Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!
Miles & Points Interview: Loophole Travel
Jesse started Loophole Travel to introduce fellow adventure seekers to the wonderful world of miles and points.
You can follow Loophole Travel on Facebook, Instagram, and Twitter.
Jesse and His Wife, Brooke, on a Doors-Off Helicopter Tour Overlooking the Na Pali Coast
How and when did you start collecting miles and points?
My 1st real exposure to the miles and points game came from my friend Jared, who writes the blog Thrifty Traveler. He tried a few times to teach me what he was doing, but I guess it all seemed “too good to be true.”
I finally decided to give it a shot in November 2014, when I nervously applied for 2 Chase Southwest Airlines credit cards to earn the Southwest Companion Pass. I believe I learned the specifics of earning the Southwest Companion Pass from Million Mile Secrets. So thank you very much!
Our pass arrived in early February 2015, and I was hooked!
Sunset at the Waldorf Astoria Grand Waliea, Maui
Why did you start your blog? What’s special about it?
Once I discovered how easily we could earn huge point balances and travel for free, I wanted to tell everybody!
After our vacation to New York City and Dubai for almost no money, our friends and family really started asking questions. Instead of answering the same questions over and over, I decided to create a place I could direct people to for answers. The blog basically grew from there.
I look at earning points and finding loopholes like a giant puzzle or a very lucrative scavenger hunt. It really fits my interests and skill set perfectly, because I love finding deals and thinking outside the box.
At Loophole Travel, we try to bring a fresh perspective on travel hacks, written with clarity, so even someone completely new to the hobby can jump on board.
What’s the one single thing people can do to get more miles?
STOP paying with cash or debit cards! This is big pet peeve of mine. When I see someone pull crumpled bills from their wallet to pay for lunch, I cringe and think of all the rewards they are missing out on.
Sign-up bonuses are great for earning big points, but simply using a rewards credit card for daily purchases could really make a difference for people.
Brooke Enjoying a New York-Themed Cocktail in the AMEX Centurion Lounge at LaGuardia Airport
What’s your most memorable travel experience?
It is really difficult to nail down a most memorable experience, because we have really been blessed with amazing opportunities in the past couple years. Mostly due to our reward points.
Let me give a quick top ten:
- Proposing to Brooke on top of a mountain in Colorado
- Swimming with Sharks in Moorea, French Polynesia
- Kayaking in Bioluminescent Bay, Puerto Rico
- Eating 24-karat gold for dinner in Abu Dhabi
- Swimming with Sea Turtles in Maui, Hawaii
- Watching the sunset from the Burj Khalifa in Dubai
- Dune bashing in the middle of the Sharjah Desert
- Camping out for free stand-by tickets to the Tonight Show in New York City (and making friends from Australia in line – Hi James & Carla!)
- Taking a doors-off helicopter tour of Kauai, Hawaii
- Spending 9 nights in an overwater bungalow in Moorea, French Polynesia
Wow, it really amazes me just to make that list. I think back a couple years to when travel seemed so expensive and unattainable. Now we can dream BIG knowing our points balance can get us anywhere in the world!
24-Karat Gold Dinner at Emirates Palace, Abu Dhabi.
What do your family and friends think of your miles & points hobby?
Most of our friends and family are EXCITED about these opportunities! We have already coached 8 or 9 couples toward earning the Southwest Companion Pass. So we will be planning a big, free trip together soon.
Also, my parents are now into the game, which allowed them to visit us in Kansas City for free at Thanksgiving. They have also earned quite a few American Airlines miles, which they plan to use for a dream trip to Europe in 2016!
Is there any tool or trick which you’ve found especially useful in this hobby?
One tool that we use regularly for booking hotels at the best point rate is Award-O-Matic. Simply type in the city, and select the hotel programs for which you have points. Color-coded pins will magically drop onto a map, and hovering over a pin shows the point requirements. Very useful!
View From the Top of the Burj Khalifa, Dubai
Additionally, Brooke and I recently visited 3 Hawaiian Islands and spent a couple of days in San Francisco and Sonoma Valley due to the generous routing rules on Korean Airlines.
We transferred our Chase Ultimate Rewards points to Korean Airlines to book Delta flights to Hawaii, and added a free stopover in San Francisco! All of this only cost 50,000 Chase Ultimate Rewards points for us both!
What was the least expected way you’ve earned miles or points?
A few weeks ago, Frank (1 of our awesome writers) told me about the IHG Priceless Surprises Promotion. I spent an evening compiling 188 index cards, stuffing envelopes, and printing labels for Brooke and me. If all goes according to plan, we should end up with at least 94,000 IHG points, hopefully more!
I also remember about this time last year, Hilton randomly decided to gift Diamond members 100,000 HHonors points. That was definitely unexpected!
Riding the San Francisco Streetcar
What do you now know about collecting miles and points which you wish you knew when you started out?
My biggest takeaway in my 1st full year is, the points and miles landscape changes constantly. For example, I waited a few months before getting an AMEX Target Prepaid REDcard. Had I known how much of a goldmine that was, I would have been more proactive. Now, when a new loophole opens, I try to get involved as quickly as possible.
What would your readers be surprised to know about you?
My readers may be surprised to learn that my homebrewed Jalapeño Pale Ale won a gold medal. I love to brew beer, and I even have a (less active) blog called Brew on a Budget, which is devoted to helping homebrewers save money. My top beers so far have been the aforementioned Jalapeño Pale Ale, a Peach Cream Ale, and a Vanilla Bean Russian Imperial Stout.
Camping Out For Free Tonight Show Tickets in New York City at 4:45 am
Any parting words?
Our team at Loophole Travel wants to encourage people to take action. Too many people get so bogged down in the what-ifs, that they never even try. I started out as 1 of those people, but I am so glad that I decided to just give it a shot.
In only 1 year, Brooke and I have been able to earn over 2.4 million miles and points! We could literally go anywhere in the world in First Class, a few times! Now, we can plan international vacations without taking away from our savings or preventing us from making charitable donations. Get in the game!
Snorkeling With Sea Turtles on Maui, Hawaii
Jesse – Thanks for sharing your thoughts on having Big Travel with Small Money!
If you’d like to be considered for our interview series, please send me a note!
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