Entrepreneurship: The Last Refuge Of The Trouble Maker

Matthew J Carter
4 min readMar 18, 2019

The good news about entrepreneurship is that your fate is in your hands. The bad news is that your fate is in your hands!

In fact, after selling my first company I bought 3 Mustang’s a Red, White, and Blue just to take a photo on the 4th of July with them in a line.

As an Entrepreneur who has built and sold two tech startups, I can tell you first hand that we don’t have to Make America Great Again.

It never stopped being great.

President Trump, the alt-right, and everything in between who are currently perpetuating the fallacy that they are “America” and only they can “Make America Great Again” to me seems their actions are doing the exact opposite of making America great. I would even go as far as to say they are what’s wrong with America.

Let me tell you a story about why America is already great.

It involves “Mustangs and Tommy Hilfiger” the first was represented in the photo above and the second I will attempt to explain below.

Although those two things are not necessarily considered luxury items, what they do represent to me is much more than just the car or the clothes to me they are America. Why? because, at some point in my life, someone told me I could not have nor did I deserve them.

Here is one of my favorite examples:

In 8th grade, I had just gotten a Tommy Hilfiger shirt as a gift for my birthday. So I was so excited when my cousins who we aptly named “the rich cousins” got it for me.

The night before school, I ironed it, laid it out, making sure to get just the right pants to pull my outfit together. I woke up early so I could iron out any wrinkles that it may have got overnight.

I still remember getting ready for school looking in the mirror and thinking to myself, “Today is going to be a great day”

Then while walking into class, one of my classmates, who I will save from the shame told me: “Why are you wearing that, you’re not white?”

I still remember how terrible I felt that day, what was suppose to be a good day just turned into one my worst days.

However, it was at that very moment that I told myself I would make it my life’s purpose to wear as much Tommy Hilfiger as I could.

So I lied about my age, backed up my birthday by two years and got a job at a little 24-hour cafe as a cook.

It was within walking distance from my home, so I went to school during the day, napped, and then I worked the graveyard shift went home, showered and then caught the bus.

I did that every day for two weeks. Then it was payday, I got the first check and I bought as much as I could and with every subsequent check after that.

I bought the shirts, the pants, the shoes, the backpack, basically, if it had the familiar Red, White, and Blue logo on it, I got it. Some would call that foolish or a misallocation of money.

I call it “fuck you” because even though I never said it to my classmate, I made sure that I sat next to him every day and my clothes would say it for me.

Occasionally, I’d purposely place my Tommy Hilfiger backpack on his desk and wait to see his reaction. Those were good times, but even into adulthood, I have maintained a great fondness for the brand.

I have similar stories for the Mustang and succeed, but I don’t want to shy too far away from the point.

I grew up in subsidized section-8 housing, got my teeth to straighten and my broken arm fixed with Medicaid, I ate food that was purchased with Food Stamps (SNAP) and was raised by an amazing single mother.

So as far as my political beliefs, I have no problem stating that I lean largely liberal because, without those “liberal” policies and laws that ultimately funded the above-mentioned programs, I would have never been able to go to college, build a successful business, or become a contributing member of society.

So if I am ever attacked, disliked, or boycotted, because of those beliefs I invite you to go back and re-read, especially the part where I said: “Subsidized Section-8 Housing”.

For those of you who don’t know, those are fancy words for “The Projects” aka “The Hood”, aka “I had to fight most days just get from the bus to my home” so trust me its not even a competition, I already won.

That’s my America because in no other country could a minority raised by a single mother in less than favorable circumstances be able to accomplish everything that I have.

At 33, I have already done more than most people will do in their entire life.

So I say all that to say before you call someone a “snowflake” or any myriad of derogatory names.

You should consider, some of us “snowflakes” grew up, sat, and ate with people a lot more threatening than you and thanks to our largely liberal policies and beliefs, we were, also educated, successful, and if in a boxing ring would probably kick your ass.



Matthew J Carter

Entrepreneur and founder with a track record spanning 12 years in various start-ups, and one acquisition.