#230 – Stablecoins, Superintelligence Teams, and Shopify’s landmark lawsuit

by Paul Drecksler | Jun 16, 2025 | Recent Newsletters

Hi Shopifreaks

I hope all the fathers who read this newsletter had a great day yesterday, which personally marked my 3rd Father's Day since Mia was born. When I launched this newsletter in Jan 2021, I had no idea that four years later I'd be celebrating 18,000 subscribers with a 2 year old daughter! Life comes at you quicker than e-commerce news sometimes…

As usual I've got a very big edition for you this week that covers:

Shopify's crypto partnership with Coinbase and Stripe
Sezzle's landmark lawsuit against Shopify
Meta's superintelligence group
Walmart expands drone delivery
Twice as many Amazon Prime Video ads
Salesforce silos Slack data
The US / China trade deal
Etsy's crackdown on 3D printed items
Amazon's potentially discriminatory RTO policy
Snap's aggressive offer to advertisers
Google gaining ground with Gen Z

All this and more in this week's 230th Edition of Shopifreaks. Thanks for subscribing and sharing!

Stat of the Week

The share of Gen Z shoppers going to Google first, even when they know what they want, rose to 30% in March from 21% in September 2024, while Amazon’s share dropped from 41% to 34%, according to Morgan Stanley data. Analysts suspect Google’s generative AI tools, including AI Overviews and Lens, are driving the shift. While ChatGPT adoption remains low for shopping, Google appears to be holding younger users' attention with its AI-powered features.

1. Shopify embraces stablecoins across its platform

Shopify partnered with Coinbase and Stripe to natively enable merchants to accept USDC stablecoin payments globally, without any 3rd party integrations or gateways required. The option to pay with USDC will appear in Shopify's coveted payment dropdown area, right below the credit card option on the checkout page, as opposed to opening a pop-up or taking customers to a 3rd party site to complete their purchase.

USDC is the world's second-largest stablecoin behind USDT, with a $61B market cap — which means there are around 61B tokens in circulation. USDC is issued by the crypto company Circle, which recently raised $1.1B in its IPO on the NYSE. Unlike traditional cryptocurrencies, stablecoins are designed to maintain a stable value by being pegged to a reserve asset like the U.S. dollar, making them more suitable for payments.

Quick Backstory: The original vision of Bitcoin was to function as a currency, but mining fees made it inefficient and expensive to transfer BTC. Also, no-one wanted to spend their BTC because they hoped it would go up in value. As a result, Bitcoin evolved into a store of value, leaving room for stablecoins to emerge as a more practical option for crypto-based payments.

Back to the Shopify news…

By default, all USDC payments within Shopify will be converted to the merchant's local currency, with no foreign exchange or multi-currency fees, and payouts will be deposited into the merchant's existing bank accounted connected to Shopify Payments. Coming soon, Shopify will offer merchants rebates of up to 0.50% on USDC orders, and in the future, customers in the U.S. will receive a further rebate for using the payment method. The stablecoin payments should also clear faster than traditional fiat payments, which move from Shopify to merchants via ACH transfer and take several days.

What about buyer protections, refunds, and chargebacks?

That was one of my first questions, given that crypto is notorious for being a ‘buy at your own risk' transactional medium. However as part of the partnership, Shopify and Coinbase co-developed protocols to handle chargebacks, refunds, and other intricacies of retail payments on Coinbase’s blockchain, Base, which is the fourth-largest blockchain for USDC. The actual transactions will run through Shopify's existing payment processing partner, Stripe. Buyers who shop with USDC on Shopify should be as protected as they are with normal fiat transactions.

Shopify CEO and Coinbase board member Tobias Lütke said onstage at a Coinbase conference last week:

“In our own philosophical framework, we are extremely aligned with everything that crypto stands for.”

USDC payments are currently in early access for select merchants and will rollout to all merchants across 34 countries in the coming weeks.

2. Sezzle sues Shopify for monopolistic practices

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.

The lawsuit claims Shopify “manipulated” potential Sezzle customers into using its own BNPL service, which is powered by Affirm, causing competitors to lose out on sales, and that Shopify “copied” Sezzle's BNPL product and business model by rolling out Shop Pay Installments.

