45 Days — Chapter 2— The Seven Stages of Grief

“45 Days” is a non-fiction account of my experience as the Founder of Rude Media between May 1, 2016 and June 15, 2016. 45 Days was written starting on June 16th, initially as a therapeutic effort to process my experiences internally, as well as to try to distill down an experience that very few Founders have shared openly.

June 17th — I’ve arrived in New York City, but I’m still jet-lagged. I always enjoy east-to-west jet lag, because, for just a few days, I become a morning person. We went running at 7AM through Central Park, before it got too hot to run, and got our ritual morning bagel. God I love bagels.

I made sure before leaving Paris that I got through as many meetings as possible — they will inevitably spill over into July, although I would’ve loved a clean break, but I was sufficiently happy with how the last few days before leaving that I was able to almost entirely disconnect from work. We met with an old friend for lunch, and then went for a walk on the High Line. It was more touristy than I can remember — we went 2 1/2 years ago in one of NYC’s famous “worst winters since the last one.” There were more plants, but also more tourists. Even when I’m a tourist, I hate tourists. Selfie sticks and subway maps, mundane questions and self-evident observations — it brings out the cynic in me, but also the people-watcher. God I love people-watching.

Part of vacation is about disconnecting from work, but, for me at least, part of it is always about processing work, and watching taxi cabs drive under the High Line is as therapy for the mind.

I saw tourists try to flag down a taxi just like Carrie Bradshaw would.

I saw eyes light up as they stared up at skyscrapers.

I saw families queueing for the toilet.

I saw selfie sticks. God I hate selfie sticks.

People-watching can be very emotional — I absorbed theirs, I reflected upon my own.

Chapter 2: The Seven Stages of Grief

After I told my team that we only have 45 days of runway left, I spent the whole weekend alone in the office — not working, just… bouder is the word in French. I played foosball with myself, as I did often when I was on a boring call, or trying to think through the best approach to a situation. I played guitar loudly and sung songs that I wrote as a teenager — the angst was appropriate 10 years later, I thought to myself.

I stared at a plaque in our bathroom that I had screwed into the door when we moved in. It was something my mother had given me years ago, that I had kept as a reminder of what I was pushing towards.

My mother raised my brother & I pretty much alone in the Silicon Valley: at least from age 6 to age 16. She had moved out there with my Dad in the late eighties to work for tech, because that’s where you went if you were interested in computers: I always like to joke that my Dad went to SXSW before it was cool — there’s still a copy of a press release his company put out in 1997 in Austin.

Despite their Silicon Valley status, my mother has always been quite risk averse. Maybe because she was divorced — entrepreneurial failure and marital failure are different flavors of the same drink — or maybe because she was a union woman, used to stability. She also lived through the Silicon Valley bubble bursting — looking back, I can only imagine how tough that was.

Regardless, she was the type of woman who, even after I had raised a round of funding and had hired a handful of employees, would ask me “Do you think Google would ever acquire you?” — that was her subtle way of suggesting she’d like me back in Mountain View.

The plaque I was staring at read:

“If at first you don’t succeed, redefine success.”

I hated this saying. It was a call for setting lower standards, for giving up, for accepting mediocrity, which was something I pushed actively against with Rude Media.

I hated media companies, how they had been so foolish as to let their dependence on advertising revenue dictate their editorial strategy, how they invested so little in improving journalism and so much in retargeting social viral gifs. That was why we opted out of advertising, and opted to hiring engineers — against my better judgment, I knew I couldn’t build yet another mediocre media startup, so I decided to go big or go home. Home, it would seem, was looking increasingly like my fate — my mother would be so happy to hear it, I told myself.

During that weekend, I consciously forced myself through as many of the seven stages of grief as I could, as quickly as I could.

Shock was tough — I was still receiving email requests from partners, and sending invoices for events I wasn’t sure would happen. All that momentum we had built up by hiring and pushing big doesn’t just stop as soon as you hit crisis mode: venue owners were looking for us to sign contracts, to announce our fall season events. Users were still signing up for Disclose every day — more & more, in fact — and PR firms wanted to make meetings to learn more.

