Startup Step-By-Step: Down

A year ago, after closing my first startup, I attended one of those conferences that you’re supposed to attend. There were a lot of old friends there, folks who I hadn’t seen in a while, and there was the usual collection of panels and panelists, Power Points and Pellegrino. As I stood in a sun-full room clutching a coffee someone asked me about my first startup.

The reaction was swift. First I felt the old gut churning, the fear. It was like bringing up the name of a family member who had recently died, like raising old ghosts. I started to talk – “We just were too early, it was a good experience” – but then it got harder and harder. A failure is a blow. It’s a pop to the nose, tears welling up not out of sadness but out of surprise and anger and disappointment. Disappointment in yourself, in your choices, in your inability to stick to it. A feeling that you should have done better. A feeling that you rarely get as an adult in a cubicle, sitting and waiting for the next paycheck. It’s a feeling that I knew I needed to feel but it was also a feeling that hurt to the core.

This isn’t a post about crying at a tech conference. That happened and it was at once embarrassing and enlightening. It’s a post about one or two things you’ll feel when you build and how to cope.

The brogrammer will say that you’re not ready to be an entrepreneur if you can’t handle this shit. He’s wrong and he’ll get his soon enough. This is a human activity more akin to art than science. Any art that doesn’t make you feel something is a waste of your time.

So when you embark on this remember that what you’re feeling is perfectly normal and perfectly dreadful. First, listen to your body. When we were raising funds in New York and the Valley I’d wake up in a panic. I’d wake up not wanting to work. For the first time in my career I didn’t want to go to my computer and get started. I was gaining weight. My guts were broken. The fear was palpable.

I tried to fix things through work but, and this is something I took with me to my new startup, Jaywalk, I found that what I needed was to walk or run. I needed to get out. Some kind of movement tended to calm me gave me a moment to solve my problems. One particularly rough day I walked 80 blocks through my neighborhood, from down near Green-Wood Cemetery to Downtown Brooklyn. It felt good to be out. I started running four times a week recently and I feel much better. I learned from my friend Rich that walking releases endorphins and helps the body heal itself.

Further, when you feel this way, when you wake up in a sweat day after day, there are few things to check. First, tell your partners or programmers what you’d like to change. There is always something – in our case we’d have long meandering talks about stuff that didn’t exist yet, a problem that is symptomatic of having a bad tech stack. In retrospect I couldn’t have changed much about that experience but you’ll find that you often feel better when your tech is going right. Find the thing you need to change. A startup is an engine for experimentation. Experiment in order to hone in on the true problem.

Raising is also a stressor. Again, the old Brosephian adage, “Suck it up, you big baby” doesn’t apply here. I’ve heard from hundreds of founders, candidly, that they hated raising. The rejection, the waiting, the curt emails back – all of these are arrows to the back. Eventually you fall. If you can bootstrap, do it. VC is in a strange place right now and the old days of team and a dream are over. Until new models firm up I’d honestly explore equity crowdfunding and crypto-based raises. I’ll write more on that later.

I also recommend something that I’ve been trying, a form of behavioral therapy. I ask myself why I feel this way, what immediately preceded the feeling, and then work out a solution. It’s drastically simplified but it helps.

Startups are full of stress. The stress of managing people, of quitting your full-time job, of handling the ups and downs of startup life all lead to a dangerous mix.

That mix is where I really wanted to go today.

Startups are dangerous in that they bring you the brink again and again. They can destroy you. I’ve seen too many young, promising entrepreneurs end their lives because of some perceived failure.

May is Mental Health Awareness Month. Brad Feld and his friend Chris Heivly have already written about this. Please read what they have to say. Their stories are far deeper than mine. In short, given the right ingredients, startups can bring you to the point of depression or and exacerbate mental illness. If you or someone you love are facing this then please, please get help. I’ve offered a few coping mechanisms here but I have never been visited by evil thoughts. I’ve been visited by sadness and fear and disappointment and disillusionment and I’ve tried to fix them as best I could. I often failed but I got back up. I want all of us to get out of this alive.

If you need help please consider visiting The Stability Network or FIRE Within. Visit The National Suicide Prevention Lifeline and Chat or call 1-800-273-8255. Talk someone you trust. If you’d like to chat I’m johnnybnyc on Skype and my Facebook Messages is open.

There will be a day when you cry for lost opportunities. There will be a day when you miss what could have been. And there will be a day, not long from now, when it all makes sense and you can finally smile.

Image via Unsplash/Christian Puta