Hi Shopifreaks
Last year I launched a new project called 90 Second Pitches with the goal of introducing merchants to innovative e-commerce solutions that can help grow their businesses. You can subscribe to the channel on YouTube and LinkedIn.
Since then I've had the pleasure of receiving pitches from outstanding companies including:
- Organizely – an inventory management platform for Shopify merchants, built by a Shopify merchant to solve his own warehouse disorder. (A lifesaver for small brands that fulfill their own orders.)
- Order Rescue – a Shopify app that helps merchants recover sales when customer-inputted discount codes don't work. (It works amazingly.)
- Section Store – a library of pre-built sections for Shopify stores that can expand the functionality of any theme. (I'm a long-time user.)
- Cuttable – an ultra-fast solution for conceptualizing, designing, and publishing Meta ad campaigns. (One of the best I've seen on the market.)
- Infinite Color Search – a search tool that lets your customers discover products by color. (Such an amazing tool, I almost invested in the company. I regret not doing so.)
I'm thankful to have discovered these solutions and am now using many of them myself on client stores. I hope the 90 Second Pitches channel has helped you discover tools to grow your business too.
Next week, I've got a new pitch headed your way for an app that brings the power of Google Search & AI to Shopify stores, built by former Google engineers who understand the technology better than anyone. I learned about this app a few years ago, right after they launched, and it was actually one of my inspirations for launching 90 Second Pitches — because I didn't have an outlet to educate my readers about it at the time, but knew I needed to build one. Stay tuned for next week to watch their 90 Second Pitch!
And now, onto a jam-packed edition with lots of news from Cannes Lions 2026 and several new launches from major platforms and marketplaces.
In this week's edition I cover:
- Meta's new prediction markets app
- Amazon's pesky black market
- Amazon's new conversational display ads
- Meta's new AI advertising and creator tools
- X launches X Money to Premium+ users
- Shopify partners with Trustpilot
- StockX launches a peer-to-peer marketplace
- Amazon is advertising on ChatGPT
- Starbucks is first to test TikTok's new Creator Network
- Sam Altman is getting rich outside of OpenAI
- REI got roasted for its AI-generated ads
All this and more in this week's 284th Edition of Shopifreaks. Thanks for subscribing and sharing!
Stat of the Week
U.S. shoppers spent more than $26.4B online across all retailers during Prime Day, which ran from June 23-26, according to Adobe. eMarketer projected ahead of the event that Amazon's own U.S. sales would reach about $15.6B during the event, up 7.1% YoY, accounting for roughly 60% of total U.S. online spending. How are these companies so good at making these estimates?! It's honestly quite astonishing.
1. Meta is building a prediction markets app called Arena
Meta is building an experimental prediction markets app internally called “Arena” at Mark Zuckerberg's direction, aiming to compete with platforms like Polymarket and Kalshi, according to The New York Times.
The app would run independently of Facebook, Instagram, WhatsApp, and Messenger but lean on Meta's existing audiences to drive downloads. I'd imagine similar to how Facebook constantly throws Threads posts in your face when scrolling in an attempt to get you to download the app.
Unlike competing predictions-market apps, Arena users would not wager real money. The app would instead rely on a digital points system (Zuck Bucks?), according to one source, though Meta has not ruled out eventually allowing real money betting.
Insiders told The New York Times that the predictions app is still experimental, but a top priority of Zuckerberg, and is part of a broader push at the company to create apps based on emerging social behavior online, as opposed to piling all new features into Facebook and Instagram.
If Arena sounds familiar, it's because Meta has already tried its hand at a predictions app. In 2020, it released Forecast, a standalone app that prompted users to make guesses about the world in the early days of the pandemic that also used a point system instead of real money. However, the company shuttered the app in 2022. (What do I always say? “Meta quits everything too early.”)
I can only imagine the sycophant yes-men that Zuckerberg surrounds himself with…
Mark Zuckerberg: “For my next idea, I want to pioneer the predictions market industry with a standalone app that lets people place bets on the outcome of real-world events.”
Meta Executives: “Brilliant! Revolutionary! I can't believe no one's thought of that before! And might I say… nice penis, Mark!”
The prediction market industry has exploded from $50B in combined Polymarket and Kalshi trades in 2025 to over $130B already this year. Senator Richard Blumenthal attacked the plan as Meta “profiting from addiction.” He wrote, “Meta copied slot machines to addict kids to Instagram. Now Zuckerberg is turning his company into a prediction market.” However, to be fair, he should go after Polymarket and Kalshi too. It's not like Meta invented the predictions market. It's just copying it.
2. Amazon still has an employee-access black market problem
Amazon seller Jack Nekhala, inventor of the Bed Scrunchie bedding product, shared evidence with Bloomberg of an international black market in which middlemen on apps like WeChat, WhatsApp, and Telegram sell access to Amazon employees willing to trade inside information and favors for a price.
After Amazon suspended his account over an alleged review-policy violation and froze $90,000, a woman contacted Nekhala on WeChat offering to bribe an Amazon contact to recover the funds for a cut. The woman had already obtained his confidential seller records, which only certain employees have access to.
Nekhala says he declined the offer and reported it to Amazon twice, in an attempt to get back in the company's good graces so that they'd reinstate his seller account. An Amazon representative acknowledged his reports and committed to “do some digging,” promising to e-mail him instructions on how to share his evidence with the company, but Nekhala never heard back after that.
Amazon spokesperson Brad Glasser told Bloomberg:
“As one of the world’s largest online marketplaces, there’s always the risk of bad actors attempting to exploit, defraud or otherwise scam our business. On very rare occasions, an employee can be involved in such instances. We invest heavily in this area and have dedicated teams and systems in place to prevent all types of fraud, including by our own employees.”
However, he did not explain the lack of follow-up with Nekhala.
