Hi Shopifreaks
🎉 Before we begin, I'm excited to present a new pitch from my video series 90 Second Pitches — a channel that helps you discover innovative e-commerce technology from the most promising startups. You can subscribe to the channel on YouTube & LinkedIn.
Today's 90 Second Pitch comes from Jack Wilson at Section Store, a marketplace for pre-built Shopify sections and product blocks that lets merchants quickly add new features and layouts to their storefront without custom development.
Section Store offers a library of 700+ sections and product blocks that install directly into your Shopify theme, making it easy to upgrade your store design, add functionality, and test new layouts without hiring a developer. I actually use it on several stores I manage and was thrilled when they asked to pitch on the channel because I'd love for more merchants to learn about what they have to offer, as it's become such a crucial part of my store development process.
Watch Jack's 90 Second Pitch below and then let him know in the comments if you're going to add Section Store to your tech stack.
90 Second Pitch:
▶️ Watch On LinkedIn | ▶️ Watch On YouTube
The Full Interview:
▶️ Watch on YouTube
Visit Section Store on the Shopify App Store to install the app for free and browse their selection of sections and product blocks. It works with every theme.
Want to pitch your startup? Hit reply and show me what you're working on. I've got more great pitches coming your way soon, and I'd love to feature your e-commerce app or SaaS solution too. Hope you enjoy the new series!
And now onto your regularly scheduled programming…
In this week's edition I cover:
- Amazon lands first blow against Perplexity
- The Trump Administration's $10B brokerage fee
- Amazon's Shop Direct goes third-party
- OpenAI tests an Ads Manager
- Amazon denies AI-code issues
- Facebook Marketplaces gets an upgrade
- Amazon sales events are coming early this year
- Anthropic versus The White House
- Google's new “Sponsored Shops” blocks
- UPS & FedEx raise fuel surcharges
- Amazon jacks the price of Prime Video
- Alexa is getting sassy
All this and more in this week's 269th Edition of Shopifreaks. Thanks for subscribing and sharing!
Stat of the Week
Anthropic's $200/month Claude Code subscription could consume up to $5,000 in annual compute, up from $2,000 last year, according to an internal analysis by Cursor. The numbers suggest that Anthropic, like its competitors, is willing to heavily subsidize its customers' usage in order to gain market share. Cursor also subsidizes some users, but not as heavily as Anthropic, and claims to operate on positive margins.
1. Amazon wins court order to block Perplexity from scraping its site
In November, I reported that Amazon filed a lawsuit against Perplexity to stop the company's AI browser, Comet, from shopping on its website. Amazon had previously sent cease and desist notices to Perplexity, which it ignored, and tried to block Perplexity's AI agents with technology, which it bypassed.
Perplexity called the lawsuit Amazon's “first legal salvo against an AI company” and a “threat to all Internet users.” They went on to claim that Amazon's sole motivation was to keep consumers shopping directly on their website so that they can continue to serve them ads. Then they went on a rant about “AI rights” and how corporations shouldn't “discriminate against users based on which AI they've chosen to represent them.”
Amazon said it “shares the industry's excitement about AI innovations,” but “transparency is critical” and that “Perplexity has refused to operate transparently” despite multiple requests by Amazon to stop its undisclosed agentic activities. Amazon went on to reference the risks that third-party AI agents bring to the customer experience and security of their shoppers, as well as multiple laws that Perplexity is breaking by not abiding by Amazon's request and attempting to circumvent its firewalls.
Watch my video on LinkedIn or read the full post to learn more about the merits of each side's argument.
Flash forward four months…
Amazon won a temporary federal injunction against Perplexity to block Comet browser from scraping its e-commerce website after Judge Chesney ruled that the retailer provided strong evidence of unauthorized access.
Chesney said Amazon submitted “essentially undisputed evidence” that it spent more than $5,000 to respond to the issue, including “numerous hours” where its employees worked to develop tools to block Comet from unauthorized access. (Wow, a whole $5,000?)
Perplexity had seven days to appeal the decision, which ends today.
This is a case that I am following with great interest, as the outcome will set a precedent for how courts treat AI agents in the future in regards to whether or not they can access websites without permission — or as Perplexity says, their “rights.”
I've previously argued that websites can already choose whether or not to function on certain browsers, regions, or devices, so they should also be able to choose which AI can interact with their systems. I anticipate finding out whether the courts agree with me.
2. The Trump Administration is set to take a $10B fee for the TikTok deal
The Trump Administration is set to receive a $10B fee from investors for brokering the TikTok deal, according to The Wall Street Journal and The New York Times. As a reminder, investors were able to steal scoop up TikTok's U.S. operations at a remarkable $14B valuation, which means the “broker fee” represents a more than 70% commission on top of the total deal value.
Oracle, Silver Lake, and MGX have already paid the Treasury Department roughly $2.5B when the deal closed in January and will make the remaining payments in installments, according to people familiar with the matter.
President Trump alluded to the commission when announcing the framework for the deal last year:
“The United States is getting a tremendous fee-plus—I call it a fee-plus—just for making the deal and I don’t want to throw that out the window.”
So while the fee itself comes as no surprise, the size of it certainly does. The $10B payment is unprecedented for a government's role in arranging a transaction, or for a private transaction for that matter. For comparison, The Wall Street Journal reports that Bank of America is in line to make around $130M for advising railroad operator Norfolk Southern on its $71.5B sale to Union Pacific, which is one of the largest fees on record for a single bank on a deal, yet still represents less than a single percentage point fee, which is typical for private deals.
70% feels more like a shakedown than a commission. Frankly, the whole deal stinks.
For one thing, TikTok U.S. isn't worth $14B. It's worth a heck of a lot more. The deal valued TikTok's U.S. operations at roughly 1.3x its annual revenue. In comparison, Meta is valued at 11.4x its annual turnover. If TikTok had been awarded the same valuation-to-revenue multiple, which it should have been, given that it's the most influential social network in the world right now, then the U.S. entity would have been valued at roughly $125B.
