ChatGPT x Walmart
On the topic of career pivots, we need to talk about how Sam Altman is taking his experience running Y-Combinator (fundraising, dealmaking, allocating capital) to financial engineer OpenAI's $1T play for AI dominance.
It all starts with the fact that ChatGPT is the most important consumer AI product and AI is basically propping up the entire US economy right now: AI data centre buildout accounts for ~2% of US GDP and was responsible for ~40% of GDP growth in the first half of 2025.
With 800m weekly users, ChatGPT is gonna hit the billy club soon along with Facebook, Instagram, TikTok, WhatsApp, Telegram, YouTube and — damnit — LinkedIn.
This is 3 years after launch. Insane.
The math doesn’t look to be mathing on the financials, though. For 2025, OpenAI is projected to lose $20B on revenue of $13B while it’s committed to 26GW of AI data centers worth more than $1T.
This is why Altman is throwing Olive Garden Never Ending Pasta Bowl levels of spaghetti at the wall, per the Financial Times:
OpenAI is working on new revenue lines, debt partnerships and further fundraising as part of a five-year plan to make good on the more than $1tn in spending it has pledged to create world-leading artificial intelligence.
OpenAI is planning on deals to serve governments and businesses with more bespoke products, creating more income from new shopping tools, and new sales from its video creation service Sora and AI agents, said multiple people familiar with the start-up’s efforts.
It is also weighing ways to cash in on its intellectual property by developing new AI infrastructure, making forays into online advertising and plans to launch consumer hardware products, including a new AI-powered personal assistant device, with former Apple star designer Jony Ive.
Over the past few months, it’s clear that the market wants to believe that Altman’s high-wire act will pan out and many tech stocks have popped on OpenAI announcements:
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Oracle received a $300B data centre commitment from OpenAI (ORCL gained +36% on news)
- Shopify and Etsy were added to ChatGPT checkout feature (SHOP +6%, ETSY +16%)
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Nvidia intends to invest $100B into OpenAI (NVDA +5%)
- SK Hynix and Samsung agree to partnerships with OpenAI for advanced memory chips (SK Hynix +10%, Samsung +4%)
- AMD agreed to sell OpenAI 6GW worth of chips for AI data centers and also gave the startup warrants worth 10% of AMD (AMD +23%)
- Broadcom announced a partnership to build a custom chip for OpenAI (AVGO +10%)
The most recent major OpenAI partnership came last Tuesday: shoppers will soon be able to buy non-perishable Walmart items directly from ChatGPT.
Did Walmart’s stock pump on the news? Is the Pope Catholic?
Of course it did. The Bentonville, Arkansas retailer took Altman’s pixie dust and gained 5% to a record market cap of $850B.
It’s the latest tech move by the world’s largest seller of individual bananas (true story) to take on Amazon (which it has sharply outperformed in the past 5 years: WMT +131%, AMZN +34%):
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Walmart’s e-commerce sales hit $100B in 2024; while still short of Amazon’s $480B, WMT’s online business is growing 20% a year (vs. 10% a year for AMZN).
- Online ads were $4.4B in 2024, up 30% YoY (while less than 1% of Walmart’s total sales, high-margins on ads make it 10% of Walmart’s operating profit).
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Walmart has turned its supercenters (which usually stock 120k SKUs) into online distribution hubs (100s of millions of SKUs now).
- Wall Street is recognizing the change and Walmart’s P/E is ~40, more than that of Amazon, Apple, Meta or Microsoft (WMT has outperformed all of them in the past year).
Walmart’s digital success is bolted onto the largest real-world retail operation, per The Economist:
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“With $680B in revenue [for 2024] and 2.1m workers, it is the largest company in the world on both measures.”
- “In America it takes in a 1/10th of all retail spending, excluding cars, and a quarter of the outlay on groceries.”
- “Walmart has some 5,000 stores across America; 90% of Americans live within 10 miles (16km) of one.”
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Uses its size to get major discounts and items are 4-5% cheaper than Target (and 8-10% cheaper than other grocers).
How will Amazon respond?
The $2.3T behemoth founded by Big Daddy Bezos is actually in a tricky position. While ChatGPT is an important (and perhaps dominant future) distribution channel, Amazon has spent decades building an e-commerce walled garden and has a lot more at risk than Walmart.
Still, Ben Thompson believes the trade-off is worth it:
Now the big question is: Will Amazon follow Walmart’s lead? The answer is not obvious (and Amazon isn’t saying). Unlike Walmart, Amazon is the dominant e-commerce site, so doing anything to encourage shoppers to go elsewhere could be counterproductive. Moreover, working with ChatGPT or another chatbot would be an admission that its own AI features aren’t cutting it. (When was the last time you used Amazon’s e-commerce chatbot, Rufus?) Plus, having more shoppers search outside Amazon’s site would likely undercut its gargantuan advertising business, which is largely made up of merchants and brands paying to boost their products in search results on its website.
On the other hand, if you believe a big chunk of online shopping in the future will take place through chatbots, refusing to work with OpenAI in 2025 could be akin to refusing to let Google index your website in 2000. What’s more, if Amazon were to do a big e-commerce deal with OpenAI, it could pave the way for OpenAI to someday become a large Amazon Web Services customer, just as OpenAI has signed up to use Oracle and even Google Cloud. AWS and OpenAI took a tiny step in that direction in August, when AWS finally started offering OpenAI models to customers—more than two and a half years after ChatGPT became a household name.
Amazon has successfully navigated a similar “frenemy” relationship with TikTok—a large AWS customer but also an increasingly significant competitor in e-commerce. Though Amazon competes with TikTok in online shopping, it decided to start placing shoppable ads on TikTok. That followed an internal debate about whether doing so could hurt Amazon by further boosting TikTok’s appeal as a shopping destination, as we reported last year.
If Amazon was purely a retail company, then CEO Andy Jassy’s calculus of whether to work with ChatGPT’s Instant Checkout might be simpler. But he’s leading a huge conglomerate where what’s good for one business can hurt others. That makes it tough to handicap his final choice.
Either way, I can’t wait until OpenAI goes public and we get this announcement on CNBC.