Hi Shopifreaks
Before we begin, I'd like to welcome Cloudways to the Shopifreaks family as our newest official News Partner! 🎉🥳
Cloudways is a managed web host built with intelligence that offers simple, scalable hosting with AI-powered server diagnostics and automated troubleshooting for agencies, developers, and businesses. Their new NGINX stack delivers up to 65% faster performance, and Cloudways Copilot helps handle day-to-day hosting maintenance so you can spend more time growing your business instead of managing servers (which is my least favorite part of running an online business).
Here’s what Cloudways brings to the table:
- High-performance hosting – Experience faster load times with their optimized NGINX stack, built to keep e-commerce and SaaS sites running smoothly during traffic spikes and campaigns.
- Unlimited websites, no visitor caps – Host as many sites as you want on a single plan with no hard limits on visitors, making it an especially great solution for agencies and business owners that host multiple sites.
- Choice of five cloud providers – Deploy websites and apps on DigitalOcean, Vultr, Linode, AWS, or Google Cloud, and scale vertically or horizontally as your traffic grows. Cloudways merged with DigitalOcean in 2022, so now they operate under the same umbrella, but you can choose to use Cloudways as your operating system alongside your preferred cloud provider.
- Stack-agnostic platform – Cloudways supports a wide range of workloads, including WooCommerce, Magento, Laravel apps, headless builds, and custom projects. And because there are no visitor limits and plans scale easily, you can grow traffic and launch new sites without having to renegotiate your hosting.
- Cloudways Copilot – Offload time-consuming hosting tasks to an AI-assisted experience that helps monitor, optimize, and maintain your servers so you don't have to spend all day in a control panel.
- Simple, pay-as-you-go pricing – Only pay for the resources you use, with the flexibility to scale your server up or down without long-term contracts or overcommitting to fixed capacity.
- Free Migration – Cloudways offers free migration for your first website, handled by their experts. WordPress users can also migrate unlimited sites at no cost using their WordPress Migrator Plugin.
- 24/7 human support – Get access to real people around the clock to help with performance tuning, troubleshooting, migrations, and other technical support. This, for me, is one of the biggest perks of Cloudways. Their live chat support is fantastic! Offering live chat support is a requirement for me when choosing a host.
✨ Want to know why I'm especially thrilled to have Cloudways as one of our sponsors?
They're my host! I've personally used Cloudways for over three years now after switching from — well, I won't say who. 🙄
I was unhappy with my prior host solutions, one of which was slow and experienced way too much downtime, and the other which functioned great, but was way too expensive (charging me per visit).
I host and manage 30+ websites for myself and clients, so choosing a hosting provider is an extremely important decision that I put a lot of research into. Once I decided that Cloudways was the right solution, I started by migrating just one of my websites over and testing the waters for a few months. Then after falling in love with both the hosting performance and their customer support (which is 24/7 live chat), I slowly began bringing over the rest of my websites.
After the migrations, not only did my websites perform better, faster, and with minimal issues or downtime, I was also now able to host ALL of them for less than I was spending per month on hosting just ONE website with my previous managed host (the one that charged per visit).
Ever since making the switch to Cloudways in 2022, it's been my #1 recommended host, and I've sent them a lot of business. So when Danish from Cloudways reached out to me asking if I'd be open to working with them, I said — “I'd be thrilled to! I'm already a user and an ambassador of Cloudways, so it'd be an easy and authentic recommendation for me to make.”
If you're unhappy with your existing host or looking to start fresh on a new project, I highly recommend you go with Cloudways.
Visit cloudways.com to explore plans, spin up a server in minutes, and see how their managed cloud hosting can support your next phase of growth.
And now onto your regularly scheduled programming…
In this week's edition I cover:
- Google needs to double AI capacity, and fast!
- Target teams up with OpenAI for chat-shopping
- Some Shopify stores are now live on ChatGPT
- Meta defeat the FTC
- Amazon Autos partners with Ford
- Perplexity makes its agentic shopping tool free for everyone
- Australia bans kids under 16 from social media
- Shopify brought back human support agents
- Jeff Bezos is CEO of a new startup
- TikTok is letting you control how much AI slop you consume
- Cash App launched a financial score
- Kroger is leaning towards fulfillment partners
- Adobe announced plans to acquire Semrush
All this and more in this week's 253rd Edition of Shopifreaks. Thanks for subscribing and sharing!
Stat of the Week
Google Cloud VP Amin Vahdat told employees that the company has to double its serving capacity every six months in order to meet demand for AI services. Vahdat said that Google's job “is of course to build this infrastructure but it's not to outspend the competition, necessarily.” (That's OpenAI's job, LOL.) He said that the company is “going to spend a lot,” but that the real goal is to provide infrastructure that is “far more reliable, more performant and more scalable than what's available anywhere else.”
1. Target teams up with OpenAI for chat-based shopping
ChatGPT is adding a new app this week that lets you search, discover, and buy products from Target directly within the chatbot. The news follows OpenAI’s launch last month of dedicated retail apps to ChatGPT, beginning with Canva, Coursera, Figma, Expedia, Spotify, and Zillow.
Here's how it'll work:
- A user can tag the Target app in ChatGPT and say something like, “Help me plan my 2 year old's bee themed birthday party.”
- ChatGPT will share curated ideas for products like bee-themed cups, plates, and decorations.
- The user can browse through the options, build a basket, and check out through their Target account.
- During checkout, they can choose whether to get the items shipped to their homes or pick it up at the store or at the curb.
- OpenAI says that the ability to link your Target Circle account and get same-day delivery is also in the works, but won't be available immediately after launch.
Here's what we don't know yet:
- Is Target participating in ChatGPT's Instant Checkout feature alongside Etsy, Walmart, and Shopify? Or will shopping at Target be limited to its app within ChatGPT?
