Morning Brew Daily

Episode: Oracle Scores $300B OpenAI Deal & Digital Creators Get Huge Tax Break

Date: September 11, 2025
Hosts: Neal Freyman & Toby Howell

Episode Overview

In today's episode, Neal and Toby dive into a packed news cycle featuring Oracle’s meteoric rise thanks to a stunning $300 billion OpenAI cloud deal, explore a major new tax break for digital creators, examine the rollout of Amazon’s Zoox robotaxis in Las Vegas, touch on unexpected policy quirks (like the explosion of “99 unit” apartment buildings), and share quirky stats and headlines that shape the day.

Key Discussion Points & Insights

1. Oracle’s Billions: Hitting the AI Jackpot

[02:30–07:40]

• Larry Ellison Becomes World’s Richest Person
  Oracle’s stock soars 35% overnight, catapulting Ellison’s net worth to nearly $400 billion. Massive growth projections for cloud infrastructure and AI fuel the hype.

  • “After Oracle, the company he founded and now chairs surged 35% yesterday, Ellison’s personal fortune soared by $89 billion, pushing him to a nearly $400 billion net worth and into the top spot over his pal Elon Musk.” — Toby Howell [02:32]

• The Role of OpenAI’s $300B Deal

  • Oracle reportedly lands a $300 billion, five-year contract to provide cloud computing power for OpenAI. This single deal underpins Oracle’s explosive revenue expectations.
  • “A huge chunk of that comes from one company, though... Just kidding. It’s OpenAI, who, according to reports, agreed to purchase $300 billion alone in computing power over the next five years.” — Toby Howell [03:36]
  • Investors ignore Oracle’s disappointing recent earnings; focus is on the AI-driven future.

• The Inflection Point for Oracle

  • Oracle pivots from sleepy database giant with 1.6% annual growth to AI engines fueling exponential expansion.
  • But: To meet these contracts, Oracle needs massive data center buildout, significant capital expenditure, and access to scarce Nvidia GPUs.
  • “That’s going to require a ton of power—four and a half gigawatts of capacity. That’s as much as the Hoover Dam creates. Actually, two Hoover Dams.” — Toby Howell [04:57]

• Skepticism Around OpenAI’s Spending Power

  • OpenAI’s current annual revenue is only ~$10B, and it remains unprofitable. Future cloud spend commitments far exceed current income, implying enormous growth assumptions for AI products like ChatGPT.
    • “Their commitment starting in 2027 is to spend $60 billion with Oracle going forward. So that is six times [OpenAI's] current revenue just to secure compute.” — Toby Howell [06:44]
    • Hosts caution: “Maybe some cracks forming in that $300 billion pledge.” [06:44]

• The Billionaire Lifestyle

  • Postscript on Larry Ellison’s spending sprees—owning 98% of Lanai, buying the “Tolkien & Lewis” pub in Oxford for $10.7M, etc.
    • “So, you know, he’s just doing the billionaire thing, right?” — Neal Freyman [07:40]

2. Digital Creators Get a Big Tax Tip

[08:08–10:52]

• New Tax Deductions for Tipped Workers (Including Influencers!)

  • As part of a new law, individuals in tipped professions—now including digital content creators (Twitch streamers, OnlyFans, podcasters, etc.)—can deduct up to $25,000 in tips per year.
  • “That inclusion could shift the business model of creators... now the new rules make digital tips disproportionately attractive, since they can be written off in ways other revenue streams cannot.” — Toby Howell [08:38]

• The Business Model Impact

  • Platforms are expected to prioritize “tip” buttons, making tips the most tax-efficient way for creators to get paid.
  • “You can bet that these platforms right now... are going to roll out these incredibly lucrative and visible tip buttons everywhere.” — Neal Freyman [09:23]

• The Politics of Creatorship

  • The rise of creators as a political bloc: giving tax breaks buys influence and loyalty, with even dedicated White House press seats for creators.
  • “I do think that this is the coming of age of creators as almost a political bloc as well...” — Toby Howell [10:07]

• Who Else is Included?

  • 68 professions, including DJs, clowns, ushers, gardeners, skydiving pilots, etc., are eligible.
  • Notably, more than one-third of tipped workers earn too little to pay federal tax, so this only benefits higher-earning segments.

3. Amazon’s Zoox Robotaxi: Vegas or Bust

[12:52–15:02]

• Robotaxi Wars Heat Up

  • Zoox, Amazon’s AI car project, launches its first public service in Las Vegas—competing with Waymo (Google), Tesla, and others.
  • Free rides initially, as Amazon wants to build market share.

