Adam Dailey – Man on the Run (Around the World) – Opt Out

Adam Dailey – Man on the Run (Around the World)

2 years ago · 1:22

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We call this episode “Man on the Run (Around the World)”because our guest Adam Dailey does exactly that.  He’s a former college athlete who turned his access to Olympic event tickets into the ultimate lifestyle business, selling travel packages to big events for over a decade.  It saw he and his (fellow athlete) wife live in beautiful places from Spain, to Greece and Italy, to London, Vancouver and San Diego.

But that’s only the beginning of Adam’s story.  As his young family grew in size, and the financial success grew, Adam took a big risk on the 2012 Olympics in London.  He set a goal to make $10 million in revenue on that single event.  As we learn, it did not turn out as planned.

Post-London, Adam started to feel burned out.  The “opt out life” he was living as an entrepreneur and business owner in the event industry lost its luster.  So he makes a crazy plan to step away, put his family’s possessions in storage, and travel around the world for 1 year (with 4 kids!).

Not crazy enough?  You won’t believe what happened to Adam in the months leading up to his 1 year sabbatical . . . and it takes place in an office stocked full of cash, hundreds of thousands of dollars in event tickets, in Copacabana, Brazil.  This story is just one of the many that we recount in this episode, and that are featured in Adam’s best-selling book, How to Run Away From Home (And Bring Your Family With You).

Adam tells us about his successes, failures, and how he hacks together a lifestyle living in La Jolla, CA while still traveling several months per year with his large family.  He’s an Airbnb “master”, has a passport full of stamps, and a unique outlook on what it means to live your life now and not when you’re 65.  Enjoy!

Highlights from Episode 7 with Adam . . .

On why he decided to take a year off, and travel the world with a family of 5. . . The whole thesis in my head was I’m spending so much money in this life I don’t really enjoy day to day. And so I was taking home 10 grand or something a month type of thing after taxes and I’m like if you gave me 10 grand next month on May first and said here’s 10 grand in cash what you want to do with it? This would not be my choice. I would not be living where I’m living, driving to what I feel like as a job, stressing out about this, stressing out about that. So I was like what would I do? The default is I go travel. If I had 10 grand a month in cash at the beginning of the month I could live like a king for 10 grand. So my whole hypothesis was that I bet I can travel with my kids and still spend less than I was traveling home.”

Recounting the story of being raided by cops in Brazil, and having his business partner and employees put in prison . . . I didn’t feel like it was fantastic at the time but yeah I mean basically we got raided by police in Brazil for what they called racketeering which is basically organized crime, which wasn’t true but it didn’t really matter. And so we threw a bunch of money at the problem and they came back and arrested basically two of my employees, one who was like basically my best friend and threw them in jail as well. So I was on the lam for a fact in Brazil and then it was a gnarly feeling. I’m not going to lie, it was one of the worst feelings I think I’ve ever had in terms of not only are your friends incarcerated but you’re also running the biggest to this day probably the biggest event I’ve even been involved with. It was bigger than London in terms of revenue and clients and whatnot and I took three key people out of the event who were basically running the event for me.”

On why he travels, because being “uncomfortable” is ok . . . “Because that’s what makes the story memorable. You’re never like, “Man, we flew into Cabo and went to stay at this resort for like two weeks, and that was like… Man, I’m still talking about it.”We’ve got to do those things, I guess, every now and then but that’s a resortist, not really a traveler. Those memories don’t really stick out. So I think the best stories are being uncomfortable and to this day, the best stories you’re going to tell are probably some problem, right? Some issue you had and you came out ahead. It all worked itself out, right?

More on travel . . . “I also think that it’s really easy for us to be very ethnocentric and for me, I love Europe because you can get on a 60 minute flight and have a country with hundreds of years of different history, with a different language, with different food and it’s such an amazing place in that way. And so for me, it’s that culture. And for us, it was really about teaching our children about these cultures and even if our kids don’t remember Greece, they might, somewhere deep in their chip go, “I remember somewhere people speak other languages,” right? I remember houses weren’t as nice or whatever they want to remember. And I think especially with the way things are now with our world, it’s important to think outside of your little bubble in La Jolla and go, okay, there is a bigger world out there and there are other things out there.”


Nate Broughton: This episode of the Opt Out Life podcast recorded here in San Diego, the Opt Out Life story of Adam Dailey.
Dana Robinson: Welcome to the Opt Out Life podcast, the No B.S guide to living a modern good life. Hosted by subversive millionaires Dana Robinson and Nate Broughton, the Opt Out Life podcast explains exactly 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.
Nate Broughton: In June 2014, Adam Dailey narrowly escaped arrest and imprisonment after his office was raided by crooked cops in Copacabana Brazil. As he received frantic phone calls from his employees, Adam took a moment to write down his recollection of the raid in his journal. Who is this international man of mystery? Why is he here on the Opt Out Life? There is of course a story. You’ll have to listen to hear how it ends.
Dana Robinson: Mystery aside Adam truly is a man on the run around the world. He is an entrepreneur, speaker, investor and bestselling author. He’s had a fascinating life that has brought him from an early career as an athletic runner to running a business selling travel packages to Olympic Games, World Cups and other massive international events. His foray into this business was on a whim, when he uses access as an athlete to purchase tickets to the Olympics in Greece in 2003.
Unsure of the next step, Adam and his wife moved to Athens and then set up shop. He found success in Athens and then parlayed what he learned into a decade plus run of events that included stints in Italy, Spain, England, Canada and eventually San Diego.
Nate Broughton: Adam is author of the bestselling book, How to Run Away From Home: And Take Your Kids With You. It’s the recounting of his journey both as an entrepreneur and as a vagabonding family man who decided to sell everything to take his wife and four young kids on a yearlong journey living around the world.
Dana Robinson: You might think Adam is just another rich guy who got paid millions from selling a company. He’s rehabbing a big house in an expensive zip code. He spends his days doing what he wants when he wants and he travels around the world on a whim. He’s got rental property and even a hotel project, but Adam’s story shows that the Opt Out Life is what gets him his lifestyle. He rents out his house on Airbnb to pay for his travel. And he also has used Airbnb to create passive income from rental properties.
He hustles for free airfare using air miles and he waits until the last minute to book rooms at steep discounts. These are the tools of the trade for people who opt out and opting out gives him the freedom to work on business projects that get him excited to go to work every day or to take off again to go travel around the world for another year.
Nate Broughton: Let’s hear the story of the man who runs around the world. Okay Adam well, thanks for making the drive down from La Jolla to be here today. Adam is a resident here of San Diego as many of our early guests are but he is a man about the world whose passport definitely trump both Dana’s and mine combined. So I said I’m excited to talk about travel and we will get into that.
Yeah first off, Adam tell me where you are today. You’re living in La Jolla, we met up two weeks ago and had coffee to catch up and I think we originally met about five or six years ago when you had your, had Lotus Tours the tour company and take a business. So we’ve got some shared history there but you seem pretty happy there. Isn’t a panic kind of at 8:15 after dropping the kids off La Jolla Elementary? I think you’re living the Opt Out Life pretty nice right now up in LJ.
Adam Dailey: Yeah I have five little kids, so I spend a lot of my mornings getting them ready, getting three of them out the door at the elementary school there. Another one nearby and try and have coffee meeting on a daily basis right after that and then jump into all the different projects I’m working on which seem to vary day by day, but yeah I mean, there’s not one thing that’s driving me, unfortunately or fortunately depending on how you want to look at it. The focus is on a bunch of different projects now and still travel a good bit and still trying to figure out kind of the next big play if I can do that.
Nate Broughton: Right and you’re heavily involved EO too, right?
Adam Dailey: I am yeah. I’m doing the learning this year and then I’m president elect for I guess this next following year.
Nate Broughton: Oh dang okay. And the learning means that you kind of tell me get to mess with the budget and bring in the guests and speakers and all that.
Adam Dailey: Yeah I get 300 grand just to throw cool events for the year. So it’s pretty fun and that’s kind of my background is throwing cool events and my focus this year has been kick ass speakers slash events without spending money on venues. So we’re doing really out of the box stuff with Tucker Max and Sean Spicer and Lance Armstrong and just guys that you wouldn’t think of as, we had Ryan Leaf last week, the guys are not inspirational business speakers but are like, well people like “Well what’s interesting I want to go check them out.” So it’s been a pretty fun year for that.
Nate Broughton: You’re an athlete and your wife was as well right?
Adam Dailey: I was yeah. My wife and I were both All Americans, CWA All-Americans Athletes, the University of Arkansas, Multi-National Championship caliber. We won nine national titles when I was a part of team, the University of Arkansas. My wife was a 12th time All-American and she never got to win a championship herself but yeah, it was a great experience being an athlete and led to a lot of other things as well.
Nate Broughton: And she’s a member of the Hall of Fame?
Adam Dailey: She is. She’s a Hall of Fame member, it’s funny because the women are, in Arkansas they’re great but they’re not to make that team as a guy I might get when I’m 70 years old but there’s I got teammates who made the Olympics won various national individual titles and they’re still on the list you know so it’s a long list.
Dana Robinson: Adam is being a bit modest here but we’ll give him the shameless plug. He’s author of the bestselling book How to Run Away From Home: And Take Your Family With You. It’s a book about how he built that rat race and took a year to live abroad with his wife and four young kids. We dove in with him to get at what drove him to take that trip.
Nate Broughton: So yeah I mean you’ve been a serial traveler with, you’ve had children born abroad. You and your wife had traveled from your honeymoon on forward but one big trip that you went on was as your business was kind of winding down you were having a similar situation as Dana with his book with Opt Out. You decide to go on a one year sabbatical with the kids and the wife around the world and that’s pretty much the plan, right.
It’s like I’m not enjoying working, business is no longer fun. And I think there’s a quote in your book where you said you’re like, “I felt like I was driving to work every day.”
Adam Dailey: Yeah.
Nate Broughton: That’s pretty interesting when it’s a business that you own and you’ve been living for 12 years owning your own thing and having fun. You tell a story about flying to a conference in Florida and feeling anxiety being away from the kids and anxiety about seeing people at the conference that are in the industry. Like it’s seems like a low point where you’re like what do I do? And the solution is to take a year off.
Dana Robinson: Now let me qualify this.
Nate Broughton: Okay.
Dana Robinson: It’s nothing like my trip, because Adam’s story makes me look like a total woos.
