Hi Shopifreaks
How'd your Super Bowl Sunday go? Did you bet your life savings on the Seattle Seahawks winning like that one TikToker did? Actually that didn't turn out to be such a bad idea…
This week I've got an incredible edition for you covering everything from PayPal's decision to fire their CEO to this year's best Super Bowl commercials. It's a jam-packed edition (even more so than usual), so let's dive right in…
In this week's edition I cover:
- PayPal's leadership shakeup
- Shopify's redesigned Shop App
- Unprecedented capex spending in 2026
- Germany's battle against Amazon
- TikTok's alleged “autopilot mode”
- Anthropic's Super Bowl ad hit a nerve
- This year's best Super Bowl commercials
- Spotify's partnership with Bookshop
- USPS launches a pre-paid duty service
- The DOJ wants harsher penalties for Google
- And a $44B Bitcoin giveaway? Oops!
All this and more in this week's 264th Edition of Shopifreaks. Thanks for subscribing and sharing!
Stat of the Week
Only 2.6% of China's total foreign direct investment in 2025 went to North America, significantly down from 27% a decade ago, according to Rhodium Group, which says geopolitical tensions between the U.S. and China are the reason for the decline. After years of increased scrutiny and export controls on Chinese goods and services, Chinese companies now view the U.S. as unpredictable and volatile, and are choosing to fund projects in politically friendly or neutral countries instead.
1. PayPal replaces Alex Chriss with Enrique Lores as its CEO
PayPal announced the appointment of Enrique Lores as its new President and CEO, effective March 1, 2026. Lores has served on the PayPal Board for almost five years and as Board Chair since July 2024 and most recently led HP as President and CEO for six years. CFO Jamie Miller will step in this month as interim leader until Lores takes the role.
Why fire Alex Chriss?
The board wrote in its announcement:
“While some progress has been made in a number of areas over the last two years, the pace of change and execution was not in line with the Board's expectations.”
The board also pointed to slower growth of PayPal's legacy branded checkout as a reason for the dismissal.
Firing Alex Chriss was a mistake in my opinion.
“Oh no, our precious stock price wasn't incrementally growing.” Yeah, but it also leveled off during his tenure, unlike the 3 years prior when it fell off a cliff! That's got to be worth something, right? Did they expect an 18 month turnaround back to $300?
Can you give the guy a minute to first clean up the disaster he inherited and then execute his new vision? And no, “2 years and 4 months” isn't a long enough “minute” in my book. Especially when talking about a company that had innovationally been neglected for a decade prior.
Since September 2023, Chriss had:
- Launched a media network, positioning PayPal to leverage its decades of consumer and merchant data to enter the high-margin business of advertising. Didn't get a chance to see this through.
- Positioned PayPal to become the de facto digital wallet of agentic shopping via partnerships with OpenAI, Google, and Microsoft. Didn't get a chance to see this through.
- Became a merchant processor in Shopify Payments, rather than just a third-party checkout option, taking a slice of the pie from Stripe for the first time ever in Shopify's history. Didn't get a chance to see this through.
I could list more than that, but just wanted to highlight a few key verticals he put roots down in.
Meanwhile the board is like, “but payment-volume growth in branded checkout slowed to 1% during the recent quarter.”
No shit! Competitors have been coming to the table to eat PayPal's lunch for the past two decades in that space, and it's caught up with them. Why do you think Chriss was transitioning PayPal towards being the backbone of commerce instead of just a consumer-facing digital wallet?
In the words of Kanye West, “Can I finish? Can I finish?”
❌ Focusing on quarterly stock growth = shortsighted
✅ Positioning PayPal for the AI / Shopify / Google / Apple dominated commerce future = forward thinking
Jeff Bezos famously didn't care about Amazon's stock price and practically mocked investors who did. Companies that are so ultra-focused on quarterly growth lack the vision that's needed to compete in this industry during the next two decades.
Replace the BOARD, not the CEO!
This isn't to say that Enrique Lores can't / won't do a good job running PayPal. My commentary above is about my optimism for Chriss's leadership, not my lack of faith in Lores's. I'm just disappointed in PayPal for not letting Chriss see it through, as is the market apparently.
PayPal needed a decade-CEO, not a quarterly-CEO, and they had one.
What are your thoughts? Hit reply and let me know or join the conversation on LinkedIn.
2. Shopify redesigns the Shop App home feed
Shopify redesigned the home feed of its Shop App to create a swipeable shopping experience, curated for each shopper based on their interests and the brands they follow.
President Harley Finkelstein wrote:
“The experience has been fully redesigned. Virtual window-shopping, curated for each individual shopper. Shopping should feel immersive. It should tell a story. It should feel inspiring. With the new feed, we’re putting shoppable video front and center. That means: More storytelling. More personality. Shop has always been about making buying easier and selling simpler. Now it’s becoming something more. We're making Shop the definitive destination for discovery. And it looks incredible.”
Does it actually look incredible?
For now, I give it a solid “meh” because it just feels like a swipeable product grid without the entertainment. In order to turn Shop App into an actual TikTok Shop-like discovery-focused shopping experience — if that's what they want to do — it needs merchants to upload short form videos, and that might take some incentivizing.
Wait, but doesn't the feed “put shoppable video front and center”?
Yes, but every video I saw was either a product shot video without a story or Shopify merely placing a vertically cropped version of the merchant's cover video behind a carousel product grid. That's not the type of video content that keeps people swiping.
This current version of Shop App feels less like “storytelling” and “personality” and more like “swiping through thumbnails of products I'm not interested in.”
Also, while we're talking about the UI: Shopify, why is there a permanently affixed back button on the home feed in the bottom left corner that leads to nowhere? Hide that button until I click forward. And where did the Search bar go? Search is out, videos are in?
Remember when Amazon tried to build a TikTok clone?