• Futuristic “Toaster on Wheels”

  • Zoox’s design: Fully driverless, no steering wheel or pedals, two rows of seats facing each other, panoramic windows.
  • “They have no steering wheel or pedals, so they are fully committed to being an autonomous vehicle... a toaster on wheels.” — Toby Howell [13:04]
  • Philosophical distinction: Unlike Waymo or Tesla, Zoox builds new vehicles from scratch—maximum autonomy, quirky design.

• The Automation Arms Race

  • Current singles: One vehicle produced per day; hoping to scale to three per hour.
  • None of the major robotaxi efforts are profitable; all are subsidized by parent company cash as a long-term bet.

4. Neil’s Numbers: Three Quirky Stats

[16:42–23:34]

• Health Insurance Premiums Surge ([16:42])

  • Health insurance costs will rise the most in 15 years—up 6.5% for employer plans in 2026; up 18% for ACA marketplace plans.
  • AI cited as a cost inflator as providers leverage it for billing and care management.
  • “$25,000, the price of a small car [is now] the recent average for family coverage...” — Neal Freyman [17:09]

• NYC’s “99-Unit” Apartment Boom ([19:08])

  • Developers flock to 99-unit buildings—twice as many permits as in previous 16 years—because labor law thresholds for bigger projects kick in at 100 units (requiring $40/hr wages).
  • Obsessing over 99: reminiscent of historic “window taxes” and the “cobra effect” (unexpected consequences of policy).
  • “It’s just fascinating how you make one policy and you just can’t necessarily know... how people are going to react to those incentives.”—Toby Howell [20:14]

• No No-Hitters in Baseball ([21:13])

  • No Major League Baseball no-hitters this season—a statistical rarity amid a recent era of frequent no-no’s.
  • Possible reasons: batters’ averages tick up, pitchers pulled early, or just random chance.
  • “You have to mention, Yamamoto being a single out away, like that is a crazy thing we have to mention too.” — Toby Howell [22:26]

5. Rapid-Fire Headlines ([23:34–26:51])

• Klarna IPO
  Klarna, Swedish "Buy Now, Pay Later" fintech, debuts on NYSE at $17B valuation (still unprofitable: lost $153M on $1.5B revenue in H1). Early investors like Sequoia win big, while Softbank is still underwater due to higher 2021 valuations.

  • “If you are Masayoshi Son... you invested when Klarna’s valuation was at $30B, double what it is now.” — Neal Freyman [24:26]

• World Cup Ticket Fiasco
  Visa pre-sale for World Cup tickets overwhelmed servers, causing confusion as the system crashed, though there’s no timing advantage in the first lottery round.

Notable Quotes & Memorable Moments

• On Oracle’s Pivot:
  “Shades of Nvidia here in terms of an old hat Silicon Valley company catching fire because of AI.” — Neal Freyman [04:21]

• On OpenAI’s Price Tag:
  “So everyone was kind of scratching their heads going huh? We're kind of relying on some pretty lofty revenue assumptions coming down the pipeline for a company that is nowhere near profitable right now.” — Toby Howell [06:44]

• On the Creator Tax Law:
  “It looks like we are seeing this young, influential, very online [group] becoming offered material incentives in order to kind of align themselves with a certain political party because they’ve just become so powerful in today’s modern age.” — Toby Howell [10:07]

• On the Robotaxi Race:
  “What happens in a Vegas Zoox stays in a Vegas Zoox.” — Neal Freyman [12:59]
  “They wanted to start from scratch, they wanted to reimagine what a car even is. And apparently what they came up with was a toaster on wheels.” — Toby Howell [13:04]

• On NYC Housing Policy: “If someone looks at a construction site and asks you, I wonder how many units this will be? You can't go wrong with guessing. 99.” — Neal Freyman [20:14]

• On Health Insurance Costs: “Health care costs are already straining American households, even before the upcoming price hikes. The recent average for family coverage was about $25,000, or the price of a small car.” — Neal Freyman [17:09]

Timestamps for Major Segments

• Oracle/OpenAI & Ellison’s Wealth: 02:30–07:40
• Digital Tips Tax Break for Creators: 08:08–10:52
• Amazon’s Zoox Robotaxi Launch: 12:52–15:02
• Neil’s Numbers (Insurance, Housing, Baseball): 16:42–23:34
• Klarna IPO & World Cup Tickets: 23:34–26:51

Overall Tone and Takeaways

This episode blends sharp business analysis with wry, playful banter. Major themes include the wild flow of money in tech and AI, the unexpected ways tax policy shapes behaviors, and the ongoing collision of tech, politics, and culture. The hosts’ mix of curiosity, skepticism, and humor makes even arcane financial news engaging—and shows just how many industries are being disrupted, for better or worse, by AI and new economic incentives.

If you missed the episode, this summary gives you the key insights, quirky sidelines, and memorable lines that Morning Brew Daily fans love.