was super cool. It was run by this family. Every morning I would wake up and they’d be, “Hey, do you want breakfast?” I like, “Yes, definitely.” They’d bring breakfast and some coffee. They’d do my laundry and … Every time I left my place, I’d come back and it was just pristine. It was 500 dollars a month or something like that. It wasn’t ridiculously cheap but it was very, very reasonable. I’d go work all day. I’d walk to the co-working spot. It’s on Monkey Forest Road and all these monkeys just hanging on telephone wires as I’m walking to this place. It was a fun experience and just a good place to meet people and other entrepreneurs, digital nomads.
Nate Broughton: 00:54:00 Is that a big part of it for you, interacting with not only the locals, but some of the other people who are living the digital nomad life? Is that part of the draw? I want to be friends with these people and meet them.
Brian Kidwell: 00:54:10 I wish it was more. I’m a bit of a workaholic especially when it was early on. I knew what I needed to do and I would go to a lot of these places and just be heads down for a ridiculous amount of hours. Just trying to figure things out and get it off the ground. When there was events I would go and try to interact with others who are running their own thing. I’m part of a location independent entrepreneur group and so id go to their conferences and meet-ups and find those people that might have a business that’s more successful than ours. Find people that are doing it and not necessarily just starting out, which is fine but just find people that are where you want to be and surrounding yourself with them.
Nate Broughton: 00:54:52 That’s a common tenant of the Opt Out Life and how everyone’s made it work in their own way. Surround yourself with those people, to seek them out and to have a curiosity to hang out with them, ask some questions, provide mutual value. That’s cool that you were getting that while you were out there. The initial description was like, oh you’re in a cool little house and the family is making you stuff. You’re in the jungle with the monkeys, chillin’. You’re actually furthering not only your business but your own career, your own personal network, your own professional network while you’re there. That’s interesting. This was not a meditation retreat.
Brian Kidwell: 00:55:28 Not a meditation retreat.
Nate Broughton: 00:55:29 This was a further my business, grow my skills, grow my network, trip.
Brian Kidwell: 00:55:36 Absolutely. I was out there for nine months in Southeast Asia and I did the same thing in South America. I loved it. The nice thing about being in Southeast Asia, when you don’t have a bunch of phone calls and things to be on, is nobody else is awake. Your business partner is in the US, you have time to just work. There’s no distractions, there’s no slack pinging you all day long, you just go. Heads down and you can get a lot done so that was super nice.
Nate Broughton: 00:56:04 Okay Dana, last break in here. Another part of Brian’s story that was unbeknownst to me. I knew that he had spent some time traveling. Spent several months in Southeast Asia and South America. When I picture him or anyone doing that really, I’m thinking of van life slash retreat. Not working too hard and spending time checking out the rice fields or picking tea leaves or whatever people do over there. Not necessarily just doing that but living the cheap life, working an hour a day, whatever.
Nate Broughton: 00:56:34 He’s telling us that he was over there working pretty hard. Taking advantage of things that I can appreciate. No ones pinging him on slack during those hours because he’s on a totally different time zone. Everybody’s sleeping over here. It’s almost zen from a work experience perspective and I was like, “That’s kinda cool man.” Maybe I need to go over there so I can work not just hang out on the beach. I had no idea that there was this international community of people working at co- working spaces at start-ups from around the world. That’d be a really cool place to network and meet other people. It sounds like he’s in some groups like location dependent entrepreneurs that even have a success metric that you have to hit before you are in those groups. He’s out there hustling and maybe he’s getting the best of both worlds where he can head to that cheap beach in Thailand but he’s doing as much there as he would be here.
Dana Robinson: 00:57:24 Imagine you’re in your 20’s and you want to do a start-up, you gotta pay your full pop in rent in say, San Diego. Your utilities, cable, internet, gas for the car, insurance. Just think of all the costs you’ve got to carry if you’re going to be a boot strappy start-up or starting a side-gig. Whatever you’re doing. Now picture your monthly expenses going down to five or six or seven hundred dollars a month. It’s pretty cool if you’ve got a little bit of side-gig revenue, you can become a digital nomad. The digital nomad community can be segmented a little bit. There are a lot of people trying to break into that and so just like any business, there’s a lot of noise, a lot of people that might take your time.