Amazon launched the Inspire feed in September 2022, which featured vertical TikTok-style short-form video feed within the Amazon mobile app to help drive product discovery. The new Shop App home feed feels like a worse version of that.
Inspire eventually shut down over lack of interest. Turns out people don't just want to scroll shopping videos all day. They like them mixed into their entertainment content as well.
Back then I wrote about Inspire:
“A big difference though between Inspire and those other apps is that users are gravitating towards TikTok and IG for all sorts of entertainment — not just shopping — and then discovering products as part of the overall experience. Whereas Inspire is a predominantly product-based feed with no other types of entertainment.”
It feels that the Shop App has followed a similar path as Inspire, and may be headed towards the same fate. Not to say that the Shop App is going anywhere, as it serves multiple purposes, but I don't imagine that the home feed will look like this a year from now, as it's not a good experience.
3. Big Tech plans to go wild on capex in 2026
Alphabet, Amazon, Meta, and Microsoft have collectively forecast capital expenditures that will reach $650B in 2026, with most of the increases earmarked for new data centers and other AI endeavors. Each company estimates that this year's capex spend will either near or surpass their budgets for the past three years combined, setting a high-water mark for capital spending by any single corporation in any one of the past 10 years, according to Bloomberg data.
- Meta said full year capex will rise to as much as $135B, a potential 87% increase.
- Microsoft reported a 66% increase in Q2 capital spending, with estimates projecting the company to shell out $105B for the fiscal year ending in June.
- Alphabet plans to spend as much as $185B, compared with the $119.5B analysts expected, and up from $91.4B in 2025.
- Amazon reported a planned $200B in capex for 2026, up from $131.8B last year.
The four companies lost over $950B in market value since releasing their latest earnings and outlooks, while shares of companies like Nvidia, AMD, and Broadcom, which make the hardware, increased.
Bloomberg's Matt Day and Annie Bang wrote:
“The sprint to build these sprawling facilities, which hold racks of humming servers powered by expensive processors, has touched off an unprecedented level of borrowing, pinched energy supplies and brought developers into conflict with communities worried about rising power and water costs. It also raises the risk that expenditures by a narrow set of affluent companies, already accounting for a rising share of economic activity in the US, could distort big-picture data such as construction spending, gross domestic product, durable goods and employment reports, potentially making the overall economy look healthier than it actually is.”
You might find this interesting…
Analysts estimate that 25–40% of Microsoft’s AI infrastructure spend is OpenAI-related, fulfilling datacenter and processing commitments it made to the company, which has simultaneously committed to spending $250B on Microsoft Azure cloud services.
I'm curious to know how much capex is being spent across the industry to fulfill the hundreds of billions of dollars in commitments that OpenAI has made to various partners including Microsoft, Oracle, Broadcom, Nvidia, AMD, Amazon, CoreWeave, and Google. And what happens to those data centers if OpenAI can't come through on those commitments?
Will datacenters be the shopping malls of 2036? That'll be a lot of Halloween Superstores.
4. Amazon fined €59M by German antitrust officials
German antitrust officials fined Amazon €59M ($69.7M) for using price-filtering tools that suppress third-party listings. Regulators said the tools effectively let Amazon influence seller pricing by limiting visibility of offers deemed “too expensive,” causing merchants to miss out on sales and violating competition law.
Andreas Mundt, President of the country's Federal Cartel Office, said:
“Amazon is not allowed to restrict the visibility of legally permissible offers from Marketplace sellers or even remove them entirely simply because their prices are not in line with its expectations.”
Rocco Braeuniger, the country manager for Amazon Germany, noted that Amazon would be the only retailer in Germany forced to promote anticompetitive prices to customers because of the decision, which he says directly conflicts with competition law consumer standards in the European Union.
Why just Amazon?
Germany sees Amazon as a gatekeeper, not a normal marketplace, and has designated the company as one “of paramount significance for competition.” In other words, sellers depend on Amazon to reach consumers in the country. It's not just another store or marketplace.
Germany believes that competitive pricing should come from market forces, not from the platform punishing lawful prices. Basically, it wants to enforce that Amazon can recommend cheaper offers, but it cannot coerce sellers into pricing decisions by threatening their visibility, which is a fair argument to make. It's estimated that Amazon controls over 60% of Germany's e-commerce market, which one could argue effectively makes it “the market.”
Amazon claims each selling partner is free to set their own prices, shipping fees, and return policies. It is appealing the decision, arguing that the ruling will force the retailer to promote uncompetitive prices to consumers, which is also a fair argument. Why should Amazon have to surface listings with higher prices than customers may find on other stores or marketplaces?
Honestly, I'm split on this one. Where is the line drawn between Amazon surfacing the best deals and influencing seller prices by doing so? I'm guessing this case aims to find out.
What are your thoughts? Hit reply and let me know.
5. EU accuses TikTok of putting users in “autopilot mode” and demands changes
The European Commission stated in a preliminary ruling that TikTok’s infinite scroll, auto-play features and recommendation algorithm amount to an “addictive design” that violates EU laws for online safety and poses potential harm to the “physical and mental well-being” of users.
European regulators are accusing the platform of shifting users into “autopilot mode” and are considering mandatory changes such as disabling infinite scrolling, creating new screen-time limits, and changing its recommendation system. They also accuse the company of disregarding signs that its app was being used compulsively, including the frequency users open the app and the amount of time minors spend on the platform at night.
The Commission wrote in a statement:
“By constantly ‘rewarding’ users with new content, certain design features of TikTok fuel the urge to keep scrolling and shift the brain of users into ‘autopilot mode.’ Scientific research shows that this may lead to compulsive behaviour and reduce users’ self-control.”
TikTok does offer parental controls and screen-time management tools, but the Commission says those tools don't do enough to reduce the risk of its addictive design “because they are easy to dismiss and introduce limited friction.”
