Hi Shopifreaks

I've got a big edition today jam-packed with stories about AI commerce -- what it could've been, and what it actually is in 2026. Is agentic commerce a solution looking for a problem? Or was OpenAI simply too early with Instant Checkout? I'd love to hear your thoughts. Please know that you can hit reply to any of my e-mails to share your opinions, and I read every reply!

In this week's edition I cover:

• OpenAI steps back from commerce
• Meta tests AI shopping research
• Amazon wants to sell ads in chatbots
• OpenAI partners with Criteo and maybe The Trade Desk to sell ads
• Anthropic is launching a marketplace for AI software
• Google wants to replace your product page
• Google lowers its 30% Android app store fee
• Apple may host Siri on Google servers
• Stripe is testing a payment tool for LLM usage
• Walmart now allows free samples for reviews
• OpenAI is developing a GitHub alternative
• Meta contractors can view your intimate moments

All this and more in this week's 268th Edition of Shopifreaks. Thanks for subscribing and sharing!

PS: Have you been enjoying Shopifreaks? If so, I'd appreciate if you took a moment to write a Google Review. 

Stat of the Week

It would cost each of America's 135 million households roughly $67 per year to subsidize the United States Postal Service's $9 billion annual deficit. This is roughly 10% of what each household pays in taxes to support U.S. military and defense spending. Subsidizing the postal service with taxpayer dollars could help keep the cost of postage lower for the 3.5 million e-commerce businesses and 9 million marketplace sellers that directly depend on USPS for delivery, while continuing to provide stable local jobs for postal service workers.

1. OpenAI scales back its integrated commerce plans

OpenAI is scaling back its plans to introduce shopping directly inside the general ChatGPT chatbot, pivoting instead to a focus on having checkouts take place inside of specific apps within its interface. Shoppers will now either need to pay through a retailer's app or be redirected to their website to complete purchase. 

OpenAI initially launched Instant Checkout in October 2025 in partnership with Etsy and Walmart, and then slowly added a handful of Shopify merchants, with plans to take a cut of transactions that were completed through ChatGPT. However after the initial hype subsided, there were signs that the initiative was slowing, including as recently as February when it was revealed that OpenAI hadn't yet set up systems to collect and remit state sales taxes. 

An OpenAI spokesperson told The Information:

"We’re evolving how we approach commerce in ChatGPT to better meet merchants and users where they are. Instant Checkout is moving to Apps, where purchases can happen more seamlessly. We appreciate our partners for learning with us and look forward to sharing more as we continue building in this area."

That's okay, right? I'm sure the 9 people who ever used Instant Checkout for a single purchase will move on. If they had to choose, they'd probably rather have GPT-4 back anyway. 

The reality of e-commerce in 2026 is that 50% of U.S. sales happen on Amazon and Shopify, as we learned a couple of weeks ago, and checkout on either platform couldn't be any easier or faster for consumers. Instant Checkout was a solution looking for a problem, without the infrastructure in place to actually solve it. 

AI "progress" needs to slow the fuck down. The capabilities aren't keeping up with the hype, especially in OpenAI's case. However it can't slow down because investors have overextended their bets and want to see returns, so we'll continue to see unfinished, untested, poorly designed products hit the market too soon in search of a userbase that is mostly happy using AI to search for things and edit their photos. 

We've officially entered the "AI is not as good as we said / thought" year. And on that note, if you can't even handle e-commerce checkout, you should NOT be dabbling in health or military.

2. Meta tests a shopping research feature inside of its chatbot

Speaking of AI shopping... Meta is testing a shopping research feature inside of its AI chatbot, enabling users to search for product recommendations and receive a carousel of product images that include captions with information about the brand, website, and price. Meta also offers a brief explanation of its recommendations as a bullet-list below the carousel. 

The recommendations are personalized to each shopper, based on the obscene amount of information that Meta has on its users, including their gender and location. For example, when asked to find puffer jackets, Meta AI's response referenced the author's location in New York and offered options for women's puffers. 

Bloomberg notes that there is no checkout or payment option within the chatbot, but users can click on the product links to view the item on the merchant's website.

As we learned from OpenAI's experience with agentic commerce, Meta isn't missing out on anything by not offering it!

Checkout is a low margin game. Advertising is where the profits are at, and that's what Meta excels at. It appears that they are developing a shopping discovery tool that can cater to the trove of data they have on their users to personalize results, as opposed to attempting to control the whole purchase flow. Seems a lot more manageable, while fitting in perfectly with Meta's existing business model.

It's actually surprising that Meta hasn't offered a more robust product search for the past decade, long before AI and agentic commerce were household names. When Meta launched Facebook Marketplace in 2016, it was the perfect opportunity to build a product search and recommendation engine that intermixed Marketplace results with products from the web, while cementing Facebook as destination for product discovery. No time like the present though.

3. Amazon explores tech to sell ads within third-party AI chatbots

Amazon is exploring technology that would help other apps and websites sell ads within AI chatbots, according to The Information sources who spoke to the company about its plans.

Sources said that in recent months, Amazon Publisher Services, which is the division of its ad business that helps websites run ad auctions, has held discussions with some websites and outside firms about how it could work with them to power chatbot ads, similar to how it currently serves as a middleman between retailers and publishers via its demand-side platform. Amazon employees pitching the idea have pointed to Pinterest as a potential user of such a technology.