Dana Robinson: 00:58:04 When I was in Bali, I went knowing that there would be some people working and there was a couple of co-working spaces but I really didn’t know how big it would be and that literally everywhere I went, restaurants, cafes, even bars. Middle of the day when those bars are kind of slow, you’d see a guy on a laptop over in the corner, overlooking the rice fields, working away on their computer, doing whatever their business was. It gives them the freedom to do work and not really be stressed out by the cost of living for a lot of people. At the same time, if you’ve got wanderlust like so many of us do, then you’re out there. You get that cheap flight from Bali to Singapore to China or back into Australia to get around some people that sound like they speak English.
Nate Broughton: 00:58:50 You walk through the trade off that I would think would be there would be, yeah you’re in San Diego, you’re paying for rent, just the living expenses are a lot higher. The trade off to me would be you’d be surrounded by a bunch of opportunity and part of the reason that I love being in San Diego is I feel there’s a lot of other entrepreneurs like me and investors and things like that. There’s an energy to it and I think that would be the argument for places like, San Diego’s probably not even on the list necessarily but, Seattle, Austin, Boulder and Silicon Valley. You’d be paying those American prices to live here, to be around that. What Brian’s telling everyone and that your reiterating too is that there’s an energy and a community in those places too so the trade off is not necessarily as great at least in the way that I perceived it before we talked.
Dana Robinson: 00:59:38 Think of the story of how he met people that he ended up traveling with as well. You could be a solo traveler and end up with a crew that has some symbiosis. You’re doing similar projects, you’re learning from them the same way we do when we’re networking and hanging out with people that do internet marketing or programming. You’re meeting that same kind of crew and they’ve got the same spirit. They’ll be like, ” Hey our Visa’s running out here, where are you going next?” You might find yourself in the Himalayas in a co-working space.
Nate Broughton: 01:00:05 You’re running out of excuses man. I don’t know why not to do this? Hopefully we’re compelling some other people to explore it some more. There really is this growing wave of people online. Call them digital nomads, call them location independent entrepreneurs, call them whatever acronyms or labels are there for these people. You go out and you try to find blogs and there’s hundreds of them. I’m trying to navigate them myself, to shuffle through the noise and find out who’s putting out good stuff.
Nate Broughton: 01:00:32 It’s definitely a trend and Brian’s got a business that’s travel related but even more so than that, if you kind of take that for what it is. He’s pulling off this kind of digital nomad entrepreneur thing and it doesn’t even matter what he’s necessarily doing. Let’s celebrate what he’s been able to do with his lifestyle and his approach to it which I think is kind of unique. He lands there, he’s ready to work had and then he’s hanging out at these networking events and meeting other people who are doing similar businesses. He’s actually … He’s not giving up anything as an entrepreneur by being there. I think it’s actually enhancing that and that is something that I think people should appreciate. I know I am.
Brian Kidwell: 01:01:15 After Ubud, I went to Canggu and I stayed at this little surf house place. It was so cool. I could just grab my motorbike, ride two minutes dow to the beach, rent a surfboard for three dollars, go out there for two hours and then go back to my place. There was another great co-working spot there. Just a really, really cool community out there and very, very relaxed which isn’t necessarily what I was looking for but it was nice.
Dana Robinson: 01:01:43 Yep, Canggu’s young. Lot of hipsters. A little bit of attitude from those Aussie’s that where no helmets.
Brian Kidwell: 01:01:53 Yeah, Canggu is like the Cancun for Australian’s. That’s where they go to party.
Dana Robinson: 01:02:00 Yeah, great surf break at Old Man’s. Echo beach. Cool stuff. So you’re two months in Bali.