Sezzle said in its lawsuit that in 2018 two senior Shopify executives visited the company “under the guise of ‘corporate development,’ and falsely suggested to Sezzle that Shopify was interested in acquiring or joint-venturing,” but that Shopify’s real purpose was to get as much knowledge about its business as possible so they could copy it.

It goes on to claim that Shopify is engaging in “monopolistic and anticompetitive business practices in order to stifle competition” for BNPL services on its e-commerce platform, alleging that the company used its market power to favor its own BNPL service for merchants, crowding out competitors .

Sezzle, which launched in 2017, alleges that it once had a “symbiotic relationship” with Shopify, but now Shopify intentionally makes it more difficult for consumers to find alternative BNPL providers, and that even if consumers selected Sezzle as a BNPL option when buying a product, Shopify would “intercept” consumers and have them pay through Shop Pay Installments instead.

Although Shopify accounted for less than 5% of its Q1 revenue, Sezzle argues that the lawsuit is key to protecting merchant and consumer choice. It's seeking an injunction and treble damages, paid out in 4 interest free installments. (LOL, j/k on that last part.)

Here's why this is a huge lawsuit:

Doesn't Shopify limit ALL types of payment options on its platform (not just BNPL)? They've historically moated the shit out of payments. That's kind of their thing — which makes this Sezzle lawsuit fairly landmark.

If Sezzle were to come out victorious, would it open the door for other payment providers — like PayPal, Apple, Google, Amazon, Checkout, Bolt, etc — to have a case against Shopify for favoring Shop Pay? And if so, does that give Shopify a huge incentive to settle this out of court?

Or has Shopify grown so big that it's too late? Did their model of steering merchants towards their internal payment processing service work as a startup, but now that they're a market leader, it's considered monopolistic?

Does Shopify even have to allow alternatives to its own payment processing on its platform? Comparably, Amazon also partners with Affirm for BNPL payments, and not Sezzle, which isn't an option at all on the site. Can Sezzle sue Amazon for not integrating its BNPL service, which could be considered worse than allowing it and steering customers away from using it?

The impact of this Sezzle vs Shopify lawsuit is larger than most people realize, and I'll be following it closely.

I'd love to hear your thoughts on the case. Hit reply to this e-mail or join the conversation on LinkedIn.

3. Meta is recruiting a “superintelligence group” to advance its AI efforts

Meta is forming an AI Superintelligence Team comprised of around 50 engineers, with Mark Zuckerberg personally overseeing recruitment. Zuckerberg has reportedly been discussing potential recruits with other senior leaders from the company in a WhatsApp group chat dubbed “Recruiting Party.”

He's also been inviting AI researchers and infrastructure engineers to his homes in California over the past month to invite them to join his team. Bloomberg shared that Zuckerberg decided to oversee recruitment himself due to his frustration over the public's response to its Llama 4 model, which was criticized as overpromised and underdelivered.

And apparently the one-on-one recruitment and extra effort is necessary, as Meta has reportedly been losing AI talent to startups like OpenAI and Anthropic, despite offering compensation packages exceeding $2M (with one offer rumored to have been worth over $10M).

The other part of Zuckerberg's master plan is the company's upcoming $15B investment in Scale AI and the recruitment of its founder Alexandr Wang, who will take a senior position at Meta.

Meta's goal is to outpace competitors in achieving artificial general intelligence, or AGI, which is the theoretical notion that machines can perform better than humans at many tasks. Zuckerberg says that Meta's advantage is its advertising business, which can subsidize its AI business, unlike competitors which have to raise capital.

Currently Meta is off to an embarrassing start with its AI efforts…

Meta is taking heat for its standalone AI chatbot app publishing users' conversations to a public “discover” feed, including very personal information about their romantic lives, work problems, and even sexual fantasies. One conversation even included a person's phone number and e-mail address when they asked for help drafting a letter to a judge in a child custody case.

Meta says that AI chats are set to private by default and that users have to actively tap the share or publish buttons before the conversations show up on the app's discover feed, however, the button doesn't explicitly tell users where their conversations will be posted, which confused many users.

Does it really take a “superintelligence team” to tell Mark Zuckerberg that publicly sharing people's private conversations with AI chatbots is a bad idea?

4. Walmart expands its drone delivery service in five cities

Walmart is expanding its drone delivery program with its partner Wing to 100 additional stores across Atlanta, Charlotte, Houston, Orlando, and Tampa, building on years of testing in Texas and Arkansas. The expanded program is set to reach 3M more households.

