Backing the Winner

The past several months have seen a turn of the tide. Whereas historically when you think/hear about Silicon Valley, you probably think of a liberal stronghold. I mean, it houses San Francisco, often the poster child for the image of a liberal city (in ways good and bad). But even “Silicon Valley” as a concept has long seemed tilted in a liberal way. Sure, there are plenty of well-known counter-examples, but the reason they’re well known is largely because they’re very clear counter-examples of the “norm”. Most of the employees working at the various tech companies skew liberal as the donations coming out of those companies have made clear over the past many years. That may or may not be changing, my guess would be that it won’t, but what is changing is how vocal the counter-examples are becoming. Yes, the contrarians.

But that’s the thing. As more and more high-profile investors and entrepreneurs come out of the woodwork to vocally support Donald Trump, they’re actually not being contrarian at all. In fact, they’re doing something tried and true in Silicon Valley: backing the winner.

The tide along with the polls have been turning in Trump’s favor for months now. The recent performance in the debate by Joe Biden seemed to embolden a new contingent of folks becoming vocal in opposition to the current President. And the assassination attempt on the former President, just days ago,¹ seemed to kick this all into another gear. In the past, if people in Silicon Valley were supporting Trump, they were doing so quietly. Now, increasingly, they’re doing so loudly. And again, this is hardly surprising as they’re no longer going out on a limb to back a long shot, as Peter Thiel once famously did. They’re now backing the clear favorite. And figuratively voting with their mouths and wallets until they can presumably literally vote.

Obviously, we still have several months until the actual election. And if the past few weeks are any indication a lot can and perhaps will happen between now and then. But the trend is pretty clear here. Trump is gaining momentum and the only natural thing that may stop him right now is the phenomenon of peaking too early. Otherwise, he’ll ride this all back to the White House.

If you think about it from that perspective alone for these new (or newly vocal) supporters, it makes sense. Why would you spend time and money on a lost cause, as it were? This is the equivalent of backing a startup that’s clearly failing when the main competitor is the market winner and is also right there, ready to take your money. And while such money may not yield the same monetary returns as VCs are used to, it may lead to far greater returns depending on how that money is used to buy friends and influence in a future administration.

Beyond Biden’s debate performance and questions of his mental state, there’s also a sense that his administration has been no friend to tech the past few years. This aspect is likely far more nuanced than it may appear on the surface, with a growing schism between “Big Tech” and “little tech”. It sure feels like it was no coincidence that Andreessen Horowitz put out their recent manifesto ahead of announcing an intention to support Trump in the coming election. I suspect many others are going to rally around this notion. Obviously, it’s self-serving as it promotes both startups and newer technology like AI (and yes, in the a16z case in particular, crypto). And it also potentially helps to ensure the Big Tech players have less of a shot to dominate AI as they might if left unchecked (unclear how this plays out at Meta, where Marc Andreessen remains on the board, but with their open-source push, perhaps all circles can still be squared here).

This “single issue” framework also helps to gloss over the how shall we put it — less savory aspects of a would-be second Trump administration. To put it in a less favorable way: the shit Trump fucked up in his first term that he’ll undoubtedly continue to do in his second.

In years past, almost no one in tech would dare be seen siding with Trump because of what his administration wrought. Things like the Supreme Court justices he picked overturning Roe v. Wade. The whole January 6 thing. All the various crimes and misdemeanors just within his administration, if not done by he himself. Etc. But now it feels like there’s quite a bit of air cover to fly right over these issues.²

It sounds insane because it is insane, but we've grown comfortably numb to the chaos that was Trump. So much so that people are now begging for more of it!

Here’s where I betray my own thoughts on the matter, which I’ve not been shy about in the past. But unlike many of these other newly vocal VCs, I could not and would not support Trump because I have both a spine and a soul. As his first administration proved, Trump is who we thought he was, to borrow a phrase from the late Dennis Green. And why do we think a second administration would be any different?

Because J.D. Vance is there? Has the laughing ended yet? I'll wait.

Vance, while seemingly smart in ways that Trump is seemingly not, is still, above all else, an opportunist. He’ll change his stance and tone on any and everything faster than anyone else with a Silicon Valley background as a part of the administration. To his credit, he was early to do it with his stance on Trump himself. But he did it to get elected in Ohio. And it worked. And now that flip-flop has really worked. He’s likely to be a 40-year-old Vice President.

This is all related. This is all opportunists taking advantage of a dire political situation in the US. Some are agenda-driven. Some wish to further their careers. But many think and want to project that they’re being contrarian here, because everyone knows this is how you really “win” in VC. And it worked for Thiel the last go-around.³ But the reality this time is that they’re not. They’re simply backing the winner. Sheep following the flock.

¹ Hopefully it goes without saying that despite my general stance on Trump, this attempt was yet another tragic stain on America.

² I continue to believe that history will not look kindly upon Trump or those that support/enabled him.

³ His own thoughts this time are far more interesting...