Confessions of a 23-Year Old Thousandaire

A Short eBook About Money & How to Make More of It in Your Twenties.


Some of you reading this right now, may be making $100,000+ a year, while others may be living at home with their parents. Regardless, it doesn’t really matter, what matters is whether or not you are getting money smart — or smart about money.

Our 20’s are not unlike driving on US Route 20 — which is the biggest highway in the United States spanning 3,365 miles coast to coast — some of us may be in the fast lane, some of us may be going 40 miles an hour and some of us may have a flat tire on the side of the road. Regardless, we are all going to the same place.

I wrote Confessions of a 23-Year Old Thousandaire because I am exactly that… a 23-year old that has a dozen or so thousands to his name. I am not a millionaire and I think that’s what makes this eBook special. I am not some dude worth millions of dollars, writing this book in front of my ocean view condo.

I am in your exact same boat — I am just trying to make $1 outta 15 cents.


Chapter One —

If You Are Nothing Without Money, Then You Shouldn’t Have It.


It’s good to have money and the things that money can buy, but it’s good, too, to check up once in a while and make sure that you haven’t lost the things that money can’t buy.
— George Lorimer

Last night, I was watching Spiderman: Homecoming at a local theatre in my hometown.

I was seated in the front row of the cinema — in the shitty seats that are so close to the screen you are forced to move your head back and forth to avoid missing anything — a task that becomes increasingly more difficult when you’re watching a high-flying web-slinging superhero.

Anyways, halfway through the movie, Iron Man (played by Robert Downey Jr.) and Spiderman (played by Tom Holland), had a conversation that was impactful enough to momentarily distract me from thinking about my stiffening neck.

The conversation took place shortly after Iron Man had to swoop in and save an overly-eager, 15-year old Spider-Man’s ass, who almost killed a couple hundred people while attempting to stop a bad-guy wielding massive robotic eagle wings named The Vulture (played by Michael Keaton).

It was a valuable mentor/mentee moment, where a disappointed Iron Man demands back the suit he had made for the young Spider-Man.

Iron Man: “I am going to need that suit back.”

Spider-Man: “But I am nothing without this suit!”

Iron Man: “If you are nothing without this suit, then you shouldn’t have it.”

If you were to replace the word “suit” with the word “money” in this dialogue, write it down, and remind yourself to look at it from time to time, you would be doing yourself some good.

In fact, if you don’t remember anything else from this entire book, remember this — if you are nothing without money, then you shouldn’t have it.

This is a lesson many people don’t learn until their 40’s and 50’s, and a lesson that some people unfortunately never learn.

Throughout the course of this book we are going to talk a lot about money, and talk even more about ways you can make a lot of money.

But, you should never forget that while it is fun to make money, save money, play with money and even share money with the people you love… money should never be how you define yourself and your worth.

My name is Cole Schafer, I am a 23-year old writer that loves a damn good book, a well-brewed cup of coffee, a cold beer, a warm conversation and spending time with the people I love. While I also like to make money, it is by no means who I am.

As long as I always have $25 in my pocket ($10 for a damn good book, $5 for a well-brewed cup of coffee, $5 for a cold beer, $0 for a warm conversation), I will be rich.

Anything I make after that… well, that just makes me fucking Bill Gates.

So, as we dive deeper into this book, always remember — if you are nothing without money, you shouldn’t have it.

While money is nice to have, once you start defining yourself by what is in your pocket, you will have never been poorer.


Chapter Two —

Stuff Some Money in The Mattress, Baby.


Try to save something while your salary is small; it’s impossible to save after you begin to earn more.
— Jack Benny

My late grandmother had $30,000 wrapped in aluminum foil, stowed away deep in her freezer the day my grandpa forced her to to go to the bank and open up a savings account.

My grandmother, affectionately referred to as Meme, was full-blooded Japanese and one of the smartest individuals I have ever had the fortune of being around.

When she was 20 years old, she fell in love with a sailor in the United States Navy who was stationed in Japan (my grandfather) — and as the story goes, she decided to follow him back to the U.S., marry him and start a family in a small town call Francisco, Indiana, population: 473.

My grandparents were dirt poor when they got married. I recall my grandmother telling me a story depicting just how poor they were. The first time she was traveling from Japan to the United States, she found herself in a bit of a predicament… she had to use the restroom.