- Will Target products automatically appear in ChatGPT shopping answers without specifically calling the Target app?
- Is multi-cart checkout coming to ChatGPT across the board? Or just with this Target app for now? The ability to add multiple items to your cart when shopping via ChatGPT's Instant Checkout feature is still labeled as “coming soon,” but is advertised as a feature with the new Target app.
The ambiguity of the announcements leads me to understand that OpenAI has two distinct shopping-related programs happening: 1) Instant Checkout, and 2) ChatGPT Apps, and that they don't necessarily always overlap. This could be wrong, but I wasn't able to find any information stating otherwise. However we'll find out this week when the Target app rolls out if / how the two worlds overlap.
And if the answer is “No, Target products won't appear in shopping answers outside the Target app,” I'll inevitably have to ask — why not? ChatGPT Apps have barely launched, and I don't imagine that they've been widely adopted by users yet. Why wouldn't Target instead participate in ChatGPT's Instant Checkout feature like Walmart instead of asking users to call on a dedicated app?
Prior to this e-commerce partnership, Target and OpenAI have had an existing working relationship built around Target's use of ChatGPT Enterprise to power some of its employee operations. For example:
- Target’s Agent Assist and Store Companion help teams in service centers and stores with help price matching (although only against Target online now), initiating a return, and other tasks. Does it remind the employees to smile at customers? 😂
- Target’s Shopping Assistant and Gift Finder use AI-powered conversational and recommendation tools to simplify browsing and help guests find personalized gift suggestions based on the recipient’s interests, age, or occasion.
- Guest Assist and JOY solutions help Target guests and vendor partners resolve issues.
In other OpenAI app news this week… the company joined forces with Intuit in a multi-year partnership to use OpenAI models across TurboTax, Credit Karma, QuickBooks, and MailChimp. The models will help power select Intuit AI agents for tasks like cash-flow forecasting, tax preparation, and payroll management. Great idea everyone to give OpenAI all your user data and proprietary information! So far they've been excellent stewards of IP.
2. Select Shopify stores are now live on ChatGPT
Speaking of Instant Checkout… Remember a few weeks ago when OpenAI announced the launch of Instant Checkout and said it was initially partnering with Etsy and Shopify? Then a few weeks later, when Walmart publicly embraced Instant Checkout?
After the announcement, the integration immediately went live with Etsy, but what happened to Shopify? All this anticipation and no climax was starting to give us blue carts!
Well, almost two months later, Instant Checkout has now officially rolled out on select Shopify stores including Glossier, SPANX, and SKIMS, with “more rolling out very very soon” according to Shopify President Harley Finkelstein, who shared a video on X showcasing the feature in action.
The main Shopify account on X also shared a video showcasing:
- A user asking ChatGPT, “I want a new scent for fall that's warm and floral but not too Elon Musky. Any recs?”
- ChatGPT replies, “Absolutely. Here are a few popular perfume options with warm and floral scents that you might enjoy,” followed by a grid of product results.
- After clicking on one of the results from Glossier, it takes the user to a product details page where it displays an image carousel, variants, price, a “Buy” button, and AI-generated summaries of “What people are saying” based on the item's reviews.
- The user can then check out on that page, without having to visit the merchant's website.
The Instant Checkout feature is powered by the Agentic Commerce Protocol, which OpenAI developed in partnership with Stripe to let AI agents handle shopping and checkout directly inside conversations through standardized merchant integrations. Initially it supports single-item purchases, but in the future it will expand to multi-item carts. OpenAI will take a fee from transactions that are completed through ChatGPT, but no-one knows how much yet, and the fee could be different for each partner.
At this point, it doesn't seem like the Instant Checkout feature will become widely available for all Shopify merchants this holiday season, but it's a step in the right direction that at least some stores are now live.
3. Meta defeated the FTC's antitrust case and is officially “not a monopoly”
On Tuesday, a federal judge ruled that Meta had not illegally stifled competition when it acquired Instagram and WhatsApp, and that the company does not hold a monopoly in the “personal social networking” market. Therefore it will not have to divest its acquisitions of the two apps.
The suit was brought by the FTC against Meta in December 2020, arguing that social networking constitutes its own market, and that Meta’s purchase of Instagram and WhatsApp exemplifies anticompetitive behavior in violation of Section 2 of the Sherman Act.
The FTC defined Meta's product market as “personal social networking” for communication with friends and family, and not for entertainment purposes like TikTok and YouTube. However Meta defended itself by claiming that it operates within “the broader field of social media” and that TikTok and YouTube function as “substitutes for Facebook and Instagram.”
Judge James Boasberg wrote in his opinion:
- “Facebook, Instagram, TikTok, and YouTube have thus evolved to have nearly identical main features.”
- Meta’s most popular features are “indistinguishable from the offerings on TikTok and YouTube.”
- “When someone first signed up for Facebook, his friends on the app were his friends in real life. More than a decade later, his offline friends have changed, but his old Facebook friends are still there. Longtime users’ friend lists have thus become an often-outdated archive of people they once knew,” and “posts from friends have therefore grown less interesting.” That sounds personal!
- “Americans now spend only 17 per cent of their time on Facebook viewing content from their friends.” (And just seven per cent on Instagram). “What has replaced content from friends? For the most part, short videos posted by strangers and recommended by AI.”
As much as I hate to admit it, I've got to side with Meta on this one — at least in 2025. If this case had been brought to trial in 2015, my opinion and the case outcome may have been different, but it's an entirely different landscape now. Some might argue that it's an entirely different landscape now because of those anti-competitive acquisitions by Meta in 2012 (Instagram) and 2014 (WhatsApp), and if they had never happened, we'd have even more competition in the market today, but there's really no way of knowing.
The only truth today is that Meta very much competes in the same space as the other apps mentioned, and the line between “personal social network” and “entertainment app” continues to blur across all platforms.
