Upon Consideration...

Wil A.

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BUSINESS
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Upon Consideration is an audio project focused on alignment, clarity and deliberate decision-making, exploring how alignment breaks down, how clarity is lost under pressure and how better decisions are formed when urgency is resisted. wiljr.substack.com

FEB 25

039: Walking through a Snowy Central Park.

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 Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. https://uponconsideration.com/#listener-response 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 Follow Upon Consideration * Podcast: https://uponconsideration.com/ * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener * Alex: https://hialex.cc Photos! More photos! Video! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

25 min
FEB 18

038: Let’s take some POV photos of a partially frozen Hudson River.

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: Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. https://uponconsideration.com/#listener-response 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 Follow Upon Consideration * Podcast: https://uponconsideration.com/ * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

1h 3m
FEB 9

037: Let's go for a walk and take some photos.

Episode description I went for a walk around Central Park with my camera in -14° weather. There’s a video, too: Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. https://uponconsideration.com/#listener-response 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 Follow Upon Consideration * Podcast: https://uponconsideration.com/ * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener Some photos Visit all photos at www.wiljr.photos. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

33 min
FEB 4

036: The silence before the shift

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 Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. Listener response: https://uponconsideration.com/#listener-response 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 Follow Upon Consideration * Podcast: https://uponconsideration.com/ * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

3 min
FEB 2

035: Whatever happened to jogo bonito?

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 Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. Listener response: https://uponconsideration.com/#listener-response 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 * Follow: https://uponconsideration.com/ * https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#listener-support This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

4 min
JAN 15

034: Is Apple scared of OpenAI?

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 If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. Listener response: https://uponconsideration.com/#listener-response 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 More Upon Consideration * Podcast: https://uponconsideration.com/#follow * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener * Partner: https://uponconsideration.com/#brand-partnerships This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

8 min
JAN 13

033: History on a Horse: Venezuela, Power and New York City.

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. Listener response If this episode made you notice something you hadn’t before, you can leave a short voice message or text. Messages may be referenced anonymously unless you say otherwise. All are read or listened to. Listener response: https://uponconsideration.com/#listener-response 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 Follow Upon Consideration * Podcast: https://uponconsideration.com/#follow * Newsletter: https://uponconsideration.com/ * Author: https://uponconsideration.com/#more * Support: https://uponconsideration.com/#support-listener Photos This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

10 min
JAN 8

032: A missed moment.

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. Call me? * Send me a voice mail or text about this episode! * tel:+13476945202 * More info here: https://uponconsideration.com/#listener-response Psst: By leaving a message, you’re giving permission for excerpts to be referenced anonymously unless you explicitly say otherwise. Not every message is shared. All messages are read or listened to. Links: * Recent weekly email: https://mailchi.mp/uponconsideration.com/2025-12-31-wednesdays * From listeners like you: https://uponconsideration.com/#listener-response * Support Upon Consideration: https://uponconsideration.com/#support-listener * Get Upon Consideration: https://uponconsideration.com Thank you! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit wiljr.substack.com

15 min

Upon Consideration is an audio project focused on alignment, clarity and deliberate decision-making, exploring how alignment breaks down, how clarity is lost under pressure and how better decisions are formed when urgency is resisted. wiljr.substack.com

Creator

Wil A.
Years Active

2025 - 2026
Episodes

39
Rating

Clean
Copyright

© Wil A.
Show Website

Upon Consideration...