"Strong opinions, weakly held" (Ricky Weekly #12)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

I was in Hayes Valley so I went to check out the new basketball court that Kevin Durant and Joe Gebbia (of AirBnB) renovated to the tune of $99,500. There are plenty of terrible courts in SF. I don’t think basketball courts need fancy art—they just need to be leveled and have no cracks. However, it seems like SF is particularly bad at pavement because we also can’t get leveled, crack-free sidewalks, roads and highways. Apparently Oakland is terrible too because Steph Curry had to do the same thing at Concordia Park.

Growing up I spent a gargantuan amount of time on the basketball court. It’s where I went to escape whenever shit happened. It’s one of the cheapest sports to play and cities really ought to keep the courts in good shape.

Thing on my mind:

It’s a cliche in Silicon Valley to have “strong opinions, weakly held.” A friend mentioned that her boss is really good at it because he’d pound the table all the time to get his way, but when given the right information, he’d also 180 and pound the table the other way. To an observer that feels erratic because he’d swing from one side to the other with the same enthusiasm as if nothing happened, but it’s actually quite effective.

To get better at this, it seems like you’d need to 1) know to pound the table and 2) be willing to change your mind completely.

What stops you from pounding the table?

  • afraid to be wrong / ego

  • don’t have a strong opinion

  • prefer consensus-building and other perspectives

  • don’t recognize that pounding the table is often the dominant strategy to get meaningful movement in order to gather more information

What stops you from changing your mind and 180?

  • afraid to be wrong / ego

  • don’t have the discipline to update your past decisions with new information

  • don’t know what info should change your mind

Six months ago I tried on a new way of planning my life to help me operate in a more strategic manner that’s closer to “pounding the table” yet have enough flexibility to “change my mind” completely. It’s a work-in-progress but if you’re interested, it’s called Antifragile Planning by Taylor Pearson.

Related. My friend Tom Currier mentioned on Facebook that a “time-boxed periods of suspended disbelief (intentional naivety) followed by a brief period of intense reflection/analysis” is advantageous. This essay by Nate Soares called “Deliberate Once” also describes this method of operating really well. They’re all different ways of saying the same thing.

Operating this way can make people feel uncomfortable because it feels too rational. The people I find who are the best at this tend to be slightly sociopathic. I think sociopaths are fascinating because unlike the rest of us, they don’t care about the rules or what you think, so their range of motion is much wider. I enjoy watching these people. There are a lot of successful people who sound like sociopaths, and I wonder if it could actually be a dominant strategy today. Nadia Eghbal makes an interesting case in “Shamelessness as a strategy” that it could be:

One explanation might be that it’s an expected effect of the blurring of social boundaries today. In the past, if the size of your community was finitely bounded (like a village, or an aristocratic social class), people didn’t enter or exit these communities as frequently. Under these conditions, sanctions are probably still effective, because members of the community want to be liked and accepted.

But the borders to online communities are much more fluid - perhaps even nonexistent. Under open borders, sanctions will backfire, because they just serve as a signaling boost for the transgressor, attracting outsiders who resonate with that person’s message. What’s meant to be punishment instead becomes a flare shot straight into the night sky.

Piece of content I recommend:

“Dissect” podcast from Spotify Studios.

I listened to Season 3 a few months ago because I’m a huge fan of Frank Ocean and Season 3 was all about Frank Ocean. I just listened to Season 2 this week about Kanye West and omg it’s even better than Season 3.

Note: this is one of the few podcasts that you should listen to on 1x (normal) speed because it’s music. Don’t ruin it.

Your answers from last week:

Last week I asked:

Excelling at knowledge work also requires deliberate practice, but it’s hard to think about how to deliberately practice knowledge work. Tyler Cowen wrote about how he practices what he does. I think writing this newsletter is practice, so is all my public writing. What do YOU do to deliberate practice intellectually?

Your responses:

Whenever I play a sport (ultimate frisbee, basketball, pickleball...), I think of one aspect that I want to focus on improving and write down a way to "practice" it on the field. During and after the game, I reflect on it. After the game, I grade myself on how well I practiced that particular aspect and how I can improve it.

I started codewars with [redacted] and [redacted]. I never used to liked studying algorithms, since I use them so rarely. Now, I think that can help me hit high notes when I need to. So that’s something I picked up on to deliberately practice.

The way I usually think about learning something new is I keep reading / talking to people about a subject until I feel like I’m not learning much that’s new. That’s the litmus test I use for fully understanding something. For example, when I was leaving [redacted], I talked to 20 founders, people who replaced founders, and board chairs who oversaw founder transitions - non profit and for profit in various types of companies - whichever is what it took for me to feel like I understood how to do a transition successfully. That investment of time helped immensely.

Just came back from vegas and I would recommend texas-hold-em. It's a deep game and you practice more EQ than IQ. Try to consistently win/break even at 3/5 while playing low variance rather than GTO. Probably the best thing is how humbling it is, and also, as you get better, you realize it's less about luck and more like a trainable skill. Another thing for knowledge workers I found is to just be as relaxed and stress-free as possible. I find that my brain just soaks up every little detail in life and considers them in weird ways when I'm free. Or it might just be the coffee.

One last thing:

Sorry this newsletter got long. Ugh, so many thoughts.

I’m organizing a party in SF for everyone looking for co-founders to start a company with. I’ve been organizing smaller dinners but I’ve secured a venue for a bigger event now that I have a roster of 80 people. It’s going to be on Sep 5. If you know anyone in the bay who’d be a fit for the event, have them fill out this form and I’ll send them an invite. Fun times!

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called “I got next!” — a personal #RequestForStartups.