4. Amazon Autos partners with Ford to sell pre-owned vehicles
Amazon Autos partnered with Ford to sell its certified pre-owned vehicles on the platform, enabling customers to purchase, finance, and schedule a pick-up of the cars from participating dealers in Los Angeles, Seattle and Dallas, with more markets coming soon. Ford says that selling on Amazon Autos is a voluntary program, but that 160 of its roughly 2,900 dealers across the country have expressed interest and started the process.
Amazon Autos launched in December 2024 with Hyundai vehicles, later added used vehicles from Hertz's fleet to the platform, and now is partnering with Ford, with more automakers expected to join the platform soon.
This is one of the most avoidable industry disasters in modern history to take shape in real-time in front of our eyes.
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?
Here's a timeline of what's about to transpire:
- Amazon entices automobile dealers to sell on its platform with the promise of new customers.
- Amazon leverages its relationships with initial partners to onboard other dealers and manufacturers.
- Suddenly it's hard to get noticed on Amazon Autos, so advertising is introduced and Amazon begins to take the dealers' margins.
- Amazon becomes a market leader in the automobile search space because they have more customers & inventory and better SEO than any individual dealer.
- Amazon pits the dealers, who are now reliant on Amazon Autos, against each other and forces them to undercut each other on price so that Amazon Autos has the lowest prices of any platform.
- Amazon eventually finds a way to bypass the dealers altogether, creating a direct-from-manufacturer model, like the kind that Tesla pioneered. Many US states prohibit automobile manufacturers from selling vehicles directly to consumers and require sales to occur through independently owned dealerships, but Amazon will lobby against those laws, alongside EV companies, and eventually have them changed.
- And/or Amazon will turn its Delivery Service Partners into “auto dealers” to skirt the laws, creating dealership relationships directly with the manufacturers in order to offer Free Prime Delivery of new vehicles.
- Dealerships will eventually find themselves asking, “Why the hell did I participate in Amazon Autos?” as they bleed to death.
“Your margin is my opportunity” — isn't that what Jeff Bezos always said? The world is watching in real-time as Amazon makes dealership margin their opportunity, following their same playbook of leveraging 3rd party sellers' inventory and infrastructure to build their market share before squeezing them of their margin through advertising fees and/or entering the market directly themselves.
If automakers are this desperate to position their car inventory alongside their competitors in a race to the bottom, then why not collaboratively create their own automobile marketplace behemoth? Why not collectively invest in and develop a marketplace solution, similar to how the banking industry created Zelle? Why voluntarily and unnecessarily give control to Amazon?
Is history lost on Ford, Hyundai, and any other automakers that partner with Amazon? Honestly, WTF? Am I the crazy one?
Hit reply and let me know your thoughts or join the conversation on LinkedIn (which has attracted quite the debate in the comments).
5. Perplexity to make its agentic shopping available to everyone for free
Perplexity announced that its “Buy with Pro” agentic shopping experience, which originally launched last November exclusively for paid subscribers, will now be free for all US users across its desktop app and website, with iOS and the Comet browser following in the weeks ahead.
When Buy with Pro rolled out in 2024, it was positioned as a subscription-only feature that let Pro and Max users buy products with one click, get more personalized recommendations, and benefit from merchant integrations that improved visibility in search results. Now the company is removing the paywall entirely and bringing its shopping capabilities to all users — likely in response to ChatGPT's launch of Instant Checkout, which is free for everyone.
That refresh includes better shopping-intent detection, product cards with images and on-demand descriptions, and a checkout flow powered by PayPal, which will serve as the merchant of record and extend its buyer-protection policies to purchases made through Perplexity.
Dmitry Shevelenko, Perplexity’s Chief Business Officer, told CNBC:
“The agentic part is the seamless purchase right from the answer. Most people want to still do their own research. They want that streamlined and simplified, and so that’s the part that is agentic in this launch.”
Perplexity plans to roll out the free features the week of Thanksgiving, coinciding with PayPal’s own holiday promotion that will offer one-time cashback through its Instant Buy merchants between Black Friday and Cyber Monday.
Earlier this month I reported that Amazon was suing Perplexity over its Comet browser disguising itself as a Chrome browser so that it could shop autonomously on Amazon.com, which Amazon explicitly prohibits. If you missed that story, you should give it a read because it's an important one. The outcome of the lawsuit will have a major impact on the agentic commerce market in regards to what permissions are necessary for AI to shop on your behalf.
6. Australia is banning social media for kids under 16 years old
The government of Australia is banning children under 16 years old from having social media accounts, in a world-first policy that's set to take place from Dec 10th onwards. Ten social media companies including Facebook, Instagram, TikTok, Snapchat, Threads, X, Reddit, YouTube, Kick, and Twitch will be responsible for taking “reasonable steps” to ensure that kids under 16 in the country cannot set up accounts on their platforms and that existing accounts are deactivated.
The government said it will continue adding to the list of affected platforms, considering three main criteria when doing so:
- Is the platform's sole or “significant purpose” to enable online social interaction between two or more users?
- Does it allow users to interact with some or all other users?
- Does it allow users to post content?
YouTube Kids, Google Classroom and WhatsApp are not included on the list, as they were not deemed to have met those criteria, and children will still be able to view most content on YouTube and other platforms that do not require an account to watch.
Children and parents will not be punished for infringing on the ban. Only the social media companies are charged with enforcing it, facing fines up to $49.5M for serious or repeated breaches.
So what “reasonable steps” must these social media companies take to ban kids from their platforms?
The government has proposed several possibilities including requiring government IDs, face, or voice recognition, as well as using online behavior or interactions to estimate a person's age. (Sucks for any adults that love comic books and anime, I guess.) The government is encouraging platforms to use various methods of age verification, without specifying or requiring a particular one. However it's said that platforms cannot simply rely on users declaring their own age.
