#243 – Netflix loves Amazon, Gmail’s new tab, & the FTC gets serious

by Paul Drecksler | Sep 15, 2025 | Recent Newsletters

Hi Shopifreaks

Welcome to all the new subscribers who joined from Sam Wright's post yesterday. Thanks for the shout out Sam! You've got great taste in newsletters. 😂

Speaking of LinkedIn posts, check out what I shared earlier today about David-powered-by-Goliath vs Goliath. Agree or disagree?

As usual, I've got another huge edition for you today, so let's dive right in…

In this week's edition I cover:

Walmart's insane delivery speed
Netflix and Amazon's unlikely partnership
Gmail's new Purchases tab
The FTC cracks down on Google, Amazon, OpenAI, & Meta
OpenAI's $300B check to Oracle (please wait to cash it)
TransUnion's four consumer groups of 2025
Amazon's losing organic search rank on Google
Temu is cutting prices up to 60%
The new TikTok “deal”
California's AI transparency and age verification bills
Shopify's “AI loop hell”
Amazon Virtual Multipacks

All this and more in this week's 243rd Edition of Shopifreaks. Thanks for subscribing and sharing!

Stat of the Week

Walmart says its quickest delivery speed this year was under 5 minutes! On Walmart's most recent earnings call, CFO John Rainey said the company is now routinely delivering orders in less than 30 minutes. One-third of ship-from-store orders were fulfilled in three hours or less, and one-fifth reached customers in 30 minutes or less.

1. Netflix partners with Amazon to sell ads on its DSP

Amazon and Netflix entered into a partnership to allow advertisers to use Amazon DSP to buy ads on Netflix starting in the fourth quarter across 11 markets including the U.S., U.K., France, Spain, Mexico, Canada, Japan, Brazil, Italy, Germany, and Australia. The deal follows in the footsteps of similar partnerships between Amazon and Disney, HBO, Fox, and Peacock.

Amazon DSP is a demand-side platform that allows advertisers to buy display, video, and audio ads both on Amazon properties and across third-party apps and websites, competing directly with The Trade Desk, Google and other DSPs. Netflix also partners with The Trade Desk to sell its ad inventory, as well as Yahoo, Google, and Microsoft's ad-buying platforms.

Amazon has been building up its ad business in recent years, hitting a milestone in 2024 when it started running ads across all Prime Video programming (unless members paid more). In 2024, its total ad revenue climbed 20% YoY to $56.2B. Netflix does not disclose its ad revenue but said earlier this year that its ad-supported subscription tier had hit 94M monthly users.

Amy Reinhard, Netflix's President of Advertising, said:

“This partnership with Amazon perfectly aligns with our commitment of bringing advertisers even greater flexibility in their buys to achieve their marketing goals. By integrating Amazon DSP and enabling even more advanced capabilities together over time, we’re making it easier than ever to connect with Netflix's global engaged audience”

What Amazon brings to the table for Netflix is commerce and shopper data that The Trade Desk, Google, and others don’t have. Advertisers can use Amazon’s signals like purchase intent and actual buying behavior to better target and measure campaigns, making ads on Netflix more performance-driven — which is something that Netflix has been criticized for in the past (not having the tools to properly measure ad performance).

Netflix has also been criticized heavily in the past for its advertising being too expensive, but with Amazon currently discounting its fees on the sale of third-party inventory, the partnership could actually bring down the cost of Netflix ads (at least in the short term).

Personally, I'm always wary of getting into bed with Amazon — and I don't know why all of its streaming competitors think it's a good idea to do so. Disney, HBO, Fox, Peacock, and now Netflix are like frogs sitting in Amazon's boiling pot.

Yes, they get access to Amazon shopper data, but on the flip side, they're giving up control of their most valuable asset (ad inventory) to an aggressive and unscrupulous streaming competitor.

Yes, Amazon offers discounts on its DSP fees to advertisers who use it to buy third-party ad inventory, but that's a tactic straight out of the “Amazon Gets Market Share” playbook. Once they have that market share, that discount goes away and the fees go up.

Then again, maybe Amazon has turned a new leaf and is embracing the notion that there's more money in selling advertising than there is in producing original content, and won't eventually and inevitably screw the other streaming services over? LOL, I can barely type that with a straight face. They'll definitely find a way.

Lastly, there's poor old The Trade Desk, which may go down in history as the DSP that paved the way for competitors to do it better.

Earlier this month I criticized The Trade Desk's CEO Jeff Green for having his head in the sand regarding his comments on the company's August earnings call where he said:

“Amazon is not a competitor and Google really isn't much of a competitor anymore either. We're trying to buy the open internet, leveraging technology that values media objectively. We don't have any media, and we don't grade our own homework.”

Now that this news about an Amazon / Netflix partnership has broken… do you consider Amazon a competitor now, Mr. Green?

2. Gmail launches a dedicated tab to track your purchases

Gmail is making it easier to track your online orders with a new dedicated tab for Purchases coming to mobile and the web — adding to its existing Primary, Promotions, Social, Updates, and Forums tabs. The tab will allow users to access all their purchase-related emails in one place, including from past orders and shipments.