The company first began doing commercial drone deliveries in 2021 and has since completed 150,000 deliveries through its partnerships with Wing and Zipline. The deliveries take about 20 minutes on average, with a four-minute average flight time, according to Walmart. So far the drone service has focused on small, urgent items like groceries and medicines, but that could change as its capacity increases.

Wing's drones have a payload of two pounds, but they company is working on a new model that can carry up to five pounds, which means they'll be able to carry about half of the 120,000 items typically found at a Walmart Supercenter. While the new drones won't be able to carry a gallon of milk, which weighs eight pounds, it'll be able to bring you a quart to get you through the morning.

Wing CEO Adam Woodworth says that customers commonly order baby wipes (for obvious reasons) and surprisingly eggs — which he later learned was to test the technology's handling capabilities.

Wing told Business Insider that the immediate reaction of drone delivery service being introduced to a neighborhood is often a negative one. However the company does demos to get communities more comfortable with the idea, and eventually the questions go from negative to, “Okay, well, when is it going to come to my house?”

5. Amazon doubles the number of Prime Video ads

Amazon has increased Prime Video’s ad load to 4-6 minutes per hour, up from an initial 2-3½ minutes when the ad-based subscription tier launched in January 2024. When Amazon introduced ads on Prime Video, it said it aimed to have “meaningfully fewer ads” than rivals. However by by late 2024, the company had already told investors it would “ramp up” the volume in 2025.

Netflix's ad-supported tier currently offers the lightest ad experience, while Hulu, Tubi, and Paramount+ carry heavier loads. At the moment, Prime Video sits in the middle, but I don't imagine that Amazon will settle for anything but first place. Classic Ricky Bobby mentality.

This was one of my 2025 Predictions from our annual report:

“Amazon Prime Video will look to see just how far it can push viewers with ads before they either cancel or upgrade to an ad-free experience (which I'm confident will also go up in price next year).”

It seems that Amazon has already started down that path.

The question is — where will it stop?

The answer depends on how many ads Prime Video viewers are willing to endure before spending the $2.99/month to upgrade to the ad-free experience, which used to be included free as part of your general Prime subscription. I guarantee Amazon won't stop until it breaks you.

I'm still waiting for the class-action lawsuit against Amazon by Prime members who paid for an annual membership pre-Jan 2024 that included an ad-free video experience, only to have the benefit stripped away without warning. Why hasn't anyone sued Amazon over this? They certainly deserve it. Feels like a slam dunk case.

The other half of my prediction was that Amazon increases the cost of its ad-free experience in 2025. Who's going to bet against me?

6. Salesforce restricts competitor access to its Slack data

Salesforce has blocked third-party apps from indexing or storing Slack messages long term, even if their customers permit them to do so, according to a public disclosure from the company. Salesforce acquired Slack in July 2021 for $27.7B.

The move is a hindrance to AI startups that have used access to this data to power their services. Glean, for example, which describes itself as “Work AI,” helps organizations unify, search, analyze, and automate operations using their internal data from 100+ systems. The platform indexes your internal content, builds a knowledge graph of employees, documents, and workflows, and then offers personalized search and content generation.

Slack data, as any company that uses the service can testify, is a very crucial part of that knowledge graph, and up until recently, Glean was able to use it. However now, since the changes, Glean and other apps can no longer index, copy, or store the data they access via the Slack API on a long-term basis, according to the disclosure. Salesforce will continue allowing firms to temporarily use and store their customers’ Slack data, but is now requiring that they subsequently delete it after a certain period of time.

Salesforce says the change improves data security, but it's obvious that the move is designed to silo off Slack data for Salesforce's own AI ambitions and put competitors at a disadvantage.

Glean wrote an e-mail to customers informing them that the changes will prevent them from adding Slack data to their Glean search index, thereby “hampering your ability to use your data with your chosen enterprise AI platform.”

Class Big Tech Move: Build your market share with the support of partners through open protocols, and then later abuse your dominant position by shutting off or charging for access.

It raises the question for Slack users: Is that your data (Salesforce) or my data? And if it's mine, how is it that you can restrict access to it for the tools that I choose to employ?