Brian Kidwell: 01:02:07 Yeah two months in Bali and I would decide when to move when my Visa would run out.
Nate Broughton: 01:02:11 I was going to ask, did you plot it out or …?
Brian Kidwell: 01:02:15 No. I just had the flight to Bali and then …
Dana Robinson: 01:02:17 You have to renew your Visa at 60 days by leaving the country anyways. So you could leave, stamp out, go to Singapore for a minute. Have a burger and then fly right back. You get another 30 plus a renewal so you get 60 or you could do what you did and just stamp out and stay out.
Brian Kidwell: 01:02:36 Yeah. I thought there was a lot to see so I didn’t want to stay in one place without exploring a little bit more. The next spot was Vietnam. I stayed in Saigon for three months. Just a great time. I love that place. Just riding around on a moped and it’s not weird over there, like in the US. That’s fun. I moved to Thailand after that. I stayed in Chiang Mai for four months with some trips to Phuket and the islands. Once again, I had a crew out there this time so this was a lot of fun. We all had our motor bikes. We’d just go on these rides through the mountains and it’s awesome. Great little community out there in Chiang Mai. A lot of people just trying to get their stuff off the ground. Just starting out for the first time but there’s definitely a thriving community and events that you can go to. A lot of fun out there as well.
Dana Robinson: 01:03:27 Did you meet the crew there or did you connect with other people from your digital nomad network and were like, “Alright, we’re all going. Thailand. Let’s do it.”
Brian Kidwell: 01:03:36 I had a buddy that I met in Vietnam at an event and he worked for a company that would meet up every quarter at a certain part of Southeast Asia. That quarter they were all in Chiang Mai while I was there. They were all there for a month and it was a fun group of guys. We would go out and have a good time. It was kind of serendipitous but it worked out really well. It was nice having a community. That’s one of things that sucks when you’re out there, especially if you go by yourself, is the community aspect. It definitely wears on you over time if you don’t have that social interaction and other people that you can go have fun with.
Nate Broughton: 01:04:14 There are a lot of digital nomads these days. There’s a whole universe of those people out there and there’s another universe somewhat parallel of mini-retirements. Their kinda doing the same thing but maybe it’s only for a certain period of time. Maybe the two overlap a bit. Coming to them as we start to think about where does the Opt Out Life overlap with other trends and audiences out there. Are there some digital nomads … You mentioned you’re in some groups, are there groups we should be paying attention too. People we should follow you think that are kind of leaders of that pack. I’m curious.
Brian Kidwell: 01:04:47 I think Dynamite Circle is a great group. They … I always laugh at the name. It’s not the best name but it’s a great group of people. You have to have a certain level of business to be a part of that group. There’s that threshold that you have to meet before you can interact with all these people but once you’re in, they have conferences throughout the year. Kind of a TedX approach as well so other people in the community can put on conferences throughout the world so these are always going on. Every October they have what’s called DCBKK, which is this great conference in Bangkok, they take over the Conrad Hotel which has a pillow menu so you can select what kind of pillow you want, it’s ridiculous and it’s reasonably priced. It’s fantastic.
Dana Robinson: 01:05:31 I love this because a lot of people think … There’s two contrary opinions of South Asia. For example there are people that think that Bali is only luxury hotels because if you follow models and stylish people they only post those pictures. Then when you get off the airplane and you get pestered at the airport and you finally get into a taxi, you feel like you are driving through a war zone in some places. It feels a little Tijuana. On the flip side, some people think, well digital nomads, staying in huts with monkeys and yet you might find yourself at the Conrad with a menu for your choice of pillows. When you get your massage they let you choose amongst a dozen different scents and oils.
Nate Broughton: 01:06:15 I think the perception even mine, it’s very solo style and you tell me about all these communities. I know that they’re there but I didn’t know that they interacted so much. That’s pretty cool. As you mentioned, it would get kind of lonely and shitty if you were somewhere for 30 or 60 days and didn’t really have a social network there to plug in to. It’s different then what a lot of people think in a lot of different ways.
