Freaky Tales: The Wisdom In Extremes - New Click Beta

When Dave Nadig suggested that kicking Russia out of SWIFT might be the moment we can't go back from… I had a “what are we doing here” moment. I had a, “is this the kind of conversation that should stay behind closed doors” moment. I had a, “wait, this feels exactly like the kind of talk we should be having more often, especially with friends like this who'll laugh when I make a Too Short reference, so what am I worried about” moment.

Last Friday afternoon, after a long week of hard conversations with the state of the world being whatever the state of the world currently is (and no, I don’t know or pretend to know what it exactly is, I just know it’s making my work-life way imbalanced right now), it’s good to confide in some friends. It’s good to trade some working theories on how the world might brilliantly succeed or spectacularly implode.

In this case, we recorded it. Dave Nadig, Jason Buck, and I would do this anyway. But, only because Jack Forehand is crazy enough to try anything like this once (or thrice?), and we decided to capture one of these chats monthly, to put it on YouTube, and to call it “Click Beta” - because it’s a funny name for our finance friends.

Like the other episodes we’ve put out so far, we are not setting out to solve any global problems.

We are, however, attempting to share the kinds of conversations we normally have behind closed doors.

We don’t ask, “What do my smart friends think” often enough. Friends is a key word here. People who can laugh with you and at you and you’ll all want to do it again.

Releasing these shows is our version of reminding the world it’s an option. You can make all the fun of us you want in the comments, but you should try it for yourself too. (Tell your friends too, not just the comments section, please.)

This time around, we got deep into the extremely good and extremely bad of AI, trade policies, and legacy. What emerged was a reminder of why these "tail conversations" matter. At lots of levels .

As I kicked us off, "We're talking about tails today, things that can go wonderfully right and disastrously wrong." In a world of uncertainty, mapping these outer boundaries helps us navigate the messy middle where most of life happens.

This is not a practice for the game of live consulting relationships.

It is a practice for brainstorming with friends - where your relationship is a sort of safety net.

It is, most definitely, a type of practice to be on the spot with your thoughts (and takes) like this, where you can decide, as a listener, what’s funny and what’s for-reals.

Dave took us into what he sees as AI's right-tail (positive) potential: "I think there are a couple of right tail things that could be incredibly powerful... we could have a genuinely exciting AI breakthrough that has real impact."

Jason countered with how technology might bring us back to what matters: "Maybe it just comes back to all these ideas of finding your tribe... maybe in real life becomes much more valuable than we could ever even imagine it could be."

When we ventured into left-tail (negative) territory, the conversation got real. Dave worried about institutional decay and weaponized payment systems. I wondered if America was becoming "the coolest bully in school until we bullied all the kids, so then there's nobody left” (re: what happens to the high school bully after graduation?).

But again, even if you think our takes suck as bad as we do afterwards (the group chat has as much self doubt as you’d expect) here's what made it work, for us, if nothing else – we laughed through it all.

We called each other "Gaussians" (normal distribution believers) versus "Taleb guys" (believers in fat tails). We made Rocky Horror jokes ("Dammit, Janet!") and Too Short "Freaky Tales" references. We traded barbs about who's watching Fox News and who's glued to Zillow looking at DC real estate.

Madness, madness, they call it madness.

The laughter isn’t just comic relief. It’s connective tissue. Its rising above me saying, “you must imagine Sisyphus happy” and Jason saying, "I think about how we all kind of think about life, and I'm like, why are we setting ourselves up for failure with this one? But it's good to try to like steel-man the other side."

I can’t promise your smart friends will make you smarter about some real-world stuff.

No, actually - I can promise your smart friends will you make you smarter about some real-life stuff.

Sometimes I wonder if our greatest problem isn't the lack of solutions, but the absence of spaces where we can voice our extreme hopes and fears for ourselves and the world without judgment. The tension between optimism and pessimism creates a middle path toward wisdom. So f***ing gaussian of me, I know.

Do me a favor. Gather some friends, crack a beverage, and let your freaky tales fly. Speculate wildly. Speculate recklessly. Talk about what could go wonderfully right and disastrously wrong. Just, and please don’t skip this step, remember to laugh about it. Have some fun.

Because even if we can't control the future, we can control how we face it, together.

We're doing these monthly on Excess Returns. Check out our latest Click Beta #3 wherever you get your podcasts. And if you want more, Dave already beat me to a write-up, plus he's created a perfect playlist to accompany it (your friends should do stuff that stirs a deep envy inside of you…this playlist is a little too good Dave!):