Recently publishers, websites, and apps like Yahoo, Time, Yelp, Forbes, and ESPN have introduced their own chatbots on their sites, creating new real estate where Amazon Ads could potentially live. And given how expensive it would be to create such an offering in-house, and the expertise required to do so, I can see the appeal of employing Amazon to do the heavy lifting.

Of course, most of the chatbots mentioned above are powered by major LLM providers, including Google and OpenAI, which could very well offer their own revenue-sharing ad integration in the future. Amazon will likely have some competition in the space, but they're smart to get an early start.

It's interesting that the industry is essentially looking at AI chatbots as just another channel to insert advertising, and the spoils may inevitably go to the victor who owns the advertiser relationships. More examples below in story #4.

4. OpenAI looks to third-party ad tech firms to sell ChatGPT ads

OpenAI partnered with Criteo to sell its chatbot ads, according to a public announcement, and is in talks with The Trade Desk to do the same, according to sources.

Criteo CEO Michael Komasinski said in a statement:

"[The deal] represents an exciting step forward in advancing advertising in an emerging AI experience. We are helping shape how advertising can support discovery and consideration within large language model platforms, grounded in experiences that are additive, relevant, and built on user trust."

Adweek reports that Criteo's integration will roll out in the coming weeks.

Meanwhile, OpenAI has also held early talks with The Trade Desk to sell its ads, according to The Information sources. No wonder Jeff Green bought $150M worth of company stock! More on that in Section #10.

OpenAI says that it plans on eventually building its ad tech functions in-house, putting it more in line with Meta, Google, and Amazon, but I feel like I've been hearing that story for a long time now. Perhaps it's a smarter, safer route to work with existing ad networks to automate sales and provide performance metrics to buyers. It's a faster go-to-market strategy.

Sources say that OpenAI is also talking to other media agencies and ad tech firms to sell its ads, in addition to Criteo and The Trade Desk. I wonder if Amazon will get a seat at the table, given its recent $15B investment in the company and $35B more on the way.

5. Anthropic is launching a marketplace for AI software

Anthropic is launching a new marketplace for its corporate customers to purchase third-party software applications that use its LLMs, with options initially including services from Snowflake, Harvey, and Replit.

The company announced: 

"Find and install plugins from marketplaces to extend Claude Code with new commands, agents, and capabilities. Plugins extend Claude Code with skills, agents, hooks, and MCP servers. Plugin marketplaces are catalogs that help you discover and install these extensions without building them yourself."

First users add the marketplace itself to register the catalog with Claude Code so they can browse what's available. Next they can browse the catalog and install individual plugins, similar to adding an app from an app store.

Anthropic does not plan on taking a cut of the purchases and will allow its customers to use some of their committed annual spending on its own services toward these third-party tools, which makes sense given that some of the money will eventually flow back to Anthropic via token usage. 

Despite the company's recent friction with the Pentagon, Anthropic believes that the government restrictions won't affect its business that's unrelated to specific Pentagon contracts. 

Anthropic’s head of Americas Kate Jensen said:

"This is something we’re talking a lot with our customers about. The good news here is, for the most part, we expect that it will be business as usual for the vast majority of our customers."

6. Google issued a patent for creating AI-generated product landing pages

Google was issued a patent that describes a system that automatically generates personalized landing pages in place of a brand's own website when its algorithm determines that the existing page is a poor match for the user's search intent. The feature primarily targets e-commerce and paid advertising use cases, with all examples pointing to shopping pages, product feeds, conversion rates, and sponsored content rather than editorial or informational sites. (Meaning it's not going to recreate your blog... yet.)

Here's how it works: 

• The system calculates a "landing page score" for the brand's existing website, evaluating how well the page meets the user's specific needs.
• If the webpage is deemed insufficient, the system triggers an AI generation of a better landing page, leveraging the user's search context, location, and past preferences to pull data from the organization's site and repackage it into what it considers to be a more intuitive UI.
• The user sees an updated search results page with a link leading to the AI-generated page instead of the brand's URL.

Ah okay, so an AI-generated page that Google can serve more ads on? Sounds about right. 

Imagine a landing page that displays the specific product's information at the top, followed by a grid of sponsored shopping results for similar products. That's undoubtedly where this is headed. 

Of course, it would also provide an additional channel for Google to own the transaction through its new Universal Commerce Protocol, effectively turning Google into the world's biggest e-commerce marketplace that merchants never signed up to sell on.

The patent, numbered US12536233B1 and titled "AI-generated content page tailored to a specific user," was submitted on July 25, 2024 (a lifetime ago in AI years) and granted on January 27, 2026. A parallel European application was filed on July 25, 2025.

7. Google lowers its 30% Android app store fee in the US, UK, and EU

Google is lowering its Android app store fees in the US, UK, and EU to 20% or less, down from 30%, by June 30th, as well as making other major changes to its app store policies following a jointly proposed settlement with Epic Games this past November. While the settlement is still pending approval by the courts, Google has decided to go ahead with the changes.

Here's what's changing: 

• Google is launching a "Registered App Stores" program outside of the US so that users can download and install third-party app stores, like the Epic Games Store, from the web without any headache. Google will not charge developers ongoing fees on purchases made through those stores, only a one-time registration fee of a few hundred dollars.
• Within the US, a court had previously ordered Google to adopt a store-within-a-store model, requiring the company to carry rival app stores within its own Play Store. Google is currently asking the judge to let it substitute its Registered App Stores program instead, but that remains to be determined.
• App developers will now be able to offer their own billing systems alongside Google Play's billing for in-app purchases, which in practice means that Google is separating its billing fees from its service fees in calculations.
• Under the new structure, Google will keep 25% when you pay for content inside an app you've already purchased, while charging $2-4 or 20% if you follow a link to download or buy the content elsewhere.
• To accommodate these changes to its billing structure, Google will be mandating APIs outside the US so that it can get its cut when you click out to an app developer's website and pay for the purchase there.