Nate Broughton: Yeah.
Dana Robinson: My trip was the kids out of the house, how do I take these six businesses I’m juggling and can them in a way that lets me break free? I didn’t have four kids and a business partner in jail and Brazil. And all of the other tensions and stresses. So for those that haven’t read the book you should read this book especially if you’ve got kids but I just want to interrupt to say that Adam’s my hero and I could never have pulled this off with one kid let alone four.
Nate Broughton: Right. How did you pull this off like just the planning side because there’s some practical tips in there that I think are important to mention here on the podcast because some of them go along with the Opt Out thing? It’s like all right you want to take this one year sabbatical okay well the wife’s got to be on board, one we’ve got to deal with our situation here in San Diego you’re living somewhere. You have a business.
Dana Robinson: House and rental property.
Nate Broughton: Yeah you have rental properties.
Dana Robinson: Furniture’s.
Nate Broughton: Furniture. You get to like check all these-
Dana Robinson: We will say four kids.
Nate Broughton: Yeah, four kids exactly.
Adam Dailey: I mean yeah it was it was a lot of stress into the planning part of it and part of it was you know the whole thesis in my head was I’m spending so much money in this life I don’t really enjoy day to day. And so I was taking home 10 grand or something a month type of thing after taxes and I’m like if you gave me 10 grand next month on May first and said here’s 10 grand in cash what you want to do with it? This would not be my choice.
I would not be living where I’m living, driving to what I feel like as a job, stressing out about this, stressing out about that. Feel like I’m a limo driver for my kids and then there’s nothing left in terms of money at the end of every month. So I was like what would I do? The default is I go travel. If I had 10 grand a month in cash at the beginning of the month I could live like a king for 10 grand. So my whole hypothesis was that I bet I can travel with my kids and still spend less than I was travelling home. And I didn’t know what I wanted to do.
I mean I knew I wanted to take a year off but I just, I knew I needed a break and I knew I needed a career change but I knew if I just sat at home I’d be stressed about the mortgage and I’d be stressed about paying the kid’s daycare or whatever. I mean we were spending whatever it was, I think of $3000 a month long childcare between daycares and nanny and all this and so it just was all adding up. So for me it was like well if I can go spend the same amount and be living in Costa Rica, in Spain, in Australia, at least I’ll have a world experience out of it.
The thing I did that might have been a little different than most people, is I did it without I mean I had some side hustles but I did it with full knowledge that I am going to have less money at the end of this trip than when I started. And I think that Tim Ferris genres like build this all, money while you sleep passive and I love it I’m not knocking it. It’s just that wasn’t where at. I was like my net worth is X. And my net worth will be less than X when I’m done and I’m okay with that because why make all this money if you can’t take a withdrawal every now and then?
I’m not my parents and I think that was my parents’ generation is like work work work, in every parents’ generation and when you’re 65 baby live the good life and you can go on cruises and you can do all kinds of cool stuff when you’re 65. I’m like why do it if I’m just going to keep my head down for the next 20 years? I worked hard I should be able to take a withdrawal.
Nate Broughton: Alright Dana, I love what Adam is saying here. He’s just thrown off one liners that could be bullet points on our website, that are almost like coming out of the Opt Out book or are coming from other podcast episodes. He’s telling us why he decided to take a break from the life that he had built here in San Diego and with his business and take a year off and sell all his stuff and take his family and live around the world. And yeah he’s someone who’s been comfortable owning businesses and living in international cities but it’s really more the mindset of like he’s saying things like I’m driving to work and I feel like I’m going to a job.
Dana Robinson: This is a business that he owns as well. This is a great gut check I mean just being an entrepreneur, just being a business owner doesn’t get you the life you want which is why we’re calling this the Opt Out Life. I mean we don’t believe that owning a business is the end. I mean it’s the means to an end.
Nate Broughton: And he also talks about how he’s making decent money too. He’s taking home 10 grand a month after taxes. That would make a lot of people “happy” and feel like they could live the Opt Out Life, but it’s not creating that happiness for him. He’s like you know what else could I do with this 10 grand a month? He talks about where it’s going, three grand a month to childcare, and a bunch of it towards a mortgage in a place that’s not making him happy.
Dana Robinson: Yeah and what a great analysis to step back and just objectively say, “Boy if someone said I’ll give you $10000 to do that again, he wouldn’t do it.” He could think of a lot of other things to do with that. I mean that’s a great way to step back and objectively look at what you’re doing and to think, “Am I stuck in a rut?” And he knew he was.
Nate Broughton: And also his mindset was of, “If I stayed here and had that same amount of money at the end of the month, I’ve got none left over, what experience of my getting out of it?” And he’s saying, “If I do that same thing and travel it’ll be something that me and my family remember for the rest of our lives.”
Dana Robinson: Yeah there’s a great mental process to go through for somebody that’s looking for the reason, the motivation to make the leap.
Adam Dailey: And so that was a big part of it for me was being able to acknowledge that and of course I still stressed about money during the trip but it was always about can I spend less and I would spent significantly less. And planning the trip took a lot in terms of I did use miles for all the big legs when you’re using miles and booking five or six plane tickets you do have to book decently far in advance. I mean I booked Sydney – Bangkok leg on first class probably 11 and a half months in advance or whenever it was, it was like the first day you could do it and I booked it you know. I think it’s 330 days out.
So that part was tough and then the rest I mean I planned but it was because the way I was trying to do it which was basically at a discount. I had to do a lot of last minute stuff. So I didn’t know where I was staying most of the time more than a couple days in advance, because I was always writing people who are renting a place for 500 bucks a night and asking them to give me a bro deal for a hundred bucks a night. And no one would consider that unless it’s last minute.
So I kind of figured that out early on in the process and we just kind of had our systems in place and I would figure out where we’re staying and how to get there and my wife would kind of figure out when we got there what we’re going to be doing every day.
Dana Robinson: All right Nate, I think we’ve got a break in here because we’re hearing pretty cool story about how the business unfolded for Adam, but he’s about to tell something that happened in the business is pretty dramatic, pretty big obstacle. And I think it’s worth kind of foreshadowing that a little bit for those that haven’t read his book.
He’s at a point where his business is really on its biggest project and he’s down at the World Cup in Brazil. He’s got several employees, his partner working with him. They’ve got bags of cash tens of thousands of dollars in cash and hundreds of thousand dollars as I understand it in tickets. These are tradable commodity so he’s got all this holed up in a hotel room with the staff and they’re hustling, doing what they do for business and he gets this shakedown.
Nate Broughton: Yeah I can imagine how he felt that day. I mean first of all you’re in Brazil and people pop in and they claim that they’re police. You’re not really sure if they’re police and I think he explains that in the book. It would take them a few minutes or realize that these were just criminals or cops or undercover cops and it turns out in Brazil they’re kind of all three. But the story is incredible.
It’s a day where he’s told his partner that he’s getting a little nervous of the cash and the tickets that they’re holding there in the office. They’ve got several employees hunkered down. It’s in the middle of the event in Copacabana these guys come in with guns and they force them to give up the cash. They after a lot of negotiations, negotiate to get Adam to walk downstairs even with them, he didn’t want to go with them. And they put them in handcuffs marched them down the stairs and as they’re coming outside with all the staff, another crime happens right in front of them.
Adam tells a story here a little bit but I certainly encourage you to read the book too after getting this because it is one of most incredible entrepreneurial stories I’ve ever heard. Yeah it is a fantastic story.
Dana Robinson: Can you recount some of the story for us? I think it’s cool for our listeners to hear failure and drama obstacles, the things that hit entrepreneurs, because you’re story is about guys that are making 10 grand a month with the side gig that takes an hour a month and those are pretty sexy. But those same people have had some failures some of them epic, some of them small. Fleeing a country with a partner in jail is pretty fantastic.
Adam Dailey: Yeah. Well, I didn’t feel like it was fantastic at the time but yeah I mean basically we got raided by police in Brazil for what they called racketeering which is basically organized crime, which wasn’t true but it didn’t really matter. And so we threw a bunch of money at the problem and they came back and arrested basically two of my employees, one who was like basically my best friend and threw them in jail as well.
So I was on the lam for a fact in Brazil and then it was a gnarly feeling. I’m not going to lie, it was one of the worst feelings I think I’ve ever had in terms of not only are your friends incarcerated but you’re also running the biggest to this day probably the biggest event I’ve even been involved with. It was bigger than London in terms of revenue and clients and whatnot and I took three key people out of the event who were basically running the event for me.
It was also the month before I was supposed to go on this trip that I’d already been planning and I already knew I was burnt out. I’d already told my board of directors I’m leaving the business. I had my partner who already knew and then my wife’s crying going like are you going to be in jail or are we still going on this trip. Like we just leased out our house, I sold our couch I don’t know you’re not talking.
So it was a pretty horrible mom in terms of everything but it also hit home for me that I have to do this trip. I got to get out of this business like because it’s, the business was sexy, and it was you’re going to Brazil. You have hundreds of thousands of dollars, millions of dollars of ticket and I mean it’s kind of fun the ups and downs but I needed a really bad exit in a way to really kick me out of that industry at the time and that’s what I got.
Dana Robinson: I hate to get all spiritual, but I have this theory that when you’re done with something the universe ensures you understand it very loud and clear and you get that one last ass kicking and it’s like it’s time to move on.
Nate Broughton: Yeah I can’t imagine getting one because of that. We’ll have to either recount the story or send people where they can read it and but how Brazil is it to be like being walked out by police and then get robbed.
Dana Robinson: Right and then they forget to arrest you.
Nate Broughton: Right. I mean that’s so Brazil …
Adam Dailey: Yeah so the guy robbed a bus right in front of us and they beat the crap out of this guy and let me go by accident. That was there. And ultimately we spent hundreds of thousands of dollars bribing judges and cops and lawyers and I don’t want to say it didn’t help. I don’t know if it helped or not but we’re just we’re getting scammed by anyone.
Dana Robinson: Your people got out of jail eventually?
Adam Dailey: They got out of prison and then they had to stay in the country for a couple months to await their trial which was just another scam basically to extract more money and so they finally did. Now they laugh about that experience somewhat. I mean my former business partner still jokes that was like the best three months of his life. Because it was that time and you know because he was cooking every night, didn’t have much responsibility, watching lots of Netflix, eating Brazilian food, like I’m like all right well [crosstalk 00:18:04].