How are social media companies responding?
- Meta said it will begin closing teen accounts on Dec 4th, with users who are mistakenly kicked off able to use their government ID or provide a selfie to verify their age.
- Sapchat said users can use bank accounts or photo IDs to verify their age or take a selfie.
Australia enacted this ban after a study earlier this year determined that 96% of children aged 10-15 used social media and that 7 out of 10 had ben exposed to harmful content and behavior including misogynistic material, fight videos, eating disorders, suicide, cyberbullying, and grooming from adults.
I mean, I get it… but it's not going to work.
Kids are too smart. They're going to figure out a way around it and/or simply gravitate towards other platforms that are not yet on the list. The Australian government will be playing an ongoing game of whack-a-mole to add apps and platforms to their list.
Also, the current list of impacted apps seems incredibly arbitrary. WhatsApp, Telegram, and Signal aren't on the list even though they offer group chat features and some offer public status updates?
The whole thing seems like a stepping stone to require all users in the country, adults included, to provide government issued IDs to participate in online services.
The world is watching closely. Malaysia already announced on Sunday that it plans to follow in Australia's footsteps and ban children under 16 from social media starting next year, and I can only imagine that other countries will soon follow.
7. Shopify is making it easier to talk to a human
It turns out that Shopify's recent attempt to push merchants to their AI chatbots for customer support didn't go to well. Who could've guessed!? In fact, it went so poorly that the company is now making it easier once again to speak to a human. Shopify wrote:
“We heard you. After trying self‑serve, it wasn’t always clear how to reach a person. What’s new: we’ve added a ‘Chat with a human' button on Help Center pages that puts you directly into the lineup for an advisor. On a typical day, we reach most contacts within 5 minutes.”
How did they hear you? Did the AI support agents report back? LOL
All SaaS companies, e-commerce platforms, and marketplaces should take note of this news. It didn't work for Shopify, and it won't work well for you! Any platform that acts as a middleman between sellers and their buyers needs to provide their sellers with easy and immediate access to human support. Our livelihoods often depend on it! Frankly it should be required by law in the U.S., but there's no-one left in the government right now that would ever make that happen.
eBay apparently didn't get the memo… The company is currently taking the opposite approach and planning to ramp up its use of AI for customer support as part of a multi-year effort to cut operating costs, according to recent job posts on its career's page in search of a senior director of CX Engineering to “leverage AI to redefine our customer journey,” as spotted by Liz Morton of Value Added Resource.
In recent years, eBay has already deployed AI to read support emails, generate initial responses, and route tickets, which many sellers say is killing the quality of customer service. Don't worry guys, it'll only get worse from here!
8. Jeff Bezos is launching a new startup and guess who's the CEO?
Jeff Bezos is launching a new AI startup called Project Prometheus, which will focus on developing AI for the engineering and manufacturing of computers, automobiles and spacecraft. It's unclear exactly when Project Prometheus launched, but it's already reportedly raised $6.2B, part of which came from Bezos himself, and hired 100 employees, poaching several from OpenAI, DeepMind, and Meta.
Bezos appointed himself co-CEO of an AI startup called, alongside his co-founder, Vik Bajaj, a physicist and chemist best known for his work at Google's moonshot factory, X, where he founded Verily, a life sciences and health technology company focused on developing research tools, care programs, and precision health products.
This is the first time that Bezos has taken a formal operational role in a company since stepping down as CEO of Amazon in July 2021, as despite his involvement in Blue Origin, his official title at the space company is founder.
Prometheus sounds interesting, but two CEOs of one company? You can't give me gravy and tell me it's jelly, 'cause gravy ain't sweet!
Project Prometheus is one of several new startups focused on applying artificial intelligence to physical tasks like robotics, drug development, physics, and other scientific discovery. Earlier this year, several researchers left Meta, OpenAI, and Google DeepMind to launch Periodic Labs, a startup focused on building AI tech focused on accelerating physics and chemistry discoveries. Last year, Bezos also invested in Physical Intelligence, a startup that is applying AI to robots.
Honestly, these are the kinds of AI startups that get me excited! You can only read about so many AI chatbots before becoming a little tired of the space…
9. Other e-commerce news of interest
Whatnot, a Los Angeles-based live shopping marketplace that recently raised $225M in a Series F round, introduced four AI tools that speed up product listings and shipping tasks for its sellers. Snap List and Live List let sellers generate listings with a phone camera, while Automated Shipping Profiles and Proof of Drop Off automate label selection and drop-off scans. The company reported more than $6B in GMV this year, operates in nine countries, and says the number of merchants earning more than $1M in lifetime sales has more than doubled in 2025.
Amazon introduced sponsored product and brand prompts, which allow brands to inject their sponsored campaigns into AI conversations with paid prompts like, “Why choose Accent Athletics shirts?” The feature entered open beta in the U.S. this month and is automatically enabled for advertisers using Sponsored Products and Sponsored Brands campaigns. During the beta phase, the prompts are offered at no additional cost to advertisers so that Amazon's systems can learn how to optimize them, but it's expected that eventually sponsored prompts will be a separate channel with additional fees.
TikTok will soon be testing a slider tool under its Manage Topics settings that will allow users to determine how much AI-generated content appears in their feed — including the option to view “More AI Content” if that's what you really want. TikTok has also been working to improve its AI-generated content labels, testing advanced labeling techniques such as a solution called “invisible watermarking” that helps label AI content more reliably, including videos that have been previously stripped of their metadata. I love how the same companies that are helping to produce AI slop will inevitably be the ones charged with safeguarding users against it.