The new tab builds on Gmail’s mobile tracking tools, which flag packages arriving within 24 hours and display order cards with quick purchase details at the top of emails.

Other shopping related updates to Gmail include:

Adding a filter to its Promotions tab that lets you sort e-mails by “most relevant” — prioritizing brands you interact with most — while still allowing you to switch back to “most recent.”
Flagging timely deals within its Promotions tab so that they don't get buried in your Inbox.

Google says the new features will be especially helpful during the holidays and predicts that 39% of total planned holiday gift spending will happen this year in the five-day period between Thanksgiving and Cyber Monday.

These updates will start rolling out in the coming weeks to personal Gmail users.

If Google is open to making updates to Gmail, could they also:

Add the ability to highlight text, paste a link, and have it hyperlink said text.
Set a timed interval to refresh pop e-mail accounts.
Automatically remove walls of e-mail signatures from reply threads.

I won't hold my breath though. Google's criteria for making updates to Gmail is: “Does it help us sell more ads? [Yes, do it.] [No, fuck off.]”

3. The FTC cracks down on Google, Amazon, OpenAI, and Meta

The FTC launched multiple investigations into Big Tech over their advertising and AI chatbots.

First up… The FTC is investigating Amazon and Google over whether they misled advertisers regarding the pricing and terms of their auction-model ads.

Google sells ads using automated auctions that take place in a millisecond and run after a user enters a search query. The FTC is digging into Google's internal pricing process and whether it was increasing the cost of ads in ways that advertisers weren't aware of.
Amazon uses real-time auctions to place ads within their listings. The FTC is investigating whether Amazon disclosed its reserve pricing for some of its ads, which is a price floor that advertisers must meet before they can buy an ad.

The investigations add another regulatory battle for both Google and Amazon, each of which face federal antitrust cases that are going to trial on Sept. 22 — Amazon for allegedly enrolling customers in its Prime subscription service without their knowledge and Google over an earlier finding that it operates illegal monopolies in the digital advertising sector.

But wait, there's more… The FTC is also investigating tech companies over the safety risks posed by their AI chatbots to kids and teenagers. Amazon is not part of this investigation (which is strange because they're also building AI chatbots), but Google is, as is OpenAI, Meta, Snap, xAI, and Character.ai.

The agency submitted orders to the companies to provide information outlining how their tools are developed and monetized, how those tools generate responses to users, and what safety-testing measures are in place to protect underage users. (That'll be a short page.)

The orders were issued under section 6(b) of the FTC Act, which grants the agency authority to investigate businesses without a specific law enforcement purpose.

This feels necessary… In August I reported on an internal Meta document that was leaked to Reuters detailing policies on chatbot behavior that permitted the company's AI tools to “engage a child in conversations that are romantic or sensual” and other unscrupulous conversations. The rules of conduct were approved by Meta's legal, public policy, and engineering staff, including its chief ethicist.

I questioned at the time how the rules of ChatGPT, Gemini, Claude, Grok and AI chatbots differ from those of Meta. Apparently the FTC is wondering the same thing. In hindsight, this is the kind of transparency we should have demanded from AI companies before they started having sensual conversations with minors, not after, but better late than never.

4. OpenAI's writing $300 billion checks without any money in the bank

OpenAI signed a contract to purchase $300B in computing power over the next five years from Oracle, beginning in 2027, marking one of the largest cloud contracts ever signed.

Oracle shares surged as much as 43% on Wednesday after the company revealed it added $317B in future contract revenue during its latest quarter, briefly making Oracle Chairman Larry Ellison the richest man in the world, surpassing Elon Musk with a net worth of almost $400B.

The Oracle contract will require 4.5 gigawatts of power capacity, or the equivalent of electricity produced by more than two Hoover Dams, which could power roughly four million homes.

Are they sure OpenAI is good for the money?

OpenAI is currently unprofitable and disclosed in June that it was generating around $10B in annual revenue, less than one-fifth of the $60B it will have to pay Oracle annually. Last fall, Sam Altman told investors that OpenAI won't generate a profit until 2029, and expects to lose $44B before doing so. Is that in addition to the $300B deal it just made? So $344B in losses?

Meanwhile, Oracle will be concentrating a large portion of its future revenue on one customer and will likely have to take on debt to buy the AI chips needed to power its data centers. So it's a risky bet for them too.

The WSJ reports that compared with Microsoft, Amazon and Meta, Oracle has a far greater debt load relative to its cash holdings, and its spending is already outstripping its cash flow.

Microsoft has a debt-to-equity ratio of 32.7% versus Oracle's 427%.
Microsoft’s operating cash flow was about $136B last year, with capital expenditures including leases of $88B.
Oracle's operating cash flow was $21.5B, with $27.4B in capital expenditures.

Then again, it's not like there won't be other buyers if OpenAI can't deliver on their end of the bargain. Perhaps the contract was all that Oracle needed to secure the capital and kick off its data center development — which no-one would bet against as being a good investment during the next decade.