Secondly, why were the other bids rejected? Frank McCourt's Project Liberty consortium submitted a $20B bid as far back as January 2025, MrBeast's group said it had secured more than $30B, and Reid Rasner offered close to $50B. Yet somehow, in a free market, a $14B bid won the deal? Is it safe to assume the $10B commission influenced that decision?
Am I the only one who thinks there's something off about this whole TikTok deal and the accompanying $10B fee? Hit reply and let me know.
3. Amazon enables third-party product feeds in Shop Direct
Amazon is making it easier for merchants to participate in Shop Direct, its AI discovery experience that surfaces products from outside its own marketplace, by integrating with third-party feed syndicators including Feedonomics, Salsify, and CEDCommerce. The new integrations allow brands to automatically sync their catalog, pricing, and inventory in real time so that their products can appear in Amazon search results and Rufus answers.
Quick Backstory: Shop Direct launched as a beta in February 2025, when Amazon began testing a feature that linked customers to a retailer's website when its own search results didn't include the product they were looking for. Customers would see product information on Amazon and could click through to the retailer's site to check pricing and delivery options. The program has since expanded and is now live for all U.S. customers on Amazon's website, mobile app, and AI shopping assistant.
A year later, Shop Direct now indexes over 100M products from more than 400k merchants, with tens of millions available through the “Buy for Me” agentic feature that lets Amazon complete the purchase on a customer's behalf.
The new integrations with third-party product feeds give merchants a faster way to submit their products into Amazon's index, while also allowing them to use their existing product feeds, as opposed to making a new one specifically for Amazon.
Amazon says it plans to add support for more feed providers and is also developing a merchant portal that will allow merchants to submit their product feeds directly.
As for Amazon's benefit, TechCrunch's Sarah Perez wrote:
“While the move to be included on Amazon could certainly boost a brand’s exposure and potential sales, it could also give Amazon insights into which brands, products and price points are most appealing to customers. The company could use this information to improve its own business by providing data on competing products, tracking trends, identifying potential Buy with Prime partners, and more.”
MajeseticIQ founder Joe Nilsen says the playbook is familiar:
“This is not a traffic referral program. This is one of the most efficient competitive intelligence plays in retail history. And merchants are plugging in the cables themselves… Free access builds dependency. Dependency enables monetization. Monetization funds the next moat.”
Last year, when Amazon started growing its Autos division, I asked:
“Why in the world would Hyundai, Ford, and soon to be other auto manufacturers give away control of their inventory and sales process to the most unscrupulous and ruthless of partners? Has the automobile industry learned nothing from what happened to retailers in the books and toys industries after partnering with Amazon? Why would automakers do this? So they can later pay Amazon advertising fees after they've helped build its market share?”
I could ask similar questions about merchants that participate in Shop Direct.
4. OpenAI is building its own ad tech stack faster than anticipated
Last week I reported that OpenAI partnered with Criteo to sell its chatbot ads and was in talks with The Trade Desk and other media agencies and ad techs to do the same. I wrote:
“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.”
Well, “eventually building its ad tech in-house” may actually come sooner rather than later. Digiday previously reported that OpenAI is hiring a:
- Monetization Infrastructure Engineer – to build its ads systems
- Engineering Manager – to lead the team
- Product Designer – to define what its ad tools will look like inside ChatGPT
- Senior Manager – to own ad revenue accounting
- Trust and Safety Expert – dedicated specifically to the ads product
- Plus a few other roles dedicated to building its ad tech stack.
Now Adweek reports that OpenAI has begun testing an Ads Manager with a small group of partners that lets marketers run, monitor, and optimize campaigns in real time and is gathering feedback. A company spokesperson confirmed that dashboard and added that testers are also currently receiving CSV reports with performance data that includes clicks and impressions.
In hindsight, I'm not sure why I doubted how quickly OpenAI would rush something to market. Shipping unfinished, untested, and poorly designed products seems to be their thing.
5. Amazon says AI-written code wasn't responsible for its outages
Amazon summoned a large group of engineers to a meeting last week for a “deep dive” into recent outages, according to the Financial Times. In recent weeks, Amazon's website, mobile app, and pick-up lockers went down for almost 6 hours, and in a separate incident, the company lost nearly 120k orders and experienced roughly 1.6M website errors.
Amazon Senior VP Dave Treadwell acknowledged that the site's availability “has not been good recently” and that “novel GenAI usage for which best practices and safeguards are not yet fully established” was a contributing factor to the outages.
In response, the company plans to introduce tighter controls that will require engineers to document their code changes more thoroughly and secure additional approvals before deploying them. Amazon is also developing other safeguards designed to introduce “controlled friction” into the code-change review process.
Amazon confirmed that the meeting happened, but denied that AI-written code caused the outages:
“In fact, only one of the recent incidents involved AI tools in any way, and in that case the cause was unrelated to AI and instead our systems allowed an engineering team user error to have broader impact than it should have. Much of the coverage of the service incidents has focused on a weekly Amazon Stores operations meeting and a planned discussion of recent outages. Reviewing operational incidents is a routine part of these meetings, during which teams discuss root causes with the goal of continuing to improve reliability for customers.”
This is the second time in a month that Amazon has publicly disputed Financial Times reports that suggested AI-written code caused outages. They really want you to know that their AI doesn't suck!
6. Meta introduces new AI selling tools for Facebook Marketplace
Meta introduced new AI tools for Facebook Marketplace to help make selling items easier and build trust and transparency in the platform. Here's a recap of what's new:
Faster Listings – Users can now upload item images and let Meta AI do the rest, including creating a draft listing, filling in item details, and even suggesting a price based on similar items listed in the area. I recently invested in a startup called Firesale that offers a similar value proposition — only it hasn't launched yet and now Facebook does it. Oops!
Simplified Shipping – Sellers can now generate prepaid shipping labels in just a few clicks from within the platform and keep track of every shipped order in one place via a unified dashboard.
