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April 28, 2025

The Founding of The Flipside, Part V

Balter’s Essays of Mostly Acerbic Witticisms

Disappointment.

Frustration.

Betrayal.

Abandonment.

And, mostly, seething, brutal, unfettered anger.

I guess it could have gone worse. But it certainly - without a speck of a doubt - it couldn't have possibly gone better.

mylestone company toy edition

Parts I, II, III, IV


The Founding of the Flipside, Part V

This in the very same conference room where Jim and I had committed spiritual treachery and infidelity. This the same room we began trading crypto in the evenings, while maintaining Mylestone during the day. This the same room where Matt Walsh, of Fidelity's digital assets division, and soon to be co-founder of Castle Island Ventures, would come to whiteboard and strategize over dozens of evenings over many months. This where we hosted crypto club members for wallet ceremonies and crypto education sessions.

And so Jim and I dropped the hammer. "We are going to be shutting down Mylestone," I offered, loaded with guilt.

This particular conference room was windowless, apt for our secret missions, but hell, at this very moment, I was looking for any window to jump out of. Rays from blinding LED panel lights rained down on me, irradiating, yellow, a spotlight to our cowardice and deceit.

Certainly the plodding hairy beast of the question of 'why?' sauntered out of its cage, sniffing and growling full of rabies.

"Is it because of this crypto thing - the thing you promised was just something for fun?"

And so it was true, and so we admitted to the best of our ability that it was unfortunate innocence that suffocated our interest in Mylestone and led us down a path to a future that was filling us with inspiration.

We told the team no one would be coming with us: They weren't interested in crypto, they were interested in transforming memories.

A few accepted the fate, knowing startups are funky beasts and even if we had a few million to still play with, the die was cast. They offered thanks. Others didn't say much. They would be paid for a few more weeks and then it would be over. Equity worthless. Time spent learning, time spent building, time spent committed, poof, all gone.

Glass half empty, time wasted.

The truth is Mylestone had found some footing, and so a week or so later, we offered to Drew 'It- Feels-Like-You've-Joined-a-Different-Tribe' Condon the ability to take over the assets of the business.

He was interested. A hasty deal was constructed. I would remain chairman with a small % of ownership; Drew and a few other characters would continue to build.

It all seemed like a soft landing - Jim and I would move on to build Flipside, and Mylestone would exist in some other form in some other way to some other future outcome.

But it wasn't to be had.

Within weeks, the challenge of running the business with limited resources, with the founder passion drained like sewage from a drain pipe, just...well it just ran dry.

Users of the product were informed. Thousands of biographers were told their services wouldn't be needed anymore. Millions of photos and associated words were erased. Services were cancelled. Servers were shut down.

mylestone shuts down

All was forgotten until three months later.

A note from the head of Corporate Development at SmugMug, a photo service who we'd been plying a partnership with earlier in the year. They were checking in.

I told them sadly we had made the tough decision to shutter the service, end the business.

"Oh, that's too bad," they said. "We would have bought the company."

And with that a gut punch, a fist to the eye, a realization of things-that-could-have-been or stones that should have been overturned.

But they weren't. And that, well, that was the end of Mylestone.

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