The Storyer of Smarterer (Part VI)
On realizing the question being asked is the pothole you should avoid stepping in
"Cancel your vacation, you're not going anywhere."
So recommended Shikhar Ghosh, Flipside Advisor, Professor at Harvard Business School, kind gentleman, and four-star decorated general in the Order of the Strategic Knighthood.
(there is no such Knighthood that I know of. But if there were, Shikhar would likely be top 1% - although you wouldn't know it due to extra honors in humility.)

Eventually, painfully, after many weeks of attempts, Aaron Skonnard, CEO at Pluralsight, said he'd be happy to see a demo of our product.
His sense of time and urgency wasn't ours, or something to that effect.
Two weeks later, Pluralsight's CFO Greg Woodward, and Aaron took me to lunch in Harvard Square. We spoke about Smarterer's technology and about Pluralsight's vision.
As our mains were served, Woodward leaned in, casually and comfortably, "would you ever consider an acquisition."
Well, hey, here we go, game on. I'd practiced this only a few thousand times: I carefully laid my spoon down on the table.
I paused, and raised one eyebrow, appearing surprised and curious, and as innocent as a baby lamb. "Well," I stammered, "to be honest, I'd never considered that."
Their suggestion came with a challenge: prove to us why we couldn't build Smarterer's technology ourselves. This, a good question - arguably the correct one - and one that would require us to tap into Shikhar Ghosh-level of strategic brilliance.
Part of the answer lay with psychometricians.
What the hell is that, you ask?
Well, you remember taking the SATs, right? You can thank these folks, typically PHD-level Quantitative Psychologists whose careers were built around validating the difficulty level of test questions not to mention their reliability and fairness.
To prove our point, MikePK had been hosting a series of focus groups with several psychometricans.
He would begin by scratching at the whiteboard, outlining his thesis of using a two-sided ELO chess * bayesian algorithm innovation: Smarterer’s skill tests measured a user’s ability based on their answers, while simultaneously refining how difficult each question was.
The psychometricians would begin stone-faced, unimpressed. In fifteen minutes they'd be curious; then excited by thirty. An hour in and it was as if they'd puffed DMT and were seeing Japanese katakana and geometric patterns.
"Holy shît do you have a patent on this?" they'd mumble, quietly to themselves.
And the cherry on top: Larry Israelite.

Larry happened to be the father of a close friend. More importantly, he was the head of Learning and Development at Liberty Mutual. Well, that is until Sarah Hodges organized a lurk-and-strike; he began as an advisor, then she offered him a role as our VP of Assessment Solutions.
We had the tech. We had the credibility. And so we dry-ran the presentation for Shikhar just hours before Sarah and I hit the road for five days in Montreal. He asked a few clarifying questions while we waited for his verdict - the way contestants do after serving a Steak Flambé on Top Chef.
"I see it differently," he offered, a most Shikhar opening.

"Anyone can build anything. You or I could build Google Search - save for the fact Google has already figured out the 10,000 potholes we'd step in while trying to make it work right."
He suggested a different approach. “Pick five complicated challenges you had to overcome to make the Smarterer tests work. Five potholes you stepped in that took time and money - and explain how you solved them.”
It was genius: impress and neutralize. They didn’t have the time or expertise to discover all the remaining potholes.
And so that's exactly what we did.
We hunkered down, started over, and redid the presentation front to back, top to bottom and sideways.

I'd be lying if I said I remember the pitch. It's just a blank space; a memory shoved into the inky darkness that lurks behind my eyeballs.
Maybe it was good. Maybe it was great?
I suppose it had to be something because before long, Pluralsight would come forward with an offer to acquire Smarterer.