Alex Schiff

Product @Try_Headway. Prior: built Square AI @Square, built @scannedbyCanvas at @occipital, cofounder @Fetchnotes, BD and occasional talking head @Benzinga

[Alex Schiff @alexschiff]

Square AI in action alongside my accidental start as a food influencer 🤣

[Square @Square]

The right insight at the right moment can change everything. We sat down with @salt_hank to explore how Square AI delivers those insights in seconds—so owners can make smarter moves, faster.

Discover the latest tools from Square in Releases Vol. 2: https://t.co/F8VDPQxKl5

[Alex Schiff @alexschiff]

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

[John Collison @collision]

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

[Alex Schiff @alexschiff]

@lennysan Headway hiring a bunch: https://t.co/c38rDiZ8OX

[Alex Schiff @alexschiff]

Singular argument for moving to NYC

[Will McKelvey @Will_McKelvey]

You went to a real NYC party this weekend if you:
- had a good time and made some new friends

[Alex Schiff @alexschiff]

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.

[Dean W. Ball @deanwball]

https://t.co/S7tXum85dc

[毛丹青 @maodanqing]

AIが復元した「清明上河図」に言葉を失う。確かに、AI特有の「滑らかすぎる質感」に違和感を覚える瞬間もある。だが、張択端が描こうとした千年前の喧騒が、圧倒的な解像度で迫ってくるのも事実だから、これは模写ではない。AIという異質なフィルターを通すことで、われわれは初めて「大宋」の熱気に触れる。賛否はあろうが、この没入感だけは否定できないかもしれない。

[Alex Schiff @alexschiff]

A+ ad for our era. 10/10 for @AnthropicAI

[Tom Warren @tomwarren]

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

[The Minnesota Star Tribune @StarTribune]

Tomorrow’s front page of the Minnesota Star Tribune: Jan. 23, 2026

[Ben Hunt @EpsilonTheory]

Front page of WSJ just now. Hang it in the Louvre, man.

[sophie @netcapgirl]

“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”

[Alex Schiff @alexschiff]

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

[Morgan McKay @morganfmckay]

.@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

[Alex Schiff @alexschiff]

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

[Armand Domalewski @ArmandDoma]

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

[OSINT Gorilla @GorillaOSINT]

Europeans with 0% annual GDP growth watching America become a 3rd World Country

[Alex Schiff @alexschiff]

Normalize dunking on bad criticism like this

[Alex Schiff @alexschiff]

Bless your heart ChatGPT

[Nate Silver @NateSilver538]

My favorite genre is still ChatGPT not believing current political developments when I ask it for a copy edit.

[Adam Nash @adamnash]

Future of legislatively required human monitors for self-driving trucks

[Sports Jim III @SportsAndChup]

This just in from: Bill Bonds #JBOS

[Ethan Mollick @emollick]

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."

[Alex Schiff @alexschiff]

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)

[Ethan Mollick @emollick]

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.

[Alex Schiff @alexschiff]

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.

[Aaron Levie @levie]

“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.