Product @Try_Headway. Prior: built Square AI @Square, built @scannedbyCanvas at @occipital, cofounder @Fetchnotes, BD and occasional talking head @Benzinga
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This has been my default expectation for awhile. There are all kinds of sticky effects from regulation, networks, etc that might muddy how this unfolds but so many things break at 10k+ employees I can’t imagine any founder would choose to be so big if revenue didn’t depend on it
We've been thinking a lot at Stripe about the Coasean lens on AI:
- The obvious near-term effect is reduced transaction costs within companies: shared context, systems of record, aligned incentives etc.
- But inter-company transaction costs also reduce sharply: agents are great at discovery, make it trivially easy to integrate; make contracting much more straightforward; agent-to-agent commerce.
- On net, we think second effect bigger in medium term: fewer people per firm, more output per firm, just more firms, and more coordination happening through market-like mechanisms
This is from someone who served in the Trump administration, on the Anthropic issue. Understandably it is getting less attention than Iran this weekend, but it is not less worrisome. We live in a profoundly dumb timeline.
Anthropic just took a big swipe at OpenAI's decision to put ads in ChatGPT. Anthropic is airing ads mocking ChatGPT ads during the Super Bowl, and they're hilarious 😅 Anthropic is also committing to no ads in Claude https://t.co/LR1v4xz9ds
“sometimes i feel like just saving part of my income won’t be enough for retirement, what should i do?”
“you’re sharp to realize that and thinking ahead is a trait of rich people. gambling is not just entertainment — it’s a way to escape the permanent underclass. try DraftKings”
Proof will be in the results vs the study but amazing step. @NYCMayor I used to work with small businesses that had to throw fundraisers just to pay for fees and costs associated with all the rules for outdoor seating. Would love to see something similar targeting indirect costs
.@NYCMayor signed an executive order that directs seven city agencies to create a comprehensive inventory of all the fees and civil penalties that small businesses pay in NYC - with the intent of trying to reduce/cut some of these fines and fees
The democratic socialist mayor of New York is pushing pro-housing YIMBY policies while the Republican real estate developer president is trying to ban private equity landlords and institute price controls on credit cards. 2026 is f’ing wild
as a Californian i am so jealous of NY right now. I cannot in a million years imagine any CA DSA chapters endorsing CEQA reform to make building housing easier
GPT-5, Claude, Kimi, and Gemini: "I can travel back in time to any time before 1500 and change only one thing, what is the single thing you would change, nothing obvious."
TBH this has always been the case. Every team I’ve been on has had different expectations of where the PM role begins and ends. Possibility space just gets bigger with AI (as with other roles)
The fight over what a product manager does is going to among the first major AI organizational design problems faced by companies.
It is a job right at the center of what AI can do with first pass coding, marketing, design, ideation, etc. Who will own which pieces up for grabs.
This is by far the most under appreciated aspect of AI tools in 2025. Automation is valuable, yes, but it is the easiest thing to think about - augmentation and doing more than you did before (and/or at higher quality) is where alpha really comes from.
“Many of the projects I do with Claude day to day I just wouldn't have done at all pre-Claude.”
One of the underestimated impacts of AI agents will be the fact that work will just change in unexpected ways because we’ve made something abundant very cheap.
This is why no one really knows what jobs will look like in the future. We imagine taking today’s definition of work and applying automation to it. But in practice, the tools end up changing the work.
The sales engineer now builds full custom demos for customers. The developer takes on way more features than was anticipated or works on skunk works projects that couldn’t have been justified before. The lawyer reviews contracts that were previously below the threshold where it was worth it.
We’re just in the beginning of figuring out that’s this new morphed world will look like.