#250 – PayPal takes over agentic commerce, OpenAI restructures, & Amazon might actually do it

by Paul Drecksler | Nov 3, 2025 | Recent Newsletters

Hi Shopifreaks

Last week I presented my new video series 90 Second Pitches — an innovative way to discover e-commerce apps and SaaS products that help you grow your store. We kicked off the series with a pitch from Carson and Bridger Hart, founders of Infinite Color Search, a revolutionary way for shoppers to discover products by color on your Shopify site.

I'm happy to share that the 90 Second Pitches concept got great feedback! It's always nerve-wracking to launch a new project, but from the responses I received, folks seem as excited for this one as I am.

If you didn't get a chance to watch Infinite Color Search's pitch last week, here are links to the 90 Second Pitch on LinkedIn and the Full 60 Minute Interview on YouTube where we dive deeper into the product, how it works, and their startup story.

I've got another great pitch for you next week by a startup that offers the fastest way I've ever seen to conceptualize, design, and publish dozens of creatives for Meta ad campaigns. So stay tuned!

Want to pitch your startup? Hit reply and show me what you're working on! I'd love to feature your e-commerce app or SaaS solution too.

Now let's see what's new in e-commerce…

In this week's edition I cover:

PayPal takes over agentic commerce payments
OpenAI restructures as a for-profit
Meta's AI ad targeting gets pushback
Shopify loves Seth Rogen
Amazon might partner with 3rd party AI companies
Shop App product listings are now indexable
President Trump met with President Xi
Automattic strikes back against WP Engine
Elon Musk launches Grokipedia
Pinterest's new AI Assistant
Etsy's new CEO
Amazon cuts 14,000 corporate jobs

All this and more in this week's 250th Edition of Shopifreaks. Wow, 250 editions already!? Thanks for subscribing and sharing!

Stat of the Week

OpenAI revealed that roughly 0.15% of ChatGPT’s 800M weekly users — more than one million people — engage in conversations showing signs of suicidal intent or planning. The company said it consulted over 170 mental health experts to improve how GPT-5 responds to users in crisis, claiming the new model now delivers 65% more appropriate replies than previous versions. OpenAI also reported hundreds of thousands of users show signs of psychosis, mania, or emotional attachment to the chatbot, adding to growing concerns about AI’s role in mental health support.

1. PayPal is positioning itself as the #1 digital wallet in agentic commerce

There was a flurry of news surrounding PayPal and agentic commerce last week, with every company involved in the partnerships distributing their own announcements and press releases. Let's break it down and make sense of all the noise:

1) PayPal launched Agentic Commerce Services, a suite of tools that enable merchants to make their products discoverable across AI platforms and shoppable through PayPal’s payment infrastructure, identity verification, and buyer protection systems.

Here's what Agentic Commerce Services includes:

Agent Ready – the name for PayPal's solution that enables merchants to accept payments via AI chatbots and browser automations with built-in fraud detection, buyer protection, and dispute resolution.
Store Sync – a catalog and order management system that makes merchants’ product data discoverable across AI channels and automatically routes orders to their existing fulfillment systems.
Customer Ownership – sellers remain as the merchant of record so that customers buy from their brand (versus OpenAI appearing on the credit card statement), and the merchant owns the customer data like name, e-mail, shipping address, etc (unlike Amazon, which owns the customer).
Multiple AI Integrations – one single PayPal integration connects merchants to multiple AI ecosystems including Perplexity, OpenAI, Google, and PayPal's upcoming AI shopping agent, with more to follow.
Multiple Platform Integrations – PayPal's new agentic commerce services work in partnership with Wix, Cymbio, Commerce, and Shopware.

Basically PayPal is positioning itself as the bridge that connects merchants directly to all AI ecosystems either through its own merchant services or in partnership with major e-commerce platforms. While Wix, BigCommerce, and other platforms support multiple payment types, this sure gives merchants incentive to accept PayPal!

Okay so next up…

2) PayPal signed a deal with OpenAI to be the first digital wallet embedded into ChatGPT, allowing users to pay for items discovered through the chatbot. PayPal will manage merchant routing, payment validation, fraud protection, and other seller processes so that merchants don't have to sign up with OpenAI directly. As for buyers, they'll receive the same convenient payment methods, protections, package tracking, and dispute resolution that they're accustomed to through PayPal.

PayPal CEO Alex Chriss said:

“We’ve got hundreds of millions of loyal PayPal wallet holders who now will be able to click the ‘Buy with PayPal button’ on ChatGPT and have a safe and secure checkout experience. It’s a whole new paradigm for shopping. It’s hard to imagine that agentic commerce isn’t going to be a big part of the future.”

As you might recall from last month, OpenAI developed is Agentic Commerce Protocol, which powers its Instant Checkout feature, in partnership with Stripe. The protocol was later adopted by Etsy, Shopify, Salesforce, and now PayPal.