Automated Replies – A new AI tool can automatically respond to certain buyer questions by pulling information straight from the listing, including the price, description, and pickup location. Sellers can enable the feature during the listing creation, preview exactly what the system will say to questions, and even edit the replies. The tool aims to reduce the repetitive back-and-forth that burdens sellers with simple questions like “Is this still available?” So now, instead of sellers having to respond “yes” a million times to that question, buyers will be automatically told “yes” long after the item has sold!
Profile Summaries – Facebook is using AI to generate profile summaries so that buyers can see an overview of a seller's profile including how long they've been on Facebook, number of friends, and a summary of Marketplace activity like their listing history, types of items they sell, and seller ratings.
Great improvements, but I'm sure Facebook Marketplace buyers will find new and innovative ways to be awful.
7. Big Spring Sale starts next week, and Prime Day will happen in June
Amazon announced that its Big Spring Sale will return this year and run from March 25th to the 31st, featuring savings across 35 categories including spring fashion staples, beauty products, and home & garden. Customers can also expect deals on groceries and household items for spring, such as Easter dinner bundles and pantry restock items.
Amazon launched its Big Spring Sale event in the UK in 2023 as a three-day event, and then expanded it to the US in 2024 as a five-day event. In 2025 it was extended even longer to seven days. This year marks the third year of the sale in the U.S. and fourth year overall.
Walmart, Target, and several other major retailers started running overlapping Spring sales events a couple years ago to compete with Amazon's Big Spring Sale. Those events will likely begin next week as well, though they haven't been officially announced yet. My guess is they will be later today.
Three months later, here comes Prime Day!
Amazon is moving its Prime Day sale event up to late June this year, according to Bloomberg sources, though Amazon hasn't yet announced the change publicly. The retailer has historically held the event in early July, with the exception of two years during the pandemic, and last year the event was extended to four days from the usual two and drove $24.1B in online spending across the U.S., up 30% from a year ago.
I'm curious if the potential last-minute change is designed to beat Walmart, Target, and other competitors to market, which started holding their own sales events in early July several years ago, and whether those companies will move their events up too? Place your bets on my LinkedIn Poll.
It's also worthy of mention that shifting the dates of the event to June pushes Prime Day into Amazon's second quarter, which makes me wonder if Amazon projects slow sales in Q2 and needs the boost. Of course, it might just want a very good Q2 to divert investor attention away from its unprecedented capex spending so far in 2026.
Either way, mark your calendars: Prime Day is end of June this year. Better tell your suppliers to bump your June order up while you still can.
8. What to know about Anthropic's battle with the White House
I've been debating how deep to go on the Anthropic vs. White House story given that it's not directly e-commerce related, but it's the biggest story in tech right now and the outcome will inevitably ripple across the industry — including to e-commerce firms that rely on AI infrastructure. So with that said, I want to recap what's been happening and why it matters.
How it started…
Anthropic had been working with the Department of Defense under a contract that included guardrails preventing its AI from being used for mass surveillance of Americans or fully autonomous weapons systems. The DOD pushed back, arguing it should be able to use AI for any “lawful” purpose without restrictions imposed by a private contractor, and when Anthropic refused to remove those limits, the Pentagon labeled the company a “supply-chain risk,” which is a designation typically reserved for foreign adversaries like China. Bitter much?
The Trump administration then ordered all federal agencies to cease using Claude and begin a six-month phaseout, after which OpenAI immediately stepped in to sign a deal with the DOD to fill the gap faster than your ex-wife's “best guy friend” after the divorce.
The Wall Street Journal reported that Anthropic's Claude had been used in active military operations, including the raid that led to the arrest of Venezuelan leader Nicolás Maduro and for intelligence assessments and targeting in the U.S.'s ongoing conflict with Iran.
Now you're caught up to the beginning of last week when all this happened…
- Anthropic filed two federal lawsuits challenging the designation and contract cancellations, arguing the Pentagon exceeded its authority and was retaliating against the company, which it definitely was.
- Anthropic warned that the moves could cost it billions of dollars in 2026 revenue, citing specific contracts already being paused or reduced by private sector clients spooked by the designation.
- 37 researchers from OpenAI and Google, including Google DeepMind chief scientist Jeff Dean, filed an amicus brief supporting Anthropic.
- Microsoft filed its own amicus brief warning that the designation would disrupt government contractors that had integrated Anthropic products and may leave some with no alternatives.
- The State Department shifted its internal StateChat tool from Claude to GPT-4.1 following the presidential directive.
- Google announced it would provide its Gemini Agent Designer to the Pentagon for unclassified work, and is negotiating to place it on classified systems, despite Google employees simultaneously signing the amicus brief supporting Anthropic.
- Pentagon CTO Emil Michael publicly ruled out any renewed negotiations and accused Claude of “polluting” the defense supply chain with embedded policy preferences.
- Palantir CEO Alex Karp publicly confirmed that his company is still using Anthropic's Claude to support the war in Iran despite the Pentagon blacklist, though it eventually plans to add other models.
- A judge moved the hearing from April 3 up to March 24 after Anthropic argued urgency, while the Justice Department declined to commit to not taking retaliatory actions, such as issuing an executive order targeting Anthropic, before the hearing date.
Meanwhile, the court of public opinion has already made its ruling. Within days of the Pentagon blacklist, Anthropic surged to the number one spot on the Apple App Store, overtaking ChatGPT for the first time ever, while ChatGPT uninstalls surged 295% and a viral “Cancel ChatGPT” campaign spread across Reddit and X. By March 2nd, Claude had 11.3 million daily active users , up 183% from the start of the year, with its daily US downloads surpassing ChatGPT's for the first time.