Great changes I guess, but also still a stinky, steaming pile of bullshit.

Can you imagine if Microsoft dictated what software we can or cannot install on our Windows devices? Or if they charged software developers a 30% (or 20% or 5% or whatever amount) fee on purchases made within that software?

How is it that Google and Apple can get away with such blatantly anticompetitive practices within their app marketplaces?

The mobile operating ecosystem is in desperate need of a 3rd major player that bypasses these greedy, competition-stomping gatekeepers -- and frankly, Samsung should be the one to build it. But that's a topic for a different day. 

Wait, there's more! And it's not so epic...

As part of the settlement, Epic Games CEO Tim Sweeney, who has historically been one of the most vocal critics of Google's app store practices, has agreed to not only stop criticizing the company's app distribution policies and fees, but to actively advocate that Google and Android are "procompetitive and a model for app store operations."

The term sheet also restricts Sweeney from pushing for further changes to Google's app store policies, requires him to make good faith public statements supportive of the deal, and may obligate him to defend the agreement in courts around the world. The restrictions are tied to Google's timeline for implementing fee changes, which are expected to be complete by September 2027 at the latest, meaning Sweeney may not be free to criticize Google's app store until September 2032. 

8. Apple may host Siri on Google servers instead of its own

Apple entered discussions with Google to host an upcoming version of Siri on Google's data center servers with strict privacy standards, potentially moving away from its original plans to host the Gemini models on its own infrastructure. The arrangement would further deepen Apple's reliance on Google, which already provides cloud capacity for iCloud storage and the training of Apple's in-house AI models.

Former Apple employees told The Information that the company has historically mismanaged its cloud infrastructure and that only 10% of Apple's Private Cloud compute capacity is in use on average, with some servers still sitting in warehouses uninstalled.

Although various leaders at the company have attempted to build up its internal infrastructure to reduce reliance on Google Cloud and Amazon Web Services, those efforts have been unable to get past finance executives, who look at cloud computing as a cost center rather than an investment. Sources said that Apple's resistance to making big investments in its own infrastructure has led to ongoing departures of cloud experts from the company. 

Personally I don't blame Apple for not aggressively investing in cloud infrastructure right now, as they'll probably be able to buy it for pennies on the dollar in a few years from bankrupt AI startups and/or cheaper alternatives that flood the market. No need to pay Nvidia's $4 trillion market cap prices for chips. 

I'm also not convinced that Apple has given up on AI or that it will indefinitely depend on third-party providers like Google or OpenAI to power Siri.

A few months ago, Jeremy Kahn and Beatrice Nolan of Fortune said it well: 

"Apple defenders note that the company is rarely a first mover in new technology. It was not the first to create an MP3 player, a smartphone, wireless earphones, or a smartwatch, yet it came from behind to dominate many of those product categories with a combination of design innovation and savvy marketing. And Apple has a history of learning from partners for key technology, such as chips, before ultimately bringing these efforts in-house. Or, in the case of internet search, Apple simply partnered with Google for the long term, using the Google engine to handle search queries in its Safari browser. The fact that Apple never developed its own search engine has not hurt its growth. Could the same principle hold true for AI?"

Time will tell. In the meantime, "Hey Google"... Oops, I mean, "Hey Siri."

9. Other e-commerce news of interest

Meta is testing two new retail media tools including "product set optimization" and "product insights" that let brands finally measure whether their ads on Facebook and Instagram are actually driving product sales, according to Adweek sources. The first tool lets retail media networks build product catalogs around individual SKUs so Meta's algorithm can optimize ads for specific products rather than just the retailer, solving a longstanding limitation that made it difficult for a Dick's Sporting Goods, for example, to run an effective Nike-specific campaign. The second tool closes the loop on attribution by tying sales back to a specific brand or product rather than just the retailer, giving product manufacturers proof of performance on their ad spend.

Stripe released a preview of a new feature that enables AI companies to pass through and mark up the cost of LLM token usage to their customers. The tool tracks API prices across models like OpenAI, Google, and Anthropic, records customer token usage, and applies the markup automatically, giving AI startups more granular control over pricing for high-volume users. Alongside the feature release, Stripe also launched its own AI gateway for accessing multiple models, but the new billing feature still works with popular third-party gateways like Vercel and OpenRouter as well.

Amazon is shutting down the Wondery podcast network and the $5.99 monthly Wondery+ subscription service, pushing listeners to subscribe to Audible via a discounted plan. Amazon acquired the Wondery podcast network in 2020, which is home to popular podcasts like "How I Built This with Guy Raz," "New Heights," and "Armchair Expert." The Wondery brand will continue to produce its own podcasts, but no longer on its own dedicated app. The shutdown follows a corporate reorganization last year that moved narrative programming to the Audible brand and eliminated 100 jobs.

Walmart is now permitting sellers to offer free product samples to help boost their reviews via a new option called Recognized Reviewer, which lives inside its Review Accelerator. For products that already have sales, but less than 15 reviews, sellers can incentivize buyers after purchase to increase review rate. For newer SKUs with very few reviews, sellers can provide free samples to trusted Walmart reviewers to leave honest, labeled feedback. In both cases, sellers are responsible for covering the product cost, shipping, and applicable fees, only being charged for reviews that are published. 

