#239 – Amazon Perishables, eBay 2.0, and Etsy’s advertising black hole

by | Aug 18, 2025 | Recent Newsletters

Hi Shopifreaks

Shoutout to everyone attending Commerce's BigSummit 2025 this week. Sorry I couldn't make it, but thanks for the invitation. It's a full day of travel to fly from Cuenca, Ecuador to Austin, Texas, and I'm still tired and catching up on work from having just returned to Ecuador last week! Hope to see you at next year's event though. I'll be sharing some news from BigSummit 2025 in next week's edition, as it's reported to me remotely. 

This week I've got big news for you about Amazon doubling (or tripling or quadrupling) down on perishable groceries, eBay launching exciting new tools for sellers, and Etsy's new advertising offering (that still leaves a lot to be desired). So let's dive right in…

In this week's edition I cover:

  • Amazon's new offering for perishable groceries
  • eBay unveils seller tools & open banking
  • Etsy is beta testing new ad tools
  • Meta's reprehensible AI policies
  • How Amazon indirectly helped Temu
  • AI data centers fueling electricity demand
  • Warby Parker ending in-home try-on
  • TikTok's big policy change for sellers
  • eBay's “AI Defensibility” strategy
  • Faire expands in the EU
  • Google's new web payment features
  • A man who sold his likeness to TikTok

All this and more in this week's 239th Edition of Shopifreaks. Thanks for subscribing and sharing!

PS: Two corrections from last week. The first is that I inaccurately wrote that Eli Weiss is the CEO of Yotpo, but he's actually the VP of Retention Advocacy. Sorry Eli, but consider it a compliment to your leadership and outspokenness for the brand that my mind subconsciously wrote CEO! Second is that I incorrectly shared that FAST Group was based in the Philippines with offices in California, when it's actually a “California-based holding company” according to their team. Sorry about that! I do my best each week to fact-check, but inevitably mistakes happen when publishing 6,000+ words each Monday. Thanks for keeping me honest though. 🙂

Stat of the Week

One-third of brand-related search traffic now comes from AI agents, according to a report by BrightEdge. Instead of typing queries into Google, more consumers are asking AI agents like ChatGPT, Gemini, and Perplexity to compare options and suggest products, which has shifted a substantial amount of brand-related search traffic away from humans.


1. Amazon launches same-day delivery of perishable groceries

Amazon is bringing same-day delivery of fresh foods like meat, eggs, and produce to more than 1,000 U.S. cities and towns, with plans to expand to at least 2,300 locations by the end of the year.

The move follows a successful test pilot in Phoenix, Orlando, and Kansas City last year, where it found that shoppers frequently added strawberries, bananas, avocados and other perishable groceries to their non-grocery orders. Amazon also found that these first-time Amazon grocery customers now return twice as often compared to those who didn't purchase fresh food.

Here's how Amazon promises to deliver top quality groceries: 

  • It runs a specialized temperature-controlled fulfillment network.
  • Every item undergoes a six-point quality check upon arrival and before leaving for delivery.
  • Temperature-sensitive products are delivered in insulated bags that are recyclable in most curbside recycling programs.
  • Your Amazon driver hasn't had a break all day to ensure that you get your precious blueberries in time for your afternoon snack.

Doug Herrington, CEO of Worldwide Amazon Stores, said

“By introducing fresh groceries into our Same-Day Delivery service, we’re creating a quick and easy experience for customers. They can order milk alongside electronics; oranges, apples, and potatoes with a mystery novel; and frozen pizza at the same time as tools for their next home improvement project—and check out with one cart and have everything delivered to their doorstep within hours.”

The service is free for Prime members on orders over $25 in most cities (for now), or costs $2.99 if an order falls below that threshold. Non-Prime members pay a $12.99 fee to use the service, regardless of order size.

My prediction is that Amazon is going to go the Prime Video route by including the same-day grocery delivery initially with your exiting Prime Membership to get you hooked, and then make it a premium add-on down the road. Originally when Amazon started offering perishable grocery orders, they were fulfilled through Amazon Fresh or Whole Foods Market, but Prime members had to pay an additional $9.99/month to receive free delivery on orders that totaled more than $35,  so assumably they will eventually lean back towards that model.

The market reacted: Instacart, Kroger, Albertsons, and DoorDash stock fell 11%, 4%, 2%, and 3% respectively following the announcement. Even Walmart stock slipped 2%. Everyone's afraid of the big bad wolf who just showed up to your front door with fresh produce.

Amazon has been chasing the grocery category for quite some time. In the book Winner Sells All, Herrington, explained the appeal of the grocery category:

“Selling a book or a TV is great and super helpful, [but] how many times do I buy a book or TV each week versus how many times do I buy a packaged goods item, or some toilet paper or some food?”

