048 & 049: 5 Simple Steps to Help You Start Travel Hacking

Hey, I'm Chris.

I'm a former Analyst, Podcaster, and Producer. My goal is to help you understand your finances better in about the time it takes to make a bag of popcorn!

Part 1

Part 2

Lee from BaldThoughts.com sat with me for a bag of popcorn and to share his 5 Simple Steps to help you start Travel Hacking.  

You may be wondering, what is travel hacking?  Travel hacking, in very simple terms, is the process of strategically using credit card rewards and sign-up bonuses to help you travel for free or pretty close to it.

I know I may be oversimplifying it so make sure you take a listen to the episode and also check out the great page that Lee has set up specifically for Popcorn Finance listeners to help you get started.



One of the tools mentioned by Lee to help you reach your travel goals quicker was Dosh.  You can earn up to 10% cash back at 1,000s of stores & restaurants when you add a debit or credit card to your account.  Plus you will receive a bonus if you use my link by clicking the button below!

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Full Audio Transcription

Audio transcription is still a work in progress, sorry for any errors.  Please let me know if they are helpful 🙂

Chris: 00:14 Hey this is Chris, hope you are doing well and welcome to Popcorn Finance where we discuss finance in about the time it takes to make a bag of popcorn. Thanks for joining me again for another episode and today I’m joined by Lee from BaldThoughts.com. How’s it going Lee?

Lee: 00:27 It’s going great. Great to be here.

Chris: 00:28 Happy to have you on. You know I met Lee about I think about six months ago at FinCon, which is the conference for finance bloggers and podcasters and we actually played some pick up basketball while we were down there. I think my body is still hurting from that game 6 months ago.

Lee: 00:28 Yep.

Chris: 00:50 I think that proves how out of shape I am right now. But anyways we got a chance to connect while we were down there and you have a website called BaldThoughts.com and on there you kind of discussed, you know, traveling but traveling for less actually, the motto on the website there is travel more, spend less and live better, which I think is a great set of words to live by. During our discussions. I think one thing we talked about a lot was travel hacking because I was really interested in and impressed by the amount of traveling that you do for, for I think really great price. Lee for you, what is travel hacking? Because from what I understand, it’s basically being able to travel using credit card rewards that either make the travel free or pretty close to it. I know that’s probably a super simplified explanation for it, but I’m sure you can give me maybe a better description of it then I just did.

Lee: 01:36 You got the basic concept down and essentially what it is is instead of being like everybody else where you’re paying the full price on, you know, on the airline websites, the hotel websites or even sites like expedia and things like that. What we want to do is find ways to reduce your travel costs so that we can take that money and use it for other things in your life or you can travel more. You can have better experiences. Uh, instead of going, OK, I need to eat at Mcdonald’s every time when I’m traveling because I’m trying to save money. If you save a little bit of money while on your airfare or hotel, now maybe you can splurge on a nice dinner or you can, I like to go to games when I travel & instead of sitting up in the nose bleeds because the trip didn’t cost anything as far as the flight of the hotel.

Lee: 02:20 Now I can sit down near the celebrities, near the court. So that’s, that’s Kinda the whole mantra, or you know, uh, especially because this is personal finance related. What I kind of encourage people to do is take the money that you would’ve spent otherwise on your travel and use that money to invest in your future by putting more money into your 401k, paying down your debt, or just investing to buy like a new house or to invest for your Kid’s education. So it’s really, you know, we all have a finite bucket of money. No matter what it is, no matter what job you have, whether it’s you making minimum wage or you making a few hundred thousand dollars a year, every one of us only has a certain amount of money that they have that they can, aside for all the different things in their life.

Lee: 03:01 If you can find a way to reduce that cost, whether it’s airline miles, hotel points, a certain strategies where you can earn additional free nights and, and all the other things, taking that money and redirecting it to other things that are, that are more important in your life.

