Travel Freedom will regularly feature Travel Hacker Interviews with people who are already travel hacking. The purpose of this series is to get a glimpse into the lives of people who are traveling by using points and miles. They will show how travel hacking is real and how it is for anyone.
Q: Tell us a little bit about yourself.
A: Hi, I’m Ryan. I’m from Eugene, Oregon where I’ve lived for most of my life. My biggest interests are my wife (obviously), traveling, sports, entrepreneurship, and crypto currency. As many of you know, I’m the founder of Travel Freedom where I’m teaching all of you how to use miles and points to travel without having to spend much money. Travel Freedom is fun for me because I get to combine two of my passions: travel and entrepreneurship.
Q: How long have you been travel hacking?
A: I’ve been travel hacking with points and miles since 2012 and have never looked back. My life has changed quite drastically due to my ability to travel without spending much money.
Q: How did you find out about this somewhat secret world?
A: This is a bit strange, but I’m sure many people who have found this community, have found it in a wide range of ways. In 2012 I had a cracked root in one of my teeth, which meant that I would need a root canal (eventually led to an implant -ugh) which was going to cost a couple thousand dollars. I was dreading both the procedure and the cost of it. I had remembered seeing ads for credit cards that would give you a chunk of money for opening an account, so I went to my friend Google. I searched and ended up coming across a few travel blogs which featured travel hacking.
I started reading them religiously and decided to apply for a Chase Sapphire Preferred card so that I would receive 50,000 points from the signup bonus after I paid for my root canal. I learned that using credit card points toward travel gives you a significant bump in the value received from the points. For instance, I used those Chase points on travel and my points ended up being worth about 2.5 cents each for a total of $1,250 just from that credit card signup bonus. If I had instead used those points as cash back or for gift cards, they would have given me a value of just $500.
Looking back, I’m not too mad that I had to have a root canal and implant, because it opened my eyes to the world of traveling with points and miles. It has allowed me to travel infinitely more than I would have been able to without this knowledge.
Q: What was the first trip you took using miles and points?
A: Maui, Hawaii
As a child I visited Hawaii a few times because my grandparents lived on Maui for about ten years. I fell in love with the islands then, and had wanted to revisit them as an adult. I was able to book my own round trip flight for just half of that signup bonus I received from my root canal experience.
Since then I have gone back to Hawaii seven times, visiting all the major islands. I love Hawaii and will probably visit once a year for the rest of my life. If you haven’t been, I suggest you go see what it’s all about.
Q: Have you ever had an amazing or crazy story come from travel hacking?
A: I’ll tell you two stories from my travel hacking journey. One that almost happened and one that did happen.
First the one that almost happened. You’ll learn that airlines and hotels sometimes have what are referred to as “mistake fares” where something may go wrong with their pricing for a short period. Travel bloggers often post these to social media and they are usually corrected by the airline or hotel very quickly. So, one day while I was at work I got a notification on my phone that United Airlines had flights to Hong Kong that were possible to book using just 4 United miles (the equivalent of about 8 cents). I quickly found some dates that I thought I would be able to travel and booked a round trip flight to Hong Kong.
Everything seemed good and I was even ticketed through email. But, with these mistake fares, sometimes the companies will honor them and sometimes they will cancel them. Unfortunately, they ended up canceling everyone’s tickets who got in on this mistake fare, but it was exciting while it lasted. I didn’t get to end up taking an 8 cent flight to Hong Kong, but it made me aware that these mistakes do happen and sometimes they do honor the pricing.
Now for the story that did happen. In 2015, some good friends of mine mentioned that they thought their other friend and I would get along very well. They gave me her contact information and we started talking non-stop and there was an instant attraction. The only problem was that she was currently living in Virginia and if you remember from the first question, I live in Oregon. Yeah, that’s 2,800 miles apart, making a first date a little tough.
No worries, I’m a travel hacker and had American Airlines miles out my A*$ from a credit card signup bonus and some promotions I took part in. So I booked my ticket to fly across the country for our first official (non Skype) date. The rest is history and we are now happily married and thankfully both live in Oregon!
*Disclosure: Results may vary – Becoming a travel hacker does not guarantee finding your soul mate across the country.
Q: What’s the best signup bonus you’ve ever received? Do you remember what you redeemed the points for?
A: I’ve had a few amazing bonuses through the years. The banks offering these credit cards with huge signup bonuses sometimes decide to run special offers for even more points or miles than usual.
The two cards that stand out the most are when I got 100,000 American Express Membership Rewards points for signing up for their Platinum card, and more recently when I got 100,000 Chase Ultimate Rewards points for signing up for their Sapphire Reserve card.
Both offers earned enough points for multiple vacations saving me thousands and thousands of dollars on travel. For instance, either of those signup bonuses are enough miles to book four round trip flights to Hawaii. That’s a lot of money saved!
Q: What do your friends and family think of your travel hacking hobby?
A: They are becoming more comfortable with it now that I’ve been doing it for so long. In the beginning I think they were a bit skeptical of how this was possible, and often wondered what the catch was. Now that I travel whenever and wherever I want for very little money out of pocket, and my credit score is just about as good as it can be, they are starting to ask how to start travel hacking.
Q: What are your future travel plans?
A: This year, my wife and I plan on traveling to Mexico with some of our family, New Orleans to see a friend, and California a few times to see family and for a wedding. My wife is a teacher (summers off) and I just took a job that gives me more flexibility to travel so we also have a lot of time available this summer to make even more plans. We could use some ideas, so send them our way!
Q: Do you travel hack for quantity or quality? AKA do you use your miles and points to travel as much as possible, or to travel more extravagantly?
A: For the most part I try to get the most bang for the buck (or in this case bang for the point). We usually travel in coach and try to squeeze out as much travel as possible with the points we earn. There have been a few times where we went for the extravagant travel, flying in first class or staying at resorts that normally would cost $500 a night, but those are more occasional. We like to venture out while on vacation, so the features of where we’re staying is less important and more just a comfortable place to relax and sleep.
Q: How often do you travel now, compared to before you knew what travel hacking was?
A: Before I knew about travel hacking I would maybe travel once a year due to the cost of flights and hotels. Since, becoming a travel hacker, I would say I average traveling 6-8 times per year. My wife and I plan on bumping that up a bit in the coming years, because we would like to travel as much as possible before we try to have children.
Q: Best tip for people just getting started on their travel hacking journey?
A: Make a plan, and then go for it!
When I started out I just jumped in and got every good signup bonus I could find, but then I had points just sitting in accounts instead of being used. Always remember that holding on to points has no value. If you’re going to earn points or miles, there should be an ultimate goal to use them in the near future.
Q: How can people contact you?
A: Right here on TravelFreedom.net
I would love for everyone to join my email travel journal to stay updated with us. Also, feel free to send me an email with any questions you may have. I’d be happy to connect with you!