In other TikTok news… The company introduced a Time and Well-being space that replaces its screen time settings and adds features like an affirmational journal, sound generator, and breathing exercises, as well as Missions that reward users for habits like limiting screen time and staying off the app during sleep hours. Last but not least, TikTok shared more information about its expanded efforts to detect and remove extremist content, reporting that it removed more than 6.5M videos in the first half of 2025 and dismantled 17 networks made up of more than 920 accounts to used tactics like coded language and off-platform coordination to avoid detection.
BigCommerce and Organic Payment Gateways, a Maine-based payment processor, launched a new integration that allows cannabis seed retailers and hemp seed wholesalers to accept credit cards on the platform, aiming to serve a niche market that has historically faced obstacles accepting payments on Stripe, PayPal, Square, and other large payment processors. The integration with BigCommerce now allows these retailers to connect credit card processing directly to their stores without the use of redirects or third-party checkout pages. Shopify actively promotes that it works with CBD and other types of cannabis brands, but then simultaneously doesn't allow them to process payments through Shopify Payments, which is powered by Stripe, requiring that they work with one of their approved 3rd party processors and pay additional transaction fees by doing so. This new partnership from BigCommerce and Organic Payment Gateways offers the cleanest integration that I know of with a major e-commerce platform.
Amazon quietly updated its robots.txt file to block more OpenAI web crawlers, including agents used for model training, web browsing and search, in a change spotted by Juozas Kaziukėnas and reported on by ModernRetail. He wrote, “ChatGPT runs three different crawlers: GPTBot (for model training), ChatGPT-User (for crawling the web when a user asks a question), and OAI-SearchBot (for web search). Amazon had GPTBot blocked for months. This week it blocked the other two.” Kaziukėnas notes that the change happened during the same week that Amazon simultaneously agreed to a $38B cloud computing deal with OpenAI, and that Amazon also blocks Anthropic's crawlers, even though they are the company's largest investor.
Cash App is piloting a feature called Cash App Score that allows users to see in real-time how their interactions with the app influences their financial health, such as maintaining funds in their account, depositing a paycheck, or repaying a loan on time. Block says it's been using its real-time underwriting model to power its credit products for several years, and the new Cash App Score gives customers more transparency into how their credit eligibility is determined, allows them to better understand what factors are influencing them, and take specific actions to build their financial health within the ecosystem.
One in five U.S. employers said in August that they planned to slow hiring in the second half of 2025, according to the WSJ, and job postings on Indeed are already down 12 percentage points from pre-Covid levels. Daniel Zhao, chief economist at Glassdoor, told ModernRetail, “It has been very difficult for businesses to plan for hiring and investment when they just haven’t been sure how the economy is going to evolve over the coming months or how policy might change. It’s just very, very difficult to commit to hiring more people when you don’t know if the economy is going to slow down further.” Zhao also noted that hiring rates are comparable to those in the early 2010s and are low given the current unemployment rate, which has soared to a four-year high as of August.
Meta's Chief Revenue Officer, John Hegeman, is leaving the company after 17 years to build his own startup, which is currently undisclosed, according to a Facebook post announcing his departure. Hegeman served as an engineering leader for the company's advertising systems for seven years, worked on the Facebook app for five years, and then returned to ads and monetization in 2021. He also serves on Robinhood's board of directors and is married to Meta's CFO, Susan Li. Andrew Bocking will take over as product-group lead for ads and business messaging, and Naomi Gleit will become leader of business AI and other new monetization opportunities following his departure.
Block launched a campaign called “Bitcoin is Everyday Money,” advocating for a de minimis tax exemption on Bitcoin transactions under $600 that would exclude them from capital gains taxation and reporting requirements. Currently under U.S. law, Bitcoin is classified as property, meaning selling any amount triggers a taxable event, which Block argues discourages the everyday use of Bitcoin as a payment method. Block's campaign features billboards and digital displays throughout Washington, D.C. and a website that enables visitors to contact their representatives and urge them to support a $600 de minimis tax exemption for goods and services. Future headline if that passes: “Bitcoin Whale Sells $6.5 billion of BTC via 10.9 million transactions under $600 each.” LOL. Just joking, as Block is pushing specifically for the purchase of goods and services under $600 to be omitted, not the sale of BTC for cash.
A Fortune investigation found that anti-Semitic and Holocaust-denial content is widely circulating on Instagram Reels, generating millions of views and appearing directly adjacent to ads from major brands including JPMorgan Chase, Nationwide Insurance, SUNY, Porsche, and even the U.S. Army! Meta removed some posts after being notified but similar content continued to surface, in part due to January policy changes that ended third-party fact-checking in the U.S. and loosened political-content rules. One prominent hate-speech creator told Fortune that racist and Hitler-themed reels “don’t get banned anymore,” and another said that posts referencing Hitler or the Holocaust “always get more traction.” Meta said that it's already actioned 21M pieces of content in 2025 for violating their prohibition on “Dangerous Organizations and Individuals,” and that its commitment to tackling anti-Semitism is “unchanged.” (Is that a good thing or a bad thing?)
Members of Facebook Groups will soon be able to participate under a custom nickname and avatar, as opposed to having to use their real name or post anonymously. Nicknames must be enabled by group administrators, and sometimes individually approved, but once they are active, users can post using either their real name or their nickname. Woohoo! I can't wait to shop for cars or land from “DillDoh420” in my local buy / sell group! Honestly, requiring people to use their real names was one of the big things Facebook has had going for it since it launched in 2004. Prior to then, the Internet was very much a screenname-based ecosystem, but The Facebook normalized connecting your real life and online identities, which later added a layer of trust to Facebook Groups once they came about. That said, I do see the value in being able to interact anonymously but still with a consistent identity in certain communities, which screennames provide. It's great that Facebook left it up to each group admin's discretion on whether to allow nicknames or not.