So while technically Stripe's Link wallet was the first integration, Link cannot yet store funds and has no consumer mobile app, so many folks don't consider it a “full wallet.” Whereas PayPal provides the full spectrum of digital wallet services (and pretty much invented the category).

What's odd about the PayPal + OpenAI announcement, which was released the same day as PayPal's Agentic Commerce Services announcement, is that the former doesn't mention the latter and vice-versa. The OpenAI release doesn't use the words “Agentic Commerce Services” anywhere and that announcement doesn't mention “OpenAI.” So I guess they wanted to separate the two overlapping announcements so that OpenAI could properly capture headlines.

Last but not least…

3) PayPal also adopted Google's Agent2Agent (A2A) Protocol and integrated with its Agent Payments Protocol (AP2), which is a payments layer built on top of A2A and the Model Context Protocol (MCP) that provides accountability and fraud controls.

In layman's terms… Google and OpenAI offer competing protocols that effectively do the same thing, and now PayPal supports both of them. Merchants who sell through PayPal or enable PayPal payments through partnering platforms can now get the best of both worlds in regards to the two biggest AI payment ecosystems at the moment.

Technically it's a big more nuanced than that — as Agentic Commerce Protocol is strictly built around commerce and Agent2Agent Protocol centers around interoperability between AI agents (with commerce a part of it) — but for the sake of these announcements, the gist is that “PayPal is everywhere” when it comes to the major agentic commerce ecosystems.

2. OpenAI completes its restructuring into a for-profit Big Tech goliath

OpenAI completed its yearlong restructuring last Tuesday that will allow it to go public. The transition converts the prior investments made by Microsoft and other backers into regular equity, with Microsoft owning 27%, OpenAI Foundation (its nonprofit arm) taking 26%, OpenAI employees owning 26%, and other investors collectively owning 20%.

Altman doesn't have a stake in the company, according to The Information sources, but is heavily invested in companies that do business with OpenAI — which is NOT a conflict of interest because those types of rules don't apply anymore.

Quick History of OpenAI's structure:

OpenAI began in 2015 as a nonprofit research lab founded by Sam Altman, Elon Musk, and others with the mission to develop safe artificial intelligence that benefited humanity.
In 2019, it created a for-profit subsidiary, OpenAI LP, under a “capped-profit” model that allowed investors to earn up to 100× returns while the nonprofit parent retained ultimate control.
That unusual hybrid structure drew scrutiny for giving investors influence without shareholder rights and for the lack of transparency around who actually governed the company.
Elon Musk left the board in 2018 amid disagreements over the company’s direction and later sued OpenAI in early 2024, accusing it of abandoning its nonprofit mission and becoming a “closed-source, profit-driven” arm of Microsoft.
The lawsuit was dismissed, but invited questions over whether OpenAI’s close partnership with Microsoft, which invested over $13B in the company, undermined its independence and commitment to open research.
Several former employees and AI ethicists criticized OpenAI's secretive governance, limited oversight by the nonprofit board, and unclear boundaries between OpenAI’s nonprofit and for-profit entities.
Sam Altman didn't give a fuck what any critics thought and pushed the transition through.

Under the new structure, shareholders won’t get direct input over how OpenAI is run, but the deal lifts a prior cap on the potential financial return that they could receive from their stake.

Also as part of the agreement, Microsoft secured a commitment from OpenAI to spend $250B renting its servers over an unspecified period, similar to the commitment OpenAI recently made with Oracle. So Microsoft invested $13B and gets $250B coming back to it, plus equity in the company? That's a hell of a deal! (Assuming OpenAI can later afford it.)

Is OpenAI going to have an IPO?

CEO Sam Altman told employees last week that a public offering was bound to happen in the future, but didn't provide a specific date. Later in a public livestream video, he said an offering was likely “given the capital needs we will have.” (You know… the $1.4 trillion worth of future-dated checks OpenAI has written that it doesn't currently have the money or revenue to support!)

Rumor are already circulating that an IPO could come as soon as 2026 and value the company at up to $1 trillion — which would put it last position on the list of top 10 publicly traded U.S. companies by market cap (based on current valuations).

An OpenAI spokesperson told Reuters:

“An IPO is not our focus, so we could not possibly have set a date. We are building a durable business and advancing our mission so everyone benefits from AGI.”

However OpenAI might not be able to afford to wait, so realistically the IPO could be sooner than they admit.

3. Should Meta target ads based on convos with their AI chatbots?

Privacy watchdogs sent a letter to FTC Chair Andrew Ferguson, urging the FTC to stop Meta from moving forward with its plan to target ads to Facebook, Instagram, Threads, and WhatsApp users based on their conversations with chatbots.

Meta first revealed its plans to do so in early October, set to begin targeting users by Dec 16th. The company said at the time it will target ads and content to users if, for example, they talk to their chatbot about hiking, traveling, or shopping, but will avoid using personal or difficult conversations you have with its AI, such as about a relationship or depression, to serve ad content.

