Ep1. Making Money While I Sleep Podcast

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Hi there, my name is Dan. You’ve never heard of me. I’m a creative services manager at a medium-sized accounting-adjacent not-for-profit-but-kind-of-for-profit company. That’s not really important. It’s complicated, but kind of irrelevant.

I’m at a point in my life, Where I’m lost. I feel unextraordinary, unimportant, underutilized, and I feel it deep in my bones.

You see, I work at this company that is a mess. My much more eloquent copywriter colleague refers to our office, and company in general as a “complete garbage fire”. Today, I left another of those awful teleconference calls with our clueless CEO–who is having these pointless teleconference calls, because she is struggling to understand the basics of what most of the department heads under her even do–and the only words I can find are: “What a Cluster Fuck”. 

It really is that bad.

I guess it’s par for the course. There has been a sense of building resentment and distrust in corporate management, and our conservative, culturally irrelevant company was no exception. We have no passion, the few people who I do work with that aren’t inept are completely devoid of spark and vision. They are comfortable working out the rest of their careers in the same position, making a roughly 3% raise every couple of years, and taking a small bonus when the department–for which we have absolutely no impact on the performance of–does an arbitrarily “good job”.

I think that the biggest product that our company makes is dead careers. If we had a service to sell, it would most likely be a long, arduous slog to your paltry retirement.

I like the people I work with directly. I have a good boss, who is a genuinely good man. And he’s extremely smart. I just can’t figure out what the hell he is still doing here. He seems to be single-handedly doing the jobs of his boss, the Vice-President, and to some extent their boss, the Senior Vice-President.

This isn’t just hyperbole. I have seen him walk his boss through a simple concept–mind you, this is a concept that his boss is wholly responsible for, and a concept he should understand in great detail, yet my boss has to explain it to him as if he were 5 years old learning his ABCs again.

This hand-holding is embarrassing, and I mostly sit and take notes, partly because I can see that if my boss jumps off the roof after delivering one or two more of these remedial lessons for overpaid executives, it will become my responsibility next to change the VP’s diapers for them.

On top of this, our corporate head office is located in another city, and our favorite resident Vice-President/toddler is being moved to the head office location. This should be a time for joy, an end to the in-person diaper changes.. but with no other senior executive staff in the office in our city, the building has been put up for sale.

No, I’m not kidding. They put our office building–which the company has owned for decades–up for sale while we are still working in it. 

Of course, the company is telling us they are making a leaseback agreement a mandatory condition of sale, meaning we would all stay in the building, and the company would just lease the space from the new owners, effectively changing nothing about our situation, but I just don’t buy it. The building is worth tens of millions of dollars, what are the odds that if the right offer came along they wouldn’t throw us all under the bus? Zero.

They might just let us work from home full-time, but I seriously doubt it, the culture is far too conservative, and our current one day every 2 weeks WFH is frowned upon already. You see, some people complain that their job isn’t possible to do from their homes. God forbid there be even the slightest bit of inequality between departments. 

We should all suffer as much as the least lucky individual in the company, right? Equality in everything, at the cost of anything, right?

Okay, why am I telling you this? It’s not to just rant, although I have to be honest, it feels good to finally be honest about this place. God knows most of the people working there are not.

No, the reason I am telling you all this, is because I think I have a solution. You see, the problem with my career is nobody wants to hire me for the kinds of jobs I want. I want a creative job where I can be the master of my universe and create wonderful things. This is very hard to find on a good day, and not being young makes it even harder. I know, because I have been job hunting since pretty much the moment I started this job I am currently rotting in right now.

Oh, right my idea! 

I want to start a business, and run it while I work at my job. Not necessarily at the same time–although I’m sure there will be some of that–I want to take advantage of my free evenings and weekends to pursue a better life for me and my family.

Oh yeah, did I mention I have a beautiful wife and even a wonderful newborn son? Yeah, responsibility falls like an anvil on your head sometimes. 

So the pressure to make sure something is there to catch me if something does happen to my position here at the company, or they sell the building and decide to act on what they have only shown us–thinly-veiled as it is–that we are a totally replaceable and disposable workforce.

I haven’t decided what kind of business to start, I think that may take some considerable thought and research, but for now, I think it’s the answer to my problems. If it becomes successful, I can leave my job, and pursue being an entrepreneur full-time. Maybe even start another business. Maybe sell one for a profit down the line, who knows.

The point is, if something happens to this job before I am prepared, it could mean a big problem for my family. 

I refuse to let the people I trust least in my life–that would be the executives at my company–with the decisions that will impact my life the most.

I want to get ahead of any potential risks with my career and my current employment, and if that day ever comes when I am escorted out, or walking out on my own accord, I want to have a smile on my face, knowing I have a backup plan, and it’s better than the current plan!

There’s this concept in the world of making money, and it’s all about making money in your sleep. You see, the wealthiest people in the world usually make money 24 hours a day. Their companies or stores sell products and services all day and night. Their money makes them money, even in their sleep.