TikTok denies the allegations and said:
“The Commission’s preliminary findings present a categorically false and entirely meritless depiction of our platform, and we will take whatever steps are necessary to challenge these findings through every means available to us.”
TikTok now has a chance to respond to the allegations, but if not successful with its appeal, faces potential fines up to 6% of its global revenue for violating the EU's Digital Services Act.
6. Anthropic's Super Bowl ad hit a nerve with Sam Altman
By now you've seen Anthropic's Super Bowl ad for Claude, right? If not, watch it here.
- The commercial begins with the word “BETRAYAL” written across the screen, and then features a man asking ChatGPT for advice on how to talk to his mom.
- The chatbot, depicted by a middle-aged blonde woman, starts by offering some decent advice like “start by listening” or “go on a nature walk.”
- Then she suddenly pivots into an advertisement, recommending that he find emotional connection with other older women on a fictitious dating website called Golden Encounters.
- The commercial finishes by saying “Ads are coming to AI. But not to Claude.”
Anthropic also released three other commercials including:
- VIOLATION: A man asking ChatGPT how to get a six-pack. The chatbot begins creating a personalized workout plan for him, and then pivots to ad-mode and pitches shoe insoles for “short kings.”
- DECEPTION: A woman asks ChatGPT for feedback on her business idea. The chatbot tells her it's a great idea and offers to create a business plan. Then it pivots into an ad for Quick Dash Payday Loans because “girl bosses need SHE-E-O money quick.”
- TREACHERY: A student asks ChatGPT if her essay is making a clear argument. The chatbot praises her argument and essay, and then pivots into ad-mode for a jewelry store, telling her to “cherish this unforgettable occasion” of her essay being due.
These are some of the best ads attacking a competitor that I've seen in a long time! I love a good company-vs-company beef. However not everyone appreciated the commercials as much as me.
Sam Altman posted a 2,306 character rant on X, which I'll highlight quotes from below:
- “First, the good part of the Anthropic ads: they are funny, and I laughed.”
- “But I wonder why Anthropic would go for something so clearly dishonest. Our most important principle for ads says that we won’t do exactly this; we would obviously never run ads in the way Anthropic depicts them. We are not stupid and we know our users would reject that.”
- “More importantly, we believe everyone deserves to use AI and are committed to free access, because we believe access creates agency. More Texans use ChatGPT for free than total people use Claude in the US, so we have a differently-shaped problem than they do.”
- “Anthropic serves an expensive product to rich people. We are glad they do that and we are doing that too, but we also feel strongly that we need to bring AI to billions of people who can’t pay for subscriptions.”
What's funny about his response (but not as funny as Anthropic's videos) is that he criticizes Anthropic for “serving an expensive product to rich people,” which I assume he's referencing their enterprise-focused business model, while simultaneously building out his enterprise division to compete with them in the space!
Read the replies on Altman's X post where users just absolutely roasted him. His defensive essay wasn't well received.
7. Highlights of this year's best Super Bowl commercials
Anthropic definitely won the Super Bowl this year, but let's take a look at some other commercial highlights from companies we follow.
- Amazon Alexa+ – Chris Hemsworth holds snakes, fights bears, survives drowning and an exploding house, but fears AI, until it starts making his life easier. I liked that Amazon addressed consumer fears of having AI in their homes in a playful way.
- Ring – Another Amazon spot that showcases Ring doorbells and cameras' abilities to use AI to help find lost pets in the neighborhood. Boring commercial, but a cool feature I didn't know about.
- Meta AI – Meta showcases its “athletic intelligence” through extreme use cases of its Oakley smart glasses with people jumping out of airplanes, skateboarding, mountain biking, and break dancing. Cool, high-energy commercial that showcased their smart glasses' ability to record footage, play music, and answer questions on the go.
- Google Gemini – Google went the heart-warming route this year, featuring a mother and daughter designing the child's bedroom and creating an outdoor garden space with Nano Banana image simulations. Honestly, it was a super cute ad, but maybe I'm just a sappy dad now.
- Ramp AI – Imagine an office full of Kevin Malones! Ramp's commercial said, “Multiply what's possible,” and featured a fictitious office full of Kevins doing work, ending with two Kevins carrying a pot of chili. As an Office fan, I of course loved this one. Although they missed the opportunity for him to say, “Why waste time use lot of AI when Ramp do trick?” Maybe that'll be for his next spot.
- Ripple – As soon as I saw Tim Robinson, I was in, but then Ripple lost me because their commercial was boring. Why did they feature a toned down version of Robinson? They should've let him go into full character.
- Wix – Wix went full-on inspirational this year showcasing how easy it is to build websites on their Harmony platform. This was a swing and a miss in my opinion, and the commercial could've featured any AI website builder. It wasn't a memorable spot.
- Xfinity – They went the nostalgic path this year with a Jurassic Park remake where an Xfinity technician gets the park back online before the dinosaurs take over. “That could've been bad.” Pretty funny! I didn't LOL, but I definitely expelled air from my nostrils at a higher velocity than usual.
- Squarespace – They usually make pretty good commercials, but their Super Bowl spot had some steep competition this year. This one featured Emma Stone in an old-school horror movie attempting to buy EmmaStone.com, but having the domain unavailable. The commercial ended with “Get your domain before you lose it.” The actual website is an extension of that ad, which was a fun detail.
- Instacart – The groceries platform enlisted Ben Stiller to sing in a 1980s-themed band about “Instacart letting you choose your bananas.” It was okay, but I doubt the song will go viral.
- Grubhub – Their commercial showed a group of wealthy people sitting around at a dinner table arguing about who's going to eat the fees, which were depicted as the final course of the meal, only for George Clooney to appear and say, “Grubhub will eat the fees.” The commercial ended with a promo for “No fees on restaurant orders over $50.” I admit that my first thought was, “Wait, Grubhub will eat the fees? Or the restaurants will eat the fees?”
