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Sorry, mom. The shopping bots suggested a bathrobe for Christmas

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Amazon’s AI-infused Rufus shopping assistant has new features that make it a “faster, more useful, state-of-the-art shopping companion.” Google’s agentic checkout feature “can do the heavy lifting to help you get the perfect item without blowing your budget.” OpenAI on Monday unveiled a free ChatGPT tool it says can generate a personalized gift-buying guide.

New artificial intelligence shopping tools are sprouting right and left just in time for the holidays, when US consumers are expected to spend a record $253 billion online. Technology companies and retailers are rushing to get ahead of a shift in consumer behavior that prognosticators say will one day see people using autonomous agents to research, price and buy products rather than plugging queries into a search engine.

E-commerce hasn’t changed all that much over the past 20 years, and there are signs people are itching for something new. More than 1 in 3 US consumers said they have used AI tools to assist in online shopping, mostly for product research, according to a September survey conducted by Adobe Inc. And the consulting firm McKinsey & Co. forecasts that so-called agentic commerce — a rubric for automated agents aiding purchases or handling transactions entirely — could explode into a $1 trillion business in the US by 2030.

McKinsey could be right, but for the time being, agentic commerce is in an awkward experimental phase, with companies struggling to solve various technical challenges and negotiate partnerships even as they push out a variety of tools and features to see what works and what doesn’t.

Bloomberg asked several AI bots — including Amazon’s Rufus, OpenAI’s ChatGPT and Walmart Inc.’s Sparky — what to buy mom for Christmas. The top suggestion: a cozy bathrobe. Sparky recommended a pink hooded number emblazoned with “Mama Bear,” and ChatGPT suggested buying the robe from Victoria’s Secret. Perplexity Inc.’s AI bot proffered another option found on many gift guides: a $20 wooden photo frame from Etsy.

“There are a lot of really big bets being made right now that consumers want to shop differently and that chat is the way they want to start shopping,” said Emily Pfeiffer, an analyst at Forrester Research Inc. “I don’t think this is going to have a huge impact on the way we shop this holiday season.”Play Video

The appeal of AI-aided commerce is obvious. Navigating through millions of products on Amazon, Walmart, Etsy and other retailers can be a tedious process that involves checking desired feature boxes, combing through reviews and scrolling through one advertisement after another. Telling a chatbot to “Find me a pair of well-reviewed hiking boots in my size, under $100, and available for delivery or pickup by Friday,” seems like a much more user-friendly and intuitive experience. And there are early indications that shoppers referred to a website following a conversation with ChatGPT are more informed and prepared to buy than those who conducted a typical Google search, according to Similarweb Ltd., which monitors website traffic and app use.

But for the most part, bots haven’t yet meaningfully improved shopping. Amazon Chief Executive Officer Andy Jassy recently gave rivals’ technology a mixed review, noting that agents aren’t very good at tailoring shopping to individual consumers and often display incorrect pricing and delivery estimates.

Retailers’ websites — built to be browsed by humans poking around with clicks and eyeballs — have added machine-readable interfaces over the years for automated tools like web-crawling robots, or for partners to manage inventory. But they weren’t designed to hand off purchasing authority to third parties. That’s why many shopping chatbots essentially grab product listings and then present a user with a web link to buy on that retailer’s site — not much of an advancement over the way things have been done for years.

Bot makers are working to solve various technical challenges. Anthropic PBC and Alphabet Inc.’s Google, for example, have built protocols designed to referee how agents communicate, helping translate queries made in human language into something capable of navigating a catalogue. Microsoft Corp. earlier this year announced a set of tools that helps retailers and other companies translate their websites to a medium agents can more readily interact with. Companies are also working with AI models, backed by immense computing power, that can understand what’s rendered on a web browser and click through menus to make an order.

As with any AI tool, efficacy depends largely on the data it feeds on. Retailers, keen to retain a competitive edge over rivals, have long guarded customer information like purchase history and customer reviews that bots could scrape to improve the shopping experience. Amazon, which captures about 40 cents of every dollar spent online in the US, has maintained a walled garden and doesn’t currently permit autonomous shopping on its site. In a warning shot that could have implications for agentic shopping,  the e-commerce giant recently sued Perplexity to try and stop the startup from helping shoppers buy items on its marketplace.

Letting in Perplexity and others could damage Amazon’s advertising business, which is expected to generate almost $70 billion this year by persuading shoppers to click on ads while searching for products. Amazon is developing its own shopping bots. Rufus, launched in February 2024, can browse Amazon’s site, recommend products to shoppers and put them in a cart. In April, the company also introduced a feature — still in public testing — called Buy For Me, which is designed to let shoppers purchase items from other retailers’ sites in the Amazon shopping app.

Walmart has shown itself more willing to work with outside companies. The chain in October said shoppers would be able to purchase apparel, electronics, packaged food and other products directly on ChatGPT by pushing a buy button. The feature is rolling out in stages and is initially limited to single-item purchases, not how shoppers typically buy from the world’s largest retailer.

