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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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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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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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”.

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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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Episode title: 031: We were in Brooklyn with Maduro.

Notes:

* Talking politics

* We were in Brooklyn when Maduro was being flow in (A post-episode realization)

* Change is coming for us all

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Podcast title: Upon Consideration

Episode title: 030: “This is intentionally boring.”

Notes:

* End of year banger

* A five-mile walk, across Central Park and back, in the frigid cold

* New lens on the film camera!

* What’s changing at Upon Consideration

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Episode title: Not quite graupel.

Episode summary

It’s a little cold and a little rainy. Not quite graupel. In this episode, I walk around a very busy and noisy New York City talking about some behind the scenes planning for this podcast, my agency and the new year in addition to how aligning your teams create a better foundation for strategy and success.

Links to stuff in this episode

* The guy walking around NYC with a camera: https://www.youtube.com/@WalkingCommuter

* My agency: https://thenewcommunicate.com

* This podcast overview page: https://uponconsideration.com/#podcast

Subscribe

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About this podcast

Upon Consideration… is a project about intentional alignment, deliberate thinking, focused productivity and better decisions.

It began as a set of personal letters, and became a study of how leaders and creators can work deliberately, even when the world demands chaos.

I write, record and publish to connect ideas, people and outcomes. Join a growing group of professionals and leaders slowing down to think more clearly.

About the author

We moved often while growing up, and every new town taught me to quietly pay close attention. To listen first, read the room and align signal from noise.

That skill–separating and aligning the real from the rehearsed–became the through line of my career (and my life).

Learn more: https://uponconsideration.com/#more

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