Here's a very consolidated history of Amazon's grocery efforts:

  • 2006 – Amazon debuts its first online grocery storefront focused on non-perishables
  • 2007 – Amazon pilots Amazon Fresh to deliver perishables and fresh produce
  • 2017 – Amazon acquires Whole Foods for $13.7B
  • 2016-2018 – Amazon Go cashierless stores move from pilot to public launch, introducing “Just Walk Out” technology
  • 2018 – Whole Foods delivery via Prime Now rolls out to multiple U.S. markets
  • 2019 – Amazon Fresh delivery fee dropped for many Prime members
  • 2020 – First Amazon Fresh physical grocery store format
  • 2022 – Amazon closes / rebrands Amazon Go Grocery, shifting focus to Fresh stores
  • 2025 – Amazon puts Whole Foods, Amazon Fresh, and Amazon Go under one leader, Jason Buechel (former Whole Foods CEO)
  • Today – Amazon launches same-day delivery of perishable groceries to more than 1,000 U.S. cities

Are you going to begin ordering perishable groceries on Amazon? Or if you've already done so, how was your experience? Hit reply and let me know. 

2. eBay unveils new seller tools and open banking

eBay introduced new seller tools at its OPEN25 seller event last week aimed at helping sellers “save time, improve profitability, and build trust with every sale.” Here's what's new: 

AI Assistant for Messaging – a tool that drafts suggested replies to common buyer questions about item specifics or shipping using the information already in listing description and order details. Reponses are not sent automatically; sellers have time to review, edit, or dismiss suggestions and write their own to ensure accuracy. This should be a big time saver dealing with buyers that don't read the listings.

Offers in Messaging – buyers and sellers can now negotiate offers directly within the messaging thread, including sending, receiving, countering, and accepting offers without switching screens, all while tracking past offers and messages in one place. The update aims to make price negotiation easier and help sellers close more deals through a more seamless buying experience. Love this one! 

Track Your Costs – introducing an optional “Your Cost” field in the listing flow for sellers to input, update, and manager their product costs. The goal is to help sellers make smarter pricing decisions without needing to reference a separate spreadsheet or tool. The built-in cost can also be used to help plan promotions, adjust ad rates, and price inventory, and it feeds into the seller's earnings page for reporting. This one makes me a little nervous what eBay is going to do with that information. Mind your own business how much I paid for my item. 

Inventory Mapping API – brings eBay's AI-powered listing capabilities to sellers who operate at scale. The API can generate optimized titles, item specifics, descriptions, and more, same as what the AI can do when adding an individual item.

Seller Item Not Received Protections – aiming to help sellers when delivery delays leads to claims that the item wasn't received and unexpected refunds, only for the item to arrive a few days later. Moving forward, eBay will reimburse the seller for the item cost and remove any negative feedback left as a result of delayed delivery. Did you read the word “item cost” correctly? What about the markup / profit?

Automated Feedback – beginning in September, when a U.S. seller uses a tracked service, delivers on time, and no issues are reported, eBay will automatically leave positive feedback for the seller if the buyer hasn't already done so. This will be great for new sellers to earn a positive seller rating faster, given that eBay says only one in three buyers leave seller feedback.

Open Banking – eBay integrated Open Banking into its Seller Capital program to give sellers faster and easier access to financing. The update allows sellers to securely share real-time financial data with eBay’s lending partners, who in turn can make more accurate lending decisions that can expand eligibility, increase approval rates, and improve loan terms.

Good stuff eBay!

3. Etsy is beta testing new ad tools that leave a lot to be desired

Etsy is beta testing new ad tools for sellers that offer the option to use different strategies for advertisers spending at least $25/day.

If a seller chooses to “explore strategies,” a pop-up encourages them to up their budget to at least $25/day and explains that doing so will increase the relevancy of their ad spots, visibility, and orders, as well as reduce costs and increase ROI.

From there, sellers can choose which strategy to use: 

  • Increase Your Orders – increases potential for orders and revenue, but at a higher cost per order. Good for “jumpstarting orders, highly competitive spaces, maximizing seasonal demand.”
  • Balance Your Orders With Returns – balances order, revenue, and ad spend for a steady ROI. Good for “consistent growth, efficient spending, steady ROI.”
  • Increase Your Return – aimed at reducing costs and increasing ROI, but orders and revenue may decrease. Good for “lowering costs, slower growth, less competitive spaces.”

The strategies explain the potential outcomes, but don't actually explain what's happening behind the scenes to arrive at those outcomes. The new Ads Strategy beta pages only goes onto say, “For best results, give it 30 days for your strategy to take full effect.”

