Happy Friday.
The current thing in tech and business is the tokenmaxxing reckoning as high-profile executives begin to question how much AI actually increases productivity.
Today’s lineupTech blogger John Gruber at 11:30 AM
Trajectory Co-Founder Ronak Malde at 12:00 PM
Picogrid Co-Founder & CEO Zane Mountcastle at 12:10 PM
Pace Founder & CEO Jamie Cuffe at 12:20 PM
NBA champion & entrepreneur Kyle Kuzma at 12:30 PM
Altimeter Capital Founder & CEO Brad Gerstner at 12:50 PM
Blue Origin’s New Glenn explodes on the launchpad
Jeff Bezos’ rocket company suffered a catastrophic failure last night when its New Glenn rocket, a reusable heavy-lift orbital spacecraft designed to compete with SpaceX’s Falcon Heavy, exploded in a massive fireball on its launchpad in Cape Canaveral, Florida. Thankfully no one was hurt. Bezos tweeted, “Very rough day, but we’ll rebuild whatever needs rebuilding and get back to flying. It’s worth it,” and Elon Musk lent his support as well, tweeting “Most unfortunate. Rockets are hard.” The explosion caused extreme structural damage to its only functional launchpad. While Blue Origin has successfully reached space a number of times with other vehicles, New Glenn has had just one successful flight out of three attempts. From 2006-2008, Elon Musk had three consecutive failures with the Falcon 1 before successfully launching it. — Brandon
ROImaxxing
We are certainly in a fast takeoff of enterprise AI adoption. Anthropic recently passed $47B in ARR and raised a massive $65B series H at a $965B post-money valuation. Last November, Claude Code was going viral among early adopters and small vibecoded apps were launching daily, but Q2 2026 was clearly a massive moment for Fortune 500 wide scale rollouts. This has become a double-edged sword for some organizations. “Tokenmaxxing” dashboards have reportedly led to potentially ROI-negative AI use at name-brand companies like Meta, Uber, and now AWS. The bull case is that the cost per task completed by AI will decrease very quickly, so even if you’re spending half a billion per month on tokens today, the same output will be available next year for a tenth of the cost. At the same time, there’s debate over whether AI tooling is being pointed at the most high-leverage problems in these organizations. Outside of stories of “workers using AI agents to check the weather” and running endless loops trying random different make-work projects, there’s definitely a worry that truly needle-moving features aren’t being pulled forward like people would expect. At the end of the day, company management will have to demonstrate ROI from token spend. The next round of earnings reports should show material changes in OpEx and downward movement in net income without other justification will be met with tough questions from analysts. At the same time, if you believe, as all the trends indicate, that AI is a new and useful tool that will decrease in cost over time, some lumpy ROI in the short term to reorient your organization around a new motion at work is completely justifiable. You just probably don’t want a literal tokenmaxxing dashboard. You have to channel both Jevons Paradox (when something becomes more efficient to use, people often end up using more of it, not less.) and Goodhart’s Law (when a measure becomes a target, it ceases to be a good measure.) — John
Clip Spotlight: Match Group CEO questions ROI on AI spendMatch Group CEO Spencer Rascoff says his company is adding millions in new AI expenses, and many CEOs still aren’t sure when the payoff will fully show up.
“So our approach is that we have to pay for these tools. For us, it’s $5-10M a year that we’re spending on AI tools from basically nothing. So we’re slowing down hiring somewhat. That’s how we’re choosing to fund it.”
“In terms of when do we start to see the actual benefit? CEOs, CFOs, and I are starting to ask that question more and more. I think we’re benefiting from it, but it’s hard to feel it.”
From his appearance on the show earlier this month.
HeadlinesWSJ: Blue Origin’s New Glenn Rocket Explodes on Launchpad
Stratechery: The SpaceX IPO and Data Centers in Space
TechCrunch: Anthropic raises $65 billion, nears $1T valuation ahead of IPO
NYT: Why Peter Thiel Is Decamping to the End of the World
FT: Amazon scraps AI leaderboard to stop workers chasing usage scores
Axios: AI sticker shock hits corporate America
CNBC: Mark Zuckerberg says a Meta cloud computing business ‘definitely on the table’
Bloomberg: China Expands Travel Curbs to Top AI Talent at Private Firms
FT: Kirkland & Ellis to spend $500mn building its own AI technology
Bloomberg: Apple to Overhaul iOS 27 Siri, AI Features: Here’s a First Peek
Axios: Scoop: Groq raising $650 million for its second act
The Information: Base Power in Talks to Raise Funds at $12 Billion Valuation
Reuters: Exxon wins shareholder backing for legal move to Texas
WSJ: Putin’s $26 Billion Longevity Push
Bloomberg: How Barnes & Noble Became Private Equity’s Most Radical Retail Experiment
Bloomberg: Robinhood Adds Some Agents
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