This Week in M&A Issue #221

Lauren Buchanan January 26, 2026

TWIMA #221

Aloha!

Today’s trend of the week is “weighted walking ”. 🚶

What if your daily walk could double as a workout?

That’s the promise behind weighted walking, often called rucking. Instead of squeezing in a separate workout, people are strapping on weighted vests for neighborhood walks, hikes, and even casual strolls. It’s simple, accessible, and increasingly popular.

From May 2024 to May 2025, weighted vest sales jumped more than 50% to $27 million, according to Circana. Search demand is climbing just as fast, with Google searches for “weighted walking vest” up 149% year over year and 93K searches in the last month alone.

For online business owners, this momentum opens the door to more than just selling vests. Accessories, adjustable weight systems, comfort-focused designs, educational content, injury-prevention guidance, and even niche communities all fit naturally into this growing ecosystem.

Today we have for you:

  • OpenAI prepares to introduce Ads into ChatGPT
  • Amazon new seller registrations hit a ten year low

And:

  • Shopify launches UCP to bring AI shopping to every brand
  • Sell your business at a premium by understanding buyer financing
  • Debunking the myth that SEO traffic has collapsed

Alright, let’s dive in.

AI

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Image Source: Giphy

OpenAI Brings Ads to ChatGPT, Opening a New Channel for Advertisers

After months of speculation about how OpenAI plans to make money, the company has confirmed it will begin testing limited, targeted ads inside ChatGPT. The rollout is expected to start in the coming weeks and opens a potential new channel for marketers to reach ChatGPT’s enormous audience of more than 700 million weekly users.

The initial test will be limited to the United States and will apply only to users on the Free and Go tiers. Go is OpenAI’s new $8 per month plan, which launched globally this week. Higher priced plans including Plus, Pro, Business, and Enterprise, will remain ad-free.

This marks OpenAI’s first official step into advertising, placing it closer to competitors like Google and Microsoft, which already earn billions from AI-powered ads. According to OpenAI, ads will appear at the bottom of conversations and will be tied to the topic being discussed. A user chatting about travel, for example, might see a related travel ad.

OpenAI says users will retain meaningful control. Ads will be clearly labeled as sponsored, visually separated from answers, and easy to dismiss. Users will be able to see why an ad is shown and can turn off ad personalization entirely. Ads will not be shown to users under 18 or alongside sensitive topics such as health, mental health, or politics.

The company also stresses that advertising will not influence ChatGPT’s responses. OpenAI refers to this as “answer independence” and says it will not sell user data to advertisers.

Google, meanwhile, is taking a different approach. Speaking at the World Economic Forum in Davos, Google DeepMind CEO Demis Hassabis said there are no plans to bring ads to the Gemini app. While Google continues to run ads across Search and other AI features, Gemini itself is positioned as an ad-free assistant, highlighting a clear divide in how the two companies are approaching AI monetization.

The Opportunity podcast

Sell Your Business at a Premium by Understanding Buyer Financing [Ep.202] (1)

From Buyer to Builder: Scaling Through Digital Business Acquisitions

When many entrepreneurs go to sell their business, they’re more focused on their business than on the buyer.

Understanding how buyers approach an acquisition, particularly when it comes to funding and deal structure, can help you position your business for the most profitable exit.

In this podcast episode, Greg explains how buyer financing, SBA loans, and deal structure impact your business exit and final sale price.

He also covers common mistakes that cause deals to fall apart, how seller financing and earnouts can be used to close stronger deals, and why setting up a US entity can significantly improve exit outcomes.

If you are planning to sell your business now or in the future, this episode will help you think like a buyer and position your business to be easier to finance, more attractive to buyers, and more likely to sell at a premium.

amazon

Fewer Sellers Join Amazon as Opportunities Shift

Amazon is no longer the playground it used to be for casual side hustlers.

According to Marketplace Pulse, in 2025, new seller registrations fell to just 165,000, the lowest in a decade and a 44% drop from 2024, indicating a shift toward more seasoned, well-funded operators.

Analysts are calling this change the Great Compression. Sellers face higher tariffs, overseas competitors taking advantage of enforcement gaps, and rising expectations driven by AI. Advertising costs are now mandatory for visibility, platform fees are up, and Chinese sellers make up over half of all active accounts. Together, these factors discouraged new sellers from signing up.

Interestingly, even as seller numbers fell, from 2.4 million in 2021 to 1.65 million in 2025, the opportunity for remaining sellers has grown.

Amazon’s third-party U.S. sales hit $305 billion, with global sales reaching $575 billion. Traffic per active seller increased 31% since 2021, and the number of sellers generating over $1 million annually rose from roughly 60,000 to over 100,000. Those earning $100 million or more jumped from 50 to 235.  Sellers who can master Amazon’s complexities and scale strategically are reaping big rewards.