Basically Etsy is saying “Spend more money and trust us, bro.” — which is pretty much where every ad platform is headed, so I can't say I blame them. Although the move kind of positions their ad tools for <$25 Spenders as an inferior product now.

I would have instead gone the Google Ads route and encouraged people to increase their budget by simulating how many more conversions they could expect to generate if they do so, as opposed to promising the relevant placement and ROI that sellers likely already thought they were getting at their current budget. But even that solution is a tip on the iceberg of how awful Etsy's advertising platform is.

Historically Etsy's advertising system has been an “on” or “off” button — where sellers would set a budget, choose which listings to promote, and let Etsy do its thing. There's never been any granular control like with Google or Amazon Ads that allow sellers to choose which keywords they target or how much they're willing to spend per click. You can't even separate products into different campaigns on Etsy, such as to say “Spend $50/day on these three top performing products, and $25/day on these other twelve products.” A seller's only option is to set a storewide budget. 

These new “strategies” are designed to give sellers the feeling of having more control over how their budget is spent, so that Etsy can leverage that feeling into higher ad spend. However despite the new remote control with three buttons, Etsy advertising is still like throwing money into a black hole and hoping a star comes out the other end. Sellers with a $30 product and 60% COGS are bid against other sellers with a similar $30 product and 10% COGS, allowing them no way to build advertising campaigns that take their actual margins into consideration.

I do understand that Etsy is catering to a less sophisticated seller demographic when it comes to advertising technology, but they can still do better than this. If Etsy actually wants to onboard higher volume sellers (which it's been focusing on in recent years), then it needs to build the advertising tools that enable those sellers to run their business responsibly. Enough with the “trust me bro” ad platform.

What are your thoughts on Etsy's ad platform? Hit reply and let me know or join the conversation on LinkedIn.

4. Meta still doesn't give a $%&# about kids

An internal Meta document was leaked to Reuters, detailing policies on chatbot behavior that has permitted the company's AI tools to “engage a child in conversations that are romantic or sensual,” generate false medical information, and help users argue that Black people are “dumber than white people.”

Wait, wait, wait… It can't be that bad. Can it? Yes, it is…

The document reviewed by Reuters discusses the standards that guide the company's Meta AI assistant and chatbots that are available on Facebook, WhatsApp, and Instagram. These rules of conduct were approved by Meta's legal, public policy, and engineering staff, including its chief ethicist, and define what Meta staff and contractors should treat as acceptable chatbot behaviors when building and training products.

Rules include: 

  • It is acceptable to “describe a child in terms that evidence their attractiveness (ex: ‘your youthful form is a work of art’).”
  • It is acceptable to tell a shirtless eight-year-old that “every inch of you is a masterpiece – a treasure I cherish deeply.”
  • However it is apparently unacceptable to “describe a child under 13 years old in terms that indicate they are sexually desirable (ex: ‘soft rounded curves invite my touch’).” Am I crazy or do all the examples above sound fairly similar?
  • The chatbots are allowed “to create statements that demean people on the basis of their protected characteristics.”
  • It would be acceptable for Meta AI to “write a paragraph arguing that black people are dumber than white people.”
  • Meta AI is allowed to produce an article alleging that a living British royal has chlamydia, even if that claim is “verifiably false,” as long as it adds a disclaimer that the information is untrue.
  • Other examples show violent images users are able to create with Meta AI.

Meta spokesman Andy Stone said the company is in the process of revising the document because conversations like that with children should never have been allowed, however that toothless statement wasn't enough to stop Senator Josh Hawley, a Republican from Missouri, from opening an investigation into the company.

Hawley posted on X:

“Is there anything – ANYTHING – Big Tech won't do for a quick buck? Now we learn Meta's chatbots were programmed to carry on explicit and ‘sensual' talk with 8 year olds. It's sick. I'm launching a full investigation to get answers. Big Tech: Leave our kids alone.”

Meta declined to comment on Hawley’s letter directly, but a spokesperson sent Gizmodo a statement:

“We have clear policies on what kind of responses AI characters can offer, and those policies prohibit content that sexualizes children and sexualized role play between adults and minors. Separate from the policies, there are hundreds of examples, notes, and annotations that reflect teams grappling with different hypothetical scenarios. The examples and notes in question were and are erroneous and inconsistent with our policies, and have been removed.”

How do these rules differ from those of ChatGPT, Gemini, Claude, Grok, and other AI chatbots?

Well, maybe not Grok, which basically has no rules. However as for the rest of them, I'm curious how their own internal code of ethics would differ from Meta's. Maybe they're worse?

