hey. it's wil.

Join me on a walk across Central Park from the West Side to the Met (and back again).

In this episode, we explore the ancient Persian city of Nishapur (a hub of the Silk Road), the hidden engineering history of Park Avenue’s most "unstable" skyscraper, and the somber reality of why we must record our thoughts during times of war.

Key moments

* How Central Park hides its traffic via "below-grade" thoroughfares

* The Silk Road: Trade artifacts from the 1930s now at the Met

* The Journaling Pivot: Why our memories of the Iraq and Afghanistan wars are unreliable

* The Citicorp Center: The building that almost toppled in the 1970s

* The "hilly" origins of Manhattan

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In this week's dispatch, we brave the "crunchy snow" and mud of Central Park to uncover the layers of history hidden between 96th and 72nd Streets. Beyond the scenery, we dive into the functional difference between embassies and consulates and take our time at the Alexei Navalny memorial.

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Episode description

Will winter never end? Come walk with me through Central Park after the February blizzard and hear me talk about Alex, a new product I’m launching to help make executive-level decisions before doing dumb-ass things.

Episode references

* Alex (my new product): www.hialex.cc

* Photos from this walk: wiljr.substack.com

* The full walk-and-talk-and-photo-taking video at wiljr.substack.com

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Photos!

More photos!

Video!

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On another cold New York morning, I walk down to the Hudson River, take some photos and talk about artificial intelligence and the collision with humans.

There’s video (see below)!

Video

Episode references

* Alex (my new product): www.hialex.cc

* Photos from this walk: wiljr.substack.com

* The full walk-and-talk-and-photo-taking video at wiljr.substack.com

* Dario from Anthropic: https://www.nytimes.com/2026/02/12/opinion/artificial-intelligence-anthropic-amodei.html

* Nick Thompson:

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Episode description

I went for a walk around Central Park with my camera in -14° weather.

There’s a video, too:

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Some photos

Visit all photos at www.wiljr.photos.

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Episode description

Apple and OpenAI are on a collision course.

References

* Apple AAPL Q1 2026 Earnings Call Transcript: https://www.fool.com/earnings/call-transcripts/2026/01/29/apple-aapl-q1-2026-earnings-call-transcript/

* Apple Financial Results - Q1 2026: https://www.apple.com/investor/earnings-call/

* OpenAI’s “secret” new device is coming. Here’s what we know so far: https://www.axios.com/2026/01/23/openai-device-earbuds-sweetpea-altman

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Episode description

Sepp Blatter. St. Pauli. DFB. Government of France. All are talking about boycotting the 2026 World Cup. And Gianni Infantino? He’s touring and meeting with city mayors to “lock in support”. With a little more than 120 days from the start of the tournament... that can’t be good.

Related links

* “Infantino takes World Cup charm offensive to US mayors”: https://apple.news/AgHMdbgBaTZWfNW3ZVXghGA

* The Beautiful Game: https://en.wikipedia.org/wiki/The_beautiful_game

* Sepp Blatter has something to say: https://apple.news/AKk9RPny5Tv6ZQytQfY-V4g

* St. Pauli has something to say: https://apple.news/APt4Fd3hzSm6mvkqs1NHG_A

* The German Football Federation) has something to say: https://apple.news/AiqsoNMVAS5WPRFpQIxbDeg

* The French Government has nothing to say (yet): https://apple.news/AiqsoNMVAS5WPRFpQIxbDeg

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Messages may be referenced anonymously unless you say otherwise. All are read or listened to.

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

* https://thenewcommunicate.com

Upon Consideration

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Episode description

On a windy New York morning, I walk past one of my favorite locations in New York City (Lincoln Center) towards West End Avenue on my way to run an errand.

After listening to Ben Thompson and John Gruber this week, in addition to reading about the Google / Apple AI partnership, I wonder how afraid Apple is of OpenAI (given what’s not being said about the partnership).

This episode reflects on a single phrase in a quote from the Financial Times via 9to5Mac: ““OpenAI declined to comment. But a person close to the company said it had taken “a conscious decision to not become the custom model provider for Apple” in the autumn of last year and instead focus on building its own AI device to leapfrog the big tech companies.”

It’s this piece of that quote that has me wondering if Apple is scared of OpenAI (and Jony Ive): “instead focus on building its own AI device”.

Listener response

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Episode description

On a cold New York morning, I walk past the Simón Bolívar statue near 59th Street and Sixth Avenue and think about why a 19th-century Venezuelan liberator still feels relevant today.

Bolívar fought foreign rule, resource extraction and the impossible task of unifying competing interests across Latin America—problems that sound uncomfortably familiar in 2026.

From Venezuela, oil and modern regime politics to America’s fixation on strategic resources, and from global power plays to the quieter leadership battles inside cities and businesses, this episode reflects on how history doesn’t repeat—but it definitely rhymes.

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Related work

I share examples of how early misalignment shows up inside organizations. Not at the breaking point. Before momentum makes it expensive.

https://thenewcommunicate.com

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Photos

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Podcast title: Upon Consideration

Episode title: 032: A missed moment.

Thoughts:

Everyone watched the shot. No one noticed the moment the season shifted.

Strong teams rarely fall apart all at once. The shape starts to change long before the headlines do.

On a morning walk through Central Park, I’m thinking about Liverpool, leadership, grief, new systems and the small, easily missed moments that tell you more than the scoreline ever will.

This episode is about the signals most people ignore—the gesture, the frustration, the shift that doesn’t register on a stat sheet but explains everything that follows.

If you’ve ever watched a team, a company or a project still look fine while something underneath felt off, this is for you.

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