Stripe partnered with Affirm and Klarna to integrate their BNPL payment options into its Shared Payment Tokens protocol, a tool introduced in October that allows AI agents to make purchases with a shopper's permission and preferred payment method, without exposing sensitive credentials. The integration enables shoppers to see the total cost upfront and select a repayment plan when an AI assistant is helping them browse and buy. The feature is available now for Stripe's direct merchants, with support for merchants that process payments outside of Stripe coming later this year. Stripe also expanded its Shared Payment Tokens to support Mastercard Agent Pay and Visa Intelligent Commerce.

Depop is increasing its Boosted Listing ad fees from 8% to 12%, effective March 23, and the company is encouraging sellers to take advantage of the lower rates now. The company noted that the increased fee "will only apply to new boosts from that date onwards, so any listings boosted before March 23 will continue to be charged the current 8% fee." Honestly, not a bad strategy to encourage sellers to boost their listings. Sellers are already blaming eBay for the move, even though it hasn't even finalized its acquisition of Depop yet! However eBay is likely not to blame, as Depop had already announced the same fee increase in the UK in November 2025, so it was just a matter of time before it hit the US market.

eBay is offering select sellers zero Final Value Fees on up to 25 items that they list in Baby, Fashion, and Home Decor categories between now and the end of March, in a move that Liz Morton of Value Added Resource sees as a response to Vinted's recent push into the US market, where the European resale platform charges sellers no fees at all. The invite-only promotion mirrors a playbook eBay ran in the UK before eventually going fully fee-free for private sellers, which some analysts also attribute to Vinted's growing competitive pressure in the region. The promotion is a notable reversal from eBay CEO Jamie Iannone's previous stance that the US market is different from the UK and that the company had no plans to introduce free selling in the States.

More than 83% of ChatGPT product carousel results are sourced directly from Google Shopping via shopping query fan-outs, compared to just 11% for Bing, according to a recent study by Peec AI researcher Tom Wells published in Search Engine Land. The results indicate that brands that rank well in Google Shopping have a significant advantage in appearing in ChatGPT product recommendations as well. The results suggest that ChatGPT's carousel effectively operates as a retrieval pipeline pulling products from roughly the top 40 organic Google Shopping and Bing positions. I think everyone kind of knew that already, but it's interesting to see the data.

Google will begin enforcing a $5 per day minimum budget for all Demand Gen campaigns starting April 1, aimed at ensuring campaigns generate enough data for its AI to properly optimize during the initial 7 to 14 day "cold start" learning phase. Google said that in most industries, spending less than that amount per day fails to produce enough clicks or conversions to accurately judge whether a campaign works. Advertisers running low-budget tests across many hyper-segmented campaigns will be most affected by the changes. Existing campaigns under the threshold can keep running until any edit is made, at which point Google will require the budget be raised to save changes.

Meta is updating its ad attribution metrics to more closely align with how other platforms, including Google Analytics, measure performance, including a change to link clicks that will now only count actual clicks through to a website rather than likes, saves, shares, and other engagement actions that have historically inflated the metric. The company is also renaming its "Engaged View" attribution to "Engage-Through Attribution" and shifting non-link click interactions like saves and shares into that category, encouraging advertisers to use this metric to capture the full impact of social interactions. Lastly, Meta is shortening the threshold for what counts as an engaged video view from 10 seconds to 5 seconds, citing data showing that 46% of online purchase conversions from Reels happen within the first 2 seconds of attention on video ads.

Apple is now blocking iOS users in the United States from downloading ByteDance-owned apps like Douyin, Doubao, and Fanqie Novel, even for Chinese nationals living in the US with a valid Chinese App Store account, according to WIRED. A pop-up window now appears telling users the app is unavailable in their region, with the restriction appearing to apply only to ByteDance-owned apps and not those developed by other Chinese companies. The timing of the block aligns with the Protecting Americans from Foreign Adversary Controlled Applications Act, which explicitly bars Apple from distributing or updating any app majority-controlled by ByteDance within US borders, though TikTok, CapCut, and Lemon8 remain available under the January divestiture deal.

In January, I reported that Wix introduced Harmony, a hybrid website builder that combines AI-driven vibe coding with traditional drag-and-drop editing, enabling users to turn natural language prompts into actions, while providing granular, manual control via a traditional visual editor. Well now you can access the Harmony builder directly from ChatGPT via Wix's newly launched app. To begin, users can start a ChatGPT prompt with "@Wix" and the app will automatically surface within the chat to begin the website creation process, which seems wildly unnecessary. Why would anyone want to begin a process on ChatGPT that they'd ultimately have to go to Wix's platform to finish? A modern example of just because you can doesn't mean you should.

Kroger's newly appointed CEO Greg Foran said on Thursday's earnings call that the grocery chain's top priorities will be improving its in-store experience and bringing down prices. Foran, who previously served as the CEO of Walmart US, said, "When you combine competitive prices with strong, fresh, and a well-run store, you drive traffic, you grow baskets, and you gain share -- that's what I want to accelerate at Kroger. I've spent my career in food retail, and running great stores is how you make that happen." He also said that in order for Kroger to grow sales more quickly, the company needs to offer customers a compelling reason to shop "by offering great value" -- which just so happens to be the name of Walmart's largest private label brand. Looks like you can take the executive out of Walmart, but you can't take the Walmart out of the executive!

