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Eight Ridiculously Stupid Things That Cost Me a Lot of Money

by | Aug 22, 2022 | Financial Freedom, Money

Writing this list is going to make me look stupid.

Ahhh well. Better to have lived and farted in public than to have not lived at all, as the saying goes.

This is my war chest of financial mistakes. Avoid them to reach financial independence faster.

Asking for too much money

Earlier in my career I had a chance to work for some great startups. Instead, I made a mistake most people make — “pay me b*tch!”

I asked for stupid amounts of money rather than focus on the learning and networking opportunities.

I still see the same mistake. People pitch me daily to work with me. They ask for crazy perks and a lot of money. If they only knew the power of being in my inner circle they wouldn’t want money.

But we can’t see what we’re blind to.

Lesson: Without skills and contacts, no cash.

Becoming an out-of-control drunk

Multiple times in my life I’ve been an out-of-control drunk.

The first was during my early 20s as a DJ. I had severe anxiety and was unsure of myself. To hide the nerves and the embarrassment I drank like a fish. The stupid things I did while drunk cost me many high-paying DJ gigs.

The second time was during my single days. I got out of a bad relationship and hit the clubs looking for a female mate. Picking up chicks has never been an easy thing for me. I don’t have the biceps, flashy car, or sexual prowess in the bedroom to wow them.

To make things worse, I had been sober for several years.

In Australia, if you don’t drink you become an outcast and people think there’s something wrong with you.

Red wine is a prerequisite on almost any date. I quickly learned the hard way. Multiple women had issues with my lack of drinking.

So, I took up the booze again to impress them.

That’s where things got wild. I got so drunk on some dates I blacked out. On another date I vomited right near her feet. I think some splashed onto her heels. Gross.

The new drinking habit became expensive too. A night out with a date and booze would destroy most of my petty savings in a jumping jack flash.

Not only did I not find love, but when I drank at work events it got me in trouble and ruined whatever reputation I had at the office.

Lesson: you think drinking makes you more likable, and therefore more money. It doesn’t.

Nearly getting wiped out in 2008

A recession can rip your face off.

In 2008 I was deep into startup land. Business was okay. We were hiring like crazy despite the bad news.

“Ahhh mate this damn thing will pass. Chill out dude.”

Days later Lehman Brothers on Wall Street collapsed. Our business had nothing to do with financial services so we thought we were immune from the financial contagion. Nope.

Why? Our customers became infected with fear. So….

They canceled orders faster than the former president Donald Duck cried like a baby in random tweets before he got banned for life.

Suddenly revenue went right down. No orders, no money. We didn’t even know how we would pay the rent on our own homes.

We had to fire some of the new hires who were incredible. Our bank didn’t like what they saw. They could have brought the whole damn operation to its knees. Through some miracle — probably luck — we survived 2008, barely.

It left me with recession scars.

That’s why in this current recession I’m being so careful with money. I’m not running around like a smartass and thinking I know everything about markets.

Markets go down in a recession. Then they appear to go back up. But those “ups” are often nothing more than fake-outs. Fancy Wall Street bankers call them bear market rallies.

It’s easy to get carried away with the discounts on your favorite stocks. Or think customer orders will pick up again faster than they do.

Lesson: in a recession you need more cash than you think to ride out the storm and rejoin everyone back in the good times. And recessions make you mentally tougher the next time, too.

101 Eight Ridiculously Stupid Things That Cost Me a Lot of Money

Photo by Vidar Nordli-Mathisen on Unsplash

Being a tightarse on professional services

You don’t hire a cheap surgeon to help you recover after a heart attack. Why the freaking hell would you get low-cost lawyers and accountants?

Don’t worry, I made this mistake.

I got a $150 a year accountant and did my legal dirty work myself. This dumb decision left me with a 6-figure tax bill and nearly bankrupted me. My legal issues became dire in one particular case too. Now I have a $10k+ a year accountant but the financial benefits are at least ten times that.

Lesson: Lawyers & accountants save you way more money than they charge.

An ego bigger than Papa Elon

A bit of money can make you think you’re a superstar.

That’s what happened to me. Your ego can quickly inflate to Elon Musk’s whopper head size. Before you know it, you’ll be trolling others on social media and flexing your legal team as if it’s enhanced genitalia gifted at birth.

When I walked away from my startup in my 20s, I could have gone on to work with some of the people I met during the experience.

But behind closed doors I discovered that none of them liked me anymore.

They thought I was an arrogant prick who should go jump in the lake. So, I had to return to the job market and get a minimum wage job in a call center. Had my ego been in check, though, things would be different.

See, even if you fail at a startup, you become in high demand.

Investors, leaders, and CEOs love people who’ve started their own businesses and failed. It shows execution rather than fake experience represented by a common resume that gets you nowhere.

That’s why I tell everyone to start an online side hustle and make a little wifi money. It may not work but it sure as hell separates you from the other sheep you’ll encounter in your career.

Lesson: ego is enemy. Less ego, more money.

Using a savings account

I invested in a dumb savings account and gave up my soul to the inflation devil for too many years.

Banks call savings accounts investments. LOL.

All a savings account currently does is pay you a lower interest rate than inflation. A savings account is the bank’s investment to use your money to invest in markets and make a sh*t-ton of profit. Don’t get fooled.

Lesson: investing needs to make higher returns than inflation. Otherwise, you’re going backward amigo.

Thinking stocks were risky

I avoided buying stocks for years because I didn’t understand them. They were too risky for my taste.

But you need risk. No risk, no reward. The trick isn’t to avoid risk, it’s to make smart risks. How? Do your own research and get a financial education.

Once you know how investing works, you can minimize risk by diversifying across multiple investments.

Lesson: get a financial education to understand risk.

Own this one thing (and not this other one)

The employee mindset often programs us to become good little consumers.

The problem I found is I spent most of my income on material junk. One day a smart man said to me “Own businesses you dummy.”

Businesses make money. If you invest money in a business that makes money then you make more money. Get it?

One way is to be a pussy like I was and invest in stocks first. The second path is to create your own business.

Take one 9-5 skill you already have and use the internet to sell it two, three, or four times more. The internet then applies leverage to that skill over time. The initial effort compounds without requiring you to give up more time to make more money. Genius.

Lesson: invest in businesses. Learn how they work. Then start your own online business on the side.

Final Thought

Ridiculously stupid things that cost you a lot of money provide the best lessons. I wouldn’t take back any of my mistakes. Okay, maybe I would’ve not gone back to alcohol.

If you haven’t done dumb stuff with money, then you won’t unlock the magic of self-learning that leads to eventual wealth.

Execute daily to get in the money game.


This article is for informational purposes only, it should not be considered financial, tax or legal advice. Consult a financial professional before making any major financial decisions.

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