It wasn’t until after I seriously contemplated suicide that I was ready to handle a $30 million check.
I closed the doors of my first start-up in the summer of 2001. I was throughly broke, depressed, and feeling the burden of losing hundreds of thousands of dollars of other people’s money. Loneliness, darkness, hopelessness… those words don’t capture the feeling of the profound self-doubt that sets in after a failure. Loneliness. Darkness. Hopelessness. Those words describe the environment of depression. Self-doubt? That shakes you to the core and starts a fracture in your identity that makes you question if you should even exist anymore.
Then, a few short months after closing up my dreams, the planes hit the Twin Towers. I was 23-years-old, just a year older than the late Ilya Zhitomirskiy of Diaspora. It started a descent down to a depth I never knew could exist. Whatever it was, it was over. I knew things would get better. It probably would get better, but I just lost the energy and will to try. Until that point, my life had been a series of struggles and successes. Life was hard, but if you worked hard, if you suffered, if you lived for your dreams, it wasn’t supposed to end this way. There were plenty of examples of winners. People were getting funding, going public, creating change. Was I not meant to be an entrepreneur? Will I never get to pursue my dreams again?
I spent a week in my room with the lights off and cut off from the world, thinking of the best way to exit this failure. Death was a good option — and it got better by the day.
I don’t remember why I left my room. The most meaningful act I performed on my long climb out was to leave that room. It was the best decision I made in my life. I left that room and I got back to my job managing a very dysfunctional Internet radio startup where I was the cause of the dysfunction. It was a actually a positive thing that I left that room to leave a really bad situation to go to a bad situation.
It wasn’t for several months that death no longer became an option, but leaving that room and dealing with reality was the best antidote to a make-belief world where life just wasn’t worth it. When I was fantasizing about death as the panacea, the harshness of reality actually helped — it presented me with problems that I could actually solve.
Nine years after I left that room, I would call Brad Feld to invest $30 million in my odd-ball company. Before I picked up the phone, I thought long and hard about losing that money — every single penny of it. And I was OK with it. Failure is an option, and a real risk. Failure and risk are things entrepreneurs understand well, and learn to manage. However, death isn’t an option, it’s an inevitability. And before I die, I want to take as many swings at the fence as I can.
For those of you who struggle with this, I’d encourage you to keep walking out that door everyday.
Ilya, I’m so sorry that we didn’t know. From a long line of entrepreneurs who suffered alone and quietly under our own self-doubt, I wish I could talk to you and tell you to bash the shit out of your own self-doubt, or just even slink away with your tail tucked between your legs — either way, the world would have let you take more swings at the fences.