U.S. Bank introduced the Split Card, a Mastercard that automatically converts purchases into three-month installment plans for transactions over $100, while smaller purchases are aggregated and financed the same way at the end of the month. Customers can then optionally extend payment plans to six or twelve months for a flat 1.5% monthly fee. Similar to traditional credit cards, consumers have a total spending limit based on their credit history, as opposed to underwriting each individual transaction like BNPL firms. U.S. Bank modeled the Split card off its BNPL product Extend Pay, which it's offered for the last couple years and enabled cardholders to take any purchase over $100 and split it into fixed monthly payments.
OpenAI CEO Sam Altman told employees that Google's recent progress in AI could “create some temporary economic headwinds for our company,” and that “we know we have some work to do but we are catching up fast.” Altman acknowledged that Google “has been doing excellent work recently” with pretraining, which is the first phase of developing a LLM in which it is exposed to data from the web and other sources so it can learn connections between them — something that OpenAI has struggled with. Altman said in the memo that “ChatGPT is AI to most people, and I expect that to continue,” and that the company needs to “stay focused through short-term competitive pressure” so it can “stay focused on really getting to superintelligence.”
The Trade Desk has been urging advertisers to switch from its older Solimar interface to its newer Kokai platform, with some buyers telling ADWEEK they are being “forced” to use Kokai because they are locked out of creating campaigns in Solimar. The changes are part of The Trade Desk's ongoing plans to migrate all of its advertisers to the Kokai platform, which it says is currently in use by 85% of its clients. Buyers report glitches, missing features, and workflow issues in Kokai, among other concerns about stability as the full transition approaches.
Kroger is shutting down three of its automated fulfillment centers to instead focus on in-store fulfillment and third-party e-commerce partnerships, such as with Instacart, DoorDash, and Uber. The company is looking to improve its e-commerce profitability by around $400M in 2026 through these changes, which follow a “full site-by-site analysis” of its automated order fulfillment network earlier this year. Kroger has reported YoY digital sales increases almost every quarter since 2022, but its e-commerce business remains unprofitable, which is something interim CEO Ron Sargent pledged earlier this year to change.
In other Kroger news… The company launched Agent Monday, a weekly AI-generated email report that delivers customized performance insights to CPG brands using data from 84.51°’s Stratum platform. The digest highlights short- and long-term sales trends, competitive benchmarks, geographic anomalies, and promotion performance, aiming to replace the manual Monday reporting work category managers typically do. Kroger says more than 600 reports were delivered at launch, and the tool will expand into on-platform AI summaries as the company moves toward faster insight-to-action workflows for suppliers.
Meta had a “17x” strike policy for accounts that reportedly engaged in sex trafficking, according to Instagram's former head of safety and well-being Vaishnavi Jayakumar — information that was revealed in a court filing that was unsealed on Friday. “We have reason to believe that you're involved in sex trafficking on our platform. Do that 16 more times and we're going to have a problem!” The newly public brief alleges that Meta was aware that millions of adults were contacting minors on its platforms, its products exacerbated mental health issues in teenagers, and content related to eating disorders, suicide, child sex abuse was often detected but rarely removed, and that the company failed to disclose these issues to the public or Congress when asked, nor did they implement safety fixes in a timely manner that could have protected young users. Meta said it disagrees with the allegations, which “rely on cherry-picked quotes and misinformed opinions in an attempt to present a deliberately misleading picture,” and says it has worked hard for over a decade to provide safety to its teen users on the platform.
Remember when Elon Musk filed a lawsuit against the law firm Wachtell, Lipton, Rosen & Katz that sought to recover most of the $90M fee the firm received for defeating Musk's bid to abandon his multi-billion dollar purchase of Twitter? Pepperidge Farm remembers! Well, flash forward almost three years and X told a state court in California that it was dismissing its lawsuit with prejudice, which means it cannot be refiled, although they did not provide any reasons for the dismissal of the case. Musk originally said in the lawsuit that Twitter executives “ran up the tab” by “designating tens of millions of dollars in handouts to the firms as ‘success' or ‘project' fees,” but the law firm denied any wrongdoing and said that Twitter's former board “determined and approved” the fee, which forced Musk to honor his merger agreement and ensured “billions in value for Twitter's stockholders.”
Speaking of lawsuits coming to an end… Mark Zuckerberg and other Meta directors agreed to a $190M settlement of claims that they failed to address repeated privacy violations on Facebook and arranged a deal that shielded Zuckerberg from personal liability for those violations. The settlement ended a July trial over investors' claims that Meta board members mishandled the Cambridge Analytica scandal and improperly agreed to a $5B settlement with the FTC to personally protect Zuckerberg from having to use his own funds to cover some of the financial hit to the company. The settlement dramatically cut short the trial before a string of high-profile witnesses took the stand, including Zuckerberg, Marc Andreessen, Sheryl Sandberg, and Peter Thiel. So $190M hush money to end the PR disaster?
In other Meta lawsuit news… Meta has been ordered to pay €479M after a Spanish court ruled that the company had violated the European Union's GDPR and breached Spain's antitrust law. Madrid's Commercial Court said that Meta used personal data for behavioral advertising on Facebook and Instagram, which gave the company a “significant competitive advantage” in the market by using that data, which Meta argued was a “necessity for the performance of a contract,” rather than user consent. Regulators said that Meta's defense was inadequate and the court determined that all the profits Meta earned from advertising during that 5-year period were obtained in breach of the data protection regulation. Meta plans to appeal the ruling.
Nearly 40% of Amazon's 14,000 layoffs last month were engineering roles, according to recent state filings in New York, California, New Jersey, and Washington. The layoffs were in part due to AI, according to the company's HR chief Beth Galetti, who wrote in her memo that AI was “enabling companies to innovate much faster than ever before.” However Amazon later said in a statement that AI is not the main driver behind most of its job cuts, and that its bigger goal is to reduce bureaucracy in order to speed up development. Quiet Galetti!