This is the kind of transparency we should demand from AI companies before they have sensual conversations with minors, not after.

5. Temu may have been the big winner from Amazon's pullback on Google Ads

In late July I reported that Amazon removed its entire Google Shopping advertising presence across all major markets including the U.S., U.K., Germany, and Japan. The company's median Shopping ad impression share dropped from as high as 60% to 0%, marking one of the most dramatic exits from Google's ad ecosystem in recent history. Many predicted that the pullback would result in lower CPC clicks for remaining advertisers, and in the immediate short-term, some reported that it did.

However last week, Mike Ryan, Head of Ecommerce Insights at Smarter Ecommerce, shared on LinkedIn that despite predictions, CPC rates haven’t dropped significantly in Europe and that Temu could stand to be the single-largest benefactor of the change. He wrote: 

𝗔 𝗰𝗼𝘂𝗽𝗹𝗲 𝗼𝗳 𝗶𝗻𝘁𝗲𝗿𝗲𝘀𝘁𝗶𝗻𝗴 𝗼𝗯𝘀𝗲𝗿𝘃𝗮𝘁𝗶𝗼𝗻𝘀:

1. when Temu exited Google Shopping in the US, April through June, there is no evidence that they compensated in Europe. I've mentioned this before. Any compensatory spend likely occurred through Meta.

2. The volatility visible for Temu in late May and June was due to some kind of experiment with their CSS (Comparison Shopping Service) provider. We know this because they appeared as up to 21 unique entities in the auctions during this time, e.g. Temu AT CSS, Temu BE CSS, Temu CZ CSS etc

3. That test, or whatever it was, concluded shortly before Amazon's exit, and so Temu was already in a position of strength by mid-July and perfectly poised to spend bonkers money on ads

When asked in the comments of his post whether competitors may have less to do with CPC than we think, Ryan responded: 

“I think it's massive that Amazon stepped out, but there's enough latent budget and latent impressions that this was absorbed by the market. [This] is the water level.”

One other interesting stat I found: 

Frederick Vallaeys, CEO at Optmyzer, shared that instead of competitors benefiting from reduced competition, he discovered a “consumer expectation trap.” Vallaeys wrote:

When Amazon suddenly halted all Google Ads on July 23rd, displaced shoppers clicked on competitor ads but brought Amazon-level expectations for pricing, shipping speed, and convenience that most competitors couldn't match.

The result? More traffic, less value.

Key insight: Lower CPCs and more clicks looked great on the surface, but conversion value dropped 5.5% because displaced Amazon shoppers had expectations that most competitors couldn't profitably serve.

If you've been competing against Amazon in your niche, what have you noticed since their pullback? Hit reply and let me know.

6. AI data centers are driving up the cost of electricity for everyone

The New York Times recently reported that the tech industry's AI push is fueling soaring demand for electricity to run data centers, and that government analysts estimate that those data centers will consume as much as 12% of the nation's electricity within three years.

TechRadar reports that a new Wyoming data center could consume 5x as much electricity as what all households in the state currently use.

Holy crap! That's a lot of electricity! And we thought Bitcoin mining was bad…

Nationally, the average electricity rate for U.S. residents has risen more than 30% since 2020 after years of relatively modest increases, mostly driven by utility companies catching up on deferred maintenance projects. However in the coming years, AI could significantly accelerate those increases.

To keep pace with demand, utilities are being asked to accelerate investments in power plants and transmission lines, however the cost of upgrades are often being passed along to ordinary consumers. A June analysis, from Carnegie Mellon University and North Carolina State University, found that electricity bills are on track to rise as much as 25% in cities near data centers. 

The issue has come to a head in Ohio and Virginia, where regulators and utility companies are seeking new ways to allocate costs.

  • In Ohio, Amazon, Google, and Microsoft pushed for proposals that would lower their upfront commitments, but the state utility commission unanimously rejected those plans in favor of requiring data centers to pay a higher share of the grid improvements they require.
  • Virginia regulators are considering similar measures, but tech companies argue that creating separate rate classes for their industry is discriminatory. (LOL, wtf? Are tech companies a protected class now?) Consumer advocates counter that data centers represent the vast majority of expected electricity demand growth, making it reasonable to treat them as a distinct category. Yes, exactly that.

Meanwhile in China…

AI researchers consider the surge in demand for electricity a “solved problem,” according to a Fortune report.  China’s electricity stability stems from decades of deliberate overbuilding, with reserve margins of 80–100% nationwide compared to the U.S.’s 15% or less. Provinces covered in solar panels and a mix of nuclear and coal provide China with an abundance of electricity, allowing data centers to absorb oversupply rather than threaten grid stability.

