Breakfast with Lisa & Josh #63 - Pudding Cups to Infinite Frequent Flier Miles

Breakfast with Lisa & Josh #63 - Pudding Cups to Infinite Frequent Flier Miles

Welcome Back to Breakfast with Lisa & Josh!

QUICK UPDATE: It looks like some people who were already subscribed to the newsletter weren’t able to get the links for the raw data and map from the latest video that came out today. Here they are -

Now, on to the email!

#62! I am floored, excited, and feel so, so lucky that each week, many of you who watch our YouTube videos also take the time to read each of these breakfast newsletters. Thank you, truly.

As I write this email, I wonder how many of you who read this newsletter either have or have ever wanted to just quit your job, sell everything you own, and travel the world? Ever since 2011, that’s all I’ve wanted to do. So much so, that I’ve done it 4 times over the past 11 years. I’m telling you this story in the hopes that it might help you if you’re thinking of doing something similar.

The first time that I realized that I needed something different, that I needed to sell it all and hit the reset button on my life was early 2011. I was sitting in a huge conference room filled with stressed out people, all pretending to care about this new phone deployment that we were about to start. Posturing, yelling, pointing fingers, intimidation - all tools used by people in the meeting to let everyone know that they were playing the corporate game better than anyone else. The corporate game that none of them actually cared about, but had to convince everyone else in the room that they did.

In that moment, in that stuffy room filled with stressed people, I saw my future. If I did my job well for 10 more years, that would be me on the other side of the table. Caring too much about building someone else’s dream. Losing my cool over an ultimately pointless phone deployment. Passing my anxiety along that I had accumulated over a decade of pretending to care about a company that did not care about me onto everyone that I worked with. The future looked bleak and terrifying.

I knew, then and there, that I needed to find a different path. Climbing the corporate ladder was a great option for others, but there’s no world in which it would work for me.

I left that meeting feeling empty. Feeling scared that I had already gone too far down that path to turn back - spent too much on college for a degree that I didn’t want to use anymore, lost my adventurous spirit that I had as a child, forgotten how to take risks. Worried that I would end up penniless and disappoint my parents by throwing away everything I had worked so hard for.

But still, even with the fear, I was certain that I needed to start planning an exit strategy as quickly as possible.

I knew that I needed a change, but I didn’t know what that change was. I was lost, looking for the right answer. Should I apply for this open position at a zoo? Should I go back to being a bartender? Go back to school to learn how to be a fire fighter?

My view of the options that I had for my life were limited. My family generally isn’t one to take risks, so I had never had a role model for the more entrepreneurial style of life. All the advice I had gotten along the way was “Be careful, don’t ruffle any feathers, get a good stable job, buy a house, settle down, get married, have a few kids, retire at 65, then maybe go travel.” That could not have been further from what I wanted. I wanted something very different, but had no idea what.

My view of my options in my life at the time was basically:

  1. Go learn something good enough so that someone will give me an opportunity

  2. Ask them for their blessing to tell me that I’m good enough to start making money

  3. Once they have given me their approval, start working and making money

It was basically the same system that I had left, but in a different field.

I wasn’t thinking big enough. I didn’t know what I didn’t know.

I didn’t even think it was an option to just bet on myself. To try something fully on my own, not caring about needing the approval of others. I didn’t know that I could just build the life I wanted all on my own. I thought I needed permission. From who? I don’t know - everyone?

Turns out, I never did need that permission. I just had to start.

It all came together when I read this article about a guy who found a way to get basically unlimited frequent flier miles by collecting pudding cups. There was a promotion going on - if you bought 10 pudding cups, and mailed in the UPC from the packaging, you could get 500 frequent flier miles.

He figured out that the pudding cups were much, much cheaper than the value of the miles, and went all in. He bought out every store within driving distance, even going so far as to have his local grocer order additional pallets of the pudding just to get more miles.

12,150 pudding cups later, he had amassed an absolutely bonkers 1,253,000 frequent flier miles.

This was impressive, but what really grabbed me was what he did with the miles.

He traveled the world, for free. Back and forth to Europe whenever he wanted. Off to Hawaii for a weekend. Why not book a flight to Tokyo?

It all became immediately clear to me. I wanted to travel the world. I had to do it. It was a foregone conclusion. I was willing to do anything.

I just had to figure out how.

What a legend.

That question of “how?” slowly turned into an obsession. I poured over FlyerTalk’s forums for hours and hours both at work, and at home. I built spreadsheet after spreadsheet projecting how many credit cards and how much money I would need to be able to do a 1 year trip around the world. Reading every single guidebook I could get my hands on to figure out how to reduce my costs to be able to leave as soon as I possibly could. It was all about getting on the road.

