The Promise and Peril of Sam Altman’s Dealmaking

Summary

WSJ Tech News Briefing – “The Promise and Peril of Sam Altman’s Dealmaking”

Date: October 24, 2025
Host: Belle Lin
Guests: Jinju Lee (WSJ Columnist), Berber Jin (WSJ Tech Reporter)

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Overview

In this episode, WSJ Tech News Briefing delves into the seismic impact of OpenAI’s evolving business strategies—focusing on novel features like Instant Checkout in ChatGPT and the high-stakes global dealmaking of CEO Sam Altman. The episode explores both the opportunities and risks these changes pose for retailers and the tech sector at large, highlighting how Altman’s maneuvers are reshaping the business landscape around AI infrastructure and investment.

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Key Discussion Points & Insights

1. OpenAI's Instant Checkout Feature and Retail Impact

Guest: Jinju Lee
[00:19–04:59]

• Instant Checkout Launch
  • OpenAI released “Instant Checkout,” enabling purchases directly within ChatGPT.
  • Example use case: Ask ChatGPT for recommendations, purchase items without leaving the chatbot.
• Retailer Benefits

  • Early adopters (like Walmart) gain a potential first-mover advantage.

    “If you are a retailer that's available on ChatGPT for instant checkout… you would have the first mover advantage there.”
    — Jinju Lee [01:56]

  • Convenience may sway customers to choose items available via Instant Checkout.

• Retailer Concerns

  • Frictionless shopping threatens customer loyalty and on-site traffic.

  • Reduced site traffic could dent ad revenue—a significant profit center for retailers.

    “If enough people start using instant checkout on ChatGPT … that could potentially dent customer loyalty. And if there is less traffic on retailers websites, that could also hurt retailers ad revenue…”
    — Jinju Lee [02:41]

• Protecting Customer Relationships
  • Limiting available products in ChatGPT (e.g., Walmart excludes fresh produce).
  • Developing proprietary AI shopping tools to compete with universal platforms.
• Amazon’s Cautious Approach
  • Amazon has not joined Instant Checkout, blocks external AI tools from scraping product data.
  • Focuses on its own AI systems as well as protecting its large ad business.

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2. Sam Altman’s Dealmaking: Vision, Risks & Industry Impact

Guest: Berber Jin
[06:02–11:16]

• Strategic Context
  • Sam Altman ties OpenAI’s fate to cloud and chip giants through aggressive dealmaking.
  • Key partnership: Attempted “Stargate” $500 billion data center initiative with Masayoshi Son (SoftBank).
    • Announced at the White House, ultimately scaled down but catalyzed further deals.
    • Demonstrated Altman’s playbook: bold, public moves to build momentum.
• Deal-Making Tactics

  • Altman thrives on creating FOMO (fear of missing out) among major tech leaders and investors.

  • Pits suppliers (Nvidia, Broadcom, AMD, etc.) against each other for exclusive deals.

    “…he's having them compete against one another, right, to build the best chip for OpenAI.”
    — Berber Jin [08:06]

  • Switches between partners to drive up offers—leveraging Microsoft and Oracle, for instance.

    “…he just found someone else. And we've reported that now Microsoft is considering giving OpenAI more computing capacity.”
    — Berber Jin [08:06]

• OpenAI’s Financial Uncertainty

  • OpenAI is on track for $13 billion in annual revenue but faces up to $650 billion in partner obligations.

  • Altman’s answer: Bet on continued exponential revenue growth and seek novel financing strategies, including getting suppliers to help fund expansion.

    “Altman has alluded coyly to some new financing strategies he's developing…”
    — Berber Jin [09:52]

• If the Growth Falters

  • The entire tech sector could face repercussions if OpenAI’s growth slows—elevating risk for investors and industry partners heavily tied to Altman’s vision.

    “It's very plausible to see a big sell off in tech stocks. And he's tying the fates of a lot of the biggest cloud and chip companies to OpenAI.”
    — Berber Jin [10:39]

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Notable Quotes & Memorable Moments

• On Pressure for Early Adopters:
  • “If you're a shopper and you see two similarly priced things listed on ChatGPT, and on one of them you can click immediately to checkout, maybe you're more inclined to go for that option.”
    — Jinju Lee [01:56]
• On High-Stakes Risk:
  • “At the time... all these big CEOs like Dario Amade at Anthropic and Satya Nadella and Elon Musk were saying they don't have the money, they have no idea what they're doing. And they weren't entirely wrong… that effort didn't really go anywhere.”
    — Berber Jin [06:39]
• On Investor Anxiety:
  • “...it's this kind of surreal effect where essentially investors expectations around AI are growing larger and larger… if OpenAI doesn't, ... it's very plausible to see a big sell off in tech stocks.”
    — Berber Jin [10:39]

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Timestamps for Major Segments

• 00:19 – Introduction and overview of ChatGPT’s retail ambitions.
• 01:56 – Discussion: Benefits for retailers via Instant Checkout (Jinju Lee).
• 02:41 – Analysis: Drawbacks, risks, and ad revenue concerns.
• 03:36 – Strategies for retailers to counterbalance ChatGPT integration.
• 04:24 – Amazon’s stance and strategic caution.
• 06:02 – Altman’s dealmaking background and partnership with SoftBank.
• 08:06 – How Altman leverages industry competition to secure OpenAI deals.
• 09:52 – OpenAI’s financial challenges and speculative solutions.
• 10:39 – Risks of failed revenue growth and broader tech sector vulnerabilities.

