April 15, 2019 · Chapter5 MyAwesomeBook family

Chapter 5: My brother died. Then I quit my job

I'm writing a book (errrr, a collection of essays? blog posts? whatever) about lessons from my path to entrepreneurship. I'm clearly not publishing them in any discerning order since I went from Chapter 0 to Chapter 5. Sometimes the stories are funny. Sometimes they're not. This is probably the most pivotal of stories in my founder journey because without it, I'd still be working for some other asshole.

9 years ago today, April 15th, tax day, I got a call at 6:30 in the morning. It goes without saying that a call that early is unusual, especially when you see on caller ID its your mom calling. There’s this instinctive thing that happens when you see a phone call at a weird time from a loved one; you sorta know the news ain’t gonna be good. Moms don't usually call at the crack of dawn to ask why you haven't sent over the family photos. When I answered and heard my step dad's voice, my stomach sank. The news: my youngest brother had taken his own life earlier in the morning. He was 2 years younger than me and, depending on the day, either my biggest arch-enemy or my biggest fan.

To say the experience was jarring would be an understatement. Despite the fact that Andy and I had spent more time fighting in our 30 years together, we had grown closer in the last year or so of his life. I’d send him a box of books when he got bored, we’d get on the phone every few weeks and talk baseball or football or whatever random thing floated through heads. Even though we'd started to become friends again when he died, I was still unsure of how he really felt about me. And I was unsure how I really felt about him. We were both cautious with each other. The relationship between brothers can either be extremely close or somewhat strained. We were trying to figure out where we were with each other that last year.

At his funeral, more than one of his friends came up to me and said how often Andy would brag on his older brother TJ for having gone to college. My brother, who so thoroughly terrorized me growing up (and I him, trust me) was proud of me. It's one of those things that moved me then and still sticks with me to this day.

The next 6 months were a hazy blur. Andy dying had pulled open this well of emotion that normally stayed fairly closed off. I realized a lot about myself in that 6 months. At the time I had worked my way up to running the technology group at a growth stage startup. I was fairly young still (32 at the time) and managing 3 different groups consisting of about 25 people. I could come and go as I pleased. I had a great team. And I made good money. Life was good! Except it ... wasn't.

I had always loved the idea of starting my own company. I wrote about my very first "company" when I was in 5th grade (hahaha, "company". you get the idea). And I have a forthcoming entry about a company I started with my college roommates. I did a lot of freelance work, started a few side hustle products, etc, etc. But I'd never taken the plunge: quit a job, live off savings, and pursue my own company full time. I was too afraid. I was worried that all of these things that I'd worked so hard for in college and the beginning of my career would evaporate. It was that moment when I realized what true happiness was for me. It wasn't a nice house or a car that was paid off or any of the things that I thought made me happy. What I learned in those 6 months of haziness is that happiness, for me, was building something of my own.

At the end of those 6 months my head started to clear. It's cliche but his death helped remind me that life is short. Mortality is not a thing that 32 year olds normally think about, but Andy put that on my plate and I wasn't going to overlook it. I was going to spend my hopefully long life doing what I really wanted to and not was expected of me.

As I sit here and look at nearly 9 years of entrepreneurship, I think about my brother almost every day. I miss him and I hope he'd be proud of what I'm doing now.