Cloudflare experienced a major outage last Tuesday that intermittently shut down services including Shopify, Dropbox, X, ChatGPT, Canva, and Grindr (as confirmed by your husband). The company said that the outage was caused by an automatically generated configuration file that was designed to manage potential security threats. “Automatically generated” — so AI-generated? The file grew too large and crashed the system that was handling traffic for several websites. Cloudflare said there was no evidence that the outage was a result of an attack or caused by malicious activity — but I don't know if that makes it better or worse!
Walmart is moving its longtime listing on the NYSE to the tech-heavy Nasdaq, marking the biggest exchange transfer on record. Walmart is the NYSE’s fourth-largest listing by market cap, and it now joins fellow tech companies on the Nasdaq including Apple, Microsoft, Nvidia, and Shopify, which made the switch earlier this year. The stock is set to begin trading on the Nasdaq Global Select Market on Dec. 9 under its current ticker symbol “WMT.”
Colorado’s appellate court ruled that the state can apply its interest-rate caps to any loan where either the borrower or lender is located in Colorado, ending the ability of out-of-state bank partners to bypass those limits. The decision directly affects BNPL firms that rely on partner banks, since fees and charges may push short-term installment plans toward state cap thresholds. Providers may now need state-specific pricing, stricter location tracking, and revised underwriting models as a uniform national approach becomes harder to maintain.
Amazon launched Alexa+ in Canada, marking the first region outside of the U.S. to get access to the recently upgraded voice assistant. Engadget hilariously gave the example that Canadians can communicate with Alexa+ in natural language such as “It's dark,” and Alexa+ will switch on the lights for them. Alexa+ is free for Canadian users during its Early Access phase with purchase of select new Echo devices, after which it will remain free for Prime subscribers or cost $28 CAD per month for everyone else.
Klarna's BNPL payment options are now available on Apple Pay in Denmark, Spain, and Sweden, with France to follow, expanding the feature from its previous launches in the US, UK, and Canada, where it was one of the first BNPL providers to be available through the digital wallet. In other Klarna news, the company is expanding its partnership with the gift card company Blackhawk Network, which runs GiftCards.com, enabling consumers to purchase digital gift cards from more than 350 brands. “Hey mom, here's your gift card. I'll be paying for it for the next 4 months!”
Amazon, Temu, AliExpress, eBay, Joom, and Wish (which still exists) were all caught selling illicit products in France by a French consumer watchdog. Wish, Temu, and eBay were caught selling weapons, Amazon failed to filter underage shoppers from adult content, and AliExpress and Joom were caught selling — well, I don't even want to say! You'll have to go read the article yourself for that one. The French commerce minister referred the companies to public prosecutors and plans to raise the issue with EU counterparts as part of a broader crackdown on foreign marketplaces, following earlier action against Shein.
Depop is increasing its Boosted Listing advertising fees in the UK from 8% to 12%, aligning it closer to its parent company Etsy's Offsite Ads program, which adds a fee ranging from 12% to 15% depending on annual sales volume. Liz Morton notes that U.S. sellers are concerned that the fee increase will soon expand to them, similar to the way Depop rolled out the switch from seller fees to buyer fees in the UK first before expanding it to the U.S. in 2024.
super.money, an Indian UPI payments app backed by Flipkart, is developing a BNPL expansion that will partner with regulated banks and lenders, putting it in closer competition with Axio and Snapmint. The launch will include offering super.money as a checkout option on e-commerce sites and adding an in-app shopping layer that lets users finance purchases directly at checkout. The company's goal is to turn super.money into a single destination where shoppers can discover products, get credit, and complete payments in one streamlined flow.
26 Indian e-commerce platforms including Flipkart, Blinkit, Reliance Retail, Swiggy, Zomato, and Tata have voluntarily declared compliance with India's guidelines to eliminate dark patterns. The companies confirmed through self-audits (always reliable) and third-party reviews that their platforms are now free from manipulative design practices and aligned with the country's goal toward building a transparency and ethical digital economy. Just curious, but will anyone be checking?
🏆 This week's most ridiculous story… MediaWorld, a European electronics retail chain, accidentally sold Apple iPads to loyalty card holders for €15, and now they're e-mailing customers and asking for more money! A page taken straight out of the Michael Scott Paper Company playbook! MediaWorld is giving customers two options — either pay the difference in price with a €150 discount or return the iPad and receive a full refund of their €15 and a €20 voucher for their inconvenience. The company is offering this resolution as an olive branch before deciding to take legal action, which is questionable whether they'd be successful. What a HORRIBLE way to handle the situation! MediaWorld could have taken the financial hit and spun it into insane goodwill and publicity. Instead they come across as the villain that's threatening to pursue legal action against their own customers. If I were a customer who got a €15 iPad, my official response to that e-mail would be, “That'll be a no from me, dawg. Sue me. – Sent from my iPad.”
10. Seed rounds, IPOs, & acquisitions
Adobe announced plans to acquire Semrush, a Boston-based analytics platform that launched in 2008 to help publishers and brands with search marketing, for $1.9B in an all-cash deal at $12 per share, representing a 77.5% premium over the stock's last closing price. Over the past two years, Semrush has added enterprise products focused on monitoring AI visibility, which is what Adobe is most interested in acquiring and adding to its creative suite. The deal has been approved by the Board of Directors of both companies and is expected to close in the first half of 2026.
Peec AI, a Berlin-based AI search analytics platform that enables brands to monitor how they appear in AI search results, raised $21M in a Series A round led by Singular just four months after its seed round, bringing its total amount raised to $29M. Since launching 10 months ago, the startup has acquired more than 1,300 clients and has grown its annual recurring revenue to more than $4M. It plans to use the funds to open offices in New York and add 40 new members to its team.