Dana Robinson: The first vacation you had in years.
Adam Dailey: Exactly.
Nate Broughton: No, that’s interesting to hear. Let’s break in here as we get back to the beginning of Adam’s entrepreneurial journey. His wife and Adam were both athletes at the University of Arkansas and they went to the Olympic trials before the Athens Games and through happenstance, he finds out that he has the ability to buy tickets for the Olympics kind of in bulk and he does it. He jumps at the opportunity not really knowing what he’s going to do with them but it just seemed like a good move and I love it because it’s the typical entrepreneurial, I wonder where this could lead and he’s willing to take the leap and buy those tickets.
We’re going to find out that leads him on a 12 to 14 year journey in his career just making that one simple decision, taking advantage of a thing that he had access to just through happenstance.
Dana Robinson: Yeah what I like about this Nate is that he calls this low risk. He calls this investment safe. He says I don’t understand stocks. And for a lot of people you shouldn’t probably just go buy some Olympic tickets but this was his industry he actually knew this and the aha moment for him was hey I actually know all the Olympiads. I know the guys that are all going to be there, their families. So buying these tickets was for him it was safe. For a lot of people buying a thousand of dollars in tickets wouldn’t have been a good move, but for Adam it’s actually sticking with what he knows and turning that into an opportunity.
Nate Broughton: And he’s going to take the risk too it’s a go a little bit further he also loves to travel right? I love how you mentioned that it’s a world that he knows, but he also, it fits his personality and things that he’s going to do that a lot of other people aren’t, and that’s really what he’s going to end up leveraging and profiting off of, as he tells us here.
You mentioned the Olympics right there and that’s where the entrepreneurial story begins if I understand correctly. Because you guys had access to tickets for the, was it the 2004 games?
Adam Dailey: Yup, the Athens Olympics.
Nate Broughton: Okay. I mean what was going through your head at the time like I’m curious because you talk about being an athlete and I was not as an accomplished athlete as you but that was kind of more my focus also when I was younger and entrepreneurship came later and that kind of seems like the point in your life where it kind of first happened or at least your reference in your story. So how did the entrepreneur in you come out at that point?
Adam Dailey: Growing up I was always an entrepreneur. I was always making cookies and selling them to the neighbors and going washing cars and how my lemonade stand was on the front page of the paper when I was a kid. So I always had that thing in me. Being an athlete I think was especially at that level I was so focused, so disciplined, talking about goals all the time. I mean I was obsessed with being the best athlete I could be. So a lot of that really translate, I didn’t have an outlet after I stopped competing for a while.
So I didn’t really know where to focus that energy and once I could figure out an opportunity, figure out an angle I guess you could say that really helped. You know I got access to tickets because I’d run in the Olympic trials. It wasn’t an aha moment or anything like that. It was more like I got a few thousand bucks, here’s access to a bunch of tickets, and I always hear Olympic tickets are great. I should just buy some and then I’ll figure out down the road which is kind of what I did.
I bought a few thousand dollars’ worth of the tickets and I didn’t think about it for six or 12 months from then.
Nate Broughton: But it’s a side hustle, right? It’s like a-
Adam Dailey: It was a side hustle before people knew what a side hustle was. It was more like I didn’t know maybe I’d be an athlete. I had not given up on athletics at that point completely. So I was like well maybe I’ll be an athlete and make the Olympics or maybe I’ll sell these on eBay or who knows and so I didn’t do stocks. I’ve never really been a stock guy and so I just was like oh I’ll invest in this because it seems safe and it seems like there’s a lot of upside.
Nate Broughton: But not too long after that at least, at some point between there and when the Olympics happened you guys decided to move to Athens.
Adam Dailey: Yeah. We got the idea to basically combine them with some hotels and we realize like we know all these guys. We know the Olympians. We’re friends with most of the guys who are going to make the team. So we said, “Look if we can combine hotels and tickets and be on the ground that will be a huge win.” It wasn’t a business that we were trying to scale or anything like that. I mean we thought up the name we didn’t put much into it but we were just like if we can pay for ourselves to live in Greece for a year we’ve won.
Nate Broughton: And you just figured it like combining the tickets and the hotels there’d be some sort of margin people would pay for it because it’s a hustle to figure that stuff out especially even then pretty good internet I guess. I don’t.
Adam Dailey: Totally yeah. Ultimately I just I didn’t have a business plan per se. I just knew if I’m there and I’ve got my back against the wall I’ll figured it out and I knew that people were intimidated and a little perplexed by what is out there and how far are these venues from each other. People don’t speak English. So I knew that the opportunity would present itself if I could reach out to people say, “Hey I’m an American based in Athens. I’m your man on the ground. I was a former athlete let me help you get situated.” Which is kind of what we did we did a lot less of the tour.
I mean we had a tour business and that’s how we made some money but I guess you could say almost the side hustle, people would hire me and give me between 500 and a thousand dollars to find their accommodations straight up and I wouldn’t put anything on top of that. But I knew where all the deals were because I was going in to talk to the hotels and every day, and the hotels were worried about me adding something on. So I could connect the hotel with the end client and hotels are like, “Okay you’re not making anything on the side.”
I’m like no they’re my friends please help my friend out and my friends will pay me you know not a bunch of money but like I said 700 bucks and you’re going to five or six of those a week and you know I had a couple employees at that point that was paying for everything. But it was total just hustle, we got three months to make this work at the end. The last three months were really head down hustle. Go for it and we knew we had to make money basically because there’s no money to be made after the Olympics.
Nate Broughton: Right yeah kind of an interesting business model or business situation as a very specific end point doing that event marketing and ticket sales. I mean sounds like a perfect business for a young couple who’s struck by wanderlust to have spent time in Europe prior to that and wanted to travel. I mean that I must have been a dream time in life.
Adam Dailey: It was and you know at the end of day you can look back at stuff too and go, oh like when we we’re living there in the months leading up to the Olympics we were stressed about are we going to make this work or not. So looking back on I’m like oh we should have traveled more to the islands and done more this and that but we were focused on making this a successful venture. So I think you can always look back on it and wish you did a little more travelling or a little more relaxing or whatnot but it was a great year.
We’ve lived in Greece and Germany and Italy and Spain and Canada and all these places and that was like the second place and that opened up Europe to us again basically.
Nate Broughton: Yeah I mean it was the jumping off point for you doing a bunch of future events. During like the 2006 Olympics in Torino. I think you skipped that ‘08 Olympics in Beijing, right?
Adam Dailey: I didn’t live there but we opened up an office with four people there.
Nate Broughton: Oh okay interesting.
Adam Dailey: Yeah but I didn’t want to live in Beijing. So I went to Vancouver, moved to Vancouver in the beginning of 2008 to set up for the 2010 Olympics.
Nate Broughton: Nice.
Adam Dailey: Which to this date were the most successful?
Nate Broughton: Why do you think that is because I know like for the one in the story like the London Olympics don’t go well? But you’re just describing that Athens is kind of a faraway place, it’s the language, it’s the barriers, it’s the Vancouver, and it’s the closest place possible. It’s very American in a lot of ways it’s a hundred miles from the US. There’s nothing to overcome it seems like in my mind but why was that successful?
Adam Dailey: Yeah it was pre-Airbnb so there weren’t a bunch of people renting private apartments and ultimately it was easy and sexy enough. It was like if they would have been in Oregon or something they’d have been yeah I don’t know but Vancouver had this thing of like everyone says Vancouver is beautiful and for that matter people could watch the opening ceremonies on TV and they still had two weeks to like ha maybe I should go to the Olympics. I got two weeks left.
So whereas you couldn’t do practically you can’t do that when you’re watching the Italy Olympics or if you’re watching Beijing or I mean Russia you need a visa you know.
Nate Broughton: Yeah.
Adam Dailey: And so ultimately, I think that played a big part in it too, I mean we had tons of people just literally flying into Seattle and driving up as well and so I think there was a bit of a perfect storm. We also had, we were sitting on a bunch of accommodations in a cruise ship canceled like three weeks before the Olympics started and we were in the press releases as one of the only three companies that can help accommodate people. So luck always plays a little bit of part in this.
Nate Broughton: Yeah interesting.
Dana Robinson: How long did you live in Vancouver.
Adam Dailey: About three years.
Dana Robinson: Wow.
Nate Broughton: And you had one of your kids up there?
Adam Dailey: I did.
Nate Broughton: Nice.
Adam Dailey: Yeah. My son was born in Vancouver so he likes to root for Canada and in sports matches so it’s-
Dana Robinson: Well San Diegans don’t have very much to root for.
Adam Dailey: Yeah.
Dana Robinson: So at least he’s got a home team.
Adam Dailey: Exactly. He’s very proud of it. Wears his Canadian flag and tells everyone he’s from Canada.
Dana Robinson: How did it turn into three years? I mean a year seems like the pattern for you for ramping up to an Olympics?
Adam Dailey: You know we realized in this business the longer we’re somewhere, the better the business will be. So we decided be there for two plus years for the Olympics to prepare for the Vancouver Olympics and then we liked it there so we just kind of finished off the year there. That was how that worked for us. At that point I had joined EO in 2009 and I was like I’m a nomad. I’m always hiring new people every Olympics. I’m moving around. I want to build the business and I want to scale the business and I want to have a community from a business standpoint as well as friends in my social network.
So I really was looking to settle down somewhere and that’s where we looked at San Diego and came to San Diego in 2010 from Vancouver.
Nate Broughton: Why did you pick San Diego?
Adam Dailey: We’d always kind of figured we’d end up in Southern California and San Diego was cheaper than Orange County and LA and Santa Barbara those were the like the places we’re looking at and it was bigger airport. More culture and had seemed to have great neighborhoods and it was more laid back which I think was a plus for us at that point. I mean we were not LA people. We’re still turned off by lawyer, moms with face lifts driving around so.
Nate Broughton: But you still live in La Jolla?
Adam Dailey: We do, we do. I just get turned off by seeing them at the stop signs.
Nate Broughton: Well, let me break in here and preface this next part because we’re going to talk a little bit about San Diego and if you listen to this podcast unless you live here, you’re probably tired of hearing about San Diego and I wanted to give that some lip service in this episode because Adam’s from Austin Texas and I’m from Missouri. And we were having coffee before we recorded this podcast maybe a week in advance. We were talking about our kids and raising them here in California and also both of our journeys as entrepreneurs having offices here in San Diego.