The Electronic Privacy Information Center, Center for Digital Democracy, and other groups argue that Meta's plans cross a line:

“This unprecedented use of deeply sensitive data presents outsized risks to consumer data privacy and security. Meta’s plan to repurpose conversational AI data for advertising illustrates the dangers of regulatory inaction: absent intervention, the practice will normalize a level of surveillance that is qualitatively more intrusive than traditional behavioral tracking.”

The organizations also claim that Meta's plan is “at odds with” an FTC settlement from 2020 that requires the company to conduct detailed reviews and privacy assessments for each new service that collects or uses consumer data, and then subsequently implement privacy safeguards in response to any risks discovered. (Gotta love those self audit requirements!)

The advocacy groups argue that AI conversational data is a level above other user data:

“At a minimum, this category of data should be treated as sensitive information requiring affirmative, opt-in consent from adults (and a categorical prohibition on monetization of youth data) before it can be used for advertising. Failing to impose this standard would effectively permit firms to unilaterally exploit the most private forms of digital interaction for commercial gain.”

The outcome of the efforts by these privacy watchdogs (if any) could have a substantial impact on if / how other AI companies are permitted to use AI chatbot conversations to target ads, as well as how they handle the usage of that data.

Meta is the first company to try and target users based on their conversations with chatbots on a massive scale, but it won't be the last, especially with OpenAI and other AI firms integrating commerce into their chatbots. Ads are about to become part of the AI experience in a big way!

Should Meta be allowed to use your chatbot convos to target you with ads? Should opt-in be required? Hit reply and let me know or join the conversation on LinkedIn.

4. Is Shopify giving preferential treatment to Seth Rogen?

Yes, that Seth Rogen — the actor from Knocked Up, Superbad, Neighbors, The Interview, and other comedy classics.

Retailers selling cannabis accessories online are claiming that Shopify is giving Rogen preferential treatment by allowing his smoking lifestyle brand to use its payments technology, Shopify Payments, to process orders while blocking them from doing so.

Rogen's retail site, Houseplant, sells ashtrays, grinders, and rolling papers using Shopify Payments, and was recently highlighted at an event in New York, where Shopify President Harley Finkelstein presented Rogen with an award for hitting 100,000 orders on the platform.

Justin Johnson, co-founder and CEO of Chill Steel Pipes said his company is unable to sell products similar to Rogen's through Shopify Payments, requiring them to use a more expensive third-party order processing company as well as pay Shopify additional transactions fees that are waved if merchants use Shopify Payments, which costs him tens of thousands of dollars additional in fees each year.

Other cannabis accessory retailers also claim that they're being asked to adhere to a different interpretation of Shopify's rules than Rogen's store.

Johnson asked Shopify why his business was being treated differently to Rogen's and was told he would be allowed to use Shopify Payments if he removed two products from this website (a jar and a dab stool set), and if his company made “zero reference of cannabis” on its social media. Seems fair, except Houseplant's Instagram blatantly features photos of Rogen getting high with the word “weed” in the caption.

Most merchants who spoke to The Logic seemed like they were willing to comply with Shopify's rules surrounding cannabis products, but would appreciate more transparency around the rules and equal enforcement. In other words, you shouldn't have to be a celebrity to sell cannabis items through Shopify Payments.

5. Amazon says it may partner with third-party AI companies in the future

Amazon CEO Andy Jassy made a very strategic quote regarding the company's future of working with third-party AI companies. Jassy said:

“We’re also having conversations with and expect, over time, to partner with third-party agents. Today, search engines are a very small part of our referral traffic, and third-party agents are a very small subset of that. But I do think that we will find ways to partner.”

His statement strategically counters the conversation that Amazon is unwilling to partner with third-party agents and subsequently falling behind to Shopify, Walmart, and other marketplaces by not partnering with OpenAI, while simultaneously downplaying the actual impact of those partnerships.

Basically Jassy is saying — “We're open to it in the future under the right terms, but we're not really missing out on anything right now by not playing monkey-see, monkey-do.”

Amazon's got something that all those companies don't have combined:

Almost a quarter billion Prime members subscribed worldwide.
An incomparable fulfillment & logistics network that offers shipping cost and speeds inaccessible to most Shopify merchants.
Brand loyalty and consumer habits that took decades to earn them a 60% market share as the starting point for shopping amongst U.S. consumers.

Then again, Jassy might be intentionally minimizing how much of Amazon's traffic comes from search engines, which Similarweb estimates to be around 14%.

Do you think holding off on partnering with third-party AI shopping agents will ultimately be the right long term move for Amazon? Hit reply and let me know or join the conversation on LinkedIn.

6. Shop App now runs on Shopify Catalog and product listings are indexable

Shopify announced that the Shop App now runs on the Shopify Catalog, creating a single data layer that powers product discovery across AI-driven and organic channels. Before this change, Shop App had its own product feeds and sync processes, but now it pulls from the same source of truth, Shopify Catalog, as the merchant's online store, Facebook, Instagram, Google, and other channels.

