Feb 5, 2015 · 5 minutes

As a business journalist, I'm normally shy about writing about my personal life but I'd like to share a story about my Dad. In the early 2000s, he was diagnosed with Parkinson's. Anyone who has had a loved one suffer from a neurodegenerative disorder knows what followed was as sad and brutal as it was irreversible.

But as with any hardship there are also the positive moments that emerge, like the time my dad took up Wii bowling. Nobody ever knew how he did it, but he managed to become a master of the game in his 80s. Aside from the clunky, black Atari console he bought in the late 1970s, he shied away from video games his whole life. So it was mysterious how he found this singularity-like oneness with the Wii, as if he saw the stiffness of his arms as a way of hacking the device into victory after victory. He kicked any and all asses who challenged him.

Being a Wii champion is an emaciated, even worthless skill, like winning a hot-dog eating contest. So Dad's Wii bowling prowess says nothing about the man he became in the world, the father he was to us. But it's emblematic of the way he handled his affliction, the way he refused to go gently into that good night, his lifelong gentle demeanor notwithstanding. And now you may be wondering what this memory of Dad playing Wii bowling has to do with anything related to the business of tech. It's a good question.

Yesterday, Chris Sacca, an investor with a track record I'd be foolish to bet against, wrote a post about how his own father had his ass kicked at Wii tennis by Uber CEO Travis Kalanick. It was ostensibly a piece about how Larry Page had his work cut out for him going up against “TK”, as Sacca calls him; and you may have, like me, clicked on it because Sacca is smart as hell and you were hoping to find an insider's insight into the respective competitive edges both companies hold against each other.

Instead we got the kind of endless anecdote you sometimes find yourself grinning emptily into at dinner parties. As Sacca tells it, some rube from Truckee challenges to Wii tennis the man “tied for 2nd in the world” “on the Wii Tennis global leaderboard” (yes, such a thing apparently existed). And the guest, rather than mentioning this otherwise dubious factoid beforehand, discloses it only after his Wii tennis shoe is impressing its treadmarks onto the throat of his challenger. That is to say, his host. In his own home. Which, I guess I'm just old, but I always thought you were supposed to treat your host with respect.

For Sacca, this seems to be the occasion for some Oedipal glee. “He might have even been sweating a bit,” Sacca says about his father. We writers know these rhetorical tricks: Not “I saw my father sweating,” but rather, he might have been sweating because it probably didn't happen but it makes for a better story if he did.

This is depressing but informative: The question for anyone hosting - or financially backing - TK now becomes: If TK can hold pertinent information back from your father while you're sitting there watching, could he do the same to you? What if it's all a game to TK?

This is the thing that keeps bugging me about Uber, and its CEO TK. Sacca describes him as “eerily brilliant” and I do not at all doubt the brilliant part. It's the eeriness that no Uber investor wants to confront - the ungainly part of the bargain. And how do investors in Uber quantify - let alone put a market value on - the eerie?

The easy answer is you simply pretend there's nothing eerie here. And I wouldn't even have paid much notice to Sacca's post except it's part of a weird trend among Uber investors, people I normally respect. It used to be that if you were an investor in a company your opinion was automatically suspect. That changed about a decade ago as VCs like Fred Wilson, Bill Gurley and David Hornik began writing about the companies they invested in in a way that was anti-PR - here's why I'm betting my future on this startup - so that investing became an opportunity for insight.

Somehow Uber has reversed that.

Before I go on, some disclosure here. I've written for Pando for a couple of years while contributing to other sites as well. I'm lucky as a writer because all of the places I write give me the freedom to say exactly what I think. If they don't I'll walk. I've held off writing about Uber on any of them because, frankly, there was something about the company that just didn't quite add up. Its success, growth and change in our everyday lives was evident but somehow the company's valuation in private markets didn't make sense. I began to think there was a greater-fool game going on in its private funding.

When the whole spying scandal erupted, I of course sided with the journalists. So yes, you can call me on my subjectivity there. But as a journalist accustomed to following publicly traded companies, I half expected the usual narrative to follow: the offenders fired, the company issuing an abject apology that would be forgotten as soon as the stock price began rallying again. Instead, the still-private Uber stood by its tarnished guns, which struck me as, well, eerie.

Worse, the investors in Uber who could have stood up stayed silent. For good financial reason: The company worth $18 billion last June raised $1.8 billion in two rounds in December at a $40 billion valuation. You would think that would be enough to propel Uber toward its dreams, but no. Last month it raised yet another $1.6 billion in convertible debt, which if converted could dilute the investors who defend Uber so passionately.

Which raises two uncomfortable questions: Why is all this capital needed, and where is this money going? Apparent answer: We investors would never bet against the CEO! And yet, if you consider the most respected tech CEOs like Steve Jobs and Jeff Bezos, they aren't just CEOs investors doubted. Their very leadership is defined in their defiance of what investors wanted. On that front, the love Uber investors have for TK is itself a warning sign for the company.

Here's what I'd say to Uber investors: You own part of what is potentially one of the most powerful corporate combustion engines ever devised by mankind. Congratulations! But it's both stable and unstable, and it could end up blasting up into uncharted space or blowing up in your face. And please don't portray your loved ones as losers to puff up the legend of TK. As I have been reminded time and again: thinking about hyping an already overvalued company? Good luck.