And I was like it’s pretty good life out her. But Adam’s like, “Sometimes to me it feels like the culture out here people are proud of it and they act like they’re all laid back but I don’t think it’s laid back. I think it’s lazy.” I laughed and I was like, “Yeah that is one way to look at it.” And Adam goes on to say here as he talks about this that a lack of culture doesn’t mean there’s a culture. San Diego’s a great place for lifestyle and weather and some things like that, but we use it as a backdrop just because it’s the place that we live and we choose to be.
It doesn’t mean it’s a perfect place for a lot of different reasons and I love that Adam was able to drop that tidbit in because yeah we both do choose to live here and Dana chooses to live here and we expunge in the lifestyle and how great it is but it doesn’t mean it’s a place that doesn’t have its own faults. And coming from a man who’s lived around the world I think is very telling to hear him tell those things. I just wanted to point it out so we can listen to what Adam says about San Diego and the difference between it and where he’s grown up and other places he’s been.
Adam Dailey: My frame of reference I think in our conversation was a lot about like the way my children are raised versus the way I was raised. And I grew up in the south. I grew up in Austin Texas and I went to school at University of Arkansas. So I had good Southern roots even though my parents were liberal hippies from Oregon, I said yes sir and yes ma’am and I studied Texas history and I understood how to look people in the face. And I felt like when I go back now when I go to the south I feel like there’s a strong culture and I feel like in San Diego we don’t have that culture.
We feel like our culture is laid back and like I said, it’s not laid back it’s lazy and a lack of culture doesn’t mean there is a culture because I think that’s how we define it like no we don’t we’re nothing. We just kind of surf and hang out and move slow which I love that. Obviously I choose to live here. But I also see my kids and all their peers and maybe it’s a generational thing not just a Southern Californian thing, but they don’t look adults in the face, and they don’t call a Mr. or Mrs. and they don’t say yes sir or yes ma’am and they don’t eat everything on their plate.
Just these simple values that I grew up with not knowing there was choices that I could you know oh I don’t like vegetables or things like that and like I said I not all a result of our surroundings in terms of geography, but I do feel like San Diego moves really slow and we’re sometimes we’re a little too proud of that.
Dana Robinson: Yeah little informal a little less etiquette maybe.
Adam Dailey: If you show up to any meeting wearing like a sport coat people are like what the hell is this guy trying to sell me. What are you trying to sell me?
Nate Broughton: Yeah no, I like that. I like that and you’re right. You know we were talking about kids and raising them here and wondering how they would turn out. There’s that aspect of it and also the employees here like I’ve had a little bit more experience with that because my kids are still young but the jury might be out. But hiring people in Missouri versus in San Diego, the expectations and just in general I mean it’s not every single person at all. We used to have a company that had about 25 people on it and 12 of them were from the Midwest and 12 of them were from California.
You could definitely tell there is a difference between what they thought they were going to get out of this and how long they were going to be there and there is just a little bit more of a work ethic and we’re here to work that’s why we’re here. We want to do a good job sort of thing. A little bit more pride in that I felt like from the Missouri group.
Dana Robinson: It’s easy to feel entitled in San Diego-
Nate Broughton: Yeah there was entitlement.
Dana Robinson: … but weather and the culture gives us a sense that everything’s all good.
Adam Dailey: I think we all look at it and go oh millennial. This is a millennial thing. This is a millennial mindset and then you run into someone from the Midwest or the South and you’re like ha they still work harder. They still see the world this way and they still go visit their grandparents or go visit the old home or they care about more than themselves. And so I’m like well maybe it is beyond just a millennial thing.
Nate Broughton: Yeah, very interesting. So yeah I mean back to the entrepreneurial journey you mentioned moving down to San Diego and that’s how we got off in that little tangent but you say you joined EO and up until this point you’ve been running a business somewhat of a side, as not a business with employees that’s been transferred from Athens to Torino to other cities and you found something that works and you’ve had a lot of fun traveling around the world and making it work. And you mentioned as we were talking there, that you decided you wanted to take it to the next level and so many words.
Moved to San Diego, put down some roots and grow. I know you mention in your book also that you were thinking about growing it and selling the business. Like you had talked to some potential acquirers and they’re like yeah dude this is cool but this business is somewhat of a lifestyle business not just because it looks like a lifestyle business because of what it is, but because so much of it is tied to you personally and your relationships and your skillset and if you want to sell a business that’s a big drawback.
So you come down to San Diego and decided to go for it so to speak. Why did you want to do that? And then also let’s kind of talk through what happened?
Adam Dailey: The ‘why’ is something I still question to be honest with you. I mean you can get surrounded by that growth mindset and it’s invigorating. It’s contagious, it feels good. It’s exciting. It’s exciting to hire people to make more money. All these things I think are emotional and they can drive you. For me I really I didn’t see the light at the end of the tunnel but I saw I didn’t want to be doing this forever. For me I started the business because it was in these great places.
It was in Greece and Italy and all these places that I wanted to live at and that I liked the culture and that I enjoyed the event having to do with Vancouver or whatever. And so I saw that moving away also I saw these events were going to places I wasn’t as interested in and I just ultimately wanted to cash out one way or another. Whether it was work less and focus on some other ventures or sell the business. So I think where I went wrong was I was doing $3 million or so in revenue at every Olympics and my business coach is like you’ve got to have a goal. You know you got a goal and so from my goal for the London 2012 Olympics was 10 million.
10 million had nothing to do with any kind of logic; it was just a number I pulled out of a hat. So you know looking back on it, I’d never done that before. All I cared about before was profit making more profit than I had the last time. I could’ve told you in 2008 what my revenue was for Beijing. I had no idea whether it was one million or three and a half million. And so I was really focused on the revenue number and the story I would tell was we wanted to hit 10 million. We hit seven and the issue was eight was our breakeven.
Dana Robinson: This is a really interesting point that we want to break in and talk about. This idea of a lifestyle business, it means a business that empowers somebody to live a good life essentially. Often a lifestyle business is one where you don’t have a time when you need to show up and you don’t have a lot of responsibility. Most people with hundreds of employees don’t have lifestyle businesses. People are jealous of them but they don’t have the power to live the life that they want.
Well, Adam had built a lifestyle business by happenstance. He wanted to travel and as it happened this was a travel based business. It made good money and empower that ongoing travel and breaks in between when he would travel some more. So he’s got this lifestyle business and at some point he thinks I really want to go big. There are some different motivations that are cooking and simmering in him at this point.
Nate Broughton: Yeah I think he’s been doing it for some time. He’s got a young family now but actually what he talks about his both his business coach kind of challenging him to have a big goal and also looking ahead to the coming events and deciding those don’t just interest me that much which I think is kind of cool. But yeah coming back around to like I’ve had this business it’s been successful. It’s allowed me to do so many different things, like to plants and roots in San Diego he decides and go after this $10 million goal for next event. That’s no joke and that’s definitely not a side gig or lifestyle business.
Dana Robinson: Right in this is going from $3 million in sales with lots of profitability and the ability to have a small staff live on the profit, enjoy the freedom that that’s giving and now he’s going big. Putting it all in.
Nate Broughton: Yeah and you listen to him tell a story, I mean there’s things that we caution about taking a side gig and trying to make it not a side gig anymore and there’s always a gut check decision if you really want to do that but he quickly found out that he has trouble scaling by hiring a bunch of newbies who don’t know the industry, having expenses running rampant in a business that’s larger than anything he’s ever managed and having to put a lot of his own cash on the line. You know ultimately it doesn’t work out.
Adam Dailey: And that was a tough one in many ways and it was a tough one like you said with the employee … I mean I remember a month after the Olympics you know we had to get rid of about half our team, almost half the team and one of the people who stayed was like we made $7 million. So we certainly were profitable or something to that matter and I was like no you don’t get it. That was my bad, I didn’t show her enough. I was trying to do some of the open book management. I was trying to explain to them because they see it was like $7 million, Adam gets only two big expensive cars instead of three that he was planning on it.
So whatever logic they look at it and that’s when I was like no we lost a million dollar. I lost a million dollar so I have to answer for the million dollars.
Nate Broughton: Yeah interesting. Yeah it’s interesting to hear there’s kind of just a number you pulled out of that. Maybe your background you talk about being an athlete and being so focused on that and accomplishing it. I think you were just like pick a big goal and figure out how to make it work. You know that’s your story in a lot of different areas and that was a big goal.
Adam Dailey: Yeah,
Dana Robinson: Was that bad advice?
Adam Dailey: To pick the $10 million number or what do you mean?
Dana Robinson: Well you heard that your coach said you need a goal. I mean sounded like your goal was working. Your goal was make enough money to keep this cool life going and so profit was a motivator and then when you suddenly have this sort of big mission you pour yourself into that.
Adam Dailey: I think the goal was good the goal was wrong you know what I mean? Like again I think it’s more important to focus on profit versus revenue but I also think I didn’t have the systems in place to be able to know whether that was a good number or not. I mean I was throwing so much money in every direction marketing here … I mean but right before I threw $50000 in the direct mail campaign you know like literally like a month and a half before the Olympics. And I’d never done anything like that. I had no idea whether it’d work but I was just throwing everything against the walls, seeing if it would stick and I figured I’d always kind of been successful and I always had a bunch of money left over.
So I kind of was like well if I make 10 million I’m going to make a lot more profits. So I can afford to invest in my people and I was sending all my employees all, every conference they would want to go to. I don’t think it was wrong, I just think it wasn’t well thought out. I mean look at it you’re talking about tripling your business while going backwards to build your business to take three times as many people. To have three times as many employees. To have every system set up so you’re ready for it.
It was just too much at once and for the most part I think I had maybe one person left from Vancouver that continued. So it was all a new team as well.
Dana Robinson: I was going to ask if you’d mind taking a minute to talk about the mechanics of the business. I think a lot of our listeners haven’t started business yet or they’ve got a little side gig and they’re trying to figure out how do they make that bigger. How do they grow that and so when we get entrepreneurs on here it’s pretty easy for us to jump ahead and start talking about pivot to big business scalability growth. Do you mind taking us back to the small business when you first started this like how did the business work?
Adam Dailey: We use the word bootstrapping a lot today and you know in these types of podcasts. I was bootstrapping before I knew what it meant but it just meant every dollar is mine right.
Dana Robinson: Yeah.