I asked Shopify's Senior Solutions Engineer, Khalid Chao:

“Is Shop App effectively the bridge that connects a Shopify store to OpenAI? Or will Shopify stores be able to connect their products directly to Instant Checkout without going through Shop app? In other words, a merchant must have a presence on Shop App to take advantage of OpenAI's instant checkout?”

I haven't gotten an answer yet from Khalid and couldn't find an answer elsewhere, but perhaps check that link above in the future to see if he responds. Alternatively, if you know the answer, please hit reply and let me know.

Additionally, Shopify announced that Shop storefronts can now be indexed by Google and Bing, whereas they previously existed in a closed ecosystem within the Shop mobile app and Shop.app website. In other words, your products on Shop App weren't visible on Google; only the product listings on your website were.

I'm curious the impact this change will have on a shop's SEO presence.

On one hand… the change could give a lift to Shopify stores with weak SEO and low domain authority. They might have a better shot at ranking their products on Shop.app than on their own website, similar to how Amazon listings often outrank a brand's own D2C website.

On the other hand… the move could cannibalize the SEO ranking of merchant domains. Meaning if Google starts ranking Shop App URLs higher than merchants' own store URLs, traffic could shift from their D2C websites to their product listings on Shop.app, which means Shopify, not the merchant, controls the top-ranking page for their branded searches.

Shopify did say in their help documentation that merchants can choose whether their product listings on Shop.app can be indexed and displayed on search engines — so it's up the the individual merchant whether they have their product listings index on both their D2C website and on Shop.app. However, will they eventually have a choice? If competing brands that have had traditionally lower SEO authority begin outranking their website product listings via their Shop.app product listings, that brand might not have much choice but to hop on the Shop.app SEO Bandwagon.

I decided to ask SEO expert Sam Wright, who runs the Blink SEO agency, what his thoughts were on the subject. You can view the video on LinkedIn for his opinions on the potential impact of the changes.

7. President Trump and President Xi meet face-to-face in South Korea

President Trump and President Xi met in Busan, South Korea last Thursday, marking the first in-person meeting of the two leaders since Trump took office in January for his second term, where they supposedly crafted a one-year agreement on trade relations.

Trump said on Thursday that the 20% tariffs on China related to fentanyl were being reduced to 10%, bringing the total effective tax rate on Chinese imports from 57% to 47%.
Beijing said it would delay imposing dramatic restrictions on rare earth minerals, which are key materials for the production of computer chips used in smartphones, AI datacenters, and defense technology.
Xi also authorized China to begin the purchase of Soybeans, Sorghum, and other farm products to return purchases to annual levels recorded prior to recent trade tensions.
Trump said he believes the one-year deal will be “routinely” extended.

What about the TikTok deal?

U.S. Treasury Secretary Scott Bessent told Fox News on Thursday that China had “finalized” its approval in recent days, but that, “I would expect that would go forward in the coming weeks and months, and we'll finally see a resolution to that.”

I mean, you can keep using the words “final,” “finalized,” and “finally” as many times as you want, but I still don't see a closed deal.

China, of course, has offered no statements on the matter, other than to say that the two countries planned “to properly resolve issues” related to TikTok.

The news surrounding this U.S.-China TikTok deal is beginning to feel like the Photoshop file structure of a graphic designer saving their work as “tiktok-deal-final-final5.psd”

As I've said since the beginning, I'll believe it when I see it. For now though, no updates as of Thursday on the “final finalized” TikTok deal. And that's final!

8. Automattic alleges trademark appropriation and bad faith by WP Engine

It's been a minute since we've talked about the Matt Mullenweg vs WP Engine beef — and that's a good thing for the WordPress community because, for a while, it was getting embarrassing. However now some new information has surfaced.

PPC Land reports that Automattic filed comprehensive counterclaims against WP Engine for engaging in “deliberate misappropriation of WordPress-related trademarks” following Silver Lake's 2018 acquisition of a controlling interest in the company. The document details how WP Engine allegedly “sought to inflate its valuation and engineer a quick, lucrative exit” through systematic trade infringement.

Here's a brief timeline of events regarding the Automattic vs WP Engine beef:

In September 2024, Automattic CEO Matt Mullenweg called out WP Engine at the WordCamp US event for not contributing enough to the WordPress open source project, claiming that Silver Lake doesn't care about the WP ecosystem and only cares about making money. He encouraged users to switch hosts and get off WP Engine.
Following the event, he continued to speak publicly against WP Engine.
WP Engine quickly sent a “cease and desist” letter to Automattic, demanding that Mullenweg stop making and retract false, harmful, and disparaging statements against the company.
A few hours later, Automattic responded with its own “cease and desist” letter to WP Engine, demanding that the host stop “improperly using” the trademarked terms “WordPress” and “WooCommerce,” which it says causes confusion amongst customers.
It became public that prior to kicking off the beef with WP Engine at WordCamp, Mullenweg demanded either 8% of WPEngine's $400M annual revenue to license the trademarks, or an equivalent amount of developer hours donated to The WordPress Foundation.
Shortly after, in retaliation of the “cease and desist” letter, Mullenweg blocked access to the WordPress.org Plugin Repository for WP Engine's 1M+ customers and updated their trademark policy to include instructions on proper use of “WP,” specifically calling out WP Engine on the page.
Not everyone at Automattic agreed with Mullenweg on the way he was handling things with WP Engine, so he cleaned house of all dissent at the company by offering employees the option to resign immediately and receive $30k or six months of salary, or stay and kiss his ring.
Eventually a judge required that Mullenweg backpedal on some of his retaliatory changes during the ongoing legal battle, which hasn't seen many updates since then.