What was your favorite Super Bowl commercial this year? Hit reply and let me know!
8. Spotify partners with Bookshop.org to sell physical books
Spotify announced a partnership with Bookshop.org to sell physical books directly within its streaming application, expanding beyond its audiobook business, which it launched two years ago and now has over 500k titles. The feature will roll out in the spring for U.S. and U.K. users, with Bookshop handling pricing, inventory, and fulfillment, and Spotify receiving an affiliate fee for purchases made within the app.
What is Bookshop.org? The online bookstore launched in 2020 as an Amazon alternative with a mission to support local, independent bookstores by allowing customers to choose their favorite local bookstores to receive the profit from their online purchases. So far it says it's raised over $45M for local bookstores.
Bookshop.org also offers a healthy 10% commission to affiliates (maybe more for Spotify, I'm not sure), versus Amazon's 4.5% commission, which makes it an attractive partner.
The only catch? Their books are more expensive.
A few years ago I did a study comparing the price of the 50 Best Selling Titles on Amazon to their sale price on Bookshop, and I discovered that Bookshop was 58% more expensive on average per title than Amazon. While I support Bookshop's mission, ultimately customers are paying the price.
Of course, Spotify couldn't exactly partner with Amazon, as they are a direct competitor in music streaming and audiobooks, so I'm glad they chose Bookshop.
By the way, you might not know this about me, but I wrote a book several years ago called Capital Cities: A Journey Around The World Through 118 Capital Cities in collaboration with 60 other travelers, which is for sale on Bookshop.org.
9. Other e-commerce news of interest
Google's Chief Business Officer Philipp Schindler said on a recent earnings call that the company is “in the early stages of experimenting with AI Mode monetization, like testing ads below the AI response, with more underway.” Regarding Google's new Direct Offers pilot program, Schindler said, “We announced Direct Offers, a new Google Ads pilot, which will allow advertisers to show exclusive offers for shoppers who are ready to buy, directly in AI mode.” The company also plans to launch checkout directly within AI Mode from select merchants to start. Schindler also noted that the longer AI Mode queries are creating new ad inventory, and that Gemini's understanding of intent “has increased our ability to deliver ads on longer, more complex searches that were previously challenging to monetize.”
TikTok launched a new U.S.-focused Smart Promotion Program that boosts product visibility on TikTok Shop in exchange for seller-funded promotions, guaranteeing earnings of at least $5 in GMV for every $1 vendors spend through the end of the month. Eligible sellers must meet performance thresholds, including maintaining a Shop Performance Score of at least 3.5 out of 5, and contribute marketing dollars that TikTok allocates across coupons, discounts, and in-app placements. TikTok wrote in its announcement, “The platform manages all investment in this Program, aiming to maximize sellers' ROI with the support of advanced algorithms.”
USPS launched a new service for shippers who send goods internationally called USPS Delivered Duty Paid, enabling the sender to prepay import duties, taxes, and fees under the destination country's requirements at the time of mailing. The agency decided in November to create the service to address recent challenges mailers are facing related to tariffs, removing surprise fees from the equation. The service is currently available for packages going to Canada, Germany, and the U.K., with plans to expand to other countries in the future.
Amazon set a new delivery speed record in 2025, with over 13B same-day or next-day deliveries worldwide, marking its fastest performance ever and third consecutive year it has broken its record. Prime members in the U.S. received over 8B same or next-day deliveries, marking a more than 30% increase from 2024, with groceries and everyday essentials accounting for about half of those orders. Good lord you guys order a lot of Amazon packages in the US! Down here in Ecuador, “online shopping” often means asking people in a Facebook Group where to find an item, and then driving to three small stores to get it, because the first two didn't have it.
The Department of Justice and a group of U.S. states appealed a judge's ruling on how Google's search business should change following an earlier finding that it was an illegal monopoly. In the recent ruling, the judge rejected more extreme proposals like banning Google from paying for search distribution or forcing it to sell its Chrome browser in favor of less destructive remedies such as prohibiting exclusive distribution deals and mandating limited data sharing with rivals. However the DOJ doesn't feel that those remedies are severe enough. Google also appealed the judgement two weeks ago, albeit for different reasons, and is currently seeking to pause the mandated data sharing requirements while the cross-appeals move through the courts.
Walmart surpassed a $1 trillion market capitalization on Tuesday, becoming the first traditional retailer to join the 4-comma valuation club. The achievement places Walmart among a small, but growing group of companies that have 13-figure valuations including Amazon, Nvidia, Meta, and Microsoft. Walmart's stock has surged in recent months in part due to Wall Street's enthusiasm for its growing online business, as well as its investments in automation and AI technology aimed at improving efficiency. Its e-commerce business became profitable as a stand-alone unit for the first time last year, which investors had been waiting for.
Etsy is testing new quality-related badges in search results, including “crafted with care” and “high craftsmanship,” applied to a limited set of listings as part of an ongoing experiment. Etsy confirmed the labels are meant to help buyers better understand items they’re browsing, with selection influenced by multiple factors and partially driven by AI rather than a single clear rule. E-commerce consultant Cindy Baldassi thinks that the experiment is less about actually determining quality and more for learning how shoppers respond to items with certain phrases in front of the listing, to see if they increase conversions.
eBay introduced Item Compare in search, a new feature that allows buyers to compare up to three listings without leaving the results page. However Liz Morton of Value Added Resource notes that early testing shows inconsistent data pulls and limited functionality. Morton wrote that “seeing Item Compare live makes it clear that not only is eBay still lagging far behind other marketplaces when it comes to product discovery, they clearly have not solved basic problems of data analysis and mapping to identify and display the correct information in a side by side comparison across multiple listings.” She also warns that buyers interacting with products using this new Item Compare module will trigger attribution for Promoted Listings, resulting in ad fees being charged. Yikes, eBay!