Bold Commerce launched rePete, an AI reorder agent for Shopify stores that predicts when individual customers are running low on a product and sends a personalized nudge to restock with a single click, rather than locking them into a fixed subscription cycle. The tool learns each customer's buying behavior and purchase patterns to generate dynamic reorder predictions and then nudge the shopper to reorder on the communication channel it predicts is most likely to convert. I actually got a sneak peek of the app and it looks very promising. The launch marks Bold Commerce's first new app release in over nine years. 

X launched a new "Paid Partnership" label that creators can attach to sponsored posts, replacing the platform's previous reliance on #ad hashtags and self-written disclosures. X was the last major platform to not adopt a native paid partnership disclosure tool, with Instagram having added one in 2017 and TikTok in 2022. At the same time, the platform also launched a separate "Made with AI" label, 

In other X news... the company is promoting itself to potential advertisers with a new deck that emphasizes its commitment to brand safety, according to the leaked deck shared with Business Insider. X claims in the deck to have achieved a nearly 100% perfect "brand safe" score using Grok, as measured by IAS and DoubleVerify, and mentions the ways it uses Grok to review posts and users' profiles for brand suitability. The move comes after the platform recently took heat for its AI chatbot sharing deepfake sexualized images of women and children, as X attempts to regain trust with advertisers.

Paramount CEO David Ellison announced that the company is planning to merge Paramount+ and HBO Max into a unified streaming platform following its acquisition. He also reassured investors that HBO's identify and creative vision would remain unchanged, stating, "Our viewpoint is HBO should stay HBO." The new combined platform is projected to have over 200M subscribers, which would position it as the number three streaming service behind Netflix, which boasts 301M subscribers, and Amazon Prime Video, which has over 200M subscribers since it's included with Prime membership. 

Amazon ended its book club program on Sunday to instead "focus on other book discovery features for readers." Book club admins and members are no longer able to access their clubs or club-related content such as book selections and suggestions. The Book Club feature, which Amazon launched in 2022, had allowed members to use a widget to suggest books to fellow members and to endorse suggestions made by other members. Amazon is instead pushing users to its Goodreads website to engage with other readers.

TikTok is recruiting US sellers for a new cross-border endeavor called "TikTok Shop US-MX Program" that lets them sell to Mexican customers using their existing US shop credentials, ship directly from US warehouses, and skip the local legal entity and logistics infrastructure that international expansion has historically required. The company is recruiting a select group of sellers for a beta launch running for 9 days later this month. Since launching in the country a year ago, TikTok Shop Mexico has sold over $497M in products, with 128% sales growth between September 2025 and February 2026. 

Amazon, Temu, and Shein are reporting significant delivery delays to the Middle East following military strikes on Iran, with the platforms updating their expected delivery windows to as high as 45 days. Freight forwarders have warned e-commerce companies that shipping costs and delivery times could double if disruptions persist in the region. And persist they do! Amazon confirmed that drone strikes hit two data centers in the United Arab Emirates and a third facility in Bahrain, causing structural damage and disrupted power delivery as emergency crews deployed fire suppression systems. The company also closed its fulfillment centers in Abu Dhabi and suspended deliveries across the region. Nvidia closed its Dubai office and transitioned employees to remote work, while WeRide suspended its robotaxi fleet in the city.

In lawsuits this week...

• Kroger is being hit with two class action lawsuits alleging that the grocer misclassified its e-commerce manager position as exempt from overtime pay in violation of the Fair Labor Standards Act and local wage and hour laws in Colorado and Washington. The lawsuits effectively claim that the role of "e-commerce manager" was just a bullshit name given to product fulfillment roles, titled as such to avoid paying overtime, despite the expectation to work more than 40 hours per week.
• ZhaoCheng Tan and Garrett Reid, investors in Alphabet and Meta, are suing the Trump administration for failing to enforce the law that required TikTok to either separate from its Chinese parent company or face a ban in the US. The lawsuit is asking the court to declare that the administration's multiple extensions to forestall the shutdown of TikTok last year were unlawful, as was the deal for new investors to take over TikTok's US operations, as part of its claims that the "illegal" extensions caused a "direct and very real financial harm" to investors of companies that compete with TikTok.
• OpenAI is being sued by Nippon Life Insurance Co. of America for practicing law without a license. The complaint claims that ChatGPT pushed a woman seeking disability benefits to breach a settlement agreement and file dozens of motions that "serve no legitimate legal or procedural purpose." OpenAI's usage policies state that people cannot use ChatGPT for legal or medical advice unless a licensed professional is involved, but who the fuck read their terms of service? OpenAI could be found liable for not making that disclosure in their AI generated answers.
• Meta is being sued for allegedly, but definitely, collecting sensitive content from users with it smart glasses, after nudity and sexual images were viewed by its employees. More on this later.

In corporate shakeups this week...

