Greg Bayer

Co-founder & CEO @tailorhq_ai. Previously: Leading Eng for @get_Magical, @LI_learning, Pulse News (acquired by @LinkedIn)

[Akshay Kothari @akothari]

We're finally shedding the .so (thank you Somalia!), and using the .com for @NotionHQ. And for this beautiful moment, I want to share a fun story:

Back in 2018, I had just joined Notion, and one of the first things @ivan asked me to do was figure out how we could own https://t.co/BxoFvc83VG. I had never done a big domain purchase before, so I reached out to a few domain brokers to understand the landscape. We tried different brokers, kept things anonymous, and attempted to surface a price the seller might consider.

A year went by… nothing. Meanwhile, it was pretty clear this was only going to get more expensive as we grew. We needed a different approach. A fellow founder connected me to a broker who took a very different tack. Less transactional, more long-term relationship builder. He spent months getting to know the domain owner. Turns out owner was a fellow entrepreneur in the west coast… and a huge Grateful Dead fan.

So we figured, why not get creative? Something beyond just price. So I called up our investor Ronny Conway and asked if there was any way he could help set up a private meeting between the domain owner and the Grateful Dead. Ronny is one of those people who somehow makes impossible things possible. A week later he calls me back: “New York City. Halloween. 15 minutes after the concert. Done.”

The broker went back to the owner with an offer: some cash, some equity, and a private meeting with the Grateful Dead. That got his attention. He didn’t take the band meeting in the end, but he did lean into the equity (great call, in hindsight). We shook hands, and a few weeks later, the deal was done.

I’ve been waiting years for the day we move our product to https://t.co/BxoFvc83VG. Looks like 2026 is finally the year. Safe to say I’m unreasonably excited about this update!

[Paul Graham @paulg]

The only thing worse than having the CEO knee-deep in building stuff with AI is not having the CEO knee-deep in building stuff with AI.

[GREG ISENBERG @gregisenberg]

I just got back from SF and I FEEL INSPIRED.

I spent 5 days with frontier AI model teams, AI startup founders, and 3 billionaires.

My takeaways:

1. I had lunch with 3 billionaires. All of them are buying SaaS companies and rebuilding them agent-first. They were deeply inspired by Bending Spoons and Ryan Cohen's eBay deal. Buy the company, cut the headcount, rebuild the tech, add agents, add features, make more valuable experience, raise prices.

2. The frontier model companies are hungry for usage data from the field. They can see API calls and token counts. They can't see the actual workflows. If you're deep in a niche using these models in ways the model companies haven't seen, that understanding is incredibly valuable. Usage intelligence is the new alpha.

3. Consumer AI is massively underbuilt. Every billboard in SF is either B2B inference infrastructure or vertical agent companies. The entire city is optimized for enterprise. Meanwhile you have companies like Cal AI doing $50M ARR in 18 months as a consumer app. I met with a cool few teams doing consumer AI (@paulscherer / @ekuyda)

4. MCP came up in literally every conversation. The companies exposing their product as MCP endpoints are getting pulled into deals they never pitched for. The ones that aren't are becoming invisible to agents. This is the new SEO. If agents can't find you, you don't exist. Building products for agents is the new zeitgeist in general.

5. Not uncommon for hot seed rounds to be $25-50 million valuations. I saw a Series A at $450 million

6. If I had a dollar every time someone mentioned "forward-deployed engineer" this trip I could have funded a seed round. It's the hottest role in SF right now. The person who sits between the agent and the customer, making sure everything actually works.

7. The mood around open source shifted. A year ago it felt like open source was chasing the frontier models. Now founders are telling me Gemma and DeepSeek are good enough for 80% of what they need at a fraction of the cost. The "which model do you use" conversation is being replaced by "which model for which task." Model loyalty kinda feels dead.

8. Voice agents came up more than I expected. Multiple founders told me voice is the interface for the next billion users. The billion people who will never type a prompt will absolutely talk to one.

9. The Obsidian community in SF is weirdly intense. Multiple founders showed me their vaults unprompted. Like showing someone your home gym. It's a flex now. The quality of your knowledge base (second brain?) is becoming a status symbol among builders.

10. Maybe it was just the people I met but the age of the founders is shifting. I met more founders over 40 this trip than any trip before and more founders under age 21 than ever before. Founders getting older and younger at the same time.

11. I spoke to a lot of fast-growing startups, VCs and frontier models who are hiring content creators right now.

12. The restaurant scene in SF is actually better than it's been in years. Founders are going out more. Alcohol is out, not surprisingly.

13. SF doesn't feel like the only place anymore. We all have access to the same frontier models. We all read the same X feed. A founder in NYC or Lagos is calling the same APIs as a founder in SoMa. So in the past it felt like SF was always lightyears ahead, doesn't feel that way anymore. It's okay not to live in SF and have BIG DREAMS.

14. The coworking spaces in SF are half empty but the coffee shops are packed. People want to be around people. I had a few startup ideas here....

15. Walking around the Mission I noticed something: the street-level businesses, the taquerias, the barbershops, the laundromats, none of them use any AI at all.