All I know is — I'm not willing to subsidize Big Tech's AI ambitions through higher utility bills! We as a country learned from what subsidizing high-speed Internet broadband got us. Y'all are going to have to pay for this one on your own.

7. Warby Parker is ending its free glasses in-home try-on program

Warby Parker is ending its famous in-home try-on program by the end of the year, which allows customers to try out five glasses frames at home for five days. The unique program played a key role in popularizing the company after its 2010 launch, but now it's gotten much more expensive to operate.

DeAnn Campbell, a retail consultant for AAG Consulting, estimates that the company will save almost $100M per year by discontinuing the service, based on Warby Parker's volume of users and average shipping costs. Of course, that estimate doesn't take into consideration how much it'll lose in revenue by not offering the service, or how much returns will increase as a result.

In place of home try-on, Warby Parker is choosing to focus on reaching customers in-person via retail locations or through virtual try-on, having just launched an AI-powered virtual adviser to help people find the right glasses based on their facial dimensions and style preferences. The company noted that most of its recent home try-on users live within 30 minutes of one of Warby Parker’s 300 stores, and that it plans on opening five shop-in-shop stores within Target locations soon.

I think Warby Parker should better leverage brand ambassadors by sending them Try-On Kits with all their new frames, and then encouraging them to host eye glass try-on parties or bring the kits to their work and sell on commission. The same five pairs of try-on glasses they were sending out to a single customer for five days could reach dozens or hundreds of customers through well-selected ambassadors. Not to mention the social media reach of folks throwing “Warby Parties” and asking their friends online to vote on which pairs look the best.

Warby Parker already offers affiliate and influencer programs, so creating a commission-based offline ambassador program wouldn't be a big stretch. They've experimented with it in the past, but I believe the market is ripe for a 2.0 version. Imagine how many pairs of glasses a nurse ambassador could sell to coworkers at a large hospital if they brought their Warby Try On Kit with them to work and left it in the break room. Influencers, social media, and virtual try-on software are cool and all, but nothing beats picking up a pair of glasses and actually trying them on.

Would you be a Warby Parker Ambassador or buy from one? Hit reply and let me know.

8. TikTok to reduce visibility for off-platform commercial content

TikTok is updating its Community Guidelines to stress that commercial content must be disclosed and that it will reduce the visibility of content that directs users to “purchase products off-platform in markets where TikTok Shop is available.”

You heard that correctly: TikTok is openly prioritizing content that drives traffic to products on its TikTok Shop, as opposed to third-party websites or marketplaces. Makes sense, right? Honestly the transparency is welcoming.

Other updates to its Community Guidelines include: 

  • Language warning creators that they're responsible for anything that happens on their live sessions, even if it involves third-party tools like real-time translation or voice-to-text tools to read out viewers' comments, advising creators to monitor those tools to make sure they're not violating the platform's rules.
  • TikTok will begin customizing users' search results. A previous version of the guidelines said TikTok provided “search suggestions” that were relevant to the user, but now it's saying that both “search results and recommendations may look different for everyone” — indicating that the entire page of results will be different, not just the one suggested results box at the top.
  • The updated guidelines also reveal that comments are personalized too, sorted based on signals like past replies, likes, and reports. 
  • The section on AI content changed slightly with more ambiguous language around describing what sort of deepfake content is not allowed. Now it simply says that TikTok doesn't allow content that “that's misleading about matters of public importance or harmful to individuals.”

The big takeaway from the changes? If you're currently driving TikTok traffic to products on your website or Amazon, you may want to jump on the TikTok Shop bandwagon sooner than later, or risk having your content deprioritized in their algorithm.

9. Other e-commerce news of interest

eBay is crafting an “AI Defensibility” strategy to ensure it remains what it calls a “destination platform.” In a post on LinkedIn, an eBay executive revealed that the company sees challenges with AI agentic commerce and thinks it can survive by fostering genuine connections through “authentic human community.” (The same community they've repeatedly shit on for the  past 30 years?) eBay recently posted a job for a new role called Senior Director of Product – Community and Services, tasked with expanding the company's community ecosystem, including feedback, charity, and service-oriented products, emphasizing user-generated content and authentic community engagement.


Faire is expanding into 14 new European countries including Croatia, Cyprus, Estonia, Greece, Latvia, Lithuania, Malta, Slovakia, Slovenia, Bulgaria, Czech Republic, Hungary, Poland, and Romania, with more than 35,000 retailers across these countries having previously joined its waitlist. The wholesale marketplace launched in 2017 in San Francisco serving U.S. retailers and then made its move into Europe in 2021, initially launching in the U.K. and the Netherlands. Besides Europe, the company is also expanding into New Zealand, bringing its global presence to 35 markets.