Dana Robinson: 01:06:37 Like the phrase that’s becoming popular, location independent.
Nate Broughton: 01:06:42 Isn’t that the name of one of the groups, location independent.
Brian Kidwell: 01:06:47 That’s their tag line. We’re location independent entrepreneurs.
Dana Robinson: 01:06:52 It captures a lot more than just … Digital nomads I think started as a phrase for people working. Doing their side-gig. We talk a lot about side-gigs. In the US you can have a side-gig but it’s probably not going to pay all your bills unless you want to be really boot-strappy. You can take that same side-gig that’s throwing off two grand a month, and you can go do anything you want for an indefinite period of time in South Asia. Enough people have figured that out.
Dana Robinson: 01:07:20 I met guys that were doing gambling. They were professional, they would play poker for two hours. They’d make their 40 bucks or whatever their par was for the day and then I’d see them at the cafes. There just like, “Yep, made my money for the day. Doing my thing.” There’s guys that were freelancers. Women that were designers. At the same time you have people who are doing these mini-retirements. People that are doing one month, tow month stays that might not be working that hard but they’re fielding their business back home while they enjoy the good life some place that’s inexpensive like Bali or Thailand or Vietnam. Kind of a cool, eclectic community that aren’t all in the co-working spaces with their head down in the computer. Sort of spread across a whole bunch of goals and opt out lives.
Nate Broughton: 01:08:10 To hear that there are these cool co-working places. I envisioned you on a laptop just in a lobby somewhere or a coffee shop. You’re changing my perspective on this stuff. It’s pretty cool.
Brian Kidwell: 01:08:19 The classic digital nomad image. Just some dude on a beach with their laptop and you’re like, no that’s not it.
Nate Broughton: 01:08:25 So, you’re in Austin now. What’s on the horizon for you, not necessarily professionally but where you going to be? Are you going to be there for a while? It depends on what email comes.
Brian Kidwell: 01:08:36 No, yeah. It really does. I went to New Zealand recently which was really fantastic. I’d like to get back out to Europe, I haven’t been there for a bit. I like to get out to Tokyo. Basically just waiting for my cheap flight to arrive and I’ll take it.
Nate Broughton: 01:08:51 I like it. You mentioned that your parents thought, I don’t know if you said it was crazy or they really didn’t understand, that you were going to go over to Southeast Asia. Tell me a little bit more about that? Was that all is was, they were just like, “Well, you’re an adult now, go figure it out.”
Brian Kidwell: 01:09:06 Yeah.
Nate Broughton: 01:09:07 That was pretty much it.
Dana Robinson: 01:09:08 Or were they like, when are you going to get a job and get a respectable life and buy a house?
Nate Broughton: 01:09:14 This travel email thing, what’s wrong with you. You just went to college and invested in that education and now you’re going to go vagabond in Southeast Asia again. Tell us a little more.
Brian Kidwell: 01:09:25 Yeah. You guys kind of hit it on the head there. When I got back from Europe, my parents asked me what I was going to do. My whole time in Europe I was like, “Ya know, I’m going to go out there. I’m going to think about what I want to do and I’m going to come back with a plan.” On the plane back I was like, “I have no idea what the hell I’m going to do.” So, my parents asked me that question and the best response I could come up with was, “I’m going to get a business off the ground and I’m going to move to Southeast Asia next year.”
Brian Kidwell: 01:09:55 For some reason, they were okay with that. They let me crash at their house, which was very nice of them. That’s the thing of entrepreneurship, there’s not just one day where everything magically happens and you start making money. It’s this constant process of slowly growing. Every day my dad would come home from work and he’d be like, “So, did you make any money today?” I’d be like, “Nope, no money today.” I was working towards something so that compound interest, principal, it just takes a lot of time but once it has momentum it really starts to take off. I don’t think they really got it. Why I wanted to go out to Southeast Asia. I didn’t have a great reason, I just said, “Hey, there’s digital nomads out there. I’m going to find other people doing this kind of thing and do it.” I was just resisting getting a job for whatever reason. I felt like I could pull something off and just kept trying and trying and trying.