Back in the 50’s, many public restrooms required that you slip in five cents to allow access to take a piss. My grandparents were so poor that they didn’t even have five cents on them at the time. So, my grandmother had to crawl under the door just to take a pee.

When you grow up poor like that, you are forced to get money smart pretty damn quickly… to avoid having to crawl under bathroom stalls to take a piss.

Thirty years later, after my grandmother had raised two kids of her own, who then went on to raise kids of their own (one of which was me)… my meme finally had quite a bit more money to her name.

She was always big on saving, and taught each of her grandkids the importance of it. By the time I turned 8 or 9, my grandmother took me straight to the bank, opened up a savings account for me and deposited $50 in it.

Every time I saw her, one of the first questions she would ask me in her Japanese accent was, “Are you saving? How much do you have in your savings? cole-san” (the Japanese have a habit of adding ‘san’ onto people’s first names).

After my beloved grandmother passed away years later from a massive brain-aneurism, my grandfather casually brought up one time that she had $30,000 in aluminum foil in her fridge. He said she was weird about putting her money in the bank, and that for some reason she felt safer keeping at least some of her dough in the fridge.

While I am definitely not recommending that you keep thousands of dollars hidden away in various parts of your house like a fat little squirrel smuggling acorns, I am telling you to save, save and save.

Mark Cuban, billionaire entrepreneur/investor and owner of the Dallas Mavericks was once asked about his thoughts on investing.

“Don’t”, was what Cuban had to say.

“The market could go up for years, and you could think you’re well off.” he told Entrepreneur Magazine, “and then, in a millisecond with high frequency trading, a flash crash can take it all away. That’s why you want to have that money in the mattress, so you’re protected in case something goes wrong.”

I think Cuban shares some great insight here. Granted, there is no way Cuban would have been worth the mind-boggling $3.4 billion that he is today, if he had just shoved all his money in a mattress, but his advice is still sound.

*** Keep reading, and I will share more of my thoughts on the investing side of things in the next couple chapters, but in the meantime… if you are interested in investing, I got a free stock waiting for you here.

But, back to savings. Let’s say you make just $500 a week for the next 10 years of your life. Yes, the chances of this are slim to none, but let’s just speculate here.

If you are able to save $50 out of every paycheck and shove it under your mattress, by the end of 10 years you will have saved $26,000.

That’s a thick mattress.

Personally, I take 50% of everything I make and place it in a savings account. The other 50% of my money goes towards my day-to-day expenses and standard 20-something things like eating too much sushi, drinking craft beer and going to the occasional music festival.

I recommend everyone to place a portion of their income in savings. Most financial advisors recommend 20% of after-tax income. If you can save more than that, great. If not, 20% of every paycheck accumulates into some pretty lofty sums quickly, if done religiously.

It is important to understand that your savings account places you in a position of power over your life.

You don’t like your job? Quit, and find one you do like. You really want to start that online knitting business you’ve been dreaming of since the age of 16? Do it. Are you ready to relocate to a different city? Start packing.

None of this is possible without building up a savings.

So, stuff some money in that mattress, baby.


Chapter Three —

Check Six.


“In the Air Force we have a rule: check six. A guy is flying along, looking in all directions, and feeling very safe. Another guy flies up behind him (at “6 o’clock” — “12 o’clock” is directly in front) and shoots. Most airplanes are shot down that way. Thinking that you’re safe is very dangerous. Somewhere, there’s a weakness you’ve got to find. You must always check six o’clock.”
— U.S. Air Force Gen. Donal Kutyna

One day, my best friend called me up, out of the blue, in shock, “Cole… I just got fired,”

It was on a Friday morning, exactly one hour after he had sat down at his desk. His supervisors called him into their office, told him it wasn’t working out, and then fired him.

He received no warning, no heads up, nothing. He was told to pack up his stuff, and just like that, he was out of a job.

Fortunately, he was only 23 years old at the time and still living at home with his parents. But, it didn’t change the fact that he was forced to deal with something he hadn’t planned for.

Everything worked out, in part because my best friend is pretty damn resilient and within 3 weeks, he had already found a job 1,000 miles away in Boston, offering to pay twice what he was making at his previous position.