• Revolut appointed former Visa executive Cetin Duransoy as its new CEO for the US and simultaneously applied for a US bank charter. If its applications are approved, the company plans to invest $500M into the US over the next five years, aiming to build a presence in the country that helps it reach its goal of 100M customers globally.
• Alibaba's Qwen AI division head, Lin Junyang, announced his resignation, becoming the third senior Qwen executive to depart this year. The news was followed by the announced departure of Yu Bowen, who headed post-training for Qwen.
• A senior member of OpenAI's robotics team, Caitlin Kalinowski, resigned from the company, citing concerns over OpenAI's recent partnership with the U.S. Department of Defense. She wrote, "I resigned from OpenAI. I care deeply about the Robotics team and the work we built together. This wasn't an easy call."
• TikTok's global head of business and commercial partnerships, Sofia Hernandez, is leaving the company after six years to take a "deliberate exhale," according to her LinkedIn post. She wrote, "Choosing to rest is not stepping out of the game. It takes clarity and confidence to step back long enough to recharge your body, reset your thinking, and expand your vision."
• Beehiiv hired Darren Chait as its first chief marketing officer to oversee positioning, demand generation, and marketing operations as the company expands beyond its origins as a newsletter publishing tool. Chait formerly served as VP of growth at Calendly, and before that, he co-founded Hugo, a meeting-notes platform.
• Meta hired the engineers behind the vibe-coding app, Gizmo, which lets people use AI to create and share interactive content like mini-apps or games. The team includes Josh Siegel, Daniel Amitay, Brandon Francis, Rudd Rawcett, and several other ex-Snapchat engineers.

In layoffs this week...

• Oracle is planning to cut thousands of jobs and freeze hiring to manage a cash crunch caused by its massive AI data center expansion. The company disclosed a $1.6B restructuring plan in September and expects its free cash flow to turn negative as it builds infrastructure to compete with Amazon and Microsoft.
• Amazon laid off at least 100 employees in its robotics division responsible for designing warehouse automation systems. The cuts follow the company's recent decision to halt the development of Blue Jay, a multi-arm robotic system designed for smaller spaces.
• Amazon also fired a warehouse employee who needed surgery to repair two work-related hernias for "non-attendance" while he recuperated at home from the operation. Lashone Brown had been granted official medical leave, but was automatically terminated by Amazon's attendance system five days into his approved two-week recovery period in October. Amazon acknowledged the error, but did not correct it, and now Brown has to sue for damages.
• Flipkart laid off around 500 employees, roughly 4% of its workforce, following its annual performance review process, which typically results in the company letting go around 1-2% of its employees. The additional layoffs might have to do with the fact that the company is preparing for an IPO later this year.
• Capital One is letting go of around 1,200 employees at its Chicago offices, bringing its total expected layoffs to almost 1,800 between October 2025 and October 2026. The layoffs, which mostly impact Discover employees, follow Capital One's $35.3B acquisition of the credit card company last year.

OpenAI began developing an internal code repository alternative to GitHub after recent service outages to the Microsoft owned platform disrupted its software engineers, according to The Information sources. Staffers discussed the possibility of selling access to the platform to external customers in conjunction with existing Codex coding agents, though they said the platform likely won't be ready for months if it is to launch. The unreleased project is another example of how OpenAI could directly compete with Microsoft, despite it being one of their biggest and earliest investors and partners.

Kraken became the first crypto firm to gain direct access to the Federal Reserve core payments system, Fedwire, via its banking arm, Kraken Financial, allowing the platform to move client funds and process payments without relying on traditional banks. The approval, which followed more than five years of regulatory engagement, allows Kraken to settle US dollar transactions on the same rails used by traditional banks, enabling faster and more efficient fiat movement for institutional clients while reducing dependency on correspondent banks. The access is limited in scope, with Kraken not earning interest on reserves or having access to the Fed's emergency lending facilities.

Amazon, Claude, and TikTok experienced significant outages last week. Amazon went down for about 5 hours on Thursday, which the company says was a result of code deployment issues. The issue not only impacted Amazon's website and mobile app, but also its pick-up lockers, which customers weren't able to remotely open. TikTok experienced an outage in the US that caused content posting lags for creators, caused by an undisclosed issue at an Oracle data center, marking the second major platform failure tied to Oracle infrastructure since the January sale. Lastly, Anthropic experienced a widespread service disruption affecting Claude.ai and Claude Code, likely driven by an influx of new users after the company shot to the top of the App Store charts following a public dispute with the Trump administration.

Amazon launched its Amazon Now service in Sao Paulo, Brazil on Tuesday, pledging to delivery groceries and essentials in 15 minutes, with plans to expand to seven other cities this month. The service is free for Prime members and will carry no service fee for an undetermined period, with Amazon partnering with delivery app Rappi to fulfill orders. The move helps position Amazon against MercadoLibre and Shopee in the country.

Amazon India is expanding its zero referral fee program to cover 125M products under Rs 1,000 ($12 USD), matching similar commission waivers by Flipkart as the two companies aim to better compete with zero-commission platforms like Meesho. In addition to cutting fees, Amazon is also adjusting its logistics costs by reducing Easy Ship fees by over 20% for items priced below Rs 300 ($3.60 USD). The Easy Ship service allows merchants to hold inventory at their own facilities while Amazon manages pickup and delivery. Amazon really wants to win the Indian market!

🏆 This week's most ridiculous story… An investigation by a Swedish newspaper revealed that Meta is sending videos of people having sex, using the bathroom, undressing, and viewing sensitive financial information to contractors in Kenya, who are viewing the videos as part of their work to train Meta's AI. Contractors told the newspaper that they spent time watching people "going to the toilet, or getting undressed," often not knowing that they were even recording or being recorded. Good lord, can this company get any worse? Meta defends that it automatically blurs users' faces on collected smart glasses footage, but didn't mention whether it has a policy on blurring vaginas.

