This Week in M&A Issue #255
September 21, 2026
Happy Friday!
Today’s trend of the week is “trail running”. 🏃
Trail running is officially having a moment.
Google searches for “trail running shoes” hit an all-time high in June, while 17.2 million Americans took part in trail running in 2025. That’s a 6.6% increase from the previous year and a 57% jump since 2019.
And the spending isn’t stopping at shoes. Hydration vests have some of the highest attachment rates to trail footwear, while clothing, socks, packs, gaiters, and trekking poles are all part of the growing trail-running ecosystem.
That creates some interesting opportunities. There’s room to build businesses around trail-running gear and accessories, but also around content and niche communities that help people get into the sport.
Today we have for you:
- Amazon DSP Ads are coming to ChatGPT
- Google tests paying publishers for AI answers
And:
- eCommerce return rates by product category
- We’re giving away free tickets to Affiliate Grand Slam
- Microsoft wants businesses to turn data into Ad revenue
Alright, let’s dive in.
Amazon
Image Source: Giphy (Jimmy Arca)
Amazon Launches DSP Ad Inventory in ChatGPT
Amazon Ads and OpenAI have launched a US pilot that lets selected advertisers extend campaigns they already run through Amazon DSP into ChatGPT. The pilot launched on September 10.
Advertisers can manage campaigns through Amazon, while OpenAI controls how and where ads appear within ChatGPT.
Ads can be bought on a cost-per-click or CPM basis. Amazon is also testing product feed ads, which can automatically create ad assets using information from an advertiser’s product catalog. The ads appear beneath relevant organic ChatGPT responses and are clearly labeled as sponsored.
For advertisers, the appeal is less about adding another advertising platform and more about reaching people while they actively research and compare options. Someone planning a home renovation, for example, could encounter a relevant product ad while using ChatGPT to find DIY advice or design options.
Amazon is bringing a lot of useful data to the party. Amazon says its advertising technology can use signals from browsing, shopping, and streaming activity alongside its existing advertising relationships. That gives Amazon another way to apply its audience data outside its own properties.
There are still limitations, though. OpenAI’s ad business is relatively new, with measurement, technology, pricing, and available ad formats still developing. The Amazon partnership gives advertisers another established buying channel, but it doesn’t solve those underlying challenges.
The deal fits into Amazon’s broader push to make more premium digital inventory available through its advertising platform. Over the past 18 months, Amazon has added access to inventory across services including Netflix, Roku, Spotify, SiriusXM, Disney, Hulu and ESPN.
For now, the pilot is limited to selected US advertisers, so there’s still limited data on how the channel will perform at scale.
Google Tests Pay-Per-Value AI Licensing Scheme for Publishers
Google is testing a new way to pay publishers when their content helps power AI-generated answers.
The early-stage pilot runs through Google Search Console and pays publishers when their content makes a meaningful contribution to answers in Gemini, AI Overviews, and AI Mode. Publishers taking part get a new dashboard showing their monthly AI-related earnings, although Google hasn’t said exactly how those payments are calculated.
There’s also a gap in the data. Google’s generative AI reports show impressions from AI Overviews and AI Mode, but not clicks. The new dashboard shows earnings, but doesn’t show the data behind those payments.
So, what actually counts as a contribution?
Google pays when a publisher’s content helps shape an AI-generated answer. Simply getting a link or citation in the final response isn’t enough. In other words, Google is testing whether publishers can get paid for the information AI uses, rather than just for the traffic they receive.
Early feedback suggests the payments are still relatively small compared with traditional advertising revenue. Still, some publishers see value in getting paid directly as AI answers more questions without necessarily sending users to their websites.
Publishers can opt out at any time, and Google has reportedly approached dozens of publishers to join the program. The program has also expanded beyond traditional news organizations, with smaller and mid-sized publishers showing particular interest.
Google already has licensing relationships with more than 2,800 publications through Google News Showcase. Its separate news-focused AI program includes more than 200 titles globally.
The bigger question is whether this turns into a broader system where publishers are paid based on how much their content contributes to AI answers, instead of how many visitors that content brings in.
That could become an important new revenue stream for publishers as search becomes less dependent on sending users to websites.
eCommerce
.png)
Which eCommerce Categories Have the Highest Return Rates?
Online shoppers are far more likely to return some products than others.
New data from ECDB shows that 19.14% of fashion purchases are returned, more than twice the rate for DIY (9.4%) and electronics (9.04%). At the other end of the scale, hobby and leisure products have a return rate of just 4.51%.
