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Good morning - Michael here, writing from the frontlines of Massif & Kroo: Here's what you need to pay attention to in media today:

THE BIG NUMBER: 250,000
That's the number of creator uploads tied to Oscars-related content over the past 12 months, according to YouTube. Those videos generated more than 3 billion views. And the Academy — the institution that once defined cultural prestige on its own terms — brought back Amelia Dimoldenberg as its official red-carpet correspondent and social media ambassador for the second time.
Read that arrangement carefully. The Oscars did not hire Dimoldenberg because they needed another interviewer. They hired her because they needed her distribution. Her audience, her format, her platform fluency — that is the product the Academy is actually buying. The ceremony is the stage. The creator layer is the amplifier that determines whether anything that happens on that stage actually reaches the audience that matters most to advertisers.
That inversion is the real story, and it applies to every legacy event, not just the Oscars.
Here's what shifted.
For decades, major cultural events — awards shows, sporting events, political conventions, fashion weeks — operated on a broadcast model. The event was the content.

The network was the distributor. The audience watched what was presented. The cultural conversation happened afterward, and it happened slowly, mediated through press coverage and water-cooler talk.
That model is gone. The cultural conversation now happens in real time, and it happens through creators — reaction videos, commentary streams, red-carpet breakdowns, fashion critiques, meme production, clip repackaging. The creator layer does not just extend the event's reach. It determines whether the event has cultural velocity at all. Without it, an awards show is a three-hour broadcast that trends for an evening and disappears. With it, the event becomes a content ecosystem that generates months of engagement across platforms.
The leverage shift here is significant. When the Academy makes a creator the official face of its most visible moment — the red carpet — it is acknowledging that the institution's own distribution is insufficient. The broadcast audience for the Oscars has been declining for years. The creator audience is where the growth is. That means the event's cultural relevance is increasingly borrowed from the creator ecosystem, not generated by the event itself.
For creators, that means the opportunity is no longer commentary from the outside. It is embedded access. The creators who position themselves as essential to an event's distribution — not just as reactors but as partners — move from peripheral to structural. Dimoldenberg is not covering the Oscars. She is part of the Oscars product. That distinction matters because it changes the commercial relationship: embedded creators can negotiate differently than outside commentators.
The model extends beyond entertainment. Any brand, institution, or organization that runs large-scale events now faces the same question: can this event generate cultural reach on its own, or does it need a creator layer to distribute it?

For most, the honest answer is the latter. And that means creators who understand event-driven content — live formats, reaction content, interview-style access, real-time commentary — are sitting on a distribution asset that legacy institutions increasingly cannot replicate internally.
For SMBs, the application is practical. If you are running events — conferences, product launches, community gatherings, industry showcases — and you are not building a creator layer into the event from the start, you are treating the event as the entire product. It is not. The event is the input. The content ecosystem that comes out of it is the product. An event without a creator strategy is a one-night experience. An event with one is a distribution engine that generates value for weeks or months afterward.
Cultural institutions are quietly ceding distribution authority to creators, and most of them are doing it voluntarily because they have no alternative. That transfer of distribution power is permanent. It does not reverse when ratings recover or when a particular ceremony has a strong year. The infrastructure of how culture spreads has changed, and creators are now a load-bearing part of that infrastructure.
The operators who understand that — whether they are running award shows, brand activations, industry events, or community experiences — will build their creator relationships before they need them. The ones who treat creators as an afterthought will keep wondering why their events generate a night of attention instead of a quarter of content.
ALSO HAPPENING:
SXSW 2026 is running this week under the most significant structural change in the festival's history — and the pressure is showing.

The Austin Convention Center is closed for demolition, the schedule has been compressed from 10 days to seven, and attendance has been declining in recent years, prompting organizational restructuring and concerns about the festival's financial health. The festival is spreading across Austin into badge-specific "Clubhouse" neighborhoods instead of anchoring in one venue.
For event operators: SXSW's challenge is the same one facing every legacy tentpole — when the central gathering loses its gravitational pull, the distribution of attention fragments. The brands and creators who used to come because everyone was in one building now have to justify showing up to a dispersed citywide experience. The lesson applies to any conference or event: your venue is not your product. Your density of influential attendees is your product. When that density thins, sponsors follow it out the door.
The Grammarly lawsuit is is a talent-identity story hiding inside an AI product dispute.

Julia Angwin filed a class action lawsuit on March 11 against Grammarly's parent company Superhuman, alleging the company used the names and identities of hundreds of journalists, authors, and editors — including Stephen King and Kara Swisher — for its "Expert Review" AI editing tool without consent.
The feature was pulled the same day the lawsuit was filed. For creators: this is the first real legal test of whether an AI company can brand its output with your name and reputation without your permission. The answer will define the value of creator identity in an AI-saturated market. If your name has value — and for any working creator, it does — this case matters to you directly.
YOUR NEXT MOVE: If you run events of any kind — a brand activation, a conference, a product launch, even a local gathering — map out your creator layer before you finalize your programming. Identify three to five creators whose audiences overlap with your target attendee.
Build them into the event structure, not as an afterthought but as a distribution channel with the same priority as your paid media. The event is the moment. The creator content is what makes the moment travel. If you are not designing for that, you are leaving your highest-leverage output on the table.
Thanks for reading! I’ll see you on tomorrow.
Feedback, thoughts, suggestions? Hit the reply!
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This is The Inside Track: Media — short daily notes (Mon-Fri) on where attention is actually going, from the front lines at Massif & Kroo.
If you're into this, you might also like the other stuff I write:
The Weekend Essay (Saturdays) — One idea worth thinking about. Business, decision-making, building things that last.
☐ Business (M/W/F) — What happened, why it matters, what to do.
☐ Aviation (Thursdays) — Straight talk from an actual pilot.
☐ Impact (Periodically) — Doing good in education and healthcare.
You're already set for the media. Add any of those if you want deeper, more frequent updates in areas that matter to you.
— Michael
About Michael Wildes
Michael Wildes is the founder and CEO of Drive Phase Holding Company, a permanent-capital firm focused on building category-defining companies across business, media (owner of Massif & Kroo), aviation, and impact. After leaving a career as a professional pilot, he spent a year as Business Editor at FLYING Magazine writing 330+ articles on aviation's transformation. Now he builds permanent-capital companies focused on long-term trends that compound over decades. Based in Arlington, Virginia.
Connect: mikewildes.com | [email protected]
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