Note to Flipside: 5/10/24

You’ll all be an ex-employee someday

Dave Balter
3 min readMay 31, 2024

We’ll all be an ex-employee someday, was a common refrain delivered by Howard Kogan, Flipside’s COO circa 2021–2022.

I’ll be fresh: It always bothered me.

It bothered me. Because it’s true.

Sure, in a few outstanding scenarios, the truth was a reflection of achievement. When BzzAgent exited to dunnhumby, we all became ex-employees, and when Smarterer was acquired by Pluralsight, we all were given sweet-ass alumni pins. Ex-employees darn proud of our accomplishments.

But successful exits were not really what Howard was referring to.

During Howard’s tenure it was established that we would refrain from announcing employee departures. The organizational psychology would reflect that it’s a natural part of growing an startup; people come and people go, and addressing each and every individual who is departing serves little purpose. How do you navigate messaging when there’s a conflict? Should one employee get a fully embellished love note, and another a lesser acknowledgement? Do you say something before they’ve departed or wait until their slack is quietly deactivated?

On Friday last week Drake and Omkar officially moved on from Flipside. Both will be sorely missed. Drake asked in advance if he could pen a note to the company in core [internal slack channel], and offered to send it to me to review. Freedom of speech and all that, who am I to say yes or no? In the meantime, we called out both in our Wednesday all hands. Contributions. Excellence. Cultural centers. I gushed, I told stories, I reflected my joy in their future journeys and deep inside felt the bittersweet tug of somehow being left behind. Drake seemed content with that as an acknowledgement of departure, and he never sent me a note (what do you think it would have said?).

But also last week, we parted ways with two other Flipside peers. Evan on Tuesday, and then Madison on Friday. Evan lives in the orbit of humans you’d most like to have a beer with; of ever-present optimism; of wanting to sail all boats to victory. Madison, oh Madison. She’d have you laughing so hard you’d have to take a knee; her very spirit was creative; and when inspired she could design like the wind. Nothing was said publicly about their departures. We informed team members who worked closely them, made sure they understood new working processes, and left it to the grapevine and the element of surprise for others to learn the news as the daily grind continued.

There’s a canary in our talent coal mine: after nearly two quarters without recruiting talent, we’ve recently made 7 new hires and have 6 more open roles to fill. The crypto market is hot. And Flipside isn’t the only company that’s going looking for talent. That’s the bird that’s chirping in our ears.

Dave Balter via Midjourney

And while we know this year will be full of many new arrivals, you can be sure there will be additional departures. Why? Some won’t be interested in the scale part of the journey; others will get recruited by some other fancy-dancy startup, or will seek a change of scenery, the space to meditate or take up surfing; and, yeah, for some, it’s just not a fit anymore — they may just be a better match for some other organization at a different stage doing a different thing.

We may not put it in print, we may not announce all the changes, but that doesn’t mean we’ve lost any appreciation for the work that’s been produced. We can say it out loud. It’s ok. They’ll all be ex-employees someday.

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