7. The U.S. and China reach a much anticipated tariff deal

The U.S. and China struck a tentative “framework” agreement last week to ease tariffs and calm tensions. After two days of negotiations in London, officials from both countries announced that they’d reached a new understanding, built on the preliminary deal struck in Geneva in May. Commerce Secretary Howard Lutnick framed the talks as progress, saying negotiators had “put meat on the bones” of the earlier agreement.

The updated framework reduces President Trump’s 145% tariff on Chinese imports to 55%, and China's retaliatory tariffs on U.S. exports to 10%. Note that the 55% tariff is inclusive of an additional 30% on top of the blanket 25% tariffs from Trump's first administration, as Jon Elder points out. (ie: It's not 55% on top of the 25% previous tariff.)

As part of the deal, China also agreed to issue six-month rare earth export licenses to U.S. firms, and the U.S. is expected to ease tech export restrictions and visa cancellations.

President Trump declared victory on Truth Social, stating, “Our deal with China is done.” However it still technically requires both President Trump and President Jinping's approval, and implementation dates have not yet been announced.

Critics say the deal mostly resets trade talks to where they were a month ago, without resolving fundamental issues. I vote that any type of permanence with tariffs is better than the instability we've been dealing with for the past several months.

8. Etsy cracks down on 3D and laser printed items

Etsy made updates to its creativity standards, effective June 10, 2025, restricting the sale of 3D and laser printed items made from other people's templates, scanned vintage digital files, and generic resold goods. The changes also clarify restrictions on nature-based products and commercial holiday decor sourced from wholesalers and bulk manufacturers.

While 3D and laser printed items are still welcome on the platform, Etsy is now emphasizing in its TOS that the items must be produced based on a seller's original design “and are often personalized or customized to a buyer's specification.”

Value Added Resource also notes that Etsy removed mention of “digital files of scanned vintage content like photographs, books, or patterns” from its seller terms, which could mean that these items are no longer allowed to be sold on the site at all. As usual, Etsy didn't provide any clarification about the changes.

Some sellers are criticizing Etsy for implementing the new rules without notice, which could lead to account suspensions before they have time to adjust their listings, while others support the tighter standards to preserve Etsy’s original handmade identity.

Etsy began purging products in 2024 after introducing “Creativity Standards” to reassure shoppers that the platform still had a human touch. Under the policy, every items on Etsy had to fit into four categories:

Made by seller
Designed by seller
Handpicked by seller
Sourced by seller

Those new Creativity Standards are fluid, and the company continues to adapt its interpretation of the rules.

9. Other e-commerce news of interest

Amazon's return-to-office policy is facing complaints from disabled employees who say it violates the Americans with Disabilities Act and labor rights. At least two workers have filed complaints with the EEOC and NLRB, citing Amazon’s resistance to remote work accommodations and alleged retaliation against employees advocating for disabled colleagues. An internal survey of over 200 workers found that 71% reported unmet accommodation requests, and 50% described hostile work environments. Amazon says its accommodation process is “empathetic” and “individualized,” but workers say the company's use of AI to evaluate disability requests lacks the necessary human judgment.

The Postal Regulatory Commission is proposing to limit USPS rate increases for “Market Dominant” services, such as First Class and Media Mail, to once per fiscal year, reversing the twice-a-year policy enacted in 2021 under former Postmaster General Louis DeJoy. The proposed rule would apply from October 2025 through October 2030, aiming to improve rate predictability and reduce administrative burden. In the meantime, USPS continues to raise service rates like Ground Advantage up to three times a year, with one increase expected in July and another in October this year.

TikTok is rolling out a new badge system to highlight reputable sellers as it expands in-app shopping. Badges include “Official Shop” and “Authorized Seller” for verified sellers, as well as “Gold Star” and “Silver Star” badges for businesses meeting high customer service standards, while a “Top Brand” badge (which carried over from the old system) recognizes brand popularity and service. The new badges will appear across content such as LIVEs, product detail pages, short videos, and in search, aiming to increase transparency and trust for buyers and encourage sellers to prioritize service. It's nice how TikTok awards good sellers with badges, while Amazon's badges are like, “Frequently Returned.”