If all this sounds like déjà vu, it's because these types of internal dealings have already been exposed at Amazon on a grand scale several years ago. In 2020, federal prosecutors exposed an international bribery ring involving Amazon sellers and employees that allegedly extracted about $100k helping sellers sabotage their competitors. The investigation led to guilty pleas by five people in the U.S., including several Amazon seller consultants and a former Amazon employee, while a sixth fled abroad and remains at large.
Glasser told Bloomberg that Amazon works with law enforcement as needed if it discovers employees doing illegal shit, but declined to describe how the company combats fraudulent activity because “we don't want to share those methods with bad actors who might exploit them.”
3. Amazon launches conversational display ads across the Internet
Amazon began running conversational display ads across the open web for the first time, embedding prompts into banners that let consumers open an Alexa chat and ask for product details, which Alexa remembers if they return, according to Adweek. The expansion comes after Amazon updated its Responsive eCommerce Creative, a shoppable ad format that pulls in product imagery, pricing, and reviews, to now support AI-generated images, animation, and video, rather than just static images and reviews.
Amazon says 20% of shoppers who hit a prompt continue chatting with Alexa, and that 70% of buyers from the ads are brand-new customers. (I'm assuming they mean “new customer for the brand” and not “new Amazon customers” — the latter of which is a stat I don't think is even possible anymore in 2026, given Amazon's market share.)
Amazon also says that advertisers using its AI features see a 14% higher click-through rate and 7% higher return on ad spend. (But don't get too excited, because Amazon will come for that extra margin before you know it.)
The off-site units are priced on a CPM model versus the CPC pricing on Amazon's own site, which Adweek says “could reflect where they actually sit in the sales funnel.” However, the pricing could also be introductory as Amazon tests the format so that it can properly price a cost-per-click.
Personally, I think the format is brilliant. I'm tired of traditional display advertising and feel that the format is long overdue for an overhaul. Amazon's take on conversational display ads turns legacy banner ads into a shopping tool that visitors can engage with, as opposed to a traditional binary decision of clicking or ignoring.
4. Meta unveils new AI creative and creator tools at Cannes Lions 2026
Meta used its Cannes Lions 2026 appearance to roll out a suite of new AI-powered advertising tools spanning creative production, creator partnerships, and customer-facing business agents, pitching the updates as making AI-enabled ad creation accessible to every marketer rather than just technical ad buyers.
Highlights from the presentation include:
- An end-to-end creative solution with brand-aware generation tools, including a “brand memory” feature that learns a company's identity and tone from its existing ads, so marketers can scale creative production while keeping it on-brand. Meta is building agency integrations in from the start, beginning with a WPP collaboration that brings the experience into WPP Open.
- A dedicated creative strategy-and-optimization space that closes the loop between performance and production, showing marketers which ads are working, generating new ones based on what's performing, and testing them in one shared space for creative and media teams.
- Paid performance insights inside the discovery hub, letting advertisers see how creator-driven ads actually stack up right where they found the content, rather than discovering creators in one place and measuring results somewhere else.
- Expanded generative AI in Ads Manager, including text generation that now writes copy appearing directly inside image creative (as opposed to just in the ad headlines), new language support for text-on-media and video voiceover, and a built-in creative approval workflow in testing.
- A unified Meta Creator Marketing Hub, merging Creator Marketplace and the Partnership Ads Hub into a single surface launching later this year, with Facebook creators joining the 5M+ Instagram creators already discoverable in the marketplace for the first time.
- Enhanced creator content discovery, including the ability to surface posts from creators a business doesn't already work with, filter by product-tagged content, and tap pre-permissioned content from creators who've opted in to run their posts as ads.
- The Meta Business Agent Platform, letting enterprises plug existing systems in to build and deploy AI agents at scale across Meta's messaging apps, which Meta says more than a million businesses are already using to turn customer messages into conversions.
- A double-handlebar feature that turns any real photo of a bicycle into an AI-generated photo of a bike with two sets of handlebars. (Just a joke… see my Most Ridiculous Story of the Week at the bottom of this edition to understand it.)
Meta wrote in its follow-up announcement:
“Every creative insight trains the next campaign. Every creator partnership fuels the next ad. And every AI conversation sharpens the next recommendation. With these new updates, we’re accelerating our ecosystem and giving marketers, advertisers, and agencies a platform that compounds performance.”
Good stuff all around. Tracking the performance of ads, particularly across collaborations with creators, has historically been difficult, and some of these new updates seem to tackle the issue head-on, which will be a win for advertisers and creators alike.
5. X rolls out its X Money payments service to Premium+ subscribers
X began rolling out its X Money payments service to select Premium+ subscribers, kicking off the long-anticipated service by a user sending Elon Musk $25 to test its peer-to-peer money transfer feature. (Why didn't Musk send him the $25?)
In addition to P2P transfers, X Money offers up to $10M FDIC insurance on deposits (spread across multiple partner banks), a metal Visa debit card with free ATM withdrawals and no foreign transaction fees, as well as the ability to pay by wire transfer or check, similar to how Bill Pay works at banks.
Even more notable, the account advertises a 6% APY on deposits and a 3% cashback on debit card transactions, which is around twice what other leading banks and fintechs are currently offering. The service is licensed in 41 states plus DC, but not yet New York or Massachusetts, among others.
Earlier this year, I reported that Senator Elizabeth Warren sent a letter to Elon Musk, raising concerns about the upcoming launch of X Money. Her letter touches on how the launch comes one year after Musk pushed to dismantle the CFPB and how X Money partners with Cross River Bank, which Warren labeled as a “repeat offender” of “unsafe and unsound practices related to fair lending.”
I recognized some of her concerns, but pushed back on her claims that the 6% APY is built on “risky investments” and “intrusive data monetization activities.” There are plenty of legitimate investments that could earn that yield. Just because other banks keep the spread for themselves doesn't mean the vehicles don't exist. Earlier this month, I wrote about how U.S. banks captured roughly $485B a year by paying customers with savings accounts far less than the Federal Reserve paid them, according to a 17-year analysis of Federal Reserve and FDIC data.