Adam Dailey: And so I was paying attention to it one way or another and at some point I stopped paying attention.
Nate Broughton: So you’re taking dollars that are yours, you’re buying tickets to events well in advance, you’re holding those tickets and you’re also negotiating deals with hotels in advance right? Because that’s usually a component of what you’re selling and paying for those in advance as a separate.
Adam Dailey: Yeah I’m doing non-refundable deposits basically. And so usually I’m lining up the sales as the deposits come in type of thing. Like if I bought a million dollar hotel in Vancouver and it was you know 20%, $200,000 upon signing then, 20% six months later or something like that. And typically the clients were coming in at the same time and someone was signing up for the Olympics a year and a half before and I’d say, “Hey 25% at the sign up.”
So and it was also you know 10 years ago, 15 years ago was a time when credit cards were flowing and you could do 0% balance transfers with no transaction fees, so I got half a million dollars or more on credit cards that I could basically sell finance any kind of deal for virtually nothing, for between 0 and 2%. Those types of deals aren’t really around anymore but that was a good time to have credit cards and kind of build your business in that way if you could maintain it.
Nate Broughton: Sure.
Dana Robinson: And you talk about in the book how that also racked up millions of miles if you ended up using for your big trip.
Adam Dailey: Definitely, definitely.
Dana Robinson: So you’re buying these tickets and locking up hotels using credit cards as 0% financing essentially and then you make all your money and if you manage your expenses you’re going to put some profit at the end.
Adam Dailey: Yeah.
Dana Robinson: How do people find you? Were you marketing to travel agencies in the US?
Adam Dailey: Yeah in the beginning we hustled and wrote every single person we could think of. I mean it was like, it was email, right. It was free and so we’d write every sports federation from every country and I’d find a page that listed all you know professional athletes and their websites and I’d get my team to go, okay write every athlete and just tell him who we are.
‘Cause everyone needed what we had, right? Which was basically, cheaper services by a person on the ground who speaks native English, it was a good service that was valuable for the athletes, their families, their support teams, sponsors. I felt like even to this day, we have a client list that is more diverse probably than any of our competitors in terms of we were doing high level Olympic IOC sponsors.
We were doing agents, sports agents. We were doing sponsors. We were doing the friends and families of athletes. We were doing coaches. We were doing the athletes themselves. So, we had this portfolio that a lot of people, the sponsor guys, that’s all they were doing, whereas the agents, or whatever, that’s what they were doing.
So we mixed it up, then we can buy and sell, and that’s where we started being really successful and we’d leverage one side over here. It was like, “Hey guys, we bought 100 rooms last year and we’re only going to use 75 of them, I’m kind of in some pain.” And then I’m like, “I’ll help you unload them.” And then I can go and make a bunch of money by selling their 25 rooms and brokering that. And again, that’s just me in my element, when I can work both sides of it and just hustle and figure out how to do deals.
Dana Robinson: Now, in between the Olympics, what was the business about? I mean did you take time to decompress or did you get right into the next one?
Adam Dailey: I mean it depended on the Olympics. There’s always that two and a half year gap between Olympics and then the one and a half year gap. So, the one and a half year gap, you just don’t have as much time, whereas the two and a half year gap, you can do some more. After Athens, we took about three months and we went and traveled through Spain, traveled through Italy and spent most of our profits from Athens.
Fast forward a couple of years later, after Torino we took about six months off. We went to Australia, Latin America, and China just traveled all over and spent again, a big portion of the money we’d made but we’d always like, “Why are we making money if we’re not going to spend it?” And for us, it was really about the travel, especially in 2006 and ’07, we knew we were probably going to have kids and in the next year too, we wanted to get some of those big trips, the bucket list trips done before we went down that other path.
Nate Broughton: Why were you guys so into travel? What made you and your wife both, because you kind of have to both be into it, obviously, if you’re especially going to do it at the scale that you guys do. Was it when you were younger going on trips with family? Was it something like that?
Adam Dailey: I mean, I think it’s a little bit of just a perfect storm. My wife, when she was 13, went and traveled, and spent the summer in Malmo, Sweden with her family. Her dad was set up there, running a plant manager for six months and he brought the whole family over for the summer. And she spent the next five years kind of romanticizing about that. How great that summer was, they did the big European trip in a band and went to Paris, Rome and everywhere.
I grew up not having that experience. But hearing my parents talk about their backpacking trips together through Europe and just, me, again romanticizing it in my head, going like, “Wow, that sounds amazing.” You can go ride your bikes in Belgium and get on a train, go ride to France. And so for me, it was more of looking forward to it, and Jessica brought out that enthusiasm in me as well. And so, we knew we wanted to do something like that, and then we did our honeymoon in Barcelona in 1999—
Nate Broughton: Nice.
Adam Dailey: And then Barcelona ended up being one of those pivotal cities and moments in our life.
Nate Broughton: You guys are going back there to live, like multiple times, since then?
Adam Dailey: Yeah. Like I said, we went for our honeymoon in 1999 and went back a year later. I worked for two years, Jessica did a graduate degree. We moved back there in 2007 and ’08, and then we’ve been back multiple times for a month or two, or three at a time. My daughter was born there, I got my first job there, went on our honey moon there. I mean, we have a lot of history with that city.
Nate Broughton: You mentioned romanticizing it and hearing stores from your parents and her having an experience. The reality of travel isn’t necessarily that romantic sometimes, I mean, there’s moments that are romantic, right? But once you get there, and also on the journey there, you realize that it’s a big pain in the ass, and sometimes people are nice and things are hard. I mean, places are set up to make the locals comfortable, not you, right? I think that’s a quote from your book. And I’m either quoting or paraphrasing.
So you go out there and you find that the reality is not as romantic as the stories that are told, but you continue to do it anyway, which is interesting and I want to ask why because you continue to do it through having a family, through having businesses be successful and not so successful. Why still fight through that to travel?
Adam: I think there’s multiple pieces to it. One is being uncomfortable. We’re trained in our head to think that’s a bad thing. And I don’t think being uncomfortable is always a bad thing. And I think travel is one of those things that really make you really uncomfortable. At certain points, you’re going to be uncomfortable or you’re going to miss a flight, or you’re going to not be able to check into your room or if you’re travelling with children, it adds a whole other layer of complexity to it. So being uncomfortable even though we think of it as so gnarly, I don’t think it’s a bad thing. I think it’s good to kind of reset you.
I also think that it’s really easy for us to be very ethnocentric and for me, I love Europe because you can get on a 60 minute flight and have a country with hundreds of years of different history, with a different language, with different food and it’s such an amazing place in that way. And so for me, it’s that culture. And for us, it was really about teaching our children about these cultures and even if our kids don’t remember Greece, they might, somewhere deep in their chip go, “I remember somewhere people speak other languages,” right? I remember houses weren’t as nice or whatever they want to remember. And I think especially with the way things are now with our world, it’s important to think outside of your little bubble in La Jolla and go, okay, there is a bigger world out there and there are other things out there.
Dana Robinson: All the pain is worth it, right? I mean the discomfort. I mean, there’s this tension that Nate is talking about, the tension between all the work and the hustle and the things that go wrong, and the things we do romanticize and we should romanticize because those memories are amazing.
Adam Dailey: If I got you to write out your best travel stories ever, I bet you 65 to 75 of them would be centered around some kind of problem, right?
Dana Robinson: Right.
Adam Dailey: Because that’s what makes the story memorable. You’re never like, “Man, we flew into Kabul and went to stay at this resort for like two weeks, and that was like… Man, I’m still talking about it.” We’ve got to do those things, I guess, every now and then but that’s a resortist, not really a traveler. Those memories don’t really stick out. So I think the best stories are being uncomfortable and to this day, the best stories you’re going to tell are probably some problem, right? Some issue you had and you came out ahead. It all worked itself out, right?
Dana Robinson: I think it’s a great opportunity for the two of us to share a couple of our stories about travel. I think this is really insightful, the idea that the obstacles, the bad things that happened, the challenges of travel are actually the things that create the best memories. So, one of my fun trips as a family, was when we took our daughter to Vietnam. And Vietnam is very assaulting on the senses and we wanted to go in deeper than just Ho Chi Minh City, so we booked a flight to a small island called Phu Quoc.
Phu Quoc, you might have heard the word if you have eaten Asian food. It’s the island where they make all of that fish sauce that most Asian restaurants have on the table. While we were there, the only way to get around was a scooter, so we rented scooters and I put my 12 year old daughter on the back and she nervously rode around behind me as we passed cows on the beach, found some secret beaches, had a wonderful experience, found some waterfalls.
If anyone has got an 11 or 12 year old kid, they know that one of the biggest challenges taking them to someplace remote, is the food. So, we went to a really fantastic local restaurant and the only thing my daughter wanted to eat was chicken or French fries. And so we explained this as best we could to the staff and they found French fries pretty quickly. But it took about an hour for them to get the chicken. And it turned out, we were pretty sure they actually killing the chicken for us.
And they brought a whole chicken that had been boiled to the table. And my daughter looked at it with giant eyes and I just looked at her and said, “I think they made this chicken just for you.” And she did not want to touch this raw looking, boiled chicken. So, we finally got her to eat some of the chicken and she grimaced her way through it, but man did she get some sustenance, so the first big challenge, getting your kids to eat.
The other one is a kid who has never been on the back of a motorcycle is riding on the back. She was just starting to get comfortable with that and a pretty massive swell hit after the dinner. And we had several miles to go to get back to the hotel. So, we decided that the rain was not letting up; we’re just going to go for it. No ponchos, no rain jackets. Just our helmets and our bathing suits and out outer clothing. And this storm was probably one of the biggest storms I have ever been in. In the car, the street filled up with water within minutes of realizing we were driving through a river of water on the street.
Like a Biblical plague, frogs started coming out from the sides of the street and covering the street. So now we’re driving down the street with the rain beating down on us so hard you can’t see 10 feet in front of your face, and frogs, millions of them seemingly, all across the road. We’re running over the frogs, the trucks passing us are running over the frogs.
The sound is, as you can imagine, not appetizing. And my daughter holding on to the back of me did not know what to do. She was shaking. I started singing or humming the ‘Raiders of the Lost Ark’ theme music (singing) and she laughed and loosened up immediately and started yelling into the rain, the theme song from ‘Raiders of the Lost Ark’ the whole way home. We got home and it was one of the best memories that we’ve had as a family.