Flash forward to Oct 23rd, 2025…

Automattic is alleging in its new counterclaim:

WP Engine “sought to inflate its valuation and engineer a quick, lucrative exit” through systematic trademark infringement.
WP Engine abandoned its fair usage of the WordPress trademarks following Silver Lake's investment.
WP Engine anointed itself as “The WordPress Technology Company” and allowed partners to refer to it as “WordPress Engine.”
WP Engine committed 5% of its resources to supporting the WordPress project, but never kept its promise.
These actions were “not isolated branding choices but a coordinated scheme to misappropriate the WordPress and WooCommerce trademarks, mislead consumers, and inflate WP Engine's valuation for an anticipated sale.”
By 2024, Silver Lake's strategy to inflate its valuation and sell for more than $2B was failing, as no buyer valued the company near that amount.

The lawsuit between Automattic and WP Engine will continue in the Northern District of California, with more news to come. I'll keep you posted in the future as I learn more.

9. Other e-commerce news of interest

Walmart is rolling out new AI-powered tools for its Scintilla data platform (formerly Walmart Luminate) to help suppliers better analyze customer behavior and marketing performance. The updates include a conversational assistant to explain metrics, AI-generated summaries of customer survey results, and smarter advertising recommendations through Walmart Connect. The company says the tools will make it easier for merchants to understand customer attitudes, forecast demand, and activate insights across campaigns as Walmart expands its data and retail media capabilities.

Meta Threads introduced new ad formats and verification options in preparation for the holiday season. Advertisers can now run additional video, image, and carousel ads through Meta’s Marketing API, with support for all video aspect ratios and taller 4:5 formats on the Threads feed. The platform, which reaches about 400M monthly users, of which Meta says 75% follow at least one business, is also adding third-party verification partners to give brands more transparency and confidence in campaign performance.

Elon Musk unveiled Grokipedia, an AI-generated version of Wikipedia that creates and edits entries using xAI. Musk claims that Grokipedia will “purge out the propaganda” on Wikipedia, which has faced increasing criticism from conservatives in recent months for being too “woke” and left-leaning. Musk heavily criticized the site in January after the entry on him was edited to include the Nazi salute he threw during a celebratory speech honoring President Trump's inauguration. Grokipedia is already drawing backlash for its right-wing and sometimes inaccurate content. Fery Kaszoni, CEO of Search Intelligence, called the move “the biggest SEO heist the world has ever seen, with large scale AI content generation.” However I see it as just the first of many large-scale AI-generated encyclopedias headed our way in the near future.

Walmart has shifted from its 2019 stance of keeping search results ad-free to making sponsored listings a central part of its online marketplace's experience, according to a study by retail analytics firm Pentaleap. The report found that ads now appear in 97% of searches, often taking the top spots and pushing organic listings down the page, nearly matching Amazon’s saturation levels. Walmart generated $4.4B in ad revenue in 2024, up 27% YoY, as brands increase spending to stay visible in search. Under chief growth officer Seth Dallaire, a former Amazon executive, Walmart has embraced the “pay-to-play” model that helped turn retail search advertising into a core profit engine.

Pinterest launched Pinterest Assistant, an AI-powered, visual-first collaborator that helps users discover and shop for products that match their personal style, aiming to solve the “I'll know it when I see it” problem that customers face when shopping. For example, if a user searches, “I need new throw pillows that match my living room decor,” Pinterest Assistant will draw from their saves, boards, collages, and other users with similar tastes to deliver pillows tailored to their specific design aesthetic. The assistant also uses multimodal AI to combine images, text, and voice input when shopping. Bold decision to call it something general like “Pinterest Assistant” versus something kitschy “Pinny” or “Doofus.”

Amazon executives strategized about limiting public disclosure of the company’s total datacenter water consumption to avoid reputational risk ahead of its 2022 “Water Positive” campaign, according to leaked documents viewed by The Guardian. The memo advised reporting only “primary” water use (about 7.7B gallons annually), while omitting secondary water use tied to electricity generation, which would have roughly doubled the total. Scientists and former employees criticized the selective reporting, saying it obscures Amazon’s true water footprint as the company builds new datacenters in drought-prone regions. Amazon called the document “obsolete” and said it “misrepresents” its current sustainability strategy — which is pretty much becoming their response to any accusatorial news reports.

