How I Became an Entrepreneur by Watching the Daily Life of a Successful Entrepreneur

My most recent endeavor: Source.

By: Andrew Lindsey

What we do with our lives can largely be attributed to the direction our parents encourage us to go, in one way or another. I grew up in a household of business people. My father ran a large multinational civil engineering company and my mother works as an independent school CFO and assistant head of school after leaving her job as an investment banker in New York City. She is also, now, the Chairman and CEO now of my late father’s corporation. Growing up with two very A-type parents can be both intimidating and stressful. My mother told me I could do whatever I wanted to do, but I would need to work extremely hard if I wanted to be successful. My father never accepted less than perfection as a standard. While I knew I wanted to go into business, I never expected to go in the direction that I have. The reason — I became an entrepreneur despite and against the advice of my parents, especially my father who was an entrepreneur himself. I would like to tell you about my childhood with an entrepreneur as a father and how he influenced me to become an entrepreneur myself.

When I was growing up, watching my dad was something of a clockwork system. When I woke up in the morning, he was either on the phone or hastily eating a granola bar and peanut butter before rushing out the door with a determined look on his face. When I got home at night, around 5 pm or so, there was still about 3 hours before he got home. After walking through the door, he would either immediately continue working or attempt to decompress — something he was never really good at and which largely consisted of removing his tie. I came to understand early on that this behavior was in my dad’s nature, he was highly driven and methodical; he had, in fact, been number one in his class at the Air Force Academy. My father loved what he did and he was able to thrive in stressful situations. It wasn’t long before I formed opinions of his work behavior, telling myself, “I never ever want to do whatever it is that he is doing.” A couple years down the road, my parents started to teach me a few things about business and management. Nothing too complex, essentially a basic carrots and sticks model — I was probably ten at the time.

While I grew up, so did my dad’s business. He started leaving the country more and more often for weeks at a time. I became intrigued by his frequent adventures to South America and the Middle East, although the level of work he put into his company sometimes worried me. He would fly home and walk through the door around 2AM or 3AM and then begin a conference call at about 5 in the morning- working through the time difference half way around the world. While he seemed stressed, he never seemed to get tired. It was as if he had a limitless amount of energy. When I started to think about what to do with my life about halfway through high school, I asked for my dad’s opinion. He replied to my question as directly as possible, but surprised me when he asserted, “Don’t start your own business if you want free time and the ability to relax.” What was interesting about this piece of advice was that my dad loved what he did; he loved being a civil engineer; he loved the art of the deal and the deal after that. Everyday, it was as if he focused entirely on his life’s passion project. And who said I wanted to relax? I took my dad’s advice to initially approach the idea of entrepreneurship cautiously, although ultimately this would end up being far from the case.

In 2010, I started my sophomore year of college with no serious idea of what I wanted to do with my life and no clue about what I wanted to study. Without a sense of direction, my drive to succeed in school was seriously challenged and gradually evaporated. By the end of the year, I found out that my dad was diagnosed with terminal cancer and given what I considered to be a death sentence. He was Superman to me and frankly I never thought he would die. My life turned upside down overnight. I immediately scaled back to part-time classes in school and decided to use my additional time to think about my future. During this time, I got antsy…very antsy. I started traveling around going to music festivals and concerts, something that became somewhat of a passion for me. This was partially due to too much free time and a good deal of anxiety around my dad’s health. After about three months of doing this, I became interested in the business behind concert production. I returned to school to meet with my best friends, who were also my roommates at the time, to talk to them about starting a company and the potential for growth in the rapidly expanding music industry. After a few weeks of deliberation, my two friends and I decided to start our first company in December of 2010, Whirl Time Music, doing concerts in the college market. One thing we knew for sure was that we knew nothing about the concert promotion and production industry but we loved music enough to learn a lot about it.

The first step was to outline a business plan, incorporate, and secure financing. Without a thorough knowledge of the industry, we reached out to friends or friends-of-friends to gain insight in what went into the concert business. After getting a general idea of the industry, the next step was to incorporate, which would require financing. I figured I could ask my parents to help move the company forward, but I found out that this would be more of a process than I had anticipated. I called my mother first, who suggested I reach out to my father. I was concerned to say the least — as I mentioned above, he attended a military academy and exuded that trait, even after his diagnosis. I mustered up the strength to ask my dad, but he immediately noted that if we were going to work together business-to-business, I would have to go the same route any other business did. The first thing I would have to do was make an appointment with his secretary. I booked an appointment about two weeks out and began to prepare for what would be a meeting that would change my life forever.

When the meeting was 24 hours out, I started to convince myself that I was completely prepared and that I would nail it. I woke up the following morning, got all the materials together, and headed to my dad’s office for the meeting. When I arrived at his building, the receptionist escorted me to a large all-glass conference room where I would wait for my dad to get off a conference call. I knew I would not have much time available, but the nerves started to set in about his reaction to my business plan. The growing anxiety felt like I had a pit in my stomach and I wanted to throw up. I sat there tapping my leg and sweating profusely until my dad walked through the door. He was dressed in a suit with the appearance of having a million things on his mind, the least of which was his health. He gave me a hug and subsequently asked, “so, what are you doing and what do you need?” It felt like I couldn’t get the words out fast enough. After the initial pitch, I felt comfortable for a brief second until the questions came. My dad tore apart my business plan, poked holes in my knowledge of the market and business, and told me to come back when I actually had “something worth investing in.” I was crushed but I also fell in love with business and entrepreneurship right there and then. My dad challenged me and treated my business like any other potential investment — with honesty and blunt criticism. The next few weeks I rarely slept while trying to solidify my business and pitch. I booked another appointment with my dad about a month later and proved that the company was worth investing in. I was hooked; I was an entrepreneur.

Over the next few years, my company put together numerous concerts that I had never imagined possible, but my dad’s sickness continued to get worse. While my dad’s health declined, he never once hinted at that fact. He would spend hours on conference calls while in the intensive care unit to ensure that his business was running smoothly. He was the epitome of dedication, something I aspired to be. He would tell me regularly how proud of me he was, something that weighed heavier than gold. As his health proceeded to get worse, I scaled back my role as CEO and started to spend time at home more regularly. My dad’s frailty was constantly on my mind. By May of 2013, my dad’s cancer had spread all over his body and he was looking worse by the day. On May 17th, I spent most of the day with my dad, trying to teach him to do simple tasks because tumors in his brain were impairing his cognitive ability. Seeing my dad this way crushed me in a way I never thought possible. Before leaving the hospital for the night, my dad made me promise that I would return to school and finish my degree. He died the next morning. The next year I returned to school, but not before starting my second company, Source.

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