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Do you have a history of entrepreneurial tendencies?

"Ferris Bueller's Day Off" movie distributed by Paramount Pictures

With all the momentum around freelancing, small business, and startups many people are probably asking themselves the question - “Am I an entrepreneur”?

Given that many are asking themselves this question I thought to share my story to help you think about your personal entrepreneurial origin story. The question for me came up when I was going through a long interview process. One of the interviewers asked me — “what experience lead you to believe that you are entrepreneurial”?

Before I go into my answer allow me to set the scene. I really wanted this job. This was a post grad school (and loan) interview, so I was very serious about landing the position. I had interviewed at a few other great companies however, I was really zeroed in on this particular role.

Many senior level executives spoke to me during this interview process. I was nearing the end of what I felt was a good representation of who I am, my experiences, and why I was the perfect fit for the respective organization.

I’m near the final stretch of the interview process (last of 4 interviews, each with 3 interviewers) and I’m hit with the question. “What experience lead you to believe that you are entrepreneurial”?

My response to the question…

Many small instances when I was growing up pointed at me being a hard working kid that could always figure out how to make a buck to fund my interests (e.g. skateboards, sneakers, candy, etc.). In other words, kid contraband. All the stuff I wanted that my parents didn’t endorse, and most of my interests (at the time) fell into this domain of goods.

However, the most concrete and memorable moment was when I was in my high school bedroom dumping pockets full of paper cash from my pants, shirt, and hat into my dresser drawer.

You see I had to quickly empty my pockets, along with anything else I could hold paper money in, because they were absolutely full and I still had a line of customers around the corner of my parent’s suburban house.

This was the 3rd time that night I was in my room clearing my pockets. At this point I had more cash in that drawer than all of the summer jobs I had worked combined that summer. All earned in a single night.

What I was doing was having a party at my parent’s house while they were on vacation (sorry mom and dad 😬).

What I did was sell plastic cups at the door of my house where I had a couple barrels of beer in my basement, purchased by me through one of my friend’s big brothers.

The idea and execution of the plan was simple; I would sell as many cups as possible at the door until my house and backyard filled up. To get “customers”, I “networked” with friends and convinced them to invite their friends to my parties.


Signs of Entrepreneur Thinking

I knew by watching other parties I attended that the problems came when the alcohol ran dry, the party manager would be forced to keep supplying alcohol to the crowd throughout the night… this would have three key negative impacts:

(1) buying more alcohol increased the costs associated with the event;

(2) as the crowd got more tipsy they tended to have negative effects on the house (e.g. breaking stuff, spilling, getting sick, etc.);

(3) it was inevitable that at least one tipsy character would start trouble.

So I did what I thought was smart (at the time)

I called the police on my own parties after the alcohol ran out. I knew the police officers in my town so this was not a source of more problems for me. It was a source of help, free bouncers if you will. I had the mayor’s son as a guest along with many relatives of the local police force. This helped my argument when negotiating with the police. In the end I just kindly convinced the officers to clear out my house, please.

The officers were super nice and thought it was fun to walk through my house with a mag light looking for hiding under aged party goers. The cops scared them into going home as quickly as possible.

No one was hurt, no one got in trouble, no fights, house damage minimized, everyone had fun, and profits were maximized.

My immature adolescent brain was from that point on addicted to creating ways to provide value for people.

And the Interview Results?

It was a risk when I decided to be 100% candid and myself. Perhaps it showed (for better or worst) where I came from, my scrappiness, and my authentic love for making services people enjoy.

In the end, I got the job offer. I was told by the interviewer, which asked me the entrepreneur question, that he was surprised at my response. But in the end (I believe), he was more impressed than shocked by my ability to be creative in starting and running a “business”.

All business founders probably have a few early childhood hustle experiences which bring them to a life of creativity, authenticity and uncertainty — these would be the seeds of making an entrepreneur.

What experience did you have that led you to believe you are an entrepreneur?


*Note: I in no way support or endorse underaged drinking. Always be responsible when drinking alcohol regardless of your age. Strange that I have to say this explicitly, however, I prefer to avoid hate messages/comments/mail. Cheers!

About me: I’m mostly focused on internet growth, culture, and startups and am the COO at Wafer Inc. When I can find time between being a co-founder and life I enjoy writing, mostly here and occasionally on LinkedIn.


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