Shopify chief design officer Carl Rivera removed “UX” and “content designer” from job titles to encourage designers to focus on human skills like taste, intuition, and creativity, rather than codified best practices that AI can now replicate. Rivera argues that standardized UX delivers predictable but forgettable experiences and that great design must go beyond what AI can generate. Bold decisions (like title changes) that have absolutely no impact on job responsibilities or compensation are why we pay him the big bucks! In all seriousness, it makes sense theoretically, but Shopify is still limited to operating within browsers and mobile apps, which come with design and user experience constraints. It feels like the title changes add unnecessary ambiguity to design roles, but it's possible I just don't get it.

Snap is aggressively offering advertisers free ad credits in exchange for increased ad spend in anticipation of a potential TikTok ban (which is expected to be delayed for a third time), hoping to position itself as the biggest benefactor if TikTok were to disappear in the U.S. Three media buyers who spoke to Adweek claimed to have been directly pitched incentives like an additional 10% or 20% in bonus ad credits for spending $50k or $100k on the platform. However, none of the advertisers said that they took advantage of the offers, increased budget with Snap, or moved budget from TikTok as a result of the incentives.

Meta filed a lawsuit against Hong Kong-based Joy Timeline for running ads on its platforms promoting “nudify” apps that digitally undress people without consent. The legal action follows a CBS News investigation that uncovered hundreds of ads for the apps across Facebook, Instagram, and Threads. Meta said it removed many of the offending ads and accounts but acknowledged that enforcing policies is becoming harder as AI-generated exploitative content evolves. Meta says that the lawsuit “underscores both the seriousness with which we take this abuse and our commitment to doing all we can to protect our community from it,” and that it'll continue to take legal action against advertisers who abuse its platform in the future.

Klarna partnered with gift platform Nift, a Boston-based platform that helps businesses acquire and retain customers with gift cards to other businesses, to enhance its customer experience and loyalty through personalized gift offers. Through the collaboration, Klarna will reward users with tailored gifts based on their preferences from brands like Chewy, HelloFresh, and SiriusXM. Early results show a 30% click-through rate and 40% gift activation rate in the U.S.

Meta is rolling out its “Opportunity Score” optimization metric to all ad accounts, following its testing with select advertisers earlier in the year. The score ranks opportunities 0-100 based on how many AI-driven recommendations advertisers implement to improve campaign setup and performance, most comparable to Google Ads' Optimization Score. The company is also introducing a streamlined Advantage+ campaign setup that defaults to AI optimizations, which in testing reduced cost per result by 12% and improved CPA by 7-9%.

HuffPost, Washington Post, and Business Insider have all seen search-driven organic traffic drop by 50% or more during the past three years, according to The Wall Street Journal, with Google's rollout of AI Mode expected to deliver an even stronger blow in the months ahead. Nicholas Thompson, CEO of the Atlantic, predicted at a companywide meeting earlier this year that the publication should assume traffic from Google would drop toward zero and advised that the company evolve its business model accordingly. Google executives have said that its search business remains committed to sending traffic to websites and that it doesn't necessarily show AI Overviews when users search for trending news. Thanks Google, because companies don't earn ad revenue from archived posts?

Jason Buechel, who became Whole Foods CEO in 2022 and was promoted to oversee Amazon's global grocery business earlier this year, assembled a leadership team to reorganize and run the company's entire grocery operation, including Whole Foods, according to an internal memo obtained by Business Insider. The move aims to streamline operations, eliminate duplicated efforts, and integrate Whole Foods more tightly with Amazon, eight years after its $13.7B acquisition. Buechel’s new structure covers technology, logistics, marketing, and HR, with leaders now tasked with driving efficiency and growth across the entire division.

AI isn't just disrupting the job marketplace, it's also apparently disrupting the environment. In a recent blog post, OpenAI CEO Sam Altman claimed that ChatGPT uses minimal water and electricity per query, but Gizmodo author Kyle Barr says that his estimates starkly contradict prior academic research. Altman suggested a single prompt consumes just 0.34 Wh and 0.000085 gallons of water, but Barr contests that he offered no data sources and failed to account for high-usage models or image generation demands. Barr and other critics argue that Altman’s claims reflect Silicon Valley’s tendency to minimize the environmental impact of scaling AI.