Grubhub is partnering with Instacart to offer grocery ordering through its app, marking the first time that Instacart has embedded its grocery shopping experience into a third-party platform. Grocery orders will be fulfilled by Instacart drivers, with members of Grubhub+ having their orders of $25 or more delivered for free. The move is meant to help Grubhub catch up to DoorDash, which owns a 70% share of the app-based food delivery market in the U.S.

Etsy is testing a new “Top Buyer” badge that highlights big spenders on the platform and encouraging sellers to give them priority customer service. How does a customer spending a lot of money with other sellers mean I should treat them any differently on their first purchase with me? Also as a buyer, it feels like an invasion of privacy for a seller to know that I spend a lot on the platform. Couldn't knowing that I'm a big spender make the seller more likely to kidnap my kid and hold her hostage for ransom? I'm obviously being facetious, but my point is, don't inform strangers of my spending habits! Some Etsy sellers appreciate the feature and see it as a way to keep shoppers happy who are more likely to make a purchase, while others noted that just because they spend a lot on the platform doesn't make them more likely to be a good customer, as in leave positive reviews or not return their purchase.

Walmart opened its Marketplace Seller Forum to all sellers after a limited beta, creating an official community space for merchants to share insights and get support directly from Walmart moderators. The forum features anonymous profiles, badges, and organized categories covering fulfillment, advertising, APIs, and policies. Alongside the launch, Walmart introduced Skills Certification Courses, which offer short, lessons teaching sellers how to use Marketplace tools effectively. The move comes at a good time, given that Walmart just recently surpassed 200k sellers earlier this year — 44k which joined during the first five months of 2025 alone.

TikTok unveiled new AI-powered tools for creators at its U.S. Creator Summit including Smart Split, which automatically clips, captions, and reframes long videos into TikTok-ready shorts, and AI Outline, which generates titles, hooks, and video structures based on user prompts and trending topics. TikTok also announced an update to its Subscription program, allowing eligible creators to earn up to 90% of revenue after fees, up from its standard 70% cut.

Etsy CEO Josh Silverman is stepping down from the role after over 8 years of running the company, effective Dec 31, 2025, to be replaced by Kruti Patel Goyal, Etsy's current President and Chief Growth Officer. Goyal previously served as CEO of Depop, the resale marketplace Etsy acquired in 2021 for $1.63B, where she nearly doubled gross merchandise sales and the buyer base. Goyal is hosting a live AMA on November 4th to answer questions about the leadership transition and her vision for the platform in the new year.

Poshmark named Heather Friedland as its first-ever Chief Product Officer, following multiple executive departures including 3 of the 4 co-founders stepping down over the last several months. Friedland previously served as CPO at Ancestry and Glassdoor, and held senior roles at eBay, where she oversaw seller tools and data-driven technologies. Her focus will be on enhancing marketplace innovation and leveraging AI to elevate the shopping and selling experience, while leading upcoming initiatives like Smart List, Smart Sell, and the recently revamped discovery feed.

Amazon is planning to cut as many as 30,000 corporate jobs as it slashes expenses and compensates for overhiring during the pandemic, according to Reuters sources. The figure represents just 1.9% of Amazon's total 1.55M workforce, but around 8.5% of its roughly 350k corporate employees and marks Amazon's largest job cut since late 2022 when it eliminated 27k positions. Amazon later published a blog post indicating that the number of affected employees was closer to 14,000. Jamie Siminoff, the founder of Ring, which later sold to Amazon, and current Amazon VP of product, told Business Insider that the layoffs were “not really financially driven,” nor were they “really AI-driven, not right now at least,” but they were rather about “culture.” Business Insider later called Amazon's layoffs a “drop in the bucket after its pandemic-era hiring spree.” Leave it to Business Insider to shill pro-Amazon propaganda after negative news surfaces about the company. It's like clockwork, every time.

The Trade Desk partnered with Shopsense AI to serve contextual sponsored product ads alongside editorial content on publisher websites. Shopsense uses AI and machine learning to identify commerce intent in images, text, and video on sites like Disney, Vox Media, and BuzzFeed, and then enables The Trade Desk to place shoppable product listings, such as Nike shoes beside a marathon article, via its OpenPath integration. The move expands The Trade Desk’s retail media push beyond retailer sites like Gopuff and into premium publisher inventory, turning traditional ad impressions across CTV, web, and audio into commerce-driven, shoppable experiences.

Grammarly is changing its company name to Superhuman, which it acquired in July, to better represent that it's now a multi-product company that includes Grammarly, Coda (acquired in Dec 2024), Superhuman Mail, and a newly launched AI assistant called Superhuman Go. The new assistant integrates across apps like email, calendar, and documents to proactively help users write, schedule, research, and automate tasks in real time. For example, if someone suggests scheduling a meeting during a conversation, Go will surface your availability and help you book the meeting in the moment. Grammarly, now part of the broader Superhuman suite, will continue to serve as one of several specialized agents accessible through Go

Facebook released its first major brand campaign in four years called “A Little Connection Goes a Long Way.” The featured spot, “Home for the Holidays,” follows a group of friends reuniting in their hometown after coming up with the idea in a Facebook message. Meta says the campaign aims to reminder users “what made Facebook magic in the first place” and is part of Meta's push to rebuild relevance among younger Millennial and Gen Z audiences. The spot will air on TV during college football and NBC’s Wicked special, as well as across Peacock, Disney+, Netflix, and Prime Video, with extensions running on competing platforms including TikTok, Snapchat, Pinterest, Reddit, and podcasts.

