Always wanted a personal shopper? Get ready to let ChatGPT do the buying. OpenAI recently added “instant checkout” to its chatbot, letting users buy crochet keychains and pet portraits from Etsy merchants. Soon, it’ll also add Shopify’s 1 million sellers, which include retailers like Glossier and Vuori.

That means ChatGPT users can now go from asking, “What’s a good gift for a pet lover?” to purchasing a pet portrait without leaving OpenAI’s platform.

As AI platforms take the place of search engines, a move into shopping could further upend the established tech order.

AI’s On a Shopping Spree

OpenAI’s new all-in-one-place shopping experience cuts marketplaces like Amazon and Google Shopping out of the equation, connecting users directly with brands. Amazon and Google have used their dominance in the past to promote the products of their choosing, and now OpenAI will have that power. For now, though, OpenAI says its product recommendations are “organic and unsponsored.” It charges a small fee to merchants when a purchase is completed. Stripe, which helped create the agentic checkout protocol, said it’s making “the economic infrastructure for AI.”

For OpenAI, earning fees from facilitating shopping sprees could become a new revenue source. OpenAI may be the world’s most valuable private company, but it hasn’t turned a profit and has burned through billions of investor dollars building and running its AI models.

Despite having an estimated 700 million weekly active users, ChatGPT also has stiff competition in agentic shopping:

• Perplexity, an AI search engine, introduced a shopping feature last year that, similar to OpenAI’s, allows customers to check out directly on the platform without switching tabs. Microsoft’s AI platform, Copilot, also lets merchants operate stores directly in chats with shoppers. A handful of startups, including Daydream and Deft, have raised millions to build AI-powered shopping solutions.
• But the old guard of retail doesn’t want to be left in the dust: Amazon rolled out an AI assistant last year that it said has helped recommend products to millions of shoppers, and Google has AI-ified its Shopping tab with personalized recommendations.

Double-Edged: While Etsy said the integration will help new users discover its merchants and buy their handmade trinkets, shopping on ChatGPT could ultimately hurt the retailers it features. They lose control over curating and promoting products, and may have a harder time building a loyal customer base when those customers have never been on their site.

For the first time in a decade, McDonald’s is bringing back its ultra-popular Monopoly promotion. Fittingly, the company is also in the midst of its own mad dash to snap up real estate on Boardwalk, Park Place and just about everywhere else.

In an interview with Bloomberg last week, Chief Development Officer Tabassum Zalotrawala said the company is on a mission to open 10,000 new locations over the next four years, bringing its worldwide total to 50,000. That will make one of the world’s most ubiquitous restaurant chains more, well, ubiquitous.

The Sun Never Sets on the Golden Arches

Through the past few years of widespread inflation, McDonald’s has been locked in a no-holds-barred Value Menu War against its fast-food brethren. But that has only sparked an internal battle between McDonald’s franchise foot soldiers and their corporate generals, with the former saying their profits are getting crushed by the latter’s push for exorbitant discounts and promotions. (In August, the two sides reached a treaty, agreeing to sell eight popular combo meals at a 15% discount to usual prices, according to a report in The Wall Street Journal.)

Last year, a survey from the UBS Evidence Lab found that the number of fast-food customers who would describe McDonald’s as having “good value” fell to its lowest point in 10 years. Same-store sales growth slowed to its lowest rate in a decade in 2024.

The only way out? Expand. And the best way to expand? Follow the people:

• In choosing its new locations, Zalotrawala says McDonald’s will focus on regions where it has fallen behind population growth in recent years; for instance, one-fourth of the new locations are planned for Texas, where 2 million people have moved since 2020.
• The strategy, which is in keeping with its 1970s jingle, “We Do It All for You,” is a marked turnaround for the Golden Arches, whose total number of US locations declined by over 900 from 2015 to 2021. The expansion comes after McDonald’s last year increased royalty fees from 4% of gross sales to 5% for new franchise owners in the US and Canada.

Starburst: At 50,000 locations, McDonald’s should return to being neck-and-neck with rapidly expanding Chinese beverage chain Mixue Ice Cream & Tea, which exploded from 21,000 locations to a world-leading 46,000 locations from 2021 to 2024. One chain you won’t be seeing more of is Starbucks, which spent the summer closing hundreds of stores amid new CEO Brian Niccol’s $1 billion cost-restructuring plan. If your favorite Starbucks is closing, fear not: We’re sure the one right around the corner is still open. Hopefully.

Recent weeks have seen a pickup in noteworthy US-listed initial public offerings, with fintech Klarna, ticket reseller StubHub and cybersecurity firm Netskope among the slew of high-profile IPOs that Wall Street hopes signal a bumper fall.

But the IPO market isn’t likely to party again like it did in 1999. A years-long slump in listings, due to an appetite first dented by high interest rates and inflation and more recently by tariff uncertainty, is just the tip of a much bigger iceberg. And hopes for a return to the record IPO days of 2021, even if macro conditions become more favorable, must contend with the fact that life as a private company is more comfortable than ever.

Not the Smoking Gun

The declining trend in IPOs dates back much farther than the latest cold streak. In the late 1990s, approximately 8,000 US companies were listed on stock exchanges. Today, estimates say the number is about half of that. One factor that has taken a considerable portion of the blame is the supposedly onerous burden of government regulations that come with listing. It’s a claim executives have been keen to amplify, arguing that compliance with disclosure and regulatory requirements is costly and discourages firms from going public.

However, Columbia Business School researchers found that regulatory costs account for only 7.3% of the decline in IPOs over time. Even if you got rid of all post-2000 regulatory costs, they determined, the decline in publicly listed companies would be relatively unchanged. The more obvious explanation, they noted, is the massive expansion of available private funding from venture capital and private equity. “Firms are staying private because they can now in ways that they couldn’t before,” noted Michael Ewens, a Columbia finance professor who co-authored the research. “They can raise money at crazy valuations and not worry about running out and having to tap the public markets.” Analysts also anticipate private equity will outperform public markets in the years ahead:

• Last year, Bain & Company forecasted that private market assets would grow at more than twice the rate of public ones, reaching as high as $65 trillion globally by 2032.
• “The public market is disappearing, and it’s concerning, but regulatory cost isn’t the smoking gun,” said Kairong Xiao, a Columbia business professor and Ewen’s co-author. The researchers warned that, if high-growth companies continue to stay private longer, the broader public investor class could be shut out of gains reserved for venture capital, private equity and other major investors with an inside track.

Chatbot Riches: OpenAI secured a $500 billion valuation last week when it completed a deal that allowed current and former employees to sell $6.6 billion worth of stock to investors. It now ranks above SpaceX ($400 billion), ByteDance ($330 billion), and Anthropic ($183 billion) as the world’s most valuable private company.