GameStop reported a 17% drop in Q1 revenue to $732.4M, as more customers opted for digital downloads over physical games. Hardware and accessories sales fell 32%, and the company announced further store closures after shutting nearly 600 U.S. locations in 2024. CEO Ryan Cohen says the company's future isn't in games, and that it's doubling down on trading cards, especially Pokémon, as a “natural extension” of its business, citing their high margins and recent surging demand. The company now offers in-store drop-off services for PSA card grading and has facilitated over one million card submissions.

France advanced legislation aimed at curbing “ultra-fast fashion” platforms like Shein and Temu, with new measures including a €2 to €4 parcel fee on non-EU shipments and an outright advertising ban on the retailers. Traditional fast fashion retailers like H&M and Zara were exempted after lobbying, as to differentiate between “fast fashion” and “ultra-fast fashion.” Critics argue it will hurt cost-conscious consumers, but proponents feel the juice is worth the squeeze in regards to mitigating the environmental and economic harm that these companies are causing in the country. Shein and Temu shipped 800M parcels to France in 2024, which accounted for more than half of all parcels sent to the country last year. Together with Amazon, the three retailers now account for 24% of online apparel sales in the country.

In lawsuits this week… Google is facing a £1.04B legal action headed to trial in October 2026 that accuses the company of “abusing its dominant position to the detriment of thousands of UK businesses.” Canada's Competition Bureau is suing DoorDash for allegedly misleading consumers by advertising its services at a lower price than what customers actually end up paying, due to mandatory fees at checkout. Last but not least, a Google shareholder named Tony Tan is suing Alphabet for wrongfully denying a request he made for internal documents about Google's decision to risk billions of dollars in fines by not complying with the TikTok ban. He seems to forget that President Trump instructed the DOJ not to enforce the ban the day after he took office. The whole lawsuit is kind of weird, and Tan has a history of these types of lawsuits.

The UK Financial Conduct Authority appointed Sarah Pritchard as its deputy CEO, a new role created to reflect the regulator’s growing responsibilities, including oversight of crypto firms, stablecoins, and BNPL products. Pritchard, who joined the FCA in 2021, will continue to oversee consumers, competition, and international engagement while supporting the agency’s reform agenda and international strategy. Way to keep up with the times!

Google offered voluntary buyouts to U.S. employees in its knowledge and information group, which oversees search and much of its ads business, its core division, which is the engineering team working on Google’s underlying technical infrastructure, as well as its research, marketing and communications divisions, as the company faces threats from ChatGPT and fallout from its U.S. antitrust loss. The move follows buyouts and layoffs in other units like platforms and devices and the ads organization earlier this year, suggesting potential further cuts ahead.

TikTok and ByteDance conduct biannual performance reviews using a rating curve that managers are instructed not to discuss openly, according to internal documents viewed by Business Insider. The documents revealed that only 10% of employees can receive the top four ratings, with the top three capped at 5%. Managers are told to use discretion rather than formulas, weighing output, cultural alignment, and leadership traits, while avoiding terms like “forced distribution.” Staff fear that low ratings could trigger PIPs or exit offers, especially after March reviews led to cuts in underperforming divisions like TikTok Shop US.

Meta is adding AI-powered video editing features to Meta AI that let users edit short videos with preset prompts to makes changes to costumes, styles, and locations. For example, users can apply a vintage comic book style to a video, change the lighting in a clip to a rainy day, or swap out the person's clothing for a space suit. The features are rolling out in the Meta AI app, Meta.ai website, and its CapCut competitor Edits, with plans to expand customization options later this year based on creator feedback.

Deloitte US expanded its $1,000 annual wellness subsidy to include items like Lego sets, puzzles, kitchenware, and spa services. Employees can now expense items such as the $850 Star Wars Millennium Falcon Lego set, gaming consoles, and ergonomic sleeping pillows. The subsidy was originally designed to be spent on subscriptions, equipment, and experiences meant to “empower and support your journey toward thriving mentally, physically, and financially and living your purpose.” Workers welcome the new perks, but also say it highlights the intensity of the job. Deloitte US has recently faced layoffs and contract cuts tied to reduced federal spending.

Meta is showing more ads to older Facebook users, as they have higher purchasing power and conversion rates, according to a Barclays report citing internal documents from Meta's FTC trial. Users aged 45 to 54 saw the highest ad load (22%), while teens saw just 4.3%, reflecting Meta’s strategy to optimize revenue by targeting valuable demographics rather than increasing overall ad volume. Meta’s dynamic ad tech, powered by machine learning models like Andromeda and Lattice, helps it selectively show ads to users most likely to click, allowing the company to grow ad revenue without increasing ad density across the board to all users.

