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Double or nothing?

Fully Charged
Bloomberg

Hi all, it's Eric. Half a decade ago, people watching Silicon Valley obsessed over whether technology companies were overvalued and out of control. Instead of Facebook Inc. political ads and monopoly power, we were worried about how many unicorns it took to make a bubble. If there was a startup bubble, it'd only be a matter of time before investors came to their senses and valuations plummeted. 

Fortune's Adam Lashinsky wrote in May 2014, "Yes, we're in a tech bubble. Here's how I know it," and then continued to make the case the following year. Nick Bilton worried in Vanity Fair that the industry might go "Kaboom!"

For my part, I wrote about "The Fuzzy, Insane Math That's Creating So Many Billion-Dollar Tech Companies." I reasoned that Snapchat "at a $15 billion valuation, probably isn't actually worth more than Clorox or Campbell Soup." I still agree with the underlying logic of the piece, that private valuations are based on optimistic growth projections, and are inflated by other investor-friendly terms. Caveats aside, at a public market-validated $24.3 billion, Snap Inc. is indeed worth more than either old-guard company.

That 2015 bubble mania is on my mind because the bill just came due on a bet that Y Combinator chairman Sam Altman made in March 2015. At the time, Altman was convinced that the talk about the tech bubble had it all wrong. He wrote that six companies—Uber Technologies Inc., Palantir Technologies Inc., Airbnb Inc., Dropbox Inc., Pinterest Inc. and Space Exploration Technologies Corp.—would be worth more than $200 billion together by Jan. 1, 2020.

They underperformed his prediction by $30 to $40 billion. That's a pretty substantial sum. (There were some other aspects of the bet, which you can read about here.) 

So Altman lost his anti-bubble bet, whose stakes were a $100,000 charitable donation of his opponent's choosing. But Altman's not exactly admitting defeat on the underlying question. "I feel like I won in spirit and made the point I wanted to make, but obviously I lost literally," he said in a text. 

Amusingly, the man who won the bet—serial entrepreneur Michael de la Maza—agrees with Altman that there wasn't a bubble in 2015. He's clearly smarting that somehow even though he won, Altman is taking a sort of victory lap.

"There was not a bubble. That was not primarily what I was betting on," de la Maza told me Thursday. He argues that Altman's overly optimistic claims about startup growth ended up misleading employees who joined startups, counting on overly lofty returns.

As a 2015 bubble Cassandra, I'd point to one short-coming of the bet: In my mind, the debate over private tech valuations remains unsettled so long as the companies in question remain private. That still applies to prominent tech startups like SpaceX, Palantir, Stripe Inc., Coinbase Inc. and GitLab Inc. Uber, Dropbox and Pinterest, which have gone public, all trade below their highest private valuations today. 

On the other hand, I concede that the tech press generally underestimates the extent to which it only takes a few winners to power the venture capital asset class. Even if some billion-dollar unicorns fail, that doesn't mean there was a bubble. 

Looking back, I think it's fair to say there wasn't a bubble in 2015. After all, nothing popped. 

But many of those valuations still do look crazy in hindsight. Some of the startups have fallen from grace. Others tapped big checks from SoftBank Group Corp. to delay any reckonings. Interest rates are still low and there's still plenty of money chasing growth. 

The result is that companies have been allowed to operate unprofitably for much longer than I expected. Food delivery with its negative margins seemed like a losing battle five years ago. Today, those same companies burn cash on a far larger scale. DoorDash Inc. projected losses of $450 million in 2019. 

So I'm not conceding just yet. And Altman isn't exactly rushing to go double or nothing. I asked him Thursday if he thought the valuations of the companies he bet on five years ago would hold up. "I don't know," he admitted. —Eric Newcomer

If you read one thing

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