Chris: 03:15 Oh Nice. I definitely think that’s a great way to handle the traveling and, and kind of get the most out of it & like you said maybe use that money to, to put aside for retirement or other goals you have in life. And so for me, I’m super, super new to this. I’ve just barely picked up my first travel credit card to give travel hacking a try and, uh, and so I wanted to come to you the expert, the person who I’ve seen do some great things in this space to kind of get your advice or some tips on how best to go about starting travel, hiking. And, uh, before before we jump in, I just wanted to give a quick disclaimer. You know, please just be responsible. These are still credit cards for everyone out there. I know for me, I had waited until I paid off the credit card debt that I had before I jumped in. So, you know, just as a recommendation, you know, maybe make sure, you know, you’re in a place financially to give this a try. But I think there’s definitely some big advantages to this if you do it properly. So Lee I’ll let you, let you jump from here and guide us.

Lee: 04:08 Exactly, exactly. Well, as you said, obviously you need to pay off your credit cards in full every month because whatever rewards that you’re going to earn from a, from a travel related credit card, the interest that you would pay far outstrips any sort of value you’re gonna get from, from the rewards. So the number one rule of anything related to the travel hacking is making sure that you’re not carrying any of that debt.

Lee: 04:31 So what I’d advise is actually have five simple steps to start travel hacking and the number one thing is knowing where you want to go, whether it’s to a conference like FinCon where Yeah, you can deduct the cost of an airfare to fly there. But yeah, even if you’re deducting the expense, it’s still an expense out of your pocket right. You’re spending a dollar maybe you’re able to deduct twenty five cents of that. You’re still paying seventy five cents out of pocket. So you know, I want to reduce that expense for as much as possible. So whether it’s traveling for something like that for, for your business or if you’re traveling with your family. I want to go see a game like I like to go see, or even you’re trying to further your career and there’s a conference that your work will pay for the conference, but they don’t have enough money in their budget to pay for the hotel or the air fare to get you there or you know, some conferences will actually allow you to attend for free as far as the conference goes, but you’ve got to find a way to get there.

Lee: 05:25 So all these different types of things is, is a way to know where you want to go. And then from there we can say, OK, let’s devise a strategy to help you get there. So that’s number one, is knowing where you want to go because, um, like for example, if you want to go to Paris, I love southwest. Southwest is my absolute favorite airline, but they’re not flying there, little 737’s all the way across the ocean to Paris. So Southwest is not the right airline that’s going to get you where you want to go. So knowing where you want it goes. Number one important thing as far as when you start a travel hacking,

Chris: 06:01 That’s a great tip. I think that was one of the first things you said to me when I asked, you know, what do I do to get started? Because I knew I wanted to travel, but then I didn’t even think about where do I want to go. So that, that’s a great, great first tip.

Lee: 06:10 Yeah, exactly. So you, that and then from there it’s like knowing how you want to travel. Some people, you know, they, they live, uh, you know, sometimes, uh, an economical life, but every so often you want to be able to splurge and you know what, I’d love to be able to fly in business class or first class, I want to stay in like a five star hotel, things like that. So if you, if you want those types of things, you need to make sure that the strategy that you’re pursuing is going to allow you to fly first class or business class or stay at a five star hotel, like a Ritz-carlton or Waldorf Astoria, something like that. Or some people go, you know what? I don’t care about all those fancy things in life, I just wanna be able to travel as much as possible. And so from there we can devise a strategy that’s going to give you a lot of economy fares and, and, uh, you know, lower end hotels that are still nice.

Lee: 06:58 I mean they still clean beds and you know, nice amenities, things like that, but they don’t, they’re not over the top like that. So knowing how you want to travel again is a, is a right way to do things as far as the next step. So again, southwest is my favorite airline. They don’t even have a first class on airplanes. So through um, you know, and for me it’s, I just want to get their for the most part, but every so often, once or twice a year, I really just liked to live it up and get pampered and spoiled flying, you know, that premium airfare. So, so knowing how you want your novels, the number two thing you want to do.

Chris: 07:34 Oh, that’s, I’ve seen some of your pictures and like some of the flights you’ve taken and some of the places that you’ve stayed in I think that really inspired me to hope in to travel hacking because, you know, sometimes you’re like, Hey, I’m just no way I would pay that much money for a hotel room, but if there’s a way that I could make it, you know, make sense for my budget, I would definitely love to take advantage of that.

