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)

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.

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.

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]

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]

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.

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.