“I Was a 220 Pound College-Recruited Middle Linebacker and I’ve Been Homeless Twice”
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Miles & Points Interview: Six Weeks to Sunrise
How and when did you start collecting miles and points?
In May 2011, I completed a 2.5 year bicycle tour across South America. What was supposed to be a sabbatical slowly evolved into the realization that I didn’t want to return to the office. From my apartment in Buenos Aires, I started Googling different ways to financially sustain my nomadic lifestyle.
Poker, English teaching, translating, and various online businesses were all obvious choices, but I was most attracted to the miles and points game because it seemed like the quickest and easiest way to eliminate my biggest travel expenses: airfare and accommodation.
From Argentina I applied for cards, received sign-up bonuses, and became obsessed with everything mile-related. Millions of miles later, I still view miles and points as tools that make a travel lifestyle possible.
Why did you start your blog? What’s special about it?
Turns out creating a financially-sustainable nomadic lifestyle doesn’t happen over night.
From Buenos Aires, I returned to the United States to pursue a business opportunity that flopped. Nearly broke and needing drastic change, I then moved to the booming oil fields of western North Dakota because the salaries were higher, companies provided food & housing, and rotating schedules were the norm.
When I landed a job with a 6 weeks on and 2 weeks off schedule, I began redeeming miles to all the places I most wanted to visit. Using miles to visit these 24 countries only reinforced my desire to be able to live and work anywhere. My blog documents this transition from employee to location independent entrepreneur.
In July, I’ll quit my oil field job to travel Eastern Europe, ride the Trans-Siberian railway from Moscow to Beijing, live in Southeast Asia, then find a job in Australia where I have a 1 year work visa. Of course I’ll write about my experiences in these 16 countries on my blog.
What’s the one single thing people can do to get more miles?
Listen to celebrities pimp Capital One’s double miles. Just kidding. Credit card sign-up bonuses are the most efficient way to stockpile miles. Nothing new there.
My strategy focuses on mapping out credit card applications 24 months in advance to ensure the hard inquiries are spread equally across credit bureaus and credit card issuers. More approvals, more sign-up bonuses, more travel.
In my opinion, being methodical with credit inquiries is the best way to keep the miles and points gravy train going. If this is a new concept to you, I offer a credit card application planning service on my blog.
What’s your most memorable travel experience?
My most memorable experiences don’t tend to be the postcard versions of the places I visit. Good people, good food, that’s why I travel now.
In Bolivia, I was invited into a family’s mud-brick home for the night. While potatoes boiled in a big black kettle the grandmother told stories in Quechua, laughing and smiling while the grandson interpreted in Spanish.
In the Ecuadorian Amazon, I camped outside a shaman’s stilted-hut for a week while participating in ayahausca rituals, which are believed to cure illness and offer enlightenment.
And in the Albanian countryside I drank homemade raki, a grape alcohol drink popular in the region, with a man who recounted how his father spent a lifetime building bunkers for a corrupt communist regime.
Motorbike rides in Hanoi, salsa nights in Havana, dinner parties in Lisbon…I could talk your ear off! Most of these memories would never have happened without miles. I feel fortunate beyond words.
What do your family and friends think of your miles & points hobby?
My brother thinks this hobby will land me in jail. And my coworkers think I’ll wind up in a Russian gulag. Most friends have no clue to what level I’ve taken this addiction.
My parents, on the other hand, are fascinated by what I do.
Recently I booked them business class to Moscow where we’ll begin our Trans-Siberian railway journey. Booking these free flights and luxury hotels (including the 5 star Radisson Royal Hotel in downtown Moscow) convinced my parents to get in on the action. I’ve since helped them be approved for 15+ credit cards while increasing their credit scores.
To my parents, buying gift cards to meet minimum spending is like a completing top secret missions. It’s a thrill, a game.
My mom dances a celebratory jig at home every time she scores a $500 reload card. I’m working with her on how to be more low-key and spy-like.
Is there any tool or trick which you’ve found especially useful in this hobby?
There is no shortage of free online resources for anyone wanting to take travel to a whole new level. Since the rabbit hole gets deeper by the day, I continually return to the tools that save me time.
For example, Mint tracks credit card spending and Awardwallet tracks loyalty program accounts. Feedly makes scanning hundreds of blog headlines easy. Milez.biz calculates and compares flight redemption rates of different frequent flyer programs.Wandr.me has a useful resource page. Deals We Like sends text message alerts about limited-time deals. And Loyalty Lobby lists current hotel promos and deals.
Most mile & point blogs also have airline and destination-specific Top 10 Redemption lists that are both inspirational and informative. Remember: Google knows all.
What was the least expected way you’ve earned miles or points?
When cancelling credit cards, I never expect retention bonuses because I’m not a big spender, so when agents validate my “valued customer” status with extra miles I’m always surprised. I also wasn’t expecting a recent transaction to be approved, now that CVS is no longer accepting credit cards as payment for Vanilla Reloads. But I was pleasantly surprised when it did.
In general, my earning strategies are deliberate so I don’t stumble upon too many miles and points that I didn’t specifically target. If you have the time and patience, shopping portals, dining reward programs, and checking evreward before shopping can be worthwhile to top off accounts. Especially when receiving bonuses for opening new accounts. Or multiple “new” accounts with different emails.
What do you now know about collecting miles and points which you wish you knew when you started out?
Hindsight is a…learning opportunity. When I 1st started applying for credit cards, I didn’t understand how to spread credit inquiries amongst credit bureaus and credit issuers, which negatively affected my credit score and ultimately lead to denials. That was a setback.
I also wish I would have spent more time on FlyerTalk to learn the ins and outs of this world. There are highly-protected, highly-encrypted loopholes discussed there that I’m only now beginning to decipher. Right or not, this is information that must be earned by throwing yourself into the learning curve.
I’ve recouped my time investment many times over with the knowledge gained. A recent $48, 1-way flight to Europe was a direct result of my FlyerTalk detective work.
What would your readers be surprised to know about you?
In a former life, I was a 220 pound college-recruited middle linebacker and I’ve been homeless twice. Once I shipped a street dog from Costa Rica to the United States. I spent the majority of my 20s in Latin America.
I know how to complete an undergraduate university degree for free (young people contact me!). I’m legally qualified to transport radioactive waste. I speak Spanish and Brazilian Portuguese but can barely order food in French. Turbulence still makes my palms sweat.
Any parting words?
You can fly most anywhere in the world for almost free, then stay in luxury hotels upon arrival. Let that sink in. Even though I’m living proof, it stills feels surreal. Get started now.
Learn how credit scores work, then how to spend at levels that are comfortable to you. Learn from Dararius, from other blogs, from my blog, from FlyerTalk, and then methodically target the credit card sign-up bonuses that will take you to your next destination.
Only after redeeming that first award seat will you realize the value in all this, that it’s possible to visit even the most far-flung, exotic locale without breaking the bank.
The truth is, this hobby won’t be around forever. And you won’t either. See the world while you can.Trevor – 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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Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)