9. Other e-commerce news of interest
Squarespace launched Balance, an embedded financial account that allows merchants to access funds within hours, earn cash rewards on balances held, and spend directly from their Squarespace balance with a Visa Card. (Creative name! I bet Shopify wished they thought of it first. Oh wait…) Balance is available to U.S. users at no additional cost and will expand globally in the coming months. The move follows Squarespace's entry into financial products during the last few years including the launch of Squarespace Payments in 2023 and Squarespace Capital in 2025, which either intentionally or coincidentally also follow Shopify's naming convention.
Meta will soon begin requiring advertisers in six European countries to cover the costs of digital services taxes imposed on local sales made by tech firms, via new “location fees” that apply to ads delivered in those countries, even if the advertiser isn't based there. The fees will apply to Austria, France, Italy, Spain, Turkey, and the UK, and range between 2-5% depending on the country. The additional charges, which Meta has absorbed since they first went into effect starting with France in 2019, will be passed on to advertisers beginning July 1st. Alphabet and Amazon currently charge similar fees in response to the regional tax levies.
Google is testing “Sponsored Shops” blocks within Google shopping results, as spotted by PPC Specialist Arpan Banerjee. Instead of only showing individual product listings, Google is highlighting entire stores with multiple products in one block. Banerjee's screenshot showed a search for “backpack” reveal a sponsored three-column grid with two products from various brands appearing in each column alongside the store name and rating, giving each brand more visibility than a single listing. First impression…. I like it! As an advertiser, I'd appreciate that additional real estate, though I'd need more info before I could say if I was willing to pay for it.
UPS and FedEx raised their domestic fuel surcharges in response to the Iran war's impact on fuel prices, with UPS increasing its U.S. ground fuel surcharge by 1% effective March 9 and FedEx close behind. Both carriers adjust rates weekly, which means further increases are likely if fuel prices remain elevated or continue to increase. Both carriers have also introduced temporary international surcharges, with UPS applying a $0.64 per-pound surge fee between the U.S. and 15 Middle Eastern countries, and FedEx applying $0.50 to $0.70 per-pound surcharges across dozens of countries in the Middle East, South Asia, and Africa. FedEx also raised its U.S.-to-Israel surcharge to $1.50 per pound, up from $0.50 previously, with all international fees remaining in effect until further notice.
Amazon launched Health AI on its website and mobile app to give users personalized medical insights and the ability to agentically book appointments, manage prescriptions, and connect with licensed care providers on their behalf. The tool can explain lab results and medical records, manage prescription renewals through Amazon Pharmacy, and connect patients directly to One Medical professionals via message, video, or in-person visits. As an introductory offer, eligible U.S. Prime members receive up to five free direct-message consultations with a One Medical provider for more than 30 common conditions. If Health AI sounds familiar, it's because the tool initially launched earlier this year for One Medical members via the service's dedicated app, and now it's expanding to Amazon's website and app.
Shopify and Klaviyo launched an integration that syncs Shopify Markets data into Klaviyo's CRM to help merchants automate localized content, pricing, and product information across regions. Brands can now dynamically serve product details in local language and currency through a single marketing template that adapts to each customer's location, eliminating the need to manage separate catalogs or build manual workarounds. The feature, called Locale Aware Catalogs, also helps ensure shoppers only see regionally available products and are directed to the correct localized storefront when they click through. I love it! That'll be a big time saver for merchants that sell internationally via Shopify Markets.
Amazon is rebranding its ad-free tier of Prime Video to now be called Prime Video Ultra and jacking up the price from $2.99/month to $4.99/month or $45.99/year. Remember, this is already on top of the $14.99/month or $139/year that you pay for your Prime membership, which used to include an ad-free Prime Video experience at no additional charge, or on top of the $8.99/month standalone ad-support subscription to Prime Video that dozens of people subscribe to. Will there be new video content? Think again. A better app experience? Sorry, also a “no.” So it's just a new dumb name and higher price? Bingo! Amazon may be greedy, but at least it's predictable. We all knew that the initial $2.99/month add-on charge was just a foot in the door price. I get it, Amazon, but for the additional fee, can you at least start putting out seasons of The Boys faster than every two years?
Amazon distributed internal talking points to AWS sales and marketing staff to address delicate topics around its $50B investment in OpenAI, including how to reassure customers that its Anthropic partnership remains strong, how to describe the new Stateful Runtime Environment without implying customers can directly “access” OpenAI models, and how to push back on circular financing concerns. Employees were told the SRE “is powered by” or “integrates with” OpenAI models but are explicitly prohibited from saying it “enables access to” them or functions as a passthrough to GPT, which separates the deal from Microsoft's model-hosting arrangement on Azure. The memo also addresses concerns that the deal could sideline Amazon's own Nova AI models and Quick agentic platform, with pricing, technical limits, and regional availability all listed internally as “stay tuned.”
Disney is starting to roll out Verts, its short-form video feed that features clips from movies and shows on Disney+, to its mobile app users in the U.S. Viewers will be able to access the feed through a new icon in the app's navigation bar, swipe through the feed like TikTok, and add shows to their watchlist or jump directly into the show or movie. Initially the Verts tab will exclusively showcase content from Disney+ programs, but eventually the company wants to feature fan-made videos and “other storytelling formats” — whatever that means. Netflix launched a similar short-form video feed last year.
Etsy is changing how shop review ratings are calculated, now using a seller's entire lifetime review history as opposed to only using reviews from the past year, although newer reviews will carry more weight. Etsy's Seller Handbook says that each review's influence will be reduced by half every year, which means a 5 year old review only carries 3.125% of the weight of a new review. The change will have the biggest impact for small sellers, who may have taken time off from their stores. Whereas after a year those sellers would previously have returned to a zero star seller rating, now they will at least restart with an aggregate weighted rating based on their previous years selling on the platform. I wonder if this is directly related to sellers leaving Etsy in recent years? Is this revised review system designed to help win them back?
