Bootstrapping a Company that Can’t Fail

Mr Money Grubber
7 min readJan 15, 2021

One of my earliest memories is of me being at my childhood home, in my garage, pretending to be a shop owner. I’d gather a bunch of rocks or some old plastic toys and set up them and pretend to sell them to others. As strange as that sounds I really enjoyed it.

There was something about the idea of buying an item for a certain price and then selling it a bit higher that intrigued me. Even today I still get excited when I think about it. After having retired at 38 years old due to my frugalistic ways I knew that I wanted to start a business, which one I wasn’t sure of at first. I am a software developer by trade so I figured that might make sense. The problem with that its that it’s a pretty involved business.

So I decided to cast that aside and instead focus on what I really love, saving money! This isn’t the first business I’ve started but for the most part I’ve just been a worker bee. I had good reason to actually. I was earning more than many small businesses make as a software contractor heading out to whatever company would pay the highest dollar.

After discovering the FIRE movement though I realized that I could actually fulfill my bigger dream and not have to work anymore. I had to reduce my expenses greatly but I was at that point where it just wasn’t necessary. I could easily earn more than enough passive income to pay my bills, and not have to work (I did reduce my expenses by 80% to actually make that happen however).

Having done that for a better part of a year it was time to do what I’ve always wanted to do, start my own business. This time though things were different. This time I can’t fail. I’m not trying to say that there’s pressure on me and I have to succeed, I mean, that there is literally no way I can go out of business unless I quit.

Two Options All Companies Have

To dive in deeper on this let's think about why companies actually fail. For the most part, there is only one reason. They have lower income than expenses. And once that process gets going, watch out. If you think of all the recent failures in business from old players like Sears to the hilariously poorly managed streaming service Quibi, the reason is always the same. Their expenses were greater than their income.

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Mr Money Grubber
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I retired at 39 by living ultra frugally, I own my house outright and love saving money. This blog is about that.