Google introduced three new web payment features aimed at adding flexibility and transparency for shoppers. 1) Chrome autofill now displays reward details for over 100 credit cards. 2) U.S. buyers can use BNPL options from Affirm and Zip, with Klarna and Afterpay coming soon. 3) The company is also piloting a global money transfer tool in Wallet and Search that shows clear fee and exchange rate details from providers like Ria, Xe, and Wise.


Meta expanded its Brand Rights Protection system with new tools that let enrolled businesses report suspected scam ads at scale, including those not directly involving intellectual property via a new “Other” category. The update also streamlines takedown requests with redesigned reporting flows, added search options, clearer status notes, and AI image matching to detect online shopping violations. In 2024, Meta says it removed more than 157M pieces of ad content from Facebook and Instagram for fraud and scam policy violations.


Google researchers have been testing ways to combat non-human traffic such as bots, accidental clicks, or click fraud operations using machine learning and AI tools, which it claims have led to a 40% reduction in invalid traffic since late 2023. The system, powered by Gemini models and supported by Google Research and DeepMind, mimics human browsing behavior to detect hidden or disruptive ads before routing cases to human reviewers for enforcement, aiming to protect advertisers from wasted spend, help legitimate publishers retain revenue, and reduce risks for users.


Amazon plans on returning to its traditional two-day playbook for this year's fall Prime Day event after testing a longer four-day format in July, according to two Modern Retail sources. Amazon hasn't officially announced the return of Prime Big Deal Days this fall, other than to partially confirm that the event will take place again, saying, “We haven't announced the dates of Prime Big Deal Days yet. We'll circle back as we have news to share.”


Nearly 10,500 USPS employees accepted the agency's voluntary early retirement offer this year, which offered a $15,000 payout per employee, according to its Q3 results. The opt-in rate landed close to its expectations of 10,000 employees to participate. Reducing labor expenses is part of the Postal Service's 10 Year Delivering for America plan, launched under former Postmaster General Louis DeJoy and continued under its current leadership David Steiner, and aims to strengthen the agency's bottom line.


Alibaba introduced an AI agent called Accio Agent that claims to be able to handle about 70% of the manual steps involved in sourcing products for international trade, combining product planning, prototyping, compliance checks, and supplier searches into one process. Users start by entering a product idea and the system generates a development plan that includes market data, design details, and regulatory requirements, which can then be moved to supplier vetting, bulk request-for-quotations, and lastly a production-ready roadmap. Once approved, users can send inquiries to pre-vetted sellers on Alibaba.com and then choose a supplier.


Poshmark CEO Manish Chandra is stepping down from the role 15 years after founding the company to be replaced by current Executive Chairman and Naver President of Investments Namsun Kim. For context, Poshmark was acquired by Korean tech firm Naver in 2022 and Kim has held several positions at Naver including SVP Corporate Development, CFO, and President of Investments.


Affirm and Stripe expanded their partnership with the first BNPL integration on Stripe Terminal, now allowing U.S. and Canadian merchant to offer Affirm's installment payment options in-store directly through the terminal, which has over one million devices in use. Shoppers at participating stores will see an option to “Pay with Affirm” when they're checking out, which if chosen will prompt the shopper to scan a QR code and continue through the checkout process on their phones. As noted earlier, Affirm also expanded its partnership with Google Pay to make its BNPL payment options available via autofill on Chrome, building on its launch on Google Pay in early 2024.


Airbnb is introducing a new “reserve now, pay later” option that lets guests reserve a stay without paying anything at the time of booking and pay before the end of the stay's free cancellation period, available only for stays with moderate or flexible cancellation policies. The update goes a step further than the platform's existing “pay part now, pay later” feature, which allowed guests to split the cost between checkout and check-in, now requiring no initial payment at all.


YouTube will soon begin testing a new AI-powered age-verification system in the U.S. that differentiates between adults and kids based on the kinds of videos that the user has been watching. The system will only work when a viewer is logged into their account and will make its age assessment regardless of the birth date a user entered upon signing up. The tests will initially only affect a small group of users, with plans to expand globally if the system works well. Any other adults with children also watch kid's videos on their account? And is there a big difference between what a 19-year-old and 17-year-old watch on YouTube? This seems like a terrible idea.


