This episode of the excellent By All Means podcast demanded to be shared for two reasons:

First, Allison Kaplan is painfully good at her job. I say painful because, as a podcast host myself, I know it’s not easy to (a) identify good stories and (b) lead a guest comfortably through an interview. She was incredible as a host in this episode, and anyone looking for tips on how to conduct a long-form interview aught to follow Ali’s work.

Second, the story told in this episode is undeniably compelling. Chris Montana’s story is filled with ups and downs, he’s a guy you just can’t help but want to root for.

I lived a couple miles from Du Nord when it first opened, and my wife and I quickly found it to be our favorite local spot. Even now, I can close my eyes and remember exactly how I felt sipping a gin cocktail in his lounge. I’ve never met Chris before, but after hearing his story in full, I can tell that my experience at Du Nord was carefully considered and designed, and I appreciate it all that much more.

There’s grief and pain tied in with the Du Nord story, to be sure… but also lots of success and optimism for the future. It’s stories like these that we all need to hear, learn from, and share voraciously with others.

I’ve heard many interviews with Angela Ducksworth over the past few years, and I’ve always felt bad after each one.

Grit, as a trait, is something I feel like I possess relatively little of.

Maybe reading this article is just feeding into my own confirmation bias a bit, but the reason I wanted to share it is because it introduced a different measure to me: conscientious.

Conscientiousness is a component of the popular “OCEAN” model of personality, according to which we all have “big five” rather self-explanatory measurable traits: openness (to experience), conscientiousness, extraversion, agreeableness, and neuroticism. This model has left a large mark on personality psychology, in part because it raises useful questions that researchers have subsequently investigated, ranging from the extent to which variation in these traits is caused by nature versus nurture—one 2015 meta-analysis estimated the answer is about 40 percent genetics, 60 percent environment3—to whether and to what extent various traits correlate with success in work, relationships, and other settings.

Again, maybe I’m just hearing what I want to hear, but I’m very interested in learning more about the OCEAN model of personality.

Update: I just spent nearly 90 minutes convincing my kids to each eat half a bowl of Cinnamon Toast Crunch. Maybe I do have some grit after all...

“I think I still feel the same way about it that I did in the very beginning,” Whibley says. “The day that I get sick of playing a song that everyone knows and everyone goes crazy when we play it, and everyone starts jumping around and everyone sings it, I should just quit because I’m so fucking jaded. It’s the greatest feeling in the world. I’ve never understood that. I don’t get Radiohead, even though I love Radiohead, why they don’t play their big songs.”

I respect the hell out of that pull quote, it’s how more of us should feel about things that make other people happy.

It’s hard to express what this song meant to me back in 2001 as an impressionable sixth grader. I’m definitely not an edgy, punk skater kid (nor have I ever been), but this song is still in my regular rotation because it gives me so much life.

I often think about what makes me dislike the “sales” part of being an entrepreneur, and this article outlines exactly why.

The article is a summary of Robert Cialdini’s book “Influence: The Psychology of Persuasion”, and gives six examples of how people can convince you into thinking, acting, and consuming a certain way.

Wisdom isn't found in certainty. Wisdom is knowing that while you might know a lot, there's also a lot you don't know.

Wisdom is trying to find out what is right rather than trying to be right.

Wisdom is realizing when you're wrong, and backing down graciously.

Of all the mysteries and injustices of the McDonald’s ice cream machine, the one that Jeremy O’Sullivan insists you understand first is its secret passcode.

Press the cone icon on the screen of the Taylor C602 digital ice cream machine, he explains, then tap the buttons that show a snowflake and a milkshake to set the digits on the screen to 5, then 2, then 3, then 1. After that precise series of no fewer than 16 button presses, a menu magically unlocks. Only with this cheat code can you access the machine’s vital signs: everything from the viscosity setting for its milk and sugar ingredients to the temperature of the glycol flowing through its heating element to the meanings of its many sphinxlike error messages.

To me, there’s no option but to give the money back. Being a tech worker is not like banking, where you know you’re not doing good for society. A lot of tech workers delude themselves into thinking they’re being “mission oriented.” I was never quite delusional enough to believe that. I was just hoping I didn’t do net harm, which in itself is hard to avoid in this industry. I want to spend and donate as much as I can in my lifetime, and if I’m able to have the money create meaning, that’d be good. I haven’t decided what I’m going to do with it yet, though.

Powering through is often passive.

What you're doing is avoiding the harder thing, which is confronting the uncertainty of change. You're protecting yourself from the fear of regret.

Worse, by continuing to barrel through towards an inevitable dead end, you're cheating yourself out of all the opportunities quitting might bring.

For the families of soldiers missing in action in Vietnam that Boss studied early in her career, or the family members of victims of plane crashes where the bodies aren’t recovered, this type of thinking means thinking: “He is both living and maybe not. She is probably dead but maybe not.”

“If you stay in the rational when nothing else is rational, like right now, then you’ll just stress yourself more,” she says. “What I say with ambiguous loss is the situation is crazy, not the person. The situation is pathological, not the person.”

An analogous approach during the pandemic might be, “This is terrible and many people are dying, and this is also a time for our families to come closer together,” Boss says. On a more personal level, “I’m highly competent, and right now I’m flowing with the tide day-to-day.”

The Wright brothers won every patent case they fought, and it did them absolutely no good. The prospect of a fortune wasn't what motivated them to build an airplane, but ironically enough they could have made a fortune had they just passed on the litigation.

The use of the Wright Brothers’ tale as a pivot into what’s happening in today’s world of software patents is what makes this article a must read.