309: What my middle-class dad taught me that set me up for generational wealth

My father taught me a lot about business, entrepreneurship, and life, and it’s thanks to him that I’ve been able to build generational wealth for my family. My father was an entrepreneur at heart, and what he did for me set me up for success.

First and foremost, my dad taught me to be resourceful. We were a middle-class family–we didn’t have to worry about money, but we never had a lot saved up and didn’t have luxuries like second homes, fancy vacations, or frequent dinners out. Whenever I would ask my dad a question or for advice, he would never give me the answer or tell me what to do. He would ask me question after question that would frame my thinking until I came to the answer myself. In short, he taught me that I could figure things out.

This infuriated me when I was younger, but it kickstarted my journey as an entrepreneur. It taught me that even people who lead others don’t have all the answers to life, because there aren’t really a ton of right answers. We’re taught as children that there are right and wrong approaches to things, but in reality there’s rarely one correct way to think about a problem. This resourcefulness gave me the confidence to start thinking about answers for myself, and the realization that it doesn’t take somebody special to figure things out taught me that I could be an entrepreneur. I know that I can be in a sticky situation with no right answer and be confident enough to make a rational decision.

My dad also sat me down when I was 13 and taught me about business, even though I tried to avoid it. We were living in Indiana, and my dad was working for a development company that needed support mowing grass on properties. My dad didn’t just get me to do the work, he put me in business as a lawn care operator. I was in charge of setting my bid, setting up a P&L, calculating expenses, and even paying my dad to lease the mower and my mom to drive me to the job.

Immediately I was miserable and wanted to quit, but my dad told me to get through two weeks, get my first check in the mail, and then tell him if I still felt like quitting. So I set myself up to work for $45/hour and my bid was accepted, thus beginning my extremely profitable lawn care business that gained customers over the years. I even hired a high school senior to drive me around and help me mow for $15/hour so I didn’t have to rely on my mom.

My dad’s lessons changed my life forever, and they shifted the trajectory of my entire family tree. I was able to walk around life with a different way of thinking about business and the economy, and that led to my first storage business when I realized that a really profitable competitor in town wasn’t executing well. These lessons led to me going from a middle-class guy from Indiana to building generational wealth and the life that I want. All it takes to put yourself out there is to think about things in the right way.

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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.