5 crazy things I’ve done for miles and points

I recently hit my 5-year blogging anniversary, which made me reflect on some of the strange and crazy things I’ve done to earn miles. In general, this hobby is a little odd. The fact that some people fly around the country, checking in and out of hotels just for points and status? Strange. Churning hundreds of thousands of dollars in gift cards for airline miles? It sounds crazy to a lot of people.

Regardless of how outsiders see this hobby, we’ve all done things for miles that appear completely insane…even to us!

There are lots of colorful characters in this hobby who have carved out names for themselves doing crazy things for miles. There’s Steve Belkin, who hired Thai rice farmers to mileage run for him, earning him millions of miles. The shocker? The U.S. Drug Enforcement Agency sat him down to get to the bottom of what they thought was a drug smuggling operation. Upon learning it was really just a way to earn frequent flyer miles, they wanted in on it!

Then there’s David Phillips, who earned himself the Pudding Guy moniker after buying over $3,000 worth of pudding to generate millions of frequent flyer miles. Have you attended the Chicago Seminars in recent years? You may have run into Ray, whose credit card churning habits put all of us to shame (he churned the Amex Black card. Enough said).

Nothing I’ve ever done comes even close to what these guys did, but I thought it would be fun to reflect back and compile my own list of strange things I’ve done for points and miles. The list is really endless, so I’ve narrowed it down to my top 5:

5. Mattress running during Club Carlson’s Big Win Promotion

One of the craziest things I’ve ever done for miles (or so I thought, at the time) was mattress running during the 50,000 point Club Carlson Big Win promotion. It was my first mattress run and convincing myself to go through with it was a battle. But once I decided to do it, I went all in. I banked over 550,000 points from 11 nights and it opened up the door for me to take more risks in this hobby.

After that, buying thousands of dollars worth of Vanilla Reloads, ordering $4,000 in Visa gift cards from Staples (then unloading them at Walmart in $200 increments), and meeting $82,000 in spending requirements seemed like a cakewalk.

4. Earning 100,000 miles from Fidelity brokerage accounts

About six years ago, Fidelity was running an incredible promotion: Open a brokerage account, deposit $100,000 and get 50,000 airline miles. What made this even more amazing? The fact that you could get two brokerage accounts! One that earned Delta SkyMiles and another that generated American or United Miles.

I didn’t know better at the time, so I picked American miles…and almost had a nervous breakdown trying to redeem them for flights to Europe. What makes the Fidelity airline miles deal so crazy is how I approached it. I opened a total of eight brokerage accounts for myself, my parents, and brother.

Lots of people were able to get in on this deal because Fidelity didn’t require a single $100,000 deposit to earn each 50,000 mile bonus, but rather a total of $100,000. I know people who deposited and withdrew the same $10,000 – $50,000 until they hit the $100,000 minimum. The bonus posted pretty much right away.

For someone who was fairly new to the game, it seemed crazy to open eight brokerage accounts and deposit/withdraw so much money into each one. But I did it and everything I did to earn miles after that seemed totally normal in comparison.

3. Getting multiple Citi AAdvantage cards

One of my first credit card churns involved the 2-browser trick and the Citi AAdvantage Platinum Card. It seemed completely crazy when I heard about: Would it actually work? How would I meet the $6,000 spending requirement? How would it affect my credit? All of my fears were unfounded and I walked away with the easiest 150,000 miles I’ve ever earned.

Then another opportunity came up that I couldn’t pass up: The 100,000 mile Citi AAdvantage Executive Card bonus. The $450 annual fee wasn’t fully waived on this card. But we’re talking about 100,000 airline miles, so I didn’t care. I was planning a trip to Asia and each sign-up bonus would almost cover one person’s roundtrip airfare on Cathay Pacific business class.

I got a total of five cards for myself, my dad and brother. That left me with $50,000 worth of spending requirements to meet, which luckily turned out to be easy (and profitable) thanks to Loyal3. Getting five credit cards and then meeting the $50,000 spending requirement by purchasing stocks was by far one of the craziest (and riskiest) things I’ve ever done for miles.

2. Sending out 470 postcards for IHG Priceless Surprises

Two years ago, IHG Rewards Club ran their Priceless Surprises promotion, which seemed like a normal promotion at first. Then word got out that IHG was giving out points for mail-in entries – no hotel stays required. Members could earn at least 500 points per entry, for up to 94 entries. I mailed out 470 entries and earned 243,000 IHG points. Total cost? $250.

To give you some context, 243,000 IHG points can be redeemed for up to 48 Pointbreaks hotel nights or four nights at a top-tier hotel like the Intercontinental Paris Le Grand.

Of all the things on my list, I think this is the one I still look back on and think, “that was insane!” It’s also the one that incites the most laughter from other people. But it was a fun project and if the opportunity came around, I would absolutely do it again.

1. Churning Starbucks gift cards

Churning Starbucks gift cards is the one thing on this list that I probably wouldn’t repeat. In fact, it’s the only thing I still think is crazy. Like 2007 Britney hitting a car with an umbrella and shaving her head crazy. Here’s how it worked: There is a consumer protection law in California that allows people to cash out merchant gift cards with balances under $10.

Got a Target gift card with a $8.95 balance? Take it to the customer service desk and they’ll give you cash for it. If you return an item under $10 that you don’t have a receipt for, the register usually prompts a cash return.

A few years ago I heard about people buying $10 Starbucks gift cards from Staples to earn 5x Ultimate Rewards points with the Chase Ink Plus card. Sounds simple, right? They would load $1 of the balance to their Starbucks accounts, then cash out the remaining $9 at Starbucks.

It was pure torture. Time-consuming and painful, due to the occasional plastic cuts. I think I churned $1,500 worth before coming to my senses and deciding there were easier ways to earn free airline miles. Plus, death by a thousand plastic cuts seemed like a bad way to go, so I threw in the towel. This was by far the craziest and stupidest thing I’ve ever done for miles.

Nowadays, I wouldn’t think twice about picking up two credit cards, booking a dozen hotel nights (never even checking in), and spending $50,000 on gift cards in a day. Back then I would think long and hard about it. When I come across an unusual mile-earning opportunity, I jump right in. After all, I have many regrets when it comes to this hobby. Most of them involve things I didn’t do.

What’s the craziest thing you’ve done for miles? Share your stories in the comment section.