Nate Broughton: That’s amazing. We all chase those, you know. I think, that’s part of what we were talking about here with Adam at this point is those are the ones that are memorable. And it’s pretty hard to beat millions of frogs falling out of the sky on the back of a scooter in a torrential downpour.
Dana Robinson: You’ve got to have some good ones.
Nate Broughton: Yeah, I do, and I struggle to take any of that don’t involve kids because I think they represent, as you’ve described, a whole new set of challenges. And I mean, the one I was going to tell might hit home for everyone a little bit more because I think it’s a little bit more logistical and it actually worked out okay. So, we were going to Sweden for my son’s second birthday, back when I just had one and we had to stop off in the Midwest, obviously for the obligatory stop with the parents and then we went to New York and stayed in a pretty good place in Bed-Stuy and that was all right.
But the morning we woke up in New York, obviously my wife is already a little bit stressed about flying overseas with an infant, or a young toddler. Not sure how well the long flight is going to go and if we brought all the right stuff and it’s going to be two weeks in Europe, albeit in Scandinavia, it’s still intimidating to a mother. And we were in this place in Bed-Stuy that was probably a little bit questionable that we shouldn’t even be staying in this neighborhood, and I woke to a text from our Airbnb in Stockholm telling me that they were no longer going to accept us as guests, and they were sorry.
This has actually happened a few times with Airbnb and it has led to some interesting solutions. But I sat there staring at my phone and struggled to even want to tell my wife that we didn’t have anywhere to stay in Sweden because we were about to board the flight to fly there overnight and land there and not having anywhere to stay. So I worked quietly on my phone and my laptop to try and find an alternate solution and actually, within a few hours before I even had to tell her that we weren’t going to have anywhere to stay, I was able to find one and when we landed in Stockholm, the lady met us.
She was a young mother. She had a couple of kids in a two bedroom and a better place than we were even going to be staying in. And she led us up and she was like, “I was really surprised to get your request for a place to stay. It just popped up.” And then I was like, “Today?” And I was like, “Sure. Let’s do it.” And I was like, “Thank you, because you definitely saved me from a huge pain and I was definitely intimidating to be heading to the airport without anywhere to stay with a young kid and a concerned wife in tow.”
Dana Robinson: Did you manage to keep this a secret until the end or did you let Christy know?
Nate Broughton: I think she found out at one point. Somewhere in there, it became obvious that something was wrong and she’s okay, generally about the challenges we face. We’ve been through a lot worse, probably, but that one kind of stood out because I think a lot of people are scared of using Airbnb because that can happen.
Dana Robinson: Sure.
Nate Broughton: I mean, it has happened to us on a trip to Vancouver and then we had to find a solution. So if that does happen, there are ways around it and it’s just one more practical thing.
Dana Robinson: Yeah. One of the things Adam talks about is getting deals on the last minute for accommodation. In fact, in terms of our trip to Vancouver, we had a fantastic Brownstone booked in Vancouver. I was the first one there by chance. And the owner showed up. Apparently, the Homeowners Association had just instituted a $25,000 penalty for anyone caught renting on Airbnb. And he explained this to me gave us all our money back and didn’t give us any real choice.
And it was around midday, which is too late to start negotiating for a lot of those deals with other Airbnb owners. I wandered down the street and found this small hotel that had many rooms available and was able to negotiate for their biggest suite for our group, and by the time everyone else landed, we had gotten a better deal and had more space.
Nate Broughton: Yeah. And we’ll never forget that. Actually Gabe and I were telling that story yesterday to somebody. So, it’s definitely a memorable one, where he got to sleep on that pullout couch with Alex and always in the Murphy bed but it was quaint but I wouldn’t have traded that place for the world. And the same goes for my Sweden story, and I’m sure the same goes for your story of Vietnam. You wouldn’t change the weather or the challenges with the food or anything like that.
Dana Robinson: No. Our most memorable parts are not the part where we’re lounging by the pool; it’s the parts where we’re out having the adventure.
Nate Broughton: All right. Let’s hear more from Adam.
Adam Dailey: I think even travelling with the kids, for us it was good for them to see like, “Mom and dad don’t have it all figured out.” You know? “The plane is not showing up or whatever.” It’s like, “When are we leaving?” “I don’t know when we’re leaving.” “Wait. You don’t know everything? You don’t know when we’re leaving?” And I think it’s good for kids to see that. To see that everything doesn’t go perfect, that mom and dad don’t have the answers, and maybe we can all figure them out together.
Dana Robinson: Yeah. You’ve got a lot of expense management strategies, I think, in the book. And we talked a little bit about them. It depends on who we’re interviewing and our guests and where they are at in their life. But I love to catch people who still hold on to their hustles on the expense side of things. I mean, most of us as entrepreneurs have got hustles for income. How am I going to consult a little to make some money here? What’s my side gig online here? What’s my passive income? What’s my business? For me it’s also real estate.
So you’ve got these side gig business real estates that fill in for income. And once you’ve done that for a while, it’s easy to lose track of the expense hustle. But I love that in your book, you’re like, “Look, you must have saved tens of thousands of dollars in air fare by using miles.” But there’s work involved with that, you’ve got to hustle.
Adam Dailey: There’s work. And the same thing with, like I said, trying to get broad deals on accommodation, ultimately you’re dealing with an end user who either wants the deal or not. But, like I said in the book, it’s like the guy you are going to college with who asked 100 girls to a hookup during the course of the evening. And for the first 99, you and all your friends are like, “What an idiot. That’s humiliating.” And then on the hundredth one, you’re like, “Dude, that guy is the bomb. He’s a genius.” But you have to take some rejection. And for me, I would get these templates and I would write them and tell them about what I was doing and write about my family.
I would go looking for these seven days, and I want to spend $900 for these seven days. And it would be very clear. It would be like, “Do you want it or not?” And I’d write 40 of these or something, and 30 would ignore me, and five would write back and tell me “Good luck, you’re never going to find a deal like that.” And then three or four would be like, “Hey, let’s talk.” And ultimately, I’d usually end up choosing between three really good options that are within my budget.
But it took time. It was not for me, but I could see for some people being embarrassing to put yourself out there and say, “You’re doing this trip.” And sometimes I even use my kids’ names and sort of, “My son Blaze is going to have a birthday during this trip. I would love to find a really cool place for it.”
Nate Broughton: Yeah. So many things you went through right there. It would be non-starters for people I think in doing what you did, not just travelling for a year but selling all your stuff, booking flights 11 months in advance and not knowing how you’re going to get there, showing up at a—
Dana Robinson: Or where were you going to stay when you’re there?
Nate Broughton: Yeah, right. And then showing up at a place and being like, “The best way to do this is actually get this last minute, so we don’t know where we’re going to stay.” And doing that with five kids, I mean they were probably like, if I had a checklist of like 14 things you’ve said in the last few minutes, a lot of people would be like, “Oh, I’m not doing that.”
Adam Dailey: The kids are the resilient ones because the kids, after a couple of months that was their life. They didn’t remember home. They remembered, “Oh, this place sucks. We’ll be at another place in a few days, or a week, or two.” And so, they weren’t stress … “Oh, it’s exciting. And now I get to share a room with Kiara instead of Jay. Now we have a back yard.” “Now, we don’t have a backyard but we’re in the city.” So it’s crazy how kids can adjust.
And even at the end of the trip, I always remember we came back and we were looking at places in San Diego and we’d show them these places, these 3,000 square foot empty houses and they’d be like, “This place sucks.” And I’d be like, “What do you mean?” “Where’s the furniture?” “We have to get furniture.” And they’re like, “Whoa. How long are we going to be here?” And I’m like, “We’re going to move here.” And the little kids didn’t get it. They didn’t get what that meant; we’re going to live here. Why would I move to an empty house when we’ve can stay in this cool houses, right?
But I do think that the kids were almost the easiest part. Once it kind of got going, they knew how to travel. They knew what transition days on the plane meant, which is they got to play with their iPads. So they really actually liked the travel component because they’re like, “We get to eat plane food, and we get to play on our iPad, which we normally don’t get to do.”
Dana Robinson: Talk more about the family management aspect. How did you make it easy for your kids and therefor easy for you?
Adam Dailey: I mean we tried to lay out what we were doing. One of our children’s, transitions are tough for him. He likes the routine and so we talk through like, “Okay, this is what’s going to happen. This is what we’re going to do tomorrow.” And it would still be hard for him, and that’s something that we adjusted as we got along, as we tried to rip off the Band-Aid as much as possible. If we knew we had six hours of driving, we’d try and just knock it out in a day versus go somewhere stay two nights and then drive three hours, and then drive three hours two nights later, something like that. And we pushed responsibility around a lot. That was a big part of our trip is we gave our daughter a lot of responsibility. Take your brother to the bathroom, go and ask that guy when the next rain leaves, or go and do this.
So between all of us, it was definitely a team effort. Stay here and watch the bags for a sec while I use the bathroom. Just different little things, again that would probably make some people really uncomfortable, or even some parents like “Oh my God. You left your daughter watching a backpack in Italy while you were in the bathroom?” I did, yeah for sure.
So, the management part was a big piece of it, and I think my wife and I have that relationship where we just kind of look at each other and I’m just like, “I’m going to drop you off at the front of the airport and I’m going to return the car and I’ll bring Blaze with me and I’ll meet you back around in 12 minutes. Take my passport.” But we don’t even say all that. We just kind of look at each other and know what to do. And again, I’ve been there with other people and they’re like, that interaction stresses them out to watch me do it.
Dana Robinson: The great part about your book is that for those of us that travel, it seems like you’re preaching to the choir. It sounds like reasonable things. For those that haven’t traveled, reading your book seems like essential reading if you’re going to do family travel, because for a lot of people, you had built that instinct with your wife. So you have this intuition. You have the ESP, you look at each other and nod and you know exactly who is doing what like a couple of secret agents.
Nate Broughton: I think I was going to say it’s kind of a muscle routine and it’s like a work out. It’s like anything like that, that you do it enough times, you just get in the flow like I know when we go to the airport, as soon as we get out of the Uber, she’s grabbing the car seats, I have got to make the stroller go up and she puts a kid in there, and while she’s doing that, I’m giving her the carrier, and the kid goes in the carrier. And then I put the carrier seat in the bag. And this becomes routine like anything else out there.
Dana Robinson: It’s like a dance.