There's a huge spread between what banks take in and what they dish out, and the industry is ripe for disruption. X Money could put some much-needed pressure on legacy banks to make their financial products more attractive for your average customer. I hope it does.
As many of you know, Elon Musk was the founder of X.com, one of the Internet's original payment systems, which later merged with Confinity's PayPal product and eventually took on the PayPal name. Decades ago, Musk was very much at odds with his partners at PayPal, almost ousted as CEO at one point, and it's been very well documented since then that he always planned to one day build his original vision of a financial platform. He took a few side quests along the way, building electric vehicles, rocket ships, underground tunnels, chips that connect to your brain, and of course buying a social network, but it's interesting to see him follow through on his original X Money vision years later.
6. Shopify partners with Trustpilot to integrate customer reviews into stores
Trustpilot, the consumer-review platform that hosts feedback about businesses, partnered with Shopify to let merchants collect, manage, and showcase Trustpilot reviews inside their own storefronts via a newly enhanced Trustpilot app.
AI search engines and shopping assistants rely on data like Trustpilot's to determine the reputation, credibility, and authority of a brand. So for merchants, Trustpilot's reviews are one factor that can influence a brand's visibility. The company says that click-through traffic from AI search is up 1,490% in its latest financial year, indicating that its content is already a key resource for LLMs.
CEO Adrian Blair told Bloomberg:
“The key problem that all these Shopify merchants are facing is how do you actually build trust with customers now in the age of AI? There is so much that is now being created by AI, this kind of synthetic content, and Trustpilot is a canonical source of what people say about their experiences with businesses.”
The integrated Trustpilot reviews go live on Shopify today (June 29), marking the first of what Trustpilot hopes to be many partnerships to cement its role as a trusted source of customer feedback.
Trustpilot was founded in 2007 (same year as Google Reviews) and hosts more than 330M consumer reviews, attracting around 60M monthly active users globally, with insanely expensive subscription services to businesses accounting for most of its revenue. I never quite understood the incentive for businesses to pay Trustpilot. Why am I paying a company to hand them my customer's information and grow their platform into the source of truth about my business? It feels very Yelp-ish.
Personally, I won't be integrating Trustpilot reviews with client stores, unless they already have a healthy presence on the platform. Meaning, I'll showcase and build on the reviews they've got, but I won't be starting from scratch building a presence on Trustpilot. How about you? Hit reply and let me know.
7. StockX launches a peer-to-peer marketplace for used sneakers and vintage apparel
StockX launched StockX Listings, a peer-to-peer marketplace for used sneakers and vintage apparel, marking its first move beyond the verified catalog model it built its reputation on, according to Value Added Resource.
Here's how it works:
- Sellers list used, vintage, and other items that may not fit into StockX's existing catalog.
- The platform's AI technology can help identify products from a photo, pre-fill listing details, and offer pricing guidance.
- The listings will appear alongside its existing Verified Marketplace, giving buyers a single product view where they can compare new and used options (similar to Amazon, where you can view all seller options on one screen).
- Every seller must have their identity verified before listing, and seller payments are held until delivery is confirmed.
The Catch: Sellers ship the items directly to buyers, bypassing StockX's traditional product authentication flow of having all items sent to their warehouse for verification before reaching customers. However, the company will offer an optional verification on eligible items, allowing buyers to pay to have an item sent to a StockX Verification Center first, before being shipped to their homes.
StockX CEO Greg Schwartz wrote:
“When we started StockX, the idea was simple: create a marketplace built on trust, data, and transparency. That core hasn’t changed, but we’ll now be able to provide our customers with a wider selection of the products they love, and the ability to sell products they’ve previously purchased faster than ever before.”
I think it's a smart move and a natural evolution for the platform. At some point, a seller with hundreds or thousands of 5-star reviews is as credible (or more so) to a buyer as a faceless “verification expert” at one of StockX's facilities. It's nice to have an optional verification feature for buyers, but it's certainly not necessary for every item to sell through its platform.
Removing the requirement speeds up the selling process and adds margin on items (potentially represented by a lower out-of-pocket cost to buyers). That said, it can certainly open the door to problems, but none that platforms like eBay and Amazon don't already have solutions for dealing with. StockX requiring ID verification from all sellers before they can list an item is a step in the right direction to avoid some of the problems faced by other marketplaces.
8. Amazon ads on ChatGPT have been spotted in the wild
Amazon began buying ads on ChatGPT for the first time, becoming one of the highest-profile retailers in OpenAI's emerging ad business, as spotted by e-commerce analyst Juozas Kaziukėnas. The ads link shoppers back to Amazon's storefront, where the company controls the customer experience and transaction, as opposed to letting them checkout within ChatGPT's interface.
Kaziukėnas wrote on a LinkedIn post:
“This feels symbolic because: Amazon is not participating in any shopping experiments by ChatGPT or other AI chat agents. In fact, they are actively blocking AI scrapers to break their functionality… Amazon and other retailers don't want to be aggregated by ChatGPT but they will gladly buy ads on ChatGPT to bring users to their storefronts.”
A few days later, in a separate LinkedIn post, he reported:
“I'm now seeing the third iteration of ads in ChatGPT. The ad format is evolving to fit a larger image and take up less horizontal space (to fit multiple ads side by side; although, so far I'm still only seeing one ad at a time). They've got a few more ad formats coming soon, specifically for shopping. But I'd like to see AI-native ads, not just typical banners – Google is leading here with more creative ad integrations.”
Click those links above to see his original posts, which include screenshots of the ads themselves.
Last July, I reported that Amazon removed its entire Google Shopping advertising presence across all major markets for 31 days, marking one of the company's most dramatic exits from Google's retail ad ecosystem in recent history. Then in September, I reported that across 79,000+ keywords, Amazon lost 31% of its organic product card rankings, according to data from Audience Key. It seems that the hunt for customer acquisition channels is never over, even for leaders like Amazon.