Obviously Meta didn't use its own AI advertising tools to create the spot, because if it had, the campaign might have accidentally been very different! Advertisers are reporting strange outcomes from Meta’s AI-powered ad tools, including an “AI grandma” image replacing a men’s clothing ad and a model with a twisted leg in a shoe campaign. Brands like True Classic, Kirruna, and Lectric have encountered off-brand or surreal ads even after disabling Meta’s “Advantage+” creative settings. Some marketers say Meta’s system has been automatically re-enabling AI features, forcing agencies to manually monitor accounts several times a week.

Elon Musk revealed on the All-In podcast that his viral 2022 video carrying a sink into Twitter’s headquarters almost didn’t happen because his security team struggled to find a store willing to sell “any kind of sink.” Musk said the store's employees were confused by the request since most buyers need one for specific plumbing, and almost didn't sell the sink because they didn't want to sell the wrong one. Musk joked that “it’s just rare that somebody wants a sink for sink’s sake.” Oh no! What a loss that would've been if that joke never got made…

Amazon announced that it officially surpassed $20B in cumulative e-commerce exports from India since launching Amazon Global Selling in 2015. Back in 2020, Amazon initially pledged to enable $10B in exports from the country by 2025, but later revised its projection to $20B. It is now working towards a target of $80B in exports by 2030, in line with the Government of India's goal of reaching $200-300B by 2030 (collectively across all exporters, not just Amazon).

Amazon announced that it will begin reporting information about China-based sellers to China's tax authority including sellers' identify, number of transactions, revenue, commission and services fees. The move follows a new law in China that requires all Chinese Amazon sellers to send quarterly reports to China's tax bureau. Jon Elder, founder of Black Label Advisor, said that this news “paired with the new tariffs and the de minimis loophole being closed” means that the Amazon marketplace “is going to be increasingly fairer for sellers from all over the world” due to Chinese brands quitting over their margins getting erased. Then again, not ALL Chinese sellers are guilty of under-reporting their U.S. revenue on Amazon to avoid taxes, so the actual impact is yet to be seen.

AliExpress is introducing a new Best Price Guarantee program that it says will match over 1,500 branded products from Amazon, Temu, Shein, and eBay. Customers shopping for items in its Brand+ channel marked with Best Price Guarantee on the product page can request a refund of the difference if they can find a lower price on another e-commerce platform within seven days of purchase. The move is designed to inspire confidence amongst customers when shopping on the platform that they are getting the best possible price. Couldn't I just return the item to AliExpress and buy it on the other platform if I found it cheaper? I guess this new program prevents customers from having to do that, which objectively offers a better shopping experience. Bonus points if AliExpress tracks the price on other platforms themselves and offers an automatic refund (instead of the customer having to request it). That'd be the real boss move.

🏆 This week's most ridiculous story… Meta asked a U.S. district court to dismiss a lawsuit alleging that the company illegally torrented pornography to train its AI models. The move comes after adult content creator Strike 3 Holdings discovered illegal downloads of some of its adult films on Meta corporate IP addresses and brought a lawsuit against Meta seeking $350M in damages. Meta argued last week that the files were actually torrented for “private personal use,” noting that “tens of thousands of employees,” as well as “innumerable contractors, visitors, and third parties access the Internet at Meta every day” and that while it's “possible one or more Meta employees” downloaded the pornographic videos, it's just as possible that a “guest, or freeloader” or “contractor, or vendor, or repair person” was responsible for the activity. LOL, I'm sure that's the first thing a plumber does when entering Meta HQ. “Excuse me, can I have the WiFi password so I can torrent my dirty flicks?” Either way, Meta would likely have logs of who accessed their corporate WiFi versus guest network.

10. Seed rounds, IPOs, & acquisitions

Whatnot, a livestream shopping marketplace that connects buyers and sellers through real-time auctions for collectibles, fashion, and other items, raised $225M in a Series F round co-led by DST Global and CapitalG, bringing its total amount raised to $968M and more than doubling its valuation to $11.5B in less than 10 months. The company, which has already generated over $6B in live sales in 2025, plans to use the funds to fuel its expansion across the US, UK, and Europe

Lula Commerce, a digital commerce platform that helps convenience stores and quick-service restaurants manage online orders, inventory, and delivery integrations, raised $8M in a Series A round led by SEMCAP AI, bringing its total amount raised to $16M. Lula Commerce consolidates third-party delivery services like Uber Eats, DoorDash, and Grubhub into a single dashboard and automates key functions like refunds, reviews, uptime, and inventory management. It plans to use the funds to expand its team across engineering, sales, product, and customer support.