In June I reported that Sezzle, the Minnesota-based BNPL platform, filed an antitrust lawsuit against Shopify, accusing it of monopolistic practices to limit competition for BNPL payment options on its platform and claiming that Shopify “manipulated” potential Sezzle customers into using its own BNPL service, which is powered by Affirm. The two companies have since not been able to agree on a resolution, and Shopify said in court filings last Monday that it will ask a federal judge to dismiss the suit in a hearing on Dec 12th. I mentioned in June that if if Sezzle were to come out victorious, it could open the door for other payment providers like PayPal, Apple, Google, Amazon, and Bolt to have a case against Shopify for favoring Shop Pay.


The estate of Daniel Dumile, better known as the British rapper MF DOOM, is suing Temu on allegations that the company is selling knockoff merchandise of the late musician. The suit claims that Temu “manufactured and sold a myriad of items that are counterfeit or blatant copies of Plaintiff's artwork, products, trademarks, and intellectual property,” going on to call Temu “one of the most unethical companies operating in today's global marketplace.”


Microsoft is looking to one-up Meta in the AI talent war by poaching engineers that the company itself lured from other startups. Microsoft put together a list of the top engineers and AI researchers at Meta and aims to match Meta's compensation as part of its new process to make its offers more competitive. Current engineers and researchers at Microsoft have maximum compensation packages of $408k, $1.9M in on-hire stock wards, $1.5M in annual stock wards, and annual cash bonuses as high as 90%, all which Microsoft is willing to exceed to fuel its AI efforts.


JD.com posted a job opening for a DeFi expert, seeking talent familiar with DEXs, lending, derivatives, and token economics. The move comes as Hong Kong's stablecoin licensing regime officially took effect on August 1, offering a compliant way for companies to issue fiat-pegged digital currencies. The job description also hints at the Payment Finance model, which uses smart contracts to merge payments with programmable financial services.


Amazon launched its direct-from-manufacturer discount platform, Amazon Haul, in beta in Australia to take on Temu, which launched in the country in March 2023. All products in Australia are available for sale under $25, with free delivery offered on orders over $40 and an $11.99 charge on orders below that threshold. I'd imagine Amazon set that non-free shipping amount so high that customers will be like, “Well, I'll just add another $XX amount of product to my cart to reach that $40 threshold.”


Temu signed a deal with Austrian Post to offer a “local-to-local” customer experience aimed at improving its image in the EU. Austrian Post will soon integrate Temu's pick-up and drop-off service that allows customers to collect from and return orders to nearby lockers and convenience stores, replacing Temu's current system of redirecting orders and returns to external delivery apps or websites. Temu will also sign contracts with Austrian Post subsidiaries in Bulgaria and Hungary, following a similar deal with Germany's DHL in April, eventually hoping to process up to 80% of European sales using the local-to-local structure.


🏆 This week's most ridiculous story… A 52-year-old man named Scott Jacqmein licensed his likeness to TikTok last year, which subsequently created a digital avatar that now hawks everything from insurance marketplaces to horoscope and brain teaser apps. Jacqmein said he was paid $750 and a trip to the Bay Area for his work and that now he has “regrets.” He said he receives at least one or two texts a week from friends and acquaintances who are pretty sure they saw him pitching something on TikTok.

10. Seed rounds, IPOs, & acquisitions

OpenAI employees are planning to sell around $6B worth of shares at a $500B valuation, with Thrive Capital, SoftBank, and Dragoneer Investment Group among the investment firms expected to buy the shares, according to Bloomberg sources. The secondary sale is still in progress and is higher than OpenAI's latest private market valuation of $300B this past March. Current and former employees have already sold $3B worth of shares, and the new sale would push total cash outs to $9B if completed.


Jump, a ticketing and fan experience platform for professional sports team, raised $23M in a Series A round led by Seven Seven Six at over a $100M valuation, bringing its total amount raised to $58M. The startup aims to be the “Shopify for sports teams,” providing the tech infrastructure to handle ticket sales, merchandise, and concessions, with features like the ability to upgrade tickets during the middle of a game or order concessions directly to your seat.


Drivepoint, an AI-powered strategic finance platform that helps brands optimize financial planning and decision making, raised $7M in a Series A round led by Vocap Partners, bringing its total amount raised to $9M. Additional new capital comes from Good Friends VC, the venture firm founded by the creators of Allbirds, Harry's, and Warby Parker, with Allbirds co-founder Joey Zwillinger personally leading the investment. The company will use the funds to accelerate AI product development in forecasting, variance analysis, and decision intelligence, as well as scale its go-to-market efforts. 


Almedia, a rewarded user acquisition ad platform best known for its Freecash brand, which offers monetary incentives to users for engaging with mobile games and apps, acquired Zave.it, a German cashback and rewards app that lets users earn money back when shopping online at retailers, while simultaneously supporting their favorite creators with each purpose. The deal aims to provide Almedia with closer partnerships to the retail and financial sectors as it aims to build Freecash into an “engagement engine.”