5. TransUnion identifies four distinct consumer groups in 2025

TransUnion unveiled a new segmentation analysis with four distinct consumer groups based on their ability to keep up with inflation, each with unique confidence levels, spending behaviors, and timing preferences, at its TruAudience Marketing Summit in Chicago.

Brian Silver, EVP of Global Marketing Solutions, said:

“Our research found that even among those who feel they are doing OK financially, there are vast differences in how they behave in the market. Consumers’ individual life stages, expectations, and environments help determine their spending as much as their income levels—which underscores just how important it is for marketers to really know their audiences and the numerous personas they present in market.”

The four segmentations include:

Stable Spenders – a marketer's premium audience. 70% are between 35 and 64 years old. Most are focused on upgrading their lifestyles. 87% are homeowners. 60% are married and 30% have children. They earn over $150k and participate in loyalty and rewards programs. They have concerns about inflation and the cost of insurance and groceries, but are least likely to pull back spending — still buying cars, traveling, and dining out.
Young Strivers – comprised of Gen Z and young Millennials, with more than half between 18 and 34. Mostly living in big cities and are focused on lifestyle and influence. They typically earn less than $50k per year, but aspire to achieve a high social status and live a lifestyle that impresses others. They are willing to spend on experiences and fashion, but 40% will wait for their tax refunds before asking significant purchases. They like flexible pricing, mobile-first experiences, and community-driven brands.
Purposeful Planners – these are tomorrow's Stable Spenders. Mostly younger families, with 75% between 25 and 44, and over 40% have children. They live in affordable markets, make between $75k and $150k, and are focused on their futures. They are tightening their belts, but less out of necessity and more about planning ahead.
Budgeting Realists – are not just pulling back on discretionary spending, but are opting out entirely. This group is primarily between 45 and 64, underemployed or unemployed, and are struggling to keep up. They are focused on the basics, and many rely on BNPL for staple purchases. They are focused on meeting their basic needs and have little to no discretionary spending, primarily looking for deals on basic items like clothing and food. This group is best reached with value-driven offers.

Marc Vermut, VP of TransUnion’s Marketing Solutions Knowledge Lab, said:

“Our analysis shows that consumer confidence and consumer action don’t always align. Many consumers who say they’re keeping up with inflation are still delaying purchases or relying on tax refunds. Understanding consumers’ priorities helps brands move past assumptions to effectively engage their customers.”

6. Amazon is losing organic search visibility on Google

Amazon has experienced a significant drop in organic search visibility on Google, according to new data from Audience Key, a content marketing platform that tracks and reports on Google’s organic product grid rankings at scale. The data shows that across 79,000+ keywords, Amazon has lost 31% of its organic product card rankings

Before July 25, Amazon appeared in 428,984 product cards
After July 25, Amazon appeared in 294,983 product cards
A 100% loss of U.S. coverage has been observed after ~August 16th.
Apparel had the steepest losses.
Home Goods, Laptop Computers, and Outdoor Furnishings also fell sharply.

The decline follows both the discontinuation of its paid Shopping ads and the consolidation of its three merchant store names — Amazon, Amazon.com, and Amazon.com Seller — into a single store identify called “Amazon.”

Three reasons why Amazon could be pulling out of organic product grids, according to the report:

Amazon’s choice: Amazon may have decided not to share feed data with Google.
Temporary change: A technical or strategic retooling — suggesting a return could be imminent.
Google’s response: A retaliatory move after Amazon quit Shopping Ads.

You can read the full report here.

I've been covering Amazon's departure from Google Shopping ads (and its subsequent return internationally) for the past couple months, but this is the first I've read about its decline in organic search rank.

Audience Key's report was published Aug 26th, but Amazon restarted spending on Google Shopping ads across its international domains at the start of September, according to SEJ ad Digiday. I asked Tom Rusling, Audience Key's founder if anything had changed since they originally published the report and if restarting Shopping ads has had any impact on Amazon's organic presence?

He replied:

“No nothing has changed in those three weeks. I will add that we have continued to track the results since that time in Amazon has continued to not be present thus far.”

7. Temu cuts prices in the U.S. up to 60% before the holidays

Temu is ramping up its discounts in the U.S. to win back customers after losing ground over tariffs. The platform slashed at least two dozen of its best-selling products by 18% on average compared to prices in late April, with some discounts as high as 60%.

Following President Trump's ban of the de minimis tariff exemption for Chinese goods in May (and subsequently for all countries in August), Temu largely pulled back from the U.S. market and shifted advertising efforts to Europe. Temu took steps to mitigate tariffs by expanding its U.S. warehouse operations, but inevitably prices rose across the board on its platform.

The big winner? Amazon!

Deutsche Bank analysts gave Amazon a price target hike from $230 to $266 in a July report, writing “Amazon has meaningfully expanded U.S. industry share as Temu has pulled back.”

Bloomberg data showed that Temu's U.S. sales dropped more than 30% during some weeks in June and continued to fall by more than 10% in July and August.

