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June 2, 2026

Eras of Assistant Part III: Kate

A second departure, the spirits are always right

My EA of nearly two years is leaving.

Well, technically Kate has worked with me for a total of eight years, there just happened to be a four-year break in between.

If that's too much math for you, it is for me, too. We can just leave it at that.

kate cover

The first time Kate left was in 2020. She departed for her own entrepreneurial journey to open a yoga studio, which was about as valid a reason as they come.

Still, after a six-year stint, I was hurt and deflated. I felt abandoned.

Decades before, one of our senior executives, Kevin, seems to have spent $400 at a strip club in Atlanta, on our corporate card no less.

(no no, this is relevant, I swear).

"Oh, sorry," he said, "my mistake, I was just buying drinks for a client and this was the only place around." He apologized and said the cheapest offering they had was this big bottle of champs.

Uh huh, right, good one, Kevin.

Anyway, Kevin promptly paid us back, but later demanded half the company, got huffy, then quit with some customers in tow. My brilliant mentor, Shikhar Ghosh, offered some advice: no matter how frustrated you are, send him a handwritten card of appreciation for his time and wish him luck in his future journey - because people remember times of transition more than anything else.

The point? (seriously, is there one?)

kate gun

No matter how sad I was, I hitched up my trousers to throw Kate a celebratory going away party. It was to be held on March 19th, 2020 to be exact - which is about the time the world went into lockdown due to some weird virus from China. We postponed the party for two weeks, enough time for the world to return to their offices.

Best-laid plans, but the intention remained. Bridges in tact, appreciation flowed, and in mid-2024, after an excellent run at her own adventure, Kate rejoined as the right hand to my brand of corporate chaos. Lucky her.

Yeah, right, ok, so one might ask, why is Kate leaving again?

Valid question.

Well...

<looks in mirror, winks>

...let's start at the obvious: me.

kate death

I don't claim to be busier than the busiest of executives, but offer my own operating system of peculiarities: 'tisms or a bit of Aspergers, and probably some ADHD thrown in to whatever spectrum stew I lean toward. I tend to not shut off, expecting crisp responses and witty repartee in lickety-split fashion at all waking hours, business days be damned.

I'm wildly unpredictable. Kate mirrors without a question.

Then there's the cocktail of personal and business life, blended like overlapping hues in a water color painting. One moment it's organizing an offsite for senior executives and filling my calendar with 1:1s and client meetings, the next ensuring monthly pest spraying is done at this house or that, filling out healthcare forms for my aging mother, or ordering a new license plate to replace the one my lovely wife tore off the BMW by backing out of the garage with the rear hatch still open.

We are never-ending problems. No matter, easy-peasy, Kate will solve them.

kate outdoor

Every startup is full of ups and downs, rowboats with kettle bells for paddles on the high seas. The last year at Flipside has felt like rowing through a 'Noreaster, as we navigated away from crypto into AI. There have been RIFs, executive restructuring, six months of fundraising, product evolutions, selling our core business.

Through all of it, Kate's job wasn't to row. It was to keep the rest of us from mistaking rough seas for catastrophe.

To be honest, if one needed a moment, there was a breakpoint: a straw on the camel's hump, a fly in the EA soup. It seemed simple enough, a two-hopper of flights from Pittsburgh to Salt Lake, which sadly kicked off with delays before most people had morning coffee. Kate navigated flight choices with impossible connections, storm systems, and me wanting double and triple bookings in all directions. Try this, do that, avoid Atlanta!, no bulkhead, window please, can you just tell them to hold the plane - hundreds of messages over five hours as I felt it was my destiny to make it to Utah regardless of clear facts that said otherwise.

A small thing it might seem, but a sharp point on the relentlessness that I live by.
kate note

Feelings are a thing and, yes, contrary to popular belief, I have them - although I find it often a challenge to express them effectively. I'll do my best here. Kate, oh Kate, you are a true talent, skilled at all things detailed, an operator of urgency, a religion to being present, a roller with all of the punches. You smooth rough edges and lead with balanced counsel. You are willing and positive, and deflect my stress and chippiness with bravado. You know when the planets are aligned and when the stars say tread with caution. You have have made me better in more ways than I can count.

And to what's next: I wish you excellence on this next step in your journey, with experiences that inspire, and opportunities for personal growth. You are family. I will miss you dearly, but know you aren't far, spiritually guiding even if you aren't fox-holed in our particular trench every day.

I might leave with an offer of an open door, to second-go arounds that were even better than the first, and to a third, somewhere out there, down the road a way, when the right time is upon us for our future adventure together to take shape.

kate end
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