Meta expanded its affiliate program to allow creators to add shoppable product links directly to their Reels and earn commissions on sales generated as a result of the click. Creators can browse thousands of products from Amazon and Shopee and choose items that they feel align with their content, effectively turning every Reel into an advertisement. Content featuring affiliate links will be classified as branded content and must carry a paid partnership label, but creators are not required to tag a specific business partner. Brands are given control to untag their products from content they don't feel is a good fit.
Google rolled out its branded queries filter in Search Console to all eligible sites, giving merchants an easy way to segment branded and non-branded search traffic in the Performance report without relying on manual regex filters or keyword lists. The filter categorizes queries into branded (including brand name variations, misspellings, and related products) and non-branded groups, and applies across all search types including Web, Image, Video, and News. Google also added a new Insights report card that breaks down click traffic between branded and non-branded queries to help site owners measure brand recognition over time.
Meta launched new anti-scam tools across its apps including device linking warnings on WhatsApp that indicate when a scammer is trying to trick you into linking your account to their device, Facebook alerts for suspicious friend requests, and advanced scam detection on Messenger for common scams like fake job offers, celebrity impersonation, and deceptive links. Meta also says it's expanding advertiser verification to more of its high-risk categories to increase its total number of verified advertisers from 70% today to 90% by the end of the year. The changes are likely in response to regulatory pressure and public criticism over recent reports indicating that Meta is a breeding ground for fraud and financial scams, and that the company went out of its way to deceive government regulators over just how prevalent the scams were on its platforms.
Google, Microsoft, Palantir, IBM, Nvidia, and Oracle have been named as potential targets by Iran as the war with Israel and the U.S. heats up. Iranian state-linked media published a list of offices and data centers run by U.S. companies with Israeli links whose technology has been used for military applications. Not to appear insensitive, but as they should be, right? Big Tech companies can't have the best of both worlds — collecting military contracts and then expecting to be shielded by their identity as a search engine, cloud provider, or software company when the bill comes due. While I wish the best for all employees, at this point it's a choice to work for Big Tech companies that power the military-industrial complex. Several of the companies listed have begun taking precautions such as asking employees to work remotely or limit travel.
In lawsuits this week…
- Gracenote, a Nielsen-owned entertainment metadata and content identification company that licenses curated descriptions and identifiers for movies, TV, music, and sports, is suing OpenAI for the unauthorized and unpaid use of its metadata and its framework for connecting that information. The suit alleges that OpenAI improperly copied and used its data “to create their own commercially valuable AI products, all without paying a dime,” and that Gracenote's previous attempts to work with OpenAI for a licensing agreement were rebuffed or ignored.
- The mother of a girl who was wounded in a school shooting in Canada last month is also suing OpenAI for not warning police about the shooter when it easily could have. Eight months before the shooting, which killed eight people and injured 25 others, OpenAI employees had been made aware of the shooter's conversations with ChatGPT after they were flagged by an automated review system, but leadership decided not to report the conversation to authorities. The suit accuses OpenAI of rushing ChatGPT to a global market without conducting proper safety studies or implementing strong enough safeguards.
- Indie artists are suing Google over allegedly using their copyrighted music from YouTube to train its AI music generator without permission. The complaint claims the company used its control over the music distribution ecosystem, including YouTube uploads and copyright identification systems, to build a competing product using the artists' own work, calling it “theft at scale,” which pretty much describes the AI industry in a nutshell right now.
In corporate shakeups this week…
- xAI co-founders Zihang Dai and Guodong Zhang departed the company, leaving only two of the original 11 co-founders.
- To help make up for the recent exodus, xAI hired Andrew Milich and Jason Ginsberg, two senior leaders from Cursor, to lead efforts in improving its models' programming capabilities.
- Adobe CEO Shantanu Narayen announced that he is stepping down from his role after 18 years once a successor is appointed, though he will remain as board chair.
- Microsoft Experiences & Devices head Rajesh Jha retired after more than 30 years at the company, where he most recently led the unit that oversees Windows, Microsoft 365, and Surface hardware.
- DoorDash Chief Marketer Kofi Amoo-Gottfried is stepping down in May after seven years in the role to spend more time with his kids before they leave for college, according to his LinkedIn post.
- Simon & Schuster named former Amazon and Airbnb executive Greg Greeley as its new CEO. Greeley succeeds Jonathan Karp, who was named CEO in May 2022 and is stepping down to launch a new Simon & Schuster imprint called Simon Six, publishing a title by Neil deGrasse Tyson to kick off the company.
- Slate Auto appointed former Ford executive Peter Faricy as its new CEO, while current CEO Chris Barman will continue to work at the company as its President of Vehicles.
- MNTN hired former TikTok growth chief Garland Hill as its first-ever chief revenue officer and former NBCUniversal streaming head Peter Blacker as global head of premium content to accelerate its push into the SMB market.
Meta is planning to layoff 20% or more of its workforce as it seeks to offset its costly AI infrastructure bets and prepare for an AI-assisted workforce moving forward, according to three Reuters sources. Top executives at the company recently disclosed the plans to other senior leaders and told them to begin planning how to streamline their divisions. If the rumors prove to be true, the layoffs would mark Meta's biggest to date. Meta spokesperson Andy Stone said, “This is speculative reporting about theoretical approaches,” which doesn't deny the plans.
A Connecticut man pleaded guilty to wire fraud after running a scheme that defrauded Amazon Logistics of over $3.5M by submitting fake invoices for trailer movements that never took place. Believe it or not? Straight to jail! Ameer Nasir set up 23 fraudulent trucking companies, some using stolen DOT numbers from real carriers, and exploited a manual override in Amazon's Relay TMS that allowed him to bypass the platform's geo-fencing and falsely mark trailers as delivered. Nasir successfully pulled off the scam more than 1,000 times between December 2019 and February 2021, and now faces up to 20 years in prison and $3.5M in restitution at his May 29 sentencing. Fool me once, shame on you. Fool me one thousand times, shame on Amazon!