The Consumer Financial Protection Bureau updated its consumer complaint portal to strongly steer users toward disputing issues directly with credit bureaus before contacting the agency, warning that complaints may be rejected if that step is skipped. The new flow requires consumers to wait up to 45 days after filing with a bureau and to attest they followed the process. The changes follow pressure from Equifax, Experian, and TransUnion, which allege that the complaint portal is being abused by third-party credit repair firms and AI bots. The credit bureaus also want the CFPB to implement two-factor authentication, restrict the number of complaints that can be filed per phone number, and limit the ability of a single IP address to submit complaints on behalf of multiple consumers. Wait, so rather than fix the reason consumers are filing complaints, the solution is to make it harder to complain?
Stripe paused the launch of a new stablecoin card product after scammers exploited the rollout, forcing the company to suspend a crypto client’s program and tighten controls, according to internal messages read by The Information. The problems surfaced after Stripe’s $1.1B acquisition of Bridge last year, which integrated stablecoins into cards and payments but also exposed Stripe to higher fraud, sanctions, and banking partner risks. Since the incident, Bridge has restricted customers from high-risk regions such as Venezuela as part of Stripe's attempt to balance stablecoin growth against compliance and fraud exposure.
Amazon reported that its U.S. corporate income taxes declined by more than half in 2025, even as pretax profits surged nearly 45%, as a result of new legislation signed by President Trump that permitted immediate deductions for capital investments and research expenses. The company said it paid $2.8B in federal cash taxes, down from the roughly $7B it paid in the previous two years. However Amazon noted, “Deducting our costs more quickly provides a short-run benefit but this policy ultimately doesn’t change the amount of tax we pay. It just changes the timing of our tax payments.”
Amazon is rolling out Alexa+ to all U.S. users after nearly a year in early access, pricing it at $19.99 per month, or free for Prime members. Good move Amazon, because it's felt like the Prime membership has been losing value in recent years, with grocery delivery fees increasing and the addition of $2.99 per month for an ad-free experience on Prime Video. The subscription needed a value-boost. Alexa+ now runs across Echo devices, the Alexa app, and a new web interface, and adds agent-style capabilities like booking services, shopping, and handling multi-step requests. Amazon says usage and engagement have increased since the rollout, though I reported a few weeks ago that some users are switching back to the old Alexa because they don't like the new Alexa's voice and attitude or they experience longer wait times for answers.
Zip launched a new pay-in-2 option for U.S. customers, letting shoppers split purchases into two equal payments over two weeks instead of the standard four-installment BNPL model. The company says the option is aimed at everyday spending like groceries and bills, following a pilot where 95% of surveyed users said they would use the pay-in-2 option again. Why stop at two? How about letting customers pay for their purchases in just one installment? Oh wait…
Google's Gemini chatbot surpassed 750M monthly active users, according to the company's fourth-quarter earnings, up from 650M the quarter before. In comparison, Meta reported 500M users and OpenAI estimates 810M. The recently revealed number follows the launch of Gemini 3, which Google claims is its most advanced model to date. Google recently rolled out a more affordable plan called Google AI Plus for $7.99/month to help drive further AI growth with budget-conscious users. Got to have a cheap plan for users who want to go ‘ad-free' in the future!
eBay is launching a new monthly eBay for Sellers Webinar Series, tapping Seller Circle hosts and internal product managers to run one-hour deep dives on ads, seller tools, and AI. The first session on February 19 will focus on planning 2026 eBay Ads strategy and comes as sellers push back on recent Promoted Listings attribution changes that have driven higher fees and unclear ROI. A second webinar scheduled for March will cover store enhancements and AI tools
Amazon is negotiating a commercial agreement with OpenAI that would grant it special access to customized AI models for products like Alexa, according to The Information sources. The potential deal coincides with discussions regarding a multibillion-dollar equity investment in OpenAI and aims to bypass restrictions Amazon currently faces with Anthropic by securing dedicated engineering resources from OpenAI. It's getting weird that every competing AI company has an investment or working relationship with OpenAI, isn't it? I'm curious how this will all end.
In other OpenAI news… The AI firm launched Frontier, a centralized platform designed to help businesses build, deploy, and manage AI agents, as part of its efforts to grow its enterprise business. OpenAI says that Frontier “gives agents the same skills people need to succeed at work: shared context, onboarding, hands-on learning with feedback, and clear permissions and boundaries,” and that it's currently being adopted by HP, Intuit, Oracle, State Farm, Uber, and other enterprise companies. OpenAI also launched a desktop application for its Codex coding tool to challenge Anthropic. The new interface is designed to help users manage multiple AI agents simultaneously for complex tasks like information analysis.
Adobe announced plans to discontinue its 2D animation software, Adobe Animate, on March 1, 2026, retiring the 25-year-old product without offering a direct replacement. The decision sparked outrage among the creative community who expressed concern about the lack of alternatives that mirror Animate's functionality. Two days after the announcement, Adobe reversed its decision, and says it plans to continue to make Animate available for current and new customers. Meh, I don't trust them. Who wants to bet that Animate isn't around a year from now?
Meta is testing a standalone version of vibes, its AI-generated video feed, in Brazil and Mexico. Until now, the Vibes feed, which launched last September, lived within the Meta AI app, but now the company aims to better to compete with OpenAI's Sora app, which is separate from the ChatGPT app. Meta says that Vibes has been getting strong early traction within Meta AI and that users are “increasingly leaning into the format to create, discover, and share AI-generated video with friends.”
Mozilla is adding a new “AI control” switch to its Firefox browser on Feb 24th, allowing users to enable or disable the browser's current and future AI features such as built-in chatbots, translations, and AI tab groups. Over the past year, Mozilla has doubled down on developing AI features, which has led to backlash by many users, prompting the new kill switch. It sounds like Mozilla became aware of another “kill switch” available called “switching browsers.”