9. Other e-commerce news of interest
OpenAI used its first Cannes Lions appearance to declare that it's “clearly in the advertising business now,” while referring to its ads business as a “baby” that's just “19 weeks” old. CRO Denise Dresser, who started at OpenAI in December, said the company wants its advertising business to be measured by whether the ads help people get things done. She added, “We're moving from the attention economy to the intelligence economy, and what consumers really want is usefulness, and so that's what we're all about.” Head of global ads David Dugan, a 12-year Meta veteran who joined OpenAI in April, said roughly 20% of the platform's 900M weekly users' queries carry direct commercial intent, with many more upper-funnel questions holding commercial potential, while stressing OpenAI will never share conversational data with advertisers. Honestly, for the first time, it feels like OpenAI has some adults in the room when talking about its advertising business!
In other OpenAI ad news… The rate at which ChatGPT users dismiss ads has fallen 50% since it launched its advertising business in February, according to OpenAI’s head of global ads solutions David Dugan, a metric which the company treats as a proxy for relevance and a sign that users find the ads more useful. Dugan said that testing has shown “no degradation in user behavior” when someone is shown an ad, which he says gives the company confidence the format isn't hurting the experience. ChatGPT ads now run in seven markets after adding Japan and South Korea, with Brazil and Mexico next, and over 2,000 brands now advertising on the platform, according to Criteo.
Starbucks is piloting a custom Creator Network in TikTok's Content Suite, becoming the first brand to test the tool, which TikTok unveiled at Cannes Lions last week as a way for brands to assemble a pool of employees, partners, or advocates whose content can power ads. The pilot builds on Starbucks' Green Apron Creators program from 2024, letting the company share campaign briefs with select employee-creators and compensate them through ad revenue sharing as their content runs in paid advertising. The move leans on already-heavy posting by Starbucks' primarily Gen Z baristas, who post at three times the rate of employees at similar-sized chains. Sprout Social data shows 61% of Gen Z frequently learn about new products from employee-generated content, a trend that Starbucks aims to embrace with the pilot program, which kicks off this summer.
TikTok also used Cannes Lions to unveil Symphony Agent, an AI ad agent that pairs advertisers' campaign goals with insights from the app's top content and trends to match brands with relevant creators and build custom video ads. The agent ships with safeguards like AI labels, invisible watermarks, and content-moderation filters, and integrates across TikTok's Symphony Creative Studio, Content Suite, and brand-creator platform TikTok One. Lastly, TikTok announced that it struck a deal to fold its Symphony AI tools into Zoyumi, the AI media-buying platform run by advertising holding giant Dentsu, putting image-to-video generation, caption removal, dubbing, and digital avatars in front of Dentsu's big-brand clients.
commercetools launched a new toolset called commercetools for Builders that lets developers create e-commerce storefronts using AI tools like Claude Code, Cursor, and Vercel's v0 from natural-language prompts instead of hand-coding from scratch. The company also unveiled a Commerce Integration Layer, launching later this year, which centralizes the connections between commerce, content, search, promotions, and tax systems, designed to speed up the integration work that the company says has historically stretched enterprise commerce projects across months. Founder Dirk Hoerig pitched the launches, which are part of the company's broader “autonomous commerce” push, as collapsing build times from a project plan to a prompt. It seems to me that commercetools is attempting to find a happy medium between its original value proposition of offering a commerce platform that gives merchants full control and solutions that make it more plug-and-play and speed up the development process, which is Shopify's core value proposition.
Google began testing adding “Strongest Match” or “Strong Match” badges on some search ads in the U.S. to help users spot the most relevant results and help advertisers reach high-intent audiences, according to a LinkedIn post by Google Ads liaison Ginny Marvin. The badges get applied to existing search ads using Google's current ad-quality and relevance signals, and have no impact on the auction or how ads rank. The test is running for a small share of U.S. users as Google assesses the value of the badges on users' decision making. Advertisers and agency owners pressed Marvin in the comments on what exactly drives the label, such as whether it's based on the keyword-based quality score, ad or landing page relevance, or only based on the ad itself. Like any ranking or quality factor that Google publishes, people want to know how to manipulate it.
Cloudflare unveiled PACT, a privacy-preserving protocol built to standardize how AI agents interact with websites by proving a human is in the loop, letting legitimate agents through while locking out abusive bots, with Google Chrome, Microsoft Edge, Mozilla Firefox, and Shopify signed on as participants. Shopify's Ilya Grigorik pitched PACT as a way for merchants to distinguish real shoppers and authorized agents from abusive traffic without subjecting buyers to friction or invasive tracking, arguing every extra challenge or false positive risks turning a purchase into an abandoned cart. Private Access Control Tokens would let sites with strong knowledge of “personhood” issue anonymous tokens a browser can present elsewhere to prove a human is involved, without enabling tracking. The protocol, which aims to position Cloudflare's infrastructure at the center of agentic-web trust, isn't rolling out yet and has no announced timeline. It seems like we're moving towards a world where “companies that don't play by our rules” could be labeled “abusive” by leading tech companies that write the rulebook, leading to even further consolidation in the already-concentrated web-infrastructure space.
eBay will stop selling its own digital gift cards in August, with physical cards phasing out at retailers like CVS and Walgreens as inventory sells through, according to Value Added Resource. Existing eBay gift cards will stay valid with no expiration and can still be used at checkout, and the move applies only to eBay-issued cards, with third-party gift card listings on the marketplace unaffected. eBay says it decided to stop selling the cards to “focus on other ways to support customers,” without addressing whether fraud, financial reporting, or a payments-strategy shift drove the decision. The change also removes a marketing lever eBay has used before, such as when it offered a 10% gift-card discount last year to juice Q2 GMV and revenue numbers.