The Prompting Company, a four-month-old San Francisco-based startup that helps brands optimize content so they surface in AI answers, raised $6.5M in a seed funding round led by Peak XV Partners, Base10, Y Combinator, and other investors. The platform identifies and analyzes questions AI agents are asking by probing models to uncover specific purchase-intent queries, and then creates structured content that answers those questions to automatically route AI agents towards. The funding will support platform growth, partnerships, and collaborations with Nvidia.

Amazon is planning to invest more than €1.4B in the Dutch market over the next three years, aiming to win over shoppers in the country from bol, the leading online marketplace in The Netherlands with over 10x as many selling partners. The move follows Amazon's recent investment of more than €1B in Belgium, where bol is also its main rival.

Wild Moose, an Israeli AI platform that analyzes logs, metrics, and code changes to identify the root causes of production incidents, raised $7M in seed funding and emerged from stealth in a round led by iAngels. Wild Moose has already been adopted by Wix, Redis, GoFundMe, and Lemonade, who report reductions in mean time to resolution by up to 80%. Amazon could've used that last week, LOL.

FundPark, a Hong Kong-based fintech that offers working capital and data-insight solutions for e-commerce businesses, raised $71M in a round led by an Ares Management APAC Credit fund, with equity investment advised by Goldman Sachs. The company, which has already provided more than $6B in advances to over 32,000 e-commerce merchants worldwide, plans to use the funds to advance its AI capabilities and expand internationally.

Homecourt, a home care brand founded by Friends star Courteney Cox in 2022, raised $8M in a Series A round led by Cult Capital. Cox said she was initially afraid to bring on investors that could disrupt her process and branding, but that Cult Capital was focused on enhancing her growth without getting in the middle of creative. She plans to use the funds for expansion, following Homecourt's track record of doubling sales every year since inception.

HubSpot, a CRM platform offering marketing, sales, and content management tools, entered into a definitive agreement to acquire XFunnel, a platform that helps businesses optimize their presence across LLMs, for an undisclosed amount. HubSpot plans to integrate the platform natively into their marketing products, giving clients new insights into how their brand appears across AI answers alongside steps to improve their visibility.

Snapmint, an Indian BNPL platform, raised $125M in a Series B round led by General Atlantic that will serve as an exit to some of its early angel investors, bringing its total amount raised to $140M. The BNPL firm, which launched in 2017 and currently serves 7M monthly active users in India, said it aims to scale its presence to over 100M users over the next few years. Although I'd bet money that it tries to get acquired long before then.

Affirm gained new off-balance sheet funding from New York Life that will support up to $1.75B in annual consumer loan volume. Under the agreement, New York Life will purchase up to $750M in Affirm installment loans on a forward-flow basis through December 2026, deepening a long-term partnership in which New York Life has already invested nearly $2B in Affirm collateral. In its most recent quarter, Affirm reported $10.4B in GMV and $876M in revenue, with active users rising 24% to 23M.

Meta is selling $30B in bonds to help fund its AI datacenter infrastructure, with some bonds not maturing for 40 years! LOL, can you imagine if MySpace sold bonds during its peak in 2005 that matured in 2045? How would that investment have worked out? The move follows its deal with Blue Owl Capital to fund 80% of its datacenter building and a surge in the company's recent capex to fund servers, networks, and datacenters, which has spooked investors. Meta expects 2025 capex to reach up to $72B.

Level, a digital marketing firm backed by private equity firm Dubin Clark, acquired BAM Strategy, a New York-based developer of CRM and loyalty programs for consumer brands, for an undisclosed amount. The merger combines Level’s AI-driven performance marketing and analytics with BAM’s strengths in creative development, CRM, and loyalty programs, creating a 250-person agency spanning the entire customer lifecycle from acquisition to loyalty. BAM will continue operating under its brand, but the firms will integrate data, technology, and creative teams.

Shadowfax Technologies, an Indian logistics company offering e-commerce express parcel, hyperlocal, and value-added delivery services, filed for an IPO with India's SEC, seeking to raise up to Rs 2,000 crore (around $240M USD). Around half of the issued shares are fresh equity, while the other half come from existing shareholders. The company plans to use the net proceeds for expanding its network infrastructure, financing lease payments for new first-mile, last-mile, and sorting centers, and potentially acquisitions.

Groww, India’s largest online brokerage by users, is set to launch its IPO this week, seeking to raise Rs 1,060 crore ($127M) and valuing the company at about Rs 61,700 crore ($7.4B). Founded by former Flipkart employees, the Bengaluru-based firm currently serves over 14M active clients and has tripled profits YoY. The IPO is expected to be one of this year's largest in the country.

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Paul E. Drecksler
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PS: Did you hear about the naked woman that robbed a bank? None of the witnesses could identify her face.