A modified version of this appeared in The Guardian.

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A few years ago I sat on the phone, as a first-time-CEO in my 20s, trying to convince a woman to buy a $1,799 necklace filled with her mother’s ashes:

“Well, Katherine. It’s really beautiful.” I paused for dramatic effect. “We take a charm that you like, let’s say a dove, or a cross -- or maybe something that meant something to Marcella. And then we fill it with some of her ashes. Whenever you wear it, it’s like Marcella is with you...right next to your heart.”

Ending on the word “heart” made it feel more genuine, which made it more likely that we’d get a conversion. A conversion is the word we used to describe a successful transaction/deal/death.

But we had to be careful -- if we got too good at this, too pseudo-genuine, we’d wind up unable to shield our own states of mind from someone else’s grieving misery.

That’s what I learned when a customer service rep had a breakdown on the open floor of our WeWork.

“What’s wrong?” I asked.

“Well,” she sniffled, “I just got off the phone with this woman whose husband died. She has no kids and doesn’t think she’ll be able to afford staying in her home. Also, she might have cancer. It’s so sad.”

I waited for the part that concerned me.

“She doesn’t have money for the funeral”

Wow, that is sad. I thought.

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I often wonder how I ended up like that -- how I became someone I didn’t want to be. I like to think that it was all due to a culmination of circumstances beyond my control and that I was simply a victim of fate. But that’s never true. To be or not to be a funeral director, one always has a choice.

I wasn’t always an insider to death. I wasn’t born knowing the average cost of a funeral ($7k to $12k depending on who you ask), or the temperature at which you can store a dead body (39 °F). My journey began in 2014, on a cold snowy day in NYC. I got a call from a mentor of mine:

“Things are fine, Alex -- but my mother passed away last month.”

“I’m so sorry. How’re you coping?” I asked.

“It’s terrible. There’s so much paperwork. I’d pay thousands to make it go away.”

He asked me to start a business. Why he asked me, specifically, I’m not sure. I was 25, care-free and had just come out of the closet. Maybe he thought that if I was able to feign interest in sex with women for so long, I’d have no trouble acting my way through “I’m sorry for your loss”. Until then, my career had always been directionless. One startup I worked for helped companies get rid of punch cards, another helped consumers find cheap parking. Companies that succeeded at making money but failed to make an emotional impact. Perhaps working for a company that did both could be nice.

We came up with a premise: help families during end-of-life decisions. The startup was born, and we named her Grace.

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Grace was beautiful. A soft color-palette of light blues and pale yellows, a website with all the features you’d hope for. It was like Uber, but for cremations. Grace would help with the disposal of a body, the logistics of cancelling a NYTimes subscription, transferring a Chase asset, even deactivating Tinder - our startup was tackling the $20B funeral industry with a one-stop-solution for closing out someone’s life with just a few taps on your phone. But behind it all sat a young founder with no experience nor interest in death.

This became a problem rather quickly with investors:

“Alex, we like you. You seem very fun and...happy-go-lucky. With regard to the funeral industry, you don’t really have what we call ‘founder-market’ fit.”

Grace needed a raison d’etre.

A month later, my Great Uncle Jack died of pneumonia. I was sad, as we all are when anyone dies, but he and I weren’t particularly close. Regardless, this was an opportunity to be helpful. To learn.

I reached out to my aunt and cousins to assist in closing out his life. For investors, this became the emotional story that helped me fundraise and it was here that my days of having been trapped in the closet, as an actor of sorts, finally came of use:

“Well, New Investor. When my Uncle Jack died there was just so much to do. I was beside myself,” I cleared my already-clear throat. “Closing out the Chase account and the Verizon bill while helping my Aunt figure out what to do with his...well... you know....body…I...just wish there had been a service to take on some of the work,” I intentionally looked to the floor, “...something that could have given our family time and space to sit together when we needed to… You know,” I looked up. “To grieve.”

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There it was: Grace’s origin story.

I wasn’t proud of it then and I’m not proud of it now, but Grace was on a mission to provide a service to the world and we needed money to make that happen.

Four months later, we raised $2m -- a typical round in the $130B delusional venture capital market. With newly pocketed investor dollars, we relocated the company from New York to California -- to a state that combined less restrictive funeral laws with tech-forward residents who might be comfortable with an online funeral home.

We specifically chose Los Angeles. At 63,559 deaths per year, even if we ended up with a low conversion-to-close rate, LA would have enough mortality to keep us running for a while. And what a city it was. A place full of charlatans, where wannabe celebrities drove Benzes and hot Insta thots drove snake-oil CBD sales. It was just what we needed - a place where we fit in.

“Ma’am, of course. We’ve handled many cremations in Calexico,” wherever that was. “We’ll have your father back to you in a week -- ashes in hand.”

We had sales numbers to hit and assumed we’d figure it out along the way.

And figure it out we did. Little check marks of death on a whiteboard. We were highly unprofitable, barely breaking even on contribution margin, let alone adjusting for salaries and phone answering services and paying for flights to hospice conferences -- but that didn’t matter at the time. Our top-line cremation numbers were up, and like most startups, we were adapting and changing to meet the needs of demand.