The profile of new sellers is changing too. Chinese sellers accounted for 59.9% of 2025’s new registrations, slightly down from 62.3% in 2024, likely due to stricter tax reporting. American sellers made up just 16.3%, continuing a long-term decline.

For anyone thinking of starting on Amazon, casual, part-time operations face steep challenges. Success now requires capital, strategy, and the ability to handle fees, tariffs, and stiff competition. Sellers who want to thrive must operate at a more professional level from day one.

Read All About It!

🔥 The hottest business to start in 2026: it’s not an AI business

💡 Simple, niche businesses that are making millions: ideas to copy in 2026

🏷️ Shopify merchants to pay an extra 4% fee on ChatGPT sales: from 26 Jan

📦 Amazon CEO says tariffs are driving up product prices: sellers absorbing costs

Agentic Commerce

Shopify Launches Universal Commerce Protocol to Transform AI Shopping

AI chats are quickly becoming a place where consumers search for products, compare options, and make buying decisions. Shopify’s goal is to ensure merchants can sell wherever those conversations happen with the launch of the Universal Commerce Protocol, or UCP.

With UCP, Shopify merchants will soon be able to sell directly inside Google Search AI Mode and the Gemini app, using native checkout experiences managed from the Shopify Admin. Shopify is also expanding its Microsoft Copilot integration with a new embedded checkout that allows purchases to happen directly inside Copilot.

UCP is designed to work across platforms and accommodate the many ways businesses sell online. It supports key checkout steps like applying discount codes, selecting subscriptions, confirming loyalty details, and handling preorders or final sale terms. The protocol works with any payment processor and gives AI agents a clear framework to complete purchases or request additional information from shoppers when needed.

A major change is Shopify opening its Catalog to all brands through a new Agentic plan. Businesses no longer need a Shopify storefront to sell through AI channels.

Brands on any platform can now use Shopify’s infrastructure to list products once and have them appear across AI tools like ChatGPT, Google AI Mode, Gemini, and Microsoft Copilot. Shopify’s catalog uses AI to standardize and enrich product data so items surface more accurately during discovery.

For small business owners, the opportunity is significant, but it comes with challenges. Adopting AI-driven sales channels may require new skills, better product data, and careful attention to security and integration.

Overall, Shopify’s Universal Commerce Protocol signals a future where AI plays a central role in retail. Businesses that adapt early are likely to be better positioned to reach customers, stand out in crowded markets, and grow as shopping continues to evolve.

seo

Organic Search Remains Strong Despite AI Growth

Despite widespread claims that SEO is losing relevance, new data shows that organic search traffic remains largely stable.

According to a large-scale analysis by Graphite, which examined Similarweb data from over 40,000 of the largest U.S. websites, organic search traffic declined just 2.5% year over year, far from the 25% to 60% drops often cited in industry discussions.

The study challenges the notion that AI tools like ChatGPT are rapidly replacing traditional search. While AI-generated “Overview” panels do reduce click-through rates, their impact is smaller than many assume. These panels appear in about 30% of searches, primarily for informational queries, and have minimal effect on commercial or transactional keywords.

Traffic trends vary by site size. The largest websites, including the top 10, saw a 1.6% increase in organic traffic. Declines were mainly seen among mid-sized publishers ranked between 100 and 10,000. Google’s own statements align with these findings, noting that total organic click volume has remained relatively stable year over year.

Paid search also has not drastically shifted the landscape. Organic results still account for roughly 90% of clicks, compared with about 10% for ads. While paid ad clicks have risen slightly, the change is modest and does not signal a collapse of organic traffic.

Graphite’s analysis relied on Similarweb estimates, combining user panels, ISP and mobile data, public web signals, and direct site measurements. The findings were validated against first-party Google Search Console and Google Analytics data, showing a strong correlation of 0.86.

Experts say the key takeaway is that SEO is evolving rather than disappearing. Search engine results pages now feature more AI-driven answers and diverse content formats, fragmenting the traffic that used to flow to traditional listings. This makes strategic SEO more important than ever, as competition for clicks grows.

Money Nomad

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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 M20134 – $20,000.00

ecommerce | Retail & Wholesale

WearWood is an established brand that sells wooden sunglasses through its Shopify website and wholesale partners. The business has strong gross margins (about 75% retail, 50% wholesale) and previously generated up to $6,000/month in profit. All sales over the past several years have been organic or repeat customers — no paid ads or outbound efforts. There’s over $50,000 in retail-value inventory included, along with supplier relationships, a 2,300-subscriber email list, and existing wholesale accounts. The brand has a loyal customer base, excellent reviews, and a unique eco-friendly angle: two trees are planted for every pair sold. This is a turnkey operation ready for a buyer who wants to scale it through marketing, wholesale outreach, or expansion onto marketplaces like Amazon. Learn More

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