Retailers capitalized on both the U.S. Army's 250th anniversary parade and the ‘No Kings' protests against the Trump administration, which took place on the same day. Hundreds of items appeared for sale on Amazon, Etsy, and even Temu like t-shirts and hats that cashed in on the two coinciding events, with messages like “250 Years Defending Liberty” versus “No Kings in America.” No matter which side you're on, retailers are going to retail.

Klarna created an AI voice chatbot of its CEO Sebastian Siemiatkowskito that customers in the U.S. and Sweden can call for support. Business Insider's Jordan Hart called the chatbot to ask questions about the role that AI will play in displacing workers. It gave a pretty convincing answer that sounded just like Siemiatkowski, making me wonder if there's ever been a real Sebastian Siemiatkowski or if he's been a chatbot all along…

Squarespace launched a new brand campaign across Australia and New Zealand called “Click! Click! Click!”, which celebrates tradespeople like landscapers, painters, and electricians as the backbone of small business. The ad, inspired by the folk song “Click Go the Shears,” reimagines the tune to show how tradespeople can quickly build a digital presence with just a few clicks on Squarespace. The message at the end of the video was a bit weird, which read, “A website makes it real” — as if these folks haven't been running a real business until they have a Squarespace site. Are we celebrating tradespeople or negging them?

🏆 This week's most ridiculous story… A former TikTok influencer who had 2.5M followers was so upset that she got banned from the platform, that she went to TikTok's offices and tried to get her account back. Natalie Reynolds was filmed crying and screaming outside the building while on the phone with her dad. “Dad, they won't let me in. I need my TikTok account unbanned.” Neither TikTok or Reynolds shared the reason why she was banned, but it likely had to do with a controversial prank video she published in May, where she paid a homeless woman who couldn't swim $20 to jump in a lake, and then left her there.

10. Seed rounds, IPOs, & acquisitions

Ramp, a New York-based corporate card and expense management startup that helps businesses control spending and automate financial operations, is in talks to raise $200M at a $16B valuation, marking an increase from its $13B valuation this past March, and more than double its valuation when it raised capital in April 2024. The new funding would bring it's total amount raised to $2B. Ramp was generating $700M in annualized revenue as of the end of January.

Stripe acquired Privy, a New York-based developer platform that provides APIs to help businesses easily build crypto wallets and integrate on-chain capabilities without requiring users to manage their own keys, for an undisclosed amount. Privy powers more than 75M crypto accounts across more than 1,000 developer teams and orchestrates billions of dollars in transactions while helping users earn, move, and use new crypto assets.

Chime, a San Francisco-based neobank that offers fee-free banking services like checking accounts, savings accounts, and early access to direct deposits, raised $864M in its IPO, pricing its shares at $27 and giving it a fully diluted market cap of $11.6B. The stock ended its first day of trading at $37.11, marking a 37% bump over its IPO price. Chime reported $1.7B in revenue in 2024 and became profitable in the first quarter of 2025 with $13M in net income on $519M in revenue.

DoorDash acquired Symbiosys, an ad tech company that builds tools to help publishers and advertisers optimize campaigns through data-driven insights and automation, for $175M. Symbniosys will continue to operate independently under its own name and will keep working with its other commerce media clients, while collaborating with DoorDash to build better ad tools for restaurant owners, merchants, and CPG companies that buy ads on its platform. Alongside the acquisition, DoorDash announced that it surpassed $1B in annualized ad revenue and unveiled a new suite of AI-powered ad tools for merchants that sell on its platform.

OnlyFans, your boyfriend's favorite social network, is exploring a potential $8B sale, far below valuations of similar content platforms, largely due to the type of content it hosts. The company has a 50% profit margin, which is significantly higher than those of Netflix and Spotify, and would be worth up to $45B if it was valued like mainstream media companies. However risks like regulatory scrutiny, content moderation challenges, and potential competition from adult AI chatbots, as well as the site's heavy reliance on volatile microtransactions, keep institutional investors wary.