Regardless, I can’t tell you how many times I myself or people I love and care about have been flying high, feeling good, feeling comfortable, and then all of the sudden… BAM!

Shot down, right out of the sky, from that son of a bitch called life.

Fortunately, we are not flying 39,000 feet above the ground, but nevertheless, getting shot down still stings.

While I am certain all of us are aware of what it feels like to hit the ground, it seems that we never hit the ground hard enough to shake our brains into remembering to Check Six.

When I played basketball in high school, my coach used to always say, “Don’t you dare get complacent… don’t you dare get complacent.”

He was always scared to death of his team getting too comfortable, terrified we were going to lose our killer instinct.

While business and life are beautiful in so many ways, make no mistake about it — it is no dance in the daisies.

The minute you’re caught sleeping, you will get knocked on your ass and that is why you have to check six.

The best way to check six is to make sure you have six months worth of living expenses saved up, and secured somewhere nice and warm.

There will be times when you feel tempted to grab for it when you are feeling in need of a vacation and hear the mountains or beaches calling, but don’t.

You will need it one day when you check six and find a nasty fighter jet about to fire a missile up your ass.

If you have prepared for this moment, if you haven’t gotten complacent, you can sweep the plane around, press a subtle fuck you against the windshield and then light him up. Always remember to Check six.


Chapter Four —

Budgeting is Bullshit


“I love money. I love everything about it. I bought some pretty good stuff. Got me a $300 pair of socks. Got a fur sink. An electric dog polisher. A gasoline powered turtleneck sweater. And, of course, I bought some dumb stuff, too.”
— Steve Martin

Once upon a time, a good pal of mine, named Roger, dated a girl that knew a ton about money and was practically a witch — we will never be for sure, but Roger and I both have the inkling that she may or may not be Satan’s very own personal financial advisor.

All in all, Roger and Nancy’s relationship was horrendously terrible. However, the one thing Roger always told me he got out of the relationship was a deeper understanding for money.

Roger’s ex, Nancy, was really big on budgeting. Just absolutely adored budgeting. I mean, practically got off to the idea of slapping together a spreadsheet that she could punch her expenses into on a monthly basis.

She budgeted for everything and approached her budget with Murphy’s Law always top of mind — what can go wrong, will go wrong.

For example: say she were in the midst of a morning run to hell and all of the sudden let slip a fat fart mid stride. Now, let’s say the cheek throttling force of the ass-wind were to knock her over and onto her knees, resulting in severe lacerations in need of stitches.

If this were to happen, she would be smiling ear to ear on her way to the hospital, because you better believe, she budgeted for a “Fart Whilst Running Expense”.

Do you know why she would be able to budget for this $500 Fart Whilst Running emergency medical expense?

Because for 4 weeks prior to her morning run, she would have ate nothing but white rice and black beans, saving a large sum of 500 $1 bills.

At face value, this seems like a pretty good idea… budgeting that is. Until you put two and two together and realize the whole reason she had the $500 Fart Whilst Running Emergency medical expense was because she made her life a living hell for 4 weeks as she lived on a diet consisting solely of rice and beans.

That’s right folks, the financial witch shot herself right in the fucking broom.

While yes, this budget first financially centered lifestyle allowed Nancy to save an insane amount of money, Roger and I never understood her way of thinking.

Why save so aggressively for the future, if you have to sacrifice living an enjoyable and comfortable life in the present?

I am here to tell you that for the most part, budgeting is bullshit. My God, I seriously hate the word — it gives me chills and not the good kind — the nasty kind you get when you are driving and come to the realization that a spider has just crawled up your pant leg.

Yes, I hate budgeting, but no, I am not advising you to throw your money around like Floyd Mayweather in a strip club.

Then, what the hell are you advising us to do, Cole?

I am advising you to make and save money while keeping in mind the reason money exists in the first place:

1. To create freedom for yourself and the people you love.
2. To create incredible experiences for yourself and the people you love.
3. To positively impact yourself life and the lives of the people you love.

In my opinion, anyone who tells you different is full of shit and doesn’t have the right mindset when it comes to money.

While I think it is extremely important to save your money (after all, I dedicated an entire chapter to it), I don’t think anyone should save and budget to the point of discomfort.

