HH What No One Tells You About Being An Entrepreneur

I’ve been an entrepreneur for 5 years. After the first 2 years, I was broke. I had spent those first 2 years as an entrepreneur making less money than I had made when I was in my first job out of graduate school. Much less. I had a business partner during those 2 years. I left him. They call it a “dissolution.” I call it a break up.

When the break up was complete, I launched my agency. It was the first time I was 100% on my own. For the first 4 months, I generated a grand total $500. My Father in law had to buy me a laptop. I borrowed money from him to pay my mortgage. My wife was supporting our family. Then something happened.

Salesforce acquired Buddy Media (the company who had fired me two years prior). This was an important event because I was smart enough to buy my small bit of vested equity on my way out the door. I was going to make money. I had gotten lucky.

When I received the check from Buddy Media, I dropped to my knees and wept in the foyer of my home. I pulled myself up to sit on the steps and stared at the check. With tears dripping down my face, I swore that I’d never find myself in that position ever again. It embarrassed me that I cried. But I did. Like a baby. I took that money and leaned into my agency. We hired, closed deals and got into office space. I had no idea what I was doing. It was terrifying.

My Father was deteriorating from ALS. A terminal, and brutal disease. It tore his body apart. I would self medicate and drink myself numb every night. Scotch. I couldn’t believe he was dying. I would wake up hung over ever morning, and drag myself into the office. I should have been skipping into the office.

Every day for the past 5 years, I thought my Dad was going to die, until he finally did. Every day for 5 years I thought my clients were going to fire us, until they finally did. Every day for 5 years it terrified me that I wouldn’t make payroll, until I finally missed it. Entrepreneurship? Torture.