My Entrepreneurial Journey (A Brief Introduction to Scott)

by Oct 17, 2019Entrepreneur2 comments


It’s time to live life on my terms.

My entrepreneurial journey is underway, but it didn’t just happen. Instead, it took many years to get here.

Even as far back as high school, I liked the idea of owning my own business. Back then, I didn’t know much about politics, about Democrats and Republicans, or about libertarianism (which I doubt I had even heard of). The idea of liberty, of controlling my own life, of being the person with the final say over how I lived, appealed to me, though, and I saw working for myself as the way to get there. But being an entrepreneur wasn’t a serious consideration. The desire just wasn’t a raging inferno, yet, but more of a smoldering ember.

What Do I Want to be When I Grow Up?

In junior high school, I didn’t know what I wanted to do when I grew up. In high school, I got the great idea to be a stock broker. Later, that great idea turned into investment banking. I don’t know how these ideas got into my head; they just did. Honestly, I didn’t even know what an investment banker did. I guess it just sounded like fun – I’m a banker who invests in things.

When I enrolled at Florida State University, I had my sights set on becoming a CPA. I took an accounting class in high school and found that columns of numbers made sense to my logical brain. A few college accounting classes made me realize, however, that those columns of numbers wouldn’t maximize my lifetime fun, so I pivoted. In the end, I graduated with a finance degree and no idea what I wanted to do with my life.

Making Critical Errors

If the American education system is supposed to prepare our youth for the rigors of adult life, I crashed and burned spectacularly. Despite a lifetime of good grades and graduating with honors I managed to walk out of undergraduate with no practical skills and no clue what I wanted to do with myself.

At this point, I had two justifiable options: (1) start a business or (2) go find a job, any job, so I could start building a marketable skill set. My choice? I enrolled in an MBA program at the University of South Florida. You’re reading that correctly. I went right back into a system where I had already failed. Definition of insanity? You bet.

That event marked my first great critical thinking failure.

USF didn’t change my life much. When I graduated, instead of a finance degree and no clue, I had a finance degree, an MBA, and no clue. One positive, though, business school fanned that small entrepreneurial ember into an actual flame.

Not Cut Out For Corporate Life

I took a job as an IT consultant. Not surprising to anyone who knows me, about 5 nano-seconds into that job, I realized that I don’t like someone telling me what to do and how to do it. Being part of a collective where I’m expected to work hard for someone else’s benefit just isn’t what sets my shorts on fire

So, when IT ran its course, what did I do? Well, I went right back into the waiting arms of the American education system. Yes, that place where I had already failed . . . twice. I went law school.

My second great critical thinking failure.

Utterly Unemployable

I knew I didn’t want to practice law. But, directionless, I stuck it out in law school. While there, I participated in the entrepreneurial law clinic and took a lot of business law classes. I enjoyed helping entrepreneurs build their businesses but I really wanted to be on the other side of the fence: not the attorney but the founder. That entrepreneurial flame got a little stronger.

For those keeping score, I now had a finance degree, an MBA, a J.D., ten years of IT experience, and, you guessed it, no clue.

Here I was. A ton of education with some practical experience mixed in. A great opportunity to finally scratch that entrepreneurial itch, right? To put my education and experience to work by starting a business. So, what did I do next? I took a job with the Federal Government.

Being a Fed made me miserable. Entrepreneur minded people don’t thrive there (although, interestingly enough, that’s exactly the type of person the Government claims it wants). The Federal Government is a collective that puts all other collectives to shame. The uber-collective. It’s a place where independence, common sense, and reason go to die horrible deaths.

Needless to say, I didn’t have a good run there.

My time with the Feds did have two notable outcomes: 1) seeing from the inside the insanity of the government brought my libertarian leanings into full form and pushed me all the way into the anarcho-capitalist camp and 2) that entrepreneurial spark exploded into a raging inferno.

Taking the Plunge

During my government cubicle zombie years, I came to distrust the management team I worked for. The Feds would have you believe that they work for you, the People, but the sad truth is that, for the most part, the Feds work for their own interests. With my growing libertarian leanings, I knew I would wear out my welcome at some point. For some reason, Feds who operate under the illusion that society would collapse into a 24/7/365 version of The Purge don’t like it when you tell them that what they do is a waste of time and money. So, in 2018, I created a small side-hustle.

In June 2019, the inevitable happened. I found myself on the wrong side of an office dispute with a snowflake coworker. Before it fully hit me at how quickly a bad work environment can turn outright hostile, I quit. This time, with the beginning of my own business hanging out in the ether, I took the plunge and started devoting myself full-time to my business.

Finally, I made the correct choice. No more looking to an education system that doesn’t suit me. No more working hard to get someone else promoted.

I don’t have any excuses now. More importantly, my GF is very supportive. I might as well go for it.

(Re)developing a Success Mindset

Years of being a cubicle zombie took a toll on my mindset. Rather than focusing on being productive, I focused on not screwing up. Government management philosophy holds that under-performing is better than making mistakes, so, over time my mindset shifted accordingly.

It doesn’t take a genius to realize that by focusing on not making mistakes, we severely limit our chance at success. Mistakes are going to happen. That’s how we learn and get better. That’s how we achieve.

I need to refocus my mindset from avoiding failure to finding success.

My first step to developing a success mindset is getting back to proactive thinking. I create my world. The world isn’t something that happens to me. I have the power to change it.

My Why

“He who has a why to live for can bear almost any how.”

– Friedrich Nietzsche

As I type this post, it occurs to me that the most important part of my journey is to know my why. Why am I doing this? What do I hope to accomplish? Money is an easy answer, and, while money does not buy happiness, it sure as hell makes finding happiness easier. But money is not the reason. Money is merely a means to an end.

It’s freedom. Working for yourself in order to chase freedom is almost cliché these days, but it really is a powerful motivator for someone like me.

Freedom, for me, is the new definition of happiness. I never jumped out of bed in the morning eager to go to work. When I wake up in the morning, I journal about what I’m excited about for the day. Before, my journal never included anything that had to do with work. Now, my morning journal almost always includes something about my new work.

Strength and Reason

I don’t have any delusions that maintaining a blog is easy. I welcome the challenge. In fact, one reason I’m blogging is to push myself out of my comfort zone. My difficulties as a cubicle zombie never came from an aversion to hard work or taking on challenges, but rather came from inane policies that made my work harder than it should’ve been.

Strength and Reason is my freedom. I can make of this blog what I want. My schedule is mine and I can publish what I want. And, of course, freedom also means that I have to be accountable for every decision I make, the way it should be. So, all inane work policies are on me.

Time to Crush It!

I have an incredible opportunity to reinvent myself. I can finally follow my path instead of one that only leads to a cheap gold watch and a kick in the ass when I’m deemed too old to contribute.

Going it on my own is daunting and lonely. But there is no price that I can put on the freedom that it offers.

I’m in control. My success depends wholly on me and no one else. It’s a new world thanks to the Internet. Opportunity abounds. Time to go big and own the world.


  1. Michele Forster

    Thanks for this Scott. It takes courage to jump out of your comfort zone, and bare yourself in this way. Excited to follow on your new journey. Keep that spark burning!

    • Scott

      Thanks! I’m glad you’re on board. It means a lot to me.


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