I am going to end on a bit of a grim note, but who cares — you can’t punch me through the screen.

One day, you are going to wake up and get hit by a car, receive some bad news from the doctor or be so damn old that you are just going to want to die… and when you are face to face with the grim reaper, so damn close that you can smell his breath, and you can see Roger’s ex-girlfriend balancing spreadsheets over his shoulder, what thoughts will be racing through your head?

Fuck, I could have gone without the $11.99 a month Netflix expense.

No. More like…

I really wish I would have spent some of my savings on that trip to Barcelona.

When it comes to life and money, it’s not unlike what the prostitute said to the bashful sailor staring awestruck at her naked breasts — you can’t take them with you honey, so get your money’s worth.


Chapter Five —

Make Your Money Work for You


“How many millionaires do you know who have become wealthy by investing in a savings accounts? I rest my case.”
— Robert G. Allen

The first real money I made investing was when I got my hands on a lesser known stock called Shopify (Ticker: SHOP), an online website builder that allows just about anyone to become a business owner over night.

I liked the stock so much that I bet my entire ass on it. I think I was worth a grand total of $5,000 at the time, and I decided to throw $4,000 of it on this $40 a share stock that no one was talking about.

But, I was certain it was going to explode.

Fortunately, I was right. I road that stock up to $70 a share — turning my $4,000 into $7,000 in less than three months.

I felt like Warren Buffett, minus the $76.7 billion.

Please keep in mind, this was an incredibly risky move and one that I don’t recommend to anyone, but I tell this story to highlight a broader more important lesson —

Make your money work for you.

In my opinion, the best way to do this is through making smart, safe investment decisions. Sometimes, you’re going to hit the fucking jackpot, like I did with Shopify, but most of the time your returns are going to be small — but small is good, as long as it is consistent.

Paul Samuelson, a famous American economist who liked to wear a bowtie and thick black rimmed glasses, summed up the correct approach to making smart investments well —

“Investing should be more like watching paint dry or watching grass grow. If you want excitement, take $800 and go to Las Vegas.”

The stock market is not unlike the casino. If you don’t take it seriously, you will get burned.

I have learned this the hard way.

After hitting a home run with Shopify, I got too big for my britches and had experienced a day where the stock market gobbled up $1,500 of my winnings.

Fortunately, I made the money back, but it taught me a valuable lesson —

Gamblers win big once, and that is why they are broke. Investors win small consistently, and that is why they are rich.

If you choose to start investing, look for small consistent gains. I personally use an app called Robinhood to invest. It’s one of the only trading apps that offers you to trade for free. And, since I think you are cool, I hooked you up with a free share… just follow this link.

But, unless you are willing to spend a lot of time educating yourself in stocks, I would recommend for everyone to invest in either mutual funds or ETFs.

Warren Buffett, literally the greatest investor of all time, recommends the Vanguard S&P 500… so, that’s where I would consider first.



Chapter Six —

The $100 Rule


Money is only a tool. It will take you wherever you wish, but it will not replace you as the driver.
— Ayn Rand

Give yourself a pat on the back, you made it to the final chapter of my eBook, which means one of two things — I am a damn good writer or you have twenty or so minutes to kill — my guess is it’s the latter. Regardless, thank you.

To close out this read, I want to share with you something I have recently implemented called the $100 Rule.

For the past year, I have felt like I have been pretty consumed by money, success and work — which I think has been instrumental in allowing me to build up a creative copywriting business and gain a decent following right here on Medium.

But, with that said… I think it has been a little bit detrimental too. When you get too consumed with your own path and your own success, you can forget about the people around you who are struggling.

Recently, I started practicing the $100 Rule.

Each month, I take $100 in cash out of my checking account and instead of spending it on shit I probably don’t need… I try and spend it on brightening up someone else’s day.

There is only one rule: It has to be spent on someone else.

Maybe this is giving your server a 50% tip, buying your mom flowers just because, or paying for someone’s Starbuck’s order in the line behind you.

It doesn’t have to be used to change the world, just make a small impact on the random lives you come in contact with…

But yeah, that’s all I have for today. I hope you enjoyed this read. If you signup for my email list below, you can get a weekly email covering stuff I don’t cover here on Medium.

By Cole Schafer

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