Yet a surprising number of people don’t take full advantage of frequent flyer programs and travel rewards credit cards. Whether by choice or by accident, they aren’t participating in the realm of “travel hacking.”
Why is that? Because turning a fantasy trip into reality often requires a fair bit of effort. Many aspiring travel hackers end up frustrated when earning and redeeming points and miles demands more time or know-how than they possess.
What if there were a service that simplified the process for you? One that guided you through the often confusing world of frequent flyer miles, rewards points and credit cards?
Enter Chris Guillebeau. By age 37, he had visited every nation on earth — and he accomplished it largely through miles and points. Today he helps others achieve their travel ambitions with the Travel Hacking Cartel, a venture he co-runs with Stephanie Zito and Tyler Tervooren.
Here’s the model: After joining the Cartel, members get alerts when valuable travel deals, discounts and promotions surface. You can choose email alerts (roughly three to seven per week) or texts (about two weekly), or simply sign into the members-only site to view all deals at any time. Members also gain access to travel hacking lessons that demystify the miles-and-points landscape.
Membership is $1 for a 14-day trial, then $15–39 each month afterward. It also includes a distinctive promise: Earn 100,000 miles — enough for about four plane tickets — in your first year of membership, or receive a refund.
I talked with Chris and Stephanie about everything from the Cartel’s origins to the wildest ways they’ve amassed miles and points, and how someone can begin travel hacking from square one.
When did you begin travel hacking? Was there a turning point when you realized you’d found something big?
Chris: The first time I was upgraded on an international flight [to Paris in 2002], I thought, “Wow, there’s a whole other experience here. I want to do this again — but I don’t want to pay the $4,000 for this ticket.”
Stephanie: I didn’t grow up traveling, and travel always felt out of reach. My family drove to Florida twice a year from Pennsylvania throughout my childhood. I used to think, “If I get to go to Paris before I die, that would be the ultimate.”
The few occasions I managed to travel for free early on made it crystal clear that travel could be attainable.
What inspired you to start the Travel Hacking Cartel?
Chris: I launched Travel Hacking Cartel back in February 2010 for two main reasons:
1) I was on a personal mission to visit every country in the world, which I eventually completed — and I did it by leveraging travel hacking. It made the entire endeavor far more affordable and feasible than it otherwise would have been.
2) I had an engaged community asking tons of questions. There’s so much information out there, and it can be overwhelming. The Cartel’s purpose is to offer a turnkey solution for people who don’t want to spend 20 hours a month — like we do — tracking down these opportunities.
Do most Cartel members redeem points for bucket-list trips like Paris, or for more practical travel like visiting relatives?
Chris: I think people usually evolve. Initially, someone might redeem points to visit family in Iowa — but over time they discover, “Wow, I’ve got a pile of miles and I know how to make the most of them. I can go to Japan, Ireland, Australia, or other places I never considered before.” The more members engage, the more they see what’s achievable.
What’s the wildest thing you’ve done to rack up miles and points?
Chris: I scheduled a hair loss consultation, despite having a fairly full head of hair. At the time, booking a consultation could net you 20,000 Delta SkyMiles.
I also bought over $100,000 worth of dollar coins from the U.S. Mint (back when purchasing currency at face value was permitted). Because purchases had to be done in installments, I’d buy $3,000–$5,000 and then deposit it at the bank. Once a UPS driver left $2,000 in coins on my porch — in a busy neighborhood — and I’m grateful I discovered it before someone else did!
I once spent $5,000 on what amounted to worthless stickers because the promotion included a multiplier — that $5,000 purchase earned 800,000 miles. For two and a half years I essentially flew the world on the back of that single buy.
Stephanie: One time we purchased an $8,000 refundable ticket we had no intention of flying on because there was a promo where buying a ticket and paying for a mileage multiplier — two separate transactions — would earn miles. Once the miles posted, we canceled the refundable ticket and kept the miles. It was nerve-racking to temporarily sit on an $8,000 booking!
What’s the most outrageous way you’ve used your miles?
Stephanie: Chris and I redeemed miles for Emirates A380 first class, complete with an onboard shower.
Did you actually use the shower? What was it like?
Stephanie: It was incredible — it even had a hair dryer!
Chris: It was literally a shower at 40,000 feet. A ticket like that can retail for roughly $25,000. Never in a million years would we spend that kind of money on a flight.