Then, things got a bit out of hand.

I applied for 10 credit cards in a single day. If everything went as planned, I should be able to earn a million miles and points, including 200,000 American Airlines miles which would be enough for the RTW Award Ticket they were offering at the time. I could choose 16 destinations, anywhere that American Airlines and their partners flew.

This was the answer. This is what I was looking for. If I could fly for free, then I just needed $15,000 to cover everything else for the year. I had found my purpose, my answer. There was hope. Another door had opened. A door that didn’t involve working in a cubicle for someone else forever.

The credit cards all had offers like “Spend $3,000 within the first 3 months of getting the card and get 50,000 frequent flier miles!” I’m sure you’ve seen those - it hasn’t really changed much in the past decade.

I would need to spend about $30,000 in 3 months to get all these miles and points. I started by buying everything for my friends, and having them pay me back. I figured out how to pay my rent via credit card for a small fee. I bought things at stores and then resold them on eBay. Anything to spend money without actually spending it, just to get closer to my goal of 1 million frequent flier miles and hotel points.

So, I thought back to the pudding guy. I had to figure out how to make it look like I was spending all this money, without actually spending it. Then, I found the manufactured spending forums, and stumbled across an idea that would change my life forever.

You see, at the time, the U.S. Mint was trying to get the $1 gold coin into circulation, to eventually replace the $1 bill. So much so, that they were offering to sell you these $1 gold coins, without any markup or shipping costs, $1,000 at a time. The most insane part? You could buy it using a credit card.

A lightbulb went off in my head immediately. I was buying $1,000 worth of legal tender - gold coins - via a credit card. I could then take those gold coins, and deposit them into a bank, and use that money to pay off the credit card that I had bought them on. It cost me nothing in the process.

And, at the end of all this, I would get the frequent flier miles. I could travel the world for free, just like pudding guy.

So, I did this over and over. Buying $1,000 worth of gold coins on my credit card (which weighed ~40 lbs), bringing them to the bank, convincing them that I wasn’t some sort of pirate that had just found a chest of gold coins at the bottom of the ocean, depositing that into my bank account, then using that money to pay off that credit card. Rinse, repeat.

3 months later, I saw something that I never thought I would see in my life. I was a millionaire. Well, a points millionaire. I had done it.

During this time, I sold off everything that I owned, and saved every penny that I could. It was a single minded effort - everything I did was about getting to take this trip around the world.

I saved up that $15,000. I quit my job. I was terrified.

I had also never felt so alive.

I went on that 1 year trip. I didn’t pay for a single flight the entire time. I found an entirely new life path. One that I didn’t know existed, or was even possible. The person that came home after that trip 1 year later was an entirely different person than the person who left.

I can’t honestly imagine my life if I hadn’t taken this chance. I probably would have made a lot more money had I kept with my job, but I also would have been a lot less happy.

I’d trade money for happiness anytime.

If you’re interested in doing something like this - leaving your job to travel the world - we have a bunch of videos on our channel that talk all about it. It’s not always a straightforward, linear or easy path, but it’s one that we feel so glad to have taken. If this is something you’ve been wondering a lot about, we would love to know—so we can talk about it and maybe help make that dream a reality. Just let us know.

Ok, this email has gotten pretty lengthy, I’m going to end it here. Thanks so much for reading this story - I hope hearing all this helped you in some way.

Until next week :)

Today

It feels weird to wrap up our 1 year trip/honeymoon with a Top 8 Things to Do in South Korea video or a budgeting video (even though everyone loves a good spreadsheet!) It is truly challenging to encapsulate what this year (and then some) has meant to us, but we are going to try. We are working hard on our second ever documentary, coming to you soon!

The (Near) Future

Today is also the day we figure out our future. We’ll let you know what we figure out next weekish (hopefully.)

Videos This Week

The Surprising Real Cost of Traveling Around The World

Exactly, precisely, down to the penny. This is how much a 1 year trip around the world costs.

Top 8 Things to Do in South Korea

Top 8 Things To Do in South Korea. You know what it is.

See you next Sunday…ish :)

- josh (and lisa)

Oh, and if you want to learn how we afford to take all these trips after quitting our jobs last year, you’ll likely be interested in our Skillshare course on Travel Hacking and Frequent Flier Miles. It’s been really taking off lately, but we still have a few uses of this link left for those of you who want to see the class for free. It comes with a free month of Skillshare, which is more than enough to watch our class and any of the other great courses on there!

Bonus Dog Content

This is Fenris. He’s a retired sled dog whose job is to protect humans from polar bears