a collection of observations for my future self.observations → newsletter → photo by wil → about wil →
hi. i'm wil.
we moved around a lot...
my earliest memories were probably when we lived on a farm in california.
from there, we moved often. every new town taught me to quietly pay close attention. to listen first, read the room and align signal from noise.
i built a career in technology, leadership and communications, helping organizations bridge people, processes and tools so they could actually get things done.
what i learned, though, is that most companies focus on efficiency while neglecting alignment. they talk about innovation but forget that people make it possible. that imbalance, between people and the systems and businesses they work inside, continues to fascinate me.
today I help companies launch products faster by getting teams on the same page. i’m not a guru or an expert. Just someone who’s seen a lot of change and learned how to navigate it.
stuff i’m (generally) curious about...
→ the future of rich media.
→ the future of organizational structure.
→ audio capture, production, distribution.
→ film and photography.
stuff i’m (professionally) curious about...
→ ai readiness. auditing the "guts" to ensure ai adoption drives margin.
→ narrative alignment. syncing product specs with buying logic.
→ operational sync. building process-based workflows to prevent drift.
→ business visibility. measuring decision-making effectiveness.
professional roles I’ve held...
→ head of marketing | ai software development | new york, ny & london, uk
→ enterprise business development | telecommunications | montana
→ head of marketing, media relations | data centers | new york, ny
→ head of sales and marketing | software development | washington, dc
→ business development | b2b software | sydney, aus & san francisco, ca
→ investment banking analyst | boutique m&a advisory | san francisco, ca
→ network, systems admin | integrated circuits | silicon valley, ca
my formal education...
→ bsc, business computer telecommunications: csu east bay (hayward, ca)
→ mba, marketing: ageno school of business, ggu (san francisco, ca)
observations.
i'm an observer, likely the last one to jump into a conversation. i'd much rather get a better understanding of context before shooting my mouth off. (though, there are times...)the following observations are short pieces–audio, text, video–usually captured while i'm on one of my walks (hat tip: craig mod).observations are really letters to my future self, capturing how i thought about a topic today. they are organized by month.
july 2026.
july 12, 2026.i can’t stop thinking about this week’s product release from openai.the changes feel big in both interface and implication. (as of 8:32am est this morning, i’m unable to log into the chatgpt ios app, however i can log into the chatgpt web app.)users, including me, are confused by the change in app names, app functions and how to continue using the apps in the same manner we have been using the apps.it just seems that overnight, poof, everything is gone or changed with zero education, zero notice or zero tips.and the confusion makes me think about the fragility of organizational and leadership trust in fast-moving ai companies.with 1 billion reported monthly users of chatgpt, it feels like the brand is wobbling in a way that could ripple into revenue, leadership confidence and the ipo narrative.how much money was (is) invested in openai?i don’t know if this is the first crack in a larger pattern or just a blip highlighted by my own frustration.
the tech world is full of moments that felt seismic and faded quickly, however this fu@$ up feels really big.given openai’s already-riddled past of leadership changes, which leader takes the fall for this change? maybe they pin it on the outgoing apps person? even if they do, do investors ask for a reset of top leadership, similar to the changes at uber a few years ago?has microsoft’s patience run out?has the product update rollout only impacting a small set of users, where there is still time to reverse course and pin the problem to poor messaging/positioing?the line between product, leadership and strategy feels unusually thin.
photo
i took this photo at a little after 5am on saturday, july 11. 8’m facing north in taking this photo, which was odd to me. normally when i’m walking in the mornings, i see the moon over the midtown, which is south from where i normally walk.
july 3, 2026.i very much enjoy the early mornings, especially walking and taking photos in big cities.on this morning, i walked around central park and the upper west side, with a dji osmo nano attached to my digital camera (with zoom lens), filming what i saw as i found compositions and snapped photos.here's the result, background music included if you so choose.
cover photo.
on july 4, 2026, i walked down to pier 1 on the west side of manhattan.
it was a very hot and humid weekend and since there wasn't much shade on the pier, there weren't many people waiting on the pier for the airshow.
i found a good spot on the bridge and positioned myself facing the george washington bridge, assuming the airshow would fly up the hudson river.
between 10am and 12p, i clicked the shutter button 399 times.
only 35 photos were flagged as 'favorites'.
this was one of them.
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