Want to Earn 4 Free Flights Every Year? Learn From These Expert Travel Hackers

I’m betting most of you would jump on the chance to travel around the world for free. Who wouldn’t, after all?

But many people don’t take advantage of frequent flyer memberships and travel rewards cards. Whether actively or accidentally, they’re not involved in the world of “travel hacking.”

Why? Because getting from dream to dream vacation takes a lot of work. Many wannabe travel hackers end up disappointed when earning and redeeming points and miles takes more time or know-how than they have.

What if there were a service that made it easy for you? That held your hand through the complicated world of frequent flyer miles and rewards points and credit cards?

Meet Chris Guillebeau. At age 37, he’s already visited every country in the world — and he did it all using miles and points. Now he helps others fulfill their travel dreams with the Travel Hacking Cartel, a service he co-owns with Stephanie Zito and Tyler Tervooren.

Here’s how it works: Once you’re a member of the Cartel, you’ll receive alerts when lucrative travel deals, discounts and promotions pop up. You can opt for emails (between three and seven per week) or text messages (about two per week), or you can just log on to the membership site and see all of the deals at any time. You’ll also have access to travel hacking tutorials to help you better understand the world of miles and points.

Membership costs $1 for a 14-day trial, and $15-39 per month after that. It also comes with a unique guarantee: Earn 100,000 miles — enough for four plane tickets — in your first year of membership, or get your money back.

I sat down with Chris and Stephanie to chat about everything from why Chris started the Cartel, to the craziest ways they’ve earned miles and points, to how to start travel hacking from scratch.

When did you start travel hacking? Was there a lightbulb moment when you realized you were really on to something?

Chris: The first time I was upgraded on an international flight [to Paris in 2002], I was like, “Wow, there’s this whole other world out there. I want to do this again — but I don’t want to spend the $4,000 it costs for this ticket.”

Stephanie: I didn’t grow up traveling, and I always felt like travel was out of reach. My family drove to Florida twice a year from Pennsylvania for my entire childhood. I used to think, “If I get to go to Paris before I die, that would be the best thing ever.”

The few times in my early years that I was able to travel for free, it just really made it clear that travel was something that was accessible.

What led to you found the Travel Hacking Cartel?

Chris: I founded Travel Hacking Cartel way back in February 2010. I started it for two reasons:

1) I had had this project of my own of trying to visit every country in the world, which I eventually succeeded in — and I did that through travel hacking. It really made the whole thing very affordable and feasible to me in a way that it wouldn’t have been otherwise.

2) I had this great community of people that were asking a lot of questions about it… I felt that there was so much information out there, but it was very overwhelming.The whole goal [of the Cartel] is just to give people this turnkey program if you don’t want to spend 20 hours a month — like we do — searching for this stuff.

Are the majority of Cartel members redeeming points for aspirational awards — like Paris — or for simpler things, like visiting family?

Chris: I think people tend to transition… and their vision expands. Maybe at first, they want to visit their family in Iowa — but over time, they realize, “Holy cow, I’ve got all these miles and now I’ve learned how to best redeem them. And it’s actually going to be very cheap for me to go to Japan, or Ireland, or Australia, or somewhere else that before I’d never really thought much about.” The more people do it, the more they realize what’s possible.

What’s the craziest thing you’ve done to earn miles and points?

Chris: I did a hair loss appointment, even though I’ve got a pretty decent set of hair. If you made an appointment and had a consultation, you could earn 20,000 Delta SkyMiles.

I purchased more than $100,000 of dollar coins from the U.S. Mint (back when it was possible to  buy money at face value). You had to do it in installments, so I’d buy $3-5,000 worth of money and then go and deposit it at the bank. There was one time the UPS guy left $2,000 of coins on my front porch, and I live in kind of a busy neighborhood… I’m glad I found it and not somebody else!

I bought $5,000 worth of useless stickers once because they had a multiplier — so I spent $5,000 and earned 800,000 miles. I spent two and a half years flying around the world basically from that one purchase.

Stephanie: Once we bought an $8,000 refundable ticket we weren’t going to fly on — because there was a deal that if you bought a ticket, you could pay to multiply the miles. And they were two separate transactions, so if you bought a refundable ticket, then you could pay for the mileage multiplier, and once the miles credited to your account, you could cancel the refundable ticket and keep the miles. But it was a little nerve wracking because you had to sit on an $8,000 ticket!

What’s the craziest way you’ve spent your miles?

Stephanie: Chris and I just used miles to fly on the Emirates A380 with the shower on board in first class.

Did you use it? What was it like?

Stephanie: It was amazing! It had a hair dryer!

Chris: It was a shower at 40,000 feet! That’s a plane ticket that literally cost $25,000. Obviously, in a million years, we’re never going to spend $25,000 on a plane ticket.

