Why I bet on a newsletter (and how it put me on a billboard)

Every content strategy rents attention at the top across search and social. And that rented layer keeps getting shakier. 68% of Google searches now end without a click, and where AI Overviews appear it's 83%.

Feeds throttle organic reach. AI floods every channel with infinite content.

Which makes what you own worth more. That's why I started this newsletter. A list no algorithm can throttle is what turns borrowed attention into a business.

Every creator and brand should have a newsletter in their funnel. I built The Night Shift (formerly Creative Commerce) on Beehiiv (and not Substack) because here you're not just publishing, you're building a business.

And this month it led somewhere I still can't quite believe. That's me below, on a billboard in Times Square (!!!), as part of a creator feature powered by Beehiiv.

Have questions about launching a newsletter? Feel free to hit reply and ask! Now let’s get into it. xo

🔥 Featured Content

Creators are moving into brands’ AI search playbooks

There’s a new deliverable on the creator brief: AI visibility. As more people start their shopping journey in AI chatbots, marketers are hoping creators can help put their brand names in front of those shoppers.

I spent hours studying why things go viral. Here's what I found.

“[There are] six principles behind why things spread. And I want to walk you through all of them, with real examples from creators doing it right now.”

— Mackensie D.

Ann Taylor stages a brand comeback with Substack

Ann Taylor's "This Is Ann" is its first major integrated campaign in nearly a decade, and the anchor is an owned newsletter. A NYFW pop-up lands Sept 8, with a first-ever brand ambassador program in early 2027.

🤳 Content Inspo

This is where I would [hang] all [our favorite] [Drool prints]. [LINK]
Gamify your product or service to show its many different use cases. Will make it easy for someone to say “ah yes that would work for me!”

Things [stylish] people do differently. [LINK]
Imagine the embodiment of who your ideal customer wants to become and highlight the traits and actions of that persona (and ask yourself how it aligns with how your brand, service, or content helps them get there).

Turn an update into a narrative carousel with a strong POV hook. [LINK]
You may have seen some quarterly or mid-year updates going around. Anchoring it around a perspective or insight is a way to make it more engaging, relatable, and valuable.

💬 Tip of the day:

💎 Creator Spotlight

Madison Utendahl is an incredible creative director, writer, and strategist. She founded Utendahl Creative, the agency behind brand identities for Law Roach, Lena Dunham, and John Legend. She now runs Utendahl Consulting and writes BURNT, a cultural Substack about burnout. She’s a two-time Webby winner + Forbes 30 Under 30 honoree.

Her content is so fresh an insightful. She has been on my favorites list for quite some time and should be on yours too.

Follow Madison —> @madison.utendahl

📡 On Our Radar

Meta to pay Up to $17.1 billion in landmark settlement over social media addiction claims. [LINK]

Microdramas are the death rattle of Hollywood. [LINK]

Trying to personify your brand? Consider a puppet. [LINK]

Why Nuuly is betting on a microdrama for its social-first fall campaign. [LINK]

Inside toy brand Sticki Rolls’ YouTube strategy to win over Gen Alpha. [LINK]

ICYMI: The Walt Disney company and TikTok announce a first-of-its-kind global short-form content-sharing deal. [LINK]

Creator partnerships are no longer just content opportunities or one component of a brand’s social strategy, they’re core components of paid media strategy. [LINK]

🔮 Platform Updates

🎶 TikTok

TikTok launched a new Substack called The Creator’s Cut. It’s focused on TikTok LIVE and written by creators. [LINK]

TikTok explores peer-to-peer payments via DMs, report says. [LINK]

TikTok Live adds AI-generated intros. [LINK]

TikTok is changing how Gen Z eats, new study says. [LINK]

📸 Meta / Instagram

Meta AI is getting a Mac app. [LINK]

Meta removes option to exclude ad placements. [LINK]

Meta highlights rising brand opportunities in women’s sports. [LINK]

New Meta AI features for small businesses. [LINK]

Meta brings Pocket, an app that lets you vibe-code and share games, to US users. [LINK]

🤳 YouTube

Making thumbnails easier on YouTube: new options and tools for creators to enhance their videos. [LINK]

YouTube is expanding "Stations": 24/7 TV-style streams that continuously play a selection of videos from a creator, podcast, or media channel. Only select creators have access for now. [LINK]

YouTube simplifies its AI claims process. [LINK]

YouTube will now count a view as soon as a video starts playing. [LINK]

YouTube rolls out improvements for connected TV. [LINK]

☠️ 𝕏 

X Chat updates composer. [LINK]

Elon Musk’s X Money app is rolling out in the US. [LINK]

The X app for iOS now has a built-in video editor. [LINK]

X adds text overlays to video. [LINK]

🟦 LinkedIn

New research reveals 75% of LinkedIn AI citations come from individual profiles, not company pages. [LINK]

Over 1 million people have clicked LinkedIn’s AI slop button. [LINK]

LinkedIn playbook offers tips on effective ad campaigns. [LINK]

👻 Snapchat

Snapchat tries to teach brands to be funny. [LINK]

Snapchat offers third-party AI ad integration. [LINK]

🤖 AI Boom

‘Algorithms don’t care about aesthetics’: AI has a new favorite product and it’s not necessarily yours. [LINK]

Google goes back to school with new AI study tools. [LINK]

Google gives publishers a new way to fight AI-driven traffic losses. [LINK]

Reddit tests AI-powered conversations. [LINK]

AI isn’t close to curing cancer. This startup says it knows what it will take. [LINK]

OpenAI launches ChatGPT for Teens with stronger safeguards. [LINK]

Google will now allow users to remove visible watermark from its AI generations. [LINK]

ChatGPT has entered the group chat. Texters have…feelings about it. [LINK]

Winter Mendelson
Co-Founder & Chief Creative Officer: Posture Media

🦇 Let’s connect on Instagram and LinkedIn

P.S. I will probably have typos in the event that my dad is unavailable to proofread. Sorry in advance.

​Need a hands-on social media partner? I’m the Co-Founder of Posture Media, a Brooklyn-based social media agency that helps companies make social an unfair competitive advantage. Let’s chat if you’re looking for a strategic creative partner in 2026.

Were you forwarded this email? Feel free to sign up here.