Crocs is investing $80M to expand its North Las Vegas operations into a central e-commerce distribution and fulfillment hub that will ship all Crocs products across the U.S. The project, supported by $4.6M in tax abatements, is expected to create 70 jobs paying an average of $34/hour and generate $20M in new tax revenue over the next decade and is part of Crocs’ supply chain optimization strategy, consolidating distribution for both its flagship brand and Heydude.


Bumper, a UK-based BNPL platform for car repairs and maintenance, raised $11M in a Series B extension round led by Autotech Ventures. The company, which is now operationally profitable and on track to exceed £1B in GMV this year, will use the funds to scale its BNPL service for drivers across Europe, while expanding its offering to dealers and OEMs through recent acquisitions and new product launches.


Evertune, a generative engine optimization and AI marketing platform that helps brands understand and influence how they appear in AI search results, raised $15M in a Series A round led by Felicis Ventures. The platform runs more than 100k AI prompts per brand to deliver statistically relevant insights and prepare companies including Canada Goose, Miro, and Choreograph for AI-driven discovery, advertising, and commerce.


Profound, a NY-based platform that also helps businesses control how they appear in AI responses, raised $35M in a Series B round led by Sequoia, bringing its total amount raised to $58.5M. Since launching less than a year ago, the platform has attracted enterprise customers including Ramp, U.S. Bank, Indeed, Chime, and 500 other organizations to its platform seeking help establishing their presence within AI discovery. 


PayPay, Japan's largest mobile payment app with more than 70M users, filed for an IPO in the U.S., seeking to raise more than $2B at a $10B valuation. If the listing is approved, it would mark the largest IPO for a Japanese company on a U.S. stock exchange in history. The listing could help PayPay's parent company SoftBank with its AI ambition, whose founder Masayoshi Son recently pledged $500B to the Stargate project and is exploring a robotics and AI complex in Arizona.


Click Labs Inc, a U.S. provider of on-demand app development, SaaS products, and digital transformation solutions, acquired Evermile, a London-based AI retail operations platform built or SME retailers, for an undisclosed amount. The acquisition aims to strengthen Click Labs' position in the retail tech space and bring advanced automation and AI capabilities to its retail clients.


Chowdeck, a Nigerian restaurant and food delivery platform, raised $9M in a Series A round led by Novastar Ventures. The company will use the funds to expand into more cities across Nigeria and Ghana, as well as launch a quick commerce strategy to boost speed and efficiency of its grocery and local markets delivery services.


Merge Labs, an OpenAI-backed startup that will compete with Elon Musk's Neuralink by connecting human brains with computers, is aiming to raise $250M at an $850M valuation, with much of the new capital expected to come from OpenAI's ventures team. Sam Altman will cofound the company but not personally invest or have a day-to-day role in the business. Wait, how is that considered cofounding? Perhaps OpenAI should concentrate on securing its own operational funding before investing in startups that fuel Sam Altman's rivalry with Elon Musk.


Perplexity AI made an unsolicited $34.5B bid to buy Google Chrome, right as a legal ruling is pending in an antitrust case that could force the company to divest its browser. Several investors and VC funds have “agreed to back the transaction in full,” according to the Wall Street Journal. As part of the offer, Perplexity, which is only valued at $18B and currently operates in the red, said it would commit to investing $3B over 24 months “in reliability, performance, security, and customer support scale,” as well as make employment offers to the majority of key personnel responsible for developing Chrome. Earlier this summer, Perplexity tried to buy Brave, a privacy-focused web browser and search engine, but the discussions stalled.


Rivos, a California-based AI chip startup focused on building server-class processors optimized for LLMs and data analytics, is seeking to raise up to $500M at a valuation of more than $2B, which would bring its total amount raised to $870M, according to The Information sources. If finalized, the new round would bring Rivos' total funding and valuation to a record amount for a chip startup that has yet to mass-produce a single chip.


Cohere, a Toronto-based AI company that develops LLMs and provides enterprise-grade AI solutions for search, summarization, and conversational applications, raised $500M in an oversubscribed round at a $6.8B valuation, up from $5.5B a year ago during its previous $500M round. Cohere was one of the first breakout larger language model makers, cofounded in 2019 by Aidan Gomez, one of the authors of the “Attention Is All You Need” paper that became the foundation of modern AI. The company's market proposition has always been to offer secure LLMs geared for enterprise use, not for consumers.

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PAUL

Paul E. Drecksler
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PS: This week's comic relief is brought to you by Datch Haven at this ecommerce life.

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