Entrepreneur, Hacker and Future Mad Scientist 🚀☕

Category: Travel

How We Spent Four Days In Oregon For $25

This is a repost of an article I wrote for http://10xTravel.com/ which you should absolutely subscribe to!


Hey guys!


I recently got back from a four-day trip to Oregon with my girlfriend. From hot springs to waterfalls to snow capped mountains, it was was an amazing adventure.


I had been sitting on some points for a while and finally had a short break from class, so we quickly decided to book a trip. The whole booking process took less than an hour.



As everyone knows, trying to make time to travel can be particularly frustrating, so we booked this three months in advance. As a budding entrepreneur, this gave me enough lead time to ensure I had everything in place so I could relax on my vacation.


For those who don’t think you can take the time away from work, I’m here to tell you that it is possible. With a little planning, you can not only take a great vacation, but enjoy it too!

How I try to sleep on a six hour flight at 6am


In total, we took six flights over the course of 5 days to get from Florida to Oregon and back. Thanks to this experience, I now know that I’m terrible at sleeping on planes.


Even after staying up the night before our 6am flight (for some reason), I still couldn’t sleep.


Pro-tip: staying awake for 28 hours is a terrible idea. Don’t do it.


Who knew it would be such a journey to fly from Florida to a small city in Oregon…



Here’s How We Did It


To book our flights, lodging and rental car, we used the following points:

  • Capital One Venture – 50,000 points
  • Chase UR (transferred to United) – 40,000 points



If you want to read the complete post, click here

[Goal Completed] Becoming a Travel Hacking Master

Another awesome goal knocked off my list this year! I’ve always been a massive fan of Jason Bourne. Not just the movies, but the skills and assets he has as a person.

Have you noticed how he just appears in a new city or country out of nowhere?

Someone is paying for his plane ticket and hotel rooms and judging by his relationship with the C.I.A., they won’t be helping out anytime soon.

So what’s the closest a normal person can get to that kind of location freedom? The amazing art of Travel Hacking given by Live Your Aloha! This is a unique hobby of accumulating massive amounts of miles and points that allow you to travel essentially for free with lots of fun.

It’s nothing like your uncle Bill who has built up 50,000 Amex points over ten years. Oh no, this is how to build a storage of millions of points over the course of a single year and traveling your heart out.

In the past I’ve written posts on how I get $500 in free travel every month or a pretty general overview of travel hacking and becoming a global spy like Jason Bourne.

The reason I feel that I’ve successfully completed this goal is because of a few things – I’ve accumulated roughly 200,000 points over the last year, took a weekend trip that would have cost $1,000 for only $100 with my girlfriend and have begun to write for a friends site (10xtravel.com) on this very subject. Needless to say, I’ve got this down.

travel hacking post

Our Weekend Trip To Savannah For $100 (Included a Jr. Suite, $118 dinner and $35 drinks at the bar, est. $1,000)

I’m now one step closer to actually being the real life Jason Bourne.

This has become a very strong hobby for myself and something I talk frequently with others about. I now have the skillset to travel anywhere, whenever I want.  

I’ll continue to build up my points stash for future trips and random musings around the world and share my methods, destinations and guides to all things becoming Jason Bourne.

How I Get $500 of Free Travel Every Month

Travel hacking is nothing new, but the way it’s being done today is vastly different than it was a few years ago. Sure, we’re still using rewards cards to get the free travel, but the difference now is manufactured spending. I recently teamed up with Bryce over at 10xTravel.com to learn a bit more about travel hacking and to start building my rewards points.


It’s hard to believe this is even a possibility, but it works very well and there is a massive community around travel hacking. Whenever I tell someone I travel hack, they automatically assume I “hack” airline websites for free travel…. Seriously? If that was the case, why on earth would I admit that? Aside from base assumptions people have about travel hacking, it’s a mindset that opens doors and allows you to see the world for what it really is. This whole thing is a game. Once you understand the rules and the variables, you can beat it with enough effort.


Bryce talks a lot about the myths of travel hacking and credit cards, but let’s get one thing straight here and now; Your credit score will NOT go down as a result of having many credit cards! As long as you a responsible and think of these cards as a utility, you will be fine. If however, you are not financially responsible, you may want to avoid travel hacking all together.



Signing Up For Your Card

I chose to sign up for Barclay’s World Elite card. Within 10 minutes I was approved (thank you good credit!) and was well on my way to reaching free travel. Barclay’s card offers 40,000 bonus points after you spend $3,000 within your first 90 days. The reason why I suggest you sign up for this card is because its rewards are not airline specific. As long as your points are from a travel related merchant, you’re good. You can use these points for an Airbnb stay, cruises, hotels and of course flights. A lot of versatility with this card and an easy entry point as your first travel hacking card.


It’s ultimately up to you which card you go with so do some research!


Head over to Bryce’s Suggestions and search for the card you want to use.


Pretty simple right?


Setting Up Your Manufactured Spending System


For some of you, including myself, spending $1,000 a month simply isn’t an option. I’m currently a full time student so my budget is fairly tight at the moment. So if actually spending that kind of money isn’t an option, how do we get the bonus points? We use something called Manufactured Spending or MS. Basically, MS is “spending” money on your travel hacking card and then putting that money back on that card to pay it off.