I began to adapt as well. Like a phoenix, I was shedding the feathers of a weaker, more genuine Alex, in exchange for those of an emotional chameleon. Someone who was able to look a man in the eyes and talk to him about his mother who had just been put on hospice, which typically meant she would yield a conversion within 24 days. Knowing that I had to be there for him in order for the sale to close, while also knowing that her death was our gain. A battle easier fought when I could detach. When genuine compassion was not part of the sale.

Within a year, I passed a funeral director exam and then a life insurance exam, and months later had brokered a deal with a local hospital network whose electronic health record system automatically texted us each time a patient “Expired”. A family for us to call, - a fresh, potential conversion.

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One evening, I was on a date with a guy I liked. His name was Patrick. Patrick the accountant.

“So, Alex, what do you do for work?”

“Oh. Um. I’m in...healthcare. How about you?”

My phone buzzed.

*PATIENT 4327 - EXPIRED.*

“Sorry. Work stuff.”

*PATIENT 7645 - EXPIRED.* A beat. *PATIENT 7876 - EXPIRED.* The dead do not mind double texting.

“You can take that if you need to,” he said.

“No no no. They’ll be fine.”

They would not be.

The next morning, while Patrick slept soundly in my bed, dreaming whatever it is that accountants dream, I sat at my desk a few feet away, facing the wall, calling a client.

“Mrs. Tanning,” I said into my headset, as Patrick began to wake. “Hi, this is Alex from Grace. Yes. Um. So sorry, but we just found out that your husband is 307 pounds instead of the 285 you wrote down.”

Patrick tuned in, as one does, when overhearing a conversation like this.

“Well, ma’am, you see, the crematory charges more because heavier people take much longer to cremate,” I explained. “Depending on how overweight, it can be 8 to 12 hours instead of the typical 4-6. Plus they need to hire an extra person to lift him on and off of the tray. It’ll end up being another $75 or so.”

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She yelled and hung up. That was the last time I spoke with Mrs. Tanning. Or Patrick. A failed conversion on both the sale and the love interest. Both of them having seen the person I did not want to be.

Single and still lost, living in LA, I was a jester, an unproud merchant of death only telling the people about my work when it functioned as a punch-line.

And Grace was running out of money, as most startups do, when they hit top-line-revenue numbers for the sake of doing so, and have no North Star to keep them pointed in the right direction. It was about this time that my COO called:

“In order to increase our margins, we’re going to need to raise another round of funding to buy a crematory,” she said. “We’ll need $5m-$10m, which should last us 2-3 years. Someone will probably buy us after that. Maybe SCI or one of the larger conglomerates. You down?”

I took the weekend to mull it over. Reading Medium blogs titled things like “The Time I Shut Down My Startup”, or “The Time I Almost Shut Down My Startup, But Didn’t”, self-masturbatory thought pieces by writers desperate for validation. I looked through my phone and stared at my dating profile: my occupational title auto-generated from a LinkedIn API call “CEO at Grace Funeral Services of California.” Who wouldn’t want to date that guy?

I imagined saying yes to my COO. Buying a crematory with our team still in the throes of underfunded start-up-ness, one where everyone wears all hats - I thought of my gay little arms, hoisting Mr. Tanning’s 307-pound-body onto a tray. Me, opening up the oven door a few hours later, to see if his charred corpse needed more time.

I called her back.

“No,” I said. “I’m not down to buy a crematory.” I paused. “I’m out.”

And so I shut it down. I killed my darling baby Grace.

Shutting Grace down after four years was the best decision I made.

And I made it because eventually I grew tired of it all. Tired of walking the tightrope of being truly genuine and turning a profit. Of studying laws and facts about life celebrants and coroners and how to use packing forceps. Of walking up scared about slighting a family or losing a body. But most importantly, I felt tired of pretending to be someone I was not, because to quote investors, there truly was no “founder-market-fit.”

No raison d’etre.

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To be or not to be a funeral director or hospice nurse or anyone that spends every day of their life talking to people about the hardest days of theirs, one need be as apathetic as a sociopath or as compassionate as a priest, and it seems, like the most of us, that I am neither.

But hopefully someone else is, and hopefully they’re the latter.

Perhaps it’s the guy I chatted with out of Israel who wants to be the one-stop-shop for death and just raised $13m. Or maybe it’s the woman I read about who zips your corpse into a sexy leather suit of mushrooms and decomposes you to dust.

Either way, that someone isn’t me.

Seeing headlines inundated with COVID death tolls, my friends say things like:

“Alex, if Grace was still around you’d be making a fortune.”

Maybe. But I no longer look at life in that way. My days of hustling individuals at their darkest hour are gone while I figure out what to start next. Perhaps a business that does the world good. Something that transitions me far away from a past life in a WeWork filled with genuine-sounding phone calls that all seem to end on the word “heart”, towards a future life that not only sounds genuine, but actually is.

Yeah. I’ll start with that.

After all, I hear it helps with conversion.

—

My next piece will be about doing Ayahuasca.

It sucked.

Subscribe if you want me to send it along.

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Garden of Anxiety

A funeral startup [The Guardian]