Failing, To Succeed

I have to say, after 19 months of building this company, it feels like a bit of a failure.

Here’s one for you:

Last week, I officially transitioned out of the CEO role @ Mylestone. I’m remaining involved as Chairman, while Drew Condon — our amazing head of product — is taking over the day to day reins.

Is It A Failure?

Yeah, I know it’s the only way the company will actually succeed.

About two decades ago, a guy I’ll just call “snake eyes” (he was a bit weird and, well…his pupils were vertical slits) was gushing about witnessing a rhythmic paradox delivered by Phish drummer, Jon Fishman. Apparently, Fishman was going deeper and deeper into some syncopated pattern and eventually found himself stuck.

Snake Eyes argued, “he just drummed himself into a corner, and had nowhere else to go. So he just stopped altogether.”

The story always baffled me — how could someone drum themselves into a corner? (If anyone has an explanation for this, I’m all ears.)

Regardless, Snake Eyes had articulated our exact feeling after the first year of Mylestone.

Our mission was bold: to transform how people memorialized their deceased loved ones. No one went to cemeteries anymore —a socially connected world left an empty void for paying our respects over time, and we felt we identified a pretty major pain.

Many people told us our proposition — no matter how valid — would be very hard to deliver. They argued that countless others had tried and failed before; that the empathetic nature of Funeral Directors wasn’t enough to overcome the Funeral Industry’s technophobia, and it was hard to ignore their incredibly low motivation for change (geographic proximity was enough of a competitive advantage for most).

Our entrepreneurial bravado disagreed. So we got to work.

After a year of visiting 100s of Funeral Homes, and about a dozen product iterations, we came to the conclusion that the funeral code was, indeed, too complex. In January 2017, we began focusing instead on the living: we connected people’s digital photo libraries with a personal biography service.

It solved memorialization without the burden of grief.

We had plenty of capital.

Our team was lights out good.

But one thing was hard to ignore: overnight we transformed from a business that sold to funeral homes (B2B), to one that sold directly to consumers (B2C).

The past 11 months have been some of the most complex and unsettling of my startup career. The shoes never felt comfortable. Sure I was dancing, but it wasn’t with any sort of grace.

The reason: in a consumer (B2C) business, my super powers were on the sidelines. I’m really a B2B guy.

Of course, I set the vision. I managed the team. Worked on the culture. But underneath all that was the hard cold fact that I had no one to sell to. No one to build a partnership with. No one to B2B.

Our product team was focusing on customer interviews, willingness to pay discussions, and user experience road mapping; our tech team was building the tools to operationalize the customer’s needs. Our marketers were driving traffic. And I was finding myself more and more a guiding light than a driving force.

A company must be wound around the CEOs specific skill. If it isn’t, no matter the hustle, no matter the willingness, drive, focus, creativity — it will always be less than enough.

Simply put, it’s time for the company to be wound around another persons axle.

Let’s cheer on Drew as he pushes it into third to climb that hill.

Originally published on Dave Balter.

Please offer a heartfelt motivational clap for Drew and his team as they get their B2C show on the road!