Lee: 07:52 Exactly. Like about about 15 months ago, my wife and I flew to Italy because, you know, every year I try to spoil her and take her someplace really nice that she, she’s been wanting to go and between the airfare and the hotel is that we stayed at things like that. It would’ve cost $12,000 if I wanted to pay for that, for that trip and there is no way that I’m paying that kind of money for any, any one vacation, you know, that’s, that’s not how I roll. I’d rather take that money and invest in buying rental properties or, or whatever. So. But I use airline miles and hotel points and my total out of pocket cash was, I want to say about, uh, about 10 percent of that. So there’s about $1,200 was my total out of pocket.

Chris: 08:34 Yeah, that’s amazing right there.

Lee: 08:36 It’s like personal finance, everything is personal. And same thing with the, with your travel, it’s personal, what’s most important to you. And from there devising the strategy that’s going to help you reach your goals.

Lee: 08:46 So number three thing is kind of pick your favorites and focus on them. A lot of times people, when they’re looking at an airfare or they’re looking at hotel, they’re looking for most economical for whatever the lowest prices, uh, in, in the kind of the, the range of what they’re looking for, whether it’s a low end hotel, medium or higher end. They’re looking for the best price. And some ways obviously that’s great, right? You want to be able to save money. But if you’re earning a few points with Marriott and a few points with Hilton and a few points with a holiday inn and things like that, having a, a bunch of point spread, uh, among several different programs, that’s not going to do much for you, right? Yeah. Generally, you know, you want to focus on one hotel chain and one airline and pick those and stick with them and then from there you’re going to accumulate more rewards faster. So that way you can get that much quicker to your next free flight or free hotel stay.

Chris: 09:38 That’s a great tip right there because I know for me that, that was me for sure. I was like spread out everywhere. I have, you know, I’d have enough points for like five minutes in a hotel because they were spread out over everywhere. I had no consistency. So that’s a good tip there because I think a consolidated effort would make a big difference.

Lee: 09:56 Exactly. And it’s the same thing. So you have these points in these multiple different programs and you know because you’re trying to earn enough points to redeem for a free stay. Well if you’re not careful, you have a few thousand points here and there, those points can expire and next thing you know you did all that for nothing. So by consolidating in one brand and that way you’re, again, you’re getting a faster approach to getting that free night, that free hotel, stay that free flight and then on top of that you’re accumulating more rewards and you’re moving up the levels within that program and maybe you’re getting free upgrade, a late checkout, a, you know, a free breakfast. Those types of things along the way towards getting that, that free stay. So you’re getting a better travel experience as you’re working towards getting a, you know, a free vacation.

Chris: 10:43 Oh Nice. Nice. I like that.

New Speaker: 10:45 So, and then, so the next thing that part of that, when picking a brand that has the type of hotels that you like is in the locations that you like, like again, certain hotels or only in certain areas, right? My favorite hotel chain is Kimpton and they’re now part of IHG, but before they were an independent brand and they only had maybe 75 hotels and so as much as I love them, they only have locations in certain spots. So when I travel to cities that they, they weren’t in, I had almost had to have a backup, you know. And so again, it’s when you’re picking a brand, you want to find, find out all the different aspects of that program so that way you can say, OK, this is going to give me, I’d like to go to New York City, I like to go to Orlando, I like to go to Chicago. Whatever city that you’d like to go, make sure that they have, uh, they have the properties that, that you want to be able to stay at in those cities.

Chris: 11:39 OK, no, that’s a good point that to you mentioned there.

Lee: 11:39 So, so the next part is getting the right credit card based on the brand that you’ve picked. So if you picked Hilton, then you obviously want to have a Hilton credit card because you’re going to get a lot more benefits. It’s going, it gives you like a head start. If you think of like 100 yard dash instead of starting at the zero marker, you’re starting at the 20 yard line. So you’re getting that much faster towards the, towards the finish line by having the credit card. Because with that, a lot of times they’ll give you automatic status instead of starting out at the bottom, you’re starting out at like a silver or gold member, right? And then if you spend a certain amount on the card, sometimes they’ll give you a bump up to another level. Uh, they’ll give you a late check out, free breakfast, you know, all of the different benefits that go with that card. So it’s a, it’s a double whammy and it helps you, but on the good side instead of on the bad side.

