Hey Cowboys,

Happy Monday! We’re bringing you a fresh round of DTC, retail, tech, and ecommerce news to unpack this week.

LIVE NOW — come hang out on X and YouTube.

Today’s lineup 👇 and stories.

Prophecy, Persuasion, and Hype

Chris breaks down the emails that make people buy and Andreea explains what it really takes to build an influencer program that prints money instead of burning product.

ChatGPT Ads Are So Back?

OpenAI is pushing further into advertising with a redesigned onboarding flow that lets new advertisers build a ChatGPT ad campaign in under 60 seconds. The launch follows the company's recent expansion of ChatGPT ads to 31 countries and comes with a $500 matching ad credit offer as OpenAI works to pull in a share of the more than $1 trillion marketers are projected to spend in 2026.

The Rundown:

  • The new onboarding tool was unveiled during an OpenAI webinar for marketers earlier this month. Advertisers enter their website URL, click "Ad Preview," and OpenAI's model analyzes the business's objective, product lineup, and target customer to generate a campaign.

  • The model also recommends which user journeys on ChatGPT the campaign should surface in, based on where users are in their intent.

  • New advertisers get $500 in matching ad credits for their first $500 in spend, a standard incentive across major ad platforms.

  • The rollout follows OpenAI's announcement of ChatGPT ads in 31 countries, marking a rapid expansion of the platform's ad footprint.

  • OpenAI told investors revenue grew 18% quarter over quarter, but losses also increased, according to the Wall Street Journal. The company is targeting an IPO and needs a clearer path to profitability.

  • OpenAI's pitch positions ChatGPT as a consolidated shopping journey, replacing what was previously spread across websites, reviews, and offline channels.

OpenAI is building out its ad business at pace, with the 31-country expansion, the new onboarding flow, and the credit incentive all landing within weeks of each other. The ad platform is now a central piece of the company's push toward profitability ahead of a potential public offering.

Top Stories: Infinite Livestreams, Festivals x GenZ, American Olive Oil is Back

Infinite Livestreams - Minimax H3 Max is generating footage faster than viewers can watch it, allowing a developer to run an endless AI-generated livestream on Twitch. The demo hints at a future where every viewer could have a personalized, continuously generated stream.

Using Festivals to Attract GenZ - Bubba debuted its new fashion-forward identity at Lollapalooza, drawing 20,000+ people to its activation and generating more than 3 million social views. The nearly 30-year-old brand is moving away from its rugged image and targeting younger female consumers with colorful, lifestyle-focused products.

American Olive Oil is Back - Farmers are bringing olive groves back to Georgia and producing fresh Southern olive oil for the first time in generations. The local oil can go from tree to bottle in hours, giving U.S. growers an edge over imported oils that may spend months in transit and storage.

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Ecomm Cowboy is the go-to live show for ecommerce operators, breaking down the latest DTC, retail, and AI news while interviewing the founders and executives building today's fastest-growing brands.

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Made Possible By:

Seguno - the Shopify-native marketing suite for brands that run it themselves.
Insense - The all-in-one UGC and influencer marketing platform.
Postscript - Make more money from every SMS message.
Proxima - Use real conversion data to power your creative briefs.
Northbeam - Measure the “unmeasurable,” make your marketing profitable.
Rokt Aftersell - More profit from the orders you’re already getting.
Universal Ads - TV ads that deliver for performance marketers.
Richpanel - The AI helpdesk that saves you headaches (and money).
SATHI - Affiliate attribution beyond last-click commissions.
Slash - A better business banking platform.
Trendtrack - Track competitors' winning marketing strategies daily.
Tie - The internet’s #1 shopper ID platform.
Proppel - The best recruitment agency for ecom brands and agencies.

See you on the stream,
Ecomm Cowboy Team