Nate Broughton: 01:10:53 Have you ever had a job, a regular job?
Brian Kidwell: 01:10:55 I worked at K-Mart in high school.
Dana Robinson: 01:10:57 I didn’t know K-Mart was still around.
Brian Kidwell: 01:10:59 Well not anymore I don’t think.
Nate Broughton: 01:11:01 It’s your fault.
Brian Kidwell: 01:11:02 Yeah, I left, they shut down.
Dana Robinson: 01:11:05 K-mart. I remember going there as a kid and it was the place you never wanted someone you knew to see you. It had cool stuff but as a kid you just know that this is the cheap place that I shouldn’t be caught by friends at school.
Brian Kidwell: 01:11:19 It’s like a bad Wal-Mart.
Dana Robinson: 01:11:21 It is. It’s like below Wal-Mart.
Brian Kidwell: 01:11:24 I was always a hustler growing up. I’d put flyers out there, give out business cards. Like, I’ll wash your car. I’ll mow your lawn. I’ll rake your leaves. Whatever, I’ll do it. I just wanted the work.
Nate Broughton: 01:11:35 That was just in-born in you. Was your dad entrepreneurial at all?
Brian Kidwell: 01:11:38 No my dad’s an engineer. He’s like the last thing from an entrepreneur. My mom’s a bit entrepreneurial. It’s kind of weird. I’m the odd one out.
Dana Robinson: 01:11:46 Have the folks accepted your role now that you’re successful or are they still waiting for you to get a real job where you have to wear a jacket to work.
Brian Kidwell: 01:11:55 Fortunately, my parents have seen what I’m doing and accepting of it and happy for me. Other family members, they’re still wondering when I’m going to get a real job because they probably think I’m just living off my parents dime or something. I don’t know, I don’t care anymore.
Nate Broughton: 01:12:07 We talked about that a little on the podcast and also in our course. The social pressures that can be there. It sounds like you are in a pretty good situation with that actually. It was good to get more of the narrative. Even the people outside your immediate family or friends, I think it’s hard for them to understand what you do or what we do and sometimes that’s annoying. Sometimes it’s only the conventional markers of success that make them be like, “Oh, Brian’s successful.”
Nate Broughton: 01:12:31 I tell the story of when I was 23 I got this fancy car and they were like, “Holy shit, I didn’t know you were doing so well.” It’s like, “I’ve been doing well man. I didn’t even really want this car but I guess now everyone thinks I’m successful.” It’s a weird thing. It was giving me validation that maybe I subliminally wanted or appreciated do I didn’t have to explain it anymore. That was thing and I’m like, so stupid.
Dana Robinson: 01:12:56 Social pressures are completely out of wack with what it means to be successful.
Brian Kidwell: 01:13:02 Yeah its strange, once you’ve had some success you stop caring as much about what other people think. Then you like, “Well, if they think I’m bummin’ off my parents, that’s their decision. I’m doing just fine, thank you.”
Nate Broughton: 01:13:17 Really the success as you define it and as we define it with the Opt Out Life is freedom. Freedom to travel around, to be in control as much as any of us can be of our financial destiny by owning your own business. That’s really what we want. That’s the currency that we want and the social pressures be damned. I can do whatever ’cause I own my own business. I can live where ever I want. You win.
Brian Kidwell: 01:13:44 Yeah, man. I miss San Diego so I cam out here for a month.
Nate Broughton: 01:13:46 Yeah we haven’t even talked about that. It’s beautiful.
Nate Broughton: 01:13:51 Thanks again for listening to the Opt Out Life podcast. If you like this episode or any of our episodes, we’d love to have you as a subscriber. Click the subscribe button on iTunes or wherever you get your podcast. Then, head over to, there you can enter your email address to get on our email list so you’ll be the first to know about new podcast episodes as they come out. Including hand picked highlights, links to resources we mention and top quotes from each episode.
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