Sam Altman's personal investment portfolio is benefiting tremendously as OpenAI strikes business deals with companies he holds stakes in, with at least 10 Altman-linked startups having done or discussed deals with the AI firm, according to The Wall Street Journal. His stake in fusion startup Helion more than doubled to at least $4.1B after OpenAI signed a power agreement and a major OpenAI investor backed Helion at a $15.5B valuation, while OpenAI's deal to buy chips from Cerebras, a company he's partially-owned for over a decade, helped fuel an IPO that boosted his stake more than sixfold. Altman holds no direct OpenAI equity, which is something he used to boast made him uniquely unbiased and a better steward to lead the company towards public good. However, all it really did was push his financial incentives outside the company he runs to a web of investment holdings that OpenAI’s board claims to monitor for conflicts of interest — though not carefully enough if you ask me. The inner-dealings have drawn a House Oversight probe and calls from several attorneys general for an SEC review ahead of OpenAI's planned IPO.
Google added an order-tracking feature to Google Wallet for U.S. users that reads digital receipts, carrier tracking numbers, and shipping status out of Gmail to surface upcoming deliveries on the app's homescreen alongside payment methods. Rather than running a separate tracking system, the feature taps directly into a user's inbox, requiring Google Workspace smart features to be turned on in Gmail settings, with a “View more” button opening a more detailed view of packages in transit. Google also upgraded Chrome Autofill on Android and iOS to pull a wider range of information directly from Google Wallet including travel details, loyalty cards, vehicle registration, and other credentials users would otherwise need to type by hand. The moves are part of Google's push to turn Wallet into a daily dashboard beyond cards and tickets.
Amazon is testing a program called Right Station Link that puts wearable devices on workers in “indirect” warehouse roles, such as equipment maintenance, safety, and floor management, to log when they reach a station and how long they stay, according to Business Insider. Because these workers move between assignments all shift rather than staying at one packing station, Amazon previously had no automatic way to verify their location, which must have been torture for upper management. Internal documents pitch the devices as ways to “improve labor tracking accuracy” and “reduce non-productive labor hours” across roles tied to roughly $2.8B in labor spend. Amazon planned to use Zebra hand-worn scanners but is making the software hardware-agnostic after warnings that device-delivery delays could threaten a holiday-peak rollout, leaving the door open for butt-injected devices at any point in the future. Amazon disputed the report, calling the $2.8B a “theoretical modeled opportunity” rather than waste and saying the system doesn't measure individual productivity or track workers' real-time movements.
Kroger's retail media unit, Kroger Precision Marketing, is working with TikTok to let advertisers target the grocer's shoppers using purchase data through TikTok's self-service advertising system. By identifying its shoppers on TikTok, Kroger says advertisers can influence them from product discovery through purchase and keep brands top of mind. The arrangement follows a March collaboration with Google that brought Kroger's shopper analytics to YouTube ad targeting, with Kroger claiming that households that engage with social content spend twice as much as its average customer. In a company survey, over two-thirds of Kroger shoppers said a social post had driven them to purchase at least one item across groceries, household goods, or personal care in the last six months. OMG you guys will buy anything! And now, a word from our sponsors…
Amazon must collectively bargain with unionized workers at a San Francisco delivery center, according to an NLRB judge who ruled that the company broke federal law by refusing to recognize the union after it won majority support among employees in 2024. It's wild to me that Amazon leadership will include bylines like “he/him/his” in their e-mail signatures, while simultaneously refusing to recognize workers that identify as union members. “Us/we/ours” is the new signature! The ruling marks one of the few times Amazon has been ordered to bargain with U.S. workers, though it's unlikely to lead to actual bargaining, as it relies on a Biden-era NLRB precedent that Amazon is pushing to have overturned.
Talent agencies are increasingly training creators to act like retailers, helping them set up e-commerce stores, prep for major online sales events, and prove to brands that their audiences actually spend money, according to Modern Retail. Income from product sales and affiliate marketing now accounts for 21.2% of total creator income, prompting agencies like Underscore Talent to hire commerce specialists and push roughly 80% of their roster onto Amazon storefronts, which have become a prerequisite for some brand deals. Agencies are now running detailed Prime Day playbooks, coaching clients months ahead on which products to spotlight and using affiliate-performance data to land longer deals and push back on lowball offers. The trend rewards conversion over reach, with creators like Lexi Rosenstein, who has around 150,000 followers but drives $300K-$600K in monthly GMV, building retailer-style businesses around bundles, merchandising, and pricing.
Shopify is banning the sale of vape products across its U.S. platform after a coalition of 25 state attorneys general pushed the company to crack down on unlicensed e-cigarettes sold online. The attorneys general singled out Shopify in an effort to curb illegal vapes, usually made in China, that remain widely available in the U.S. despite being illegal to import or sell, with the broader illegal market estimated at $9B. The ban will apply to all vapes and related products regardless of whether they hold regulatory authorization, though it's unclear whether it extends beyond the United States. As a self-admitted conspiracist, I'm also curious if Big Tobacco lobbying had anything to do with the collaborative campaign by half the country's attorneys general.
Google will begin rolling out lower Play Store fees and external payment options on June 30 for developers in Europe, the UK, and the US, as agreed in its Epic Games settlement. The new structure splits commissions into billing and service fees, with a flat 10% service fee on the first $1M a developer earns each year, rising to as much as 25% above that, while apps installed after June 30 top out at 20%. Developers will also finally be able to route users to an outside checkout through a Google-approved payment provider, avoiding the 5% billing fee while still paying the service fee. The changes expand to Australia in September and Japan and Korea by year-end, with a global rollout set for 2027.
Salesforce launched Help Agent, a prebuilt AI customer-service agent on its Agentforce platform that companies can connect to their knowledge, actions, and channels like web, text, and voice using a low-code builder. The company is employing a new pay-per-resolution pricing model for the agent, charging a flat $2 fee only when the agent resolves an issue autonomously start to finish, a shift from its existing per-conversation billing that charged whenever an agent engaged, including on cases that were escalated to a human. Executives pitched it as tying spend to outcomes business users already understand, arguing consuming a token alone doesn't guarantee a return. The agent ships alongside a redesigned Customer Service Portal built around a single conversation bar, with both generally available in July 2026.
