9 Little Known Secrets for Hacking the High Life

By Sean Ogle •  Updated: 06/05/12 •  7 min read

Today marks the release of my biggest product for 2012: Hacking the High Life goes live at 9am PDT.  Learn how to create incredible stories while living the luxury lifestyle for free.  The first 100 members get special access to a Q&A webinar where I’ll help you work to achieve some of the experiences you’ve always thought were out of reach.

While many of the things I’ve learned about how to live the luxury lifestyle for less can’t be stated publicly (HTHL members only), there are a wide variety of different tactics, and tricks that you can easily apply to have some really cool experiences.

Many of these I’ve learned from trial and error, and others are cool tricks that I’ve learned from people much smarter than I am.

1) You can pay your taxes with a credit card

How on earth can knowing this help you Hack the High Life? Quite easily actually.

You see, if you owe taxes in any given year, you can use a credit card to pay which helps you earn airline or hotel miles and points.  For instance, I recently picked up the Chase Ink Bold card (this has to be the best business card out there) however in order to get the 50,000 reward point bonus, you need to spend $10,000 in the first three months – that’s a lot of money!

Well if you owe taxes, you can pay for it with the card and be good to go.  Unfortunately (or fortunately depending on how you look at it) I owed nearly $10k in 2011 taxes and 2012 quarterlies this past April. At least if I have to drop a lot of money on taxes I’m getting some bonuses out of it.

Consider looking for new cards and offers around the time you have to pay your quarterly business taxes to help you get there quicker.

One thing to note is that there’s a good chance you’ll have to pay a fee in the 1.5 to 3% range, but depending on your card miniums it could still be very worth it.

Just paying personal taxes? Grab the Chase Sapphire, the personal version of the Bold Ink and another incredible rewards card.

2) You can get into clubs much easier, simply by calling ahead

This one may not always work depending on exactly where you’re going and which nights, but almost always I’m able to get on a guest list at clubs in Vegas or NYC just by calling ahead.

Tell them you’re bringing some business clients out and give them a good reason for why you want to go to their establishement.  Tell them you’ll have an equal number of guys to girls (even if you don’t) and almost always they’ll add you to the list, allowing you to skip the line and usually not pay.  This works great at some of the larger clubs in Vegas (HTHL members will get two full posts devoted to how to do Vegas on the cheap.)

3) PR representatives want to help you

Almost any major hospitality or tourism related organization has a significant budget they can put towards media, exposure, and comps.  The PR people working for these companies want to hook you up – as long as they’ll gain something from doing so.  It’s your job to figure out what you legitimately have to offer these companies.

Have a big mailing list with a targeted audience? Tell them about it!  Own a business in a resort town? Strike up a special offer for your customers.  If there’s a way you can offer a hotel, ski resort, amusement park, golf course, restaurant etc. something that will expose them to a bigger audience, give it a shot.  You may be surprised by what you’ll get in return.

4) Building Rapport Goes a Long Way

Even more important than offering PR people something compelling to give them exposure, is getting them to like you.  When people like you, they naturally want to help you.  Get to know the people you want to work with, or that have the potential to hook you up with deals.  Do so genuinely without trying to get anything in return.  Offer to help them wherever possible.  You’ll be surprised just how much you’ll get in return.

5) You can stay in 4 star resorts for cheap by using Hotwire

I’d never used Hotwire until this past summer.  I was roadtripping from Portland to Colorado and ended up needing a place to stay for a night in Fort Collins and Denver.

Since exact location wasn’t a huge deal, I decided to give this whole Hotwire thing a shot. You basically pick your star level, general location, and it will give you a ridiculously good price on a room.

We ended up getting one of the nicest places in Ft. Collins for about $65.  The following night we got the same price for a 4 star golf resort near Denver.  I’d use Hotwire again in a heart beat to get luxury hotel stays for the same price as a Ramada right off the freeway.

6) Get Unlimited $50 Certificates from Expedia

Hotwire still too spendy for you?  Well then I guess we’ll need to get even more creative.  My friend Mike Hrostoski taught me this little trick to get a virtually unlimited amount of $50 gift vouchers for Expedia.

Essentially with their lowest rate guarantee, if you book a room through them and find a lower rate elsewhere, you can cancel the booking and the’ll send you over a $50 gift card.

On a recent road trip from NYC to Austin, we used this little trick to lock down a room in Texarcana, Texas for a grand total of $7.93.  Yes, I know, Texarcana really is becoming a new luxury hotspot.

You can check out this blog for Best Rate Guarantee arbitrage opportunities.

7) Get Free Office Space (Almost) Anywhere in the World

Regus has a pretty cool concept going.  They have thousands of office spaces all over the world (there are 4 alone here in Portland) and members get access to all of them.  For an annual fee you get access to any of their locations where you get essentially a coworking space, free internet, and free coffee.

Need a place where you can get some reliable business services, or perhaps hold a meeting?  Regus has you covered.

If you go to this link, and type in the activation code “pnf” you’ll get access to a free 6 month membership.

Thanks to Maneesh for originally telling me about the company.

8) Timeshares can be cheaper than you think

When you own a timeshare you can essentially trade the time you would spend at your own timeshare, and go some place else with minimal fees.  There are a couple main companies that have a database for what’s available and when.  You have to be flexible based on what’s available, but these deals are quite possibly the best you’ll ever see.  Think 7 nights on a beach in Maui for $199 total. 

Travel to Go has a deal where you pay a fee, and have the ability to rent from these pools of timeshares that aren’t being used.  It isn’t cheap for unlimited access, but once you have access, it’s yours for life.  The site looks a little sketchy, but I’ve talked to a couple people who have had some pretty incredible trips through it.

9) Stay in a Tropical Oasis for Free

I remember the day my buddy Andrew showed me the photos of the place in Mexico that he’s staying for free for the next 6 months – they were incredible.  There are a few different “house sitting” sites out there, but House Carers seems to be one of the best. There are homes literally all over the world where people need house sitting for anywhere from a week to 6 months.

If you’re flexible on exact location and dates, you could end up getting the place of your dreams for free – as long as you’re willing to do a few chores and perhaps a little pet sitting and gardening.

If these types of deals are interesting to you and you want lots more, check out Hacking the High Life.

Photo Credit: Nomadic_State_of_Mind

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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