Google introduced a new Game Trials feature that lets users try out premium games without having to make a purchase, aiming to encourage more users to indulge in paid titles. If users try the title and decide to purchase the full game, they can pick up right where they left off in gameplay post-purchase. Game Trials is initially rolling out to paid games on mobile, with plans to come to Google Play Games on PC in the future.
Italian prosecutors are seeking a criminal trial against Amazon's European unit and four of its executives for allegedly enabling $1.4B in VAT evasion by mostly Chinese sellers who sold goods in Italy without disclosing their identities between 2019 and 2021. Amazon already settled the tax dispute itself in December by paying €527M to the country's Revenue Agency — and historically, paying fines had been enough to end related criminal probes. However it seems that Italy wants to create an example out of Amazon. If the allegations hold up in court, the case could open the door to similar charges against Amazon across the EU, where VAT rules are harmonized.
Revolut received full UK banking authorization from the Prudential Regulation Authority, five years after first applying in 2021 and eight months after receiving a restricted license that capped customer deposits at £50,000. The full license allows the fintech to offer retail and business accounts as a fully licensed bank, including lending products previously unavailable to it in the UK. The milestone comes as Revolut simultaneously pursues a US banking license and targets expansion into 30 new markets by 2030.
John Lewis launched on TikTok Shop on March 9th as part of a 90-day Mother's Day pilot, making its curated beauty and gifting items shoppable on the platform for the first time. Ulta Beauty is also joining TikTok Shop this month, debuting on March 17th with a selection from more than 15 brands across makeup, skincare, hair, and fragrance, plus over 25 exclusive bundles, becoming one of the first major multi-brand retailers on the platform in the U.S. Ulta plans to complement the storefront with livestream shopping and creator-driven educational content, while John Lewis's TikTok launch is part of a broader £800M transformation that also includes plans to make its products shoppable through AI platforms like Google Gemini and ChatGPT later this year.
Best Buy is attempting to position itself as the go-to destination for AI-powered consumer hardware, dedicating space in 70 stores to Meta products like AI glasses and VR headsets, while also partnering with OpenAI to display its product catalog in ChatGPT and joining Google's Universal Commerce Protocol for AI-powered search and shopping. CEO Corie Barry says the company has seen strong growth in emerging categories like AI glasses, health rings, and PC gaming handhelds, and that nearly 70% of the company's AI-capable laptop and desktop models are retail-exclusive to Best Buy. The push comes as the company's overall revenue remained flat at $42B for the fiscal year. I think it's a great move for Best Buy, as it's already got the geographic footprint to serve as a retail partner for these AI companies.
The Canadian government approved an agreement to allow TikTok to continue local operations in the country following a national security review. As part of the deal, TikTok agreed to implement new security gateways and privacy technologies to control access to Canadian user data, as well as appoint an independent third-party monitor to audit data access controls and enhance protections for minors. In November 2024, Canada's industry ministry had ordered TikTok's local business unit to be dissolved, citing national security risks, but Canada's federal court overturned that order in January, allowing TikTok to continue operating in the country. Did Justin Trudeau also receive $10B for brokering that deal?
Tencent is building a new AI agent for its WeChat messaging app, hoping to beat rivals like Alibaba and ByteDance in the race to dominate China's domestic AI market, according to The Information sources. The new agent would connect with the millions of mini apps running inside WeChat that offer services like booking taxis and ordering groceries, potentially performing those tasks on behalf of WeChat's 1.4B monthly active users. The company is treating the project, which has been in the works since at least the first half of last year, as a high-priority, top secret initiative — although now you know about it, so it's not such a secret anymore.
Apple is lowering its App Store commission fees in China for in-app purchases and paid applications from 30% to 25%, while in-app purchases for developers belonging to its small business and mini apps partner programs will be cut from 15% to 12%. The move follows pressure from local regulators, with state media estimating that the policy change will save Chinese software creators more than 6 billion yuan ($873M) annually. Experts predict that in future, the Chinese government may request that Apple collect App Store revenues in China instead of overseas, and further tighten regulatory oversight for foreign apps published in the country.
South Korea's antitrust regulator is planning amendments to the country's E-Commerce Act to limit data collection and require local agents for foreign platforms. The proposed changes restrict secondhand trade platforms to verifying only phone numbers and e-mail addresses for personal sellers and mandate that overseas marketplaces appoint a local agent if they exceed specific revenue thresholds. The regulator drafted the new privacy limits following a large-scale data breach at Coupang, which exposed the personal data of 33.7M customers, roughly two-thirds of South Korea's entire population.
🏆 This week's most ridiculous story… Amazon released a “Sassy” personality for Alexa+ that brings “unfiltered personality with razor-sharp wit, playful sarcasm and occasional censored profanity” to the AI assistant. Basically it tries to roast you while interjecting PG-13 swear words like “damn” into the mix. One TikToker posted about how Alexa said, “Wow, you really still have such a sweet tooth” after she asked it to add chocolate and licorice to her grocery list. Sassy launched alongside three other personalities including Brief, Chill, and Sweet, which are equally cringe in their own ways.
10. Seed rounds, IPOs, & acquisitions
WP Engine acquired WPackagist, a free Composer repository that mirrors WordPress.org's plugin and theme directories, allowing developers to install and manage plugins and themes as dependencies using Composer, for an undisclosed amount. The company plans to continue operating WPackagist as a free service with no disruption to existing users. WPackagist, which was created and maintained by the UK cooperative Outlandish, joins WP Engine's growing portfolio of developer tools, which includes Local, ACF, WP Migrate, and WP Offload Media. In response to the announcement, the official WordPress X account (which is basically Matt Mullenweg's personal account), posted, “The parasite continues to eat the host. The cancer is trying to spread.” And Matt wrote a bitter rant on his blog.
PayPay, the SoftBank and Yahoo Japan-backed payments app, opened 19% above its $16 offer price on its Nasdaq debut, valuing the company at $12.7B after raising roughly $880M in its IPO. PayPay and an investment fund controlled by SoftBank Group sold about 55M shares below the marketed range of $17 to $20 to raise roughly $880M (which they'll likely shove into OpenAI, LOL). The IPO was initially expected in December, but the U.S. government shutdown delayed the regulatory review, and the company decided to push ahead with the offering despite the conflict in the Middle East impacting global markets.