But we earned those miles through credit card sign-ups and promos. We bought a few extra miles (about $500), so the total outlay for that experience — a 14-hour flight from Los Angeles to Dubai with premium ground lounge access — was under $1,000 for both of us. The award cost 90,000 miles, and for 10,000 more we could add a stopover somewhere in Asia — so we extended the trip to Singapore a few days later.
Stephanie: Not everyone aims to fly to Singapore in first class. The key point is if you can find a way to fly on a $25,000 ticket for essentially free, you can work out how to get anywhere. Whatever destination you personally dream of.
Let’s talk figures: any estimate of how many miles you’ve earned? What should Cartel members expect to accumulate?
Chris: We’ve assisted over 20,000 people in the Cartel since we began. In a related course Stephanie and I taught recently, participants earned enough miles in 45 days to take 23 one-way trips around the moon — figuratively speaking.
Stephanie: My father used to travel for work constantly and earned miles by flying. After he adopted some of the strategies I shared, he accumulated 300,000 miles in a year — three times what he used to earn when traveling weekly for business. I’d say members can reasonably expect to earn between 100,000 and 500,000 miles per year.
Chris: I agree. The 100,000-mile guarantee is specific and realistically achievable. We do hear stories of people earning half a million miles in a year, but that usually takes more effort.
For me, over the last five years or more, I’ve earned at least one million miles annually. The majority of that total didn’t come from flying. I travel to around 20 countries a year, which accounts for roughly 200,000 miles, while 800,000+ miles have come from the various promotions we discuss within the Cartel.
How do you decide which deals to include in the Cartel?
Stephanie: Many of the offers we highlight are things people can access in different ways: credit card sign-up bonuses, hotel promotions, online tasks and quick-win deals.
For example, American Airlines recently ran a promotion where watching six short videos earned you 1,000 miles. These quick opportunities are easy to miss if you’re not paying attention. The advantage of our service is that we curate these offers — if something doesn’t represent good value, we don’t push it to the Cartel. We do the legwork for you.
Our goal is to curate and present the most useful and pertinent deals to members, not to overwhelm them with every single promotional blip in the travel industry.
What’s the biggest myth people have about travel hacking?
Chris: That it’s too complicated or that miles no longer deliver value. People say, “I had miles, I tried booking a trip, but the airline claimed no seats were available. It’s rigged and I can’t win.”
Stephanie: Airline miles aren’t impossible to use — they simply require some know-how. If you understand the system enough to leverage the points you have, you’ll be able to redeem them effectively.
Given the workload, are there times you question whether travel hacking is worth the effort?
Stephanie: If you care about traveling, it’s absolutely worth it. Once you create a simple framework — what we call “earn miles while you sleep” — you can accumulate points through shopping portals, bill payments and other routine activities. These are things you don’t have to micromanage yet still benefit from.
How about people outside the U.S.? Can they get into travel hacking, and is the Cartel available to them?
Stephanie: We have members from 43 countries in the Cartel. A common misconception is that this only works if you live in the U.S., where most huge bonuses tend to be. It’s certainly easier in the U.S., but we’ve met many people doing this from a variety of countries and destinations.
Anything else you’d like people to know about travel hacking?
Chris: This space changes constantly. A big part of what we do in the Cartel is keep members informed about those shifts — because promotions and rules vary month to month, sometimes even more frequently.
Also, while the term “travel hacking” is attention-grabbing, we’re not exploiting banks or travel companies. This is a massive industry: companies issue credit cards and try to build long-term customer relationships, and often they want people to earn miles. Sometimes redemptions are made difficult by the companies themselves. We simply aim to help people use the system more intelligently.
Aside from joining the Travel Hacking Cartel, how can someone begin their miles-and-points journey TODAY?
Stephanie: Don’t try to tackle everything at once. Choose one trip you genuinely want to take — something realistic — and concentrate your mileage-earning efforts toward that goal.
When you try to absorb all the information and pursue every opportunity, it becomes overwhelming. Pick a destination and a starting point. By the time you reach that objective, you’ll have learned the basics and be ready to invest time in larger strategies.
Your Turn: Ready to begin travel hacking?
Sponsorship Disclosure: Many thanks to Chris, Stephanie and Tyler for collaborating with us to bring you this piece. It’s not often we get to share something so valuable and be compensated for it!
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