Chris: 12:29 Yeah. You know, I didn’t realize that. How many perks came with having the credit card that goes with the hotel. In my mind I was like, Oh, you know, you get points towards the Free stay, but I didn’t realize you got like status changes.

Lee: 12:39 Yep, exactly. Exactly. And then on top of that, like if you, again, be careful with the credit card. I have a lot of credit cards because I’m more advanced than most people, but I don’t want people getting a lot on credit cards. If you think of like going to baskin Robbins, there are 31 flavors and then some of all these different credit cards and it’s easy to go, oh I want one of these, one of these, one of these don’t go overboard because that’s how you, that’s how you can get into debt if you’re not careful. So pick one or two that’s going to be situated for you. That’s going to help you achieve your goals and then stick with them and then later on when you get more comfortable and get more advanced with, with your strategy, then maybe can branch out and do a little bit different, but just pick one or two that’s going to, that’s going to do well for you and use that card every day for all your expenses and make sure it gets paid off at the end of the month.

Lee: 13:29 My, the other point, I was going to make the same thing with the airlines. Just like hotels have benefits. Airlines also have benefits when you go into the, to the airport and you’re going to go check a bag. You know nowadays they want to charge a 25 to 30 bucks for every bag that you want to check. Right? And then on top of that, you know, based on your status and things like that, you, you may have even one of the last people on the board, the airplane, but if you have the credit card, they’ll generally give you free checked bags. Sometimes the credit card, we’ll give you a discount if you’re buying any food or drinks on the airplane and it also gives me priority boarding, so you’re boarding ahead of people that even have a mid level status on the airline, you’re actually boarding faster than them because you were the one that has the credit card.

Chris: 14:11 I think that’s worth it alone right there because you know, southwest they’re pretty organized, but other lines when you hop out there it’s like, you know, it’s like a madhouse out there. Everyone’s just like huddled in a 500 person ball right at the door.

Lee: 14:26 They actually have a term for that. They call that gate lice because all these people that are standing there standing there in front of the way and you’re like almost like a running back trying to run through the offensive line and defensive line. Trying to make it to the airplane.

Chris: 14:43 I think that alone will be worth getting like an airline card that works with your goals.

Lee: 14:45 Exactly. And then the last step is, as much as we’ve talked about credit cards, now that’s not the only way. Some people either they, they’re trying to, to buy a house to try to, you know, um, get a loan for a car. Maybe they have bad credit right now they’re trying to work to improve that. Credit card is not the only way to earn miles and points when you’re, when you’re trying to build up for your, for the next free vacation. All these airlines and hotels actually have partners of which you can earn airline miles and hotel points with them. Most of the airlines have a shopping portals, so whenever you’re going to go buy something from target or Kohl’s or you know, any of the different stores that are out there. Instead of going directly to Kohl’s or target go through the airline shopping portal. You can just create like a little link up on your favorites. And that way you could just click instead of having to type it out every time. You go through their portal and now you’re earning airline miles and hotel points for every purchase that you’re doing. It doesn’t cost you anything extra, it’s just a way of earning extra miles and points for, for doing that.

Chris: 15:45 Can you use that?… Like if you go through one of these portals, can you use your credit card and get the points that you would get for using the credit card plus getting the, uh, the bonus for using the portal?

Lee: 15:56 See Chris I knew I liked you. You’re a smart guy. Yeah, now you’re double dipping. Now you’re earning miles and points from your credit card and you’re earning miles and points through that shopping portal. So they call that double-dipping. So now you’re accelerating your process towards getting that next free vacation.

Chris: 16:15 OK. All right. I need to, I need to take advantage of that because you know, um, I’ve heard, I heard of it but I never actually took any action to, to give it a try. So that sounds like a great way to kind of accelerate the process of getting more points so you can travel.

Lee: 16:25 Exactly. And then, so you have that right? And then say you’re going on vacation and you need to get a rental car. Uh, they also have partners with these rental car agencies and so sometimes you’ll earn 600, 1200, 2,400 miles or points by going through their link to register to get that rental car.

