Why Write Now?


This is the website I wish someone wrote when I was in my 20’s and 30’s. Back when I was “working jobs I hate, to buy shit I didn’t need“.

So I guess I’m writing this selfishly for me. Maybe I’m giving back, to my past self, in hopes that someone else finds this as exciting to read about as I would have back when I was young and hungry for information about how to succeed with an online business.

The best place to start is with “Who Am I?” and “What Is This Website Going To Be About?

My first job was as an Associate Engineer in an Artificial Intelligence lab at a large company, but back then, I was just dabbling around in software development, doing just enough not to get fired.

Following that humble start, I ventured out to try my hand in Silicon Valley with my first start-up developer role.

For that first decade of my career, I designed, architected, developed, and deployed software solutions for large and small companies alike.

As I reached my second decade, I transitioned into a cybersecurity consulting role for companies across the globe. Less technical hands-on work, more reports, and a lot of talking with other players in the industry.

After 20 years of working in IT companies (or the IT role in a regular company), I decided it was time to figure out how I was going to survive in IT now that I was approaching 40 years old and becoming a bit old, at least, according to Silicon Valley norms.

No Man’s Land

The IT industry is trench warfare in WWI. When you’re the new conscript in the trench, getting your soldier shit done, it’s not too bad.

But, at some point, you’re going to be the senior soldier, and you’re the next one called out to go over the top into no man’s land.

And nobody comes back from no man’s land.

Colleagues were not able to move to new companies as they once had, not because they didn’t have the experience, but because they had experience and Silicon Valley is bombastically proud of its history of discrimination against older workers.

Most of us had “achieved” ourselves out of our own jobs because companies can just hire any recent college grad that will take anything just to have that first job.

Like the next soldier over the wall, death was all that was in front of us.

The Two Rules of this Website

How to get around this problem so I could survive once I hit 40 years old? It was a tough question, but one I knew I had to eventually figure out.

I don’t remember the first thing I realized regarding my future career, but I do remember the last thing I realized.

I finally realized that if I was trying to own a successful business, where I was in charge, then I was doing everything wrong. 

Rule 1) If I wanted to be successful, I needed to stop ever again trying to start my own business.

Overwhelming evidence proves that we will all fail if we keep doing it over and over (just like I failed too).

Rule 2) If I wanted to be successful, I needed to be buying my own businesses, not starting them. 

It doesn’t matter how large or small the purchase is at first, but learning the buying, operating, and selling lifecycle of business provides a much greater chance of success than trying to start a business on your own.

Once I figured those two facts out, I had a game plan for my future success.

I’m in my mid-40’s and manage a portfolio of online assets, mainly software businesses, that I purchased over the last few years.

I keep my businesses simple, lean, and narrowly focused. I am the only boss (just kidding, honey) and only hire for specific tasks that I am either not very good at or don’t desire to learn.

I’m protected from employer discrimination, firings, furloughs, downsizing, rightsizing, layoffs, government shutdowns, and even pandemics.

I control my own destiny, for better or worse.

This website will try and capture how I have reached that point today and what I’ve learned along the way.

Hopefully, it can help anyone else out that might be interested in doing the same thing in the future as they transition from early career to mid-career in the IT industry, or any industry, for that matter.