Partnerships with big retailers and payments processors will be crucial for the likes of OpenAI and Perplexity to become serious players in shopping. The ultimate goal is to let users browse and buy directly in their apps without having to leave. Perplexity this week announced it was incorporating PayPal checkout options into its offering.  Without giving people an easy way to buy things, the AI startups will be limited to conducting research, said Juozas Kaziukenas, an independent e-commerce analyst.

“It reminds me of searching online for a recipe and you end up on a website that wants you to read a 10,000-word family story before it tells you what you need to make a meatloaf,” he said. “For some queries, ChatGPT will just throw up a wall of text on you. We have to see how this morphs into something that’s cool to use.”

In Bloomberg’s gift-for-mom experiment, Amazon’s Rufus was the only bot that tried to learn more before answering. It asked about her interests and hobbies as well as the price range. After learning that mom is a fan of classic films, Rufus suggested a DVD set of movies starring Spencer Tracy and Katharine Hepburn.

OpenAI is moving in a similar direction with its latest shopping tool. It asks clarifying questions and draws its answers from reviews published on  websites, such as Reddit, which the company said may be considered more trustworthy than paid marketing or reviews posted on a product page. Users can use a dedicated “shopping research” button in the chat interface and describe what they’re looking for using instructions like “find a small couch for a studio apartment” or “I need a gift for my 4-year-old niece who loves art.”

Instead of immediately generating a text response, the research tool will ask for more information in a quiz format, taking into consideration possible factors such as budget, color preferences and the desired size of the item. As it gathers information from the web, it will suggest 10 to 15 items along the way, and users will be prompted to click “more like this” or “not interested” to refine the final list. 

In a reminder that shopping bots are a work in progress, OpenAI recommended that users visit merchant sites for the most accurate details and cautioned that the new tool “might make mistakes about product details” including price and availability.



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What a Walmart CEO contender’s exit reveals about when to move on

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There’s no such thing as a silver medal in a CEO succession race.

In November, Walmart named U.S. chief John Furner as its next CEO, crowning him the sixth leader in the history of the world’s largest retailer. The decision also quietly closed the door on another highly regarded contender for the corner office: Kath McLay, Walmart International’s CEO and a decade-long veteran of the company. On Thursday, Walmart disclosed that McLay would depart, staying on briefly to ensure a smooth transition.

The sequence was swift, orderly, and entirely unsurprising to those who study corporate succession. Boards rarely say it out loud, but experienced executives understand intuitively that once a CEO is chosen, the long-term prospects for previously whispered-about internal candidates dim almost immediately as power consolidates around the new chief executive. 

That’s why many of the most ambitious leaders in American business don’t linger after a succession decision. They move deliberately, and often quickly, because the moment immediately after a board makes its choice is paradoxically when a near-CEO executive’s market value is at its peak. The executive has just been validated at the highest level—close enough to be seriously considered for the top job—without yet absorbing the reputational drag that can follow prolonged proximity to a decision that didn’t go their way.

In that narrow window, the story is still about capability. Search firms and directors see a leader who was trusted with scale, complexity, and board scrutiny, not someone who failed to clear the final hurdle. 

When Jeff Immelt was named CEO of General Electric in 2001, the decision concluded one of the most closely watched succession contests in modern corporate history. Among the executives developed as credible successors was Bob Nardelli, then president and CEO of GE Power Systems. Nardelli didn’t stay to see how it might play out. Within months, he left GE to become Home Depot’s CEO.

A decade later, a different scenario unfolded at Apple, but with a similar outcome. Retail chief Ron Johnson had transformed Apple’s stores into an industry-defining, highly profitable global business and was widely viewed internally as CEO-caliber. Apple’s board had long centered its succession plans on Tim Cook, and when Cook was formally named successor to Steve Jobs, it effectively closed the door on a CEO path for Johnson. He left soon after to take the top job at J.C. Penney.

The executives who leave quickly aren’t being disloyal; they’re being realistic. Remaining too long after a succession decision can quietly erode an executive’s standing, both internally and externally, as the narrative shifts from “next in line” to “still waiting.”

At Ford Motor Co., president Joe Hinrichs was widely viewed as a leading CEO contender. When the board selected Jim Hackett in 2017, Hinrichs left not long afterward. Five years later, he resurfaced as CEO of transportation company CSX. Similarly, several senior Disney executives left or were sidelined after Bob Chapek was chosen as CEO in 2020. Most notably, Kevin Mayer, Disney’s head of direct-to-consumer and international, and a widely assumed CEO contender, departed within months to briefly become CEO of TikTok.

There are exceptions. But they tend to follow a different arc.

Although longtime Nike insider Elliott Hill was not passed over in a formal succession contest, he was widely viewed as CEO-ready when the board opted for an external hire in 2020. Hill stayed on for several years and later retired. Only after performance pressures mounted and the company embarked on a strategic reset did Nike’s board reverse course, asking Hill to return as CEO in 2024. Even then, such boomerangs remain exceedingly rare.

McLay’s departure from Walmart fits the dominant pattern. By exiting promptly while remaining to support a defined transition, she preserves both her reputation and her leverage. She leaves as an executive who was close enough to be seriously considered—not one who stayed long enough to be diminished by the process.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.