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Summary

This episode delivers a timely, nuanced look at OpenAI’s latest innovations and the unprecedented dealmaking strategies of CEO Sam Altman. The new Instant Checkout feature positions ChatGPT as both a commercial platform and a disruptive force for retailers, who must balance potential gains with loss of customer touchpoints. Meanwhile, Altman’s bold maneuvers have enmeshed tech powerhouses in an interdependent—and precarious—AI ecosystem, raising existential questions for companies betting big on rapid and sustained growth.

Listeners come away with a deeper context for the promise and peril facing both established industry players and emerging AI giants as business, technology, and global investment become more tightly bound than ever before.

Transcript

[Sebastian Steinhauser]

Economic shifts, geopolitical change. In a world defined by disruption, what if leaders could turn uncertainty into advantage? Join SAP at the break to hear how organizations can stay resilient and stay ahead.

[Belle Lin]

Welcome to Tech News briefing. It's Friday, October 24th. I'm Belle Lin for the Wall street journal. We have two stories today about the company of the moment. OpenAI ChatGPT is by far the most popular AI chatbot right now. And while you might already use it to plan a vacation or spruce up your emails, OpenAI is betting that you'll use it to buy stuff too. We look at how retailers might be affected if shopping inside ChatGPT becomes ubiquitous. Plus, one of OpenAI CEO Sam Altman's greatest strengths is that of mega dealmaking. He's flown all over the world striking deals with some of the biggest companies behind the AI boom. But his high stakes tactics come with risks too. But first, OpenAI just released a new feature called Instant Checkout. It allows people to buy things directly through ChatGPT. So imagine asking it for a list of top reviewed backpacks and then buying your new bag without ever leaving the chatbot. While that seems easy and convenient for us, our Hurt on the street columnist Jinju Lee says it also comes with some drawbacks for the retailers who partner with it. So Jinju Walmart's stock jumped when it announced recently that shoppers could go through ChatGPT to buy stuff. Besides the bump in their stock, what are some of the possible benefits to retailers when consumers can shop directly through the chatbot?

[Jinju Lee]

It's not a huge number right now, but people are starting to look to chatbots for shopping ideas. If you are a retailer that's available on ChatGPT for instant checkout, which is what Walmart is Now allowing on ChatGPT, then you would have the first mover advantage there. If you're a shopper and you see two similarly priced things listed on ChatGPT, and on one of them you can click immediately to checkout, maybe you're more inclined to go for that option.

[Belle Lin]

So there are some potential upside to selling on ChatGPT. But you also write in your column that retailers have plenty of reasons to be wary. Why is that?

[Jinju Lee]

The frictionlessness that Instant Checkout introduces is a great thing because as a retailer, you want the shopping experience to be as fast as possible. You don't want people like clicking on a couple different links and then getting distracted and maybe not making the purchase. But also, retailers need to think about if enough people start using the instant checkout on ChatGPT and not leaving the platform at all to click on the retailer's website or app, that could potentially dent customer loyalty. And if there is less traffic on retailers websites, that could also hurt retailers ad revenue, which is a growing profitable part of many of their businesses.

[Belle Lin]

Is there anything that retailers can do to protect that customer relationship?

[Jinju Lee]

One thing might be they could just make certain products available for direct purchase on ChatGPT and not their entire inventory. Walmart, for instance, is allowing instant checkout for most things, but not for fresh produce. Another thing that Walmart has been able to do, and Amazon too, is they have their own internal AI chatbot tool for shopping. So if they make that chatbot really, really good, then maybe people will opt for that instead of using universal chatbots.

[Belle Lin]

Are there any retailers that so far haven't signed up for instant checkout or seem to be hesitant to jump on board?

[Jinju Lee]

One big company that is notably sitting out of this is Amazon, and there have been reports that in fact they are blocking these external genai tools from scraping their product data. And Amazon is working on a bunch of their own AI initiatives, including a tool that potentially would let customers shop for stuff outside of Amazon. Also worth noting that Amazon has a huge advertising business, so anything threatening their advertising business wouldn't be good for them.

[Belle Lin]

That was WSJ Heard on the street columnist Jinju Lee. Coming up, Sam Altman's wheeling and dealing has put OpenAI at the center of the AI boom, but it's also a precarious position to be in. We will dive into how Altman achieved his vision and what could come next after the break.

[Sebastian Steinhauser]

How can leaders find opportunity in uncertainty? Here's Sebastian Steinhauser, chief operating officer of SAP, on how businesses can build resilience in times of change.

The greatest catalyst uncertainty can bring for growth is if companies unlock the disruptive power of uncertainty by creating more agility to their business, because that to me is almost a source of competitive advantage in itself. The faster you can change, the faster you can adapt to uncertainty ahead of your competitors, the better you will perform.