In layoffs this week…
- Amazon is offering workers at its Amazon Fresh stores severance pay, or the option to apply for a transfer within its grocery business, as it shuts down the supermarkets, as I reported last week.
- The Washington Post laid off one-third of its staff, eliminating its entire sports department and closing its books desk, as well as reducing its roster of overseas journalists and suspending the “Post Reports” podcast. Jeff Bezos, who bought the newspaper in 2013 for $250M and could easily give it a capital injection in 2026 to continue operations as-is, declined to comment.
- Pinterest fired two engineers who the company claims created a script to identify and expose the names of workers affected by recent layoffs, which impacted 15% of its workforce. CEO Bill Ready said, “Healthy debate and dissent are expected, that’s how we make our decisions, but there’s a clear line between constructive debate and behavior that’s obstructionist” — a word he likely got from AI. Other Pinterest employees disputed the company's characterization of the incident, claiming that the engineers merely posted instructions showing how to prompt the company's staff directory to show who was laid off, and that they didn't create custom software.
- Peloton slashed 11% of its staff, mostly impacting “engineers working on technology and enterprise-related efforts.” The cuts follow last year's launch of new AI-powered bikes and treadmills, which didn't sell very well.
- Block notified hundreds of employees that their jobs may be eliminated during annual performance reviews as the company embarks on a broader business overhaul. Anonymous insiders said that up to 10% of the company's 11,000-ish employees could be impacted.
In corporate shakeups this week…
- Kroger hired Greg Foran, who previously headed Walmart's U.S. unit, as its new CEO. The grocer has been searching for a permanent CEO after it ousted Rodney McMullen last year following an investigation into his personal conduct.
- Saks Global brought back Cheryl Han, who left the company in August, to serve in a newly created dual role, chief marketing and digital officer. Han will oversee the company's “end-to-end marketing strategy and execution” and e-commerce businesses.
- Walmart's OnePay appointed Patrick O'Connel as its new CFO. O'Connel joins the company from AMC Networks, where has served as executive VP and CFO since 2022, and previously held positions at Goldman Sachs and CBS.
- Fandom named Jay Sullivan, a former Twitter and Facebook executive, as its new CEO, as the company aims to evolve its platform with AI.
- Amazon CEO Andy Jassy picked Dharmesh Mehta to be his new “shadow” advisor, a highly coveted role historically served by advisors who go on to assume greater leadership roles inside the company. For example, Jassy served as Jeff Bezos' shadow in the early 2000s.
- Apple lost four more of its AI researchers and a Siri executive. Yinfei Yang left to start a new company, Haoxuan You and Bailin Wang joined Meta, and Zirui Wang and Stuart Bowers joined Google DeepMind.
- OpenAI hired Dylan Scand, an Anthropic safety researcher, as its first head of preparedness, a new role that generated buzz online last month for its $555k annual salary.
OpenAI accused xAI of “systemic and intentional destruction” of evidence in a lawsuit Elon Musk’s companies filed claiming OpenAI and Apple blocked competition in AI markets. OpenAI claims that xAI has failed to turn over internal documents because it directed employees to use “ephemeral messaging tools” that auto-delete communications after a certain period of time, even though it knew litigation was coming, leaving OpenAI and Apple “at an inequitable disadvantage.” OpenAI is seeking a court order to halt the practice and is requesting a forensic inspector to investigate the missing data.
Senator Elizabeth Warren is probing Google for information about its plans to build a checkout feature into Gemini. In a letter to CEO Sundar Pichai, Warren expressed her concerns that the integration could allow Google and retailers “to exploit sensitive user data” or “manipulate consumers into spending more and paying higher prices.” Specifically Warren asked questions about user privacy and how user data will affect pricing. Google has until Feb 17th to respond, though it has already publicly denied claims that it plans to use its newly launched Universal Commerce Protocol for “surveillance pricing.”
French police raided the Paris offices of X as part of an investigation opened in January 2025 over the production of “sexual deepfakes” by Grok and other crimes. The cybercrime unit is coordinating the search with Europol and the French Gendarmerie nationale, a branch of the country's armed forces. X said that the allegations were “baseless” and accused the Paris Prosecutor's Office of “attempting to exert pressure on X's senior management in the United States,” while Musk described it as a “political attack.” Elon Musk, former X CEO Linda Yaccarino, and other X employees have been sent summons for hearings in April.
France is banning public officials from using U.S. videoconferencing tools like Google Meet, Zoom, and Microsoft Teams, requiring them to switch to Visio, a government-built platform hosted on French infrastructure. The move is part of a broader push in the country to reduce reliance on U.S. tech providers and follows earlier efforts to replace the use of WhatsApp and Telegram with the government-run messaging app Tchap. Prepare yourself, because this is just the beginning. In the next decade, Europe and other regions are going to make concerted efforts to end their dependency on U.S. Big Tech and replace it with their own homegrown platforms. The movement has already started.
Spain is planning to ban teenagers under 16 from using social media, becoming the first European country to follow in the footsteps of Australia, which made the shift in December. Prime Minister Pedro Sanchez said that “platforms will be required to implement effective age-verification systems — not just checkboxes, but real barriers that work.” The country has yet to define which platforms are affected by its new rules, and it'll be interesting to see how their definition of “social media” compares to Australia's.
Y Combinator announced it will resume investing in Canadian-incorporated companies following a sudden policy reversal, which I reported on last week. The firm restored Canada to its list of accepted jurisdictions after receiving strong feedback from the founder community regarding the exclusion. CEO Garry Tan acknowledged that while U.S. incorporation often aids fundraising, the accelerator is committed to supporting Canadian entities without forcing them to restructure. Since YC launched in 2005, just 144 of the 5,664 startups that have gone through the program were incorporated in Canada.