Anne Wojcicki, co-founder of 23andMe, is reclaiming the company through her new nonprofit TTAM Research Institute, which has agreed to acquire nearly all of 23andMe’s assets for $305M, including its DNA testing business and telehealth unit Lemonaid Health. The deal outbids Regeneron Pharmaceuticals, which offered $256M for the company last month and is pending court approval. 23andMe filed for Chapter 11 in March after privacy breaches and business struggles, falling far from its $6B peak valuation. Wojcicki says the move will allow TTAM to continue 23andMe’s original mission.

Moove, a Dubai-based startup that manages Waymo’s robotaxi fleets and finances ride-hailing vehicles, is preparing to raise $300M at a $1B valuation to expand its autonomous vehicle operations in the U.S., which would bring its total funding to $750M. The company recently reached $360M in annualized revenue, up from $115M a year ago, largely from financing Uber drivers. The upcoming raise will support the rollout of additional robotaxi depots and fuel the company's future growth in leasing fleets of autonomous vehicles to independent operators and businesses.

OpenAI is in talks with Saudi Arabia’s Public Investment Fund, India’s Reliance Industries, and existing UAE backer MGX to help complete a $40B funding round led by SoftBank, according to The Information sources. The company has already raised $10B and aims to close the next $30B by December, as it faces unprecedented capital needs to fund its growing AI operations, such as its projections of spending $90B on servers between 2025 and 2027. Completion of the funding depends on restructuring the for-profit unit, which is facing legal challenges.

Tracksuit, a New Zealand brand tracking platform that provides real-time insights into brand awareness, consideration, and perception, raised $25M in a Series B round led by VMG Partners, bringing its total amount raised to over $38M. The company helps more than 1,000 brands measure brand health metrics like awareness and preference through an AI-powered dashboard and aims to democratize brand insights once reserved for large enterprises, with plans to expand across Europe and Asia in 2025.

Try Your Best, a community-powered rewards platform that helps brands build deeper relationships with customers by offering incentives for feedback, content creation, and brand advocacy, raised $11M in a Series A round led by Offline Ventures and Strobe Ventures, bringing its total amount raised to $24M. The company currently works with 200 brands and will use the funds to onboard more brands to its platform and expand its tools.

Paynt, a Latvian payment infrastructure provider that offers embedded finance solutions for merchants, acquired E-xact Transactions, a Canadian payment processor that processes over CAD $3.5B annually, for an undisclosed amount. The acquisition will accelerate Paynt's North American expansion and aligns with the industry shift toward SoftPOS solutions, which it says will soon replace traditional POS terminals.

Payrails, a Berlin-based payments infrastructure platform that helps enterprise companies manage and scale financial operations through a unified API and orchestration layer, raised $32M in a Series A round led by HV Capital, bringing its total amount raised to $52.8M. Founded by former Stripe, Miro, and Delivery Hero execs, Payrails processed over 1M daily operations in 2024, supporting brands like Puma and Just Eat Takeaway, and will use the funds to accelerate product development and international growth following a recent Mastercard partnership.

Lemonway, a French payment institution that provides payment processing, wallet management, and compliance solutions, acquired PayGreen, a fellow French payment solution that offers eco-conscious payment processing, for an undisclosed amount to expand its presence beyond marketplaces and into broader e-commerce. The acquisition strengthens Lemonway's European position and enhances PayGreen's infrastructure and cross-border capabilities as both companies aim to offer a more complete payment ecosystem.

Pactum AI, an AI-powered negotiation platform that helps large enterprises automate commercial negotiations with suppliers, raised $54M in a Series C round led by Insight Partners, bringing its total amount raised to over $100M. The company’s AI agents use chatbots to negotiate favorable terms on supply contracts and one-time purchases, helping clients like Walmart and Honeywell cut costs and improve deal flexibility. The funding will help Pactum expand its market presence and enhance its AI offerings.

Fermàt, a New York-based commerce infrastructure startup that enables brands to create shoppable content and personalized storefronts embedded directly within social media and messaging apps, raised $45M in a Series B round led by VMG Partners, bringing its total amount raised to $75M. The funds will be used to expand its product offerings, including its Pierre Strategize AI tool, which generates customer journey strategies based on behavioral data, and Commerce Brain, a proprietary engine that tracks anonymized activity across hum and AI-driven interactions.