As a teenager you started fixing up broken Xbox 360’s and reselling them for a profit. Where did you learn how to fix electrical game consoles like that and what got you started in the first place?

Yes, that is correct. When I was a teenager, everyone in middle school and high school seemed to have an Xbox 360. These were very faulty gaming consoles that often ended up with “the red ring of death” – in other words, they would no longer work. I noticed that many of my friends and schoolmates were having this issue. I turned to Youtube to learn how to fix this problem, as it happened to my console as well. I watched many tutorials and eventually was able to fix my own Xbox. From there, I started purchasing broken Xbox 360’s for nearly nothing from my peers and from people selling them on Craigslist. I would simply go pick them up, fix them with my tools, and resell them on Craigslist. I sold them with a 2 month money back guarantee at the beginning, as I wanted to make sure the devices were truly fixed. I experienced no problems whatsoever, and did this for many months.

I am guessing that once an entrepreneur, always an entrepreneur and you mentioned that you moved from repairing Xbox 360’s for resale, to buying and selling cars. Was this a natural shift for you, or purely one built on an opportunity presenting itself?

That’s right, I moved away from my long-time Xbox strategy and began to sell, buy, and selling cars in college. I attended multiple Universities, and was playing Division-1 football along the way. I found that people were no longer interested in purchasing Xbox 360’s like they once were; however, this did not stop my entrepreneurial spirit. Whenever I could find spare time, I was always thinking of creative ways to make money since there was not enough free time in my schedule to get a normal job. At this point I was very familiar with Craigslist and Ebay. I had read about the man who started with a paperclip and turned it into a house, so I wanted to see what I could do with my $900 car. I traded my car on Craigslist for a slightly better vehicle, then continued to trade car after car.

Essentially, deals do not cost much money at all. When I didn’t see many similar cars listed, I would quickly sell mine. Where I was living at the time, there was not a wide variety of cars to choose from.

At this point, I knew what sold well in the market where I resided, and I knew which types of cars could return the most profit. In summary, my approach would start by finding a car I wanted to purchase, flying down to Southern California when I had spare time, negotiating the price with the private owner of the vehicle (no dealers), driving it back up to my market, and selling it for around triple that of what I purchased it for. All in all, I would definitely say this was a natural shift in my entrepreneurial adventure.

What negotiation skills did you learn during this time; were you born with the gift of negotiating, or is this a skill you picked up along the way?

If you asked my family, they would tell you that I was born with the ability to negotiate – I would also agree with that. What I developed through my time doing this was the ability to detect when something just wasn’t right, almost like a sixth sense. Oftentimes on the internet, especially Craigslist, you will run into dishonest people. I had many encounters that involved people trying to sell me cars that were about to fall apart, that were not actually theirs, or that were not the cars in the photos or videos they posted and sent to me. This taught me to do quite a bit of digging not only on the vehicles, but more importantly on the owners before making my trips. In person, I was almost able to tell immediately if I wanted to proceed with the individual or not just based on conversation as well as my gut instinct.

In business, the art of negotiating seems to be one of the most important skills anyone can possess. Do you agree with that, and do you feel that what you have learned is transferable? Do you think that you would be successful in any market?

I do agree with that for the most part. I believe it is crucial to do your research and to come to the conversation prepared. There are many tactics to successfully win a negotiation, and if anyone reaches out to me personally, I would love to share what has worked well for me. If you do not do your homework before negotiating, especially if you are dealing with someone who is an expert in their respective field, you will get eaten alive. I would also say it’s essential to understand the thought processes of the buyers and sellers that you are dealing with- put yourself in their shoes and play out multiple scenarios until you feel you are ready for anything they may throw at you. I feel that many of these skills are definitely transferable, but I do not know if I would be successful in any market. I have the confidence to say I would be, but you never know until you try. I believe everyone has their own unique strengths, and it’s up to them to find where those strengths suit them best.

I understand that you have plans of entering the fitness industry next. You mentioned releasing a series of E-books soon. What exactly do you have in mind and what has motivated you to move into the area of fitness?

Fitness is one of the most important parts of my life. I played sports my entire life, and I have been working out since I was 13 years old. Fitness is a lifetime journey, and it’s something anyone can take part in, no matter what they are limited to, what their starting point is, or what age they are. Over the years, countless people have asked me for fitness advice. I decided to create a series of E-books to help beginners learn how to properly train and build muscle. I have a lot more planned than just E-books, but it’s my first step into this space.

What piece of advice would you have for young aspiring entrepreneurs looking to start a business or side-hustle?

I would advise younger individuals looking to start a business or side-hustle to find something that you are either naturally skilled at, or that really excites you. I would definitely start with a side-hustle first, as you can always turn it into a full business down the road. For me, Xbox’s did not interest me, but I was good at fixing them; however, trading, buying, and selling cars all from the comfort of my couch greatly excited me, and I loved the experience of trying out some really cool cars along the way. If you’re looking to do something long term, I would emphasize finding something that you can wake up and be excited to do.

What are your social media links so we can keep up to date with you?

My Instagram account is @italian.


  • Gail Green



    Interior designer/decorator and founder of Gail Green Interiors.