However Temu isn't ready to call it quits on its mission to let American consumers “shop like a billionaire.” With Q4 quickly approaching, the company hopes it can discount its way back into your shopping cart this holiday season.

Are you still shopping on Temu as much since the de minimis loophole ended? If not, can Temu win you back with this strategy? Hit reply and let me know.

8. BREAKING: The U.S. and China supposedly make a TikTok deal

China and the U.S. began a fresh round of trade talks in Madrid on Sunday, led by Vice Premier He Lifeng and Treasury Secretary Scott Bessent. The meetings focused on de-escalating tariffs, which are currently paused at 30% for U.S. goods and 10% for Chinese exports until Nov. 10, and resolving the standoff over TikTok, which faces a Sept. 17 deadline to find a non-Chinese buyer or be banned in the U.S.

UPDATE: As of this morning (Monday, Sep 15th), U.S. trade representative Jamieson Greer said that the two countries have struck a framework agreement on transferring TikTok to U.S.-controlled ownership.

U.S. Secretary of the Treasury Scott Bessent said the deal was coming but declined to reveal the commercial terms, only saying, “It’s between two private parties, but the commercial terms have been agreed upon.”

Bessent added that although a framework agreement has been reached, President Trump will have to finalize the deal with President Xi Jinping this Friday. He then temporarily removed his nose from up Trump's butt to say:

“President Trump played a role in this, we had a call with him last night, we had specific guidance from him we shared it with our Chinese counterparts. Without his leadership and the leverage he provides, we would not have been able to include the deal today.”

President Trump's third TikTok ban extension is supposed to end on Sep 17th, but with a deal “right around the corner” (again), I'd imagine that we'll hear news of Trump extending the deadline once again to allow for his talks with President Jinping this Friday. And if that conversation doesn't materialize into the actual sale of TikTok to a U.S. company, I guess the Chinese app will live to see another few months in the U.S. either way.

As you might be able to tell from my snarky commentary above, I'll believe there's a deal when I see it. Until then, it's just theater.

9. Other e-commerce news of interest

The California State Assembly approved SB 53, a bill mandating transparency reports from developers of powerful “frontier” AI models like ChatGPT, Gemini, Grok, and Claude, and sent it to Gov. Gavin Newsom to sign or veto. The bill requires companies with $500M+ in revenue training models at 10^26 FLOPS to publish safety frameworks, report “critical safety incidents” within 15 days, and provide whistleblower protections. Its focus is on “catastrophic risks” such as AI-assisted biological attacks or rogue systems causing large-scale damage, defined as events leading to 50+ deaths or $1B in losses. Some companies like Anthropic endorsed SB 53, but others like OpenAI argue that the compliance burden will stifle innovation. Newsom previously vetoed a similar measure (SB 1047) but commissioned a frontier AI working group whose recommendations informed this bill, making it likely that he will approve it.

In other California news… lawmakers passed AB 1043, a bill requiring device makers and app stores to verify user ages, with backing from Google, Meta, OpenAI, Snap, and Pinterest. Supporters say it avoids controversial photo ID uploads and instead uses parental input to group kids into age brackets, aiming to become a national model. The Motion Picture Association opposes it, warning of conflicts with existing streaming safety tools. Apple has remained silent on the issue. Now it's up to Gov. Newsom to decide by Oct. 13 whether to side with Silicon Valley or Hollywood.

TikTok released new data to showcase the impact of its search ad campaigns in anticipation of its Sep 17th deadline to sell to a U.S. owner or face a ban. The company reported a 40% YoY increase in searches, with campaigns that included dedicated search ads driving 2x higher purchase lift compared to non-search initiatives. For enterprise advertisers, the lift rose to 2.2x, and enterprise retailers saw a 1.9x lift. TikTok also cited WARC data showing 86% of Gen Z search on the platform weekly, nearly matching traditional search engines, with many users starting on TikTok before switching to Google. Impressive stuff, but TikTok's acting like that search traffic wouldn't quickly be absorbed by Google, ChatGPT, and Meta if the app were to get banned (which it likely won't).

At its Brand Building Summit, Meta unveiled AI-powered Reels trending ads that curate culturally relevant short-form video inventory across its apps, with early tests showing a 20% lift in unaided awareness compared to TikTok Pulse by 6%. On Threads, the company is testing 4:5 image and video ads, carousel ads, and Advantage+ catalog and app campaigns, while also allowing advertisers to run Threads ads without a Threads profile by using Instagram or Facebook accounts. Meta also launched “value rules,” letting advertisers guide its AI to prioritize high-value audiences, which it says doubled high-value conversions in tests.

Shopify is taking heat for its AI customer service chatbots creating an endless loop that prevents merchants from accessing human assistance. A merchant documented an incident on the r/shopify subreddit where he attempted over 20 times to reach human support through multiple AI interfaces that repeatedly directed him back to chatbots, despite acknowledging their inability to solve the problem, in an experience that he called “AI loop hell.” The incident was not one-off and many merchants shared similar experiences. One user wrote, “Customers who pay $299+ per month should get straight through to a human. What else are we paying for?”