Adam Dailey: Right. It is. It is.
Dana Robinson: For sure.
Nate Broughton: One thing you talk about in the book, and probably was part of the genesis for the book, was journaling while you travel. And that’s something that we’ve done, actually we’re about to redo our honeymoon 10 years later and we do have a journal from it. And another trip we did, we went like 30 days around Asia and I wrote a little book. But that’s two trips over the course of 15 years where I’ve done that. I haven’t done it on all the other ones and I kind of regret it. So I guess, part of the question is, did you have an intention to write a book about this when you took off? Or did journaling somehow lead to the book?
Adam Dailey: I wanted to keep track of what I was doing and when I journal now, I wish what I was saying was deeper and my kids agreed; they didn’t think it was great philosophy one day. But a lot of it is like, I got to write down what I did today so that five years from now that’ll jog some other memories or I think maybe I’ll go back in three months and rewrite more of what I felt, but this will jog the memory if I write down that. Oh I did a podcast this morning and then I went and had another meeting after that.
And so a lot of it for me is just kind of keeping track because you do, I mean the older you get you kind of forget some stuff. I would say I had a goal maybe of writing a book at the beginning of the trip, but I didn’t really know what the book would be about. I didn’t think it would be about my travels, and I didn’t think the journal would reflect that necessarily.
I just knew it was a healthy thing for me to kind of write down what I was doing, what I was feeling on a daily basis. And I didn’t actually accomplish that. Every day I have notes of what I did, but sometimes I would go a week without writing it down. Then I’d go backwards and like I said instead of writing you know how that the dew on the grass was wet this morning as I sipped my coffee. I’d be like, we went to the zoo that morning and then after that we had lunch here, and it was twenty bucks and you know just different facts almost, that for me were really important in terms of being able to remember this trip for us.
Nate Broughton: Had you written anything before that? Because I mean you’re an athlete or an entrepreneur, or I mean writer?
Adam Dailey: I mean I had a journalism degree in college, so I think I had that kind of writer in me. What started this was I wrote another book that I haven’t published yet but it’s like about all my like ticket stories. So that was what started the creative piece of it was when we mentioned that my business partner getting thrown in Brazilian prison in 2014.
I was on the way back and I wrote this letter basically to my family, saying like this is what happened. I don’t want to have to spend fifteen minutes or twenty or whatever how long or half hour explaining this whole story. I will, but I want to just write it down and give it to you. So you can read it and then you can ask questions. It was for my family or his family, or friends or anyone.
It wasn’t a secret but it turned into this 14 page letter basically, that everyone was likes, “I got nauseous when I read that.” And, “Oh my God! I was sweaty,” and then everyone was like this was a great story you wrote, and I’m like you know the story was good but I also have a lot of other stories like that. I mean it was the first time anyone’s got thrown in Brazilian prison but I’ve had other people get thrown in prison.
Nate Broughton: Some of the things you said right here are very Opt Out Life as we try to describe it to a T. Do you feel like you live the Opt Out Life now?
Adam Dailey: You know, I go back and forth with that, because I find myself more and more getting into the struggle or whatever we want to call it, or you’re falling into the trap of your calendars full with everything. And you’ve got more responsibility than you know what to do with. So I try, I strive for that and then there’s other days where I’m like man I just want to move to Wyoming, and buy a farm and not worry about things or travel again. I mean I have that itch to go do another year, and my wife and I are talking about it.
And it’s like on the one hand we’ve got our house now where we really like it. We’re doing this renovation where it’s going to be pretty ridiculous. In terms of the house it’s going to be amazing with the pool and everything, but then in a way I’m like you know the sheer cost and the work that’s going behind is stressing me out. But I’m also like well this is going to be a great; I mean we’ve rented out on AirBnb for the summer, for a month of the summer.
So I’m like this is going to be a great AirBnb property and I’m thinking at the back of my head, so I can go do this full time for another year instead of just a month. I mean last year we went for like five or six weeks to Spain and this summer will go for a month to go Costa Rica. I think that helps when we can kind of do the arbitrage or renting out our place like that, for me that’s what changes everything. Is when I’m spending money on where I’m staying tonight and that’s it.
Dana Robinson: So when you take a vacation, you AirBnB the house you live in?
Adam Dailey: Yap.
Dana Robinson: So your residence becomes someone else’s vacation home for five weeks. You use that money to pay for the trip that you’re taking.
Adam Dailey: Last summer I think we were gone for like say about five weeks we rented our house for $14,000 and we spent $17,000. We went to Europe with tickets for the whole family, for seven of us, for five weeks and spent $3,000 and basically on food which would have probably spent here anyway.
Dana Robinson: It’s a great story from Adam, because it shows his desire to travel is not just something that he’s got to find the money for and make more money and blow that on travel. He’s got the asset right there. He’s living in it. He basically takes the house that he’s living in and he rents it while he’s gone, and that money pays for the entire trip. In fact in some cases that’s enough money to pay for the trip and more. In his case it’s $3,000 short, but in that five weeks, he would have spent that much money on food at home and expenses at home. So in a sense it’s saving him money versus just staying at home.
Nate Broughton: Yeah and I love the mindset he has about it but also the mindset that it puts you in and we kind of talk about that. Like if you know you’ve got this cash coming in from renting out your place, how different is that feeling when you’re out traveling with the money that you’re going to be spending going around especially with a large family. I think that totally changes the equation both on paper and also in your mind. I think at least a lot better trip.
Dana Robinson: Yeah I’ve done this with success. I’ve done this and not had any damage, a lot of people they’re afraid of what’s going to happen my things. Adam tells us nothing and my experience is the same. It’s a great way to make your house an asset.
Nate Broughton: I’m really curious of people listening to this, coming around to this idea. I think it’s crazy because I think at least half of people are going to like, “No I would never do that,” for the excuse that we just brought up. I can’t think of anyone back in the Midwest that I know that would be down to do it. But it’s hard to argue that this is a trend that is kind of pushing forward. Where not only are professionals AirBnBing their house, but your average person is going to get more and more comfortable with it, because there’s transparency on the platform.
I use AirBnB a lot and I read the reviews and I look at how frequently that they rent out, and how often that they’ve rented out and if they’ve had automatic cancellations because that pops up. Like I mention my story earlier where the person kind of screwed me the day I was flying to Sweden. What pops up in their feed of things that have happened, and I watch for people who have canceled a lot. So there’s transparency there that I think should help make it easier to not only choose someone to have them come in and rent your place, but also find a place that you’re going to use and people will become more savvy using those platforms both as users and as renters.
Dana Robinson: Right the platforms provide a safe environment for this very thing. I certainly wouldn’t take a renter who finds me on Craigslist and I wouldn’t promote someone to use my house or rent it from Craigslist. I mean Craigslist is not a self-regulating platform. There are others though like house swapping sites, where you live in someone else’s house in another country for the very same three weeks that they’re in your house. And in that case it’s sort of a standoff .Why would someone be in your house and damage your things, when you’re in their house right with their things. So there’s certain mutual respect from that.
So I think it’s a great travel hack. It’s a part of the Opt Out Life to talk about it a lot in the book as well. But I want to talk also about the idea that Adam is about to get to. He is about to tells a very interesting approach to real estate. Where he actually buys a property, knowing that it will perform better as a short term rental than it’s currently performing as a long term rental. You should pay attention to this, because not every deal is going to work out this way but it’s a great opportunity for people to sit back and go, “Hey, maybe I could do that.”
Nate Broughton: I know you’ve done that, how do you evaluate that opportunity I guess in your experience?
Dana Robinson: A lot of it has to do with location and it’s easy to see whether something’s performing by looking at AirBnb and to see are there other properties that are renting? What are they getting for it? I’ll give an example of one that didn’t work. I have a property in North Park, in the high seasons for say five or six months I’ll do $2,000 a month on AirBnB. As soon as the low season hit I drop to 800 a month. Now if you average that out over the course of a year, I probably was doing $1,400 a month.
As a long term rental I’m getting 1850. So after running that as an AirBnb for a little while I decided the economics just weren’t there. And what that means is I wouldn’t go buy another one in the neighborhood with the intent to make it an AirBnb. For Adam he’s got a property that he’s talking about in little Italy and he was already renting it short term he knew the metrics. I have another property on the beach. I know that rent short term is a vacation spot and even a small town; vacationers are going to want to be right in the middle of it. So if you’re out in the suburbs it’s a lot harder to make your money on AirBnb.
Nate Broughton: Yeah those locations you just described Little Italy is kind of akin to the beach. It’s a place that’s near the airport and it’s a place for a lot of visitors from out of town are going to want to stay. North Park is kind of on the edge, right? I could see why you think it might work out and sometimes it doesn’t. but just kind of draw the parallels back to the city, that you’re thinking about doing this in and listen to what Dana and Adam are telling you here and AirBnB be a great little real estate investment hack and platform. That’s new and a lot of people aren’t leveraging.
Dana Robinson: So what are you doing now is there any project that’s not too secret to talk about in the-
Adam Dailey: I mean I’m still involved in hospitality. I have a couple clients where I organize hotel room on picks, so we bought a hotel in East Village down here in San Diego that we’re doing a pretty extensive renovation. Turning it from kind of like a hostel type place to a boutique hotel. I have a couple properties in downtown San Diego that I do full time vacation rentals AirBnB on. I’m always looking for more of those deals you know in the hospitality space, like, “Oh, this could be a great event space with an AirBnB above it.”
So I would say that’s kind of a real estate play I guess but ultimately I think of it as hospitality you know. We’re looking at a lot of stuff and craft beer and spirits right now in terms of … No; not exactly investing but helping companies grow. And so again that’s probably my strength is that I know a lot about business and I know a lot of people and have a lot of really strong network but it’s probably a weakness. It’s really hard for me to focus on that one thing or one business for that matter. Because when something gets tough I can go open another window on the computer and work on another project.
Nate Broughton: So do you own the places in Little Italy that you rent out?
Adam Dailey: I do.
Nate Broughton: How long have you had those sites?
Adam Dailey: One of them was the house I moved down to in 2010 and then I bought the one next to it in 2016.
Nate Broughton: [Inaudible 01:11:25]
Adam Dailey: So that’s two houses next to each other. It’s a great location
Dana Robinson: I know why you AirBnB, BRBO on those?
Adam Dailey: Yeah.