Within the fashion category, apparel has a 24.22% return rate, compared with 16% for footwear and 12.91% for bags and accessories.
The main reason is fairly straightforward: you can’t try something on before buying it online. Sizing also varies between brands, so buying the same labeled size doesn’t guarantee the same fit.
Some customers also deliberately order multiple sizes or colors and return whatever doesn’t work. This practice, known as bracketing, becomes easier when retailers offer free and flexible returns.
Return rates also vary significantly by market. In the US, 31.18% of apparel orders are returned, compared with 23.75% in Germany and 23.77% in the UK. ECDB suggests that differences in return policies play a role, with generous, no-cost returns making it easier for shoppers to over-order.
For eCommerce sellers, returns can have a big impact on the numbers that matter.
A sale might look great on the dashboard, but if a significant percentage of those orders come back, the actual revenue and profit can look very different. That’s why return rate is worth tracking alongside metrics like conversion rate and average order value.
According to the NRF, US retailers are expected to deal with $849.9 billion worth of returned merchandise in 2025. Online shoppers return products even more frequently, with 19.3% of online sales expected to be returned.
For fashion businesses with high return rates, better sizing information, clearer product details, fit guidance, and more accurate descriptions can all help reduce unnecessary returns.
Read All About It!
🚀 The guide for going from 0 to $1M: Shaan Puri’s framework
🛒 Amazon confirms dates for Prime Big Deal Days: October 6-7
💡 +200 ready-to-launch business ideas: tools & frameworks
📊 Amazon Prime user and revenue statistics: data on growth, usage and more
Events
Win a Free Ticket to Affiliate Grand Slam in Rome!
We’re heading to Affiliate Grand Slam in Rome this November, and we’ve got a few extra tickets to give away.
As one of the event sponsors, we’d love to use those tickets to invite some of our customers so we can finally meet you in person.
If you’re an affiliate, ecommerce entrepreneur, online business owner, or just someone interested in joining the space, this is a great chance to spend a few days around other people building businesses online, hear from some of the biggest names in the industry, and hang out with the Empire Flippers team.
And the best part? Your conference ticket is on us.
If you’re going to be in Rome anyway, come say hi. And if you weren’t planning on going, this might be your excuse.
Good luck!
Please note: The giveaway covers the Affiliate Grand Slam conference ticket only. Travel to and from Rome, accommodation, meals, and any other personal expenses are not included and are the responsibility of the winners.
Ads
Microsoft Wants More Businesses to Monetize Their Data
Businesses that own valuable data, content, audiences, or ad inventory may have another way to make money from those assets.
Microsoft is pushing the idea of media curation, where businesses package their own data and media assets into advertising products that brands can buy programmatically.
According to Microsoft, nearly 70% of real-time bidding advertising, worth around $52 billion a year, now runs through private marketplace deals. These deals give advertisers more control over where their ads appear and the data used to target them.
The opportunity for businesses is to go beyond simply selling ad space. They can combine first-party data, audience insights, contextual signals, and premium inventory into curated advertising packages.
Microsoft’s Microsoft Curate platform is built around this idea. It lets businesses bring together audience activation, inventory, forecasting, campaign optimization, measurement, and reporting in one workflow. Their curated deals can then be made available to buyers through major third-party demand-side platforms.
Microsoft says one customer simplified their ad setup by reducing 250 line items to just 14 after moving to curated deals, cutting down the amount of work needed to manage campaigns. Data-enriched private marketplace deals can also produce 1.5x to 3x higher click-through rates and 10% to 30% higher video completion rates than open exchanges.
Microsoft says its platform uses Copilot and Model Context Protocol so users can ask questions about campaign performance, deals, reporting, and account changes using natural language.
Essentially, a retailer, publisher, data company, or other business may already have assets advertisers want. Instead of just using those assets internally, they can package them into products that other companies are willing to pay for.
For businesses with strong first-party data or specialized audiences, that could turn existing assets into a new source of advertising revenue.
Money Nomad
Looking for a side hustle?
Try Money Nomad, our sister marketplace built specifically for profitable side hustles and micro-businesses that are too small for Empire Flippers.
Check out this recent listing available on the Money Nomad Marketplace:
Listing #10178 – $108,000.00
ecommerce | home, culinary
Elaran is a turnkey Shopify store selling kitchen and home essentials, generating $24,700 in monthly revenue and $6,631 in profit after just 2 months. The business includes 3 months of coaching and ad management support, plus validated products with 59% gross margins and a proven Meta ads playbook. Learn More
Subscribe to the This Week in M&A Newsletter
to Get Content like This in Your Inbox Every Friday