Amazon is rolling out a new feature called Virtual Multipacks, allowing sellers to list 2-packs, 4-packs, etc of the same ASIN without physically bundling the inventory together, which is previously what selling bundles required on the platform. Amazon then fulfills the orders using the seller's existing single-pack FBA inventory, however, each multipack gets its own ASIN+SKU and shows up as a variation on the single-pack listing. The change could help increase AOV for sellers, while allowing them to test which multipacks convert before investing in hard bundles. The program is currently managed by Amazon, which means sellers can't create them on their own, but they can opt-out if Amazon makes one for them (though there would be little reason to do so).

Amazon is building two AR glasses products, one for delivery workers and another for consumers, in a direct challenge to Meta’s efforts in the space. The worker-focused version, codenamed Amelia, is designed to help drivers sort and deliver packages with on-screen instructions and could launch as early as Q2 2026 with about 100,000 units, while the consumer model, codenamed Jayhawk, may arrive in late 2026 or early 2027 with a microphone, speakers, camera, and a full-color display in one eye. Both versions use display technology from Chinese firm Meta-Bounds, also used by companies like Meizu.

Reddit is removing the member count metric on subreddits and replacing it with one metric that shows how many users have visited the subreddit in the past seven days and another that displays how many contributions have been made in the past seven days. The change aims to provide a better idea of how active and engaged a subreddit actually is, while also serving to limit how many busy subreddits a particular moderator can oversee, soon restricting them to a maximum of five communities with over 100k visitors.

Reddit also released a new feature that allows users to open article links directly within the Reddit app, with Reddit comments from other users pinned to the bottom. Reddit says it plans to respect publisher paywalls, while offering publications the ability to share unlocked gift links or soften their paywalls for users. On the backend, publishers will be given access to analytics tools that let them track which subreddits are sharing their stories and how many upvotes and clicks they received.

Uber Eats is partnering with Pipe to use the fintech's technology to offer pre-approved revenue-based loans for small businesses that sell through the app. Everyone's got to be a lender! The process is designed to lower barriers to entry by pre-approving offers based on the businesses' revenue and cash flow, and since paying back the loans is based on the restaurant's revenue as opposed to a fixed monthly amount, the payments reduce if sales decrease during a slow season or due to other factors.

eBay rolled out a new “magical” AI tool in Seller Hub to generate Store banner images, but sellers report that it produces irrelevant or generic pictures with no way to edit, prompt, or add text. Major categories like Motors Parts & Accessories are missing entirely, while other categories return repetitive or nonsensical results like snowflakes for Jewelry & Watches or abstract shapes for Sports Memorabilia. Some sellers say the feature is another example of eBay hyping AI tools that fail to solve real problems, echoing similar frustrations with its Magical Listing and Social Sharing AI features.

RSL Collective released Really Simple Licensing, an open, decentralized protocol that informs AI crawlers and agents the terms for licensing, usage, and compensation of any content used to train AI. Behind the project are Doug Leeds, former CEO of Ask.com, and Eckart Walther, a former Yahoo VP of products and co-creator of the RSS standard, which made it easy to syndicate content across the web. RSL terms can be applied to protect any digital content including websites, books, videos, and datasets and supports a range of licensing, usage, and royalty models including free, attribution, subscription, pay-per-crawl, and pay-per-inference, which is when publishers get compensated every time an AI applications uses their content to generate a response. The group says that the RSL standard doesn't just benefit publishers, but also solves a problem for AI companies, which have complained during litigation that there is no effective way to license content across the web (like they even fucking tried).

UPS and FedEx released announcements about their Peak Season and early 2026 rate changes. UPS will institute peak season shipping fees from Oct 5th through Jan 18th including a $2 surcharge for all outbound packages that weigh more than 10 pounds, are destined for a Zone 9 location, or exceed 22″ in length or two cubic feet. FedEx is implementing peak surcharges that go up in price as the holidays get closer, as well as raising rates across the board an average of 5.9%. Time to up your free shipping tier!

Roku CFO Dan Jedda said the company aims to expand from the “top 200 advertisers” to over 100,000 by using generative AI to let small and local businesses quickly and easily create commercials. With Roku devices now in over half of U.S. broadband households and the Roku Channel growing 80% YoY, the company says it has more ad inventory than it can sell and is building generative AI-powered self-serve tools to help car dealerships, restaurants, and other small businesses shift budgets from search and social into connected TV, with Roku betting AI will enable “well-produced” TV spots in minutes. Very smart move on Roku's part. Once the tool is available, I'm 100% going to buy a local commercial featuring me waving hello to my parents in Waynesville, NC.

Instacart CEO Chris Rogers said at the Goldman Sachs Communacopia & Technology Conference on Wednesday that Amazon’s expansion of same-day perishables to 1,000 cities actually benefited his company by driving retailers to seek deeper partnerships with Instacart to stay competitive. Rogers noted that Instacart is using the “opportunity to get deeper, to use our technology in more ways to help retailers compete” and that Amazon's new delivery efforts haven't eaten into its business. He shared that in three markets where Amazon tested its new delivery offerings, Instacart's gross transaction value stayed in line with its results in the rest of the U.S.