[Belle Lin]

Sam Altman has managed to tie the fates of the world's largest semiconductor and cloud companies to his own company, OpenAI. It's certainly no small feat and didn't happen overnight. WSJ tech reporter Berber Jin has been looking into how Altman accomplished his goals and the risks he faces as the AI era is still just getting started. So Berber, to start, let's talk a little bit about the deal between Masayoshi San, the chief executive of SoftBank, and OpenAI and how that deal came together via Sam Altman.

[Berber Jin]

Masayoshi San is known as a really big risk taker in Silicon Valley. And sun had met Altman for dinner in 2023. And Altman had planted this idea in his head that if we were going to achieve these kind of superhuman forms of intelligence through AI, the world would need a lot more compute. And so at the time, Masa wanted to go really big into AI. In November 2024, the two of them sort of hatched this idea for Stargate, which was supposed to be this new company that would finance and build data centers for OpenAI across the US. Famously, they announced it at the White House on Trump's first day in office, and they promised to invest $500 billion building these data centers. And at the time, of course, all these big CEOs like Dario Amade at Anthropic and Satya Nadella and Elon Musk were saying they don't have the money, they have no idea what they're doing. And, and they weren't entirely wrong because as we've reported, that effort didn't really go anywhere. It's been very much scaled down. But it did kick off this latest set of deal making that Altman did to bring a lot of the cloud and semiconductor companies into deals with OpenAI.

[Belle Lin]

From your reporting, how was Sam Altman able to convince so many of these big companies to bet these massive amounts of money on him?

[Berber Jin]

The first thing is that this is what Altman loves to do. He's been doing it his whole career. He was a venture capitalist before becoming CEO of OpenAI. He's very good at selling a vision as well, and he kind of has these sort of very natural qualities of a deal maker. And more specifically, a lot of these deals come down to very basic element of human psychology, which is just like the fear of missing out. We reported that after Sam Altman and Masayoshin announced Stargate at the White House, that caught the attention of Jensen Huang at Nvidia and that kicked off the discussions that culminated in this huge hundred billion dollar deal announced last month. And through the course of all that, he was talking as well to Broadcom and amd. And what he's done is independently tied all of these companies to OpenAI. He's having them compete against one another, right, to build the best chip for OpenAI. And with Oracle, after Microsoft hesitated and didn't want to fund his big data center ambitions, he just found someone else. And we've reported that now Microsoft is considering giving OpenAI more computing capacity. So it very much is this kind of dance where he's daring each player to go bigger and promising them that if they buy into his vision for OpenAI, they could end up making a lot of money. And then the people who are more cautious, he's making them a little nervous, right, because he's finding other people who are willing to take the bigger bet.

[Belle Lin]

OpenAI is generating just about $13 billion this year, which isn't nearly enough to pay for the estimated $650 billion that you write it owes to its partners for all these computing deals. How will OpenAI pay for all of that?

[Berber Jin]

That's the question everyone is asking. Altman has said in interviews that he expects that a lot of it will just be paid with revenue growth. OpenAI has grown its revenue exponentially since ChatGPT took off. And internally they feel that they could be generating way more revenue than they do today if they had more computing resources and were able to release more products. And Altman has alluded coyly to some new financing strategies he's developing where some of these chip suppliers and cloud companies might even help OpenAI find a way to pay for these deals.

[Belle Lin]

What happens if that growth doesn't continue? If Sam Altman's conviction that revenue will grow with more computing power and demand will be there, what if that doesn't happen?

[Berber Jin]

So that's another question that is bubbling below the surface. It is this kind of surreal effect where essentially investors expectations around AI are growing larger and larger, where the assumption is that OpenAI will continue to grow at these huge rates. So if OpenAI doesn't, if something comes out about OpenAI's revenue growth slowing or any indication that the market might not be as big as OpenAI says it is, it's very plausible to see a big sell off in tech stocks. And he's tying the fates of a lot of the biggest cloud and chip companies to OpenAI.

[Belle Lin]

That was WSJ tech reporter Berber Gin. And that's it for Tech News Briefing. Today's show was produced by Julie Chang. Jessica Fenton and Michael Lavelle wrote our theme music. Jessica Fenton is our technical manager. Our development producer is Aisha El Musleam. Chris Zinsley is the deputy editor and Falana Patterson is the Wall Street Journal's head of news. Audio logging off. I'm your host, Bel Lin. We'll be back later this morning with TNB Tech Minute. Thanks for listening.

[Sebastian Steinhauser]

Uncertainty is inevitable, but it doesn't have to hold your business back. Here's Sebastian Steinhauser of SAP again on how companies can adapt to the unpredictable.

And thrive Technology is the greatest tool in your tool set to help you create that capability to train that muscle in your enterprise to adapt to fast to change in the environment. And that's where customers are turning to SAP now to say, hey SAP, you already run our most mission critical processes in our enterprise. Help us apply generative AI, agentic AI, apply this disruptive technology to improve our agility when it comes to making fast decisions for our business in a very uncertainty economic environment.

Learn more about how SAP helps businesses conquer [e-mail] Uncertainty Custom content from WSJ.

[WSJ Advertising Department]

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