A lady never kisses and tells.

But then again (at least the last time I checked), I’m no lady.

So how about I let you in on a little smoochy smoochy.

To whet the proverbial whistle, let’s sashay over to the math of BzzAgent. In 2005 we raised $13.8M in venture capital and sold for $60M five years later. Valuations matter, which is why our venture partners only got their money back - while employees and earlier angel investors hit the proverbial financial homerun.

_{(for avoidance of doubt: I didn’t personally make that $60M. I was a piece of the puzzle, not the whole jigsaw)}

BzzAgent's return came with a kink or two, namely in the form of an 'earnout': In order to receive the sale proceeds, I had to stay employed for four years and the company had to hit certain business targets.

“Earnouts: rarely earned, always paid,” is a banker's adage, referencing the battles that often come with them. And true to fashion, after slight disagreements on direction, we honey badgered our way to a new deal within a year and got paid in full. Unpleasant, but necessary.

Which is all to say that when Pluralsight sidled up to smooch Smarterer in 2014, the mists of hard-earned lessons settled neatly into the sidecar.

“You’re going to have to blow my hair back,” was my response to Skonnard’s offer of a cool $35M for Smarterer.

You should know, the fact that I wore my hair in a relatively shaggy mullet-helmet blend had little do with it.

Mostly it was emotional logic - or vanity - depending on your recollection of my past motivations. Smarterer had raised just $4M, and while the return would have been impressive, I'd already made up my mind: I knew this exit had to clear the shadow of the last.

And so we made a date for a few weeks later, to meet up on the 37th floor of the W.R. Grace Building at 1114 Avenue of the Americas in New York City.

There Skonnard, Woodward and I would turn our threesome into a cuckold of sorts - with the addition of Insight Partners' Ryan Hinkle, who sat on Pluralsight's Board.

As luck would have it, I'd already been gussying up to Hinkle; I'd pitched him on investing in BzzAgent (he passed) and later asked him to invest in early rounds of Smarterer (he's hard to get; he passed again).

But love is like a river, snaking its way into whatever bend it can find.

And in this case, that love came in the form of the Smarterer tests themselves: In Excel, Hinkle ranked an impressive #3 out of 100,000 test takers.

Flattery will get you everywhere and here it rained down like the sin of vanity under the shower of a compliment.

Hinkle was thus feeling all sorts of special, and the four of us made small talk, batted our eyelashes, and coo'd warmly about our potential marriage.

Eventually (as if removing a garter on a wedding night), Hinkle delivered their pre-meditated ask: “Would you accept $75M?”

My hair was sufficiently blown back, indeed.

Usually the sordid details of what happens behind closed doors should remain unsaid. However, as we're operating under the guise of an 8th grade sex education class here, allow me to explain:

Pluralsight was a gentle lover who didn't believe in earnouts. Instead they appeared to believe in mutual satisfaction. Which meant the $75M payment wasn't held to any future requirement; most of it would be paid upon the signature of the agreement.

Unsure whether our transaction with Pluralsight would consummate, Smarterer was still actively dating, in the form of a capital raise.

And so Pluralsight - ever the permissive suitor - got down on one knee and proposed a $4M investment immediately, to ensure we paused all other relationships, and mostly to satisfy our fears and desires.

And a final important note: Pluralsight was on a path to go public, and so wouldn't-you-like-to-take-our-stock-pretty-please? After much debate, we chose a balanced approach: $55M in cash and $20M in stock.

_{(again, for furtherance of avoidance of any accounting errors, everyone got in on the action: Payouts went to all shareholders, venture capitalists and employees alike).}

And so betrothed and bearing the glow of our future together, I showed up to my very first Pluralsight Board Meeting as an Observer.

Hinkle, without so much as a wink, and as if clarifying the terms of a prenup never signed, kicked off with some financial matters.

"Well," he paused, flipping through the board deck, "great news. We had $100M projected for the Smarterer acquisition, so at just $75M we saved ourselves $25M for other matters."

And just like that, my hair - which I’d believed to be perfectly coiffed, moussed, and thoroughly blown back - went limper than, well, than overcooked noodles dangling off a towel rack.