It’s the same thing with wealthy stock market investors. They invest large sums of money into the market, and providing they have made somewhat intelligent trades, and traded in sufficient volumes and over long periods of time can–like magic–make money with only spending money.

This is the goal–not to be an institutional investor–but I want to join the elite group of investors and entrepreneurs that can say they make money at all times of the day.

On vacation in Italy? Making money.

Christmas Day? Still making money.

3 a.m. on a Thursday? You guessed it, Benjamins, baby.

Yes, the biggest difference between the wealthy and the rich is that rich people like doctors, lawyers, executives, engineers, and bankers work every day, and make a large hourly wage. 

However, their ability to scale that income into true wealth is limited by their ability to work more hours in the day. If they want to double their income, they essentially need to double their time investment. In reality, it’s not black and white like this, as hourly wages and bonuses increase with time, can increase based on other factors, etc. but let’s keep it simple for our purposes.

And yes, many doctors, bankers, and lawyers know how to turn that significant salary into smart investments and retire with enormous wealth, that’s true. But for now let’s just focus on the difference between an hourly wage, and an investment.

An hourly wage is a set payment for a set unit of your time working. Everyone is familiar with this, as we most likely have all worked an hourly wage job. Even if you are on a salary, where you aren’t paid hourly, you are paid monthly, or bi-weekly. A certain amount of money, for a certain amount of time. It hasn’t escaped anyone that salary is just a fancy term for monthly wage, instead of an hourly wage, right?

My issue, as I suspect I share with a great many others, is that if I work harder, and become more productive, I don’t get paid commensurately with that effort, and while there may be a small raise at the end of the year, and maybe a small bonus, it’s just not conceivable that these increases in money are equal to the increase in effort over the period of a year. Now, some performance-based salaries and bonuses are probably better at rewarding this kind of effort, but in most cases, it’s not. A raise you get at the end of the year is likely barely covering the inflation and increase in costs of living. In my area, a high cost of living city, I doubt it even covers that.

Now, I’m not pretending that by starting a business I am going to become suddenly very wealthy and be cruising on yachts in the Mediterranean anytime soon, but I firmly believe that the concept of building wealth by investing in something like a business, if that business plan is executed wisely, can make good money 24 hours a day, or at least, without the constant effort of me, the owner.

In other words, the investment of my own time doesn’t necessarily have to equate to an increase or decrease in my income. I believe in this concept firmly. And when an increased effort is made by me, it should directly translate to increased sales/profit/revenue, etc If it doesn’t, then as a business owner you have placed your efforts in the wrong place, or your business model does not function properly. Either way, you are responsible for your own destiny. I can get behind that kind of risk/reward system.

Do you remember that anecdote that the teenagers used to tell each other about Bill Gates?

They used to say that it wouldn’t be worth Bill Gates’ time to pick up a thousand dollar bill off the ground. The anecdote is based on the fact that because of his enormous wealth, he made more than a thousand dollars in the few seconds that it would take to pick up the bill.

Now, I don’t want to get the mathematicians into the mix and calculate what Bill Gates might have actually made in an hour, and break that down by the second to find out if it was worth his time to grab a thousand dollars from the ground as he walked past. But one thing always bugged me about this story:

He doesn’t stop making his hourly wage because he stopped to pick up a thousand dollars off the street. 

Microsoft doesn’t halt business and stop selling software and games when Bill Gates gets distracted by something. He doesn’t turn off the Windows “Buy Now” button on the Microsoft website when he’s not in the CEO’s chair at Microsoft HQ.

It’s always worth your time to pick up a thousand-dollar bill from the ground, even Bill Gates, the richest man in the world.

That feeling I had then that this anecdote was dumb and ill-conceived is the same feeling I have now when I think about my job. Working like this is dumb, and ill-conceived.

I shouldn’t be working 9-5 for someone else to make money in their sleep. I should be making my own money. At least, I would like to. But how?

How does one start a successful business? So many questions and not enough answers right now. 

I am usually the jump-first-and-ask-questions-later type. I like to force myself into uncomfortable situations, and while my instinct is to do something rash, like go ahead and start a business and quit my job immediately, and figure it out along the way. 

However, I feel like the stakes in this particular decision are far too high. I am not single anymore. I mean when I was young, I once moved to Australia on a whim. While it was a great adventure, it was pretty dumb. I landed in Sydney without even a hotel to stay at.

This decision needs to be thought out, planned, and carefully considered.

The one thing I can say for certain is that I am lucky I don’t like my job very much. If I loved it, I would probably be blind to the danger that lurks in this organization. I see people walking around my office like nothing is looming over their heads, and I just know the rug could be pulled from under them instantly. What would they do if they lost their jobs next month? What would you do?

Me? I’m going to work on that now. I will hopefully have some answers, or at least some better questions by the next time you hear from me!