But we were able to acquire these miles with credit card applications. I think we had to buy some extra miles (we spent about $500), so our total cost for that trip — it’s a 14-hour flight from Los Angeles to Dubai with a very exclusive cabin and nice lounge access on the ground — was less than $1,000 for both of us. That was 90,000 miles, and for only 10,000 miles more, we could add a stopover to anywhere in Asia — so we decided to keep going. We stopped off in Dubai, and then a few days later, we flew on to Singapore.

Stephanie: Not everyone wants to fly to Singapore in first class. The biggest takeaway is if you can figure out how to fly first class on a $25,000 plane ticket for essentially free, you can figure out how to go anywhere. Whatever that trip is that you want to take.

Let’s talk numbers: can you estimate how many miles you’ve earned? How many miles can Cartel members expect to earn?

Chris: We’ve served more than 20,000 people in the Cartel since inception. In a related course that Stephanie and I just taught, people earned enough miles in 45 days to take 23 one-way trips to the moon.

Stephanie: My dad has always been a business traveler, and he retired last year. He used to earn all his miles from flying traditionally. Once he started doing some of the things I was teaching him to do, he earned 300,000 miles in a year — which is three times what he was earning when he was flying every week for business. I would say an expectation is that you could easily earn 100,000-500,000 miles a year.

Chris: Yeah, I like that. The reason we have the 100,000 mile guarantee is it’s very specific and we believe it’s very obtainable. We do hear stories of people who earn a half million miles in a year, but that takes a little bit more time.

For me, over the past five years, if not more, I’ve earned at least one million miles a year. The point is the bulk of that is not through traveling. I do travel quite a bit; I go to 20 countries a year. But 200,000 of those are from travel and 800,000+ are through the different kinds of promotions we talk about in the Cartel.

How do you select the deals that end up in the Cartel?

Stephanie: A lot of the deals we do are things that people can take advantage of from different places: credit card bonuses, deals and discounts from hotels, online activities and quick deals.

American [Airlines] just had their own dream trip promotion, where you could watch six videos and get 1,000 miles. It’s quick stuff like this that if you weren’t paying attention, you would never see. And the beauty of what we do is that we pay attention. We hand-select these deals: if it’s not really good value, we don’t serve it to the Cartel. We do the thinking for you.

Our aim is to curate and serve up the best available and most applicable deals to our members — not bombard them with every single sale or promotion that is happening in the travel industry.

What’s the biggest misconception people have about travel hacking?

Chris: That it’s too hard or that the miles aren’t worth it anymore. People often say, “I had miles, I tried to use them for a trip, but the airlines said there was no seats available. It’s a game, and it’s rigged, and I can’t win.”

Stephanie: Airline miles aren’t impossible to use. It just takes a little bit of knowledge. If you understand the system enough to leverage the points you have, you can easily use them.

I know travel hacking is a lot of work — are there times when you wonder if it’s worth it?

Stephanie: If you care about travel, it is worth it. Once you set up a little bit of a framework for yourself, Chris and I call it “earn miles while you sleep.” You can earn miles through shopping and paying your bills — all these different things you don’t have to think about, but can still reap the benefits from.

What about people from outside of the US? Can they do much travel hacking, and can they join the Cartel?

Stephanie: We have people from 43 countries in the Cartel. One misnomer is that people think you can only do this if you’re from the US, because that’s where all the big bonuses are. I think it’s a lot easier if you’re in the US, but we’ve met so many people who are doing this — no matter where they’re from or where they want to go.

Is there anything else you want people to know about travel hacking?

Chris: This kind of world is constantly changing. That’s a big part of what we do in the Cartel: keep people up to date about this stuff. Because it does change month to month, sometimes even more often than that.

Also, we use the phrase “travel hacking,” which is obviously a little bit provocative — but we’re not really taking really advantage of travel companies or banks. This is a huge, huge business for them: They’re in the business of issuing credit cards and building long term relationships with consumers, and for the most part, they want people to earn miles. In some cases, if it’s difficult to redeem the miles, they’re the ones who have made it difficult. We’re just trying to help people better use the system.

Other than joining the Travel Hacking Cartel, of course, how can someone start on their miles and points journey TODAY?

Stephanie: Don’t try to do everything. Pick one trip you know you want to go on — something easy and attainable — and focus your mileage earning to begin around that.

When you look at all the information out there, and you want to do everything, it feels overwhelming. If you pick a place and starting point, by the time you’ve reached that goal, you’ve kind of learned the system and by that time, you’re ready to invest more time into bigger things.

Your Turn: Are you eager to start travel hacking?

Sponsorship Disclosure: A huge thanks to Chris, Stephanie and Tyler for working with us to bring you this content. It’s rare that we have the opportunity to share something so awesome and get paid for it!