An Amazon delivery drone crashed into an apartment building in Richardson, Texas and then plummeted to the ground in a ball of smoke, though firefighters confirmed it never actually caught fire. The incident was captured by a local resident on video, which shows the MK30 hexacopter hovering extremely close to the multi-story complex before its propellers struck the facade. This is the third Amazon drone accident in the last 5 months.
Amazon's documentary “Melania” about the First Lady is expanding to 300 more theaters after a better than expected opening weekend. Actually, make that 299. Amazon pulled the film from one Oregon theater for making jokes on its marquee like, “Does Melania wear Prada? Find out Friday.” After canceling the airing of the documentary, the theater updated its marquee to read, “Amazon called. Our marquee made them mad. All Melania showings cancelled. Show your support at Whole Foods instead.”
🏆 This week's most ridiculous story… A South Korean cryptocurrency exchange accidentally gave away $44B worth of Bitcoin to customers as part of a promotion that went incredibly wrong. The original plan was to distribute small cash awards of 2,000 Korean won to each user, which is worth about $1.40, but winners instead received 2,000 BTC each. The company said it was able to recover 99.7% of the 620,000 Bitcoins it gave away to 695 customers, but that still leaves $132M worth of Bitcoin that got away.
10. Seed rounds, IPOs, & acquisitions
SpaceX acquired xAI, combining Elon Musk's rocket and satellite business with his AI startup, via a share exchange deal that values the combined company at $1.25 trillion. Musk wrote that the merger will “form the most ambitious, vertically-integrated innovation engine on (and off) Earth.” The deal valued xAI at around $250B, according to WSJ sources. The combined company plans to deploy an orbital AI data center network consisting of up to one million satellites if it can secure permission from telecommunications authorities.
Privy, an e-mail and SMS marketing platform built for e-commerce brands, acquired Sendlane, a competing e-mail and SMS platform, for an undisclosed amount. The deal brings Sendlane’s marketing tools and service-heavy customer support under Privy’s platform, adding lifecycle messaging to Privy’s core onsite conversion products. Privy says existing customers on both platforms will see deeper automation and more unified reporting over time.
ElevenLabs, an AI voice tech company that creates realistic text-to-speech, voice cloning, and conversational audio tools, raised $500M in a Series D round led by Sequoia Capital at an $11B valuation, marking a more than 3x valuation increase since its last round in January 2025. The raise follows a year during which the company generated over $330M in annual recurring revenue and is set to fund the expansion of its enterprise agent platform, research into emotional conversational models, and expansion into international markets. Sequoia partner Andrew Reed is joining the company’s board.
Linq, a startup building tools that let AI assistant live natively inside messaging apps like WhatsApp, iMessage, and Slack, raised $20M in a Series A round led by TQ Ventures. The company pivoted from sales messaging tools to AI infrastructure after demand surged from AI assistants that wanted to operate directly inside consumer messaging apps, as opposed to being limited to their own standalone apps. Linq says it now processes more than 30M messages per month with 295% net revenue retention, betting that AI agents win by meeting users where they already communicate rather than forcing new apps.
Resolve AI, a platform that uses AI to monitor systems, spot outages or performance issues, and fix common problems automatically before engineers have to jump in, raised $125M in a Series A round led by Lightspeed Venture Partners at a $1B valuation. The company says its AI agents are already running in production at large tech, financial services, and consumer companies like Coinbase and Zscaler, handling incident diagnosis and remediation while reducing the amount of human firefighting required. It plans to use the funding to deepen its product, expand integrations, and support more large-scale enterprise deployments.
Waymo, a self-driving vehicle company owned by Alphabet that's operating fully autonomous ride-hailing services using its own robotaxi fleet, is seeking to raise $16B in an upcoming round at a $110B valuation. Alphabet is contributing roughly $13B, with the remainder coming from external investors including Sequoia Capital, DST Global, and Dragoneer Investment Group. The news follows reports that U.S. safety regulators are investigating the company after a vehicle struck a child in Santa Monica.
Kindred, a members-only home-swapping startup that lets travelers stay in each other's homes instead of paying for Airbnbs, raised $125M in a $40M Series B round co-led by NEA and Dylan Field, and an $85M Series C round led by Index Ventures. The platform was founded in 2021 as a way to make travel more accessible and has since grown to almost 300,000 members across 150+ cities, doubling its membership in 2025 alone, and has hosted almost 350,000 nights. It functions by members earning credits when they open their homes to others, which they can use to stay in other homes around the world, with no cash exchanged between hosts and guests. The catch? Kindred's significant service and cleaning fees!
Anthropic is working on a tender offer that would let current and former employees sell shares at a valuation of at least $350B, according to Bloomberg sources. The potential deal is coinciding with a new funding round that is targeting over $20B in new capital. The transaction is seeking to provide liquidity to staff as the company competes for top talent in the AI sector.
Cerebras Systems, a startup chipmaker that designs specialized processors built as a single, wafer-scale chip to train and run large AI models without stitching together thousands of GPUs, raised $1B in a Series H round led by Tiger Global at a $23B valuation, almost tripling its valuation from $8.1B in September. The company is positioning itself as a credible alternative to Nvidia as AI labs and cloud operators look to diversify chip supply for training and inference workloads. The funding comes after Cerebras struck a commercial deal with OpenAI and chose to remain private after pulling a planned IPO.
GrubMarket, a digital marketplace that connects food producers, wholesalers, and distributors with businesses buying fresh and packaged food, raised $50M in a Series H round led by Future Food Fund and Portfolia Funds at a $4.5B valuation. The company plans to use the funding to expand its e-commerce tools and AI-driven software for inventory, logistics, and operations across the U.S. food supply chain, targeting distributors and suppliers still reliant on manual workflows.