In other Salesforce news… The company shipped a major Agentforce Commerce update, making three AI selling agents including Shopper Agent, Buyer Agent, and Merchant Agent generally available to all customers. On the B2B side, Buyer Agent handles procurement inside WhatsApp and SMS, letting a customer text a reorder request and get back SKU confirmation, contract pricing, and a completed order without a portal or login. Merchant Agent organizes catalogs and tunes search rankings through plain language, while B2C Shopper Agent runs the shopper relationship from first browse to checkout and into service. Native integrations that surface sellers' catalogs inside ChatGPT, Google Search with AI Mode, and the Gemini app are arriving this summer, with the retailer staying merchant of record rather than handing the transaction to the AI platform.
Wix released its first State of Websites report, drawing on its user base to chart how AI is reshaping how sites get built, found, and turned into revenue. The average time to publish a website fell 50% between 2025 and 2026, from eight days to four, with e-commerce sites cutting build time in half and beauty and wellness sites cutting build time 55%, though Wix says most users of its AI builder still manually edit the details that include their branding, like text and images. On discovery, Wix reports AI platforms now ping nearly 700K of its sites monthly, totaling 2.2M sessions in March, but LLMs still drive under 1% of site traffic, with search leading traffic acquisition at 42%. The report notes that structured data keeps sites visible to AI agents while custom domains prove legitimacy, advice which feels like it could've been in a State of Websites report from 15 years ago too.
Meta is walking back its decision to force engineers onto an AI-training task force, telling those it reassigned that it will now “defer to each individual's choice” on whether to stay, according to an internal memo obtained by Business Insider. Last month the company moved 7,000 employees into units like the Applied AI task force to help train its coming models, which drew backlash from staff who compared the work to data labeling, with some calling the reassignment a “draft” and the reversal an “undraft.” The move follows CTO Andrew Bosworth telling staff that morale is among the worst in Meta's 20-year history, after the company laid off 8,000 people in May.
Illinois Governor JB Pritzker signed and officially brought into law the state's new Buy Now Pay Later Loan Consumer Protection Act, requiring BNPL providers to register with the state, disclose what a loan costs, and check whether a borrower can afford to repay. I first reported on the new law last week when it was pending approval. The law, which mirrors a BNPL measure New York passed last year, takes effect immediately and gives providers until January 1, 2028 to comply. Pritzker signed it alongside a Junk Fee Ban Act targeting undisclosed charges like resort and delivery fees, days after Illinois enacted a Digital Asset Tax Act levying a 0.2% tax on crypto transfers. My prediction is that more state laws like this are on the horizon across the U.S.
In lawsuits this week…
- YouTube settled a social media addiction case brought by a Florida teen who alleged that the company had designed its platform to be addictive. He's also suing Meta, TikTok, and Snap in a trial set to begin on July 27 in Los Angeles.
- Sarah Wynn-Williams, a former Facebook policy executive, is suing Meta over the arbitration action it used to bar her for more than a year from promoting her memoir “Careless People,” which alleges wrongdoing by Facebook executives. (FYI – It was my best read of 2025.) She is asking the court to lift the arbitration order, void her 2017 severance agreement and its non-disparagement clause, and award damages for lost book sales and speaking fees.
- Publishers behind nearly 400 local and regional newspapers are suing OpenAI and Microsoft for copyright infringement, alleging the companies copied their reporting to train ChatGPT and Microsoft Copilot without permission or payment, in what the plaintiffs' law firm calls the largest coordinated challenge by local papers. Beyond the copyright claim, the suit alleges OpenAI stripped copyright management information like bylines and copyright notices from the articles, violating the Digital Millennium Copyright Act.
- Speaking of suing OpenAI and Microsoft… New York Times asked a court to amend its copyright complaint against the companies, alleging Microsoft drove OpenAI to copy its journalism by custom-building a supercomputer to enable infringement by weighing its articles heavily so models could mimic high-quality journalism, a claim Microsoft dismissed as a last-ditch effort to escape unfavorable precedent. The motion comes after the Supreme Court sided with Cox Communications in a case where Sony claimed the company was contributing to music piracy as an Internet service provider, which set a new precedent in which plaintiffs now have to prove that parties intentionally acted to induce illegal conduct (ie: building a special supercomputer). OpenAI still defends that training on publicly available data is fair use, which is a question courts have yet to settle.
In corporate shakeups this week…
- Meta named Cred founder Kunal Shah as its new global head of WhatsApp, replacing Will Cathcart after a seven-year run, alongside a $900M investment in the Indian fintech that hands Meta a roughly 20% stake as it makes another push into India's payments market.
- Google DeepMind has lost six named researchers to Meta, OpenAI, and Anthropic since February, including reasoning pioneer Denny Zhou, whose quiet move to Meta only recently surfaced after he changed his job title on LinkedIn.
- Google is reorganizing its new AI coding strike team to chase Anthropic in the AI coding market, shifting toward a “midtraining” approach and expanding into tasks like building presentations. The move comes after coding emerged as a major weakness for Google, which originally bet its strongest base model would master it on its own.
- Apple's Vision Pro and smart-glasses chief Paul Meade is leaving for OpenAI's hardware team, where he'll work on its family of AI-powered devices. Bloomberg's Mark Gurman ties the exit to a hardware-engineering reshuffle around John Ternus's elevation to CEO that reportedly left several Apple VPs feeling demoted.
- Meta Superintelligence Labs poached three co-founders and team members from AI security startup Virtue AI to bolster its safety work on AI agents, continuing Meta's pattern of acqui-hiring teams rather than buying whole companies.
Google is testing a button within its AI Overview in Search that sends users to a web-only results tab, which strips out AI search summaries in favor of showing plain web links. The feature was spotted by Sachin Patel, who posted screenshots showing an AI Overview with a button that, when clicked, drops the user into the web tab. Do users hate AI Overviews so much that Google is having to build an escape hatch back to traditional search results? I think the best move would be abandoning the “I'm Feeling Lucky” button for an “Ask Gemini” button (which is pretty much the same thing, given how you're lucky to get an accurate answer out of Gemini, LOL), while keeping a second “Search Google” button to surface traditional link results. From there, users can decide whether their default search after hitting “Enter” takes them to AI summaries or search results.