I still had responsibilities to the company, but where was the motivation? Fighting on the front lines makes sense if you know your purpose — my purpose was on life support, and if I didn’t believe it could survive, then how could it?

Denial never comes the way you’d expect it, and I would be no different. I didn’t deny the gravity of the situation — I had, after all, made the conscious decision to alert my team in order to give them time to react, plan, and process — but I began to deny what it meant to me. For the past four years, I had managed to pay myself a salary by running a blog, to build a worldwide network of people who, for whatever reason, wanted to know me and be a part of what we were doing, and I had even managed to employ a dozen great people during that time. How could it be called failure when I had grown so much, learned so much, gained so much in the process?

And then that voice creeps out from the shadows of the darkest part of my brain, reminding me that, there I was, redefining success.

Bargaining, Guilt, and Anger aren’t really my strong suits. My mathematical mindset slips in there and reminds me 1) There is no one to bargain with but myself 2) guilt is only for those who regret, and I regret nothing, and 3) anger won’t get my any closer to a solution. OK. So maybe I broken a plate or two, but I didn’t beat myself up over it or think that by doing that I would get something in return, so that’s one out of three.

In truth, the worst moments are the ones where you let yourself entertain ‘what if’ thoughts. What if I had never been so foolish as to think I could build a product inside a media company? What if I stopped tech altogether? I’d always wanted to be a chef (& a teacher, and an architect, and a lawyer for a brief period of time following a Law & Order marathon). Bargaining is entertaining those thoughts. Guilt is legitimizing alternate versions of your story. And anger is the whiplash you get when you snap back to reality.

Depression has always been a strong suit of mine, if I do say so myself. While guilt is, for me, an irrational feeling that I don’t much identify with, depression is one I know all too well. Let’s just say, I grew up listening to Nirvana. A lot.

It’s a short step for entrepreneurs to get depressed. It generally goes something like this: I am an entrepreneur because the only difference between employee & entrepreneur is that an employee’s source of stress is external (a boss), and an entrepreneur’s source of stress is internal (their own drive). Entrepreneurs can reduce stress by reducing drive, where as employees have to quit. In the same vein, entrepreneurs are solely responsible for any and every problem that their company faces. Failure, in that case, is entirely the entrepreneur’s fault — just as startup success is largely attributed to founders — and bearing the weight of imminent failure is enough to make anyone depressed.

I remember watching The Titanic when I was a boy — that moment as the water bursts through into the captain’s hull — wondering what good it could possibly do for the captain to go down with the ship. Now I understood — that overwhelming feeling that everything & everyone around you is your responsibility, it feels like the best thing to do is to bury yourself in your failure, to let it consume you. You deserve it.

I was halfway to acceptance when I realized that accepting meant giving up, and I still had 45 days left. 45 days had been plenty of time in the past to organize conferences, raise rounds of funding, hire great people, convince the city of Paris to let us fly drones on busy shopping streets. Why, now, would these 45 days be any different?

45 days was enough time to identify what could be saved and what couldn’t, to find a new investor, to be acquired, to reinvigorate our revenue stream, to salvage what we could. I had always told myself that you only fail when you stop trying, and, with no many questions unanswered, stopping just wasn’t an option. I owed it to my team, my investors, and surtout to myself, to try to find a path to success, even if that meant redefining success. Damnit, Mom.

The thought fluttered in my head — Had I made it to Hope or was I still stuck at Bargaining? — but I grabbed my keys and ran out the door to go for a run before I could let the thought linger long enough. I didn’t have time to wonder where my emotional state was: I had 45 days to save my company.

To continue reading 45 Days, feel free to click through the Table of Contents below, or subscribe to my posts on Medium — I’ll be adding new chapters regularly.

• Chapter 1: The Last Meeting in April
• Chapter 2: The Seven Stages of Grief
• Chapter 3: Open Heart Surgery
• Chapter 4: It’s easy to Fire in France
• Chapter 5: Ephemeral. Exclusive. Entertaining.
• More Chapters published soon — Subscribe for updates!