NYC Now Fines Hard-to-Cancel Subscriptions

Ads are awesome. Ignorance is expensive. And the American dream is alive on the wild web.

Today, New York City starts fining businesses that make subscriptions hard to cancel, a boot brand swapped its email agency for Grok Bot, and Mark Zuckerberg says AI agents will create shoppers who never existed. TJ Bongiorno of The Outgoing Co. is our guest host today, and Postscript's Laura Serino and Shopify's Alexandra Clark join us live. Here's what we're riding into at noon.

✶ SUBSCRIPTIONS

New York City is now the first city in the country with a Click-to-Cancel rule. Businesses that make it hard to cancel a subscription, including "free trials" that quietly convert to paid and cancellation buried behind extra steps, face restitution and fines starting at $525 per violation. The rule took effect October 1 (NYC Mayor's Office). Penalties climb to $3,500 for a third violation and beyond (DLA Piper).

Mayor Mamdani is now pointing New Yorkers to a complaint portal: "If you can sign up with a click, you must be able to cancel with one" (NYC Mayor on X). Taylor Holiday thinks the bigger threat is agents: "There is a non-zero chance that the entire consumer subscription economy exists expressly because enough people forget or are too lazy to cancel. Agents could change all of that" (Taylor Holiday on X).

✶ AI AGENTS

Chisos founder Will Roman: "Replaced my email agency with @bot. Sorry, not sorry. Grok Bot writes in our brand voice, pulls product photos from Dropbox, builds hero artwork in Figma, and drops a finished editable campaign into Klaviyo as a draft. I review for five minutes and hit send" (Will Roman on X).

✶ AI AGENTS

Eric Bandholz says Beardbrand built an AI phone agent in about two days, and it's now the brand's main support line. The stack: xAI's Voice Agent Builder at 8 cents a minute, Shopify for orders, Recharge for subscriptions, and a small Cloudflare Worker in between so Shopify keys never touch the agent. He also split order lookups into two levels after the agent read back a stranger's details early on (Eric Bandholz on X). "Crazy to see someone in the industry achieve a musk retweet," Colin McGuire wrote (Colin McGuire on X).

✶ PAID MEDIA

More than 1,400 advertisers ran ads on ChatGPT in August, up 8% from July. But one agency exec says ChatGPT's cost per click runs about 6x Google's, and "Generally the results have been pretty bad." Brands also can't yet target a specific shopper the way they can on other platforms (Modern Retail).

✶ WATCH & REACT

On Cheeky Pint, Mark Zuckerberg said he used Instacart about twice a year on his wife's account. Then he got his own account for Muse, Meta's AI agent, and now orders once or twice a week: "I am a new Instacart subscriber, and I just wouldn't have done this before." His point is that the opportunity isn't a 20% better conversion rate, it's net-new customers created by agents (Seijin Jung on X, Cheeky Pint).

FOUNDER, THE OUTGOING CO.

TJ worked in mortgages, learned to code at a bootcamp, and became a sales engineer before starting a supplement brand on the side. Today The Outgoing Co. makes nootropics and functional drinks meant as an alternative to alcohol, and he grew it into a multi-seven-figure brand without employees (Business Unchained). He also co-hosts Down To Health (TJ on X).

DIRECTOR OF CONTENT, COMMUNITY & BRAND, POSTSCRIPT

Laura has spent more than five years at Postscript and leads its content, community, and brand work (LinkedIn). She co-led Skeptics, Postscript's scripted mini-series about a chaotic DTC soda brand, which wrapped its season this summer (Sam Melnick on LinkedIn).

VP, COMMUNICATIONS & PUBLIC AFFAIRS, SHOPIFY

Alexandra leads communications and public affairs at Shopify and is a founding partner at Backbone Angels (LinkedIn). This is her first time on the show.

Follow the guests: Laura Serino on LinkedIn ✶ Alexandra Clark on X

Wingstop's new Wicked Punch flavor has a Sour Patch Kids Redberry Glaze topped with candy Bitz. It drops October 27 for Halloween, with early access for Club Wingstop members on the 23rd (Snackolator on X).

Target appears to be testing raffles for high-demand Pokémon products, starting with the 30th Celebration UPC. Instead of racing the drop, you enter for a chance to buy (PokemonAI on X).

AppLovin says advertisers that scaled two to three weeks before BFCM nearly doubled their revenue. New customer checkouts jumped more than 3x, and 12.5% of BFCM customers bought again within six months (AppLovin on X).

Screenshot any cart you like, run it through the AI prompt, and import it into your store. Aftersell Cart says it goes live in under five minutes with no code, plus 18+ upsell and cross-sell widgets. Aftersell and Grüns host a masterclass on October 22. This one is a paid post (Max Sturtevant on X).

"For an additional 2$ in Chinese McDonald's you can get an onion back massager. Elite merch if you ask me" (Flo on X).

✶ FEATURED SPONSOR: NORTHBEAM

If you live in the Ads Manager, you know the problem: every platform takes credit, and every dashboard tells a different story. Meta says 4.2 ROAS. TikTok claims the same conversion. Which one is lying? Honestly — all of them.

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UNIVERSAL ADS
Performance TV for DTC brands. Code UACOWBOY gets $1,500 in matched ad credits. universalads.com