10. Seed rounds, IPOs, & acquisitions

Opensend, a customer identification and data enrichment platform, acquired Fueled.io, a platform that helps e-commerce merchants collect and organize first-party customer data, for an undisclosed amount. The combined company will help merchants better understand who is engaging with their brand and activate that data across paid marketing, lifecycle messaging, on-site experiences, and measurement, bridging the gap between anonymous site visitors and known customers. Fueled founder Sean Larkin will join Opensend as Chief Product Officer, and Fueled will operate under the Opensend brand going forward.

The Trade Desk CEO, Jeff Green, purchased $150M worth of company stock last week at prices ranging from $23 to $25 a share, according to a Form 4 filing with the SEC. Green said in a blog post that he was "putting my money where my mouth is" and that he has "strong convictions about where value in digital marketing is shifting and why." He went on to outline ten reasons for his optimism, including TTD's decade-long AI infrastructure, an expanding total addressable market that he believes will soon include chatbot and sponsored shopping inventory, a new agentic AI platform called OpenTTD, and what he described as a coming revolution in advertising measurement driven by retail data.

Quince, an online retailer focused on factory-direct luxury essentials, is in talks to raise new funding at a valuation exceeding $10B, more than double the $4.5B valuation it achieved during a $200M funding round last summer. The company recently hit a $2B annualized revenue run rate and continues to attract venture capital despite remaining unprofitable and adjusting to the recent elimination of the de minimis tax loophole. Quince has expanded since it launched eight years ago to sell a wider variety of "affordable luxury" items including furniture, lab-grown diamond jewelry, and even caviar. 

Avalara, a tax-compliance software platform that automates sales tax calculation, filing, and reporting, acquired Versori, an AI-powered integration platform that automates the building and maintenance of connectors between enterprise systems, for an undisclosed amount. The deal helps Avalara connect ERP, e-commerce, and financial systems to deliver automated tax compliance in real time worldwide. Versori's co-founders and employees will join Avalara, and the company will continue to operate under the name "Versori, by Avalara."

Frasers Group, a UK retail conglomerate that owns a portfolio of sports, luxury, and lifestyle brands, acquired a 5.77% stake in Puma, the struggling German sportswear brand, largely through derivatives and put options worth approximately €190M, becoming its second largest shareholder. The investment comes as Puma navigates one of the worst periods in its recent history, having posted a €640M net loss in 2025 and suspended its dividend. Earlier this year, I reported that Anta Sports, China's largest sportswear brand, agreed to acquire a 29% stake in Puma for €1.5B, becoming its biggest shareholder.

Silverflow, a Dutch payment processing platform, raised $40M in a Series B round led by Picus Capital, bringing its total amount raised to over $76M.  The company connects acquiring banks, payment companies, and commerce platforms directly to card networks like Visa, Mastercard, and American Express via a single cloud-native API, positioning itself as a modern alternative to legacy processing infrastructure used by institutions like Deutsche Bank, Bolt, and Payabl. It plans to use the funds to grow its workforce, expand to North America and Southeast Asia, and add support for China UnionPay and JCB card networks.

Decagon, an AI-powered customer support platform that automates customer service interactions, completed its first tender offer allowing more than 300 employees to sell vested shares at a $4.5B valuation, marking a threefold increase from the $1.5B valuation it announced last June. The transactions was led by the same investors that backed its $250M Series D less than two months ago including Coatue, Index, a16z, Definition, Forerunner, and Ribbit.

Amazon acquired the Virginia Science and Technology campus from George Washington University for $427M. The company secured the site to construct a new data center as it expands its AI infrastructure across the state. The deal allows the university the option to keep programs at the site for up to five years. University officials stated that the transaction provided necessary capital, but they are still planning further cost reductions to resolve an underlying structural deficit.

Arda, an AI-powered manufacturing automation platform co-founded by former OpenAI research chief Bob McGrew that uses video models to analyze factory floor footage and train robots to run production processes autonomously, is raising $70M in a round led by Founders Fund and Accel at a $700M valuation. The platform is designed to coordinate both machines and human workers across the entire production cycle, from product design to finished goods, with an explicit goal of making Western manufacturing cost-competitive enough to reduce reliance on China. McGrew, who spent eight years at OpenAI focused on training robots for physical tasks before departing in 2024, is co-founding Arda with Augustus Odena, a former co-founder of Adept AI, and Palantir veterans Jakob Frick and Alex Mark.

OpenAI selected law firms Cooley and Wachtell Lipton Rosen & Katz to begin preparing for a public offering that executives have privately said could come as soon as the fourth quarter of this year. The selection marks one of the first concrete steps toward a listing that would rank among the biggest IPOs of all time given the company's current $730B valuation. Wachtell has already worked on multiple acquisitions for OpenAI, including its purchase of Jony Ive's io products for $6.5B and Statsig for $1.1B last year. Cooley is well known for helping tech companies including Nvidia and Snowflake prepare for IPOs. 

Community Capital, a creator-focused investment firm, acquired Creator's Corner, a TikTok Shop affiliate community and agency that connects creators with brand partnerships, for an undisclosed amount known to be in the multi-millions. The deal gives Community Capital a foothold in the TikTok Shop ecosystem, where Creator's Corner has built a reputation as a top-five agency. The firm plans to reinvest over $1M into the community over the next 12 months to fund live events, expanded educational programming, and tools to help affiliates scale.