Meta signed a multi-year contract worth more than $100M to use technology from Black Forest Labs, an AI image startup founded a year ago by several computer scientists involved in creating the AI image generator Stable Diffusion, according to Bloomberg sources. Last year Elon Musk's Grok leaned on Black Forest Labs to roll out an image generation feature that produced a mix of viral and controversial content. Black Forest Labs was generating $96.3M in ARR as of August and has also signed partnerships with Adobe, Canva, and Snap.

Microsoft is planning to integrate Anthropic’s Claude models into Office 365 Copilot, marking its biggest step away from exclusive reliance on OpenAI, according to The Information sources. Internal testing showed Anthropic outperforming OpenAI at spreadsheet automation and PowerPoint generation, leading Microsoft to split workloads between the two providers. The move comes amidst a monthslong negotiation between Microsoft and OpenAI over the OpenAI's plans to restructure its for-profit division so that it can eventually go public, and despite Microsoft having to pay AWS to access Anthropic's models, unlike its free usage rights with OpenAI. Smart move to not have all your eggs in OpenAI's basket, even if it's costly in the short term. Office 365 Copilot already has more than 100M users, and analysts estimate it is generating over $1B annually.

Amazon has officially entered the U.S. robotaxi market five years after its $1.3B acquisition of Zoox with the launch of a small fleet on the Las Vegas strip. I saw them driving around last week when I was at the Cocreate conference in Vegas! Several of my Uber drivers also brought them up in conversation (perhaps they felt a bit threatened). Currently the company is offering free rides while it waits on regulatory approval to begin charging customers, which should be soon. Next up, Zoox plans to debut an early rider program in San Francisco before the end of the year.

Opendoor named former Shopify COO Kaz Nejatian as CEO with an aggressive pay package that could reach $2.78B if he drives the stock as high as $33, giving him nearly 12% ownership of the company. The move, which caused Opendoor's stock to surge 80%, comes as co-founder Eric Wu and Khosla Ventures’ Keith Rabois return to the board with $40M in fresh funding, with the company saying it is “going into founder mode” to reset its leadership and strategy. Rabois later told CNBC that he needs to slash the company's 1,400 person workforce as much as 85% to fix its cost structure.

In other corporate turnover this week… Kinsta named Jon Penland as its CEO. Wayvia appointed Theresa Pham as Head of Product. Marqeta named Mike Milotich as its permanent CEO, following a seven-month search. alentr appointed Meghan Stabler as co-founder and CMO. Claimit added Bart Swanson to its board as a strategic advisor.

Amazon fired more than 150 unionized drivers working for Cornucopia, a third-party contractor in Queens, New York, according to the Teamsters union, who claim that the firings were in retaliation for unionizing. Workers rallied at the company’s DBK4 facility in Queens on Monday to protest what they say are “illegal firings.” Wait a second… How does Amazon have the right to fire drivers that work for one of their delivery services providers? Wouldn't Amazon have to fire the entire DSP in order to part ways with its employees? You'd think so, right? However the relationship between Amazon, its DSPs, and its drivers is ever-so-blurry and apparently Amazon gets to not only dictate routes, performance, and branding requirements of its partners, but it can also fire their employees too.

Microsoft is mandating that employees return to office at least three days a week, beginning in February 2026 for staff within 50 miles of its Seattle headquarters, before expanding to other U.S. offices and then internationally. Exceptions can be requested by September 19, though details remain unclear regarding which ones will be granted. The move aligns Microsoft with Meta and Google’s RTO policies and follows a year of performance pressure, including layoffs of low performers and stricter improvement plans.

Block won dismissal of a class action lawsuit alleging it misled investors about a 2021 Cash App data breach that exposed information from 8.2M users. Shareholders claimed the company inflated its stock price by hiding security flaws and delaying disclosure until April 2022, and also misled Afterpay investors during its $29B acquisition. A judge ruled there was no proof Block intended to defraud or that executives benefited, saying general risk statements weren’t assurances of strong security. Earlier this year, Block settled separate compliance cases for $80M with 48 state regulators and $40M with New York over Cash App’s anti-money laundering controls.

Mexico’s antitrust watchdog Cofece found that Amazon and MercadoLibre hinder competition by withholding details on how featured products are chosen and by favoring sellers that use their logistics services. The probe confirmed the practices, but the agency has not yet imposed corrective measures, citing uncertainty over whether its proposed remedies would benefit consumers and small businesses. The two marketplaces account for more than 85% of Mexico’s e-commerce sales. In a separate investigation, Cofece found that 21 banks and financial institutions operating in the country are likely responsible for fixing fees related to deferred credit card payments, and that there is sufficient evidence to presume the parties may have engaged in anti-competitive conduct, such as meeting regularly to set surcharges for merchants and excluding some merchants from the market. The banks have been notified of the findings and can now present evidence and arguments in their defense before the watchdog's issues a final resolution.