Peek, a San Francisco-based online booking platform that aims to be the “Shopify for experiences,” raised $70M in a Series D round led by Springcoast Partners. The company also announced the acquisitions of ACME Ticketing and Connect&GO, which expands its reach to over 150M consumers across museums, theme parks, tours, and cultural attractions. Peek processes over $1.5B in bookings each year and powers major attractions including MoMA, the Whitney Museum, the Seattle Aquarium, and the Museum of Ice Cream.
Peak, an Asheville-based startup that… just kidding! That'd be funny though if companies named Peec, Peek, and Peak all raised money at the same time. It'd certainly pique my interest, but writing about it would be a little opaque.
Ramp, a New York City-based finance automation platform that provides corporate cards, expense management, bill pay, and accounting integrations, raised $300M at a $32B in a round led by Lightspeed, bringing its total amount raised to $2.3B. The round comes just a few months after raising $500M at a $22.5B valuation in a Series E-2 round, which came just a few weeks after a $200M Series E round at a $16B valuation, which was just three months after a $150M secondary share sale at a $13B valuation. The company recently surpassed $1B in annualized revenue and 50,000 customers. Check back in two weeks for its upcoming $200M round at a $40B valuation!
TULU, a New York City-based on-demand product access platform that installs smart rental units in residential and commercial buildings, giving users short-term access to appliances, tools, and household essentials, expanded its Series A round to $37M, which includes an additional $17M co-led by GreenSoil PropTech Ventures, Bosch Ventures, and New Era Capital Partners. Since launching in 2020, the startup has expanded to more than 60 cities across North America and Europe, serving over 500k residents through thousands of in-building units.
Shipday, a Boston-based delivery management software provider that offers real-time driver tracking, dispatching, and order management for restaurants, retailers, and delivery services, raised $7M in a Series A round led by ECP Growth and Ibex Investors Mobility VC, bringing its total amount raised to over $10M. Since completing its seed round in 2023, the company has scaled its platform to serve over 5,000 businesses across 100 countries and 30 languages. It plans to use the funds for product development and further global expansion.
Tailor, a headless ERP platform that provides modular back-office infrastructure for commerce and SaaS companies, raised $37M in a Series A round, adding $15M in new capital i-nest capital, ALPHA, and Sumitomo Mitsui Trust Bank, and building on earlier 2025 rounds backed by NEA and Y Combinator. The company plans to use the funds to accelerate development of its inventory, purchasing, and finance modules, build AI capabilities into its platform, and hire staff for its customer success and implementation teams.
Reelables, a logistics technology company that provides ultra-thin smart shipping labels for real-time cargo tracking across global supply chains, raised $10.4M in a Series A round led by Amigos Ventures and other investors. The company will use the funds to grow its engineering and operations teams, advance its smart label product development, and expand its manufacturing capacity to 100M labels per year. Unlike other companies that offer cellular tracking solutions that require pairing and barcode scanning, Reelables' paper-thin 5G smart labels can be used as the shipping label printed from a thermal barcode printer, offering a low-cost, high-volume smart labeling option.
Addi, a Colombian fintech that provides BNPL financing and digital credit solutions, secured a $71M credit facility expansion led by Fasanara Capital, with participation from Goldman Sachs and BBVA Spark. The company's BNPL platform is used by more than 2.5M consumers and 30,000 merchants and aims to build a more inclusive credit infrastructure in Latin America.
GrubMarket, a foodtech platform that connects farmers and wholesalers with businesses and consumers, acquired Procurant, a supply-chain software provider that offers cloud-based procurement, food safety, and traceability tools for perishable food retailers and suppliers, for an undisclosed amount. The deal expands GrubMarket’s SaaS and AI portfolio and brings more than 850 customers into its network.
Chargeflow, a chargeback-automation startup that uses AI to help e-commerce brands fight and recover disputed transactions, raised $35M in a Series A round, including a $10M debt facility, led by Viola Growth, bringing its total amount raised to $49M. The company tripled revenue YoY and now powers over 15,000 merchants worldwide. It will use the funds for product development and to scale its global go-to-market strategy.
RedSail Technologies, a pharmacy-software and services provider, acquired RxMile, a delivery management platform for independent pharmacies, for an undisclosed amount. By integrating RxMile's platform, RedSail aims to strengthen its delivery operations across its network of 12,000 pharmacies that serve more than 10M patients each month, empowering its clients to better compete with larger providers.
UJET, a San Francisco-based AI-powered contact center platform, acquired Spiral, a Seattle-based startup that provides conversational AI tools for B2B sales and customer support, for an undisclosed amount. Moving forward the company will operate as Spiral by UJET and continue to operate as a standalone offering, while also integrating into UJET's cloud contact center platform. Spiral previously raised $7M from notable investors including Bezos Expeditions and has less than 10 employees, which will all join UJET since the whole team can practically carpool to work together.
PayPal signed a new agreement giving KKR, a global investment firm, up to €6B in replenishing loan capacity to purchase as much as €65B of its BNPL receivables across five European markets including France, Germany, Italy, Spain, and the UK. The deal extends their 2023 partnership and supports PayPal’s balance-sheet-light approach, with PayPal continuing to handle underwriting and servicing.
Feroot Security, a Toronto-based cybersecurity platform that protects web applications from client-side attacks such as skimming, form jacking, and malicious scripts, raised $14M in a Series A round led by True Ventures, bringing its total amount raised to $25M. Feroot addresses the client-side environments where users interact with sensitive data such as login pages, checkout flows, patient portals, and user registration forms, which are prime targets for data exposure through third-party scripts and unauthorized code injections. The company has grown 300% YoY and plans to use the fresh funds to expand its AI agent capabilities and scale its go-to-market team.
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Paul E. Drecksler
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PS: Why was 69 afraid of 70? Because they had a fight and 71.