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Crypto market reels in face of tariff turmoil, Bitcoin falls below $90,000 as key legislation stalls

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If you don’t like the price of Bitcoin, wait five minutes, and it will change. The major cryptocurrency’s volatility has been on full display to start the year, this time dipping about 7% since last week to its current price of just under $90,000 as of mid-day Tuesday.

Other cryptocurrencies have also slid. Ethereum is down 11% in the last six days to its current price of about $3,000, and Solana is down about 14% during that time to its price of about $127. 

The dip comes as President Donald Trump threatened European nations with tariffs as they pushed back against his plans to take over Greenland, causing markets to scramble. Meanwhile, crypto markets faced an additional headwind as key legislation for the industry, known as the Clarity Act, became stalled after industry giant Coinbase unexpectedly withdrew its support late last week. 

“President Trump’s threat to impose tariffs on Europe has put Bitcoin under pressure,” said Russell Thompson, chief investment officer at Hilbert Group. “The postponement of the Clarity Act in the Senate committee mainly due to concerns from Coinbase eliminated a large amount of positive sentiment in the market.”

Coinbase CEO Brian Armstrong objected to the Clarity Act primarily on grounds that crypto owners would not be able to earn yield from stablecoins. The new uncertainty over the bill, which many assumed was on a smooth path towards a Presidential signature, has shaken the price not just of crypto assets but also the share price of companies exposed to digital assets. 

It’s uncertain whether the current headwinds will fade anytime soon. Trump has made his intentions of taking control of Greenland clear. When a group of European nations expressed solidarity with the Danish, he threatened those countries with tariffs, saying he would not back down until Greenland was purchased. Bitcoin and other risk assets subsequently fell, along with major stock indices, while the price of gold rose.

It’s not all gloom and doom for crypto, at least according to some analysts, who view Bitcoin’s correlation with macroeconomic forces as confirmation that digital assets have finally gone mainstream. 

“Bitcoin’s reactivity is another sign of its increasing integration with broader macroeconomic forces, signaling maturation rather than fragility, even as short-term volatility continues,” said Beto Aparicio, senior manager of strategic finance at Offchain Labs.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.



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The 9 most disruptive deals of Trump’s first year back in the White House

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President Trump lives on deals: “That’s what I do—I do deals,” he once told Bob Woodward. On the one-year anniversary of his second presidency, he’s pushing hard to make his biggest, most disruptive deal ever, one that would bring Greenland under the control of the U.S.—and the global business community is still scrambling to adapt to his approach. Here are nine of Trump’s most unorthodox deals from the past year.

Nine deals that shook the business world

April 2, 2025: Reciprocal tariffs

Trump imposes “reciprocal tariffs” on 57 countries, with each tariff understood as an opening bid in a negotiation. Several countries have since made deals. The one-on-one negotiations, unlike the multilateral system of the past 80 years, can be chaotic for companies and economies

June 13: U.S. Steel “Golden Share”

In return for allowing Nippon Steel to buy U.S. Steel, Trump requires that the U.S. receive several powers over the company, including total power over all the board’s independent directors and vetoes over locations of offices and factories. 

July 10: MP Materials

The U.S. pays $400 million for a large equity share in MP and signs a contract to buy all of MP’s rare earth magnets for 10 years. The reason for the equity stake was not disclosed.

July 14: Nvidia, Part 1

JADE GAO—AFP/Getty Images

Trump reverses the U.S. ban on selling Nvidia H20 chips to China in exchange for Nvidia paying the U.S. 15% of the revenue.

July 23: Columbia University

LYA CATTEL/Getty Images

The Trump administration restores $400 million of canceled federal research funding for the university under an unprecedented multipoint deal. For example, Columbia must supply data to the federal government for all applicants, broken down by race, “color,” GPA, and standardized test performance. A few other schools later make similar deals.

August 6: Apple

Bonnie Cash—UPI/Bloomberg/Getty Images

At a public appearance with Trump, CEO Tim Cook announces Apple will invest an additional $100 billion in the U.S. over four years; Trump announces Apple will be exempt from a planned tariff on imported chips that would have doubled the price of iPhones in the U.S.

August 22: Intel

Justin Sullivan—Getty Images

Intel trades the U.S. government a 9.9% equity stake in exchange for $8.9 billion that might already be owed to Intel under the CHIPS and Science Act. The deal is unusual because the company was not in immediate danger or significantly affecting the economy.

December 8: Nvidia, Part 2:

Trump reverses the U.S. ban on selling powerful Nvidia H200 chips in exchange for Nvidia paying the U.S. 25% of the revenue. Both Nvidia deals are unusual because the payments to the U.S., based on exports, appear to be forbidden by the Constitution. 

December 19: Pharma

Alex Wong—Getty Images

Nine pharmaceutical companies make deals with Trump that are intended to lower drug prices. This is unusual because Trump negotiated separate deals with each company, and the terms have not been released.

All eyes this week will be watching President Trump at the World Economic Forum in Davos, where the president has hinted he’ll announce some high-stakes agreements. Expect the unexpected.

A version of this piece appears in the February/March 2026 issue of Fortune.



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