To Be And To Last #25

This week we explore the future (as seen from 2015), the $10M lawsuit that saved privacy (or destroyed freedom of speech?), and why we need better businesses (but not more).

Peter Thiel on the future

Tyler Cowen is the Robert Caro of podcasts: just as Caro once moved to Texas just to study his subject’s childhood, Cowen prepares meticulously for guests, resulting in wide-ranging conversations that are refreshingly challenging and educational.

I’ve been enjoying Cowen’s 2015 conversation with Peter Thiel, exploring everything from innovation stagnation to the possible decline of globalization:

“[I]f you want a long/short blue state trade, you want to be long California, short New York. The long/short red state trade, by the way, is you want to be long Texas, short Virginia. […] I would bet on globalization slowly being in abeyance.” - Peter Thiel, 2015

How will you prepare for the future?

The language around long/short reminds me of Annie Duke’s excellent book Thinking in Bets, which has impacted my thinking over the last year particularly. Short of literally knowing the winning lottery number, magically knowing the future does very little good unless you can act on it.

And since we never can know the future with absolute certainty, we would be wise to act in a way that exposes us to asymmetrical upside (where the upside is unlimited(-ish), while the downside is capped).

Will the future be better?

We live in an interesting time, where the last 200-300 years have seen relatively meaningful progress in human existence. That’s actually anomalous in the broader scope of recorded history. And yet it’s a collective bias towards future optimism that’s pretty hard to shake (even in the face of existential threats like the climate).

The solution is broadly that the future depends to some degree on the choices we make both collectively and individually, which is what Peter Thiel aimed to encourage in his fantastic book Zero to One. I enjoyed that book years ago, but I also appreciated Thiel’s thinking on when to consider starting a business:

“My view is we should be starting more good businesses and fewer bad ones.” - Peter Thiel

The number of bad businesses (both financial and/or social responsibility failures) are astoundingly many, while the number of good businesses are few. My personal theory is that the world needs more brilliant minds who are willing to contribute to an existing vision, rather than charging off to satisfy their ego by tilting at windmills with a monogramed and VC-funded lance.

The other side of Peter Thiel

Of course what’s equally fascinating in the Cowen/Thiel conversation is what’s not covered: the lawsuit Thiel was secretly financing to bankrupt Gawker Media. As they talked 2015, Thiel was nearly a decade into a covert mission to right a 2007 wrong, when Gawker Media outed him as gay.

In 2016, one of many lawsuits Thiel financed against Gawker ended in a $140M judgement, resulting in Gawker’s bankruptcy. Was it a victory for individual privacy? A blow to freedom of speech? Ryan Holiday’s book Conspiracy explores some of these implications, while unveiling the brilliant moves Thiel employed to make history. And he nearly got away undiscovered.

How to change people

On a slightly tangential note, I was struck by this simple tweet. We live in a world where people are essential to nearly all progress, and despite advances in AI this will very likely remain true for at least a few hundred more years (likely far longer).

Leading humans is only possible after we realize that controlling them is futile.


To Be And To Last: Thinker Nate Desmond’s weekly roundup of long reads, contrarian thoughts, and hidden jewels that aren’t getting enough attention.

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