Anthropic launched Claude Tag, an AI agent that sits inside group Slack chats and handles coding, analytics, file search, and thread tracking, putting it in direct competition with Slackbot, the rival agent sold by Salesforce (which owns Slack). Some Salesforce staff and partners were unsettled that the company promoted a product competing with its own, according to The Information, with several employees privately comparing Claude Tag to a Trojan horse that hands Anthropic context on how customers operate. Anthropic's terms say it doesn't train on data from commercial customers, and Salesforce CEO Marc Benioff framed the product as a partnership rather than a threat, but still… The way major SaaS platforms have embraced frontier AI models, inviting them into their homes to have dinner with their wives, reminds me of when major retailers like Toys R' Us partnered with Amazon to power their e-commerce logistics — a move that didn't end well.
Amazon is planning to expand its Amazon Now quick-commerce service to more than 300 cities across India, building what it claims is the country's largest delivery-in-minutes network. Walmart isn't standing idly by while Amazon eats its chicken masala though. Flipkart, which is majority-owned by Walmart, says it's planning to add 500 more neighborhood warehouses across the country, with a focus on smaller cities. To which Amazon said, “I'll see your 500 and raise you to 700!” — and eventually there was one quick-commerce warehouse for every Indian. At some point, these companies can just start stocking people's pantries and charging them for removing the food like a Las Vegas minifridge. The move comes as Flipkart prepares for its Mumbai public listing, though a timeline has not yet been set.
JD.com founder Richard Liu said the Chinese e-commerce giant plans to “white-collarize” its 700K blue-collar workers, including delivery riders, retraining them for office-based roles repairing and maintaining the robots that will take over manual delivery, according to Business Insider. Speaking at the APEC CEO forum, Liu said JD.com has signed contracts with 120 schools across China to retrain workers and pledged it won't fire anyone whose job gets automated, and will instead reassign them. He also called for an internationally recognized protocol governing AI and robot adoption, arguing robots shouldn't deprive people of the right to work. Meanwhile in the U.S., Amazon and Meta are like, “Would you shut the fuck up Liu!” – as to not give their staff any ideas.
🏆 This week's most ridiculous story… REI got roasted over its Instagram ad showing a bike with two sets of handlebars, with one Reddit post calling it “AI slop” and questioning the retailer's environmental commitments. REI blamed Meta's AI personalization tool, claiming that Meta “auto-enrolled” it in the feature, which produced an inaccurate alteration of a vendor-provided image, and that it has since unenrolled. Van Rysel, the bike brand featured in the ad, confirmed that the original image came from its own photoshoot and that it made no AI enhancements to it. The story is believable, as REI isn't the first advertiser to report being opted in by default to Meta's AI tools and subsequently having them produce bizarre ads. The ridiculous part is that Meta is still doing it!
10. Seed rounds, IPOs, & acquisitions
Walmart agreed to acquire Vibe.co, a self-serve connected TV ad platform that lets SMBs run hyper-targeted streaming TV campaigns, for an undisclosed amount reported to be north of $1B. Vibe, which bills itself as “the Google Ads of streaming” and hit $100M in ARR last year, gives Walmart Connect access to more than 10,000 SMB and mid-market advertisers it can pair with the retailer's commerce data and closed-loop measurement to drive ad dollars. The deal builds on Walmart's earlier $2.3B Vizio purchase and recent integrations with Magnite, Google DV360, and Yahoo as it pushes deeper into retail media and CTV.
Onward, a post-purchase platform for Shopify brands covering returns, order tracking, order editing, claims management, and customer intelligence, acquired Inveterate, a loyalty and membership platform that powers programs through store credit and cashback rather than points, for an undisclosed amount. Onward plans to feed loyalty into a single cashback program across its full stack, arguing that “everyone understands what $10 means” and that the model's simplicity drives higher redemption than point-based programs, which it pegs at 2-3% versus cashback's 8-12%. The company is making Inveterate's loyalty solution free for brands already using its Checkout+ order-upgrade product, with plans to fold its membership tooling into Onward's broader retention ecosystem.
Redo, a platform that helps brands manage the post-purchase journey with tools for order tracking, package protection, fulfillment, customer service, and marketing, raised $81M in a Series B round led by Smash Capital at a $1.25B valuation. CEO Sterling Snow pitched the raise as funding Redo's shift from solving returns to helping merchants own the full customer relationship across every touchpoint. The company has already deployed part of the capital to acquire ReturnBear, an international returns provider with fulfillment across more than 100 countries that lets customers return products locally for inspection, refurbishment, and reshipping.
OpenAI is leaning toward delaying its IPO until 2027, with advisers pushing CEO Sam Altman to slow down after SpaceX's stock slid over 30% from its post-IPO high, raising doubts about retail demand, according to The New York Times. Advisers offered Altman a choice of waiting for a true $1T valuation or lowering the target for a faster listing, which Altman called a nonstarter. OpenAI reported roughly $13B in 2025 revenue and hopes to triple it this year, even as it keeps spending on data centers and sees ChatGPT downloads plateau near 900M, below the billion investors hoped. News of the delayed IPO sent SoftBank's shares plummeting by 13%, as a result of how heavily invested the company is in OpenAI.
Wayflyer, a lender that offers revenue-based financing to e-commerce brands, acquired Conjura, an AI analytics platform that consolidates merchants' fragmented commerce, marketing, and operations data into a single view and layers predictive models on top for growth and margin insights, for an undisclosed amount. Wayflyer was originally incubated within Conjura in 2019 before spinning out, and now the two companies are joining forces again, with all of Conjura's employees joining the combined company. The deal advances Wayflyer's AI product roadmap by adding tools like Conjura's recently added natural-language interface that lets merchants query complex datasets in plain English.