Dotdigital, a UK marketing automation platform that helps businesses manage and personalize email, SMS, and cross-channel campaigns, acquired Alia Software, a Shopify app that helps e-commerce stores convert anonymous website visitors into subscribers, in a deal valued at $30M with the potential to reach $60M based on future performance. The acquisition expands Dotdigital's capabilities in onsite engagement and customer data capture and strengthens its position in the Shopify ecosystem. The deal follows Dotdigital's earlier acquisitions of personalization platform Fresh Relevance in 2023 and affiliate platform Social Snowball in 2025.

ZyG Edge, an Israeli AI startup that helps independent inventors compete with global brands by handling their full DTC customer lifecycle, raised $58M in a seed round led by Lightspeed Venture Partners. The company runs each product through an “Agentic Marketability Test” that assigns a ZyG Score, and those that qualify are offered a partnership where ZyG's AI agents handle the entire customer lifecycle, from marketing and SEO to logistics and customer support, on a pay-as-you-grow revenue share model. Top-performing products also gain access to funding from ZyG's investor network, allowing creators to scale without risking their own capital or giving up equity in their brand.

PhonePe, the Walmart-backed Indian payments startup that spun off from Flipkart, targeted a valuation between $9B and $10.5B for its upcoming IPO, expecting to raise up to $1.05B through the offering. The targeted valuation marks a decrease from the $12B private valuation the firm secured in 2023 due to ongoing monetization concerns. Walmart is planning to trim its stake in the company by 12% during the IPO, while Tiger Global and Microsoft plan to exit their positions. 

Nvidia made a $2B investment in both Lumentum, a photonic product maker, and Coherent, an optical components manufacturer, as part of separate multiyear agreements aimed at advancing its data center processors. The funding will support both companies' efforts to expand their US manufacturing capacities and accelerate R&D in optical technologies critical to next-generation AI infrastructure. Both deals are nonexclusive and include multibillion-dollar purchase commitments as well as future access rights to advanced laser components and optical networking products, giving Nvidia a more secure supply chain as it races to scale gigawatt-level AI factories.

Voomi Supply, a B2B e-commerce marketplace serving HVAC and industrial trades, raised $10M in a Series A round led by Asymmetric Capital Partners. The platform simplifies procurement across a highly fragmented supplier landscape, giving professional buyers access to over one million HVAC and industrial parts and equipment SKUs in one place. The funds will be used to accelerate development of its AI capabilities, grow its supplier network, and expand into new product categories.

UniUni, a Canadian last-mile delivery company specializing in e-commerce parcel delivery, raised $85M in equity and debt from Rockets Capital, Royal Bank of Canada, and four unidentified backers from Quebec and Ontario. The funding, which comes less than nine months after the company raised $70M, will be used to support the its deployment of advanced sorting machines across its North American warehouses. UniUni started as a meal-delivery service seven years ago before shifting into e-commerce fulfillment during the height of the COVID pandemic and now generates over $500M in annual revenue, making it one of Canada's largest privately held tech companies. 

Blue Butterfly, a retail consulting firm specializing in operations, profitability strategy, and retail real estate for independent retailers, acquired IndERA, a digital marketing, education, and events-platform, for an undisclosed amount. The deal brings together IndERA's marketing and education platform with Blue Butterfly's expertise in retail operations, helping the company gain strategic and operational support to improve store performance and plan long-term growth. IndERA founder Crystal Vilkaitis will remain active in the business following the acquisition, while the agency's core offering will remain in place.

Austrian Post, the nation's postal service provider, acquired a 70% stake in euShipments.com, a logistics partner for online merchants in Central and Eastern Europe, for an undisclosed amount. euShipments.com serves more than 1,300 online retailers across all 27 EU member states through 15 fulfillment centers and 60+ courier partnerships, offering warehousing, delivery, payment processing, and returns management through a single integration. The deal gives Austrian Post a stronger presence in Southeast and Eastern Europe's e-commerce logistics market.

Elon Musk's xAI and X Corp. plan to repay approximately $17.5B in combined debt in full, with some bonds being redeemed early at a premium including $3B in high-yield bonds priced around $1.17 on the dollar. The move follows a series of restructuring steps including xAI's acquisition of X in 2025 and SpaceX's recent acquisition of xAI at a $250B valuation, though the companies have not disclosed the source of the repayment capital. The debt payoff would mark a significant financial milestone for Musk's businesses, cleaning up the heavily leveraged balance sheet that has hung over X since Musk's $44B takeover of the platform in 2022.

Rozana, an Indian rural omnichannel commerce platform that connects fast-moving consumer goods brands with underserved markets, raised $31.6M in a Series B round led by Bertelsmann India Investments. The company will use the funds to strengthen its technology infrastructure, expand into new product categories, and develop private label offerings. Rozana has recently expanded its hybrid commerce infrastructure to 21,000 villages and serves more than 1M households across the country.

Soles4Souls, a nonprofit organization that collects and distributes shoes and clothing to people in need around the world, acquired Erren Recondition, a European footwear and apparel reconditioning company, for an undisclosed amount. The deal strengthens Solutions4Good, the organization's circular solutions platform, which provides brands with responsible pathways for sorting, reconditioning, recommerce, repurposing, and reuse, by adding Erren's decades of technical reconditioning expertise across shoes, clothing, and accessories. Erren will continue operating in Europe under the name "Erren Recondition, a Soles4Souls Company," while its methods are integrated into Soles4Souls' US and UK operations as part of a unified global circular platform.