We sat by the pool and cried for about twelve hours.

Well, I didn't cry, that's not in my nature.

But Hodges did plenty - after she reminded me just how unfair the choice was she had to make.

Let's square the facts and circle the truths shall we? As the incoming CEO I managed Sarah Hodges and we both were, well, strong of opinion.

In truth, Hodges is more talented than most operators you'll work with in three lifetimes. She both plans and executes. She creates signal from noise and accepts nothing less than exceptional. She can market. She navigates spreadsheets. She builds relationships. She knows when to clown and when to buckle down.

I'm a visionary and she's an operator, which made our work together a magnetic sort of chemistry - marred mostly by our commitments to individual peccadillos. Hodges would build a deck and I would change the fonts and back and forth we'd go.

Sure it sounds silly, but serifs matter to me and Arial Sans to her and a little paper-cut argument would balloon and then, well, then I'd arrive home to find Hodges had moved all of her belongings out of my condo.

I phoned her in the middle of one such spat and directed her to get on a plane the next day, to travel with me to Arizona for the ASU-GSV conference at the luxurious Phoenician Resort in Scottsdale.

"Do your job," I hissed, like a total asshole, as she quietly seethed.

The choice was clear: Hodges and I would stop dating and she would stay on at Smarterer - or we continue our romantic relationship and she would leave the company.

Font choices aside, I selfishly worried about how we'd ever possibly replace Sarah Hodges. She delivered with the strength of one hundred gorillas and one thousand steady-handed surgeons. She was committed to our mission, and yet Smarterer was running short on cash. If she left, it would be nearly impossible to replace the breadth of her skills.

A no-win situation, or a double bind, or catch-22, pick your poison. We chose love: She would leave Smarterer…but with a catch. We agreed on a ninety-day departure window, effectively kicking the can down the road.

You should know, the matriarch of Ed-Tech is absolutely, unequivocally (not-up-for-debate), Deborah Quazzo.

Long before the decision about Hodges' role, Quazzo had glided into our office, elegant, brilliant and shrewd, the crispness of her diligence matched only by the creases in her pressed-to-perfection pantsuit. When we landed her as an investor it was a finger snap of industry credibility.

Part of Quazzo's brilliance was building the ASU-GSV conference, and as one of her portfolio companies, she offered us a coveted invitation in April 2014 alongside fourteen hundred of Ed-Tech's most important executives.

As if pressure-treating wood, I reminded Hodges of the expectations from Quazzo's investment (and the gift of this rare invitation) as we boarded the plane to Arizona. Hodges was cold: she muttered no more than two words to me for the five-hour flight.

At the conference, at an awkwardly too-small hightop in the main ballroom, Corey Greendale, Managing Director at First Analysis, offered an idea. "I think there's someone you should meet," he said tapping out a quick email.

"His name is Aaron Skonnard. He runs an online education startup called Pluralsight - they have money and are looking for acquisitions."

Skonnard and I set some time to talk at the event - but then he backed out, double booked, an immovable conflict, a 'sorry we couldn't make it work' type of thing.

No matter, these things happen, buck up buttercup, as they say. But during my fifteen-minute company pitch presentation - in a room so tiny it felt overflowing at thirty attendees - Skonnard was caught peeping curiously from behind the last row of seats.

At the very end of the conference, Skonnard, Greg Woodward (CFO at Pluralsight), Hodges and I squeezed in a hasty tete-a-tete. It was a hit and run, everyone blurry-eyed from a long conference and late for their respective flights. We opened with our, lapel-grabbing headline - validating anyone's skill in anything in just 10 questions, 120 seconds - and speed-ran through all of the associated technologies.

As we walked away Hodges whispered, "I don't think they liked us very much."

"Oh they did," I said, hopeful, in the way one does when wishing it so.

And then, considering the potential of an acquisition, advised, "Do not tell anyone you're leaving Smarterer yet."

Best laid plans.

Because while I could already hear the Hodges 90-day clock ticking, I was not yet aware that Aaron Skonnard, CEO at Pluralsight, would ghost every attempt I made to reach him.