I went on Jason Calacanis' podcast this week for the fourth time. We've had some explosive, illuminating, and contested conversations over the years, Jason and I. And I've loved everyone of them. Whether we were discussing venture capital, profitable businesses, and the definition of success or talking about big tech, education, healthcare, and wealth taxes. Having intense debates about big questions is a thrill. But this last one was different.
Partly because we simply agreed more than we usually do, but also because the topics felt dangerous this time around. Like I ought to weigh my words carefully, lest I open a flank for later attacks. Like every argument ought to be hidden in an armored helmet from inside a protective trench.
In all my appearances on Jason's show over the past decade, it had never felt like that before. The conversations were always good because they weren't burdened by two tons of offense-deafening hedges. So even though the prudent, protective thoughts were there, I choose to ignore them, and instead have the kind of honest exchange that used to be the norm, but now feels like it might paint a target on your back.
We talked about the Canadian trucker protest, the Danish pandemic response, social media as a weapon of mass dysfunction, our April crisis at Basecamp, and then of course Bitcoin vs authoritarianism. So all the light dinner conversation pieces we could find then...
But for all the pessimism about the state of the world, social media, and our democracies, I actually walked away with a new sliver of optimism. Jason made the excellent point that these types of dangerous conversations that are increasingly leading to dire consequences for those who dare touch them in public aren't actually disappearing. They're moving. That the repressive, partisan nature of Twitter in particular isn't only leading to large amounts of self-censorship (though that too), but also fueling a new interest in private chats.
That's a connection I hadn't really paid much attention to until Jason brought it up. But now I see it everywhere. I'm in a range of private chats now where these types of open debates about dangerous topics are flowing freely. I dive in with those who reply to this newsletter in such conversations all the time as well. I see it with friends and my wife too. Refuge is being sought in privacy.
Might this be the way out of the cesspool that is modern social media? Reasonable people retaining their voice, but using it in more private spaces? One could hope. Ala how Facebook is turning into an old folks home because the next generation wouldn't be caught dead there. Might the next wave be abandoning social media altogether, and finding meaning in smaller groups again?
In the mean time, I'm happy that people like Jason still dare to discuss the difficult in public. Part of the appeal with these debates is to show those who are left shell-shocked and tribe-less from the daily partisan skirmishes that there are more than two ways to think. Then carry on the discussion with their confidants in that private group chat.
Partly because we simply agreed more than we usually do, but also because the topics felt dangerous this time around. Like I ought to weigh my words carefully, lest I open a flank for later attacks. Like every argument ought to be hidden in an armored helmet from inside a protective trench.
In all my appearances on Jason's show over the past decade, it had never felt like that before. The conversations were always good because they weren't burdened by two tons of offense-deafening hedges. So even though the prudent, protective thoughts were there, I choose to ignore them, and instead have the kind of honest exchange that used to be the norm, but now feels like it might paint a target on your back.
We talked about the Canadian trucker protest, the Danish pandemic response, social media as a weapon of mass dysfunction, our April crisis at Basecamp, and then of course Bitcoin vs authoritarianism. So all the light dinner conversation pieces we could find then...
But for all the pessimism about the state of the world, social media, and our democracies, I actually walked away with a new sliver of optimism. Jason made the excellent point that these types of dangerous conversations that are increasingly leading to dire consequences for those who dare touch them in public aren't actually disappearing. They're moving. That the repressive, partisan nature of Twitter in particular isn't only leading to large amounts of self-censorship (though that too), but also fueling a new interest in private chats.
That's a connection I hadn't really paid much attention to until Jason brought it up. But now I see it everywhere. I'm in a range of private chats now where these types of open debates about dangerous topics are flowing freely. I dive in with those who reply to this newsletter in such conversations all the time as well. I see it with friends and my wife too. Refuge is being sought in privacy.
Might this be the way out of the cesspool that is modern social media? Reasonable people retaining their voice, but using it in more private spaces? One could hope. Ala how Facebook is turning into an old folks home because the next generation wouldn't be caught dead there. Might the next wave be abandoning social media altogether, and finding meaning in smaller groups again?
In the mean time, I'm happy that people like Jason still dare to discuss the difficult in public. Part of the appeal with these debates is to show those who are left shell-shocked and tribe-less from the daily partisan skirmishes that there are more than two ways to think. Then carry on the discussion with their confidants in that private group chat.