Coupang, the South Korean e-commerce company often called the “Amazon of South Korea,” won dismissal of a shareholder lawsuit alleging fraud tied to its 2021 IPO, with a U.S. judge ruling that investors failed to show intent to deceive or prove misleading statements. The case, led by New York City pension funds, claimed Coupang concealed unsafe warehouse conditions, manipulated search results, and coerced suppliers, but the court said the allegations were too broad, disclosed, or amounted to puffery. All claims against IPO underwriters including Goldman Sachs and JPMorgan were also dismissed with prejudice.

French lawmakers asked the state prosecutor for a criminal investigation into whether TikTok was responsible for “endangering the lives” of its young users. However that's not slowing down TikTok in Europe, which just officially launched the next stage of its European data separation project, with construction now underway in Kouvola, Finland. TikTok also reports that its added 5M more active users in Europe compared to this time last year, and that it now boasts 200M monthly active users in the region.

🏆 This week's most ridiculous story… Flip, a TikTok rival video app, rose to the top of charts in January when it looked like TikTok might get banned. However the climate soon changed, and Flip was left out in the cold. The app, which raised over $230M in funding over four years and reached a $1.1B valuation, apparently blew through its capital, because 16 months after its most recent $144M Series C round, it abruptly shut down. When President Trump halted the TikTok ban, the company poured money into ads and launched a $100M equity fund to attract creators, but with TikTok back in action, the app's buzz fizzled out quickly — and even blowing its wad on creators and ads couldn't save it. The worst part of this story is for the owners of Curated, a platform that connected shoppers with experts for advice on big purchases, which Flip acquired for $330M in, uh oh, stock. Read the full story on Business Insider.

10. Seed rounds, IPOs, & acquisitions

Klarna held its long-awaited IPO on the NYSE on Wednesday, with the stock opening at $52/share, marking a 30% premium to the company's $40 pricing. Shares rose as high as $57 before losing momentum and ended the day at $45.82, up 14.6%. Overall more than 34M shares worth approximately $1.37B were sold to investors, making it the largest IPO of the year. Big winners from the IPO include Klarna's CEO and co-founder Sebastian Siemiatkowski ($1.1B), co-founder Victor Jacobsson who left the company in 2012 ($1.3B), and Sequoia Capital ($3.15B). Klarna is now the second-largest BNPL company by market capitalization behind Affirm, which is valued around $28B.

Amazon invested a $25M convertible note in Rappi, a Colombian grocery and restaurant delivery service, in a deal that allows Amazon to buy as much as 12% of the company if certain milestones are met, according to an anonymous Bloomberg source. Amazon often uses warrants to make direct investments in partners so it can increase its gains if its business helps grow the partner's sales. Currently Rappi is a customer of AWS and has a partnership in which Amazon offers Prime members in Mexico a year of free shipping through the delivery service. Gaining access to Rappi's logistics network could be a long term play at helping Amazon compete with MercadoLibre in the region.

TwinMind, an AI-powered app started by former Google X scientists that listens to everything you say to create notes, to do lists, and answers, raised $5.7M in a seed round led by Streamlined Ventures at a $60M valuation. The app aims to position itself as an AI “second brain” for its 30,000 users, passively capturing conversations throughout the day, transcribing the speech in real time, and generating notes, all while running continuously offline without draining the battery. To complement its app, TwinMind recently launched a Chrome extension that scans browser activity for added context and a new Ear-3 speech model supporting 140+ languages.

SpaceX struck a $17B deal to acquire a massive block of wireless spectrum from EchoStar, paying half in cash and half in stock, to power its Starlink direct-to-cell service. The move makes SpaceX a license holder rather than a partner dependent on carriers, and SpaceX has already partnered with T-Mobile to extend coverage via Starlink. The deal also positions SpaceX in competition with Apple’s Globalstar-backed iPhone satellite services, raising speculation that Musk could leverage spectrum ownership to push for cooperation or even revive his idea of building an X-branded phone.

Vimeo, a video hosting and streaming platform that launched in 2004, entered into a definitive agreement to be acquired by Bending Spoons, an Italian tech company that develops and acquires mobile apps and digital platforms including Evernote, WeTransfer, and Meetup, in an all-cash deal valued at $1.38B. Bending Spoons CEO and co-founder Luca Ferrari (awesome name) said the company intends to make “ambitious” investments in Vimeo to both its creator and enterprise offerings, aiming to become “the most innovative and trusted video platform in the world for business.”

Dazl, an AI platform that helps turn prototypes into production-ready applications founded by Wix co-founder Nadav Abrahami and former global head of gaming at TikTok Assaf Sagy, raised $10M in a seed round led by 40RTY Fund alongside investments from Wix and Abrahami himself. Dazl's technology aims to bridge the current gap between creating app concepts and launch-ready products by interpreting user prompts more accurately, reducing errors, and minimizing the trial-and-error cycles that have hindered other tools. The startup's development began inside Wix but is now moving forward independently with about 30 Wix employees joining the venture.