Dana Robinson: Yeah, so this is something that a lot of people probably don’t realize this. Obviously, you can buy a house and then turn around to rent it. You’re an investor, you put a down payment whether it’s the one you lived in and then move out of and you can rent it, it’s great money. If your numbers are good you get cash flow every month. Like you did at your house when you went on your yearlong sabbatical right? You got a tenant.
Adam Dailey: Yeah.
Dana Robinson: Yeah the flip side of that is if you can find the right location and the right property, you can maybe double the rent and you run it like a hotel. You basically have people turn over every three or four days.
Adam Dailey: Yes the place in Little Italy I think it we’re making about $6300 in revenue, when we were renting it out to one tenant. He was running a business out of there on the first two floors; he and his partner were living on the second two floors. And we started AirBnB and you know I did 144,000. So more than double the revenue. And again you wouldn’t know that unless you tried it basically. So that’s why I bought the one next door, because I knew I had a different set of numbers than any other person looking at it, when it went up for sale.
The same thing that I know, we had another property that we sold last year in Little Italy, that was an old crack house that we bought and we fixed it up to be an office. It’s a Victorian house, a historical house in the heart of San Diego and we thought it would office space. Then it was empty for forty five days after we finished and I’m like I’m not going to not make any more money on this. So let’s throw furniture in there and run it for the summer, and it crushed any numbers any pro-forma that we had as an office space. We just kept that seven bedroom AirBnb.
So I love the AirBnB game. I think it’s an interesting story to watch in terms of the legal, the political, and all the different battles being fought right now. But I also think it’s like you can’t stop the market. When a buyer and seller want to do something they’re going to find a way to do it. And I think that ultimately wins. I think eventually one day our parents are going to be renting their house on AirBnb. ‘Cause they’ll say, “Well I wouldn’t do it, but I do it for ten grand a night.”
And it’s like they will get over the hump of like okay so there is a price. Because right now everyone, half the people are just so like, “Oh my God how could you have a person in your house?” And it’s just so foreign to people but I think eventually people everywhere, they’re going to get over that hump and it’s happening so much with our age group but I think it’s going to ripple everywhere and with everything but I think eventually you’re just going to look at any block and be like okay they have an office for rent.
You can rent by the day. You can have a room you can rent. There’s a hotel and they have they’re going to rent out the restaurant for a night. I mean it’s like where everything is negotiable.
Nate Broughton: I hope so and I can kind of feel it going that way too. We put our house up on AirBnb recently and the comment is that there is a price is exactly, when I came down to. I was like I’m just going to put it up for a lot of money and if it rents out great and if not then we’ll see how it goes. That was the starting point for me it was like, “I’m going to price it high, because I know if I got that I would be able to deal with emotionally and logistically what would have to happen.”
Dana Robinson: How is it going?
Nate Broughton: I haven’t got any.
Dana Robinson: But there’s a price?
Nate Broughton: But there’s a price. I was hearing your story about going to Europe and paying for it. I just paid 4500 bucks for a place in Sweden for two weeks. I’m like well maybe I should lower the price on mine while I’m gone so I can cover a bit of that.
Adam Dailey: I feel like it’s a waste thing too, right? I feel like I’m helping systems be more efficient because otherwise I have an empty house that’s a good house that could be a home to someone right. Like I feel like if I have that empty house it’s a waste. So I feel like I’m creating more efficiency in the marketplace by having it be full and for me I just I know I’ll feel better emotionally when I’m pull out my wallet you know four times a day on my vacation knowing like, well I rented my house up for 700 bucks today and I have only spend in 180 on the place I’m staying. So I have a little extra incentive.
Nate Broughton: That’s a good point to. I mean it makes the whole trip a little bit more fun right. Trips are emotional and challenging and if you make the money side a little bit easier I’m all for that, I like that.
Adam Dailey: Think about a trip you’re literally breaking out your wallet more than any other experience.
Nate Broughton: Yeah.
Adam Dailey: It’s all in one night.
Nate Broughton: Maybe that’s why like it so much. You spend cheap style.
Dana Robinson: A lot of people are worried when they rent their house to somebody while they’re away. They’re worried about their things. They’re worried they’re going to turn it into a crack house. They’re going to have an orgy. What’s your experience?
Adam Dailey: I mean the first time we rented our house we were living in Austin. We rented it for South by Southwest. I was at Home Depot buying the locks with the padlock thing you know for all the closets. And then I’m sitting there and I’m thinking, so these guys are going to break in my closet to steal my shirts. To steal my picture albums that’s what they’re after. I’m like if they were after my picture albums they probably just break the lock wouldn’t they? Because they’re curious to see what’s in there, like it was a trust thing. It was a thing of like being ridiculous for me and I don’t have a bunch of jewels and things like that. I don’t really have many possessions that I would care if it got stolen. But it’s also like I mean AirBnB little more probably even so than BRBO; I mean it is a community. So I trust the community to not rip me off and that was a hard thing the first time.
I get that objection from a lot of my friends, they’re like, “I just couldn’t, I can’t imagine like what do you do with all your stuff?” I’m like, “What stuff do you have that people want to take exactly. They want to go through and try your suits on?” and like let’s try the dresses on. I don’t know and so for me it’s almost the opposite. Now people you can make us any room in the closet, all your craps around everywhere. Maybe someone takes something every now and then, and I don’t know and if I don’t know that means it doesn’t matter anyway right?
I think the first time is the biggest hurdle, the first time you’re like, “Oh my God! Someone’s going to be in my place.” You know it’s a tough hurdle to get over.
Dana Robinson: I mean if you have an heirloom you can put it at a friend’s house or family’s house or when you want to find some hiding spot. It’s your house you know where the hiding spots are in that place.
Nate Broughton: Alright, two more things. Tell us an AirBnb hack or tip, or a power user point of reference or something like that, people should use when they go on AirBnB and try-.
Adam Dailey: As a user as a host.
Nate Broughton: User.
Adam Dailey: As a user? I mean again I’d use all the filters to get exactly what you want. A lot of people don’t know that when you’re in a very highly visited place they’re showing you their choices. So the more you zoom in the more choices you see. And again I would write as many people as possible and copy and save templates. And see you’re looking more or less for the owners. Because when you’re looking at property managers they don’t want to give you a deal, they don’t care if you book or not really like if anything you’re cutting into what they’re making.
So they were never going to give you any love, they’re never going to give you any deals. They’re never going to run your proposal by their owner. So you can that by seeing kind of at the bottom like, “Oh this guy manages 350 properties or he has 700 reviews on other properties,” that’s not going to be your guy. You want the guy who like just started last month right, and he’s like freaking out because all his friends told him he’s going to make so much money on AirBnb and he’s only got a few bookings and you want to even say that to him like, “Look man, I’m going to leave you a five star review because you’re giving me a bro deal,” so that’s a couple things I would suggest.
Nate Broughton: Yeah I need to adopt those I just pay full price. I’m going to learn from both you guys eventually. I mean how to manage to do-
Adam Dailey: I have old friends who do that and they’re booking AirBnb is with me and I’m like they’re like booking, I’m like, “Its tomorrow, why don’t you ask him if we can get a discount?” And they are like, “Oh, they do that?” I’m like, “Just ask, you’re about to book it anyway so your fallback is that you book it without a discount.” you know.
Nate Broughton: I’m going to think of the two.
Adam Dailey: They’re not going to be mad, they’re not going to be mad at you for asking for a deal.
Nate Broughton: It is not bad just that hassle, it’s like I finally found time to find an AirBnB, here’s one this is great I want to book it I want to move on with my life.
Adam Dailey: But I mean as a host I get people nine months from now booking a three night stay and they are like, “Can I have a discount?” I’m like, “No. For your three nights stay nine months from now during Comic-Con? No.”
Nate Broughton: All right last thin. A little exercise a little thing for us here. We get to go on a three night trip, me, you and you. We leave right now. We each get to pick one city. We’re going to fly to each one and spend one night. Which city do you choose for our three night excursion? I’ll go first or we are going to Tokyo on the first night. So we can eat a bunch of crazy Asian food and stay up drink until 5:00 AM. Scotch, karaoke, it will be a little tiring that’s where I want to go. Where we go on a night two?
Adam Dailey: On night two since we’re already east let’s go to Bangkok.
Nate Broughton: I’m going to have to bring even more energy.
Dana Robinson: Night market.
Nate Broughton: Eat on the street.
Dana Robinson: Street food.
Adam Dailey: A little street food. What are the markets on the water there? What do they call those?
Dana Robinson: Floating market.
Nate Broughton: Get lost hopefully we’ll find each other by morning you know in Bangkok?
Adam Dailey: In time for the flight.
Nate Broughton: And then where do we go on for night three Dana?
Dana Robinson: We’re going to stay in the east and we’re going to head to Shanghai.
Nate Broughton: Oh my God.
Dana Robinson: We’re going to stand in line for some pork buns. We’re going to eat some soup dumplings. Hairy crab season maybe.
Nate Broughton: On the boat?
Dana Robinson: On the boat.
Nate Broughton: Nice I didn’t know we were going to go all to Asia. We seemed. ..
Dana Robinson: I don’t want to spend twenty four hours on a plane.
Nate Broughton: Well next time we’ll say that it’s just like magic is happiness right now and I think we’d almost all go to Europe actually but just Tokyo was in my mind.
Adam Dailey: There’s always a direct flight from San Diego but-
Nate Broughton: That’s true that’s true.
Adam Dailey: That’s where I thought you’re going.
Nate Broughton: On the Dreamliner?
Adam Dailey: We’re only we’re only spending ten hours to get there.
Dana Robinson: And we’ll use Adam’s miles to get business class.
Nate Broughton: Yeah. Well, so that was a good little fantasy run but next time let’s just record the podcast somewhere in Europe. We’ll debate where this will be, but you know maybe next summer Opt Out Life Adam podcast to Barcelona-
Dana Robinson: Dusseldorf
Nate Broughton: Oh, Alright. Something like that so hopefully. Okay well I look forward to that future recording and our fantasy trip some point. Thanks for being out here Adam.
Dana Robinson: Thank you Adam.
Adam Dailey: Thank you for having me.
Nate Broughton: See you after the shoot. 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, and then head over to There you can enter your e-mail 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 of episode. Dana and I are also publishing new articles on the site including how to guides and blueprints for you to use to find your next side gig or find a creative idea to help you live the Opt Out Life.
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