There are some fees involved so it’s important for you to know there is no such thing as 100% MS as of now. Maybe the future will be brighter. Even still, I ended up paying $45 to gain almost $500 in free travel. Worth it? Hell yea!


Here is how it works in a nutshell:


You buy a gift card at either Walmart (I used Walmart) or CVS and load $500 on to it. I did two at a time or $1,000 per transaction. Even though I loaded my gift card from my new credit card, it still looks like a grocery transaction so it counts towards reaching your minimum spend for the bonus. Now I have $1,000 I need to put back onto my credit card to pay it off. This is where the magic comes in! I signed up with Serve.com which is like a small online bank account supported by American Express. They will send you a debit card that you can reload at places like Walmart.


Typically in the same trip to Walmart, I’ll purchase $1,000 worth of gift cards or $500 GC x2 and then take it over to their money center to load them to my Serve account. Now I have the money liquidated and transferable. Through my online account, I simply bill pay that money back to my Barclays account and pay off the difference from the GC fee (typically $4.94 per card).


It seems complicated so let me sum it up for you: Buy $500 gift cards at Walmart, load them to your Serve account, again at Walmart. Bill pay that money from your Serve to your Barclays account to pay off the card. Continue until you reach minimum spend.


*There are maximums with Serve loads and how much you can buy in gift cards per day/month. Do yourself a massive favor and read Bryce’s post on how to effectively do this!


Scaling Up For Maximum Benefit

This is travel hacking at its fundamental level. Hell, this is the exact method used on a major scale to gain a million miles and travel the world for free. So where do you go from here? At this point you’ve already gained a minimum of $400 worth of free travel. All you need to do now is pick another great card and repeat the process until you reach your desired amount of points.


This whole system can be completed within a few weeks. Literally every single month you could repeat this system and gain massive points over the course of a year.


It’s important for me to mention that MS spending changes quickly at times. NEVER carry gift cards longer than a day or two. I liquidate them to Serve immediately after I purchase them because you never know when something can change. The one thing I can guarantee is that things will change given enough time and you don’t want to be left with $1,000 worth of gift cards you can’t send back to your credit card. Luckily Bryce is up to date and out with a new method within a week. Either way, do what I suggest and liquidate quickly!



Day Trip – Devils Den Florida

My girlfriend, her friend and I took a quick day trip to snorkel this amazing cave only a few hours from where we live. Check out the video!

I wish I had more pictures to share with you guys, but I’ll have more trips coming soon.



Travel Hacking: How To Be A Global Spy And Travel The World For Free!

When I first learned how to fly around the world for free, I truly felt….. well, free. I had never known of such amazingness that I could partake in as long as I was over the age of 18(Which I was). Imagine waking up, deciding your city just isn’t making the cut for today and you get on your laptop and pick a destination. For most people this alone is unheard of. How can someone just “decide” to leave their town the day of? We are of course assuming this person is not wealthy by any means but has achieved what I like to call REAL freedom. So imagine yourself waking up and doing the same. Where would you go too? The best part about this little story is, the person didn’t pay anything to get to his destination and chances are, it’s so cheap once he gets there to live, he ends up staying a whole two weeks. Now this all sounds great but lets get into the dirty gears of how this actually comes to happen. I quickly found just how detailed planning your “hacking” can be.


What Is Travel Hacking?

Travel hacking, as defined by Chris Guillebeau, is simply, “experiencing the world on a limited budget.” The travel and leisure industry plays up travel (especially international travel) as a luxury only the rich can afford. By using some tips, tricks, and loopholes it’s possible to travel across the world, or all the way around it for very cheap. There are many travel hacking strategies and tons of useful resources on the Internet, some of which I will share at the end of this post.

 So How Does It Work?

In order to gain location freedom and see the world on practically nothing, you are required to do a little leg work. We will be using Airline Frequent Flyer Miles to make all of this happen. don’t worry, you wont spend any extra money and you wont have to fly anywhere to actually get the miles.


Your first step is to figure out where you would like to go in order to start building your miles. This allows you to set a target mile amount to aim for. The best way to do this is to “hack”, don’t worry, no jail time will take place as it is perfectly legal to do this. Airlines and other major credit cards offer amazing mile bonuses for signing up for their cards. Obviously you need to be a good spender to make this happen and not go completely in debt. If your a complete idiot, chances are your not because your reading a article on travel hacking, then leave this article and save yourself. Now many people worry about their credit score being hurt for opening and closing so many credit cards. This is how it happens; Your score will drop roughly 1-2% at first and then, it will go up around 40 total points. That’s right, free flying and a better credit score. Don’t you love hacking the system for your benefit? I do.


Now if you are completely on a budget and want to do all of this leg work yourself, be my guest. This required countless hours researching forums and sites looking for deals and bonus points. I am assuming your like me saying, “Who the hell do you think I am? I wanna hack this shit and make someone else do it for me!”. I completely agree!

Can I automate This Process?

There are three services which completely(almost) automates this leg work for very cheap. Whenever deals and bonuses pop-up, you get an email and even a text for the really time dependent deals you need to do right this second.


The top three sites to use while building your miles are the following:

  • 10x Travel: The website I personally write for and learned the most from. Make sure to join the Insider Facebook group!
  • Boarding Area: A website that contains a series of blogs that discuss how to fly for free and gain airline miles and elite status quickly.
  • The Points Guy: Run by Brain Kelly, this site helps people navigate credit card bonuses and airline and hotel reward programs.

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