DZ - 015

It’s a common thing for investors to be asked how they got into investing as there never seems to be a “normal” path into the industry. People come from all over, and their paths can be quite fascinating.

While I don’t find my path to be all that interesting, I still get asked about it a lot. I like to describe my path as having a set of motivators, instead of functional steps. I’ve done this for some reasons that I’ll get into later, but I’ve distilled these motivators into four main buckets, that at least in my mind, were and are the personal driving factors for having gotten into this industry.

Environment: My father is an entrepreneur, so I grew up with a parent working obsessively to get a business off the ground and I saw firsthand just how difficult and yet rewarding that process can be.

Some of my fondest memories as a child were waking up to the sound of my parents’ shower kicking on at 4am. I’d rush downstairs, hop on the couch and wait for my dad to come out to the family room dressed in his suit ready to go to work. He’d grab me a cup of cheerios, turn on cartoons, then leave. I’d fall back asleep, go to school, get home, have dinner with my mom and sisters. More often than not, while lying in bed, I’d hear his car pull into the driveway sometime around 10pm. Rinse, repeat. While most of my buddies’ parents had standard work hours, mine were gone most of the time. But even at a young age, I knew how hard my parents were working to make things better and that there’s something special about someone trying to carve out their own place and do things on their own terms. There’s no question that seeing this process as a child had a tremendous imprinting effect on me, and I always knew that I would be involved in entrepreneurship in some capacity or another.

History: My Great Grandfather, who passed away at a young age, had, during the depression, helped to get companies off the ground. He helped a few local entrepreneurs build their business plans, get loans (he gave some as well), and operate their businesses until they were up and running. A couple of these companies are still in existence, and my family uses one of them for both home and business services. It’s a rare thing that you can point to something your ancestors accomplished and see how that work has carried through and affected countless people long after they’ve been gone. The concept of that as a child was always striking to me. That my great grandfather, on my mother’s side, who died long before I was born, had helped entrepreneurs go through the same process that now many decades later my father and mother were going through. I’ve always thought that was incredible and represents for me one of the many reasons society can be such a great force for long lasting good.

Personality: I’ve hated school my whole life and found the process and design of the education system to be archaic and inefficient. Wherein every child is treated like a robot shipped from the same factory, and “differences” in robots are bugs that need to be ironed out. Think differently, and your operating system will be adjusted. I remember a specific instance in 1st grade where one of my classmates, who was exceptional at drawing, was made to feel dumb because he wasn’t picking up math at the rate “he was supposed to”. So here he was, at such an early stage of development, crying in front of his peers because math wasn’t his strong suit. And he had already been ingrained with the idea that if he wasn’t successful in this environment, he was destined to become a failure. That to me is a travesty, and yet is something that, in my opinion, happens countless times throughout one’s educational path. Talent being shunned or wasted because we’re more concerned with getting everyone to the “average” in all subjects, rather than accelerating the exceptional, and accepting a longer path for development in different areas. In general, I had this overwhelming feeling that I was wasting my life while sitting in class, and how depressing it was to me that I’d never be able to recuperate the lost time.

I can’t oversell just how much I loathed school. My parents will tell you I cried virtually every morning before class and would have so much anxiety on Sunday nights that I would sometimes dry heave and cry myself to sleep. The physical reactions lasted until middle school, but I never got over my hatred of the educational system.

During this same time period, my father would sometimes take me along to some of his job sites to see buildings being built, or to observe development conversations with clients that were leading the charge for a renovation or redesign. Walking around these job sites and seeing people in cubicles (very common back in those days) always reminded me of school. Rows and rows of people, blanketed in unnatural fluorescent lighting, counting the minutes until their next break, lunch, close, etc. Desperately not wanting to be where they were. As we’d walk by, heads would turn around to face us or pop up over the short walls like prairie dogs in a concrete encompassed jail block. These are just kids in desks, with a different list of daily tasks, but they still bring their lunch every day, and they talk about the same things every day, and while I know there are countless people that enjoy that life, just like there are countless people that enjoyed school, I knew there was no way in hell I was ever going to do that. I would rather be a stone mason, in midwest humidity, than work at a cubicle.

There have been a number of pop culture related attempts to describe this environment and anxiety that I’ve always felt, and what I thought life in the corporate cubicle jungle would be like. But I’ve never seen anything that quite describes it so well as the movie Brazil. Specifically, the DEE ZED STROKE O ONE FIVE scene.

Focus: One of the reasons I hated school so much was that I found it nearly impossible to focus while a teacher was lecturing. It’s not that I can’t focus entirely. I can zone out into a specific task or project for hours and hours without exiting it and in fact, I can get incredibly angry if I’m forced to leave that mental state. But my mind would wander endlessly during class lectures, and I had to devise schemes and systems so that I could keep up with the rest of the class, knowing that I wasn’t going to absorb much during my school hours and that I would have an extremely tough time focusing during tests. The point is, I find it almost impossible to focus on things I’m not interested in. If I am, I can lock in and stay in it until I think I’ve learned enough to be knowledgeable. I’ve always felt that my classmates had a superpower in their ability to focus and memorize what a teacher was discussing. I however always had to go home and try to teach myself the material by covering the book content over and over. The point is I knew I needed to find something where I could dig into the things that interest me and stay away from anything that doesn’t.

About a year after undergrad, I read an article on venture capital, and I was hooked. Here was a job where I could work with and hopefully help entrepreneurs, where I could perform deep dives into countless industries with varying problems needing to be solved, and where I wouldn’t have to be at a cubicle from 9 - 5. Creating the functional steps to get there was, of course, another story, and I’d have to make sacrifices in order to get to where I wanted. But one of the most difficult questions I find entrepreneurs have answering is “What do you want?” and I don’t think it’s possible to truly know why you’re doing something if you haven’t analyzed the motivations for trying to get there. These are some of mine.