16. I heard the phrase "agent debt" for the first time. Like technical debt but for agents. When you hack together an agent workflow fast and never clean it up, the system prompts conflict, the memory gets polluted, the tools overlap. 6 months later the agent is doing weird things and nobody knows why lol.

17. Met a few people who carry two phones now. One for personal. One that's basically an agent terminal running Telegram or iMessage connections to their agent fleet.

It's always amazing to get that dose of inspiration in SF. I FEEL INSPIRED.

But I'm so happy to be back home, locked in and building.

We're 12-18 months into a shift that will take 15 years to play out. The urgency in every conversation was real.

What an incredible time to be building.

[Ivan Zhao @ivanhzhao]

The loudest story about AI is a lonely one. One person with an army of chatbots. Other humans are friction.
That gets the future wrong. The best things aren’t built alone.
In a moment of change, we want to remind the world (and ourselves) what Notion stands for:
— Think Together

[Greg Bayer @gregbayer]

@cjc You got me!

[Greg Bayer @gregbayer]

@farhadnoorzay 💯 One-shot “make me a webapp for this”. Mind blowing vs other vis options.

[Akshay Kothari @akothari]

One interesting trend over the past year is how quickly vibes complete the full circle. In just the last few months, we’ve done multiple round trips:

- PMs went from “the role is dead” to “we still need PMs” to “PMs might be the most important function.”
- Software engineering went from “AI will wipe out coding jobs” to “new grads can’t get hired” to “software hiring is booming again.”
- SaaS itself went from “software is dying” to SaaSpocalypse to “actually, AI is software too. We are so back!”

[Greg Bayer @gregbayer]

@christinacaci Congrats @christinacaci!! Very impressive. Can’t wait to see what’s next for Vanta. Also a happy customer.

[Paul Graham @paulg]

Sadly, one way I now recognize fake AI-generated replies is that AIs write punchier sentences than most ordinary humans.

[himanshu @himanshustwts]

Based on everything explored in the source code, here's the full technical recipe behind Claude Code's memory architecture:

[shared by claude code]

Claude Code’s memory system is actually insanely well-designed. It isn't like “store everything” but constrained, structured and self-healing memory.

The architecture is doing a few very non-obvious things:

> Memory = index, not storage
+ MEMORY.md is always loaded, but it’s just pointers (~150 chars/line)
+ actual knowledge lives outside, fetched only when needed

> 3-layer design (bandwidth aware)
+ index (always)
+ topic files (on-demand)
+ transcripts (never read, only grep’d)

> Strict write discipline
+ write to file → then update index
+ never dump content into the index
+ prevents entropy / context pollution

> Background “memory rewriting” (autoDream)
+ merges, dedupes, removes contradictions
+ converts vague → absolute
+ aggressively prunes
+ memory is continuously edited, not appended

> Staleness is first-class
+ if memory ≠ reality → memory is wrong
+ code-derived facts are never stored
+ index is forcibly truncated

> Isolation matters
+ consolidation runs in a forked subagent
+ limited tools → prevents corruption of main context

> Retrieval is skeptical, not blind
+ memory is a hint, not truth
+ model must verify before using

> What they don’t store is the real insight
+ no debugging logs, no code structure, no PR history
+ if it’s derivable, don’t persist it

[Boaz Barak @boazbaraktcs]

New blog post: the state of AI safety in four fake graphs.

[Akshay Kothari @akothari]

Alright, here’s the public TestFlight build: https://t.co/hcn5hTcvwv

Fully vibe-coded w/ no backend. The whole app is less than 1MB. Built in ~6 hours, in between meetings. Try it out, and send me feedback!

[Greg Bayer @gregbayer]

@akothari Wow! 🤩 🤯 As soon as it hits 1M users, are we going to Tahoe again?

[Greg Bayer @gregbayer]

@amorriscode good old Y2K style time bugs are still with us 🙃

[Greg Bayer @gregbayer]

@paulg Can this lead anywhere other than agents emailing agents, and humans only stepping in after N levels of triage?

[Greg Bayer @gregbayer]

@ycombinator @sila_hq What’s old is new again.

[Ivan Zhao @ivanhzhao]

Watch THIS. The most comprehensive demo of using Custom Agents + Workers to automate your startup, side project, or whatever you're working on...

[Paul Graham @paulg]

Someone asked what's the most underappreciated quality in startup founders. I realized I could answer this by asking what's the most underappreciated aspect of startups. That's easy: how hard they are. So the most underappreciated quality in founders is sheer toughness.

[Sam Altman @sama]

Peter Steinberger is joining OpenAI to drive the next generation of personal agents. He is a genius with a lot of amazing ideas about the future of very smart agents interacting with each other to do very useful things for people. We expect this will quickly become core to our product offerings.

OpenClaw will live in a foundation as an open source project that OpenAI will continue to support. The future is going to be extremely multi-agent and it's important to us to support open source as part of that.

[Sam Altman @sama]

I am very excited about AI, but to go off-script for a minute:

I built an app with Codex last week. It was very fun. Then I started asking it for ideas for new features and at least a couple of them were better than I was thinking of.

I felt a little useless and it was sad.