OpenAI acquired Promptfoo, an AI security platform that helps enterprises identify and remediate vulnerabilities in AI systems during development, for an undisclosed amount. The company plans to integrate the technology into OpenAI Frontier to evaluate agentic workflows and perform automated red-teaming. Promptfoo previously raised $23M and reached an $86M valuation in July 2025 and currently provides open source vulnerability testing tools to more than 25% of Fortune 500 companies.
Cursor, the AI coding assistant launched in 2023 that helps developers write, edit, and debug code through natural language commands, is in preliminary talks with investors for a new funding round that would value the startup at approximately $50B, nearly double the $29.3B valuation it secured in its $2.3B round just four months ago. The company's annualized revenue topped $2B in February, making it one of the fastest-growing startups of all time, with backing from Coatue, Thrive Capital, Andreessen Horowitz, Google, and Nvidia. Bloomberg sources say the discussions are preliminary and may not result in a funding deal.
Zendesk entered into a definitive agreement to acquire Forethought, an AI customer service platform that builds self-improving agents for enterprise support, for an undisclosed amount. The addition of Forethought's technology will enable Zendesk's “Resolution Learning Loop” to evolve into fully self-improving AI agents that can autonomously detect workflow gaps, generate new procedures, and execute complex multi-step processes across any channel without manual retraining. Zendesk projects 2026 as the year autonomous AI agents will handle more service interactions than humans, and says its existing agents already resolve over 80% of interactions end-to-end across its customer base.
Eridu, an AI networking startup building custom chips and switches designed to move data faster between GPUs in AI data centers, emerged from stealth and raised $200M in a Series A round led by Socratic Partners, bringing its total amount raised to $230M. The startup is co-founded by Drew Perkins, an engineer who helped create the Point-to-Point Protocol that became a key part of TCP/IP, the protocol upon which the Internet relies. Current data center switches improve at roughly 2-3x every few years, while GPU compute is improving 10x per year, a gap Eridu believes creates an urgent need to rethink networking architecture from the silicon level up.
Alphabet is spinning out GFiber, its formerly Google-owned fiber internet business, by merging it with Astound Broadband in a deal that will make infrastructure investor Stonepeak the majority shareholder while Alphabet retains a significant minority stake. The combined company, which will be led by GFiber's existing executive team, pairs GFiber's high-growth metropolitan fiber networks with Astound's established national infrastructure to create what the companies are calling a leading independent broadband provider. The deal, which is expected to close in Q4 2026 pending regulatory approval, gives GFiber external capital and operational independence and moves it out of Alphabet's “Other Bets” segment, which recorded a $16.8B operating loss in 2025.
Ramp, a fintech that provides businesses with corporate cards, expense management, bill payments, and accounting automation tools, acquired Billhop, a payments platform with licenses in the UK and EU that allows businesses to pay invoices by credit card, even to suppliers that don't accept card payments, for an undisclosed amount. The acquisition gives Ramp the regulatory infrastructure it needs to begin onboarding businesses headquartered in the UK and EU directly, which it plans to do this summer, and will also result in the company opening its first international offices in London and Stockholm. The acquisition follows Ramp's $312M Series E funding round in November, which valued the company at $32B.
Cart.com, a Houston-based e-commerce platform that combines commerce software with a physical fulfillment network, raised $180M from Springcoast Partners, bringing its total equity raised to $660M since it was founded in 2020. The funding will support continued development of its commerce operating system, including workflow automation, predictive analytics, and agentic AI tools designed to autonomously route inventory, reduce shipping times, and lower fulfillment costs for enterprise brands like TOMS Shoes, PacSun, and Janie and Jack. The raise comes as Cart.com looks to differentiate itself by being one of the few commerce platforms to combine enterprise software with a physical logistics network under one roof. Cart.com is the parent company of our sponsor DataFeedWatch.
Meta announced plans to acquire Moltbook, an AI-only social networking platform that allows AI agents to autonomously post, comment, and vote in topic-based communities called “submolts” without direct human participation, for an undisclosed amount. The acquisition brings co-founders Matt Schlicht and Ben Parr into Meta Superintelligence Labs with the goal of exploring “new ways for AI agents to work for people and businesses.” Moltbook was built to run in conjunction with OpenClaw, an open-source AI agent framework created by Peter Steinberger, who was hired by OpenAI a few weeks ago to continue developing the project.
Rox, an AI-powered sales platform that deploys autonomous agents to monitor accounts, research prospects, and update CRM software, raised an undisclosed amount in a round led by General Catalyst at a $1.2B valuation. The company, which was founded in 2024 by former New Relic chief growth officer Ishan Mukherjee, was projected to close 2025 with $8M in ARR at the time the round closed, and has now raised $50M in total prior to this latest round. The startup positions itself as an intelligent revenue operating system that aims to replace and streamline numerous fragmented software solutions currently used by sales teams.
Amazon raised €14.5B in its first-ever euro bond offering, marking the largest corporate deal ever in the euro market. The raise came after investor orders topped €27.9B across eight tranches with maturities ranging from two to 38 years, and followed an 11-part dollar offering earlier in the week that raised $37B, bringing Amazon's total bond raise to over $53B in a single week. The capital will go toward Amazon's previously announced $200B AI infrastructure spending plan for 2026. It's wild to me that investors have enough confidence in a company that's only existed for 32 years to purchase bonds that mature in 38 years.
Google completed its acquisition of Wiz, an Israeli cloud and AI security platform, for $32B, a year after the deal was first announced in March 2025. The acquisition is the largest in Google's history and the largest ever acquisition of a venture-backed startup, with Wiz having crossed $1B in ARR in 2025 before the deal closed. Wiz will join Google Cloud while maintaining its brand and continuing to support all major cloud environments including AWS, Azure, and Oracle Cloud to position itself as the go-to security layer for enterprise customers operating across multiple clouds.