Google invested roughly $75M in A24, an independent American film and television studio known for producing director-driven movies like Marty Supreme and Backrooms, as part of an AI research partnership that pairs the studio with its DeepMind unit to build filmmaking tools. The deal gives A24 access to DeepMind's research and infrastructure, with researchers helping develop new workflows like AI-generated storyboards, while keeping Google out of A24's content library and data. A24 partner Scott Belsky framed the relationship as different from rival AI deals that pitched faster, cheaper filmmaking, arguing these tools preserve creative control and won't resemble the prompted generation that makes people uncomfortable. After receiving backlash from the industry, A24 defended the partnership saying, “We'd rather have a seat at the table than on the sidelines.”
MoEngage, an AI customer engagement and marketing automation platform that helps consumer brands personalize and orchestrate messaging across channels, acquired Aampe, an agentic AI infrastructure company that assigns a dedicated, autonomous AI agent to every individual customer of a brand to personalize messages, for an undisclosed amount reportedly in the tens of millions. The deal advances MoEngage's push toward an agentic customer-engagement platform, building on its Merlin AI agents, as the company prepares for a public listing after recently moving its parent company's legal domicile from the U.S. back to India. Founders Paul Meinshausen, Schaun Wheeler, and Sami Abboud will join MoEngage to lead its agentic-decisioning work, with Aampe customers like Grab and Taxfix moving over and Swiggy already using both platforms.
AppsFlyer, an ad measurement and attribution company that helps brands optimize their marketing campaigns across mobile, web, and connected TV, raised $1B in a Series E round from Moloco, Google, Meta, and Unity at a $2.7B valuation. Each investment is minority, non-controlling, and non-exclusive, with the company stressing that no backer gets preferential treatment on its APIs, measurement signals, or attribution logic, and that customers still control which partners they share data with. CEO Oren Kaniel framed the deal around keeping measurement independent and neutral as AI takes over more of how advertising gets bought and optimized, arguing the industry benefits from signals not shaped by any single market participant.
Menlo Ventures, a Silicon Valley-based venture capital firm that backs early and growth stage startups, raised $3B in fresh capital, marking the largest haul in its 50-year history. The firm previously led Anthropic's 2024 Series D round with a $750M investment that is now worth roughly $14B, according to Bloomberg. The fund will back AI startups across infrastructure, models, and applications, with Menlo pushing into larger later-stage deals like its Anthropic bet as top AI companies stay private longer.
Orderful, an AI-native EDI platform that helps companies connect and onboard trading partners, raised $35M in a Series C round co-led by Koch Disruptive Technologies and NewRoad Capital, bringing its total amount raised to $85M. The platform replaces the manual mapping work typically involved in global trade by reading each trading partner's specification document and generating compliant maps that update themselves as requirements change. The approach aims to make obsolete the legacy EDI model, where providers typically charge recurring service fees to manage integration complexity by hand, a fee structure which Orderful says never actually addresses solving the complexity issue itself.
Solute, the German company behind price-comparison portals like billiger.de, acquired repricing.com and datafeedmanager.com from AdValue for undisclosed amounts. Repricing.com handles automated price optimization, analyzing competitor and market data in real time to adjust prices across marketplaces and shops by rule, while datafeedmanager.com structures and optimizes product-data feeds for use across channels. The deal expands solute's B2B tooling for online retailers, aiming to close the gap between data-feed structuring and data-driven pricing to give retailers a more complete ecosystem alongside solute's existing reach and visibility solutions.
JustAI, an AI marketing platform that automates personalization, experimentation, and campaign decisioning for enterprises, raised over $17M in a Series A round led by Base10. The platform is powered by proprietary reinforcement learning models that predict the next best action or message for users, aiming to replace traditional rules-based campaigns with AI-driven decisioning. JustAI plans to use the capital to expand engineering and go-to-market teams, strengthen its agentic infrastructure, and extend the platform deeper into e-commerce and B2B use cases.
Revora, a Saudi Arabia-based AI commerce platform formerly known as MyAlice, raised $2M in a seed round co-led by i2i Ventures and Oraseya Capital, bringing its total amount raised to $2.5M. The platform's AI agents recommend products, recover carts, and take payment inside the conversation across WhatsApp, Instagram, and merchants' own storefronts, placing real orders inside platforms like Salla, Zid, and Shopify, while turning each merchant's catalog into structured data built for AI-powered discovery. Co-founder Shuvo Rahman said, “We're building Revora on one bet: that the businesses winning the next decade are the ones an AI can understand, represent, and sell for.”
Mirendil, a San Francisco-based startup building AI that automates AI research itself so outsiders can develop specialized models in fields like medicine and materials, raised $200M in seed funding at a $1B valuation from Andreessen Horowitz, Kleiner Perkins, and Nvidia. The company was founded by former Anthropic researchers Behnam Neyshabur, who led scientific AI reasoning at Anthropic and spent over five years at Google DeepMind, and Harsh Mehta, who built the first version of Anthropic's internal autoresearch platform, joined by Shayan Salehian, an early xAI engineer, and Tara Rezaei, an MIT graduate and former OpenAI researcher. Mirendil targets a gap left by frontier labs, which use AI to speed their own research but bar outsiders from using their tools to compete, by putting that same self-improving research capability in outsiders' hands.
Airwallex, a cross-border payments and financial infrastructure company that helps businesses move money internationally and manage global accounts, FX, cards, and treasury, raised $320M in a Series H round led by Addition, lifting its valuation to $11B from $8B in December. The funds will be used to further develop two new AI products including T:0, a solution that automates bookkeeping, forecasting, taxes, compliance, and reporting, and Airi, an agentic consumer wallet that aims to offer delegated agent payments, spend limits, and permission controls. CEO Jack Zhang predicts that AI will collapse a crowded field of fintech categories into a handful of platform winners, with agentic payments and autonomous finance as the next battleground.
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PS: Working at Microsoft has given me a new outlook, and I learned to work well in teams.