The Founding of The Flipside, Part I

It feels like you guys have joined another tribe

“It feels like you guys have joined another tribe,” Drew Condon, Mylestone’s Head of Product, submitted.

And it’s true, we had. We just didn’t know it yet.

And this is the dangerous thing about founder curiosity.

Sometime around 2015, Jim Myers and I founded a company in the death industry. Mylestone’s premise was simple: when people passed, their history and their stories were lost into the ether; digital artifacts and photographs fared no better, distributed broadly amongst family members and friends. For many the deceased exist in our lives as much as our living counterparts. There just had to be a better way.

I know, I know, you’re dying to know the details.

We got to work and, with a small collection of startup bandits and a stash of venture capital, went about pivoting our way into solving the opportunity. We tinkered with products for family members to record stories; we developed Alexa and photo-journal integrations; we performed customer discovery, spending hundreds of hours with those grieving lost loved ones (lots and lots of tears were shed). And we toured more than 100 funeral homes to understand their inner workings.

But by year two we determined that preserving memories of the deceased was, well, a dead end.

You see no one individual grieves the same as another; there are 100 answers to 50 questions about how someone seeks to preserve the memory of a deceased loved one. And a real challenge: Funeral directors — while possibly the most humane people in the world — have a sustainable business model that doesn’t require any need for technical evolution. They have, put somewhat ghastly, endless supply.

So, well…sorry for coffin?

However, in true startup fashion, we stumbled our way to the fact that people sought to preserve their stories while they were still on this side of the astral plane. This so that, in an unfortunate state of finding themselves deceased, their loved ones would be able to remember them forever. ///

So our product evolved as follows:

You provided Mylestone with access to your digital photo repository, and one of our 1000+ digital biographers would get to work. One afternoon you’d receive a text, “Hey it’s Scotty from Mylestone. Was checking out your photos. Love this one,” and Scotty would send your very own photo to you. “Looks like you’re in Morocco maybe? That’s a pretty cool scarf — did you buy that in a bazaar?” And so a sort of photographic penpal relationship would form; a dialogue would ensue, and each picture would be annotated, preserving history along the way.

This worked. Users began paying a monthly fee for the service and biographers felt valued; relationships were formed. And you could see future revenue from photo books and the like.

But an insurmountable challenge: We weren’t solving our vision of helping people at a time of crisis. Rather, at best, we had created some form of photographic ego-stroking or narcissistic navel gazing. Our pivot may have provided business promise, but spiritually it was not exactly for us.

Sometime in late 2016, Jim and I grabbed lunch with two friends at Fidelity, Matt Walsh and Hadley Stern, who happened to be working on early skunkworks projects on cryptocurrencies. They reflected that Fidelity’s powerhouse CEO, Abby Johnston, even had a bitcoin mining rig in her office. “We don’t know a lot about the death industry,” they chimed in near robot synchronicity, “but this is the future. And you should be in it.”

And so down the red-pill-rabbithole we tumbled — and what started as a curious itch burned into a passion. Jim and I would lead Mylestone during the day, only to trot off into a conference room by night, where we’d try to crack the code on the challenges of trading crypto. At this time it was a tangled web; a cat’s cradle of exchange listings and wallet management, of newly formed assets and of non-existent USD to crypto onramps.

Pretty soon word got out about our evening activities. Friends began knocking: “Hey I hear you’re able to get crypto, can I give you some money to buy me some?”

And so we formed a Club, a legal entity. Shortly, millions in assets were available, and Jim and I had taken a small set of fees for organizing everything. In a few months, we had generated more revenue than Mylestone had in the previous two years. Then, in one of the smartest moves we ever made, we called our brilliant data scientist friend Eric Stone, a co-worker from previous ventures, to borrow his swing-trading algorithms and statistical noodlings.

One evening, late, Jim and I sat crouched behind two computer screens in a windowless, plain, conference room on Tremont Street in Boston. Drew tapped on the door, we beckoned him in and he uttered those prescient words, reflecting our shift in tribalism. We were caught off guard and, of course, we denied everything.

“No, no no,” we pleaded. “We’re all in on Mylestone, we’re just having a bit of fun over here. Think nothing of it,” like two kids caught with their hands in a candy jar.

Drew nodded, but didn’t buy it for a minute.

And so Jim and I faced an identity crisis:

Were we leaders of a venture-backed death-industry memorialization startup that was just finding liftoff?

Or were we mercenary traders at the forefront of a financial revolution. Could founders be both?

In an effort to understand our own quandary, Jim and I trotted off to see an old business acquaintance, Jeremy Alliare, the CEO of crypto startup Circle. We sought his input and insight, and explained our day jobs and our evening side hustle. Jeremy nodded patiently and offered everything he knew about blockchains and cryptocurrencies.

On the way out, I shook his hand, offered appreciation for his time, and said I’d let him know what we decided to do.

Jeremy pulled me in close.

He stared me straight in the eyes and committed us to our future.

“You’ve already decided,” he stipulated, and, indeed, we probably had.

The Founding of The Flipside, Part II to follow