Nvidia announced a $2B investment in Nebius, a full-stack AI cloud platform listed on Nasdaq, as part of a strategic partnership to build out next-generation AI infrastructure for the agentic AI era. Under the partnership, the two companies will collaborate on AI factory design, inference optimization, and fleet management, with Nebius targeting more than 5 gigawatts of deployed capacity by the end of 2030 using Nvidia's latest accelerated computing platforms including the Rubin architecture. The investment follows a string of similar Nvidia bets on AI infrastructure companies that are its biggest customers.
Nvidia also backed Thinking Machines Lab, the AI startup founded by former OpenAI CTO Mira Murati, through a multi-year partnership that includes a significant undisclosed investment and a commitment to procure at least one gigawatt of Nvidia's next-generation Vera Rubin processors starting in early 2027. The deal comes on top of Nvidia's prior participation in Thinking Machines' $2B seed round, which valued the company at $12B.
AMI Labs, a Paris-based AI research startup co-founded by Turing Prize winner and former Meta chief AI scientist Yann LeCun, raised $1.03B in a round co-led by Cathay Innovation, Greycroft, Hiro Capital, HV Capital, and Bezos Expeditions, at a $3.5B valuation. The company is working on “world models,” which learn from real-world experience rather than language data alone, an approach LeCun has long argued is essential to building AI that can reason and plan the way humans do. AMI Labs, which is backed by notable investors including Mark Cuban, Eric Schmidt, and Tim Berners-Lee, has no near-term revenue plans, with CEO Alexandre LeBrun acknowledging the research could take years to reach commercial applications.
Converted, an AI-driven advertising technology company serving emerging markets, acquired Mitcha, an Egyptian e-commerce platform supporting local fashion designers, for an undisclosed amount. The deal integrates Mitcha's designer and customer network into Converted's platform and is expected to accelerate the rollout of Converted Orders, a product that links advertising spend directly to confirmed sales rather than traditional metrics like clicks or impressions. Mitcha founder and Shark Tank Egypt investor Hilda Louca will join Converted as Partner and Executive Director, focusing on strategic partnerships and regional expansion across Egypt and the broader Middle East.
Spark Capital, a venture capital firm that invests in early-stage technology companies including Anthropic, Twitter, Slack, and Warby Parker, is targeting roughly $3B in new funds, a 50% increase from its prior fundraise two years ago, according to The Information sources. The firm led a $450M investment in Anthropic in early 2023 at a $4B valuation, which has grown nearly 100x as Anthropic's valuation has since reached $380B. Its 2022 growth fund, which included the Anthropic investment, is already worth four times the capital invested, while its 2014 growth fund has returned roughly eight times invested capital on a combined realized and unrealized basis.
SupplyOne, a national packaging distributor with more than 60 locations across the U.S. and Canada, acquired Specialty Packaging, a Connecticut-based packaging solutions distributor, for an undisclosed amount. The transaction marks SupplyOne's 47th acquisition since its founding in 1998 and strengthens its footprint across New England. I just covered SupplyOne's last acquisition of Wertheimer Box in January. This company is on an acquisition spree!
Saltz, a Vilnius-based digital marketplace that connects professional kitchens and restaurants directly with food suppliers, raised €20M in a Series A round led by the European Bank for Reconstruction and Development. The company will use the funding to expand its presence across Europe, invest in cross-border food trade infrastructure, and grow its engineering and product teams. Saltz currently operates in 20 countries and works with clients like Hilton and Marriott International, as well as independent restaurant operators.
Yassir, an Algerian super app offering ride-hailing, food and grocery delivery, and digital financial services across Africa, acquired the Uno hypermarket chain from Cevital Group, for an undisclosed amount. The stores are being rebranded as “Yassir Market,” with the flagship Algiers location set to reopen during Ramadan 2026, marking the company's first move into brick-and-mortar retail. Through the acquisition, Yassir aims to build a hybrid shopping experience that combines its existing digital platform with a physical store network, filling a gap left by Jumia's retreat from grocery and hypermarket retail in North Africa.
Syndigo, a product experience management platform that helps brands and retailers manage, syndicate, and optimize product content and data across retail channels and digital shelves, acquired Taggstar, an e-commerce conversion platform that uses real-time social proof messaging such as live views, sales volumes, stock levels, and reviews, to reduce shopper hesitation and increase conversion rates for enterprise retailers, for an undisclosed amount. The acquisition adds dynamic conversion messaging to Syndigo's Product Experience Cloud, allowing retailers and brands to layer real-time shopper context, like “50 bought in the last hour,” on top of existing product content across website, e-mail, social, and digital ad channels.
Verndale, a digital experience and technology company, acquired Homestead Studio, a D2C acquisition and retention agency, for an undisclosed amount. Homestead specializes in lifecycle marketing, email and SMS, segmentation, automation, and performance optimization, and was named Klaviyo's 2025 Americas Agency Partner of the Year. The acquisition follows Verndale's recent acquisition of Vaan Group and is part of the company's broader strategy to build a full-funnel D2C growth platform covering everything from platform strategy and experience design to customer acquisition, retention, and revenue optimization.
inDrive, a global ride-hailing and gig services platform that allows passengers and drivers to negotiate fares directly, acquired Krave Mart, a Pakistani quick-commerce startup that delivers groceries and everyday essentials to urban customers, for an undisclosed amount. The all-stock deal builds on a prior investment inDrive made in Krave Mart in December 2024 and a subsequent partnership that launched grocery delivery under the inDrive.Groceries brand in Lahore earlier this year. Both the Krave Mart and inDrive brands will continue to operate in Karachi as the company works to expand grocery delivery across Pakistan, where it is already the most downloaded ride-hailing app.
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PS: The very first French Fries weren't actually cooked in France. They were fried in Greece.