Sapiom, a startup building a financial infrastructure layer that lets AI agents securely pay for software, APIs, data, and compute without human intervention, raised $15M in a seed round led by Accel. The company was started by Ilan Zerbib, who spent five years as Shopify’s director of engineering for payments, and aims to build a solution that eliminates back-end infrastructure headaches for nontechnical users. The startup is still in early stages but hopes that its solution will be adopted by vibe-coding and AI agent companies.
Once Upon a Farm, an organic baby and kids food brand started by actress Jennifer Garner, held its IPO on the NYSE under the ticker OFRM, raising $197.9M and valuing the company at about $724M. The brand, which sells refrigerated pouches and kids snacks through retailers like Target, Whole Foods, Walmart, and Costco, reached $201.6M in sales during the first half of 2025 as demand for less processed kids food grew. OFRM rose 16.9% in its market debut on Friday.
Fifth Third Bancorp completed its merger with Comerica to form the ninth-largest U.S. bank with roughly $294 billion in assets. The combined bank expands Fifth Third’s footprint in high-growth markets like Texas, California, and the Southeast while strengthening its middle-market commercial banking, payments, and wealth management businesses. Full system and brand integration is expected in the third quarter, with Comerica locations operating under their existing brand until then.
CommerceX, a Japanese holding company focused on acquiring and operating B2B payments, fintech, and commerce infrastructure businesses, raised ¥17.3 billion ($109M) in a Series A round led by Dual Bridge Capital. The company will use the funds to strengthen RECORE, its cloud-based POS register system that currently serves 400 retail businesses, as it prepares for a future public listing.
Kitopi, UAE-based cloud kitchen platform that operates and manages over 200 delivery-only restaurant kitchens for brands across the Middle East, raised $50M in a Series D round led by EvolutionX, bringing its total amount raised to $765M. The funding comes after Kitopi reached profitability and will be used to scale its owned brands and franchising operations across markets including the UAE, Saudi Arabia, Qatar, Bahrain, and Kuwait.
Texas Instruments, a Dallas-based semiconductor manufacturer that apparently makes more than calculators, agreed to acquire Silicon Laboratories, an Austin-based semiconductor manufacturer focused on low-power wireless chips and software used in IoT and smart home devices, for $7.5B in an all-cash deal, marking its largest acquisition in over a decade. The deal adds roughly 1,200 wireless connectivity products to Texas Instruments’ portfolio and brings Silicon Labs’ manufacturing in-house, a move it expects to drive scale and lower costs across industrial, consumer, and smart device markets. The transaction is expected to close in the first half of 2027, pending regulatory and shareholder approval.
Loop AI, an “agentic co-worker” for restaurant chains that automates complex financial and operational tasks, raised $14M in a Series A round led by Nyca Partners. The company says its business has grown sixfold since 2024 and now supports thousands of restaurant locations, including large chains like McDonald’s, Little Caesars, and Whataburger. The funding will be used to expand its product suite and hire across offices in the U.S. and India as restaurants look to make third-party delivery more profitable.
Positron, a three-year-old semiconductor startup building chips designed to run LLMs faster and more efficiently than general purpose GPUs, raised $230M in a Series B round co-led by Arena Private Wealth, Jump Trading, and Unless, at a $1B valuation, bringing its total amount raised to $300M. The company plans to use the capital to speed up deployment of its high-speed memory tech and to move faster toward its next-generation Asimov chip, targeting production in early 2027. Positron is positioning itself as an inference-first alternative to Nvidia, claiming its Atlas chip can match H100-level performance at under one-third the power, with additional strength in high-frequency and video-processing workloads.
GOcxm, a customer experience management software focused on collecting, analyzing, and acting on customer feedback across e-commerce and in-store touchpoints, acquired Emotive Technologies, the company behind Apex, an AI-powered consumer insights and decision intelligence platform, for an undisclosed amount. The deal adds predictive modeling and AI-driven decisioning to GOcxm’s platform, letting CPG brands test strategies, forecast outcomes, and adjust execution before and during retail campaigns. Apex’s technology and team will be folded into GOcxm’s product roadmap as it pushes deeper into AI-powered retail execution and shopper intelligence.
ZILO, an Indian fashion quick commerce startup, raised $15.3M in a Series A funding round led by Peak XV Partners. The company plans to use the capital to expand its 60-minute delivery fashion model across major Indian cities, focusing on tighter inventory control and faster fulfillment to compete with both traditional e-commerce and local retailers. Former Flipkart and Myntra executives founded the platform, which currently stocks products from over 200 brands.
ShipTime Canada, a shipping and logistics platform that helps merchants compare rates, generate labels, and manage parcel shipping across multiple courier partners, acquired Warehowz, an on-demand warehousing marketplace that connects shippers with a network of third-party warehouse facilities for flexible storage and fulfillment, for an undisclosed amount. The transaction is integrating over 2,500 warehouse facilities into ShipTime's platform to provide merchants with flexible storage and faster fulfillment options, targeting enterprise shippers by combining courier services with a scalable inventory network across North America.
Zscaler, a cloud security platform that replaces traditional firewalls with zero trust access for users, applications, and devices, acquired SquareX, a browser security platform that isolates web activity and blocks malicious content to protect users from phishing, malware, and browser-based attacks, for an undisclosed amount. The deal extends Zscaler’s Zero Trust model into standard browsers like Chrome and Edge, letting companies secure unmanaged and personal devices without relying on VPNs or separate enterprise browsers.
Neo Financial, a Canadian fintech offering digital banking products like credit cards, savings accounts, and rewards, raised $68.5M in a Series F round led by a syndicate of more than 100 Canadian investors, at an undisclosed valuation said to be higher than the $363M valuation it received in its 2024 Series D round. The company plans to use the capital to package and sell existing loans to investors, a bank-style securitization strategy that lets Neo scale its lending business without tying growth directly to new equity funding. Neo also received approval from the Bank of Canada to register as a payment service provider, a prerequisite for participating in Canada’s upcoming real-time payments and open banking frameworks.
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