Hey. It's Wil.

Talking to myself Ever seen the streets before the cameras and talent come out for film day? This morning’s observation What struck me about the recent Meta restructuring wasn’t the technology or even the haphazard way it was rolled out. It was the assumption that removing people automatically makes an organization more efficient. * The work rarely disappears. * More often, the coordination disapp...

Audio only. Highlights from this morning’s walk: * It’s humid out * The lighting was amazing * Is the world moving to the (far) left? * Big rain storm coming * How do I respond to comments? Photos from this walk… 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

Day 2 of testing a live (and recorded) audio format as I walk around New York City in the morning. Photos from today’s walk. 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

I’ve always wanted to create my own radio show. Here’s test one. Test two tomorrow. 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

May 14, 2026 I walk around New York City and Central Park in the morning, taking photos with a newly added 50mm lens. Personal operating systems, expectations, case studies, photos and sports. * Referenced case study: https://thenewcommunicate.com/#alignment-in-practice * Contact me: hello@uponconsideration.com * No guest requests. It’s a solo joint. This is a public episode. If you would like to...

I have a few of these shorts lined up. While these are my first attempts at creating short(er) videos, I'd like to try doing some narrative voiceovers to add a little context to the video. (Maybe, like, read a piece from a book or poem or song?) Note: Initially posted on YouTube: https://www.youtube.com/watch?v=SD_61Isu3Vc . This is a public episode. If you would like to discuss this with other su...

Only 30% of enterprises have fully moved to the cloud, yet we are already sprinting toward AI. The result? A 95% failure rate for AI initiatives. In this episode, I talk about why high-performance teams are failing at the finish line and why “team onboarding” must include a consistent decision-making framework to protect your margins and your sanity. Links: • Ben Evans: www.ben-evans.com • The Gov...

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" t...

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. For video and images, see: https://wiljr.substack.com This is a public episode. If you would like to discuss t...

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.subst...

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.nytim...

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...

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/...

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/AgHMdbg...

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 epis...

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...

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 te...

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 Call me? * Send me a voice mail or text about this episode! * tel:+13476945202 * More info here: https://uponconsideration.com/#listener-response Hey: By leaving a message, you’re giving permission for excerpts...

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 Call me? * tel:+13476945202 * Click/Tap the link above * Send me a voice mail or text! * More info here Note: By leaving a message, you’re giving...

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 w...

Episode title: Wait, that’s not a dog. Episode summary It’s the weekend! With my digital camera in hand, I’m walking around Central Park and the Upper West Side as I talk about the weather, Daniel Webster, AI + Automations to find fund stuff to do in New York City and starting over with my watch and phone. Links to stuff in this episode Paperclips game: https://www.decisionproblem.com/paperclips/i...

Episode summary Is finding common ground the key to makeing decisions? When will I get the zipper on my jacket fixed? Links to stuff in this episode * ‘All chaos and panic’: Nilay answers your burning Decoder questions: https://www.theverge.com/podcast/846750/decoder-mailbag-qa-nilay-patel-interview-2025 * Zohran Mamdani on FDR, LaGuardia—and Trump: https://www.thenation.com/article/politics/zohra...

Episode summary Two recorded/published episodes in a row! That’s not normal! Nor is the business model for CoreWeave. Bondi Beach, Rhode Island and Lake Mead. Links to stuff in this episode Lake Mead: https://en.wikipedia.org/wiki/Lake_Mead Rhode Island on map: https://www.mapsofindia.com/world-map/usa/rhode-island/location-map.html Bondi Beach: https://en.wikipedia.org/wiki/Bondi_Beach CoreWeave:...

Episode summary This weekend, I walked by the bust of Giuseppe Mazzini. After taking a few photos, I dove into what made Giuseppe so dedicated to his cause of unifying Italy, then discussed how Giuseppe and Zohran Mamdani, in a current sense, would get a long with each other. I touched on other topics like leadership, Benito Mussolini and Stephen Miller. Links to stuff in this episode * Giuseppe M...

Episode summary More thoughts on leadership with a focus on end of year subjective bonuses. Links to stuff in this episode * No one leaving New York City because of Mamdani, say two top real estate CEOs: https://www.cnbc.com/2025/11/14/new-york-city-mayor-zohran-mamdani-real-estate-ceos.html * Office Recovery Strengthens As Vacancy Drops: https://www.credaily.com/briefs/office-recovery-strengthens...