Chris: 16:25 Oh nice, that’s a huge.

Lee: 16:45 And you’re getting a little bit of a discount and stuff like that. Sometimes you have to look at it and say, OK, is it better to go through a costco travel or some of these other sites as far as getting the rental. But again, I look at it as don’t always go with the cheapest because sometimes you look at it and it’s OK, this is $65 for this rental or it’s $70 for this rental, but with this, this other rental, you’re getting 2,500 points. It’s probably worth it to spend the extra five bucks to get those extra points.

Chris: 17:12 Yeah, exactly. Exactly.

Lee: 17:14 So you just going to kind of weigh all the pros and cons, right? And do it that way. Um, the, the last one, I’ll just leave you with this and then obviously we can, uh, if people want to come to the site, I can, I can show him some other ways to earn extra miles and points, but the last one is take your credit card, your debit card, whatever it is that you use when you’re out there shopping and dining. And there are two programs that you want to sign up for. A one is called dosh and the other one is dining rewards. And so with those, uh, dosh gives you cash back when you, when you dine at participating restaurants and the other one dining rewards you basically, you pick your favorite airline, whether it’s southwest, American, whatever, and then you earn miles for dining at those restaurants too.

Lee: 17:56 So again, now you’re triple dipping, you getting cash back from dosh, you’re getting miles from dining rewards and you’re getting the normal miles and points that you’re getting from your credit card.

Chris: 18:04 Man, I think that’s a pro tip if I’ve ever heard one.

Lee: 18:07 There’s all these other strategies that again, aren’t out there trying to get a new credit card, right, because a lot of people, if you go to some of the websites, people are always pitching, hey, get this new credit card. Not Everybody needs a new credit card. You know, sometimes you need a better card, you need to swap it out, but once you get one that fits you, sometimes it’s better. It’s just easier and better just to stick with the one you got and trying to maximize the value out of, of what you’re already have.

Chris: 18:33 That’s a great point. And I think this is a great way to get started. I think you’ve highlighted some really great things to consider and think about as you’re getting ready. So just to recap here, we had Tip #1 was choose your destination. #2 was figure out how you want to travel. #3 was pick your favorite airlines or hotels and kind of stick with them so you can be consistent. #4 was pick the right card for your favorite place that you’ve selected or favorite methods of traveling and then #5 was to use these partner portals or these websites where you can, I guess, accelerate your potential to earn points. So I think this is a great way to kind of get started, jump in and um, you’ll be able to take these trips, these vacations for a much more reasonable and more budget friendly price for sure. So Lee thank you so much for stopping by and sharing these tips with us.

Lee: 18:33 Definitely, my pleasure.

Chris: 19:21 And for you, is there anything going on that you’d like to share before we wrap up and get out of here?

Lee: 19:26 Sure. So, two things for, uh, for the listeners. One, I created a landing page specifically for everybody here on Popcorn Finance. So you go to BaldThoughts.com/popcorn and uh, basically I have a page there. It helps you with some different resources as far as some articles. I recommend you starting out a reading. And then from there also we have a free email course right now that we’re, that we’re getting ready to launch. It basically tells you how to walk through this entire process of basically making your dream destination of reality. So it’s, uh, it’s seven (total) emails and every day it just walks you through the process of getting closer and closer to be able to book that, that dream vacation.

Chris: 20:06 I’m going to check that out too because from, from talking with you and the advice you’ve given me, I think it’s definitely great to have someone who’s been through it to help you with the process because it can get overwhelming. So all the help and advice you can get on this was definitely appreciated.

Lee: 20:21 Definitely. So, and then on there, there’s also a link, we offer a free travel consultation where it’s like half hour where we will talk to you, figure out what’s important to you. And from there I show you the right strategy as far as getting the right card, the right programs that are going to help you make those dreams a reality.

Chris: 20:42 And so yeah, for everyone, again, that’s BaldThoughts.com/popcorn and it’ll take you to that landing page where you can get some more advice and tips from Leah at BaldThoughts.com. So Lee thanks again for joining me. Appreciate it. And uh, yeah, definitely hope to connect again soon.

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