Speaking of Wix…the company added $1B to its cash reserves following the completion of a fundraising round through the issuance of convertible senior notes, upsized from the previously announced $750M offering. The zero-interest notes will mature in September 2030 and are convertible at an initial price of $210.49 per share, representing a 37.5% premium over Wix's Sep 8th closing price. The fundraising has fueled speculation about a merger with Fiverr, which is set to move into Wix's campus next year.

AegisAI, a cybersecurity startup founded by former Google Safe Browsing and reCAPTCHA leaders that uses autonomous AI agents to block phishing, malware, and business email compromise attacks before they reach inboxes, raised $13M in a seed round led by Accel and Foundation Capital. The startup's software integrates with Microsoft365 and Google Workspace and claims up to 90% fewer false positives than traditional tools at blocking bad actors by using real-time AI agents to analyze links, attachments, metadata, and behavioral patterns without relying on static rules. AegisAI is currently running a pilot with customers in the U.S. and Europe and plans to use the funds to build its go-to-market infrastructure.

Float, a South African fintech that offers BNPL services by splitting purchases into interest-free installments using existing credit cards, raised $2.6M in a round co-led by Invenfin and SAAD Investment Holdings. The platform already serves over 2,000 stores, with merchants reporting 130% higher order values. Float plans to use the funding to scale local operations, strengthen its technology, and prepare for international expansion.

Giorgio Armani could soon be sold or become a publicly listed company, according to the late founder’s will. Armani, who died last week at the age of 91, instructed his heirs to sell 15% of the business within 18 months and up to an additional 54.9% of the company to the same buyer within five years, with priority given to LVMH, L'Oreal, or EssilorLuxottica, or alternatively pursue an IPO. Armani was the sole shareholder in the company, under the control of his foundation, which would retain a 30% share in the company moving forward to act “as a permanent guarantor of compliance with the founding principles.” Armani has no children and his heirs are considered to be his sister, nieces and nephew, and his partner Leo Dell’Orco.

SoundHound AI, a voice AI company that develops speech recognition and natural language understanding solutions, acquired Interactions, a startup that provides AI for customer service and workflow orchestration, for an undisclosed amount. The deal aims to strengthen and extend SoundHound's agentic AI market share and accelerate its market penetration in customer service across enterprise businesses by introducing new Fortune 100 brands to its customer portfolio.

Aiwyn, a software company that provides AI-powered practice management and billing solutions for accounting firms, acquired QuickFee's U.S. payments businesses, including QuickFee Pay Now and QuickFee Connect, for $26.35M. The acquisition strengthens Aiwyn’s payments and collections platform while maintaining access for customers to QuickFee’s Pay Later financing through a new reseller partnership. QuickFee will continue to operate its U.S. Finance business independently, retaining its loan book and team. The move follows Aiwyn’s $113M funding round last December and recent acquisitions of Taxa and Diligence.

StubHub, an online ticket marketplace for sports, concerts, theater, and live events, is seeking to raise up to $851M in its IPO by offering 34M shares at $22–$25 each, targeting a $9.2B valuation. Trading on the NYSE under the ticker STUB is set to begin after strong demand, with over 20 times more orders than available shares. The company had delayed its listing in April amid tariff-driven market volatility.

MySize, Inc, an Israeli tech company that develops AI-driven measurement solutions for e-commerce, logistics, and apparel to improve sizing accuracy and reduce returns, acquired ShoeSize.Me, a Swiss startup that provides AI-powered shoe sizing and fit recommendation technology to help footwear retailers reduce returns and improve customer experience, with 241,093 newly issued shares of common stock and a cash payment of $150k. The deal strengthens MySize’s consolidation strategy by combining ShoeSize.Me with its Naiz Fit apparel solution. ShoeSize.Me’s ShoeAI platform, which has analyzed more than 92M consumer transactions and 1.2M shoe models, is expected to generate over €500,000 in SaaS revenue by 2025.

SupplyOne, a North American distributor of custom corrugated and value-added packaging, acquired Vital Pack, a California–based distributor specializing in flexible packaging, corrugated products, and custom labels, marking the company's 44th acquisition since its founding 27 years ago. The deal strengthens SupplyOne's Western U.S. presence and enhances its flexible packaging and label printing capabilities.

dlivrd, a Pennsylvania-based last-mile logistics company that provides contract delivery drivers for restaurants, catering companies, and marketplaces, acquired Omnicart’s proprietary platform to unify order management, dispatch, and delivery tracking for high-value off-premise restaurant orders. The deal pairs dlivrd’s delivery network with Omnicart’s tech to improve speed, oversight, and execution for strict prep and delivery windows. Omnicart will continue independently as Omnirev, focusing on an AI-driven CRM for restaurants, while dlivrd deploys the platform to partners. Rollout starts with select partners this year, with nationwide availability targeted for late 2025. Two weeks ago I reported that dlivrd acquired Vanuse, a London-based on-demand delivery platform that connects businesses with local van drivers.

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Paul E. Drecksler
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